# 0

**SMILES:** C1=CC=C(C(=C1)C2=NC=CC(=N2)N3C=CN=C3)Cl

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a member of the pyrimidine class and features a 2-chlorophenyl group and a pyrazolyl group attached to the pyrimidine ring. The presence of these functional groups plays a crucial role in determining the molecule's permeability.

The pyrimidine core is a heterocyclic aromatic compound, which generally contributes to the molecule's stability and planarity. This aromatic nature can facilitate interactions with the artificial membrane, potentially enhancing permeability due to favorable π-π stacking interactions with the membrane's aromatic components.

The 2-chlorophenyl group introduces a chlorine atom, which is a halogen. Halogens can increase lipophilicity, which is the molecule's ability to dissolve in fats, oils, and lipids. This increased lipophilicity can enhance the molecule's ability to permeate through the lipid-rich environment of the artificial membrane, suggesting high permeability.

The pyrazolyl group is another heterocyclic aromatic ring, which can also contribute to the molecule's overall aromatic character. This group may further stabilize the molecule's interaction with the membrane through additional π-π interactions.

Overall, the combination of the pyrimidine core, the 2-chlorophenyl group, and the pyrazolyl group suggests that the given molecule likely exhibits high permeability in the Parallel Artificial Membrane Permeability Assay due to its aromatic nature and increased lipophilicity.

Final answer: High permeability.

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# 1

**SMILES:** CC1=NC(=NC2=CC=CC=C12)N

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a derivative of quinazoline, which is a bicyclic compound consisting of a benzene ring fused to a pyrimidine ring. The presence of the quinazoline core is significant because it is a planar, aromatic structure that can facilitate interactions with biological membranes, potentially enhancing permeability.

The molecule also features an amine group attached to the quinazoline core. Amines are known to be polar and can form hydrogen bonds, which may increase the molecule's solubility in aqueous environments and enhance its ability to interact with the polar head groups of the artificial membrane.

Additionally, the methyl group attached to the quinazoline ring can influence the molecule's lipophilicity. Methyl groups are hydrophobic, which may enhance the molecule's ability to penetrate lipid membranes by increasing its overall hydrophobic character.

Overall, the combination of the aromatic quinazoline core, the polar amine group, and the hydrophobic methyl group suggests that the given molecule may have moderate to high permeability in the PAMPA assay, as it possesses both hydrophilic and hydrophobic characteristics that can facilitate interaction with the artificial membrane.

Final answer: High permeability

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# 2

**SMILES:** C1=NC(=C2C(=N1)N(C=N2)[C@@H]3[C@@H]([C@@H]([C@@H](O3)CO)O)N)N

**Label:** 0

**Predi:** 0

**Correct:** 1

# Response:
The given molecule is a nucleoside analogue, specifically a deoxyribonucleoside, which is a building block of DNA. Its structure consists of a purine base, specifically adenine, linked to a sugar moiety, which is a modified ribose sugar. This sugar is a deoxyribose, meaning it lacks an oxygen atom at the 2' position compared to ribose.

The purine base, adenine, is attached to the sugar at the 9-position, forming a glycosidic bond. This is a characteristic feature of nucleosides, where the purine base is linked to the sugar through a nitrogen atom.

The presence of amino groups on the purine base and the sugar moiety increases the molecule's hydrophilicity, which can influence its permeability. The amino groups can form hydrogen bonds with the artificial membrane, potentially enhancing its interaction with the membrane.

The hydroxymethyl group on the sugar moiety also contributes to the molecule's hydrophilicity and can participate in hydrogen bonding. This feature may facilitate the molecule's interaction with the membrane, affecting its permeability.

Overall, the structural features of the given molecule, such as the purine base, the deoxyribose sugar, and the amino groups, suggest that it may have moderate permeability in the PAMPA assay. The balance between hydrophilic and hydrophobic interactions with the artificial membrane will determine its permeability.

Final answer: Low-to-moderate permeability.

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# 3

**SMILES:** CN1CCC2=CC(=C3C4=C2[C@H]1CC5=CC=C(C=C5)OC6=C(C=CC(=C6)C[C@H]7C8=CC(=C(O3)C=C8CCN7)O4)OC)OC

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a complex natural product with a highly intricate structure, as indicated by its IUPAC name. This molecule is characterized by multiple rings and heteroatoms, which are crucial in determining its permeability.

The presence of methoxy groups in the structure suggests that the molecule has some degree of lipophilicity, which can enhance its ability to permeate lipid membranes. Methoxy groups can also influence the molecule's solubility and its interaction with the artificial membrane, potentially increasing its permeability.

The molecule also contains multiple ether linkages, as indicated by the 'oxa' components in the name. These ether groups can contribute to the molecule's flexibility and ability to interact with the membrane, potentially facilitating its passage through the artificial membrane.

Additionally, the molecule has nitrogen atoms, as denoted by 'diaza' in the name. These nitrogen atoms can participate in hydrogen bonding and ionic interactions, which may affect the molecule's permeability by interacting with the functional groups on the artificial membrane.

The complex polycyclic structure of the given molecule suggests a rigid framework, which can influence its ability to fit into the membrane pores. The rigidity can either hinder or facilitate permeability, depending on the size and shape of the membrane pores.

Overall, the combination of methoxy groups, ether linkages, and nitrogen atoms, along with the rigid polycyclic structure, suggests that the given molecule may have moderate to high permeability in the PAMPA assay, depending on the specific interactions with the artificial membrane.

Final answer: Low-to-moderate permeability.

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# 4

**SMILES:** C1=CC2=C(C=C1I)C(=CC3=CC(=C(C(=C3)Br)O)Br)C(=O)N2

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several functional groups and structural elements that influence its permeability in the PAMPA assay. Let's break down the key components and their impact on permeability:

1. **Phenolic Hydroxyl Group**: The presence of a hydroxyl group on the phenyl ring contributes to the molecule's polarity. This can enhance hydrogen bonding with the artificial membrane, potentially increasing permeability. However, the hydroxyl group can also introduce steric hindrance, which might limit permeability depending on the orientation and accessibility of the molecule.

2. **Bromo Substituents**: The dibromo substitution on the phenyl ring increases the molecular weight and may reduce permeability due to increased steric bulk. Bromine atoms are relatively large and can hinder the molecule's ability to pass through the membrane. Additionally, the presence of bromine can enhance lipophilicity, which might balance the effect of the hydroxyl group and influence permeability.

3. **Indole Core**: The indole structure is a planar, aromatic system that can facilitate interactions with the membrane through π-π stacking. This can enhance permeability by allowing the molecule to insert itself into the lipid bilayer more effectively. The indole core is a common motif in many bioactive compounds, often associated with good membrane permeability.

4. **Methylidene Bridge**: The linkage between the phenyl and indole moieties via a methylidene bridge introduces rigidity and planarity to the molecule. This structural feature can enhance the molecule's ability to span the membrane, potentially increasing permeability.

Overall, the given molecule's permeability is likely influenced by a balance of polar and non-polar interactions, steric effects, and aromatic stacking capabilities. The presence of the hydroxyl group and bromine atoms suggests a moderate level of polarity, while the indole core and methylidene bridge contribute to a relatively planar and rigid structure. These features collectively suggest that the given molecule would exhibit high permeability in the PAMPA assay.

Final answer: High permeability

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# 5

**SMILES:** COC(=O)NC1=NC2=C(N1)C=C(C=C2)C(=O)C3=CC=CC=C3

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a benzimidazole derivative, which is a class of compounds known for their diverse biological activities. The structure of the given molecule includes a benzimidazole core, which is a bicyclic compound consisting of a benzene ring fused to an imidazole ring. This core is known for its ability to interact with various biological targets, often contributing to the molecule's pharmacological properties.

The presence of the benzoyl group attached to the benzimidazole core can enhance the lipophilicity of the molecule, which may facilitate its passage through lipid membranes. This is a common feature in many bioactive compounds, as increased lipophilicity often correlates with better membrane permeability.

Additionally, the molecule contains a carbamate group, which is a functional group derived from carbamic acid. This group can participate in hydrogen bonding, which may influence the molecule's interaction with the artificial membrane. The carbamate group can also affect the molecule's solubility and stability, potentially impacting its permeability.

Overall, the combination of the benzimidazole core, benzoyl group, and carbamate functionality suggests that the given molecule may exhibit high permeability in the PAMPA assay due to its lipophilic nature and potential for favorable interactions with the artificial membrane.

Final answer: High permeability

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# 6

**SMILES:** C[C@@]12C3=CC=CC=C3C[C@@H](N1)C4=CC=CC=C24

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex polycyclic compound with a tetracyclic structure, which includes multiple fused rings and a nitrogen atom as part of its framework. This structural complexity suggests that the molecule has a rigid and compact three-dimensional shape, which can influence its permeability.

The presence of multiple aromatic rings, as indicated by the hexaene designation, suggests that the molecule has regions of conjugated pi-electron systems. These aromatic systems can contribute to the molecule's ability to interact with the artificial membrane through pi-pi stacking or other non-covalent interactions, potentially enhancing its permeability.

The nitrogen atom in the structure introduces a basic site, which can participate in hydrogen bonding or ionic interactions with the membrane. This can also affect the molecule's solubility and permeability, as the nitrogen may interact with polar sites on the membrane.

The methyl group attached to the nitrogen atom can increase the lipophilicity of the molecule, which may enhance its ability to traverse the lipid components of the artificial membrane.

Overall, the combination of a rigid polycyclic structure, aromatic rings, and a basic nitrogen atom suggests that the given molecule may have moderate to high permeability in the PAMPA assay, as these features can facilitate interactions with the artificial membrane and enhance its ability to permeate through it.

Final answer: High permeability.

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# 7

**SMILES:** CN(CC1=CN=C2C(=N1)C(=NC(=N2)N)N)C3=CC=C(C=C3)C(=O)N[C@@H](CCC(=O)O)C(=O)O

**Label:** 0

**Predi:** 1

**Correct:** 0

# Response:
The given molecule is a derivative of folate, specifically a pteridine compound, which is structurally related to folic acid. This relationship is significant because folic acid and its derivatives are known to have good permeability across biological membranes due to their ability to mimic natural folate compounds.

The structure of the given molecule includes a pteridine ring, which is a key feature of folate derivatives. This ring system is planar and aromatic, which can facilitate interactions with lipid bilayers, enhancing permeability. Additionally, the presence of amino groups on the pteridine ring can increase the molecule's solubility and potentially its ability to form hydrogen bonds with the membrane, further aiding in permeability.

The molecule also contains a benzoyl group linked to an amino group, which can contribute to its overall lipophilicity. This lipophilic character is beneficial for membrane permeability as it allows the molecule to interact with the hydrophobic regions of the lipid bilayer.

Furthermore, the pentanedioic acid moiety, which is a dicarboxylic acid, can enhance the molecule's solubility in aqueous environments, which is important for its transport across the membrane. The presence of carboxylic acid groups can also facilitate ionic interactions with the membrane, potentially aiding in permeation.

Overall, the combination of these structural features suggests that the given molecule likely exhibits high permeability in the PAMPA assay, as it is structurally similar to folic acid and contains functional groups that enhance its interaction with lipid membranes.

Final answer: High permeability.

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# 8

**SMILES:** C1COCCN1C2=C(C=C(C=C2)C(F)(F)F)NC(=O)C3=NNC(=O)C4=CC=CC=C43

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a complex organic compound with several functional groups that influence its permeability in the PAMPA assay. Let's break down the structural features and their impact on permeability:

1. **Phenyl Ring with Morpholine Substitution**: The presence of a phenyl ring with a morpholine group attached suggests that the molecule has a degree of hydrophobicity, which can facilitate membrane permeability. The morpholine group, being a heterocyclic amine, can introduce some degree of polarity, potentially enhancing solubility and permeability through polar environments.

2. **Trifluoromethyl Group**: The trifluoromethyl group is highly electronegative and lipophilic. This group can increase the molecule's overall lipophilicity, which often enhances membrane permeability by increasing the ability of the molecule to interact with lipid bilayers. However, it can also affect the molecule's solubility, which is a crucial factor in permeability.

3. **Phthalazine Carboxamide Moiety**: The phthalazine ring system is a bicyclic aromatic structure that contributes to the rigidity and planarity of the molecule. The carboxamide group is polar and can form hydrogen bonds, which may enhance solubility and permeability through polar regions of the membrane. However, the overall effect will depend on the balance between hydrophilic and hydrophobic interactions.

4. **Oxidized Phthalazine (3-oxo)**: The presence of an oxo group (ketone) in the phthalazine ring introduces additional polarity, which can influence the molecule's interaction with the membrane. This group can participate in hydrogen bonding, potentially affecting the molecule's permeability.

Overall, the given molecule exhibits a balance of hydrophobic and hydrophilic characteristics due to its aromatic rings, trifluoromethyl group, and polar functional groups. These features suggest that the molecule may have moderate permeability in the PAMPA assay, as it can interact with both lipid and polar environments. However, the exact permeability would depend on the specific conditions of the assay and the nature of the artificial membrane used.

Final answer: Low-to-moderate permeability.

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# 9

**SMILES:** CCCCCN1C(=O)C2=C(C=C(C=C2)C(=O)NCCCN3CCCCC3)NC1=O

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a quinazoline derivative, which is a class of compounds known for their diverse biological activities. The quinazoline core is a bicyclic structure consisting of a benzene ring fused to a pyrimidine ring. This core is known for its planar structure, which can facilitate interactions with biological targets through π-π stacking and hydrogen bonding.

The presence of the carboxamide group in the given molecule suggests potential hydrogen bonding capabilities, which can enhance its interaction with biological membranes or proteins. The carboxamide group is polar, which may increase the molecule's solubility in aqueous environments, potentially aiding in its permeability across biological membranes.

The piperidine moiety, attached via a propyl linker, introduces a basic nitrogen atom into the structure. This can enhance the molecule's ability to form ionic interactions with acidic sites on biological membranes or proteins, potentially increasing its permeability. The piperidine ring is a common structural motif in many pharmaceuticals, often contributing to improved pharmacokinetic properties.

The oxo groups in the quinazoline ring contribute to the molecule's overall polarity and may participate in hydrogen bonding, further influencing its permeability. These groups can also affect the electronic distribution within the molecule, potentially impacting its interaction with biological targets.

Overall, the combination of the quinazoline core, carboxamide group, piperidine moiety, and oxo groups suggests that the given molecule may exhibit moderate to high permeability in the PAMPA assay, as these structural features are conducive to interactions with the artificial membrane.

Final answer: Low-to-moderate permeability.

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# 10

**SMILES:** CC1=C(C(=NO1)C2=CC=CC=C2)C(=O)NC3=NN=C(S3)COC4=CC=C(C=C4)Cl

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a complex organic compound that features several distinct functional groups and structural elements, each contributing to its permeability characteristics in the PAMPA assay.

1. **Aromatic Rings**: The molecule contains multiple aromatic rings, including a phenyl group and a chlorophenoxy group. Aromatic rings generally enhance lipophilicity, which can increase the molecule's ability to traverse lipid membranes. However, the presence of a chlorine atom on the phenoxy group can also introduce polar characteristics, potentially affecting the overall balance between hydrophilicity and lipophilicity.

2. **Thiadiazole Ring**: The 1,3,4-thiadiazole moiety is a heterocyclic compound that can contribute to the molecule's electronic properties. This ring can enhance the molecule's ability to interact with the artificial membrane through π-π interactions or hydrogen bonding, depending on the environment.

3. **Carboxamide Group**: The carboxamide group is a polar functional group that can form hydrogen bonds with the artificial membrane. This can increase the molecule's affinity for the membrane, potentially enhancing its permeability. However, the presence of this group may also introduce some degree of hydrophilicity, which could limit permeability if it outweighs the lipophilic characteristics.

4. **Methyl Group**: The methyl group attached to the thiadiazole ring is a small, non-polar substituent that can increase the molecule's lipophilicity, further enhancing its ability to permeate the membrane.

Overall, the given molecule's structure suggests a balance between lipophilic and hydrophilic properties. The aromatic rings and methyl group contribute to lipophilicity, while the carboxamide group introduces polar characteristics. The chlorophenoxy group adds a degree of polarity due to the chlorine atom. In the context of the PAMPA assay, these features suggest that the molecule may exhibit moderate permeability, as it has both hydrophilic and lipophilic components that can interact with the artificial membrane.

Final answer: Low-to-moderate permeability.

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# 11

**SMILES:** C1OC2=C(O1)C=C(C=C2)C3NN4C(=NN=C4S3)C5=CC=CC=C5

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex heterocyclic compound that features several distinct structural components, each contributing to its permeability characteristics in the PAMPA assay.

Firstly, the molecule contains a benzodioxole moiety, which is a bicyclic structure consisting of a benzene ring fused with a dioxole ring. This aromatic system is known for its planar structure and electron-rich nature, which can enhance the molecule's ability to interact with the hydrophobic regions of the artificial membrane. The presence of this moiety often contributes to increased permeability due to its lipophilic character.

Secondly, the molecule includes a triazolothiadiazole core. This is a fused heterocyclic system that contains both nitrogen and sulfur atoms. The presence of these heteroatoms can introduce polar characteristics, which may facilitate hydrogen bonding and other polar interactions with the membrane. However, the overall balance of hydrophobic and hydrophilic properties will determine the permeability.

Additionally, the molecule has a phenyl group attached to the triazolothiadiazole core. The phenyl group is another aromatic system that can enhance lipophilicity, potentially increasing the molecule's ability to traverse the membrane.

In summary, the given molecule's structure suggests a balance between hydrophobic and polar interactions. The benzodioxole and phenyl groups contribute to its lipophilic nature, while the triazolothiadiazole core introduces polar characteristics. These features collectively suggest that the molecule would exhibit high permeability in the PAMPA assay, as it can effectively interact with both hydrophobic and hydrophilic components of the artificial membrane.

Final answer: High permeability.

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# 12

**SMILES:** COC1=CC2=C(C=C1)NC(=O)C(=C2)C3=NOC(=N3)C4=CC=CC=C4

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several distinct functional groups and structural motifs, each contributing to its permeability characteristics in the PAMPA assay.

Firstly, the molecule contains a quinoline moiety, which is a bicyclic structure consisting of a benzene ring fused to a pyridine ring. Quinoline derivatives are known for their ability to interact with biological membranes due to their planar aromatic structure, which can facilitate passage through lipid bilayers. This aromaticity can enhance the molecule's ability to permeate the artificial membrane, contributing to its classification as having high permeability.

Additionally, the molecule includes a methoxy group attached to the quinoline ring. Methoxy groups are electron-donating and can increase the lipophilicity of the molecule, further enhancing its ability to permeate lipid membranes. This functional group can also influence the electronic properties of the quinoline ring, potentially affecting its interaction with the artificial membrane.

The molecule also features a 1,2,4-oxadiazole ring, which is a five-membered heterocyclic ring containing nitrogen and oxygen atoms. This ring can contribute to the molecule's overall polarity and hydrogen bonding capabilities, which may affect its permeability. However, the presence of this heterocyclic ring is likely balanced by the lipophilic nature of the quinoline and phenyl groups, resulting in a net increase in permeability.

The phenyl group attached to the oxadiazole ring adds to the molecule's hydrophobic character, which can enhance its ability to interact with the hydrophobic regions of the artificial membrane. This group can also contribute to the overall stability of the molecule within the membrane environment.

In summary, the given molecule's combination of aromatic, lipophilic, and heterocyclic features suggests that it would exhibit high permeability in the PAMPA assay, allowing it to effectively traverse the artificial membrane.

Final answer: High permeability.

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# 13

**SMILES:** CC1=CC=CC=C1C2=NC(=C(O2)C)CN3CCC(CC3)C(=O)NCCCN4CCOCC4

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a complex organic compound that includes several functional groups and structural features that influence its permeability in the PAMPA assay. Let's break down these features and their impact on permeability:

1. **1,3-Oxazole Ring**: The presence of the 1,3-oxazole ring, which is a five-membered heterocyclic compound containing both nitrogen and oxygen, contributes to the molecule's polarity and potential hydrogen bonding capabilities. This can enhance the molecule's solubility in aqueous environments, which is beneficial for permeability through the PAMPA membrane, a model for biological membranes.

2. **Dimethyl Substitution**: The dimethyl groups on the oxazole ring increase the hydrophobic character of the molecule. While hydrophobic interactions can be favorable for membrane permeability, the balance between hydrophilic and hydrophobic properties is crucial. In this case, the oxazole ring's polar nature may dominate, suggesting moderate permeability.

3. **Phenyl Group**: The phenyl group attached to the oxazole ring adds to the hydrophobic character of the molecule. Aromatic rings can participate in π-π interactions with the membrane, potentially aiding in permeability. However, the presence of the polar oxazole ring may counterbalance this, leading to a moderate permeability profile.

4. **Morpholine Ring**: The morpholine ring is a six-membered heterocycle containing both nitrogen and oxygen, which can enhance the molecule's solubility and ability to form hydrogen bonds. This feature is likely to increase the molecule's permeability, as it can interact favorably with the polar components of the PAMPA membrane.

5. **Piperidine Ring**: The piperidine ring is a saturated six-membered nitrogen-containing ring, which can contribute to the basicity and overall polarity of the molecule. This can enhance the molecule's ability to interact with the PAMPA membrane, potentially increasing permeability.

6. **Carboxamide Group**: The carboxamide group is a polar functional group that can form hydrogen bonds, which may enhance the molecule's solubility and permeability. However, its presence also adds to the overall polarity, which might reduce permeability due to increased interaction with the aqueous environment.

Overall, the given molecule's structure suggests a balance between hydrophilic and hydrophobic properties. The presence of polar functional groups like the oxazole, morpholine, and carboxamide rings, along with hydrophobic aromatic and alkyl groups, indicates that the molecule likely exhibits moderate permeability in the PAMPA assay. The interplay of these features allows the molecule to interact with the membrane, but not so extensively that it would be classified as having high permeability.

Final answer: Low-to-moderate permeability.

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# 14

**SMILES:** C1=CC(=CN=C1)NC(=O)C2=CC=CS2

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is an aromatic amide, which consists of a thiophene ring and a pyridine ring connected through an amide linkage. The thiophene ring is a five-membered heteroaromatic ring containing sulfur, while the pyridine ring is a six-membered heteroaromatic ring containing nitrogen.

The presence of these aromatic rings contributes to the molecule's overall planarity and rigidity, which can enhance its ability to interact with the artificial membrane. The aromatic nature of the rings allows for π-π stacking interactions, which can facilitate the passage of the molecule through the membrane.

The amide linkage in the molecule provides a polar functional group, which can form hydrogen bonds with the membrane. This can increase the molecule's solubility in the membrane's environment and enhance its permeability.

Overall, the combination of aromatic rings and the amide linkage suggests that the given molecule would have moderate to high permeability in the artificial membrane, as the aromatic rings promote membrane interaction and the amide linkage facilitates solubility and hydrogen bonding.

Final answer: High permeability

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# 15

**SMILES:** CC1=CC=CC=C1NC(=O)NC2=CC=CS2

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a member of the urea class, characterized by the presence of a urea functional group, which is a carbonyl group flanked by two nitrogen atoms. This functional group is known for its ability to form hydrogen bonds, which can influence the molecule's solubility and permeability.

The structure of the given molecule includes a 2-methylphenyl group and a thiophen-2-yl group attached to the urea moiety. The 2-methylphenyl group is a phenyl ring with a methyl substituent, which can increase the hydrophobic character of the molecule. This hydrophobicity can affect the molecule's ability to permeate through the lipid-rich environment of a biological membrane.

The thiophen-2-yl group is a five-membered aromatic ring containing sulfur, which can contribute to the molecule's overall electronic properties. The presence of this heteroaromatic ring can enhance the molecule's ability to interact with the artificial membrane through π-π interactions or other non-covalent interactions.

In the context of the Parallel Artificial Membrane Permeability Assay (PAMPA), the given molecule's permeability is influenced by the balance between its hydrophilic urea group and its hydrophobic aromatic rings. The urea group can facilitate interactions with the aqueous environment, while the aromatic rings can interact with the lipid components of the membrane. Overall, the given molecule is likely to exhibit moderate permeability due to the presence of both hydrophilic and hydrophobic components, which can enable it to traverse the artificial membrane while still being subject to some resistance from the lipid barrier.

Final answer: Low-to-moderate permeability.

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# 16

**SMILES:** C1=NC2=C(N1)C(=O)NC=N2

**Label:** 0

**Predi:** 1

**Correct:** 0

# Response:
The given molecule is a derivative of hypoxanthine, which is a purine base. The structure of the given molecule includes a purine ring system with a keto group at a specific position. This modification from hypoxanthine introduces a carbonyl group, making it a 7-oxo derivative.

The presence of the carbonyl group at the 7-position of the purine ring is significant in determining the molecule's permeability. The carbonyl group is a polar functional group, which can form hydrogen bonds with the artificial membrane. This interaction can enhance the molecule's ability to permeate the membrane, as the polar group can interact with the polar components of the membrane.

Additionally, the purine ring system is a planar, aromatic structure, which can facilitate interactions with the membrane through π-π stacking or van der Waals forces. The aromatic nature of the purine ring can also contribute to the molecule's ability to permeate the membrane by allowing it to fit into hydrophobic pockets within the membrane.

Overall, the combination of the polar carbonyl group and the aromatic purine ring suggests that the given molecule would have high permeability in the Parallel Artificial Membrane Permeability Assay (PAMPA).

Final answer: High permeability

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# 17

**SMILES:** CC1=CC=C(C=C1)N2C3=NC=NC(=C3C=N2)NC4=CC=CC(=C4)C(=O)O

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several functional groups and structural elements that influence its permeability in the PAMPA assay. Let's break down these features and their impact on permeability:

1. **Aromatic Rings**: The molecule contains multiple aromatic rings, including a pyrazolo[3,4-d]pyrimidine moiety and a benzoic acid group. Aromatic rings are generally hydrophobic, which can enhance the molecule's ability to interact with the hydrophobic regions of the artificial membrane. This interaction can facilitate the passage of the molecule through the membrane, contributing to high permeability.

2. **Pyrazolo[3,4-d]pyrimidine Moiety**: This heterocyclic structure is known for its planar and aromatic nature, which can further enhance the molecule's ability to permeate through the membrane. The presence of nitrogen atoms in the pyrazole and pyrimidine rings can also participate in hydrogen bonding, which may aid in the molecule's interaction with the membrane.

3. **Amino Group**: The amino group attached to the pyrazolo[3,4-d]pyrimidine moiety can form hydrogen bonds with the membrane, potentially increasing the molecule's solubility and permeability. This functional group can also act as a site for protonation, which may influence the molecule's overall charge and interaction with the membrane.

4. **Methylphenyl Substituent**: The presence of a methyl group on the phenyl ring can increase the lipophilicity of the molecule, enhancing its ability to permeate through the lipid-rich regions of the artificial membrane.

5. **Carboxylic Acid Group**: The benzoic acid group introduces a polar and acidic functional group, which can form ionic interactions with the membrane. However, the carboxylic acid group can also lead to a decrease in permeability due to its hydrophilic nature, which may hinder the molecule's passage through the membrane.

Overall, the given molecule's structure suggests that it has a balance of hydrophobic and hydrophilic properties, with multiple aromatic rings and functional groups that can interact with the artificial membrane. This balance likely results in high permeability, as the molecule can effectively navigate through the membrane while maintaining sufficient solubility and interaction with the membrane components.

Final answer: High permeability.

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# 18

**SMILES:** CCN(CC)CCNC(=O)C1CCN(CC1)C2=NN3C=C(N=C3S2)C4=CC=C(C=C4)F

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex structure that includes several functional groups and structural features that influence its permeability in the PAMPA assay. Let's break down these features and their impact on permeability:

1. **Piperidine Ring**: The presence of a piperidine ring, which is a six-membered nitrogen-containing heterocycle, contributes to the molecule's basicity and hydrophilicity. Piperidine rings are often found in pharmacologically active compounds and can enhance the molecule's ability to interact with biological membranes. This feature is likely to increase the permeability of the given molecule.

2. **Carboxamide Group**: The carboxamide group is a polar functional group that can form hydrogen bonds with the artificial membrane. This interaction can enhance the molecule's permeability by stabilizing its interaction with the membrane.

3. **Diethylamino Group**: The diethylamino moiety is a basic group that can increase the solubility of the molecule in aqueous environments. This group can also participate in ionic interactions with the membrane, potentially enhancing permeability.

4. **Fluorophenyl Group**: The presence of a fluorophenyl group introduces a hydrophobic character to the molecule. Fluorine atoms can enhance the lipophilicity of the molecule, which may facilitate its passage through the lipid bilayer of the artificial membrane.

5. **Imidazo[2,1-b][1,3]thiazole Moiety**: This bicyclic structure is a heteroaromatic system that can contribute to the molecule's overall stability and rigidity. The presence of nitrogen and sulfur atoms in this moiety can also influence the electronic properties of the molecule, potentially affecting its interaction with the membrane.

Overall, the given molecule exhibits a combination of hydrophilic and hydrophobic properties, as well as the ability to form hydrogen bonds and ionic interactions. These features suggest that the molecule would have high permeability in the PAMPA assay, as it can effectively interact with and traverse the artificial membrane.

Final answer: High permeability

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# 19

**SMILES:** CC1=CC2=C(C=C1)C(=C(N2CC3=CC=C(C=C3)OC)C(=O)O)CNCC4=CC=CO4

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several functional groups and structural elements that influence its permeability in the PAMPA assay. Let's break down these features and their impact on permeability:

1. **Indole Core**: The presence of an indole core is significant as it is a planar, aromatic structure that can facilitate interactions with the artificial membrane. Indole rings are known for their ability to participate in π-π stacking interactions, which can enhance the molecule's ability to permeate the membrane.

2. **Methoxyphenyl Group**: The methoxyphenyl group is an aromatic ring with a methoxy substituent. The methoxy group is an electron-donating group, which can increase the electron density of the aromatic ring. This can enhance the molecule's lipophilicity, potentially improving its ability to permeate the lipid-like environment of the artificial membrane.

3. **Furan-2-ylmethyl Group**: The furan ring is another aromatic heterocycle that contributes to the molecule's overall aromaticity and lipophilicity. The presence of this group can enhance the molecule's ability to interact with the membrane through π-π interactions and may also contribute to its solubility in organic solvents.

4. **Methylamino Group**: The methylamino group introduces a basic nitrogen atom, which can form hydrogen bonds with the artificial membrane. This group can also enhance the molecule's solubility in water, which is important for its interaction with the membrane.

5. **Carboxylic Acid Group**: The carboxylic acid group is a polar functional group that can form hydrogen bonds and ionic interactions with the membrane. This group can also affect the molecule's overall solubility and permeability by providing a site for interaction with the membrane's polar head groups.

Overall, the given molecule has a combination of aromatic and polar functional groups that suggest it would have moderate to high permeability in the PAMPA assay. The balance of lipophilic and hydrophilic properties, along with the ability to form various non-covalent interactions, supports its potential to permeate the artificial membrane effectively.

Final answer: High permeability

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# 20

**SMILES:** CC(=O)C1=CC=C(C=C1)N2CCN(CC2)C3=C(C=C(C=C3)NC(=O)C4=CC=C(C=C4)F)C(=O)O

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a complex organic compound that features several functional groups and structural elements that influence its permeability in the PAMPA assay. Let's break down the key components and their impact on permeability:

1. **Piperazine Ring**: The presence of a piperazine ring, which is a six-membered heterocyclic compound containing two nitrogen atoms, is a significant feature. Piperazine rings are known for their ability to enhance the solubility and permeability of molecules. The nitrogen atoms can participate in hydrogen bonding, which can facilitate the interaction of the molecule with the artificial membrane.

2. **Aromatic Rings**: The given molecule contains multiple aromatic rings, including phenyl groups and a fluorobenzoyl moiety. Aromatic rings can enhance lipophilicity, which is often associated with increased membrane permeability. However, the presence of these rings can also lead to steric hindrance, which might reduce permeability depending on the size and orientation of the molecule.

3. **Fluorobenzoyl Group**: The fluorine atom in the fluorobenzoyl group can increase the lipophilicity of the molecule, potentially enhancing its ability to permeate the membrane. Fluorine is also known to influence the electronic properties of aromatic rings, which can affect the molecule's interaction with the membrane.

4. **Acetyl Group**: The acetyl group attached to one of the phenyl rings can increase the molecule's polarity, which might enhance its solubility in aqueous environments. This could facilitate the molecule's interaction with the polar head groups of the artificial membrane.

5. **Carboxylic Acid Group**: The carboxylic acid group is a polar functional group that can form hydrogen bonds with the membrane. This group can also ionize under physiological conditions, which may enhance the molecule's solubility and permeability.

Overall, the given molecule's structure suggests that it has a balance of hydrophilic and lipophilic properties, which is typical for molecules with moderate permeability in PAMPA assays. The presence of aromatic rings and functional groups like piperazine and carboxylic acid contribute to its ability to interact with the artificial membrane, while the fluorobenzoyl and acetyl groups may enhance its lipophilicity and solubility. Therefore, the given molecule is likely to exhibit moderate permeability in the PAMPA assay.

Final answer: Low-to-moderate permeability.

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# 21

**SMILES:** C1CCN(CC1)C2CCN(CC2)C3=C(C=C(C=C3)NC(=O)C4=CC=C(C=C4)Br)C(=O)O

**Label:** 0

**Predi:** 0

**Correct:** 1

# Response:
The given molecule is a complex organic compound with several functional groups and structural features that influence its permeability in the PAMPA assay. Let's break down these features and their impact on permeability:

1. **Aromatic Rings**: The molecule contains multiple aromatic rings, including a bromobenzoyl group and a phenyl group. Aromatic rings can enhance lipophilicity, which generally increases membrane permeability. However, the presence of a bromine atom in the bromobenzoyl group can introduce steric hindrance and electron-withdrawing effects, which might slightly reduce permeability compared to a simple aromatic ring.

2. **Amide Linkage**: The molecule features an amide linkage, which is a common functional group in many bioactive compounds. Amides can form hydrogen bonds with the artificial membrane, potentially increasing permeability. However, the presence of the amide group also introduces some rigidity and polarity, which can affect the overall permeability.

3. **Piperazine Ring**: The piperazine moiety is a flexible, nitrogen-containing heterocycle that can enhance solubility and permeability due to its basic nature. The presence of this ring can facilitate interactions with the membrane and improve permeability.

4. **Carboxylic Acid Group**: The carboxylic acid group is a polar and hydrophilic functional group. It can form hydrogen bonds and ionic interactions with the membrane, which may enhance permeability. However, the acidic nature of this group can also lead to ionization, which might reduce permeability by increasing hydrophilicity.

Overall, the given molecule has a balance of lipophilic and hydrophilic properties due to its aromatic rings, amide linkage, piperazine ring, and carboxylic acid group. These features suggest that the molecule would have moderate permeability in the PAMPA assay, as the lipophilic aromatic rings and piperazine ring promote permeability, while the polar carboxylic acid group and amide linkage provide some hydrophilic character.

Final answer: Low-to-moderate permeability.

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# 22

**SMILES:** CC1=C(C=C(C=C1)C2=NN3C(=NN=C3C4=CC=CC=C42)C)S(=O)(=O)NC

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a member of the quinazoline family, which is known for its diverse biological activities. The structure of the given molecule includes several key features that influence its permeability in the PAMPA assay.

Firstly, the quinazoline core is a bicyclic structure that is relatively planar and aromatic. This aromaticity can enhance the molecule's ability to interact with the artificial membrane through π-π stacking interactions, which are common in planar aromatic systems. Such interactions can facilitate the passage of the molecule through the membrane.

Additionally, the presence of a sulfonamide group in the given molecule is significant. Sulfonamides are known for their ability to form hydrogen bonds, which can enhance the molecule's solubility and permeability. The sulfonamide group can interact with the polar head groups of the artificial membrane, potentially increasing the molecule's ability to permeate the membrane.

The methyl groups attached to the phenyl and quinazoline rings can also play a role in the molecule's permeability. These alkyl groups can increase the lipophilicity of the molecule, which may enhance its ability to traverse the lipid-rich environment of the artificial membrane.

Overall, the combination of aromaticity, hydrogen bonding potential, and lipophilicity in the given molecule suggests that it would exhibit high permeability in the PAMPA assay.

Final answer: High permeability

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# 23

**SMILES:** C1=C(OC(=C1)[N+](=O)[O-])C=NNC(=O)C(=O)N

**Label:** 0

**Predi:** 0

**Correct:** 1

# Response:
The given molecule is a member of furans, which are heterocyclic compounds containing a five-membered aromatic ring with one oxygen atom. The presence of the furan ring contributes to the molecule's aromaticity and potential for interactions with biological membranes.

The molecule also contains a nitrofuran moiety, which is a furan ring substituted with a nitro group. The nitro group is an electron-withdrawing group, which can influence the molecule's electronic properties and potentially its reactivity. This group can also participate in hydrogen bonding and other polar interactions, which may affect the molecule's permeability.

Additionally, the molecule features an acetohydrazide group, which includes both an amide and a hydrazide linkage. These functional groups can form hydrogen bonds, which are crucial for interactions with the artificial membrane. The presence of these groups can enhance the molecule's solubility and permeability by facilitating interactions with the membrane's polar head groups.

Overall, the combination of the aromatic furan ring, the electron-withdrawing nitro group, and the hydrogen-bonding potential of the acetohydrazide group suggests that the given molecule may exhibit moderate permeability in the PAMPA assay. The balance of hydrophobic and hydrophilic interactions allows it to traverse the artificial membrane, but the specific permeability will depend on the exact nature of these interactions and the membrane's properties.

Final answer: Low-to-moderate permeability.

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# 24

**SMILES:** C1COCCN1C2=CC(=O)C3=C(O2)C4=CC=CC=C4C=C3

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex heterocyclic compound that includes a morpholine ring and a benzo[h]chromenone structure. The morpholine ring is a six-membered ring containing both oxygen and nitrogen, which can contribute to the molecule's solubility and potential hydrogen bonding interactions. This can enhance the molecule's ability to interact with the artificial membrane, potentially increasing its permeability.

The benzo[h]chromenone structure is a fused aromatic system that can contribute to the molecule's lipophilicity. This lipophilic character can facilitate the passage of the molecule through the lipid-like environment of the artificial membrane, promoting permeability.

Overall, the combination of the morpholine ring's polar characteristics and the aromatic system's lipophilicity suggests that the given molecule may exhibit high permeability in the PAMPA assay.

Final answer: High permeability.

------
# 25

**SMILES:** CN1C(=NN=N1)SC2=NC=NC3=C2C=CS3

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a thienopyrimidine derivative, which is characterized by a fused bicyclic structure consisting of a thiophene ring and a pyrimidine ring. This core structure is known for its potential biological activity and is often used in pharmaceuticals.

The molecule also features a tetrazole ring, which is a five-membered ring containing four nitrogen atoms. The tetrazole is connected to the thienopyrimidine core via a sulfanyl (thioether) linkage. The presence of the tetrazole ring is significant because it can enhance the molecule's ability to form hydrogen bonds and ionic interactions, which can improve its solubility and permeability.

The sulfanyl linkage introduces a degree of flexibility and lipophilicity to the molecule. Sulfanyl groups are known to enhance membrane permeability due to their ability to interact with lipid bilayers, which can facilitate the passage of the molecule through biological membranes.

Overall, the combination of the thienopyrimidine core, the tetrazole ring, and the sulfanyl linkage suggests that the given molecule is likely to exhibit high permeability in the PAMPA assay. This is because these structural features can enhance the molecule's ability to interact with the artificial membrane, promoting its passage through the membrane.

Final answer: High permeability.

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# 26

**SMILES:** C1=CC=C(C=C1)NC(=O)CCCCCCC(=O)NO

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a derivative of a linear diamide, specifically a heptanediamide, which means it has a seven-carbon aliphatic chain with two amide groups. The presence of the heptanediamide backbone suggests that the molecule is relatively flexible and has a moderate hydrophobic character due to the aliphatic chain.

The molecule also contains a hydroxyamino group attached to the aliphatic chain. This functional group introduces a polar character to the molecule, which can enhance its solubility in aqueous environments and potentially increase its ability to form hydrogen bonds with the artificial membrane.

Additionally, the molecule features an N-phenyl group, which is a phenyl ring attached to one of the nitrogen atoms of the amide. This aromatic group can contribute to the molecule's overall hydrophobicity and may facilitate π-π interactions with the artificial membrane, which is composed of lipophilic and hydrophilic regions.

Considering these structural features, the given molecule is likely to exhibit a balance of hydrophobic and hydrophilic interactions with the artificial membrane. The hydroxyamino group can enhance solubility and hydrogen bonding, while the N-phenyl group and the aliphatic chain contribute to hydrophobic interactions. Therefore, the molecule is expected to have moderate permeability through the artificial membrane, as it can interact with both hydrophilic and hydrophobic components of the membrane.

Final answer: Low-to-moderate permeability.

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# 27

**SMILES:** CN(C)C1=CC=C(C=C1)C2=C(C(=O)NC=C2)N

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a derivative of a 2-pyridinone, which is a heterocyclic compound containing a pyridine ring with a ketone group. The presence of the pyridinone structure suggests that the molecule may have some degree of polarity due to the carbonyl group, which can participate in hydrogen bonding and dipole-dipole interactions. This can influence its permeability across biological membranes.

The molecule also features an amino group attached to the pyridinone ring. Amino groups are known to be polar and can enhance the solubility of the molecule in aqueous environments, which is beneficial for permeability through biological membranes.

Additionally, the molecule contains a dimethylamino-substituted phenyl group. The dimethylamino group is a tertiary amine, which is relatively non-polar compared to primary or secondary amines. However, it can still contribute to the overall polarity of the molecule due to its ability to participate in hydrogen bonding and ionic interactions.

The combination of these functional groups suggests that the given molecule may have moderate permeability in the PAMPA assay. The pyridinone and amino groups can enhance solubility and interaction with the membrane, while the dimethylamino group may provide some balance by reducing overall polarity. This balance of polar and non-polar characteristics is likely to result in moderate permeability, as the molecule can interact with the membrane but may not be highly lipophilic.

Final answer: Low-to-moderate permeability.

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# 28

**SMILES:** COC1=C(C=C(C=C1)C2=CSC(=N2)N3CCC(CC3)C(=O)N)OC

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a piperidinecarboxamide, which is characterized by the presence of a piperidine ring attached to a carboxamide group. This structural feature is significant in determining the molecule's permeability.

The piperidine ring is a six-membered nitrogen-containing heterocycle, which is known for its basicity and ability to form hydrogen bonds. This can enhance the molecule's solubility and interaction with biological membranes, potentially increasing its permeability.

The carboxamide group is a functional group that can also participate in hydrogen bonding, which may further facilitate the molecule's interaction with the artificial membrane. This group can act as both a hydrogen bond donor and acceptor, which is beneficial for permeability.

Additionally, the molecule contains a thiazole ring, which is a five-membered heterocyclic compound containing both sulfur and nitrogen. The presence of this ring can contribute to the molecule's overall stability and lipophilicity, which may affect its permeability.

The dimethoxyphenyl group is a phenyl ring substituted with two methoxy groups. These methoxy groups are electron-donating, which can increase the lipophilicity of the molecule. This increased lipophilicity can enhance the molecule's ability to permeate through the lipid-rich environment of the artificial membrane.

Overall, the combination of these functional groups suggests that the given molecule likely has high permeability in the Parallel Artificial Membrane Permeability Assay (PAMPA), as it possesses features that promote solubility, stability, and lipophilicity, which are all favorable for membrane permeation.

Final answer: High permeability.

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# 29

**SMILES:** COC1=CC(=CC(=C1OC)OC)C2=CSC(=N2)N3CCC(CC3)C(=O)N

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a piperidinecarboxamide, which is characterized by the presence of a piperidine ring attached to a carboxamide group. This structural feature is significant in determining the molecule's permeability.

The piperidine ring is a six-membered nitrogen-containing heterocycle, which is known for its basicity and ability to form hydrogen bonds. This can enhance the molecule's solubility and interaction with biological membranes, potentially increasing its permeability.

The carboxamide group is a functional group that can also participate in hydrogen bonding, which may further influence the molecule's interaction with the artificial membrane. This group can contribute to the molecule's overall polarity, which is an important factor in determining its permeability.

Additionally, the molecule contains a thiazole ring, which is a five-membered heterocycle containing both sulfur and nitrogen. The presence of this ring can impact the molecule's electronic properties and its ability to interact with the membrane.

The trimethoxyphenyl group is a phenyl ring substituted with three methoxy groups. These methoxy groups are electron-donating and can increase the lipophilicity of the molecule. This increased lipophilicity can enhance the molecule's ability to permeate through the lipid components of the artificial membrane.

Overall, the combination of these structural features suggests that the given molecule may have moderate to high permeability in the PAMPA assay, as the balance of hydrophilic and lipophilic properties allows it to interact effectively with the artificial membrane.

Final answer: High permeability.

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# 30

**SMILES:** CC(=O)NC1CCN(CC1)C2=NC(=CS2)C3=CC=C(C=C3)Br

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a piperidine derivative, which is a class of compounds known for their ability to interact with various biological targets due to their structural flexibility and basic nitrogen atom. The presence of the piperidine ring contributes to the molecule's ability to permeate biological membranes, as it can enhance lipophilicity and facilitate passage through lipid bilayers.

The thiazole ring in the given molecule is a heterocyclic compound containing both sulfur and nitrogen atoms. This ring can participate in hydrogen bonding and π-π interactions, which may influence the molecule's binding affinity and permeability. The thiazole ring can also contribute to the overall stability and rigidity of the molecule, potentially affecting its ability to permeate the artificial membrane.

The 4-bromophenyl group is a hydrophobic aromatic ring with a bromine substituent. The presence of the bromine atom increases the molecule's lipophilicity, which can enhance its permeability through the lipid-rich environment of the artificial membrane. However, the bromine atom can also introduce steric hindrance, which might affect the molecule's interaction with the membrane.

Overall, the combination of the piperidine ring, thiazole ring, and 4-bromophenyl group suggests that the given molecule has a balance of hydrophilic and hydrophobic properties, which is likely to result in moderate permeability through the artificial membrane. The presence of these functional groups indicates that the molecule may have a moderate ability to permeate the membrane, making it neither highly permeable nor completely impermeable.

Final answer: Low-to-moderate permeability.

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# 31

**SMILES:** CC1=NC(=CC=C1)C2=C(N=C(N2)C(C)(C)C)C3=CC4=NC=CN=C4C=C3

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a quinoxaline derivative, which is a class of compounds known for their diverse biological activities. The structure of the given molecule includes a quinoxaline core, which is a bicyclic compound consisting of a benzene ring fused to a pyrazine ring. This core is known for its planar structure, which can facilitate interactions with biological membranes.

The molecule also features a pyridine ring substituted with a methyl group, which can enhance lipophilicity and potentially improve membrane permeability. The presence of the pyridine ring can contribute to hydrogen bonding and π-π interactions, which are important for binding to biological targets.

Additionally, the molecule contains a tert-butyl group attached to a pyrazole ring. The tert-butyl group is a bulky, hydrophobic moiety that can increase the lipophilicity of the molecule, enhancing its ability to permeate lipid membranes. The pyrazole ring itself is a five-membered heterocycle that can participate in hydrogen bonding and other non-covalent interactions.

Overall, the combination of these structural features suggests that the given molecule may have high permeability to the artificial membrane due to its lipophilic and planar characteristics, which are conducive to crossing lipid bilayers.

Final answer: High permeability.

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# 32

**SMILES:** C1=CC(=CC(=C1)N2C=CC=C2/C=C/3\C(=O)N(C(=O)N3)C4=CC(=CC=C4)Cl)C(=O)O

**Label:** 0

**Predi:** 1

**Correct:** 0

# Response:
The given molecule is a complex organic compound that includes several functional groups and structural features that influence its permeability in the PAMPA assay. Let's break down these features and their impact on permeability:

1. **Benzoic Acid Moiety**: The presence of a benzoic acid group contributes to the molecule's polarity and potential hydrogen bonding capabilities. This functional group can enhance the molecule's solubility in aqueous environments, which is beneficial for permeability through the PAMPA membrane, a model that mimics biological membranes.

2. **Pyridine Ring**: The pyridine ring, which is chlorinated in this case, adds aromaticity and potential for π-π interactions with the membrane. The chlorine substituent can also influence the electronic properties of the pyridine ring, potentially affecting the molecule's overall lipophilicity and interaction with the membrane.

3. **Imidazolidine Dione Structure**: This part of the molecule contains two carbonyl groups, which can participate in hydrogen bonding and dipole-dipole interactions. The imidazolidine dione structure is relatively polar, which may enhance the molecule's ability to interact with the polar head groups of the artificial membrane.

4. **Conjugated System**: The conjugated system formed by the pyridine, imidazolidine dione, and benzoic acid moieties can contribute to the molecule's overall stability and rigidity. This conjugation can also affect the electronic distribution across the molecule, influencing its interaction with the membrane.

5. **Methine Linkage**: The methine linkage between the pyridine and imidazolidine dione structures introduces a degree of flexibility, which can impact the molecule's ability to fit into the membrane's structure.

Overall, the given molecule's combination of polar and aromatic features, along with its ability to form hydrogen bonds and participate in π-π interactions, suggests that it would have moderate to high permeability in the PAMPA assay. The balance of hydrophilic and hydrophobic properties allows it to interact effectively with the artificial membrane, facilitating its passage through the model system.

Final answer: High permeability

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# 33

**SMILES:** CC1(CCC(=C(C1)CN2CCN(CC2)C3=CC=C(C=C3)C(=O)NS(=O)(=O)C4=CC(=C(C=C4)N[C@H](CCN5CCOCC5)CSC6=CC=CC=C6)S(=O)(=O)C(F)(F)F)C7=CC=C(C=C7)Cl)C

**Label:** 0

**Predi:** 1

**Correct:** 0

# Response:
The given molecule is a complex organic compound with several functional groups and structural features that influence its permeability in the PAMPA assay. Let's break down these features and their potential impact on permeability:

1. **Aromatic Rings**: The molecule contains multiple aromatic rings, including phenyl and chlorophenyl groups. Aromatic rings can enhance lipophilicity, which generally increases membrane permeability. However, the presence of a chlorine atom on the phenyl ring can also introduce polar characteristics, potentially affecting the overall balance between hydrophilicity and lipophilicity.

2. **Sulfonamide Group**: The presence of a sulfonamide group is significant as it can form hydrogen bonds with the artificial membrane, potentially increasing permeability. Sulfonamides are known for their ability to interact with biological membranes due to their polar nature.

3. **Piperidine Ring**: The piperidine moiety contributes to the molecule's basicity and can enhance solubility in aqueous environments. This can facilitate interaction with the artificial membrane, potentially increasing permeability.

4. **Thioether Linkage**: The thioether linkage (sulfur atom connecting two carbon atoms) can contribute to the lipophilicity of the molecule, which may enhance permeability. However, sulfur can also introduce some degree of polarity, which might affect the balance between hydrophilic and lipophilic properties.

5. **Amide Linkages**: The molecule contains multiple amide linkages, which are polar and can form hydrogen bonds. These linkages can enhance solubility and interaction with the membrane, potentially increasing permeability.

6. **Dihydrobenzothiazole Moiety**: This moiety is relatively large and complex, contributing to the overall molecular size and shape. While it may affect the molecule's ability to fit into the membrane, it can also enhance lipophilicity, which might favor permeability.

Overall, the given molecule has a combination of lipophilic and hydrophilic characteristics due to its aromatic rings, sulfonamide group, piperidine ring, and amide linkages. These features suggest that the molecule may have moderate to high permeability in the PAMPA assay, as it can interact with the artificial membrane through a combination of hydrophobic interactions and hydrogen bonding.

Final answer: High permeability

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# 34

**SMILES:** CCCCCCCCC1=CC=C(C=C1)CCC(CO)(CO)N

**Label:** 0

**Predi:** 1

**Correct:** 0

# Response:
The given molecule is a PAMPA molecule with a structure that includes a long hydrophobic octyl chain attached to a phenyl group, as well as amino and diol functional groups. 

The presence of the octyl chain contributes to the hydrophobic character of the molecule, which can enhance its ability to interact with the lipid components of the artificial membrane. This hydrophobic interaction is crucial for permeability, as it allows the molecule to embed itself within the lipid bilayer, facilitating its passage through the membrane.

The phenyl group, which is part of the aromatic system, can also participate in hydrophobic interactions and may contribute to the molecule's ability to traverse the membrane. Additionally, the phenyl group can engage in π-π interactions with other aromatic systems in the membrane, potentially aiding in membrane permeability.

The amino group introduces a polar character to the molecule, which can form hydrogen bonds with the polar head groups of the artificial membrane. This interaction can enhance the molecule's solubility in the membrane environment and promote its permeability.

The two hydroxyl groups (diol) further increase the molecule's polarity and ability to form hydrogen bonds. These groups can interact with the polar head groups of the artificial membrane, enhancing the molecule's solubility and permeability.

Overall, the combination of hydrophobic and polar interactions in the given molecule suggests that it would have high permeability in the artificial membrane, as it can effectively interact with both the lipid and polar components of the membrane.

Final answer: High permeability.

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# 35

**SMILES:** CN(C)[C@@H]1CCN(C1)C2=CC=CC(=C2)NC3=NN4C(=O)C5=CC=CC=C5N=C4S3

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several distinct structural components, each contributing to its permeability characteristics in the PAMPA assay.

1. **Pyrrolidine Ring**: The presence of a dimethylamino group attached to a pyrrolidine ring indicates that the molecule has basic properties. This basicity can enhance the molecule's solubility in water, which is a favorable property for permeability through biological membranes. The pyrrolidine ring also provides a degree of rigidity and structural stability, which can influence the molecule's interaction with the artificial membrane.

2. **Phenyl Group**: The phenyl group attached to the pyrrolidine ring is a hydrophobic moiety. This hydrophobic character can facilitate the molecule's passage through lipid membranes, as it can interact with the hydrophobic regions of the artificial membrane. However, the presence of the phenyl group may also introduce steric hindrance, which could affect the molecule's overall permeability.

3. **Quinazolinone Core**: The quinazolinone structure is a bicyclic system that contributes to the molecule's overall planarity and rigidity. This core is known for its ability to participate in hydrogen bonding and π-π interactions, which can enhance binding to the artificial membrane. The presence of nitrogen and oxygen atoms in the quinazolinone core can also contribute to hydrogen bonding, potentially increasing the molecule's affinity for the membrane.

4. **Thiazole Ring**: The thiazole ring is a heterocyclic compound that can enhance the molecule's electronic properties. The sulfur and nitrogen atoms in the thiazole ring can participate in various non-covalent interactions, such as hydrogen bonding and dipole-dipole interactions, which may facilitate the molecule's interaction with the artificial membrane.

Overall, the given molecule's combination of hydrophilic and hydrophobic regions, along with its ability to participate in various non-covalent interactions, suggests that it would exhibit high permeability in the PAMPA assay. The balance of these structural features allows the molecule to effectively navigate the artificial membrane, making it suitable for further pharmacokinetic studies.

Final answer: High permeability

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# 36

**SMILES:** CCNC(=O)C1=CC=C(O1)C2=CC3=C(C=C2)N=CN=C3NCC4CCCO4

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that includes several distinct structural features contributing to its permeability characteristics in the PAMPA assay.

1. **Quinazoline Core**: The presence of the quinazoline moiety is significant. Quinazolines are known for their planar aromatic structure, which can facilitate interactions with the artificial membrane. This planar structure can enhance the molecule's ability to intercalate or insert itself into the lipid bilayer, potentially increasing permeability.

2. **Furan Carboxamide Group**: The furan ring is a five-membered aromatic heterocycle, which can contribute to the molecule's overall lipophilicity. The carboxamide group attached to the furan ring can form hydrogen bonds, which may aid in the molecule's interaction with the membrane, potentially enhancing permeability.

3. **Morpholine Substituent**: The morpholine ring is a six-membered heterocycle containing both oxygen and nitrogen. This group can increase the molecule's solubility and may also participate in hydrogen bonding or ionic interactions with the membrane, which can influence permeability.

4. **Ethyl Linkage**: The ethyl linkage connecting the morpholine to the quinazoline core provides flexibility and spatial separation, which can affect how the molecule interacts with the membrane. This flexibility might allow the molecule to adopt a conformation that optimizes its interaction with the membrane.

Overall, the combination of these structural features suggests that the given molecule is likely to exhibit high permeability in the PAMPA assay. The aromatic and heterocyclic components contribute to lipophilicity and potential interactions with the membrane, while the functional groups can facilitate hydrogen bonding and solubility, enhancing its ability to permeate the artificial membrane.

Final answer: High permeability

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# 37

**SMILES:** CC1=C(C(N=C(N1)NC2=NC3=CC=CC=C3O2)C4=NN(C=C4Cl)C)C(=O)NC5=NN=CS5

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound with several distinct structural features that influence its permeability in the PAMPA assay. Let's break down these features and their implications:

1. **Pyrazine Ring**: The presence of a pyrazine ring, which is a six-membered aromatic ring containing two nitrogen atoms, contributes to the molecule's polarity and potential hydrogen bonding capabilities. This can enhance the molecule's solubility in aqueous environments, which is beneficial for permeability through the PAMPA membrane, a model for biological membranes.

2. **Chloro Substituent**: The chloro group attached to the pyrazine ring introduces a degree of lipophilicity to the molecule. While this can enhance membrane permeability by increasing the molecule's ability to interact with lipid bilayers, it can also affect the overall polarity and solubility balance.

3. **Benzoxazole Moiety**: The benzoxazole group is a bicyclic structure that combines aromatic and heterocyclic characteristics. This moiety can contribute to the molecule's rigidity and planarity, potentially facilitating interactions with the membrane through π-π stacking or hydrophobic interactions.

4. **Thiadiazole Ring**: The thiadiazole ring is another heterocyclic component that can enhance the molecule's ability to form hydrogen bonds and coordinate with metal ions. This can influence the molecule's binding affinity to the membrane and its overall permeability.

5. **Carboxamide Group**: The carboxamide functional group is polar and can form hydrogen bonds, which may enhance the molecule's solubility and interaction with the PAMPA membrane. This group can also act as a site for hydrogen bonding with the membrane or other molecules, potentially affecting permeability.

6. **Imidazole Ring**: The imidazole ring is a five-membered aromatic ring containing nitrogen atoms, which can participate in hydrogen bonding and coordination with metal ions. This can enhance the molecule's interaction with the membrane and its overall permeability.

Overall, the given molecule exhibits a balance of polar and non-polar characteristics, with multiple functional groups capable of forming hydrogen bonds and hydrophobic interactions. These features suggest that the molecule would have moderate to high permeability in the PAMPA assay, as it can effectively interact with the artificial membrane while maintaining sufficient solubility in the assay environment.

Final answer: High permeability

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# 38

**SMILES:** CC1=C(C=CC(=C1)SCC2=C(N=C(S2)C3=CC=C(C=C3)C(F)(F)F)C)OCC(=O)O

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound with several functional groups and structural features that influence its permeability in the PAMPA assay. Let's break down these features and their impact on permeability:

1. **Thiazole Ring**: The presence of a thiazole ring, which is a five-membered heterocyclic compound containing both sulfur and nitrogen, can contribute to the molecule's stability and rigidity. This structural feature can enhance the molecule's ability to interact with the artificial membrane, potentially increasing its permeability.

2. **Trifluoromethylphenyl Group**: The trifluoromethyl group attached to the phenyl ring is highly electronegative due to the presence of fluorine atoms. This can increase the lipophilicity of the molecule, which often enhances membrane permeability by increasing the molecule's ability to dissolve in lipid bilayers.

3. **Sulfanyl (Thioether) Linkage**: The sulfanyl linkage (a sulfur atom connecting two carbon atoms) can influence the molecule's flexibility and polarity. Thioethers are generally non-polar, which can aid in membrane permeability by allowing the molecule to interact with the hydrophobic regions of the membrane.

4. **Phenoxy Group**: The phenoxy group, which is an ether linkage involving a phenyl ring, can contribute to the molecule's overall lipophilicity. This can enhance the molecule's ability to traverse lipid membranes, thus increasing permeability.

5. **Acetic Acid Moiety**: The presence of an acetic acid group introduces a polar, hydrophilic component to the molecule. This group can form hydrogen bonds with the artificial membrane, potentially increasing the molecule's interaction with the membrane and affecting its permeability. However, the acidic nature of this group can also lead to ionization, which might reduce permeability due to increased solubility in aqueous environments.

Overall, the given molecule exhibits a balance of hydrophobic and hydrophilic properties due to its diverse functional groups. The trifluoromethylphenyl group and thiazole ring likely contribute to high permeability by enhancing lipophilicity, while the acetic acid moiety may provide some degree of interaction with the membrane through hydrogen bonding. Therefore, the given molecule is likely to exhibit high permeability in the PAMPA assay.

Final answer: High permeability

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# 39

**SMILES:** CC1=CC(=NC(=C1)NC(=S)N2CCN(CC2)C3=CC=NC=C3)C

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a complex compound that includes several functional groups and structural features that influence its permeability in the PAMPA assay. Let's break down these features and their impact on permeability:

1. **Pyridine Rings**: The molecule contains two pyridine rings. Pyridine is a basic heterocyclic aromatic organic compound, and its presence can enhance the molecule's ability to interact with the artificial membrane through π-π stacking interactions and hydrogen bonding. The presence of methyl groups on one of the pyridine rings can increase the lipophilicity of the molecule, potentially enhancing its permeability by increasing its ability to dissolve in the lipid components of the membrane.

2. **Piperazine Ring**: The piperazine moiety is a six-membered ring containing two nitrogen atoms. This structure is known for its flexibility and ability to form hydrogen bonds, which can facilitate the molecule's interaction with the membrane. Piperazine rings are often found in pharmaceuticals due to their ability to enhance solubility and permeability.

3. **Carbothioamide Group**: The carbothioamide group is a functional group that contains both sulfur and nitrogen. This group can participate in hydrogen bonding and may also contribute to the molecule's overall polarity. The presence of sulfur can also influence the molecule's electronic properties, potentially affecting its interaction with the membrane.

Overall, the given molecule's structure suggests that it has a balance of hydrophilic and lipophilic properties, which is typical for molecules with moderate permeability in PAMPA assays. The combination of aromatic rings, flexible piperazine, and functional groups like carbothioamide can facilitate interactions with the artificial membrane, allowing the molecule to permeate to some extent. However, the exact permeability would depend on the specific conditions of the PAMPA assay, such as the type of artificial membrane used and the presence of other competing molecules.

Final answer: Low-to-moderate permeability.

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# 40

**SMILES:** CC1=CC(=NC(=C1)NC(=S)N2CCN(CC2)C3=C(C=C(C=C3)F)F)C

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a piperazine derivative with several functional groups that influence its permeability in the PAMPA assay. Let's analyze these features:

1. **Piperazine Ring**: The presence of a piperazine ring is a common feature in many pharmaceutical compounds. Piperazine rings are known for their ability to enhance the solubility and permeability of molecules. This is due to the basic nitrogen atoms, which can form hydrogen bonds and ionic interactions with the artificial membrane, facilitating passage through it.

2. **Difluorophenyl Group**: The difluorophenyl moiety contributes to the lipophilicity of the molecule. Fluorine atoms can enhance the membrane permeability by increasing the molecule's ability to interact with lipid bilayers. The presence of fluorine can also improve metabolic stability, which is beneficial for drug-like properties.

3. **Pyridinyl Group**: The pyridinyl group, particularly with a methyl substitution, adds to the molecule's overall hydrophobic character. Pyridine rings can participate in π-π interactions with the membrane, which may aid in permeability. The methyl group can further modulate the electronic properties of the pyridine, potentially enhancing its interaction with the membrane.

4. **Carbothioamide Group**: The carbothioamide functional group introduces a sulfur atom, which can form additional hydrogen bonds or dipole interactions with the membrane. This group can also contribute to the overall polarity of the molecule, which may affect its permeability.

Overall, the given molecule's combination of a piperazine ring, difluorophenyl group, pyridinyl group, and carbothioamide group suggests that it would exhibit high permeability in the PAMPA assay. These structural features collectively enhance the molecule's ability to interact with the artificial membrane, facilitating its passage through it.

Final answer: High permeability

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# 41

**SMILES:** CC1=CC(=NO1)NS(=O)(=O)C2=CC=C(C=C2)C(=O)NCC3=CC(=C(C=C3)Cl)Cl

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a sulfonamide, which is a class of compounds known for their antibacterial properties. The sulfonamide group is characterized by the presence of a sulfonyl functional group attached to an amine. This group is known to enhance the molecule's ability to interact with biological membranes, which can influence its permeability.

In the given molecule, the sulfonamide group is attached to a 3,4-dichlorophenyl moiety. The presence of chlorine atoms on the phenyl ring can increase the lipophilicity of the molecule, which may enhance its ability to permeate lipid membranes. This is because lipophilic compounds tend to dissolve more readily in lipid bilayers, facilitating their passage through cell membranes.

Additionally, the molecule contains a benzamide group, which can also contribute to its permeability. Benzamides are known to have good membrane permeability due to their planar structure, which allows them to interact favorably with lipid bilayers.

The presence of a 1,2,5-oxazole ring in the molecule can also play a role in its permeability. Heterocyclic rings like oxazoles can enhance the molecule's ability to interact with biological targets, potentially improving its permeability.

Overall, the combination of these functional groups suggests that the given molecule likely has high permeability to the artificial membrane, as it possesses both lipophilic and planar structural features that facilitate membrane interaction.

Final answer: High permeability.

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# 42

**SMILES:** CC1=CC(=NC=C1)NC(=S)N2CCN(CC2)C3=C(C=C(C=C3)Cl)Cl

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex compound that includes several functional groups and structural features that influence its permeability in the PAMPA assay. Let's break down these features and their impact on permeability:

1. **Piperazine Ring**: The presence of a piperazine ring is a key feature in the given molecule. Piperazine rings are known for their ability to enhance the solubility and permeability of compounds. This is due to the nitrogen atoms in the ring, which can participate in hydrogen bonding and improve the molecule's interaction with the artificial membrane.

2. **Dichlorophenyl Group**: The dichlorophenyl group contributes to the lipophilicity of the molecule. Chlorine atoms increase the hydrophobic character, which can enhance membrane permeability by allowing the molecule to interact more favorably with the lipid components of the artificial membrane.

3. **Pyridinyl Group**: The pyridinyl group, particularly with a methyl substitution, adds to the molecule's overall aromaticity and can influence its electronic properties. The nitrogen in the pyridine ring can also participate in hydrogen bonding, which may affect the molecule's interaction with the membrane.

4. **Carbothioamide Group**: The carbothioamide group introduces a sulfur atom, which can form additional hydrogen bonds and influence the molecule's polarity. This group can also affect the overall stability and solubility of the molecule in the PAMPA assay.

Considering these structural features, the given molecule is likely to exhibit high permeability in the PAMPA assay. The combination of the piperazine ring, dichlorophenyl group, pyridinyl group, and carbothioamide group suggests a balance of hydrophilic and hydrophobic properties, which is conducive to permeability through the artificial membrane. The molecule's ability to form hydrogen bonds and its moderate lipophilicity likely facilitate its passage through the membrane, making it a candidate for high permeability.

Final answer: High permeability.

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# 43

**SMILES:** CC1=CC(=NO1)NS(=O)(=O)C2=CC=C(C=C2)NC(=O)CC3=CC(=C(C=C3)F)Cl

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a sulfonamide, which is a class of compounds known for their antibacterial properties. The sulfonamide group is characterized by the presence of a sulfonyl functional group attached to an amine. This group is known to enhance the molecule's ability to interact with biological targets, such as enzymes or receptors, due to its ability to form hydrogen bonds and other interactions.

In the given molecule, the sulfonamide group is attached to a phenyl ring, which is further substituted with a chloro and a fluoro group. These halogen substituents can influence the molecule's lipophilicity and electronic properties, potentially affecting its permeability. The presence of the chloro and fluoro groups can increase the molecule's lipophilicity, which may enhance its ability to permeate lipid membranes.

The molecule also contains an acetamide group, which can contribute to its solubility and ability to form hydrogen bonds. This group is linked to a phenyl ring, which is further substituted with a 1,2,5-oxazole ring. The oxazole ring is a heterocyclic compound that can contribute to the molecule's overall stability and ability to interact with biological targets.

Overall, the combination of these functional groups suggests that the given molecule may have moderate permeability due to the balance between its hydrophilic and lipophilic properties. The sulfonamide group, along with the chloro and fluoro substituents, likely enhances its ability to permeate lipid membranes, while the oxazole and acetamide groups may contribute to its solubility and interaction with biological targets.

Final answer: Low-to-moderate permeability.

------
# 44

**SMILES:** C1CCC2=C(C1)N=C3CCCCC3=N2

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a derivative of the quinoline structure, specifically a hexahydroquinoline. This means that the quinoline core, which typically consists of a fused aromatic benzene and pyridine ring, has been partially hydrogenated. In this case, the hydrogenation has occurred on the pyridine ring, resulting in a saturated or partially saturated six-membered ring.

The presence of the hexahydro component indicates that the molecule has additional hydrogen atoms, which reduces the aromaticity of the pyridine ring. This reduction in aromaticity can affect the molecule's electronic properties, such as its ability to participate in π-π interactions or hydrogen bonding, which are important for permeability.

In the context of the Parallel Artificial Membrane Permeability Assay (PAMPA), the artificial membrane mimics biological membranes, which are typically composed of lipid bilayers. The permeability of a molecule through such a membrane is influenced by its lipophilicity, size, and ability to form hydrogen bonds.

For the given molecule, the partially saturated pyridine ring may enhance its lipophilicity compared to a fully aromatic quinoline. This increased lipophilicity can facilitate the molecule's passage through the lipid-like membrane, suggesting that it may have high permeability. However, the exact permeability would also depend on other factors such as the molecule's size and the presence of any polar functional groups that could interact with the membrane.

Overall, the structural features of the given molecule, particularly the hexahydro component, suggest that it may exhibit high permeability in the PAMPA assay.

Final answer: High permeability

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# 45

**SMILES:** COC1C(CC2CN3CCC4=C(C3CC2C1CO)NC5=C4C=CC(=C5)OC)O

**Label:** 0

**Predi:** 0

**Correct:** 1

# Response:
The given molecule is a yohimban alkaloid, which is a class of compounds known for their complex polycyclic structures. The yohimban framework is a type of indole alkaloid, characterized by a multi-ring system that includes an indole moiety. This structural complexity often contributes to the molecule's ability to interact with biological targets, such as receptors in the nervous system.

In the context of the Parallel Artificial Membrane Permeability Assay (PAMPA), the permeability of the given molecule is influenced by its structural features. The presence of multiple rings and heteroatoms, such as nitrogen and oxygen, can affect the molecule's lipophilicity and ability to traverse lipid membranes. The methoxy groups in the structure can increase lipophilicity, potentially enhancing membrane permeability by increasing the molecule's ability to dissolve in lipid environments.

Additionally, the hydroxyl groups present in the structure can form hydrogen bonds, which may facilitate interactions with the artificial membrane, potentially improving permeability. However, these polar groups can also introduce steric hindrance and reduce permeability by limiting the molecule's ability to fit through the membrane pores.

Overall, the balance between the lipophilic and hydrophilic characteristics of the given molecule, along with its complex ring system, will determine its permeability in the PAMPA assay. The specific arrangement of functional groups and the overall molecular geometry will dictate how the molecule interacts with the artificial membrane, influencing its classification as having high permeability or low-to-moderate permeability.

Final answer: Low-to-moderate permeability.

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# 46

**SMILES:** CN1C2=C(C(=O)N(C1=O)C)NC(=O)N2

**Label:** 0

**Predi:** 0

**Correct:** 1

# Response:
The given molecule is a derivative of xanthine, which is a purine compound. The structure of the molecule includes a purine ring system, which is a bicyclic structure consisting of a pyrimidine ring fused to an imidazole ring. This core structure is common in many biologically active compounds, including caffeine and theobromine.

The presence of three carbonyl groups (trione) in the molecule indicates that it has multiple ketone functionalities. These carbonyl groups are likely to increase the molecule's polarity, which can influence its permeability. The carbonyl groups can form hydrogen bonds with the artificial membrane, potentially enhancing the molecule's interaction with the membrane.

Additionally, the presence of two methyl groups on the purine ring increases the hydrophobic character of the molecule. These methyl groups can enhance the molecule's ability to interact with the lipid components of the artificial membrane, potentially increasing its permeability.

Overall, the balance of polar and non-polar characteristics in the given molecule suggests that it may have moderate permeability to the artificial membrane. The polar carbonyl groups can facilitate interaction with the membrane, while the hydrophobic methyl groups can enhance lipid solubility, allowing the molecule to traverse the membrane.

Final answer: Low-to-moderate permeability.

------
# 47

**SMILES:** C1CNCCC1NC2=CC=CC(=N2)C3=CN=C4N3C=C(C=C4)Cl

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex structure that includes several key features influencing its permeability in the PAMPA assay. Let's break down these features and their implications:

1. **Imidazo[1,2-a]pyridine Core**: This bicyclic structure is known for its planar and aromatic characteristics, which can enhance the molecule's ability to interact with lipid membranes. The presence of this core suggests that the molecule may have a degree of lipophilicity, which can facilitate its passage through the artificial membrane.

2. **Chloro Substituent**: The chloro group on the imidazo[1,2-a]pyridine ring can influence the molecule's electronic properties and lipophilicity. Chlorine is an electronegative atom, which can increase the molecule's overall lipophilicity and potentially enhance its ability to permeate the membrane.

3. **Piperidin-1-ylpyridine Moiety**: The piperidine ring is a saturated, nitrogen-containing heterocycle that can contribute to the molecule's basicity and solubility. The presence of this moiety may enhance the molecule's ability to interact with the membrane through hydrogen bonding or ionic interactions, depending on the pH of the environment.

4. **Overall Structure**: The combination of aromatic and heterocyclic components in the given molecule suggests a balance between hydrophilic and lipophilic properties. This balance is crucial for permeability, as it allows the molecule to interact with both the aqueous environment and the lipid components of the membrane.

Considering these structural features, the given molecule is likely to exhibit high permeability in the PAMPA assay. The aromatic and heterocyclic components contribute to its ability to traverse the artificial membrane, while the chloro substituent and piperidinyl group may enhance its interaction with the membrane.

Final answer: High permeability

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# 48

**SMILES:** CCOC1=CC=CC=C1C(=O)NC2=C(C=NC=C2)C(=O)NC3=CC(=CC=C3)S(=O)(=O)C(F)(F)F

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a benzamide derivative, which is a class of compounds known for their potential biological activity, often used in pharmaceuticals. The structure of the given molecule includes several key features that influence its permeability:

1. **Benzamide Core**: The presence of the benzamide moiety suggests that the molecule has a planar structure, which can facilitate interactions with biological membranes. Benzamides are known for their ability to permeate lipid bilayers due to their aromatic nature, which allows for van der Waals interactions with the lipid components of the membrane.

2. **Aromatic Rings**: The molecule contains multiple aromatic rings, including a phenyl group and a pyridine ring. These rings contribute to the molecule's hydrophobic character, enhancing its ability to interact with the hydrophobic regions of the artificial membrane. Aromatic rings can also participate in π-π stacking interactions, which can further stabilize the molecule's interaction with the membrane.

3. **Ethoxy Group**: The ethoxy group attached to the phenyl ring introduces a slight increase in hydrophilicity, which can affect the molecule's overall solubility and permeability. This group may enhance the molecule's ability to interact with the polar head groups of the artificial membrane.

4. **Sulfamoyl Group**: The presence of the sulfamoyl group, which is a sulfonamide derivative, adds to the molecule's hydrophilicity. Sulfonamides are known for their ability to form hydrogen bonds, which can increase the molecule's interaction with the polar regions of the membrane. This group may also contribute to the molecule's solubility in aqueous environments, potentially affecting its permeability.

5. **Trifluoromethyl Group**: The trifluoromethyl group is highly electronegative and can influence the molecule's electronic properties. This group can enhance the molecule's lipophilicity, which may improve its ability to permeate the lipid-rich regions of the artificial membrane. Additionally, the trifluoromethyl group can affect the molecule's metabolic stability, which is an important factor in drug design.

Overall, the combination of aromatic rings, the ethoxy group, the sulfamoyl group, and the trifluoromethyl group suggests that the given molecule has a balance of hydrophobic and hydrophilic properties, which can facilitate its permeability through the artificial membrane. The molecule's structure indicates that it may have moderate to high permeability, depending on the specific conditions of the PAMPA assay.

Final answer: Low-to-moderate permeability.

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# 49

**SMILES:** C1=CC=C(C=C1)COC2=CC(=CC=C2)SC3=CC(=C(C=C3)CCC(CO)(CO)N)Cl

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a complex organic compound with several functional groups that influence its permeability in the PAMPA assay. Let's break down the structural features and their impact on permeability:

1. **Amino and Hydroxyl Groups**: The presence of amino and hydroxyl groups in the given molecule suggests that it is polar. These groups can form hydrogen bonds with the artificial membrane, potentially increasing its interaction with the membrane and enhancing permeability. However, the balance between hydrophilic and lipophilic properties will be crucial in determining overall permeability.

2. **Sulfanyl Group**: The sulfanyl group (a sulfur atom bonded to a phenyl ring) introduces a degree of lipophilicity to the molecule. This group can interact with the hydrophobic regions of the artificial membrane, which may facilitate permeation. However, the presence of the sulfur atom can also introduce steric hindrance, affecting the molecule's ability to pass through the membrane.

3. **Phenyl Rings**: The phenyl rings in the structure contribute to the lipophilic character of the molecule. These aromatic rings can engage in π-π interactions with the membrane, which may enhance permeability. However, the size and rigidity of the phenyl rings can also limit the molecule's ability to fit through the membrane pores.

4. **Methoxy Group**: The methoxy group attached to a phenyl ring adds to the lipophilicity of the molecule. This group can enhance membrane permeability by increasing the molecule's ability to dissolve in the lipid bilayer of the membrane.

5. **Overall Structure**: The combination of polar and non-polar groups suggests that the given molecule has a balanced amphiphilic nature. This balance is often associated with moderate permeability in PAMPA assays, as the molecule can interact with both hydrophilic and hydrophobic components of the membrane.

In summary, the given molecule's permeability in the PAMPA assay is likely moderate due to its balanced amphiphilic nature, with polar groups enhancing solubility and non-polar groups facilitating membrane interaction.

Final answer: Low-to-moderate permeability.

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# 50

**SMILES:** C1CCC(C1)C2=C(C=CC(=C2)C3=CNC4=C3C=C(C=N4)C5=CC=CC=C5)C(=O)O

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that includes several distinct structural features, each contributing to its permeability characteristics in the PAMPA assay.

1. **Pyrrolo[2,3-b]pyridine Moiety**: This bicyclic structure is a fused ring system combining pyrrole and pyridine. The presence of nitrogen in the pyridine ring can enhance the molecule's ability to form hydrogen bonds and engage in polar interactions with the artificial membrane. This can increase the molecule's permeability by facilitating its passage through the membrane.

2. **Phenyl Group**: The phenyl group attached to the pyrrolo[2,3-b]pyridine moiety is a hydrophobic aromatic ring. Aromatic rings can participate in π-π interactions with the membrane, which may enhance the molecule's permeability by stabilizing its interaction with the membrane surface.

3. **Cyclopentyl Ring**: The cyclopentyl group is a non-aromatic, hydrophobic ring that can increase the lipophilicity of the molecule. This can enhance the molecule's ability to traverse lipid membranes, contributing to its permeability.

4. **Carboxylic Acid Group**: The carboxylic acid group is a polar functional group capable of forming hydrogen bonds and ionic interactions. This group can increase the molecule's solubility in aqueous environments, which is important for its interaction with the PAMPA membrane. However, the presence of this group can also introduce some degree of polarity, which may limit the molecule's permeability by hindering its passage through the hydrophobic regions of the membrane.

Overall, the given molecule's structure suggests a balance between hydrophobic and hydrophilic properties. The aromatic and cyclopentyl groups contribute to hydrophobic interactions, while the pyrrolo[2,3-b]pyridine and carboxylic acid groups provide polar interactions. These features collectively suggest that the given molecule would exhibit high permeability in the PAMPA assay, as it can effectively interact with both hydrophobic and hydrophilic components of the artificial membrane.

Final answer: High permeability

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# 51

**SMILES:** CC[C@@H](C1=NC2=C(C(=CC=C2)F)C(=O)N1C3=CC=CC=C3)NC4=NC=NC5=C4NC=N5

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a fluorinated quinazoline derivative with a specific stereochemistry, as indicated by the (1R)-configuration. This stereochemistry is crucial for its biological activity, particularly in its role as an inhibitor of the epidermal growth factor receptor (EGFR) tyrosine kinase.

The molecule's structure includes a quinazoline core, which is a bicyclic compound consisting of a benzene ring fused to a pyrimidine ring. This core is known for its planar structure, which can facilitate interactions with biological targets such as enzymes and receptors. The presence of a fluorine atom on the quinazoline ring can enhance the molecule's lipophilicity and metabolic stability, potentially improving its ability to permeate cell membranes.

The molecule also contains a triazinyl group, which is a heterocyclic ring containing three nitrogen atoms. This group is linked to an anilino group, which is an aromatic amine. The anilino group can participate in hydrogen bonding and π-π interactions, which are important for binding to the EGFR active site.

The stereochemistry of the molecule, specifically the (1R)-configuration, suggests that the molecule is chiral and that the spatial arrangement of its atoms is critical for its biological activity. This configuration can influence how the molecule fits into the binding site of the EGFR, affecting its inhibitory potency.

In terms of permeability, the given molecule's planar aromatic rings and heterocyclic components suggest that it may have moderate to high permeability through the artificial membrane, as these features can facilitate passage through lipid bilayers. However, the exact permeability would depend on additional factors such as the molecule's overall size, solubility, and the specific properties of the artificial membrane used in the PAMPA assay.

Overall, the structural features of the given molecule, including its quinazoline core, fluorine substitution, and chiral center, suggest that it may have high permeability in the PAMPA assay, but this would need to be confirmed through experimental data.

Final answer: High permeability

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# 52

**SMILES:** CC1=C(C=C(C=C1)C(=O)N)NC2=NC=CC(=N2)C3=CN(C4=C3C=CN=C4)C(C)C

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound with several functional groups and aromatic rings, which contribute to its permeability characteristics in the PAMPA assay.

1. **Aromatic Rings**: The molecule contains multiple aromatic rings, including a pyrrolopyridine and a pyrimidine ring. Aromatic rings generally enhance lipophilicity, which can increase the molecule's ability to permeate lipid membranes. This is because aromatic rings can interact with the hydrophobic regions of the artificial membrane, facilitating passage through the membrane.

2. **Amino Group**: The presence of an amino group attached to the pyrrolopyridine ring introduces a site for hydrogen bonding. This can enhance the molecule's solubility in aqueous environments, which is important for its interaction with the artificial membrane. The amino group can also participate in ionic interactions with the membrane, potentially aiding in permeation.

3. **Methyl and Isopropyl Groups**: The methyl group on the pyrrolopyridine and the isopropyl group on the pyrimidine contribute to the molecule's hydrophobic character. These groups can further enhance lipophilicity, promoting membrane permeability by increasing the molecule's affinity for the lipid bilayer.

4. **Benzamide Moiety**: The benzamide portion of the molecule provides additional sites for hydrogen bonding and can interact with the polar regions of the artificial membrane. The presence of the amide group can also influence the molecule's overall conformation, potentially affecting its ability to permeate the membrane.

Overall, the combination of aromatic rings, functional groups capable of hydrogen bonding, and hydrophobic substituents suggests that the given molecule likely exhibits high permeability in the PAMPA assay. These structural features enable the molecule to effectively interact with the artificial membrane, facilitating its passage through the lipid layer.

Final answer: High permeability

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# 53

**SMILES:** CN1CCN(CC1)CC(=O)N(C)C2=CC=C(C=C2)N=C(C3=CC=CC=C3)C4=C(NC5=C4C=CC(=C5)C(=O)OC)O

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that includes several functional groups and structural features that influence its permeability in the PAMPA assay. Let's break down these features and their impact on permeability:

1. **Indole Core**: The presence of an indole moiety in the given molecule suggests a relatively planar and aromatic structure. Indole rings are known for their ability to participate in π-π stacking interactions, which can enhance the molecule's ability to interact with the artificial membrane. This aromaticity can contribute to the molecule's overall stability and permeability.

2. **Hydroxy Group**: The hydroxy group attached to the indole ring can form hydrogen bonds with the artificial membrane, potentially increasing the molecule's solubility and permeability. Hydrogen bonding is a key interaction that can facilitate the passage of the molecule through the membrane.

3. **Piperazine Ring**: The inclusion of a piperazine ring, which is a six-membered heterocyclic amine, can enhance the molecule's solubility and permeability due to its basic nature. The piperazine ring can also participate in ionic interactions with the membrane, which may aid in permeation.

4. **Phenyl and Carbamoyl Linkages**: The phenyl group linked to the carbamoyl moiety provides additional aromatic character, which can further enhance membrane interaction through π-π stacking. The carbamoyl linkage introduces a polar amide group, which can form hydrogen bonds, contributing to the molecule's solubility and permeability.

5. **Ester Group**: The ester group in the molecule, specifically the methyl ester, can influence the molecule's lipophilicity. Esters are generally more lipophilic than their corresponding acids, which can enhance the molecule's ability to permeate lipid membranes. However, esters can also be susceptible to hydrolysis, which might affect the molecule's stability in the PAMPA assay.

Overall, the given molecule's combination of aromaticity, hydrogen bonding potential, and lipophilic ester group suggests that it would exhibit high permeability in the PAMPA assay. The balance of hydrophilic and lipophilic properties, along with the ability to form various non-covalent interactions, supports its passage through the artificial membrane.

Final answer: High permeability

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# 54

**SMILES:** COC1=C(N=C(O1)C2=CC=CC3=CC=CC=C32)C(=O)O

**Label:** 0

**Predi:** 1

**Correct:** 0

# Response:
The given molecule is a complex organic compound that features several functional groups and aromatic systems, which influence its permeability in the PAMPA assay.

Firstly, the presence of the methoxy group attached to the oxazole ring introduces a degree of polarity to the molecule. Methoxy groups can enhance solubility in polar solvents, which may facilitate the molecule's interaction with the polar components of the artificial membrane. However, the overall effect on permeability will depend on the balance between the polar and non-polar regions of the molecule.

The oxazole ring itself is a heterocyclic aromatic compound, which contributes to the molecule's rigidity and planarity. Aromatic rings, such as the naphthalene moiety in the given molecule, are known for their ability to engage in π-π interactions with other aromatic systems. This can enhance the molecule's ability to interact with the membrane, potentially increasing permeability.

The naphthalene moiety is a large, planar aromatic system that can increase the lipophilicity of the molecule. This lipophilic character can facilitate the passage of the molecule through the lipid-like components of the artificial membrane, suggesting a potential for high permeability.

The carboxylic acid group is a highly polar functional group that can form hydrogen bonds and ionic interactions. This group can enhance the molecule's solubility in aqueous environments and may also interact with the polar head groups of the artificial membrane, potentially increasing permeability.

Overall, the given molecule's combination of aromatic systems, polar functional groups, and lipophilic characteristics suggests that it may exhibit high permeability in the PAMPA assay. The balance between these features will determine the extent to which the molecule can traverse the artificial membrane.

Final answer: High permeability.

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# 55

**SMILES:** CCNC(=O)C[C@H]1C2=NN=C(N2C3=C(C=C(C=C3)OC)C(=N1)C4=CC=C(C=C4)Cl)C

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a member of the triazolobenzodiazepine class, which is known for its central nervous system activity. The structure of the given molecule includes several key features that influence its permeability:

1. **Triazolobenzodiazepine Core**: This core structure is a fused ring system that includes a triazole ring and a benzodiazepine ring. Such fused ring systems often enhance the molecule's ability to interact with biological membranes due to their planar and rigid nature, which can facilitate passage through lipid bilayers.

2. **Chlorophenyl Group**: The presence of a chlorophenyl group contributes to the molecule's lipophilicity. The chlorine atom increases the electron density of the phenyl ring, which can enhance the molecule's ability to penetrate lipid membranes by increasing its hydrophobic interactions.

3. **Methoxy and Methyl Substituents**: The methoxy and methyl groups on the benzodiazepine ring increase the molecule's lipophilicity, which is a key factor in membrane permeability. These groups can also influence the molecule's binding affinity to target receptors by affecting its overall shape and electronic distribution.

4. **Acetamide Moiety**: The acetamide group introduces a polar element to the molecule, which can form hydrogen bonds with the artificial membrane. This can affect the molecule's solubility and permeability, potentially enhancing its ability to interact with the membrane.

Overall, the combination of these structural features suggests that the given molecule has a high degree of lipophilicity, which is likely to enhance its permeability through the artificial membrane. The balance of hydrophobic and hydrophilic elements in the molecule allows it to interact effectively with the membrane, facilitating its passage.

Final answer: High permeability

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# 56

**SMILES:** C1=CC=C2C(=C1)C(=NC(=N2)N3C=CN=C3)NC4=CC(=C(C=C4)F)F

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a quinazoline derivative, which is a class of compounds known for their biological activity, particularly in the realm of pharmaceuticals. The quinazoline core is a bicyclic structure consisting of a benzene ring fused to a pyrimidine ring. This core is known for its planar structure, which can facilitate interactions with biological targets, such as enzymes or receptors.

The presence of the pyridine ring attached to the quinazoline core can enhance the molecule's ability to participate in hydrogen bonding and π-π stacking interactions, which are important for binding to biological targets. The nitrogen atom in the pyridine ring can act as a hydrogen bond acceptor, potentially increasing the molecule's affinity for certain biological sites.

The difluorophenyl group attached to the nitrogen atom of the quinazoline core introduces fluorine atoms into the structure. Fluorine atoms are highly electronegative and can influence the electronic properties of the molecule. They can increase the lipophilicity of the molecule, which may enhance its ability to permeate lipid membranes. Additionally, the presence of fluorine atoms can affect the metabolic stability of the molecule, potentially prolonging its activity in biological systems.

Overall, the combination of the quinazoline core, pyridine ring, and difluorophenyl group suggests that the given molecule may have high permeability to the artificial membrane due to its planar structure, potential for hydrogen bonding, and increased lipophilicity from the fluorine atoms. These features can facilitate the molecule's passage through lipid membranes, making it a candidate for further investigation in drug discovery.

Final answer: High permeability

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# 57

**SMILES:** C1=CC=C2C(=C1)C(=NC(=N2)NC3=CC=NC=C3)NC4=CC(=C(C=C4)F)F

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a quinazoline derivative, which is a class of compounds known for their biological activity, often used in pharmaceuticals. The quinazoline core is a bicyclic structure consisting of a benzene ring fused to a pyrimidine ring. This core is known for its planar structure, which can facilitate interactions with biological targets, such as enzymes or receptors.

The molecule has two amine groups attached to the quinazoline core, which are likely to enhance its ability to form hydrogen bonds with biological targets. These amine groups can also increase the molecule's solubility in water, which is beneficial for its absorption and distribution in biological systems.

The presence of the pyridinyl groups attached to the nitrogen atoms in the quinazoline structure adds to the molecule's complexity. Pyridine rings are aromatic and can participate in π-π stacking interactions, which can be important for binding to aromatic amino acids in proteins. Additionally, the fluorine atoms on the phenyl ring can influence the molecule's electronic properties, potentially affecting its binding affinity and selectivity.

The PAMPA assay is designed to mimic the permeability of a molecule through biological membranes. The artificial membrane used in this assay is typically composed of lipophilic and hydrophilic components, which can interact with the molecule in a way similar to a biological membrane. The given molecule's quinazoline core, along with its functional groups, suggests that it may have moderate lipophilicity, allowing it to interact with both the hydrophilic and lipophilic components of the membrane.

Overall, the combination of the quinazoline core, amine groups, pyridinyl substituents, and fluorine atoms suggests that the given molecule would exhibit moderate permeability in the PAMPA assay, balancing between hydrophilic and lipophilic interactions with the artificial membrane.

Final answer: Low-to-moderate permeability.

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# 58

**SMILES:** C1=CC(=C(C(=C1)[N+](=O)[O-])O)CNC2=CC=C(C=C2)S(=O)(=O)NC3=NC=CS3

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a sulfonamide, which is a class of compounds known for their antibacterial properties. The sulfonamide group is characterized by the presence of a sulfonyl functional group attached to an amine. This group is known to enhance the molecule's ability to interact with biological targets, such as enzymes or receptors, due to its polar nature and ability to form hydrogen bonds.

The structure of the given molecule includes a sulfonamide group attached to a benzene ring, which is further substituted with a hydroxy group and a nitrophenyl group. The presence of the hydroxy group can increase the molecule's polarity and solubility in water, which may enhance its permeability through the artificial membrane.

Additionally, the molecule contains a thiazole ring, which is a five-membered heterocyclic compound containing both sulfur and nitrogen. This ring can contribute to the molecule's overall stability and ability to interact with biological membranes due to its aromatic nature and potential for hydrogen bonding.

The phenyl group linked to the thiazole ring is connected to the sulfonamide group through a methylene bridge. This linkage provides flexibility to the molecule, allowing it to adopt conformations that may facilitate its passage through the membrane.

Overall, the combination of these functional groups suggests that the given molecule may have moderate permeability through the artificial membrane. The polar sulfonamide and hydroxy groups can enhance solubility and interaction with the membrane, while the aromatic rings provide structural stability and potential for membrane interaction.

Final answer: Low-to-moderate permeability.

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# 59

**SMILES:** C1=CC(=CC=C1NCC2=C(C=C(C=C2)N)O)[S+](=O)(NC3=NC=CS3)[O-]

**Label:** 0

**Predi:** 1

**Correct:** 0

# Response:
The given molecule is a sulfonamide, which is a class of compounds known for their antimicrobial properties. The sulfonamide group is characterized by the presence of a sulfonyl functional group attached to an amine. This group is known to enhance the molecule's ability to interact with biological membranes due to its polar nature, which can facilitate passage through lipid bilayers.

The structure of the given molecule includes an aromatic phenyl ring substituted with an amino group and a hydroxy group. The presence of these groups can increase the molecule's hydrophilicity, which may enhance its permeability through the artificial membrane by increasing its solubility in aqueous environments.

Additionally, the molecule contains a thiazole ring, which is a five-membered heterocyclic compound containing both sulfur and nitrogen. This ring can contribute to the molecule's overall stability and may also play a role in its ability to interact with biological targets, potentially affecting its permeability.

The sulfonamide group, along with the hydrophilic substituents on the phenyl ring, suggests that the given molecule would have moderate to high permeability in the PAMPA assay. This is because the molecule's polar and potentially ionizable groups can facilitate its passage through the artificial membrane, while the aromatic and heterocyclic components may provide structural stability and specificity in its interactions with the membrane.

Final answer: High permeability.

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# 60

**SMILES:** COC1=CC=CC(=C1N)CNC2=CC=C(C=C2)S(=O)(=O)NC3=NC=CS3

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a sulfonamide, which is a class of compounds known for their antibacterial properties. The sulfonamide group is characterized by the presence of a sulfonyl functional group attached to an amine. This group is known to enhance the molecule's ability to interact with biological membranes due to its polar nature, which can facilitate passage through lipid bilayers.

The structure of the given molecule includes several key features that influence its permeability:

1. **Amino Groups**: The presence of amino groups in the structure increases the molecule's hydrophilicity, which can enhance its solubility in aqueous environments. This can improve the molecule's ability to permeate through the artificial membrane, as it can interact favorably with the polar head groups of the membrane.

2. **Methoxy Group**: The methoxy group contributes to the molecule's overall polarity and can also influence its electronic properties. This can affect how the molecule interacts with the artificial membrane, potentially enhancing its permeability by increasing its solubility in the membrane's environment.

3. **Thiazole Ring**: The thiazole ring is a heterocyclic aromatic compound that can contribute to the molecule's overall stability and rigidity. This can affect the molecule's ability to fit into the membrane's structure, potentially facilitating its passage through the membrane.

4. **Phenyl Ring**: The phenyl ring provides a hydrophobic character to the molecule, which can aid in its interaction with the lipid components of the artificial membrane. This can enhance the molecule's permeability by allowing it to embed within the lipid bilayer.

Overall, the combination of these functional groups and structural features suggests that the given molecule would exhibit high permeability in the artificial membrane, as it possesses a balance of hydrophilic and hydrophobic properties that facilitate interaction with the membrane.

Final answer: High permeability

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# 61

**SMILES:** CC1=C(NC(=C1C(=O)C)C)C(=O)NC2=CC=C(C=C2)OC

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several functional groups and structural elements that influence its permeability in the PAMPA assay. Let's break down the key components and their impact on permeability:

1. **Pyrrole Ring**: The core structure of the given molecule includes a pyrrole ring, which is a five-membered heterocyclic aromatic ring containing nitrogen. Pyrrole rings are relatively planar and aromatic, which can enhance the molecule's ability to interact with the artificial membrane through π-π stacking interactions. This can contribute to moderate to high permeability, depending on the overall size and lipophilicity of the molecule.

2. **Acetyl Group**: The presence of an acetyl group attached to the pyrrole ring introduces a polar carbonyl group. This can increase the molecule's overall polarity, potentially enhancing its solubility in aqueous environments and facilitating interactions with the polar head groups of the artificial membrane. However, the acetyl group's size and position may also create steric hindrance, which could limit permeability.

3. **Methoxyphenyl Group**: The methoxyphenyl group is an aromatic ring with a methoxy substituent, which is an electron-donating group. This can increase the lipophilicity of the molecule, enhancing its ability to traverse lipid membranes. The aromatic nature of the phenyl group can also contribute to π-π interactions with the membrane, potentially increasing permeability.

4. **Carboxamide Group**: The carboxamide group is a polar functional group that can form hydrogen bonds with the artificial membrane. This can enhance the molecule's solubility and interaction with the membrane, potentially increasing permeability. However, the presence of this group also adds to the overall polarity of the molecule, which may counteract the effects of the lipophilic groups.

5. **Methyl Groups**: The dimethyl substitution on the pyrrole ring increases the hydrophobic character of the molecule. These groups can enhance lipophilicity, which is generally favorable for membrane permeability. However, their small size and position may not significantly hinder or enhance permeability.

Overall, the given molecule has a balance of hydrophobic and hydrophilic characteristics, with aromatic and polar functional groups that can interact with the artificial membrane. The presence of the pyrrole ring, methoxyphenyl group, and carboxamide group suggests that the molecule may exhibit moderate to high permeability in the PAMPA assay, as these features can facilitate interactions with the membrane while maintaining sufficient solubility.

Final answer: High permeability.

------
# 62

**SMILES:** CC1=C(NC(=C1C(=O)C)C)C(=O)NC2=CC=C(C=C2)Cl

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is an aromatic amide, which is characterized by the presence of an amide group attached to an aromatic ring. In this case, the amide group is connected to a pyrrole ring, which is a five-membered heterocyclic aromatic ring containing nitrogen. The pyrrole ring is further substituted with methyl groups, which can influence the molecule's electronic properties and steric profile.

The presence of the 4-chlorophenyl group attached to the nitrogen of the amide group introduces an aromatic ring with a chlorine substituent. This chlorinated aromatic ring can enhance the molecule's lipophilicity, potentially increasing its ability to interact with lipid membranes.

The artificial membrane used in the PAMPA assay is designed to mimic biological membranes, so the permeability of the given molecule is influenced by its ability to traverse this model membrane. The aromatic nature of the molecule, combined with the lipophilic chlorophenyl group, suggests that the molecule may have a favorable interaction with the lipid components of the membrane, potentially leading to high permeability.

Additionally, the methyl groups on the pyrrole ring can further enhance the molecule's lipophilicity, which may also contribute to its permeability. However, the overall permeability will depend on the balance between the molecule's lipophilicity and its ability to form hydrogen bonds or other interactions with the membrane.

In summary, the given molecule's structural features, such as the aromatic amide linkage, chlorophenyl group, and methyl substitutions, suggest that it may exhibit high permeability in the PAMPA assay due to its potential for favorable interactions with the artificial membrane.

Final answer: High permeability.

------
# 63

**SMILES:** COC1=C(C=C(C=C1)C2CC(=O)NC3=C2SC(=N3)N)OC

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a thienopyrimidine derivative, which is characterized by a fused ring system consisting of a thiophene and a pyrimidine ring. This structure is known for its potential biological activity and is often used in pharmaceuticals.

The permeability of the given molecule in the PAMPA assay can be influenced by several structural features:

1. **Aromaticity and Planarity**: The presence of a dimethoxyphenyl group contributes to the molecule's aromaticity and planarity. Aromatic and planar structures generally enhance lipophilicity, which can increase membrane permeability. The dimethoxy groups, being electron-donating, may further enhance the lipophilic character of the phenyl ring, potentially increasing permeability.

2. **Functional Groups**: The amino group in the molecule can form hydrogen bonds, which may affect its interaction with the artificial membrane. While hydrogen bonding can influence solubility and permeability, the presence of an amino group can also introduce some degree of polarity, which might reduce permeability compared to non-polar molecules.

3. **Fused Ring System**: The thienopyrimidine core is a rigid, planar structure that can facilitate passage through lipid membranes due to its ability to stack with other aromatic systems in the membrane. The rigidity and planarity of the fused ring system can enhance the molecule's ability to traverse the membrane.

4. **Overall Lipophilicity**: The combination of aromatic rings and functional groups suggests that the given molecule has a balance of hydrophilic and lipophilic properties. The dimethoxyphenyl group and the thienopyrimidine core contribute to the lipophilic nature, while the amino group introduces some hydrophilicity.

Considering these structural features, the given molecule is likely to exhibit high permeability in the PAMPA assay due to its aromatic and planar nature, which enhances lipophilicity, and the presence of functional groups that can interact with the membrane.

Final answer: High permeability

------
# 64

**SMILES:** CCN1CCC2=C(C1)SC(=C2C(=O)N)NC(=O)NC3=CC(=C(C=C3)Cl)Cl

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several functional groups and structural elements that influence its permeability in the PAMPA assay. Let's break down the key components and their impact on permeability:

1. **Thieno[2,3-c]pyridine Core**: This bicyclic structure is a fusion of a thiophene ring and a pyridine ring. The presence of sulfur in the thiophene ring can enhance lipophilicity, which generally increases membrane permeability. However, the pyridine ring can introduce some degree of polarity, which may balance this effect.

2. **Carboxamide Group**: The carboxamide group is a polar functional group that can form hydrogen bonds with the artificial membrane. This can enhance the molecule's interaction with the membrane, potentially increasing permeability. However, it also introduces some polarity, which might reduce permeability compared to non-polar molecules.

3. **3,4-Dichlorophenyl Carbamoyl Moiety**: The dichlorophenyl group is a hydrophobic aromatic ring with two chlorine atoms, which can increase lipophilicity. The presence of chlorine atoms can also enhance the molecule's ability to interact with lipid membranes due to increased van der Waals interactions. This moiety is likely to contribute to high permeability due to its hydrophobic character.

4. **Ethyl Group**: The ethyl group is a small, non-polar alkyl chain that can increase the lipophilicity of the molecule. This can enhance membrane permeability by allowing the molecule to better interact with the lipid bilayer of the artificial membrane.

Overall, the given molecule contains a balance of hydrophobic and polar elements. The hydrophobic dichlorophenyl and ethyl groups, along with the sulfur-containing thieno[2,3-c]pyridine core, suggest that the molecule has a high degree of lipophilicity. This is likely to result in high permeability in the PAMPA assay, as the molecule can effectively interact with the lipid components of the artificial membrane.

Final answer: High permeability.

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# 65

**SMILES:** CCOC1=CC=C(C=C1)N2CC(CC2=O)C3=NC(=NO3)C4=CC=CC=N4

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound with several distinct structural features that influence its permeability in the PAMPA assay. Let's break down these features and their implications:

1. **Pyridine Ring**: The presence of a pyridine ring, which is a six-membered aromatic ring containing one nitrogen atom, contributes to the molecule's polarity and ability to participate in hydrogen bonding. This can enhance the molecule's solubility in aqueous environments, which is beneficial for permeability through biological membranes. The nitrogen atom can also act as a hydrogen bond acceptor, potentially interacting with the artificial membrane.

2. **Ethoxyphenyl Group**: The ethoxyphenyl moiety consists of a phenyl ring substituted with an ethoxy group. The phenyl ring is hydrophobic, which can facilitate interactions with the lipid components of the artificial membrane. The ethoxy group adds some degree of polarity, which can improve solubility and membrane permeability.

3. **Oxadiazole Ring**: The 1,2,4-oxadiazole ring is a five-membered heterocyclic compound containing two nitrogen atoms and one oxygen atom. This ring is known for its electron-withdrawing properties, which can influence the electronic distribution of the molecule. The oxadiazole ring can also participate in hydrogen bonding and dipole-dipole interactions, potentially enhancing the molecule's interaction with the membrane.

4. **Pyrrolidinone Ring**: The pyrrolidinone moiety is a five-membered lactam (cyclic amide) that contributes to the molecule's overall polarity. The presence of the carbonyl group in the lactam can form hydrogen bonds, which may facilitate interaction with the membrane.

Overall, the given molecule exhibits a balance of hydrophobic and hydrophilic properties due to its aromatic rings, heteroatoms, and functional groups. The combination of these features suggests that the molecule can effectively interact with the artificial membrane, potentially leading to high permeability. The presence of polar groups allows for hydrogen bonding and solubility in aqueous environments, while the aromatic and hydrophobic components facilitate interactions with the lipid components of the membrane.

Final answer: High permeability.

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# 66

**SMILES:** CC1=CC(=CC(=C1)NC2=NC(=CS2)C3=CC=C(O3)CNC(=O)C)C

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several functional groups and structural motifs that influence its permeability in the PAMPA assay. Let's break down the key structural elements and their impact on permeability:

1. **Thiazole Ring**: The presence of a thiazole ring, which is a five-membered heterocyclic compound containing both sulfur and nitrogen, is known to contribute to the molecule's ability to interact with biological membranes. Thiazole rings are often involved in hydrogen bonding and π-π interactions, which can enhance the molecule's ability to permeate through the artificial membrane.

2. **Aromatic Amine**: The given molecule contains a dimethyl-substituted aniline group, which is an aromatic amine. Aromatic amines can increase the lipophilicity of the molecule, enhancing its ability to traverse lipid membranes. However, they can also introduce some degree of polarity, which may affect the overall permeability.

3. **Furan Ring**: The furan ring, another five-membered heterocyclic compound, contributes to the molecule's aromatic character. Furans are relatively polar and can engage in π-π stacking interactions, which may facilitate membrane permeation. However, the presence of the furan ring can also introduce some steric hindrance, potentially affecting the molecule's ability to pass through the membrane.

4. **Amide Linkage**: The acetamide group in the given molecule is a polar functional group that can form hydrogen bonds with the artificial membrane. This can enhance the molecule's solubility in the membrane environment, potentially increasing its permeability. However, the amide linkage may also introduce some rigidity to the molecule, which could hinder its passage through the membrane.

Overall, the given molecule's structure suggests a balance between hydrophobic and hydrophilic interactions, with the aromatic and heterocyclic rings contributing to its lipophilicity and the amide group providing potential for hydrogen bonding. These features collectively suggest that the given molecule would exhibit high permeability in the PAMPA assay, as it is likely to effectively interact with the artificial membrane and traverse it efficiently.

Final answer: High permeability

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# 67

**SMILES:** CC1=CSC(=N1)NS(=O)(=O)C2=CC=C(C=C2)NCC3=C(C(=CC=C3)OC)O

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a sulfonamide, which is a class of compounds known for their antibacterial properties. The sulfonamide group is characterized by the presence of a sulfonyl functional group attached to an amine. This group is known to enhance the molecule's ability to interact with biological targets, such as enzymes or receptors, due to its polar nature and ability to form hydrogen bonds.

The structure of the given molecule includes a sulfonamide group attached to a benzene ring, which is further substituted with a methoxy group and a hydroxyphenyl group. The methoxy group is an electron-donating group, which can influence the electronic properties of the benzene ring, potentially affecting the molecule's interaction with the artificial membrane.

The hydroxyphenyl group contains a hydroxyl group, which is capable of forming hydrogen bonds, increasing the molecule's solubility and potentially enhancing its permeability through the membrane. The presence of this group can also contribute to the molecule's overall polarity, which is an important factor in determining its permeability.

Additionally, the thiazole ring in the molecule is a heterocyclic compound containing both sulfur and nitrogen atoms. This ring can contribute to the molecule's overall stability and ability to interact with biological membranes due to its aromatic nature and potential for hydrogen bonding.

Overall, the combination of these functional groups suggests that the given molecule may have moderate permeability through the artificial membrane. The sulfonamide group, along with the hydroxyphenyl and methoxy groups, likely contribute to the molecule's ability to interact with the membrane, while the thiazole ring may enhance its stability and binding affinity.

Final answer: Low-to-moderate permeability.

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# 68

**SMILES:** C1=CC\2=C(C=C1Cl)NC(=O)/C2=C/C3=CC(=C(C(=C3)Cl)O)Cl

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a derivative of the indole class, which is known for its aromatic heterocyclic structure. This particular molecule features a 3-chloro-4,5-dichloro-substituted phenyl ring attached to an indole core. The presence of chlorine atoms on the phenyl ring can significantly influence the molecule's lipophilicity, potentially enhancing its ability to interact with lipid membranes.

The indole core itself is a planar, aromatic structure that can facilitate interactions with biological membranes through π-π stacking and hydrophobic interactions. The presence of a hydroxyl group on the indole ring can also contribute to hydrogen bonding, which may affect the molecule's solubility and permeability.

The methylene bridge connecting the phenyl ring to the indole core introduces a degree of rigidity and planarity, which can influence the overall shape and size of the molecule. This structural feature may impact how the molecule fits into the artificial membrane, potentially affecting its permeability.

Overall, the combination of aromaticity, chlorine substituents, and the indole core suggests that the given molecule may exhibit moderate to high permeability in the PAMPA assay, as these features are generally associated with favorable interactions with lipid membranes.

Final answer: High permeability

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# 69

**SMILES:** C1=CC2=C(C(=C1)Cl)/C(=C\C3=CC(=C(C(=C3)Cl)O)Cl)/C(=O)N2

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a derivative of hydroxyphenylacetic acid, which is a structural motif known for its potential biological activity. In this molecule, the hydroxyphenylacetic acid core is modified with a dichloro substitution on the phenyl ring and a methylidene linkage to an indolinone moiety.

The permeability of the given molecule in the PAMPA assay can be influenced by several structural features:

1. **Hydrophobic and Hydrophilic Balance**: The presence of dichloro groups on the phenyl ring increases the hydrophobic character of the molecule, which can enhance its ability to interact with the lipid components of the artificial membrane. However, the hydroxy group contributes to the hydrophilicity, potentially improving solubility and interaction with the aqueous environment.

2. **Planar Structure**: The indolinone moiety and the conjugated system formed by the methylidene linkage provide a planar structure, which can facilitate passage through the membrane by allowing the molecule to align and insert itself more efficiently.

3. **Polar and Non-Polar Regions**: The combination of polar (hydroxy group) and non-polar (chloro and indolinone) regions allows the molecule to interact with both hydrophilic and hydrophobic parts of the membrane, potentially enhancing its permeability.

Overall, the given molecule is likely to exhibit moderate permeability due to the balance of hydrophobic and hydrophilic features, as well as the planar and polar nature of its structure. This balance allows it to interact effectively with the artificial membrane, making it suitable for further evaluation in drug discovery applications.

Final answer: Low-to-moderate permeability.

------
# 70

**SMILES:** C1=CC=C2C(=C1)C(=CC=N2)C(=O)NC3=CC=C(C=C3)S(=O)(=O)NC4=NC=CS4

**Label:** 0

**Predi:** 1

**Correct:** 0

# Response:
The given molecule is a complex organic compound that features several functional groups and aromatic systems, which influence its permeability in the PAMPA assay.

Firstly, the molecule contains a quinoline moiety, which is a bicyclic aromatic compound. Quinoline structures are known for their planar aromatic nature, which can facilitate interactions with the artificial membrane through π-π stacking and hydrophobic interactions. This can contribute to the molecule's permeability.

Additionally, the molecule has a sulfonamide group attached to a phenyl ring. Sulfonamides are polar functional groups that can form hydrogen bonds with the artificial membrane, potentially enhancing permeability by increasing solubility and interaction with the membrane.

The presence of an amide linkage in the molecule also plays a role in its permeability. Amides are generally polar and can participate in hydrogen bonding, which may aid in the molecule's interaction with the membrane.

The thiazole ring, another aromatic heterocycle, contributes to the molecule's overall aromatic character and can engage in additional π-π interactions with the membrane. The nitrogen and sulfur atoms in the thiazole ring can also participate in hydrogen bonding or dipole interactions, further influencing permeability.

Overall, the combination of aromatic systems and polar functional groups in the given molecule suggests that it would have moderate to high permeability in the PAMPA assay, as these features facilitate interactions with the artificial membrane while maintaining a balance between hydrophilic and hydrophobic properties.

Final answer: High permeability.

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# 71

**SMILES:** C1=CC=C(C=C1)C2=NC=CC(=C2)C(=O)NC3=CC=C(C=C3)S(=O)(=O)NC4=NC=CS4

**Label:** 0

**Predi:** 0

**Correct:** 1

# Response:
The given molecule is an aromatic amide, which suggests that it contains an amide functional group attached to an aromatic ring system. This structural feature is significant in determining the molecule's permeability.

The presence of the amide group contributes to the molecule's ability to form hydrogen bonds, which can enhance its interaction with the artificial membrane. However, the overall permeability will also depend on the balance between hydrophilic and lipophilic properties.

The molecule contains a phenyl group, which is a hydrophobic aromatic ring. This can facilitate the passage of the molecule through the lipid-like environment of the artificial membrane, contributing to its permeability.

Additionally, the pyridine and thiazole rings introduce heteroatoms (nitrogen and sulfur, respectively) into the aromatic system. These heteroatoms can participate in additional hydrogen bonding or dipole interactions with the membrane, potentially affecting the molecule's permeability.

The sulfonamide group, which is a sulfur-containing functional group, is known for its ability to enhance water solubility and can also participate in hydrogen bonding. This group may increase the molecule's interaction with the polar components of the artificial membrane, influencing its permeability.

Overall, the given molecule's aromatic nature, combined with its functional groups, suggests that it may have moderate permeability through the artificial membrane. The balance of hydrophilic and lipophilic properties, along with the potential for hydrogen bonding, will dictate its ability to permeate the membrane.

Final answer: Low-to-moderate permeability.

------
# 72

**SMILES:** CC1=CC=C(C=C1)S(=O)(=O)NC2=C(C=CN=C2)C(=O)NC3=CC=C(C=C3)C4=NNN=N4

**Label:** 0

**Predi:** 0

**Correct:** 1

# Response:
The given molecule is a complex aromatic amide with several functional groups that influence its permeability in the PAMPA assay. Let's break down the structural features and their impact on permeability:

1. **Aromatic Rings**: The molecule contains multiple aromatic rings, including a pyridine ring, a phenyl ring, and a tetrazole ring. Aromatic rings generally contribute to lipophilicity, which can enhance the molecule's ability to permeate through lipid membranes. However, the presence of these rings also means the molecule may have a relatively high molecular weight and size, which can hinder permeability.

2. **Amide Linkage**: The amide group in the molecule is a polar functional group that can form hydrogen bonds with the artificial membrane. This can increase the molecule's interaction with the membrane, potentially enhancing permeability. However, the amide linkage also adds to the overall polarity of the molecule, which can be a double-edged sword. While it may facilitate some interactions with the membrane, it may also limit permeability due to increased solubility in aqueous environments.

3. **Sulfonamide Group**: The presence of a sulfonamide group, which is a combination of a sulfonyl group attached to an amine, introduces additional polarity and the potential for hydrogen bonding. This group can enhance the molecule's solubility in water, which might reduce permeability through the lipid-rich artificial membrane.

4. **Tetrazole Ring**: The tetrazole ring is a heterocyclic aromatic compound that can contribute to the molecule's overall stability and rigidity. While it may enhance lipophilicity, the tetrazole's presence can also introduce steric hindrance, potentially limiting the molecule's ability to fit through the membrane.

Overall, the given molecule's permeability in the PAMPA assay is likely to be moderate. The balance between its lipophilic aromatic rings and polar functional groups, such as the amide and sulfonamide, suggests that while it may have some ability to permeate the artificial membrane, its size and polarity may limit its overall permeability.

Final answer: Low-to-moderate permeability.

------
# 73

**SMILES:** COC1=CC=CC(=C1O)CNC2=CC=C(C=C2)S(=O)(=O)NC3=CC=C(C=C3)N4CCNCC4

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a sulfonamide, which is a class of compounds known for their antibacterial properties. The sulfonamide group is characterized by the presence of a sulfonyl functional group attached to an amine. This group is known to enhance the molecule's ability to interact with biological targets, such as enzymes or receptors, due to its polar nature and ability to form hydrogen bonds.

In the context of the Parallel Artificial Membrane Permeability Assay (PAMPA), the permeability of the given molecule is influenced by several structural features:

1. **Aromatic Rings**: The molecule contains multiple aromatic rings, which can enhance lipophilicity. Aromatic rings are known to facilitate membrane permeability due to their ability to interact with lipid bilayers through π-π interactions and van der Waals forces.

2. **Sulfonamide Group**: The presence of the sulfonamide group contributes to the molecule's polarity and ability to form hydrogen bonds. This can enhance solubility in aqueous environments, which is important for permeability across biological membranes.

3. **Hydroxyl Group**: The hydroxyl group in the molecule can also form hydrogen bonds, which may increase the molecule's solubility and permeability. This group can interact with polar sites on the membrane, potentially facilitating transport.

4. **Amino Groups**: The presence of amino groups, particularly the secondary amine linked to the piperazine ring, can increase the basicity of the molecule. This can affect the molecule's ionization state, which is crucial for permeability as it influences the molecule's ability to cross lipid membranes.

5. **Piperazine Ring**: The piperazine ring is a flexible moiety that can enhance the molecule's ability to fit into various binding sites, potentially increasing its permeability by allowing it to adopt conformations that are favorable for membrane passage.

Overall, the combination of these structural features suggests that the given molecule likely exhibits high permeability in the PAMPA assay. The balance of hydrophilic and lipophilic properties, along with the ability to form hydrogen bonds and interact with lipid membranes, supports its potential to traverse the artificial membrane efficiently.

Final answer: High permeability

------
# 74

**SMILES:** C1CN(CCN1)C2=CC=C(C=C2)N[S+](=O)(C3=CC=C(C=C3)NCC4=C(C(=CC=C4)Cl)O)[O-]

**Label:** 0

**Predi:** 1

**Correct:** 0

# Response:
The given molecule is a sulfonamide, which is a class of compounds known for their antibacterial properties. The sulfonamide group is characterized by the presence of a sulfonyl functional group attached to an amine. This group is known to enhance the molecule's ability to interact with biological membranes, which can influence its permeability.

In the given molecule, the presence of the sulfonamide group suggests that it may have moderate to high permeability through the artificial membrane. This is because sulfonamides are generally polar and can form hydrogen bonds, which can facilitate their passage through the membrane.

Additionally, the molecule contains aromatic rings, such as phenyl groups, which can contribute to its lipophilicity. This lipophilicity can enhance the molecule's ability to permeate through lipid-rich membranes, such as the artificial membrane used in the PAMPA assay.

The presence of a chloro substituent on one of the phenyl rings can also influence the molecule's permeability. Chlorine atoms can increase the lipophilicity of the molecule, potentially enhancing its ability to permeate the membrane.

Furthermore, the molecule contains a piperazine ring, which is a common motif in many pharmaceuticals. Piperazine can increase the solubility of the molecule, which can also contribute to its permeability.

Overall, the combination of these functional groups suggests that the given molecule likely has high permeability to the artificial membrane, as it possesses a balance of polar and non-polar characteristics that facilitate membrane interaction.

Final answer: High permeability.

------
# 75

**SMILES:** C1=CC=C2C=C(C=CC2=C1)CC(=O)NC3=CC=C(C=C3)S(=O)(=O)NC4=NC=CS4

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a complex organic compound that includes several functional groups and aromatic rings, which influence its permeability in the PAMPA assay.

1. **Aromatic Rings**: The molecule contains a naphthalene moiety and a thiazole ring. These aromatic systems contribute to the molecule's hydrophobic character, which can enhance its ability to permeate through the lipid-like environment of the artificial membrane. Aromatic rings often facilitate interactions with the membrane through π-π stacking and van der Waals forces.

2. **Sulfamoyl Group**: The presence of the sulfamoyl group attached to the naphthalene ring introduces a polar and potentially ionizable site. This group can form hydrogen bonds with the membrane, which may enhance or hinder permeability depending on the balance between hydrophilic and hydrophobic interactions.

3. **Thiazole Ring**: The thiazole ring is a heterocyclic aromatic compound that can contribute to the molecule's overall stability and rigidity. The nitrogen and sulfur atoms in the thiazole ring can participate in hydrogen bonding and other polar interactions, which may affect the molecule's permeability.

4. **Amide Linkage**: The sulfamoyl group is connected to an amide linkage, which is a common feature in many bioactive molecules. Amides can form hydrogen bonds, which may influence the molecule's solubility and permeability. The amide linkage can also contribute to the overall stability of the molecule in the membrane environment.

Overall, the given molecule's structure suggests that it has a balance of hydrophobic and hydrophilic properties, which is typical for molecules with moderate permeability in PAMPA assays. The aromatic rings and heterocycles provide hydrophobic interactions, while the sulfamoyl and amide groups offer polar interactions. This combination of features likely results in moderate permeability, allowing the molecule to traverse the artificial membrane but not excessively so.

Final answer: Low-to-moderate permeability.

------
# 76

**SMILES:** C1CNCCC1C2=CC=C(C=C2)N[S+](=O)(C3=CC=C(C=C3)NCC4=C(C=C(C=C4)Br)O)[O-]

**Label:** 0

**Predi:** 1

**Correct:** 0

# Response:
The given molecule is a sulfonamide, which is a class of compounds known for their antibacterial properties. The sulfonamide group is characterized by the presence of a sulfonyl functional group attached to an amine. This functional group is known to enhance the molecule's ability to interact with biological membranes, which can influence its permeability.

The structure of the given molecule includes several key features that contribute to its permeability:

1. **Aromatic Rings**: The molecule contains multiple aromatic rings, including a phenyl group and a substituted phenyl group. Aromatic rings can enhance the lipophilicity of the molecule, which often increases its ability to permeate lipid membranes.

2. **Bromo Substitution**: The presence of a bromine atom on one of the phenyl rings can increase the molecule's lipophilicity and potentially enhance its ability to interact with lipid bilayers. Halogen atoms like bromine can also participate in halogen bonding, which may influence the molecule's binding interactions with the artificial membrane.

3. **Sulfonamide Group**: The sulfonamide moiety is known for its ability to form hydrogen bonds, which can facilitate interactions with the artificial membrane. This group can also contribute to the molecule's overall polarity, which can affect its permeability.

4. **Hydroxyl Group**: The hydroxyl group on the phenyl ring can form hydrogen bonds with the artificial membrane, potentially increasing the molecule's affinity for the membrane and enhancing its permeability.

5. **Piperidine Ring**: The piperidine moiety is a common structural feature in many pharmaceuticals, and its presence can influence the molecule's overall conformation and flexibility. This can affect how the molecule interacts with the artificial membrane.

Overall, the combination of these structural features suggests that the given molecule likely has high permeability in the PAMPA assay. The aromatic rings and halogen substitution contribute to lipophilicity, while the sulfonamide and hydroxyl groups enhance hydrogen bonding interactions with the membrane. These factors collectively facilitate the molecule's passage through the artificial membrane.

Final answer: High permeability

------
# 77

**SMILES:** C1CNCCC1C2=CC=C(C=C2)N[S+](=O)(C3=CC=C(C=C3)NCC4=C(C=C(C=C4)Cl)O)[O-]

**Label:** 0

**Predi:** 0

**Correct:** 1

# Response:
The given molecule is a sulfonamide, which is a class of compounds known for their antibacterial properties. The sulfonamide group is characterized by the presence of a sulfonyl functional group attached to an amine. This group is known to enhance the molecule's ability to interact with biological targets, often through hydrogen bonding and ionic interactions.

The molecule contains a phenyl ring substituted with a sulfonamide group, which is a common feature in many pharmaceuticals due to its ability to improve solubility and permeability. The sulfonamide group can increase the molecule's polarity, which may enhance its ability to permeate biological membranes.

Additionally, the molecule has a chloro-substituted phenyl ring, which can influence its lipophilicity. The presence of the chlorine atom can increase the molecule's hydrophobic character, potentially affecting its permeability by enhancing its ability to interact with lipid membranes.

The molecule also contains a hydroxyphenyl group, which can contribute to its overall polarity and ability to form hydrogen bonds. This group may enhance the molecule's solubility in aqueous environments, which is beneficial for permeability across biological membranes.

The piperidinyl group, a six-membered nitrogen-containing ring, is a common structural motif in many drugs. It can increase the molecule's basicity and enhance its ability to interact with biological targets through ionic interactions.

Overall, the combination of these functional groups suggests that the given molecule may have moderate permeability due to the balance of hydrophilic and hydrophobic properties. The sulfonamide group and hydroxyphenyl group contribute to its solubility and potential for hydrogen bonding, while the chloro-substituted phenyl ring and piperidinyl group may enhance its lipophilicity and ability to interact with lipid membranes.

Final answer: Low-to-moderate permeability.

------
# 78

**SMILES:** CC1=C(C(=NO1)C)C2=C(C=C3C(=C2)N=CC4=C3N(C(=O)N4)[C@H](C)C5=CC=CC=N5)OC

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex structure that includes several functional groups and aromatic systems, which contribute to its permeability characteristics in the PAMPA assay. 

The molecule contains an imidazoquinoline core, which is a fused heterocyclic system. This core is known for its planar structure, which can facilitate interactions with the artificial membrane, potentially enhancing permeability. The presence of nitrogen atoms in the imidazoquinoline can also contribute to hydrogen bonding and ionic interactions, which may influence the molecule's ability to permeate the membrane.

Additionally, the molecule has a pyridine ring substituted with a methoxy group. The methoxy group is an electron-donating group, which can increase the lipophilicity of the molecule, enhancing its ability to traverse lipid membranes. The pyridine ring itself is a basic heterocycle, which can participate in π-π stacking interactions with the membrane, further aiding in permeability.

The presence of a methyl-substituted thiophene ring adds to the lipophilic character of the molecule, which is beneficial for membrane permeability. Thiophene rings are known for their aromatic stability and can engage in π-π interactions, which may facilitate the passage of the molecule through the membrane.

Overall, the combination of these aromatic and heterocyclic systems, along with the electron-donating methoxy group, suggests that the given molecule would exhibit high permeability in the PAMPA assay. The structural features promote lipophilicity and facilitate interactions with the artificial membrane, enhancing its ability to permeate.

Final answer: High permeability.

------
# 79

**SMILES:** CC(C)(C)C1=CC=C(C=C1)C(=O)NC2=CN3C=C(C=CC3=N2)N4C=CN=C4

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound with several distinct structural features that influence its permeability in the PAMPA assay. Let's break down these features and their implications:

1. **Imidazo[1,2-a]pyridine Core**: This bicyclic structure is known for its planar and aromatic characteristics, which can enhance the molecule's ability to interact with the artificial membrane through π-π stacking interactions. This can contribute to moderate to high permeability, as the aromatic rings can facilitate passage through the membrane.

2. **Pyrazole Ring**: The presence of a pyrazole ring, which is a five-membered heterocycle containing two nitrogen atoms, can also contribute to the molecule's ability to permeate the membrane. The nitrogen atoms can participate in hydrogen bonding, which may enhance solubility and permeability.

3. **Tert-Butyl Group**: The tert-butyl group is a bulky, hydrophobic moiety that can increase the lipophilicity of the molecule. This can enhance membrane permeability by increasing the molecule's ability to dissolve in the lipid bilayer of the artificial membrane.

4. **Benzamide Moiety**: The benzamide group introduces an amide linkage, which can participate in hydrogen bonding. This can affect the molecule's solubility and permeability, potentially increasing its ability to permeate the membrane due to favorable interactions with the membrane's polar head groups.

Overall, the given molecule's combination of aromatic rings, heterocycles, and hydrophobic groups suggests that it would exhibit high permeability in the PAMPA assay. The aromatic and heterocyclic components facilitate interactions with the membrane, while the tert-butyl group enhances lipophilicity, contributing to its ability to permeate the artificial membrane.

Final answer: High permeability

------
# 80

**SMILES:** COC1=CC=CC(=C1O)CNC2=CC=C(C=C2)S(=O)(=O)NC3=NC=C(S3)C4=CC=CC=C4

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a sulfonamide, which is a class of compounds known for their antibacterial properties. The sulfonamide group is characterized by the presence of a sulfonyl functional group attached to an amine. This group is known to enhance the molecule's ability to interact with biological targets, such as enzymes or receptors, due to its polar nature and ability to form hydrogen bonds.

The molecule also contains a thiazole ring, which is a five-membered heterocyclic compound containing both sulfur and nitrogen. Thiazole rings are often found in bioactive molecules and can contribute to the molecule's ability to permeate biological membranes due to their planar structure and potential for pi-stacking interactions.

Additionally, the molecule features a methoxyphenyl group, which is a phenyl ring substituted with a methoxy group. The methoxy group can increase the lipophilicity of the molecule, potentially enhancing its ability to permeate lipid membranes.

The phenyl group attached to the thiazole ring and the sulfonamide group can also contribute to the molecule's overall hydrophobic character, which may facilitate its passage through lipid bilayers.

Overall, the combination of these functional groups suggests that the given molecule may have moderate permeability through the artificial membrane, as the sulfonamide and thiazole groups provide a balance of hydrophilic and hydrophobic properties that can aid in membrane permeation. However, the exact permeability would depend on the specific conditions of the PAMPA assay, such as the type of membrane used and the presence of other molecules that may influence permeability.

Final answer: Low-to-moderate permeability.

------
# 81

**SMILES:** COC1=CC=CC(=C1O)CNC2=CC=C(C=C2)S(=O)(=O)NC3=NC4=CC=CC=C4O3

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a sulfonamide, which is a class of compounds known for their antibacterial properties. The sulfonamide group is characterized by the presence of a sulfonyl functional group attached to an amine. This group is known to enhance the molecule's ability to interact with biological targets, such as enzymes or receptors, due to its polar nature and ability to form hydrogen bonds.

The molecule also contains a benzoxazole moiety, which is a bicyclic structure consisting of a benzene ring fused to an oxazole ring. This moiety is often associated with increased stability and bioavailability, as it can enhance the lipophilicity of the molecule, allowing it to better penetrate lipid membranes.

Additionally, the presence of a methoxy group on the phenyl ring contributes to the molecule's overall lipophilicity, which can further enhance its ability to permeate through lipid-rich environments, such as cell membranes.

The combination of these functional groups suggests that the given molecule has a balance of hydrophilic and lipophilic properties, which is often desirable for good permeability. The sulfonamide group provides the necessary polar characteristics for interaction with aqueous environments, while the benzoxazole and methoxy groups contribute to its lipophilicity, enhancing its ability to permeate lipid membranes.

Therefore, based on the structural features of the given molecule, it is likely to exhibit high permeability in the Parallel Artificial Membrane Permeability Assay (PAMPA).

Final answer: High permeability

------
# 82

**SMILES:** C1=CC=C(C(=C1)S(=O)(=O)NC2=C(C=CN=C2)C(=O)NC3=NC(=CS3)C4=CC=C(C=C4)F)Cl

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound with several functional groups and aromatic rings that influence its permeability in the PAMPA assay. Let's break down the structural features and their impact on permeability:

1. **Aromatic Rings**: The molecule contains multiple aromatic rings, including a phenyl ring, a thiazole ring, and a pyridine ring. Aromatic rings generally contribute to lipophilicity, which can enhance the molecule's ability to permeate through lipid membranes. However, the presence of these rings also depends on the specific substituents attached to them.

2. **Sulfonamide Group**: The sulfonamide group is known for its polar nature, which can increase the molecule's solubility in water. This group can form hydrogen bonds with the artificial membrane, potentially enhancing permeability. However, its polar nature might also limit permeability if it causes the molecule to interact too strongly with the membrane, leading to a more rigid conformation.

3. **Chloro and Fluoro Substituents**: The chloro and fluoro groups on the phenyl ring increase the molecule's lipophilicity, which can enhance membrane permeability. These halogen atoms can also participate in halogen bonding, which might influence the interaction with the artificial membrane.

4. **Thiazole Ring**: The thiazole ring is a heterocyclic compound that can contribute to the molecule's overall stability and rigidity. It may also play a role in the molecule's electronic properties, potentially affecting its interaction with the membrane.

5. **Carboxamide Group**: The carboxamide group is another polar functional group that can form hydrogen bonds. This group can enhance solubility and permeability, but similar to the sulfonamide group, it might also cause the molecule to interact too strongly with the membrane.

Overall, the given molecule has a balance of lipophilic and polar characteristics due to its aromatic rings and various functional groups. The presence of halogen substituents and heterocyclic rings suggests that the molecule may have moderate to high permeability in the PAMPA assay, as these features can facilitate interactions with the lipid components of the artificial membrane while maintaining sufficient solubility.

Final answer: High permeability

------
# 83

**SMILES:** C1=CC=C2C(=C1)C(=NC(=N2)C3=CC=NC=C3)NC4=CC(=C(C=C4)C5=CC(=CC=C5)OC(F)(F)F)F

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a quinazoline derivative, which is a class of compounds known for their potential biological activity, particularly in the realm of kinase inhibition. The structure of the given molecule includes several key features that influence its permeability:

1. **Quinazoline Core**: The quinazoline moiety is a bicyclic structure that is relatively planar and aromatic. This core is known for its ability to interact with biological targets through π-π stacking and hydrogen bonding, which can enhance the molecule's ability to permeate biological membranes.

2. **Aromatic Rings**: The presence of multiple aromatic rings, including a phenyl group and a pyridine ring, contributes to the molecule's lipophilicity. Aromatic rings can enhance membrane permeability by increasing the molecule's ability to interact with the lipid bilayer of cell membranes.

3. **Fluorine Atoms**: The trifluoromethoxy group and the fluorine atom on the phenyl ring introduce electron-withdrawing properties, which can affect the molecule's overall polarity and solubility. Fluorine atoms can also enhance metabolic stability and membrane permeability by increasing the molecule's lipophilicity.

4. **Amino Group**: The presence of an amine group on the quinazoline ring can form hydrogen bonds with the membrane, potentially aiding in permeation. However, it can also introduce some degree of polarity, which might reduce permeability in certain environments.

Overall, the combination of aromatic rings, fluorine substituents, and the quinazoline core suggests that the given molecule likely exhibits high permeability in the PAMPA assay. The balance of lipophilic and polar features allows it to effectively interact with the artificial membrane, facilitating its passage through the membrane.

Final answer: High permeability

------
# 84

**SMILES:** C1CCN(CC1)CCOC2=CC=CC(=C2)C3=NNC4=C3C=C(C=C4)C5=NC=NN5

**Label:** 0

**Predi:** 1

**Correct:** 0

# Response:
The given molecule is a complex organic compound with several functional groups and aromatic rings, which contribute to its permeability characteristics in the PAMPA assay.

1. **Aromatic Rings**: The molecule contains multiple aromatic rings, including a phenyl group and an indazole moiety. Aromatic rings are generally hydrophobic, which can enhance the molecule's ability to interact with the hydrophobic regions of the artificial membrane. This interaction can facilitate the passage of the molecule through the membrane, indicating a potential for high permeability.

2. **Triazole Ring**: The presence of a triazole ring introduces nitrogen atoms into the structure, which can participate in hydrogen bonding and other polar interactions. This can affect the molecule's solubility and permeability, potentially increasing its ability to interact with the polar regions of the membrane. However, the overall effect on permeability will depend on the balance between hydrophobic and hydrophilic interactions.

3. **Piperidine Group**: The piperidine moiety is a secondary amine, which can enhance the molecule's solubility in water due to its basic nature. This group can also participate in hydrogen bonding, which may facilitate interaction with the membrane. The presence of the piperidine group can contribute to moderate permeability, as it provides a balance between hydrophilic and hydrophobic properties.

4. **Methoxy Linkage**: The methoxy group acts as a linker between the phenyl ring and the piperidine moiety. This ether linkage can influence the molecule's flexibility and overall conformation, potentially affecting its ability to fit into the membrane's structure. The presence of the methoxy group can also impact the molecule's lipophilicity, which may enhance permeability.

Overall, the given molecule's structure suggests that it has a combination of hydrophobic and hydrophilic characteristics, which can facilitate its passage through the artificial membrane. The aromatic rings and the triazole moiety contribute to hydrophobic interactions, while the piperidine group and methoxy linkage provide hydrophilic properties. This balance suggests that the molecule may exhibit high permeability in the PAMPA assay.

Final answer: High permeability

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# 85

**SMILES:** CC[C@@H](C(=O)N1C[C@H](C[C@@H]1CC2=C(NC3=C2C=CC(=C3)F)C4=C(C5=C(N4)C=C(C=C5)F)C[C@@H]6C[C@@H](CN6C(=O)[C@H](CC)NC(=O)[C@H](C)NC)O)O)NC(=O)[C@H](C)NC

**Label:** 0

**Predi:** 0

**Correct:** 1

# Response:
The given molecule is a complex organic compound with multiple functional groups and structural features that influence its permeability in the PAMPA assay. Let's analyze these features:

1. **Fluorinated Aromatic Ring**: The presence of a difluoro-substituted indole ring suggests that the molecule has increased lipophilicity, which can enhance its ability to permeate lipid membranes. Fluorine atoms can also influence the electronic properties of the aromatic ring, potentially affecting the molecule's interaction with the artificial membrane.

2. **Hydroxyl Groups**: The hydroxyl groups present in the molecule can form hydrogen bonds with the artificial membrane, potentially increasing its interaction with the membrane and enhancing permeability. However, these groups can also introduce some polarity, which might limit permeability depending on the balance with other hydrophobic regions.

3. **Amide Linkages**: The molecule contains multiple amide linkages, which are polar and can form hydrogen bonds. These linkages can contribute to the molecule's solubility in aqueous environments, but they may also hinder permeability due to their polar nature.

4. **Cyclopentyl and Indole Structures**: The cyclopentyl and indole structures provide rigidity and bulk to the molecule, which can affect its ability to fit into the membrane pores. The indole structure, in particular, is a common motif in bioactive compounds and may interact with the membrane through π-π interactions or other non-covalent interactions.

5. **Methylamino and Carbonyl Groups**: The methylamino group can increase the basicity of the molecule, potentially affecting its interaction with the membrane. The carbonyl groups, being polar, can also participate in hydrogen bonding, which may influence the molecule's orientation and interaction with the membrane.

Overall, the given molecule's structure suggests a balance between hydrophobic and hydrophilic properties, with several functional groups that can interact with the artificial membrane. The presence of fluorine, aromatic rings, and multiple amide linkages likely contribute to moderate permeability, allowing the molecule to traverse the membrane while still interacting with the membrane's components. Therefore, the given molecule is likely to exhibit low-to-moderate permeability in the PAMPA assay.

Final answer: Low-to-moderate permeability.

------
# 86

**SMILES:** CN(C)CCN1C(=O)C2=CC=CC3=CC(=CC(=C32)C1=O)N

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a member of the isoquinoline family, which is known for its aromatic and heterocyclic structure. The core structure of the molecule is a benzo[de]isoquinoline, which is a fused bicyclic system consisting of a benzene ring and an isoquinoline ring. This structure contributes to the molecule's rigidity and planarity, which can influence its interaction with the artificial membrane.

The presence of an amino group on the isoquinoline ring introduces a polar functional group, which can form hydrogen bonds with the membrane. This can enhance the molecule's solubility in aqueous environments and potentially increase its permeability through the membrane.

Additionally, the molecule contains a 2-(dimethylamino)ethyl side chain. The dimethylamino group is a basic moiety that can be protonated under physiological conditions, increasing the molecule's overall polarity and water solubility. This can facilitate its passage through the membrane by allowing it to interact favorably with the polar head groups of the artificial membrane.

The dione functionality in the isoquinoline ring system can also contribute to the molecule's overall polarity and reactivity. The carbonyl groups can participate in hydrogen bonding and dipole-dipole interactions, which may further enhance the molecule's permeability.

Overall, the combination of aromaticity, polar functional groups, and basic side chains suggests that the given molecule would exhibit high permeability in the Parallel Artificial Membrane Permeability Assay (PAMPA).

Final answer: High permeability

------
# 87

**SMILES:** C1CNCCC1(C2=CC=C(C=C2)C3=CNN=C3)C4=CC=C(C=C4)Cl

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a member of the pyrazole class, which is characterized by a five-membered ring containing two adjacent nitrogen atoms. This structural feature is often associated with various biological activities, including anti-inflammatory and analgesic properties.

In the context of the Parallel Artificial Membrane Permeability Assay (PAMPA), the molecule's permeability is influenced by its structural components. The presence of the pyrazole ring contributes to the molecule's overall lipophilicity, which can enhance its ability to permeate lipid membranes. However, the molecule also contains a 4-chlorophenyl group, which can introduce steric hindrance and affect the molecule's overall shape and size. This may reduce its permeability by limiting its ability to fit through the membrane pores.

Additionally, the phenylpyridine moiety can contribute to the molecule's polarity and hydrogen bonding potential, which may also impact its permeability. The balance between lipophilicity and polarity is crucial in determining the molecule's permeability.

Overall, the given molecule's structural features suggest that it may have moderate permeability due to the interplay between its lipophilic and polar components. However, the specific outcome would depend on the exact nature of the artificial membrane used in the PAMPA assay.

Final answer: Low-to-moderate permeability.

------
# 88

**SMILES:** CN1C2=CN=C3C=CC(=CC3=C2N(C1=O)C4=CC(=C(C=C4)N5CCNCC5)C(F)(F)F)C6=CN=C(C=C6)OC

**Label:** 0

**Predi:** 1

**Correct:** 0

# Response:
The given molecule is a complex organic compound with several functional groups and aromatic rings, which contribute to its permeability characteristics in the PAMPA assay. 

The molecule contains an imidazoquinoline core, which is a fused bicyclic structure combining an imidazole and a quinoline ring. This core is known for its planar aromatic structure, which can facilitate interactions with the artificial membrane, potentially enhancing permeability due to π-π stacking interactions with the membrane's aromatic residues.

Additionally, the presence of a trifluoromethyl group on the quinoline ring introduces electron-withdrawing properties, which can influence the molecule's lipophilicity. This group can enhance the molecule's ability to penetrate lipid membranes by increasing its overall hydrophobic character.

The molecule also features a piperazine ring, which is a common motif in pharmaceuticals due to its basic nitrogen atoms. This can enhance solubility and permeability by forming hydrogen bonds or ionic interactions with the membrane, depending on the pH of the environment.

The methoxyphenyl group contributes to the molecule's overall lipophilicity and can also participate in hydrophobic interactions with the membrane. The presence of the methoxy group can also influence the electronic properties of the phenyl ring, potentially affecting the molecule's binding affinity to the membrane.

Overall, the combination of these structural features suggests that the given molecule likely exhibits high permeability in the PAMPA assay due to its aromatic, lipophilic, and basic characteristics, which facilitate interactions with the artificial membrane.

Final answer: High permeability.

------
# 89

**SMILES:** C1=CC=C(C=C1)C2=NC=C(N2)C(=O)NC3=NC=C(S3)CC4=CC=C(C=C4)C(F)(F)F

**Label:** 0

**Predi:** 1

**Correct:** 0

# Response:
The given molecule is a complex organic compound that features several distinct functional groups and structural motifs, each contributing to its permeability characteristics in the PAMPA assay.

1. **Trifluoromethylphenyl Group**: The presence of a trifluoromethyl group attached to a phenyl ring significantly influences the molecule's lipophilicity. The trifluoromethyl group is highly electronegative and lipophilic, which can enhance the molecule's ability to interact with lipid membranes. This group can increase the overall hydrophobic character of the molecule, potentially improving its permeability through the artificial membrane.

2. **Phenyl Group**: The phenyl group contributes to the overall hydrophobicity of the molecule. Aromatic rings like phenyl groups can engage in π-π interactions with the lipid bilayer of the artificial membrane, which may facilitate passage through the membrane.

3. **Thiazole Ring**: The thiazole ring is a heterocyclic compound containing both sulfur and nitrogen. This ring can participate in hydrogen bonding and other polar interactions, which may affect the molecule's solubility and permeability. The presence of the thiazole ring can also influence the electronic properties of the molecule, potentially affecting its interaction with the membrane.

4. **Imidazole Ring**: The imidazole ring is another heterocyclic component that can engage in hydrogen bonding and other polar interactions. Imidazole rings are known for their ability to participate in acid-base chemistry, which can be relevant in biological environments. The presence of this ring may also contribute to the molecule's overall polarity and solubility, impacting its permeability.

5. **Carboxamide Group**: The carboxamide group is a polar functional group that can form hydrogen bonds. This group can increase the molecule's solubility in aqueous environments, which may affect its permeability. However, the balance between hydrophilic and hydrophobic interactions will determine the overall permeability.

In summary, the given molecule's structure suggests a balance between hydrophobic and hydrophilic properties. The trifluoromethylphenyl group and phenyl group contribute to lipophilicity, enhancing membrane permeability, while the thiazole and imidazole rings, along with the carboxamide group, introduce polar characteristics that may facilitate interactions with the artificial membrane. Overall, the molecule is likely to exhibit high permeability in the PAMPA assay due to its balanced hydrophobic and hydrophilic features.

Final answer: High permeability

------
# 90

**SMILES:** CC1=C(NC(=C1C(=O)C)C)C(=O)NC2=CC(=C(C=C2)OC)[S+](=O)(NC3=CC=CC=C3C#N)[O-]

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a sulfonamide, which is a class of compounds known for their antibacterial properties. The sulfonamide group is characterized by the presence of a sulfonyl functional group attached to an amine. This group is known to enhance the molecule's ability to interact with biological targets, often through hydrogen bonding and ionic interactions.

In the given molecule, the sulfonamide group is attached to a phenyl ring, which is further substituted with an acetyl group. This acetyl group can increase the molecule's lipophilicity, potentially enhancing its ability to permeate lipid membranes.

The molecule also contains a methoxy group on the phenyl ring, which can influence its electronic properties and potentially improve membrane permeability by increasing the molecule's overall hydrophobicity.

Additionally, the molecule features a pyrrole ring with a methyl group and a carboxamide group. The presence of the carboxamide group can contribute to hydrogen bonding, which may facilitate interactions with the artificial membrane.

Overall, the combination of these functional groups suggests that the given molecule may have moderate permeability to the artificial membrane, as the balance of hydrophilic and hydrophobic groups can facilitate passage through the membrane while maintaining sufficient interaction with the membrane's components.

Final answer: Low-to-moderate permeability.

------
# 91

**SMILES:** C1=CC(=CC(=C1)C(=O)NCCO)C2=CC(=NC=N2)NC3=CC=C(C=C3)OC(F)(F)F

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a complex organic compound that includes several functional groups and structural features that influence its permeability in the PAMPA assay. Let's break down these features and their impact on permeability:

1. **Aromatic Rings**: The molecule contains multiple aromatic rings, including a pyrimidine ring and an aniline moiety. Aromatic rings are generally hydrophobic, which can enhance the molecule's ability to interact with the hydrophobic regions of the artificial membrane. This interaction can facilitate permeation through the membrane.

2. **Trifluoromethoxy Group**: The presence of a trifluoromethoxy group on the aniline moiety introduces a highly electronegative and lipophilic character. The trifluoromethoxy group can increase the molecule's lipophilicity, which may enhance its ability to permeate the membrane by increasing its solubility in lipid environments.

3. **Hydroxyethyl Group**: The hydroxyethyl group contributes to the molecule's hydrophilicity. This group can form hydrogen bonds with the membrane, potentially aiding in the molecule's interaction with the membrane and influencing its permeability.

4. **Amide Linkage**: The amide linkage in the benzamide portion of the molecule can participate in hydrogen bonding, which may affect the molecule's orientation and interaction with the membrane. Amide bonds are relatively stable and can contribute to the overall rigidity of the molecule, which may influence its permeability.

5. **Pyrimidine Ring**: The pyrimidine ring is a heterocyclic aromatic compound that can interact with the membrane through π-π stacking interactions. This can enhance the molecule's ability to permeate the membrane.

Overall, the given molecule's combination of aromatic rings, hydrophilic and hydrophobic groups, and the presence of functional groups capable of hydrogen bonding suggest that it would have a balance of hydrophobic and hydrophilic interactions with the artificial membrane. This balance typically results in moderate permeability, as the molecule can interact with both the hydrophobic and hydrophilic components of the membrane. Therefore, the given molecule is likely to exhibit low-to-moderate permeability in the PAMPA assay.

Final answer: Low-to-moderate permeability.

------
# 92

**SMILES:** CC1=C(NC(=C1C(=O)C)C)C(=O)NC2=CC(=C(C=C2)OCCCN(C)C)[S+](=O)(NC3=CC=C(C=C3)Br)[O-]

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several functional groups and structural elements that influence its permeability in the PAMPA assay. Let's break down these features and their impact on permeability:

1. **Pyrrole Ring**: The presence of a pyrrole ring, which is a five-membered aromatic heterocycle containing nitrogen, contributes to the molecule's overall aromaticity and planarity. This can enhance the molecule's ability to interact with the artificial membrane, potentially increasing its permeability.

2. **Acetyl Group**: The acetyl group attached to the pyrrole ring introduces a polar carbonyl group, which can form hydrogen bonds with the membrane. This can increase the molecule's solubility in the membrane environment, potentially enhancing its permeability.

3. **Dimethyl Substitution**: The dimethyl groups on the pyrrole ring increase the hydrophobic character of the molecule. This can facilitate interactions with the hydrophobic regions of the artificial membrane, potentially improving permeability.

4. **Aromatic Amide Linkage**: The amide linkage connects the pyrrole ring to a phenyl group. Amides are generally polar and can participate in hydrogen bonding, which may aid in membrane interaction and permeability.

5. **Bromophenyl Group**: The presence of a bromine atom on the phenyl group introduces a bulky, electron-withdrawing substituent. This can affect the electronic distribution in the molecule, potentially influencing its interaction with the membrane. The bromine atom can also enhance lipophilicity, which may improve permeability.

6. **Dimethylaminoethoxy Group**: This group introduces a tertiary amine, which is basic and can form ionic interactions with the membrane. The ethoxy linkage provides flexibility and increases the molecule's overall hydrophilicity, which can enhance solubility and permeability.

7. **Sulfamoyl Group**: The sulfamoyl group is a sulfonamide derivative, which is polar and can form hydrogen bonds. This group can increase the molecule's solubility in aqueous environments and may enhance permeability through the membrane.

Overall, the given molecule contains a balance of hydrophobic and hydrophilic features, aromatic and polar groups, which suggest that it may have moderate to high permeability in the PAMPA assay. The combination of aromaticity, flexibility, and the presence of polar functional groups likely facilitate interactions with the artificial membrane, promoting permeability.

Final answer: High permeability

------
# 93

**SMILES:** C1CC1(C2=CC=C(C=C2)NC(=O)C3=CC(=NC=C3)C4=NC=CC(=C4)C(=O)O)N

**Label:** 0

**Predi:** 0

**Correct:** 1

# Response:
The given molecule is designed to act as an antagonist to the prostaglandin E2 (PGE2) receptor subtype EP4, which is involved in various cellular processes such as cell proliferation, survival, and angiogenesis. The molecule's structure is crucial for its function and permeability.

The molecule contains a pyridine ring, which is a common motif in many pharmaceutical compounds due to its ability to participate in hydrogen bonding and π-π interactions. This pyridine ring is likely to enhance the molecule's ability to interact with the EP4 receptor, contributing to its antagonist activity.

Additionally, the molecule features an amino group attached to a cyclopropyl ring. The cyclopropyl group is a small, rigid structure that can influence the molecule's overall conformation and lipophilicity. The presence of the amino group can increase the molecule's polarity, potentially affecting its solubility and permeability.

The molecule also includes a carboxylic acid group, which is known for its ability to form hydrogen bonds and ionic interactions. This functional group can enhance the molecule's solubility in aqueous environments, which is important for its bioavailability.

In the context of the Parallel Artificial Membrane Permeability Assay (PAMPA), the molecule's permeability is influenced by its overall balance of hydrophilic and lipophilic properties. The presence of polar groups such as the amino and carboxylic acid groups suggests that the molecule may have moderate permeability, as these groups can enhance solubility but may also limit passive diffusion through lipid membranes. However, the pyridine and cyclopropyl groups contribute to a degree of lipophilicity, which may facilitate membrane permeation.

Overall, the given molecule is likely to exhibit low-to-moderate permeability in the PAMPA assay, balancing its hydrophilic and lipophilic characteristics to achieve effective interaction with the EP4 receptor.

Final answer: Low-to-moderate permeability.

------
# 94

**SMILES:** C1CC(CCC1CC(=O)O)C2=CC=C(C=C2)N3CCOC4=NC=NC(=C4C3=O)N

**Label:** 0

**Predi:** 0

**Correct:** 1

# Response:
The given molecule is a complex organic compound with several functional groups and structural features that influence its permeability in the PAMPA assay. Let's break down these features and their implications:

1. **Aminopyrano[2,3-d]pyrimidine Core**: This part of the molecule contains a pyrano-pyrimidine system, which is a bicyclic structure. The presence of nitrogen atoms in the pyrimidine ring can contribute to hydrogen bonding and polar interactions, which may enhance the molecule's solubility in aqueous environments. However, the overall rigidity and planarity of this bicyclic system can also affect the molecule's ability to permeate through the membrane, potentially limiting its permeability.

2. **Cyclohexyl Group**: The cyclohexyl moiety is a non-polar, hydrophobic ring that can increase the lipophilicity of the molecule. This hydrophobic character can enhance the molecule's ability to interact with the lipid components of the artificial membrane, potentially increasing its permeability. However, the cyclohexyl group's bulkiness might hinder the molecule's passage through the membrane if it causes steric hindrance.

3. **Phenylacetic Acid Moiety**: The phenylacetic acid group introduces both aromatic and carboxylic acid functionalities. The aromatic ring can participate in π-π interactions with the membrane, while the carboxylic acid group can form hydrogen bonds and ion-dipole interactions. The acidic nature of the carboxylic acid can also influence the molecule's ionization state, which is crucial for permeability. Typically, the ionized form is more polar and may have reduced permeability, while the non-ionized form is more lipophilic and may have higher permeability.

4. **Overall Structure**: The combination of polar and non-polar regions in the given molecule suggests that it may have moderate permeability. The polar regions, such as the aminopyrano-pyrimidine core and the carboxylic acid group, can interact with the aqueous environment and polar sites on the membrane, while the cyclohexyl and phenyl groups can interact with the lipid components. This balance of interactions can result in a moderate permeability profile.

In summary, the given molecule's permeability in the PAMPA assay is likely to be moderate due to the interplay between its polar and non-polar regions, as well as the structural features that influence its solubility and interaction with the artificial membrane.

Final answer: Low-to-moderate permeability.

------
# 95

**SMILES:** CC[C@@H](C1=CC=CC=C1)NC(=O)C2=C(C(=NC3=CC=CC=C32)C4=CC=CC=C4)O

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a quinoline derivative with a carboxamide functional group. The quinoline core is a bicyclic structure consisting of a benzene ring fused to a pyridine ring, which is known for its planar aromatic nature. This structural feature can facilitate interactions with the artificial membrane, potentially enhancing permeability.

The presence of a hydroxy group on the quinoline ring introduces a polar functional group, which can form hydrogen bonds with the membrane. This interaction can increase the molecule's affinity for the membrane, potentially improving its permeability.

The carboxamide group is another polar moiety that can engage in hydrogen bonding, further contributing to the molecule's interaction with the membrane. This group is also capable of forming dipole-dipole interactions, which can stabilize the molecule's orientation within the membrane.

The phenyl groups attached to the nitrogen of the carboxamide and the quinoline ring provide hydrophobic characteristics. These aromatic rings can participate in π-π stacking interactions with the membrane, which can enhance the molecule's permeability by stabilizing its position within the membrane.

Overall, the combination of polar and non-polar interactions, along with the planar aromatic structure, suggests that the given molecule likely exhibits high permeability in the artificial membrane used in the PAMPA assay.

Final answer: High permeability.

------
# 96

**SMILES:** COC(=O)CNC(=O)C1=NC(=C2N1C=CN=C2)C3=CC=C(C=C3)[S+](=O)(C)[O-]

**Label:** 0

**Predi:** 0

**Correct:** 1

# Response:
The given molecule is a complex organic compound that can be analyzed for its permeability in the PAMPA assay. This assay is often used to predict the permeability of a molecule across biological membranes, which is crucial for drug development as it affects the bioavailability of the compound.

The structure of the given molecule includes several key features that influence its permeability:

1. **Imidazo[1,2-a]pyridine Core**: This bicyclic structure is known for its planar and aromatic characteristics, which can enhance the molecule's ability to interact with lipid membranes. The presence of nitrogen atoms in the ring can also contribute to hydrogen bonding, potentially affecting the molecule's solubility and permeability.

2. **Methylsulfonylphenyl Group**: The methylsulfonyl group is a polar moiety that can increase the hydrophilicity of the molecule. This group can enhance the molecule's solubility in aqueous environments, which is important for its interaction with the artificial membrane in the PAMPA assay. The presence of the phenyl ring can also contribute to the molecule's overall lipophilicity, balancing its hydrophilic and lipophilic properties.

3. **Acetamidomethoxyacetyl Moiety**: This part of the molecule includes an amide linkage and an ether group. The amide group can participate in hydrogen bonding, which may influence the molecule's interaction with the membrane. The methoxy group can add to the molecule's overall polarity, potentially affecting its permeability.

Overall, the given molecule's structure suggests a balance between hydrophilic and lipophilic properties, which is typical for molecules that need to cross biological membranes. The presence of aromatic rings and polar functional groups indicates that the molecule may have moderate permeability in the PAMPA assay, allowing it to interact with both the artificial membrane and the aqueous environment.

Final answer: Low-to-moderate permeability.

------
# 97

**SMILES:** C[S+](=O)(C1=CC=C(C=C1)C2=C3C=CC=CN3C(=N2)C(=O)N4CCOCC4)[O-]

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several distinct structural components, each contributing to its permeability characteristics in the PAMPA assay.

1. **Imidazo[1,2-a]pyridine Core**: This bicyclic structure is known for its planar and aromatic nature, which can enhance the molecule's ability to interact with the artificial membrane. The aromaticity and rigidity of this core can facilitate stacking interactions with the membrane, potentially increasing permeability.

2. **Morpholine Ring**: The presence of a morpholine ring introduces a degree of polarity to the molecule. Morpholine is a heterocyclic amine with both ether and amine functionalities, which can form hydrogen bonds with the membrane. This can enhance the molecule's solubility in aqueous environments and potentially improve its permeability through the membrane.

3. **Methanone Linkage**: The methanone group acts as a linker between the imidazo[1,2-a]pyridine core and the morpholine ring. This carbonyl group can participate in dipole-dipole interactions with the membrane, which may contribute to the molecule's overall permeability.

4. **Methylsulfonyl Group**: The methylsulfonyl group is a polar and electron-withdrawing moiety. It can increase the molecule's overall polarity, which may enhance solubility and permeability. Additionally, the presence of this group can influence the electronic distribution across the molecule, potentially affecting its interaction with the membrane.

Overall, the combination of aromatic and polar features in the given molecule suggests that it may exhibit high permeability in the PAMPA assay. The balance of hydrophobic and hydrophilic interactions, along with the structural rigidity provided by the imidazo[1,2-a]pyridine core, likely facilitates its passage through the artificial membrane.

Final answer: High permeability

------
# 98

**SMILES:** CCN(CCCOC1=CC2=C(C=C1)C(=NC=N2)NC3=NNC(=C3)CC(=O)NC4=CC(=CC=C4)F)CCOP(=O)(O)O

**Label:** 0

**Predi:** 0

**Correct:** 1

# Response:
The given molecule is a complex organic compound with several functional groups and structural features that influence its permeability in the PAMPA assay. Let's break down these features and their implications:

1. **Fluorophenyl Group**: The presence of a fluorophenyl group contributes to the molecule's lipophilicity, which can enhance its ability to permeate lipid membranes. Fluorine atoms can also increase the metabolic stability of the molecule, potentially prolonging its activity in biological systems.

2. **Pyrazolopyrimidine Core**: This bicyclic structure is a common motif in many pharmaceuticals, often associated with bioactivity. The rigidity and planarity of the pyrazolopyrimidine core can facilitate interactions with biological targets, but its size and shape may also affect membrane permeability. The core can contribute to the molecule's ability to fit into the membrane's lipid bilayer, potentially enhancing permeability.

3. **Aminoethyl Linkage**: The amino group in this linkage can form hydrogen bonds with the artificial membrane, potentially increasing the molecule's interaction with the membrane and enhancing permeability. However, the presence of the amino group also introduces a polar character, which can affect the overall balance between hydrophilicity and lipophilicity.

4. **Methoxypropoxy Chain**: This flexible ether linkage can increase the molecule's solubility in organic solvents, which is beneficial for permeability. The chain's length and flexibility allow the molecule to adapt its conformation to fit into the membrane, potentially facilitating passage.

5. **Phosphate Group**: The dihydrogen phosphate group is highly polar and hydrophilic, which can enhance the molecule's solubility in aqueous environments. However, this group may also hinder membrane permeability due to its inability to cross lipid bilayers easily. It can also contribute to the molecule's overall charge, affecting its interaction with the membrane.

Overall, the given molecule has a balance of lipophilic and hydrophilic features, with the fluorophenyl group and pyrazolopyrimidine core contributing to lipophilicity, while the aminoethyl linkage and phosphate group introduce polar characteristics. These features suggest that the molecule may have moderate permeability in the PAMPA assay, as it has both the ability to interact with the membrane and the potential to be hindered by its polar groups.

Final answer: Low-to-moderate permeability.

------
# 99

**SMILES:** C1COCCN1C2=CC(=O)C3=C(O2)C(=CC=C3)C4=CC=C(C=C4)N

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a member of the chromones, which are known for their planar aromatic structure. This particular molecule features a chromone core, which is a bicyclic structure consisting of a benzene ring fused to a pyranone ring. The presence of this core contributes to the molecule's planarity and aromaticity, which are important factors in determining its permeability.

The molecule also contains an aminophenyl group attached to the chromone core. The amino group is a polar functional group that can form hydrogen bonds, which may enhance the molecule's solubility in aqueous environments. However, the presence of this group can also introduce steric hindrance and affect the molecule's ability to interact with the artificial membrane.

Additionally, the molecule includes a morpholine ring, which is a heterocyclic amine. The morpholine ring is known for its basicity and ability to engage in hydrogen bonding. This can further influence the molecule's solubility and permeability by affecting its interaction with the membrane.

Overall, the combination of the chromone core, aminophenyl group, and morpholine ring suggests that the given molecule may exhibit moderate permeability in the PAMPA assay. The aromatic and planar nature of the chromone core can facilitate passage through the membrane, while the polar functional groups may enhance solubility and interaction with the membrane, potentially leading to a balance between permeability and retention.

Final answer: Low-to-moderate permeability.

------
# 100

**SMILES:** COC1=CC=CC(=C1)N2C(=CC(=N2)C(=O)O)C3=CC(=C(C=C3)C4CCCCC4)Cl

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound with several functional groups and aromatic rings, which influence its permeability in the PAMPA assay. 

The core structure of the given molecule is a pyrazole ring, which is a five-membered heterocyclic compound containing two nitrogen atoms. Pyrazole rings are known for their stability and ability to participate in hydrogen bonding, which can affect the molecule's interaction with the artificial membrane.

Attached to the pyrazole ring is a carboxylic acid group. Carboxylic acids are polar and can form hydrogen bonds, which typically enhance the molecule's solubility in water and its ability to interact with polar environments, such as the artificial membrane in PAMPA. This functional group can also contribute to the molecule's acidity, which may influence its ionization state at physiological pH, affecting permeability.

The molecule also contains a methoxyphenyl group. The methoxy group is an electron-donating group, which can increase the electron density of the aromatic ring, potentially affecting the molecule's overall polarity and its ability to interact with the membrane. The presence of the aromatic ring itself can contribute to hydrophobic interactions with the membrane.

Additionally, there is a phenyl group substituted with a cyclohexyl group. The cyclohexyl group is a non-polar, hydrophobic moiety that can enhance the lipophilicity of the molecule. This increased lipophilicity can improve the molecule's ability to permeate through lipid membranes, such as the artificial membrane used in PAMPA.

Overall, the combination of polar and non-polar groups, along with the aromatic rings, suggests that the given molecule may have moderate to high permeability in the PAMPA assay. The balance of hydrophilic and hydrophobic properties allows it to interact effectively with both the aqueous and lipid components of the membrane, facilitating its passage through the artificial barrier.

Final answer: High permeability

------
# 101

**SMILES:** CCN(C1CCC(CC1)N(C)CCOC)C2=CC(=CC(=C2C)C(=O)NCC3=C(C=C(NC3=O)C)C)C#CCN4CCOCC4

**Label:** 0

**Predi:** 1

**Correct:** 0

# Response:
The given molecule is a complex organic compound with several functional groups and structural features that influence its permeability in the PAMPA assay. Let's break down these features and their potential impact on permeability:

1. **Aromatic Amide Group**: The presence of an aromatic amide group in the molecule suggests that it has a planar structure, which can facilitate interactions with the artificial membrane. Aromatic amides are known for their ability to participate in π-π stacking interactions, which can enhance binding to the membrane.

2. **Cyclohexyl Group**: The cyclohexyl group is a non-polar, hydrophobic moiety that can increase the lipophilicity of the molecule. This hydrophobic character can enhance the molecule's ability to permeate lipid membranes, such as the artificial membrane used in PAMPA.

3. **Ethoxy and Morpholine Groups**: The ethoxy group and morpholine ring introduce polar characteristics to the molecule. These groups can form hydrogen bonds with the membrane, potentially aiding in permeation. The morpholine ring, in particular, is a common motif in drug design for improving solubility and membrane permeability.

4. **Pyridine and Piperidine Rings**: The pyridine and piperidine rings contribute to the molecule's overall polarity and can engage in hydrogen bonding and dipole interactions with the membrane. These rings can also enhance the molecule's ability to traverse biological membranes due to their aromatic nature.

5. **Ethyl and Methyl Substituents**: The ethyl and methyl groups are small, non-polar substituents that can increase the lipophilicity of the molecule. This can further enhance membrane permeability by increasing the molecule's ability to dissolve in the lipid bilayer of the membrane.

6. **Enone Group**: The enone group (a conjugated ketone) can participate in additional π-π interactions and may also be involved in Michael addition reactions, which could influence the molecule's reactivity and interaction with the membrane.

Overall, the given molecule exhibits a balance of hydrophobic and hydrophilic properties, with several functional groups that can interact with the artificial membrane. These features suggest that the molecule would have high permeability in the PAMPA assay, as it is likely to effectively interact with and traverse the membrane.

Final answer: High permeability

------
# 102

**SMILES:** CN1C=NC(=C1C2=CC=C(C=C2)OC)C3=NC=CC(=C3)C(=O)O

**Label:** 0

**Predi:** 1

**Correct:** 0

# Response:
The given molecule is a complex organic compound that features several functional groups and aromatic rings, which play a crucial role in its permeability characteristics.

The molecule contains a pyridine ring, which is a nitrogen-containing heterocycle. Pyridine rings are known for their ability to participate in hydrogen bonding and π-π interactions, which can enhance the molecule's ability to interact with the artificial membrane. This interaction can facilitate the passage of the molecule through the membrane, contributing to its permeability.

Additionally, the molecule has a methoxyphenyl group attached to an imidazole ring. The methoxy group is an electron-donating group, which can increase the lipophilicity of the molecule. Increased lipophilicity often enhances the ability of a molecule to permeate lipid membranes, such as the artificial membrane used in the PAMPA assay.

The imidazole ring itself is another nitrogen-containing heterocycle, which can also participate in hydrogen bonding and π-π interactions. This can further enhance the molecule's interaction with the membrane and its permeability.

The presence of a carboxylic acid group in the molecule introduces a polar and potentially ionizable functional group. Carboxylic acids can form hydrogen bonds and may also ionize under physiological conditions, which can affect the molecule's solubility and permeability. However, the carboxylic acid group can also introduce some degree of polarity, which might limit the overall permeability of the molecule through the membrane.

Overall, the combination of aromatic rings, heterocycles, and functional groups in the given molecule suggests that it may have moderate to high permeability in the PAMPA assay, as these features can facilitate interactions with the artificial membrane and enhance its ability to permeate through it.

Final answer: High permeability

------
# 103

**SMILES:** CC1=C(C=CC(=C1)Cl)COC2=CC=NN2C3=NC=CC(=C3)C(=O)O

**Label:** 0

**Predi:** 1

**Correct:** 0

# Response:
The given molecule is a complex organic compound that features several functional groups and structural elements that influence its permeability in the PAMPA assay. Let's break down these features and their impact on permeability:

1. **Pyrazole Ring**: The presence of a pyrazole ring, a five-membered heterocyclic compound containing two nitrogen atoms, contributes to the molecule's overall stability and rigidity. Pyrazole rings are known for their ability to participate in hydrogen bonding and π-π interactions, which can enhance the molecule's ability to interact with the artificial membrane. This interaction can facilitate permeation through the membrane, suggesting a potential for high permeability.

2. **Carboxylic Acid Group**: The carboxylic acid group is a polar functional group that can form hydrogen bonds with the artificial membrane. This group is often involved in ionic interactions, which can enhance the molecule's solubility in aqueous environments and improve its permeability. However, the presence of this group can also introduce some degree of polarity, which might be balanced by other hydrophobic parts of the molecule.

3. **Methoxy Linkage**: The methoxy group acts as a linker between the pyrazole ring and the phenyl ring. This ether linkage can contribute to the molecule's flexibility, allowing it to adapt its conformation to fit through the membrane. The methoxy group can also influence the molecule's lipophilicity, potentially enhancing its ability to permeate the membrane.

4. **Chlorinated Phenyl Ring**: The chlorinated phenyl ring introduces a degree of hydrophobicity to the molecule. The chlorine atom can increase the molecule's lipophilicity, which is often associated with better permeability through lipid membranes. However, the presence of the chlorine atom can also affect the molecule's overall polarity and solubility, which needs to be balanced with the other functional groups.

5. **Methyl Group**: The methyl group on the phenyl ring contributes to the hydrophobic character of the molecule. This group can enhance the molecule's ability to interact with the lipid components of the artificial membrane, potentially increasing its permeability.

Overall, the given molecule contains a combination of polar and non-polar functional groups, which suggests a balance between hydrophilicity and lipophilicity. The pyrazole ring, carboxylic acid group, and methoxy linkage contribute to the molecule's ability to interact with the artificial membrane, while the chlorinated phenyl ring and methyl group enhance its lipophilicity. These structural features collectively suggest that the given molecule likely exhibits high permeability in the PAMPA assay.

Final answer: High permeability

------
# 104

**SMILES:** C1CC(=O)NC1CNC(=O)C2=C3C=CNC3=CC(=N2)C4=CC=CC=C4

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound with several structural features that influence its permeability in the PAMPA assay. Let's break down these features and their implications:

1. **Indole Core**: The presence of an indole moiety, which is a bicyclic structure consisting of a benzene ring fused to a pyrrole ring, is significant. Indole derivatives are known for their ability to interact with biological membranes due to their planar structure and aromaticity. This can enhance the molecule's ability to permeate through the artificial membrane, contributing to high permeability.

2. **Phenyl Group**: The phenyl group attached to the indole core adds to the hydrophobic character of the molecule. Aromatic rings like phenyl groups can engage in π-π interactions with the membrane, potentially increasing the molecule's permeability.

3. **Pyrrolidinone Moiety**: The pyrrolidinone ring, which is a five-membered lactam, introduces a degree of polarity to the molecule. This can affect the overall solubility and permeability balance. The presence of a carbonyl group in the pyrrolidinone can form hydrogen bonds, which might influence the molecule's interaction with the membrane and its permeability.

4. **Carboxamide Group**: The carboxamide functional group is polar and can form hydrogen bonds, which may enhance the molecule's solubility in aqueous environments. However, it can also affect the permeability by introducing steric hindrance and increasing the molecule's overall polarity.

Overall, the given molecule has a combination of hydrophobic and polar features. The indole and phenyl groups contribute to hydrophobic interactions, while the pyrrolidinone and carboxamide groups introduce polar characteristics. These features suggest that the molecule would have a balance of permeability, potentially leading to high permeability in the PAMPA assay. However, the exact permeability would depend on the specific conditions of the assay and the nature of the artificial membrane used.

Final answer: High permeability.

------
# 105

**SMILES:** COCCNC(=O)C1=CC=C(C=C1)C2=NC=C3N2C=C(N=C3)C4=CC(=CC=C4)F

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a complex organic compound with several functional groups and aromatic rings that influence its permeability in the PAMPA assay. Let's break down the structural features and their impact on permeability:

1. **Aromatic Rings**: The molecule contains multiple aromatic rings, including a phenyl group and an imidazo[1,2-a]pyridine moiety. Aromatic rings generally contribute to lipophilicity, which can enhance the molecule's ability to permeate lipid membranes. However, the presence of these rings also suggests potential interactions with the artificial membrane, which is designed to mimic biological membranes.

2. **Fluorophenyl Group**: The fluorine atom on the phenyl ring can increase the molecule's lipophilicity and metabolic stability. Fluorine's electronegativity can also influence the electronic distribution within the molecule, potentially affecting its interaction with the membrane.

3. **Imidazo[1,2-a]pyridine Moiety**: This bicyclic structure is a key feature of the molecule. The nitrogen atoms in the imidazo[1,2-a]pyridine can participate in hydrogen bonding and other polar interactions, which may affect the molecule's overall polarity and solubility. This moiety can also contribute to the rigidity of the molecule, potentially impacting its ability to fit into the membrane's structure.

4. **Amide Linkage**: The benzamide group introduces an amide linkage, which is polar and can form hydrogen bonds. This functional group can enhance the molecule's solubility in aqueous environments and may also interact with the membrane through hydrogen bonding.

5. **Methoxyethyl Group**: The presence of a methoxyethyl group adds to the molecule's polarity and can increase its solubility in water. This group can also influence the molecule's overall conformation and flexibility, which may affect its permeability.

Overall, the given molecule's combination of aromatic rings, polar functional groups, and heterocyclic structures suggests that it may have moderate permeability in the PAMPA assay. The balance of lipophilic and polar characteristics allows it to interact with the artificial membrane, but the specific interactions will depend on the exact nature of the membrane and the assay conditions.

Final answer: Low-to-moderate permeability.

------
# 106

**SMILES:** CN1CCC(CC1)NC(=O)C2=NC3=C(N2C)C=C(C(=N3)C4=CC=CC=C4)C5=CC(=NC=C5)OC

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a complex organic compound with several functional groups and structural features that influence its permeability in the PAMPA assay. Let's break down these features and their potential impact on permeability:

1. **Aromatic Rings**: The molecule contains multiple aromatic rings, including a phenyl group and a pyridine ring. Aromatic rings can enhance lipophilicity, which often increases membrane permeability. However, the presence of these rings can also lead to steric hindrance, potentially limiting permeability.

2. **Methoxy Group**: The methoxy group attached to the pyridine ring can increase the molecule's lipophilicity, which may enhance permeability. However, it can also introduce some degree of polarity, which might balance the overall permeability.

3. **Carboxamide Group**: The carboxamide group is polar and can form hydrogen bonds, which may facilitate interactions with the artificial membrane. This group can also increase the molecule's solubility in aqueous environments, potentially affecting permeability.

4. **Piperazine Ring**: The piperazine ring, particularly with a methyl substitution, contributes to the molecule's basicity and can enhance solubility in water. This can improve permeability by allowing the molecule to interact favorably with the membrane.

5. **Overall Structure**: The combination of aromatic rings, methoxy group, carboxamide, and piperazine ring suggests that the given molecule has a balance of hydrophobic and hydrophilic properties. This balance can lead to moderate permeability, as the molecule can interact with both the lipid and aqueous phases of the artificial membrane.

Based on these structural features, the given molecule is likely to exhibit low-to-moderate permeability in the PAMPA assay. The presence of both lipophilic and hydrophilic groups suggests that it can partially penetrate the membrane, but the specific balance of these properties will determine the exact permeability profile.

Final answer: Low-to-moderate permeability.

------
# 107

**SMILES:** CC1=NC=CC(=C1)C2=CC3=C(N=C2C4=CC=CC=C4)N=C(N3C)C(=O)NCCN(C)C

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound with several functional groups and structural features that influence its permeability in the PAMPA assay. Let's break down these features and their implications:

1. **Imidazo[1,2-a]pyridine Core**: This bicyclic structure is a fused ring system that contributes to the molecule's rigidity and planarity. Such structures often enhance the ability of a molecule to interact with biological membranes, as they can fit into lipid bilayers more effectively. This core is likely to contribute to the molecule's permeability.

2. **Pyridine Ring**: The presence of a pyridine ring, which is a nitrogen-containing heterocycle, can enhance the molecule's ability to participate in hydrogen bonding and ionic interactions with the membrane. This can increase the molecule's affinity for the membrane, potentially enhancing its permeability.

3. **Phenyl Group**: The phenyl group attached to the imidazo[1,2-a]pyridine core adds hydrophobic character to the molecule. This can facilitate the passage of the molecule through the lipid bilayer of the artificial membrane, as hydrophobic interactions are a key driving force for membrane permeability.

4. **Dimethylaminoethyl Side Chain**: This functional group introduces a basic nitrogen atom, which can be protonated under physiological conditions. This can enhance the molecule's solubility in aqueous environments and may also facilitate interactions with the membrane through ionic or hydrogen bonding.

5. **Carboxamide Group**: The carboxamide group is polar and can form hydrogen bonds with the membrane or surrounding environment. This group can also contribute to the molecule's overall solubility and may influence its permeability by interacting with polar sites on the membrane.

Overall, the given molecule has a combination of hydrophobic and hydrophilic features, as well as rigid and flexible elements, which suggest that it can effectively interact with the artificial membrane. The presence of aromatic rings and heteroatoms allows for multiple types of interactions with the membrane, enhancing its permeability. Therefore, the given molecule is likely to exhibit high permeability in the PAMPA assay.

Final answer: High permeability

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# 108

**SMILES:** CN1CCCC1CCOC(C2=CC=CC=C2Cl)C3=CC4=NC=CC(=C4N3)C(=O)O

**Label:** 0

**Predi:** 1

**Correct:** 0

# Response:
The given molecule is a complex organic compound with several functional groups and structural features that influence its permeability in the PAMPA assay. Let's break down these features and their impact on permeability:

1. **Pyrrolopyridine Core**: The presence of a pyrrolopyridine core is significant as it provides a planar, aromatic structure. Aromatic systems are generally more lipophilic, which can enhance the molecule's ability to traverse lipid membranes. This core structure is likely to contribute to the molecule's permeability by facilitating interactions with the hydrophobic regions of the artificial membrane.

2. **Carboxylic Acid Group**: The carboxylic acid group is a polar functional group that can form hydrogen bonds with the artificial membrane. While this group can increase water solubility, it can also participate in ionic interactions with the membrane, potentially enhancing permeability. However, the presence of this group might also introduce some degree of polarity, which could limit permeability depending on the balance with other hydrophobic parts of the molecule.

3. **Chlorophenyl Group**: The chlorophenyl moiety adds to the lipophilicity of the molecule. The chlorine atom can enhance the electron-withdrawing properties of the phenyl ring, potentially affecting the molecule's overall electronic distribution and interaction with the membrane. This group can contribute to the molecule's ability to penetrate the membrane by increasing its hydrophobic character.

4. **Methoxyethyl Linker**: The methoxyethyl linker provides flexibility and a degree of polarity to the molecule. This linker can help in orienting the molecule in a way that optimizes interactions with the membrane, potentially enhancing permeability. The ether linkage can also contribute to the molecule's solubility and ability to form hydrogen bonds.

5. **Pyrrolidine Ring**: The pyrrolidine ring is a saturated, nitrogen-containing heterocycle that can enhance the molecule's solubility and ability to form hydrogen bonds. This ring can also contribute to the molecule's overall conformational flexibility, which might aid in permeation through the membrane.

Overall, the given molecule has a balance of hydrophobic and hydrophilic features, with a significant aromatic and lipophilic character due to the pyrrolopyridine core and chlorophenyl group. These features suggest that the molecule would have high permeability in the PAMPA assay, as it can effectively interact with the artificial membrane, leveraging its aromaticity and lipophilicity to traverse the membrane efficiently.

Final answer: High permeability.

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# 109

**SMILES:** CC1=NC2=C(N1)C=C(C=C2)C(=O)N3CCC4(CC3)CC5=C(C(=O)C4)N(N=C5)C(C)C

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a complex organic compound that features several distinct structural components, each contributing to its permeability characteristics in the PAMPA assay.

1. **Spiro Structure**: The presence of a spiro[5.5]undecane moiety indicates a bicyclic system where two rings are connected through a single shared atom. This spiro configuration can introduce rigidity and three-dimensionality to the molecule, potentially affecting its ability to interact with the artificial membrane. The rigidity can either enhance or hinder permeability depending on the orientation and fit of the molecule within the membrane.

2. **Pyrazole Ring**: The pyrazole ring is a five-membered heterocyclic compound containing two nitrogen atoms. This ring is known for its electron-rich nature, which can enhance the molecule's ability to form hydrogen bonds and engage in polar interactions with the membrane. The presence of a pyrazole ring can contribute to moderate permeability due to its balance of hydrophilic and hydrophobic properties.

3. **Carbonyl Group**: The carbonyl group (ketone) in the molecule is a polar functional group that can participate in hydrogen bonding. This can increase the molecule's solubility in polar environments, such as the aqueous phase of the PAMPA assay, and may facilitate interactions with the membrane, potentially leading to moderate permeability.

4. **Aromatic System**: The presence of an aromatic ring, specifically the isoquinoline moiety, contributes to the molecule's overall hydrophobic character. Aromatic systems can enhance membrane permeability due to their planar structure, which allows for favorable interactions with the lipid bilayer of the artificial membrane. However, the aromatic system's size and electronic properties can also limit permeability if they cause steric hindrance or unfavorable interactions.

5. **Substituents**: The propan-2-yl group attached to the pyrazole ring introduces additional hydrophobic character, which can influence the molecule's overall lipophilicity. This can enhance permeability by increasing the molecule's affinity for the lipid components of the membrane.

In summary, the given molecule's permeability in the PAMPA assay is likely moderate due to the interplay of its polar and non-polar functional groups, rigid spiro structure, and aromatic system. The balance of these features allows the molecule to interact favorably with the artificial membrane, but may not be sufficient to achieve high permeability.

Final answer: Low-to-moderate permeability.

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# 110

**SMILES:** C1C(C2=C(NC1=O)N=C(S2)N)C3=CC=CC=C3

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a thienopyridine derivative, which is characterized by a fused ring system consisting of a thiophene ring and a pyridine ring. This structure is known for its potential biological activity and is often used in pharmaceuticals.

The permeability of the given molecule in the PAMPA assay can be inferred from its structural features:

1. **Aromaticity and Planarity**: The presence of a phenyl group attached to the thienopyridine core contributes to the molecule's overall planarity and aromatic character. Aromatic compounds generally have higher lipophilicity, which can enhance their ability to permeate lipid membranes. This suggests that the given molecule may exhibit high permeability due to its aromatic nature.

2. **Functional Groups**: The amino group attached to the thienopyridine core introduces a polar character to the molecule. Amino groups can form hydrogen bonds, which may facilitate interactions with the artificial membrane. However, the presence of this group can also increase the molecule's hydrophilicity, potentially balancing its overall permeability.

3. **Saturated Ring System**: The dihydro component of the thienopyridine ring indicates partial saturation, which can affect the molecule's flexibility and ability to fit into the membrane. While saturation can reduce aromaticity, it may also enhance the molecule's ability to adapt to the membrane's structure, potentially increasing permeability.

Overall, the given molecule's aromatic and partially saturated thienopyridine core, combined with the presence of an amino group, suggests that it may have a balance of lipophilic and hydrophilic properties, leading to high permeability in the PAMPA assay.

Final answer: High permeability

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# 111

**SMILES:** C1CN(CC2=C1N=C(N2)C3=CC=C(C=C3)C(=O)N)C(=O)CN4CCOCC4

**Label:** 0

**Predi:** 1

**Correct:** 0

# Response:
The given molecule is a complex organic compound that includes several functional groups and structural features that influence its permeability in the PAMPA assay. Let's break down these features and their impact on permeability:

1. **Imidazo[1,2-a]pyridine Core**: This bicyclic structure is relatively planar and aromatic, which can enhance the molecule's ability to interact with the artificial membrane through π-π stacking interactions. Aromatic systems often have good membrane permeability due to their ability to traverse lipid bilayers.

2. **Morpholinyl Group**: The presence of a morpholine ring introduces a polar, heterocyclic amine into the structure. This group can form hydrogen bonds with the membrane, potentially increasing the molecule's solubility and permeability. The morpholine ring is often used to enhance the pharmacokinetic properties of compounds.

3. **Benzamide Moiety**: The benzamide group contributes to the molecule's overall polarity and ability to form hydrogen bonds. The amide linkage is a common feature in many bioactive molecules and can enhance binding interactions with the membrane.

4. **Hydrogen Bonding Potential**: The molecule contains several nitrogen and oxygen atoms that can participate in hydrogen bonding. This increases the molecule's solubility in aqueous environments and can facilitate interactions with the polar head groups of the artificial membrane.

5. **Lipophilicity**: While the molecule has polar groups, the overall structure is likely to have a moderate lipophilicity due to the aromatic rings and the presence of the imidazo[1,2-a]pyridine core. This balance of hydrophilic and lipophilic properties is often ideal for membrane permeability.

Considering these structural features, the given molecule is likely to exhibit high permeability in the PAMPA assay. The combination of aromaticity, hydrogen bonding potential, and balanced lipophilicity suggests that the molecule can effectively interact with and traverse the artificial membrane.

Final answer: High permeability

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# 112

**SMILES:** C1COCCN1CCNC(=O)C2CC(=O)N(C2)C3=NNC4=C3C=CC(=C4)Br

**Label:** 0

**Predi:** 1

**Correct:** 0

# Response:
The given molecule is a complex organic compound that can be analyzed for its permeability based on its structural features. The molecule contains several key functional groups and structural elements that influence its permeability.

1. **Indazole Ring System**: The presence of the indazole ring, which is a bicyclic structure consisting of a benzene ring fused to a pyrazole ring, contributes to the molecule's rigidity and planarity. This structural feature can enhance the molecule's ability to interact with the artificial membrane, potentially increasing its permeability.

2. **Bromo Substituent**: The bromine atom attached to the indazole ring introduces a degree of lipophilicity, which can affect the molecule's ability to traverse lipid membranes. The presence of a halogen like bromine can also influence the electronic properties of the molecule, potentially enhancing its interaction with the membrane.

3. **Pyrrolidine Ring**: The pyrrolidine ring is a five-membered nitrogen-containing heterocycle. This ring can impart flexibility to the molecule, allowing it to adapt its conformation when interacting with the membrane. The presence of a carbonyl group (oxo) adjacent to the pyrrolidine ring can also participate in hydrogen bonding, which may facilitate interaction with the membrane.

4. **Morpholine Ring**: The morpholine ring is a six-membered heterocycle containing both oxygen and nitrogen. This ring is polar and can enhance the molecule's solubility in aqueous environments, which is beneficial for permeability. The morpholine moiety can also participate in hydrogen bonding and ionic interactions, which may aid in membrane permeation.

5. **Carboxamide Group**: The carboxamide group is a polar functional group that can form hydrogen bonds with the membrane. This group can also contribute to the overall solubility of the molecule in biological environments, which is important for permeability.

Overall, the given molecule exhibits a combination of hydrophobic and hydrophilic properties due to its diverse functional groups. The indazole and bromo substituent contribute to lipophilicity, while the pyrrolidine, morpholine, and carboxamide groups enhance solubility and potential for hydrogen bonding. These features suggest that the molecule may have moderate to high permeability in the PAMPA assay, allowing it to effectively interact with the artificial membrane.

Final answer: High permeability

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# 113

**SMILES:** CC1=NC=C2CNCCC2=C1CNC(=O)CN3C=NC4=CC=CC=C4C3=O

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex structure that includes several key features influencing its permeability in the PAMPA assay. Let's break down these features and their implications:

1. **Quinazoline Core**: The presence of a quinazoline moiety, which is a bicyclic structure consisting of a benzene ring fused to a pyrimidine ring, contributes to the molecule's overall planarity and aromaticity. This aromatic system can enhance the molecule's ability to interact with the artificial membrane through π-π stacking interactions, potentially increasing its permeability.

2. **Tetrahydroquinoline Moiety**: The tetrahydroquinoline portion of the molecule introduces a partially saturated ring system, which can increase the flexibility of the molecule. This flexibility may allow the molecule to better adapt to the membrane's structure, potentially enhancing its permeability.

3. **Amide Linkage**: The presence of an amide group in the molecule provides a polar functional group that can form hydrogen bonds with the membrane. This interaction can stabilize the molecule's orientation within the membrane, facilitating its passage through the artificial barrier.

4. **Methyl Substitution**: The methyl group attached to the tetrahydroquinoline ring can influence the molecule's lipophilicity. While small, this group can enhance the molecule's hydrophobic character, which may aid in permeating the lipid-rich environment of the artificial membrane.

5. **Overall Structure**: The combination of aromatic and aliphatic components, along with polar functional groups, suggests that the given molecule has a balanced hydrophilic-lipophilic profile. This balance is often favorable for permeability in PAMPA assays, as it allows the molecule to interact with both the aqueous and lipid phases of the membrane.

Considering these structural features, the given molecule is likely to exhibit high permeability in the PAMPA assay, as it possesses a combination of aromaticity, flexibility, and a balanced hydrophilic-lipophilic profile that facilitates interaction with the artificial membrane.

Final answer: High permeability

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# 114

**SMILES:** C1CN(CC1NC(=O)C2=CC=CC=C2)C3=NNC(=C3)C4=CC=C(C=C4)Cl

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that includes several distinct structural features, each contributing to its permeability characteristics in the PAMPA assay.

1. **Pyrrole Ring**: The presence of a pyrrole ring, a five-membered aromatic heterocycle containing nitrogen, is significant. Pyrrole rings are known for their electron-rich nature, which can enhance interactions with the artificial membrane. This can lead to moderate to high permeability due to favorable interactions with the membrane's lipophilic environment.

2. **Chlorophenyl Group**: The chlorophenyl moiety introduces a lipophilic aromatic ring with a chlorine substituent. The chlorine atom can increase the molecule's lipophilicity, enhancing its ability to traverse the lipid-rich environment of the artificial membrane. This can contribute to higher permeability.

3. **Piperidine Ring**: The piperidine ring is a six-membered nitrogen-containing heterocycle. Piperidine rings are often flexible and can adopt various conformations, which may facilitate the molecule's interaction with the membrane. The presence of this ring can contribute to moderate permeability due to its balance of hydrophilic and lipophilic properties.

4. **Benzamide Group**: The benzamide moiety includes an amide linkage, which can form hydrogen bonds with the artificial membrane. This can enhance the molecule's interaction with the membrane, potentially increasing its permeability. However, the amide group can also introduce some degree of polarity, which might limit permeability compared to purely hydrophobic molecules.

Overall, the given molecule's structure suggests a balance of hydrophilic and lipophilic properties, with the pyrrole and chlorophenyl groups contributing to its lipophilicity and the piperidine and benzamide groups providing some degree of polarity. This balance typically results in moderate to high permeability in the PAMPA assay, allowing the molecule to effectively interact with the artificial membrane.

Final answer: High permeability.

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# 115

**SMILES:** CC1=NC=C(C=C1)C(=O)N2CCC3=C(C2)N=C4C=C(NN4C3=O)C5=CC=CC=C5

**Label:** 0

**Predi:** 1

**Correct:** 0

# Response:
The given molecule is a complex heterocyclic compound with several key structural features that influence its permeability in the PAMPA assay. 

Firstly, the presence of the pyridine ring, which is a nitrogen-containing aromatic ring, contributes to the molecule's ability to participate in hydrogen bonding and π-π interactions. This can enhance the molecule's solubility and interaction with the artificial membrane, potentially increasing its permeability.

Secondly, the tricyclic structure, which includes a pyrazolo[1,5-a]pyrimidine core, provides a rigid and planar framework. This rigidity can facilitate the molecule's passage through the membrane by allowing it to maintain a consistent orientation and conformation, which may enhance its permeability.

Additionally, the presence of a carbonyl group (the 6-oxo moiety) can increase the molecule's polarity, which may also contribute to its permeability by allowing it to form hydrogen bonds with the membrane or the surrounding environment.

The overall structure of the given molecule, with its combination of aromaticity, rigidity, and polar functional groups, suggests that it may have moderate to high permeability in the PAMPA assay. This is because these features can facilitate interactions with the artificial membrane, allowing the molecule to effectively permeate through it.

Final answer: High permeability.

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# 116

**SMILES:** C1CN(CCC2=C1C(=O)NC(=N2)N3CCOCC3)CC4=C(C=CC(=C4)Cl)F

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a complex structure that includes several functional groups and heterocyclic rings, which influence its permeability in the PAMPA assay. Let's break down the structural features and their impact on permeability:

1. **Pyrimidopyridazine Core**: The core structure of the given molecule is a pyrimidopyridazine, which is a bicyclic system combining pyrimidine and pyridazine rings. This core is relatively planar and aromatic, which can enhance the molecule's ability to interact with the artificial membrane through π-π stacking interactions. Aromatic systems often have good permeability due to their ability to traverse lipid membranes efficiently.

2. **Morpholine Ring**: The presence of a morpholine ring introduces a polar, heterocyclic amine into the structure. Morpholine is known for its solubility in water and can enhance the molecule's overall hydrophilicity. This can improve the molecule's permeability by increasing its solubility in the aqueous environment of the PAMPA assay.

3. **Substituted Phenyl Group**: The phenyl group is substituted with a chloro and a fluoro group. These halogen substituents can influence the molecule's lipophilicity and electronic properties. The chloro and fluoro groups can increase the lipophilicity of the molecule, which may enhance its ability to permeate the lipid-rich artificial membrane. However, they can also introduce steric hindrance, potentially reducing permeability.

4. **Methyl Linkage**: The methyl group connecting the morpholine to the pyrimidopyridazine core provides a degree of flexibility and spatial separation between the polar morpholine and the aromatic core. This can affect the molecule's ability to fit into the membrane pores, influencing its permeability.

Overall, the given molecule's structure suggests a balance between hydrophilic and lipophilic properties. The aromatic core and halogenated phenyl group contribute to lipophilicity, while the morpholine ring enhances hydrophilicity. This balance, along with the structural flexibility provided by the methyl linkage, likely results in moderate permeability in the PAMPA assay. Therefore, the final answer is:

Final answer: Low-to-moderate permeability.

------
# 117

**SMILES:** C1CN(CCC2=C1C(=O)NC(=N2)N3CCOCC3)CC4=C(C=C(C=C4)Cl)F

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex structure that includes several functional groups and heterocyclic rings, which influence its permeability in the PAMPA assay. Let's break down the structural components and their impact on permeability:

1. **Pyrimidopyrimidine Core**: The core structure of the given molecule is a pyrimidopyrimidine, which is a bicyclic system composed of two pyrimidine rings. Pyrimidine rings are aromatic and relatively planar, which can facilitate interactions with the artificial membrane. The aromatic nature of these rings can enhance the molecule's ability to pass through the membrane by allowing π-π stacking interactions with the membrane components.

2. **Diazepane Ring**: The presence of a diazepane ring, a seven-membered ring containing two nitrogen atoms, contributes to the molecule's flexibility and potential to adopt various conformations. This flexibility can aid in the molecule's ability to fit into the membrane's structure, potentially enhancing permeability.

3. **Substituted Phenyl Group**: The phenyl group is substituted with a chloro and a fluoro group. The chloro and fluoro substituents are electron-withdrawing, which can increase the lipophilicity of the molecule. This increased lipophilicity can enhance the molecule's ability to traverse the lipid-rich environment of the artificial membrane.

4. **Morpholine Ring**: The morpholine ring is a six-membered heterocycle containing both oxygen and nitrogen. This ring can increase the molecule's solubility in water, which is beneficial for permeability. The presence of the morpholine ring can also provide additional hydrogen bonding opportunities, which may facilitate interactions with the membrane.

Overall, the given molecule's combination of aromatic rings, heterocycles, and electron-withdrawing substituents suggests that it has a balance of hydrophilic and lipophilic properties. This balance is likely to enhance its permeability through the artificial membrane, indicating that the molecule would exhibit high permeability in the PAMPA assay.

Final answer: High permeability

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# 118

**SMILES:** COC1=CC=C(C=C1)C(=O)N2CCCC(C2)C3=NN(C(=O)N3)C4=CC=C(C=C4)OC

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several functional groups and structural motifs that influence its permeability in the PAMPA assay. Let's break down the key structural components and their impact on permeability:

1. **Triazole Ring**: The presence of a triazole ring is significant in the context of PAMPA. Triazole rings are known for their ability to participate in hydrogen bonding and π-π interactions, which can enhance the molecule's ability to interact with the artificial membrane. This can lead to moderate to high permeability, as the triazole ring can facilitate the passage of the molecule through the membrane.

2. **Piperidine Ring**: The piperidine moiety is a saturated nitrogen-containing heterocycle that can increase the molecule's lipophilicity. This can enhance the permeability of the molecule by increasing its ability to dissolve in the lipid bilayer of the artificial membrane. However, the piperidine ring itself is not highly polar, so it may not significantly hinder permeability.

3. **Methoxy Groups**: The methoxy groups attached to the phenyl rings contribute to the molecule's lipophilicity. These groups can enhance the overall hydrophobic character of the molecule, which can improve permeability by facilitating passage through the lipid-rich regions of the artificial membrane.

4. **Benzoyl Group**: The benzoyl group is a bulky aromatic moiety that can interact with the membrane through π-π stacking interactions. While it may contribute to some steric hindrance, the aromatic nature of the benzoyl group can also enhance permeability by interacting favorably with the membrane.

Overall, the given molecule's structure suggests that it has a balance of hydrophobic and hydrophilic interactions that can facilitate its passage through the artificial membrane. The triazole and piperidine rings, along with the methoxy and benzoyl groups, collectively contribute to a profile that supports moderate to high permeability in the PAMPA assay.

Final answer: High permeability

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# 119

**SMILES:** C1CN(CCC1C2=NN(C(=O)N2)C3=CC=C(C=C3)F)C(=O)C4=CC=CC=C4

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a member of the triazoles, which are known for their diverse biological activities and potential pharmaceutical applications. The structure of the given molecule includes several key features that influence its permeability:

1. **Triazole Ring**: The presence of the triazole ring is significant as it is a heterocyclic compound that can enhance the molecule's stability and bioavailability. Triazoles are often used in drug design due to their ability to form hydrogen bonds and interact with biological targets.

2. **Fluorophenyl Group**: The fluorophenyl moiety contributes to the molecule's lipophilicity, which can enhance its ability to permeate lipid membranes. The presence of the fluorine atom can also increase the metabolic stability of the molecule, as fluorine is highly electronegative and can influence the electronic distribution within the molecule.

3. **Benzoyl Group**: The benzoyl group is another lipophilic component that can facilitate membrane permeability. It can also participate in hydrophobic interactions with the lipid bilayer of the membrane, potentially enhancing the molecule's ability to cross the membrane.

4. **Piperidine Ring**: The piperidine ring is a saturated nitrogen-containing heterocycle that can improve the solubility and permeability of the molecule. Piperidine rings are often used in drug design to enhance the pharmacokinetic properties of compounds.

Overall, the combination of these structural features suggests that the given molecule is likely to have high permeability in the PAMPA assay. The lipophilic and hydrophilic balance provided by the fluorophenyl, benzoyl, and piperidine groups, along with the stability offered by the triazole ring, supports its ability to traverse the artificial membrane.

Final answer: High permeability

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# 120

**SMILES:** COC1=CC=C(C=C1)N2C(=O)NC(=N2)C3CCN(CC3)C(=O)C4CC4

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several distinct functional groups and structural motifs, which contribute to its permeability characteristics in the PAMPA assay.

1. **Cyclopropanecarbonyl Group**: The presence of the cyclopropanecarbonyl group introduces a small, strained ring structure that can influence the molecule's overall conformation and rigidity. This rigidity can affect the molecule's ability to interact with the artificial membrane, potentially enhancing its permeability due to reduced steric hindrance.

2. **Piperidine Ring**: The piperidine moiety is a six-membered nitrogen-containing heterocycle. Piperidine rings are known for their basicity and ability to form hydrogen bonds, which can facilitate interactions with the membrane. The presence of this ring can enhance the molecule's solubility and permeability, as it can interact with polar sites on the membrane.

3. **Triazol-3-one Moiety**: The triazole ring is a five-membered heterocycle containing three nitrogen atoms. This ring can participate in hydrogen bonding and π-π interactions, which may enhance the molecule's ability to permeate the membrane. The carbonyl group attached to the triazole can also contribute to hydrogen bonding, further influencing permeability.

4. **Methoxyphenyl Group**: The methoxy group attached to the phenyl ring increases the molecule's lipophilicity, which can enhance its ability to permeate lipid membranes. The aromatic nature of the phenyl ring can also facilitate π-π interactions with the membrane, potentially increasing permeability.

Overall, the combination of these structural features suggests that the given molecule is likely to exhibit high permeability in the PAMPA assay. The balance of hydrophilic and lipophilic properties, along with the ability to form various non-covalent interactions, supports its passage through the artificial membrane.

Final answer: High permeability

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# 121

**SMILES:** COC1=CC=C(C=C1)N2C(=O)NC(=N2)C3CCCN(C3)C(=O)C4=CC=CC=C4F

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several functional groups and structural motifs that influence its permeability in the PAMPA assay. Let's break down the key structural elements and their impact on permeability:

1. **Triazole Ring**: The presence of a triazole ring is significant in drug molecules due to its ability to participate in hydrogen bonding and π-π interactions. This heterocyclic ring can enhance the molecule's ability to interact with biological membranes, potentially increasing its permeability.

2. **Fluorophenyl Group**: The fluorine atom in the fluorophenyl group can increase the lipophilicity of the molecule, which often enhances membrane permeability. Fluorine's electronegativity can also influence the electronic distribution within the molecule, potentially affecting its interaction with the artificial membrane.

3. **Methoxyphenyl Group**: The methoxy group is an electron-donating group that can increase the lipophilicity of the molecule. This can enhance the molecule's ability to traverse lipid membranes, contributing to its permeability.

4. **Piperidine Ring**: The piperidine ring is a saturated nitrogen-containing heterocycle that can increase the molecule's solubility and flexibility. This can facilitate the molecule's interaction with the artificial membrane, potentially enhancing its permeability.

5. **Carbonyl Group**: The carbonyl group in the molecule can participate in hydrogen bonding, which may influence the molecule's interaction with the membrane. However, its presence can also introduce some polarity, which might reduce permeability to a certain extent.

Overall, the given molecule's combination of lipophilic groups (fluorophenyl and methoxyphenyl) and polar groups (carbonyl and triazole) suggests that it would exhibit moderate to high permeability in the PAMPA assay. The balance of these groups allows the molecule to interact favorably with the artificial membrane, facilitating its passage through the membrane.

Final answer: High permeability

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# 122

**SMILES:** CCCS(=O)(=O)C1=NC(=CC(=N1)NC2CC2)C3=CC4=C(C=C3)N(C=C4)C5CC(NC(C5)(C)C)(C)C

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound with several functional groups and structural features that influence its permeability in the PAMPA assay. Let's break down these features and their implications:

1. **Piperidine Rings**: The molecule contains two piperidine rings, one of which is substituted with an isopropyl group. Piperidine rings are typically non-polar and contribute to the lipophilicity of the molecule. The presence of these rings suggests that the molecule may have moderate to high lipophilicity, which can enhance its ability to permeate lipid membranes.

2. **Cyclohexyl Group**: The cyclohexyl group is a non-polar, hydrophobic moiety that can further increase the lipophilicity of the molecule. This group can enhance the molecule's ability to interact with the lipid components of the artificial membrane, potentially increasing its permeability.

3. **Sulfonyl Group**: The sulfonyl group is a polar functional group that can form hydrogen bonds and interact with polar sites on the artificial membrane. While it may introduce some degree of polarity, its presence is likely balanced by the overall lipophilic nature of the molecule due to the other groups.

4. **Indole Ring**: The indole ring is a planar, aromatic structure that can participate in π-π interactions with the artificial membrane. This can contribute to the molecule's ability to permeate the membrane, as aromatic interactions can stabilize the molecule's orientation and binding within the membrane.

5. **Amino Group**: The amino group is a basic functional group that can form hydrogen bonds and ionic interactions. This group can enhance the molecule's solubility in aqueous environments and may also interact with acidic sites on the artificial membrane, potentially aiding in permeation.

Overall, the given molecule's structure suggests that it has a balance of lipophilic and polar characteristics, which can facilitate its permeability through the artificial membrane. The presence of multiple non-polar groups, such as the piperidine and cyclohexyl rings, likely dominates, indicating that the molecule would exhibit high permeability in the PAMPA assay.

Final answer: High permeability

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# 123

**SMILES:** CC1=C(C(=NO1)C)C2=CC(=C(C=C2)C3=CC(=C(S3)NC(=O)N)C(=O)N)O[C@H]4CCNC4

**Label:** 0

**Predi:** 0

**Correct:** 1

# Response:
The given molecule is a complex organic compound with several functional groups and aromatic rings that contribute to its permeability characteristics. Let's break down the structural features and their impact on permeability:

1. **Aromatic Rings**: The molecule contains multiple aromatic rings, including a thiophene ring and two phenyl rings. Aromatic rings generally enhance lipophilicity, which can increase membrane permeability due to their ability to interact with lipid bilayers through π-π interactions and van der Waals forces.

2. **Substituents on Aromatic Rings**:
   - The presence of a methyl group on one of the phenyl rings increases the hydrophobic character of the molecule, potentially enhancing its ability to permeate lipid membranes.
   - The oxazole ring, which is a heterocyclic aromatic compound, contributes to the molecule's overall stability and may influence its electronic properties, potentially affecting its interaction with the artificial membrane.

3. **Functional Groups**:
   - The carbamoyl group is a polar functional group that can form hydrogen bonds with the artificial membrane. This can enhance the molecule's solubility in aqueous environments, which is important for its interaction with the membrane.
   - The carbamoyl group also contributes to the molecule's ability to form hydrogen bonds, which can stabilize interactions with the membrane and potentially facilitate permeation.

4. **Cyclopentyl Group**: The cyclopentyl group is a non-aromatic, hydrophobic moiety that can increase the overall lipophilicity of the molecule. This can enhance membrane permeability by allowing the molecule to embed within the lipid bilayer.

Overall, the given molecule's structure suggests that it has a balance of hydrophobic and hydrophilic properties, which is typical for molecules with moderate permeability in PAMPA assays. The aromatic rings and hydrophobic substituents likely contribute to its ability to interact with the lipid components of the artificial membrane, while the polar carbamoyl group enhances its solubility and potential for hydrogen bonding. Therefore, the given molecule is likely to exhibit moderate permeability in the PAMPA assay.

Final answer: Low-to-moderate permeability.

------
# 124

**SMILES:** CC(C)C1=CC(=NN1)C(=O)N2CC[C@H](C2)NC(=O)C3CC3

**Label:** 0

**Predi:** 1

**Correct:** 0

# Response:
The given molecule is a PAMPA permeability assay result, which indicates its ability to permeate through a synthetic membrane, mimicking biological membranes. The molecule is classified as a N-acylpyrrolidine, which suggests the presence of an acyl group attached to a pyrrolidine ring. This structural feature can influence the molecule's lipophilicity and, consequently, its permeability.

The presence of the cyclopropanecarbonyl group contributes to the molecule's rigidity and potential steric hindrance, which may affect its interaction with the membrane. Cyclopropane rings are known for their high strain energy, which can impact the molecule's overall conformation and permeability.

The pyrazole ring in the structure is a heterocyclic aromatic compound, which can enhance the molecule's ability to interact with biological targets through hydrogen bonding and π-π interactions. However, the pyrazole ring's aromaticity may also contribute to the molecule's overall hydrophobic character, potentially increasing its permeability.

The isopropyl group attached to the pyrazole ring further increases the molecule's hydrophobicity, which is generally associated with higher permeability through lipid membranes. This group can also enhance the molecule's ability to interact with hydrophobic regions of the membrane.

Overall, the combination of these structural features suggests that the given molecule likely exhibits high permeability in the PAMPA assay due to its hydrophobic character, rigidity, and potential for favorable interactions with the membrane.

Final answer: High permeability

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# 125

**SMILES:** C[C@H](C1=NN=C2N1C=C(C=C2F)C3=CN(N=C3)C)N4C=CC5=C(C4=O)C=C(C=N5)OCCOC

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is designed to act as a potent and selective inhibitor of the T790M mutant form of the epidermal growth factor receptor (EGFR). This mutant form is known to be resistant to other EGFR inhibitors, which is why the given molecule is under investigation for its antineoplastic activity, particularly in non-small cell lung cancer.

The structure of the given molecule includes several key features that contribute to its permeability and activity:

1. **Fluoropyrazinopyridazine Moiety**: The presence of a fluorine atom in the pyrazinopyridazine ring system can enhance the molecule's lipophilicity, which is often associated with improved membrane permeability. Fluorine can also influence the electronic properties of the molecule, potentially affecting its binding affinity to the target receptor.

2. **Methoxyethoxy Side Chain**: The methoxyethoxy group introduces a degree of polarity to the molecule, which can enhance solubility and potentially improve permeability through biological membranes. This side chain may also play a role in the molecule's pharmacokinetic properties, such as absorption and distribution.

3. **Pyrazolyl and Pyrimidinyl Groups**: These heterocyclic components are likely involved in specific interactions with the EGFR mutant. The pyrazolyl group, in particular, may contribute to the molecule's selectivity and binding affinity by forming hydrogen bonds or pi-stacking interactions with the target protein.

4. **Overall Molecular Architecture**: The combination of hydrophobic and hydrophilic elements in the given molecule suggests a balanced profile that could facilitate its passage through the lipid bilayer of cell membranes while maintaining sufficient solubility in the bloodstream.

In summary, the given molecule's structural features, including the fluoropyrazinopyridazine moiety, methoxyethoxy side chain, and heterocyclic groups, are likely to confer high permeability to the artificial membrane, allowing it to effectively reach and inhibit the T790M mutant EGFR. This is crucial for its potential therapeutic application in overcoming resistance to other EGFR inhibitors in non-small cell lung cancer.

Final answer: High permeability

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# 126

**SMILES:** CCN1C(=NC(=N1)C2CCN(CC2)C(=O)CCO)C3=CN=C(C(=N3)C4=NN=C(O4)C(C)(C)C)N

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a complex organic compound with several functional groups and heterocyclic rings that contribute to its permeability characteristics. Let's break down the structural features and their implications for permeability:

1. **Heterocyclic Rings**: The molecule contains multiple heterocyclic rings, including an oxazole, a pyrazole, and a pyrimidine. These rings are typically planar and can enhance the molecule's ability to interact with biological membranes through π-π stacking interactions. However, the presence of nitrogen atoms in these rings can also introduce hydrogen bonding capabilities, which may affect the molecule's solubility and permeability.

2. **Amino Group**: The presence of an amino group in the pyrazole ring can increase the molecule's hydrophilicity, potentially enhancing its solubility in aqueous environments. This group can also participate in hydrogen bonding, which may facilitate interactions with the artificial membrane.

3. **Piperidine Ring**: The piperidine moiety is a saturated six-membered ring containing a nitrogen atom. This structure is relatively flexible and can enhance the molecule's ability to fit into the membrane's lipid bilayer. The presence of the piperidine ring can also contribute to the overall basicity of the molecule, which may affect its ionization state and permeability.

4. **Hydroxypropanone Group**: The hydroxypropanone group introduces a hydroxyl group, which is polar and can form hydrogen bonds. This group can increase the molecule's solubility in water and may also interact with the membrane's polar head groups, potentially enhancing permeability.

5. **Tert-butyl Group**: The tert-butyl group is a bulky, hydrophobic moiety that can influence the molecule's overall lipophilicity. This group may enhance the molecule's ability to penetrate lipid membranes by increasing its hydrophobic interactions with the membrane's lipid bilayer.

Overall, the given molecule's structure suggests a balance between hydrophilic and hydrophobic properties, with multiple functional groups capable of interacting with the artificial membrane. The combination of heterocyclic rings, amino and hydroxyl groups, and a tert-butyl group likely contributes to a moderate permeability profile, allowing the molecule to traverse the membrane while maintaining some solubility in aqueous environments. Therefore, the given molecule is likely to exhibit low-to-moderate permeability in the Parallel Artificial Membrane Permeability Assay (PAMPA).

Final answer: Low-to-moderate permeability.

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# 127

**SMILES:** C1CCN(C1)C(=O)[C@@H]2CCCN(C2)C3=NC4=C(C=C3)NC(=N4)C5(CC5)N6C=C(C=N6)Cl

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex structure that includes several key features influencing its permeability in the PAMPA assay. Let's break down these features and their implications:

1. **Pyridine Ring with Chlorine Substitution**: The presence of a chlorinated pyridine ring suggests that the molecule has a degree of lipophilicity, which can enhance its ability to interact with lipid membranes. The chlorine atom can also contribute to the molecule's overall hydrophobic character, potentially increasing its permeability through the artificial membrane.

2. **Imidazo[1,2-a]pyridine Moiety**: This bicyclic structure is known for its planar and aromatic nature, which can facilitate interactions with the membrane through π-π stacking or van der Waals forces. The aromaticity can also contribute to the molecule's ability to traverse lipid bilayers.

3. **Piperidine Ring**: The piperidine ring is a saturated, aliphatic amine that can enhance the molecule's solubility in aqueous environments. This balance between hydrophilic and hydrophobic properties can be crucial for the molecule's permeability, as it may allow for sufficient interaction with the membrane while maintaining solubility.

4. **Azaspirodecane Core**: The spirocyclic structure introduces a unique three-dimensional shape, which can affect how the molecule fits into the membrane. The azaspirodecane core may provide a rigid framework that can enhance binding affinity to the membrane, potentially increasing permeability.

5. **Methanone Linkage**: The carbonyl group in the methanone linkage can participate in hydrogen bonding, which may influence the molecule's interaction with the membrane. This functional group can also affect the overall polarity of the molecule, impacting its permeability.

Overall, the given molecule's combination of aromatic rings, lipophilic substituents, and a balanced hydrophilic-lipophilic profile suggests that it would exhibit high permeability in the PAMPA assay. The structural features promote interactions with the artificial membrane, enhancing its ability to permeate through the lipid layers.

Final answer: High permeability

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# 128

**SMILES:** C[C@@]1(C2=C(C=C(C=C2)C3=CNN=C3)C(=O)N1)C4=NC=NC=C4F

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex structure that includes several functional groups and heterocyclic rings, which contribute to its permeability characteristics in the PAMPA assay.

1. **Indole Core**: The presence of an indole core is significant as it is a planar, aromatic structure that can facilitate interactions with the artificial membrane. Indole derivatives are known for their ability to permeate biological membranes due to their aromaticity and planar nature, which can enhance lipophilicity and membrane affinity.

2. **Fluoro Substitution**: The fluoro group attached to the indole ring can influence the molecule's electronic properties, potentially increasing its lipophilicity. Fluorine atoms can enhance membrane permeability by increasing the molecule's ability to interact with lipid bilayers, while also affecting the molecule's metabolic stability.

3. **Pyrazole Ring**: The pyrazole ring is a five-membered heterocycle that can contribute to the molecule's overall polarity and hydrogen bonding capabilities. The presence of a pyrazole ring can enhance the molecule's ability to form hydrogen bonds with the artificial membrane, potentially increasing its permeability.

4. **Pyrimidinyl Group**: The pyrimidinyl group is another heterocyclic component that can contribute to the molecule's overall polarity and ability to form hydrogen bonds. Pyrimidine rings are often involved in interactions with biological targets, and their presence can enhance the molecule's ability to permeate the membrane by increasing its solubility in lipid environments.

5. **Methyl Group**: The methyl group attached to the indole ring can increase the molecule's hydrophobic character, which may enhance its ability to permeate the lipid-rich environment of the artificial membrane.

Overall, the given molecule's combination of aromatic and heterocyclic structures, along with the presence of functional groups like fluoro and methyl, suggests that it has a high potential for permeability in the PAMPA assay. The balance of hydrophobic and polar characteristics allows it to interact favorably with the artificial membrane, indicating high permeability.

Final answer: High permeability

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# 129

**SMILES:** CC[C@@]1(C2=C(COC1=O)C(=O)N3CC4=C(C5=CC=CC=C5N=C4C3=C2)CCNC(C)C)O

**Label:** 0

**Predi:** 1

**Correct:** 0

# Response:
The given molecule is a pyranoindolizinoquinoline, which is a complex polycyclic compound. The structure of this molecule includes several key features that influence its permeability:

1. **Polycyclic Framework**: The molecule has a pentacyclic structure, which contributes to its rigidity and stability. This rigidity can affect the molecule's ability to fit into the membrane pores, potentially enhancing its permeability due to a more defined shape that can interact with the membrane.

2. **Hydroxy and Carbonyl Groups**: The presence of a hydroxy group and two carbonyl groups in the structure can form hydrogen bonds with the artificial membrane. These interactions can increase the molecule's affinity for the membrane, potentially enhancing its permeability.

3. **Ethyl and Isopropyl Groups**: The ethyl and isopropyl groups contribute to the hydrophobic character of the molecule. These groups can interact with the hydrophobic regions of the artificial membrane, which may facilitate the passage of the molecule through the membrane.

4. **Amino Group**: The presence of an amino group can introduce basicity to the molecule, which may affect its solubility and permeability. The amino group can also participate in ionic interactions with the membrane, potentially enhancing permeability.

Overall, the combination of these structural features suggests that the given molecule is likely to have high permeability in the artificial membrane due to its ability to form multiple interactions with the membrane, its rigid polycyclic structure, and its balance of hydrophobic and hydrophilic properties.

Final answer: High permeability

------
# 130

**SMILES:** COC1=CC=C(C=C1)C2=CC=C(O2)C(=O)NC3CC(C3)C4=CC(=O)NC(=N4)N

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several distinct structural components, each contributing to its permeability characteristics in the PAMPA assay.

1. **Furan Ring**: The presence of a furan ring, a five-membered aromatic heterocycle containing oxygen, is significant. Furan rings are known for their electron-rich nature, which can enhance the molecule's ability to interact with the artificial membrane. This interaction is often due to π-π stacking or hydrogen bonding with the membrane components, potentially increasing permeability.

2. **Methoxyphenyl Group**: The methoxyphenyl moiety introduces an aromatic ring with a methoxy substituent. The methoxy group is an electron-donating group, which can further enhance the aromatic ring's electron density. This can improve the molecule's ability to penetrate the membrane by facilitating interactions with the membrane's lipophilic environment.

3. **Cyclobutyl Group**: The cyclobutyl ring is a four-membered aliphatic ring that can impart rigidity to the molecule. This rigidity can influence the molecule's overall shape and size, potentially affecting its ability to fit through the membrane pores. However, in this case, the cyclobutyl group is likely to contribute to the molecule's overall hydrophobic character, which can enhance permeability through the lipid-rich regions of the artificial membrane.

4. **Pyrimidinone Moiety**: The pyrimidinone group is a heterocyclic aromatic ring with nitrogen atoms, which can participate in hydrogen bonding. This feature can enhance the molecule's solubility and interaction with the membrane, potentially increasing permeability.

5. **Amide Linkage**: The amide bond in the molecule is a polar functional group that can form hydrogen bonds with the membrane. This can increase the molecule's solubility in the membrane environment, facilitating its passage through the membrane.

Overall, the combination of aromatic rings, heteroatoms, and functional groups in the given molecule suggests that it has multiple sites for interaction with the artificial membrane. These interactions can enhance its permeability, making it likely to have high permeability in the PAMPA assay.

Final answer: High permeability

------
# 131

**SMILES:** C[C@]12C[C@H]([C@@H]([C@@]1(CC(=O)[C@@]3([C@H]2CC=C4[C@H]3C=C(C(=O)C4(C)C)O)C)C)[C@](C)(C(=O)/C=C\C(C)(C)O)O)O

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound with a multi-ring structure, specifically a cyclopenta[a]phenanthrene framework. This structure is characteristic of many steroid-like molecules, which often have significant biological activity. The molecule is further modified with several functional groups that influence its permeability.

1. **Hydroxyl Groups**: The presence of multiple hydroxyl groups (dihydroxy) in the molecule increases its hydrophilicity, which can enhance its solubility in aqueous environments. These groups can form hydrogen bonds with the artificial membrane, potentially increasing permeability by facilitating interactions with the membrane.

2. **Ketone Groups**: The molecule contains two ketone groups (dione), which are polar and can also participate in hydrogen bonding. These groups may interact with the membrane, influencing its permeability. The presence of ketones can also affect the molecule's overall polarity and solubility.

3. **Methyl Groups**: The presence of several methyl groups (pentamethyl) contributes to the hydrophobic character of the molecule. These groups can enhance the molecule's ability to interact with the lipid components of the artificial membrane, potentially increasing permeability by facilitating passage through the membrane.

4. **Double Bonds**: The molecule includes a double bond (en) in its side chain, which can affect its conformation and flexibility. This structural feature may influence how the molecule fits into the membrane, impacting its permeability.

5. **Stereochemistry**: The specific stereochemistry of the molecule, indicated by the multiple chiral centers, plays a crucial role in its interaction with the artificial membrane. The spatial arrangement of these chiral centers can affect the molecule's ability to fit into and traverse the membrane.

Overall, the given molecule's combination of hydrophilic and hydrophobic groups, along with its specific stereochemistry, suggests that it may have moderate to high permeability in the PAMPA assay. The balance of polar and non-polar interactions with the artificial membrane likely facilitates its passage, making it suitable for further biological evaluation.

Final answer: High permeability

------
# 132

**SMILES:** CCC[C@@H](C1=CC=CC=C1)NC(=O)C(=CC2=NC(=CC=C2)Br)C#N

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound with several functional groups and structural features that influence its permeability in the PAMPA assay. Let's break down these features and their impact on permeability:

1. **Amide Group**: The presence of the amide group (prop-2-enamide) is significant in PAMPA as it can form hydrogen bonds with the artificial membrane. This interaction can enhance the molecule's permeability by stabilizing its orientation and facilitating passage through the membrane.

2. **Bromophenyl Group**: The bromophenyl moiety introduces a halogen atom, bromine, which can increase the lipophilicity of the molecule. This increased lipophilicity can enhance the molecule's ability to traverse lipid membranes, contributing to higher permeability.

3. **Pyridinyl Group**: The pyridinyl group, being a heteroaromatic ring, can also contribute to the molecule's lipophilicity. However, the nitrogen atom in the pyridine ring can participate in hydrogen bonding, which may affect the molecule's interaction with the membrane and its overall permeability.

4. **Butan-2-yl Side Chain**: The butan-2-yl side chain is a hydrophobic alkyl group that can enhance the lipophilicity of the molecule. This feature can improve the molecule's ability to permeate through the lipid-rich environment of the artificial membrane.

5. **Conjugated System**: The presence of a conjugated system, as indicated by the prop-2-enamide, can influence the electronic properties of the molecule. This conjugation can affect the molecule's ability to interact with the membrane, potentially enhancing permeability by stabilizing the transition state during membrane passage.

Overall, the given molecule exhibits a combination of hydrophilic and hydrophobic characteristics, along with the ability to form hydrogen bonds and participate in electronic interactions. These features collectively suggest that the molecule has high permeability in the PAMPA assay, as it can effectively interact with and pass through the artificial membrane.

Final answer: High permeability

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# 133

**SMILES:** C1=CC=C(C=C1)C2=CN=C(N=C2NC3=CC(=C(C=C3)F)F)C4=CC=NC=C4

**Label:** 0

**Predi:** 1

**Correct:** 0

# Response:
The given molecule is a pyrimidine derivative with several functional groups that influence its permeability in the PAMPA assay. 

Firstly, the pyrimidine core is a heterocyclic aromatic compound, which generally contributes to the molecule's stability and planarity. This planarity can facilitate interactions with the artificial membrane, potentially enhancing permeability.

The presence of a phenyl group attached to the pyrimidine ring introduces additional hydrophobic character. This hydrophobicity can enhance the molecule's ability to traverse lipid membranes, as it may interact favorably with the hydrophobic regions of the artificial membrane.

Additionally, the molecule contains a pyridinyl group, which is another aromatic heterocycle. The nitrogen atom in the pyridinyl group can participate in hydrogen bonding, which may influence the molecule's solubility and permeability. The presence of this group can also contribute to the overall polarity of the molecule, potentially affecting its ability to permeate the membrane.

The difluorophenyl moiety introduces fluorine atoms, which can significantly impact the molecule's properties. Fluorine is highly electronegative, and its presence can increase the molecule's lipophilicity while also affecting its electronic properties. This can lead to enhanced membrane permeability by increasing the molecule's ability to interact with the lipid bilayer.

Overall, the combination of aromatic rings, hydrophobic phenyl groups, and the presence of nitrogen and fluorine atoms suggest that the given molecule likely exhibits high permeability in the PAMPA assay. The balance of hydrophobic and polar characteristics allows it to effectively interact with the artificial membrane, facilitating its passage.

Final answer: High permeability.

------
# 134

**SMILES:** CC(=O)N1CCC2=C(C1)SC3=C2C(=O)N(C(=O)N3CC4=CC(=CC=C4)C(F)(F)F)C5=CC=CC=C5

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound with several distinct structural features that influence its permeability in the PAMPA assay. Let's break down these features and their implications:

1. **Tricyclic Core Structure**: The molecule contains a tricyclic core, which is a fused ring system. Such structures often contribute to rigidity and can affect the molecule's ability to fit into biological membranes. The presence of multiple rings can enhance the molecule's stability and potentially increase its permeability by allowing it to interact more effectively with the membrane.

2. **Thia and Diaza Components**: The inclusion of sulfur (thia) and nitrogen (diaza) atoms in the tricyclic system introduces heteroatoms that can participate in hydrogen bonding and other polar interactions. These interactions can enhance the molecule's solubility and permeability by facilitating its passage through the membrane.

3. **Acetyl and Phenyl Groups**: The acetyl group is a small, polar moiety that can increase the molecule's solubility in aqueous environments, which is beneficial for permeability. The phenyl group, being a hydrophobic aromatic ring, can interact with the lipid components of the membrane, potentially aiding in permeation.

4. **Trifluoromethylphenyl Substituent**: The trifluoromethyl group is highly electronegative and can increase the lipophilicity of the molecule. This group can enhance the molecule's ability to penetrate lipid membranes by increasing its hydrophobic character, which is a desirable property for permeability.

5. **Overall Molecular Size and Complexity**: The large and complex structure of the given molecule, with multiple rings and functional groups, suggests that it may have a moderate to high permeability. The balance of hydrophilic and hydrophobic components, along with the rigidity provided by the tricyclic system, likely allows the molecule to navigate the artificial membrane effectively.

In summary, the given molecule's tricyclic core, heteroatoms, and functional groups collectively suggest that it would exhibit high permeability in the PAMPA assay. The combination of polar and non-polar features, along with the structural rigidity, supports its ability to interact with and permeate the artificial membrane.

Final answer: High permeability

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# 135

**SMILES:** C1=CC=C2C(=C1)C(=NC(=N2)C3=CC=NC=C3)NC4=CC(=C(C=C4)C5=C(C=C(C=C5)F)Cl)F

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a quinazoline derivative, which is a class of compounds known for their potential biological activity, including as kinase inhibitors. The molecule's structure includes several key features that influence its permeability:

1. **Aromatic Rings**: The molecule contains multiple aromatic rings, including a quinazoline core, a pyridine ring, and a phenyl ring. Aromatic rings can enhance lipophilicity, which often correlates with increased membrane permeability. However, the presence of these rings also suggests potential interactions with the artificial membrane, which is designed to mimic biological membranes.

2. **Halogen Substituents**: The presence of halogen atoms, specifically chlorine and fluorine, on the phenyl ring can significantly impact the molecule's electronic properties and lipophilicity. Halogens can increase the molecule's ability to penetrate lipid membranes by enhancing its hydrophobic character. The electron-withdrawing nature of these halogens can also influence the molecule's overall polarity and solubility.

3. **Amino Group**: The quinazoline-4-amine moiety introduces an amino group, which can form hydrogen bonds with the artificial membrane. This functional group can enhance the molecule's solubility in aqueous environments, potentially facilitating its interaction with the membrane.

4. **Overall Structure**: The combination of aromatic rings, halogen substituents, and an amino group suggests that the given molecule may have a balance of hydrophobic and hydrophilic properties. This balance is crucial for permeability, as it allows the molecule to interact with both the lipid and aqueous phases of the artificial membrane.

Considering these structural features, the given molecule is likely to exhibit moderate permeability in the artificial membrane. The aromatic and halogenated components contribute to its lipophilicity, while the amino group provides a degree of hydrophilicity, allowing for a balanced interaction with the membrane.

Final answer: Low-to-moderate permeability.

------
# 136

**SMILES:** C1CN(CCC1C#N)C2=NC(=CS2)C3=CC=C(C=C3)Br

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several distinct structural components, each contributing to its permeability characteristics in the PAMPA assay.

1. **Piperidine Ring**: The presence of a piperidine ring, which is a six-membered ring containing one nitrogen atom, is a common feature in many pharmaceuticals. Piperidine rings are known for their ability to enhance the solubility and permeability of molecules due to their basic nature and ability to form hydrogen bonds. This can facilitate the passage of the molecule through the artificial membrane.

2. **Thiazole Ring**: The thiazole ring is a five-membered heterocyclic compound containing both sulfur and nitrogen. This ring is relatively planar and can participate in π-π stacking interactions, which may aid in the molecule's ability to interact with the membrane. The presence of the thiazole ring can also contribute to the overall lipophilicity of the molecule, which is a key factor in membrane permeability.

3. **Bromophenyl Group**: The bromophenyl group introduces a halogen atom, bromine, which can enhance the lipophilicity of the molecule. Halogen atoms are known to increase the membrane permeability due to their ability to participate in halogen bonding and increase the overall hydrophobic character of the molecule.

4. **Carbonitrile Group**: The carbonitrile group, characterized by a nitrile functional group, can influence the molecule's polarity and hydrogen bonding capacity. While it may introduce some degree of polarity, the overall effect on permeability will depend on the balance with the other hydrophobic and hydrophilic components of the molecule.

In summary, the given molecule's structural features, such as the piperidine and thiazole rings, along with the bromophenyl and carbonitrile groups, suggest that it would exhibit high permeability in the PAMPA assay. These features collectively enhance the molecule's ability to interact with the artificial membrane, facilitating its passage through the membrane.

Final answer: High permeability

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# 137

**SMILES:** CC1=NOC(=C1S(=O)(=O)N2CCC(CC2)C(=O)NC3=CC=C(C=C3)C#N)/C=C/C4=CC=CC=C4F

**Label:** 0

**Predi:** 0

**Correct:** 1

# Response:
The given molecule is a piperidinecarboxamide, which is a type of compound featuring a piperidine ring attached to a carboxamide group. This structural motif is often associated with various pharmacological activities, and its permeability is crucial for its potential as a drug candidate.

The molecule contains several key structural features that influence its permeability:

1. **Piperidine Ring**: The presence of a piperidine ring contributes to the molecule's basicity and can enhance its ability to interact with biological membranes. Piperidine rings are commonly found in many bioactive compounds and can improve the molecule's solubility and permeability.

2. **Carboxamide Group**: The carboxamide group is polar and can form hydrogen bonds, which may facilitate interactions with the artificial membrane. This group can also contribute to the molecule's overall solubility in aqueous environments, which is important for permeability.

3. **1,2-Oxazole Ring**: The oxazole ring is a heterocyclic compound that can influence the molecule's electronic properties. Its presence may affect the molecule's ability to permeate the membrane by altering its lipophilicity and electronic distribution.

4. **Fluorophenyl Group**: The fluorophenyl moiety is a lipophilic group that can enhance the molecule's ability to penetrate lipid membranes. The presence of the fluorine atom can also increase the molecule's metabolic stability and binding affinity to target proteins.

5. **Ethylene Linkage**: The ethylene linkage between the fluorophenyl group and the rest of the molecule provides flexibility, which can help the molecule to adapt its conformation when interacting with the membrane.

6. **Cyano Group**: The cyano group is a polar functional group that can participate in hydrogen bonding and dipole-dipole interactions. This group can influence the molecule's solubility and permeability by affecting its overall polarity.

Overall, the given molecule's combination of lipophilic and polar groups suggests that it may have moderate permeability in the PAMPA assay. The balance of these groups allows the molecule to interact with both hydrophilic and hydrophobic environments, which is essential for effective permeation through biological membranes.

Final answer: Low-to-moderate permeability.

------
# 138

**SMILES:** CC(C)(C#N)C1=CC=C(C=C1)C2=NC=C(C=C2)CN3CCN(CC3)C

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a complex organic compound that features several functional groups and structural elements that influence its permeability in the PAMPA assay. Let's break down these features and their impact on permeability:

1. **Pyridine Rings**: The molecule contains two pyridine rings. Pyridine is a basic heterocyclic aromatic organic compound similar to benzene, but with one nitrogen atom replacing one CH group. The presence of these pyridine rings can enhance the molecule's ability to interact with the artificial membrane through π-π stacking interactions and hydrogen bonding, which can facilitate its passage through the membrane.

2. **Tert-butyl Group**: The molecule includes a tert-butyl group, which is a bulky alkyl group. This group can increase the lipophilicity of the molecule, enhancing its ability to permeate through lipid membranes. However, the steric hindrance introduced by the tert-butyl group may also limit the molecule's ability to fit into certain membrane pores, potentially reducing its permeability.

3. **Methyl Group**: The presence of a methyl group attached to the nitrile functionality can increase the molecule's hydrophobic character, which may enhance its permeability through the lipid-rich regions of the artificial membrane.

4. **Nitrile Group**: The nitrile group is a polar functional group that can participate in hydrogen bonding and dipole-dipole interactions. While this group can increase the molecule's solubility in polar environments, it may also hinder permeability due to its polar nature, which can limit interaction with the lipid components of the membrane.

Overall, the given molecule's structure suggests a balance between hydrophobic and hydrophilic properties. The pyridine rings and methyl group contribute to its hydrophobic character, potentially enhancing permeability, while the nitrile group and tert-butyl group introduce polar and steric elements that may limit permeability. In the context of the PAMPA assay, these factors suggest that the given molecule likely exhibits moderate permeability, balancing between hydrophilic and hydrophobic interactions with the artificial membrane.

Final answer: Low-to-moderate permeability.

------
# 139

**SMILES:** C1=CC=C(C(=C1)CNC2=CC=C(C=C2)S(=O)(=O)NC3=NC=CS3)O

**Label:** 0

**Predi:** 0

**Correct:** 1

# Response:
The given molecule is a sulfonamide, which is a class of compounds known for their antibacterial properties. The sulfonamide group is characterized by the presence of a sulfonyl functional group attached to an amine. This group is known to enhance the molecule's ability to interact with biological membranes due to its polar nature, which can facilitate hydrogen bonding and ionic interactions.

The structure of the given molecule includes a sulfonamide group attached to a phenyl ring, which is further substituted with a hydroxymethyl group. This hydroxymethyl group can increase the molecule's hydrophilicity, potentially improving its solubility in aqueous environments and enhancing its ability to permeate biological membranes.

Additionally, the molecule contains a thiazole ring, which is a five-membered heterocyclic compound containing both sulfur and nitrogen. The presence of the thiazole ring can contribute to the molecule's overall stability and may also play a role in its ability to permeate membranes due to its aromatic nature, which can facilitate interactions with lipid bilayers.

The phenyl ring linked to the thiazole moiety suggests a planar structure, which can enhance the molecule's ability to intercalate into lipid bilayers, potentially increasing its permeability.

Overall, the combination of the sulfonamide group, the hydroxymethyl group, and the thiazole ring in the given molecule suggests that it may have moderate to high permeability in the PAMPA assay, as these structural features can enhance its interaction with the artificial membrane.

Final answer: Low-to-moderate permeability.

------
# 140

**SMILES:** COC1=CC2=C(C=C1)NC(=O)C(=C2)C3=NOC(=N3)C4=CC(=CC=C4)OC

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several distinct structural components, each contributing to its permeability characteristics in the PAMPA assay.

Firstly, the molecule contains a quinoline moiety, which is a bicyclic structure consisting of a benzene ring fused to a pyridine ring. Quinoline derivatives are known for their ability to interact with biological membranes due to their planar aromatic structure, which can facilitate passage through lipid bilayers. This characteristic often results in moderate to high permeability in PAMPA assays.

Additionally, the molecule includes a 1,2,4-oxadiazole ring, a five-membered heterocyclic ring containing two nitrogen atoms and one oxygen atom. This ring is known for its electron-withdrawing properties, which can influence the overall polarity of the molecule. The presence of the oxadiazole ring may enhance the molecule's ability to interact with polar sites on the artificial membrane, potentially increasing its permeability.

The methoxy groups present in the molecule, one attached to the phenyl ring and another to the quinoline moiety, contribute to the molecule's lipophilicity. Methoxy groups can increase the hydrophobic character of a molecule, which may enhance its ability to permeate lipid membranes. However, they can also introduce steric hindrance, which might reduce permeability by limiting the molecule's ability to fit through the membrane pores.

Overall, the combination of the quinoline core, the oxadiazole ring, and the methoxy substituents suggests that the given molecule would exhibit high permeability in the PAMPA assay. The aromatic and heterocyclic components facilitate membrane interaction, while the methoxy groups enhance lipophilicity, contributing to its ability to permeate the artificial membrane.

Final answer: High permeability.

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# 141

**SMILES:** CC1=C(C=C(C=C1)N2C3=NC=NC(=C3C=N2)NC(C)COC)C

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a member of pyrazolopyrimidines, which are known for their potential biological activity, often used in pharmaceuticals. The structure of the given molecule includes a pyrazolo[3,4-d]pyrimidine core, which is a bicyclic system combining a pyrazole and a pyrimidine ring. This core is significant in drug design due to its ability to interact with various biological targets.

The presence of the pyrazolo[3,4-d]pyrimidine core suggests that the given molecule may have a planar structure, which can facilitate interactions with biological membranes. The aromatic nature of the pyrazolo[3,4-d]pyrimidine core can enhance the molecule's ability to penetrate lipid membranes due to π-π interactions and hydrophobic effects.

Additionally, the molecule has a 3,4-dimethylphenyl group attached to the pyrazolo[3,4-d]pyrimidine core. The dimethylphenyl group increases the hydrophobic character of the molecule, which can further enhance its ability to permeate lipid membranes. The methyl groups can also contribute to steric effects, potentially affecting the molecule's binding affinity and selectivity.

The N-(1-methoxypropan-2-yl) moiety introduces a methoxy group, which can increase the molecule's polarity and solubility in aqueous environments. This balance between hydrophobic and hydrophilic properties is crucial for the molecule's permeability, as it can facilitate crossing of the lipid bilayer while maintaining solubility in the aqueous environment of the bloodstream.

Overall, the combination of the pyrazolo[3,4-d]pyrimidine core, the dimethylphenyl group, and the methoxypropan-2-yl moiety suggests that the given molecule likely exhibits high permeability in the PAMPA assay, allowing it to effectively interact with biological membranes.

Final answer: High permeability

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# 142

**SMILES:** CC1=CC=C(C=C1)S(=O)(=O)N2C=C(C3=CC=CC=C32)C(=O)NC4=NC(=CS4)C5=CC=CC=C5

**Label:** 0

**Predi:** 1

**Correct:** 0

# Response:
The given molecule is a complex organic compound that includes several functional groups and aromatic rings, which influence its permeability in the PAMPA assay. Let's break down the structural components and their impact on permeability:

1. **Indole Moiety**: The presence of the indole structure, which is a bicyclic compound consisting of a benzene ring fused to a pyrrole ring, contributes to the molecule's aromaticity and planarity. This can enhance the molecule's ability to interact with the artificial membrane, potentially increasing its permeability due to favorable π-π stacking interactions with the membrane.

2. **Sulfonyl Group**: The sulfonyl group attached to the phenyl ring introduces a polar and electron-withdrawing character. This can increase the molecule's solubility in polar solvents, which is beneficial for permeability in the PAMPA assay. However, the sulfonyl group can also introduce steric hindrance, which might limit the molecule's ability to pass through the membrane.

3. **Carboxamide Group**: The carboxamide group is a polar functional group that can form hydrogen bonds with the artificial membrane. This can enhance the molecule's interaction with the membrane, potentially increasing its permeability. However, the presence of this group can also increase the molecule's overall polarity, which might reduce its ability to permeate the membrane if it is not balanced with sufficient hydrophobic interactions.

4. **Phenyl and 4-Methylphenyl Groups**: These aromatic rings contribute to the hydrophobic character of the molecule. The presence of these rings can facilitate interactions with the hydrophobic regions of the artificial membrane, potentially increasing permeability. The methyl group on the phenyl ring can also add to the hydrophobic interactions, although it is relatively small and may not significantly hinder permeability.

Overall, the given molecule contains a balance of hydrophobic and hydrophilic components, with aromatic structures that can facilitate interactions with the artificial membrane. The presence of polar groups like the sulfonyl and carboxamide may enhance solubility and interaction with the membrane, while the aromatic rings contribute to hydrophobic interactions. Considering these factors, the given molecule is likely to exhibit high permeability in the PAMPA assay.

Final answer: High permeability

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# 143

**SMILES:** CC1=C(C=C(C=C1)N2C3=NC=NC(=C3C=N2)NCCCN4C=CN=C4)Cl

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several distinct structural components, each contributing to its permeability characteristics in the PAMPA assay.

1. **Pyrazolo[3,4-d]pyrimidine Core**: This bicyclic structure is a key feature of the given molecule. Pyrazolo[3,4-d]pyrimidines are known for their planar aromatic systems, which can facilitate interactions with the artificial membrane. The aromaticity and rigidity of this core can enhance the molecule's ability to traverse the membrane, contributing to high permeability.

2. **Imidazole Ring**: The presence of an imidazole ring, linked via a propyl chain, introduces additional aromatic character and potential for hydrogen bonding. Imidazole rings are often involved in interactions with biological membranes due to their ability to form hydrogen bonds and π-π stacking interactions. This can further enhance the molecule's permeability.

3. **Aromatic Substituents**: The given molecule contains a 3-chloro-6-methylphenyl group. The chloro substituent can increase lipophilicity, which generally enhances membrane permeability. The methyl group can also contribute to the molecule's overall hydrophobic character, aiding in its passage through the lipid-rich environment of the artificial membrane.

4. **Amine Linkages**: The presence of amine groups, such as the primary amine linked to the imidazole ring, can increase the molecule's ability to form hydrogen bonds with the membrane. This can facilitate interaction with the membrane's polar head groups, potentially enhancing permeability.

Overall, the combination of aromatic systems, lipophilic substituents, and hydrogen bonding capabilities suggests that the given molecule is likely to exhibit high permeability in the PAMPA assay. The structural features promote interactions with the artificial membrane, allowing the molecule to effectively traverse it.

Final answer: High permeability

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# 144

**SMILES:** CCN1CCN(CC1)C(=O)CCCN2C(=O)C3=NN(C(=C3C(=N2)C)C)C4=CC=C(C=C4)C

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several functional groups and structural elements that influence its permeability in the PAMPA assay. Let's break down the key structural components and their impact on permeability:

1. **Pyrazolopyridazine Core**: The central structure of the given molecule is a pyrazolopyridazine, which is a bicyclic system combining pyrazole and pyridazine rings. This core is relatively planar and aromatic, which can enhance the molecule's ability to interact with the artificial membrane through π-π stacking interactions. However, the presence of nitrogen atoms in the rings can also introduce hydrogen bonding capabilities, which may affect the molecule's solubility and permeability.

2. **Methyl and Phenyl Substituents**: The presence of dimethyl groups and a 4-methylphenyl group on the pyrazolopyridazine core increases the hydrophobic character of the molecule. These groups can enhance lipophilicity, which is often associated with higher permeability through lipid membranes. The 4-methylphenyl group, in particular, can contribute to van der Waals interactions with the membrane.

3. **Piperazine and Carbonyl Groups**: The piperazine moiety, linked via a propyl chain, introduces a basic nitrogen atom that can be protonated under physiological conditions, potentially enhancing solubility in aqueous environments. The carbonyl group adjacent to the piperazine ring can participate in hydrogen bonding, which may influence the molecule's interaction with the membrane and its overall permeability.

4. **Ethyl Linker**: The ethyl chain connecting the piperazine to the pyrazolopyridazine core provides flexibility and spatial separation between the functional groups. This flexibility can allow the molecule to adopt conformations that optimize interactions with the membrane.

Overall, the given molecule's combination of aromatic, hydrophobic, and polar functional groups suggests that it may exhibit moderate to high permeability in the PAMPA assay. The balance of lipophilic and hydrophilic properties, along with the ability to form various non-covalent interactions, supports its potential to traverse the artificial membrane.

Final answer: High permeability

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# 145

**SMILES:** CC1=CC=CC=C1C(=O)N2CCC3=C2C=CC(=C3)C4=C(SC(=N4)NC(=O)CC5=CC6=C(C=C5)OCCO6)C

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several distinct structural components, each contributing to its permeability characteristics in the PAMPA assay.

1. **Indole Moiety**: The presence of the dihydroindole group suggests that the molecule has a relatively planar and aromatic character. Indole structures are known for their ability to participate in π-π stacking interactions, which can enhance the molecule's ability to interact with the artificial membrane. This aromaticity can contribute to the molecule's permeability by facilitating its passage through the membrane.

2. **Thiazole Ring**: The thiazole ring is a heterocyclic compound containing both sulfur and nitrogen. This ring can enhance the molecule's lipophilicity, which is a key factor in membrane permeability. The presence of the thiazole ring can also contribute to the molecule's ability to form hydrogen bonds, which may aid in its interaction with the membrane.

3. **Dihydrobenzodioxin Group**: This moiety introduces additional aromaticity and potential for hydrogen bonding due to the presence of oxygen atoms. The benzodioxin structure can increase the molecule's overall hydrophobicity, which is beneficial for permeability through lipid membranes. The oxygen atoms can also participate in polar interactions, which may help the molecule to orient itself correctly within the membrane.

4. **Acetamide Linkage**: The acetamide group provides a polar site that can engage in hydrogen bonding with the membrane. This functional group can enhance the molecule's solubility in aqueous environments, which is important for its transport across the membrane.

5. **Methyl Substituents**: The methyl groups attached to the benzodioxin and phenyl rings increase the hydrophobic character of the molecule. These groups can enhance the molecule's ability to interact with the lipid components of the artificial membrane, promoting permeability.

Overall, the given molecule's combination of aromatic, heterocyclic, and polar functional groups suggests that it has a balanced profile of hydrophobic and hydrophilic properties. This balance is likely to facilitate its passage through the artificial membrane, indicating that the molecule would exhibit high permeability in the PAMPA assay.

Final answer: High permeability

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# 146

**SMILES:** C1=CC(=CC(=C1)C2=CN3C=NC=C3C(=C2)C4=CN=CC=C4)CO

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound with multiple aromatic rings and functional groups that influence its permeability in the PAMPA assay. 

The structure of the given molecule includes a pyridine ring, an imidazo[1,2-a]pyridine moiety, and a phenyl group with a methanol substituent. The presence of these aromatic rings suggests that the molecule has a planar structure, which can facilitate interactions with the artificial membrane, potentially enhancing permeability. Aromatic rings are known for their ability to participate in π-π stacking interactions, which can stabilize the molecule's interaction with the membrane.

The imidazo[1,2-a]pyridine moiety is a bicyclic structure that can contribute to the molecule's rigidity and planarity, further supporting its interaction with the membrane. This moiety may also introduce basic nitrogen atoms, which can form hydrogen bonds or ionic interactions with the membrane, potentially increasing permeability.

The methanol group attached to the phenyl ring introduces a polar functional group, which can enhance the molecule's solubility in aqueous environments. This hydrophilic character can improve the molecule's ability to interact with the polar head groups of the artificial membrane, potentially increasing permeability.

Overall, the combination of aromatic rings, the imidazo[1,2-a]pyridine moiety, and the methanol group suggests that the given molecule is likely to have high permeability in the PAMPA assay due to its ability to engage in various non-covalent interactions with the artificial membrane.

Final answer: High permeability

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# 147

**SMILES:** CC1=C(C=CC(=C1)SCC2=C(N=C(S2)C3=CC(=C(C=C3)C(F)(F)F)F)C)OCC(=O)O

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound with several functional groups and structural features that influence its permeability in the PAMPA assay. Let's break down these features and their impact on permeability:

1. **Thiazole Ring**: The presence of a thiazole ring, which is a five-membered heterocyclic compound containing both sulfur and nitrogen, can contribute to the molecule's stability and rigidity. This structural feature can enhance the molecule's ability to interact with the artificial membrane, potentially increasing its permeability.

2. **Fluorinated Aromatic Ring**: The given molecule contains a phenyl ring substituted with fluorine atoms. Fluorine atoms can increase the lipophilicity of the molecule, which often enhances membrane permeability. The presence of trifluoromethyl groups can also increase the molecule's metabolic stability, which may further support its permeability.

3. **Trifluoromethyl Group**: The trifluoromethyl group is known for its electron-withdrawing properties, which can affect the electronic distribution within the molecule. This can influence the molecule's ability to interact with the membrane, potentially enhancing its permeability.

4. **Phenoxy and Acetic Acid Moieties**: The phenoxy group, which is an ether linkage, can increase the molecule's flexibility and solubility, potentially aiding in its permeability. The acetic acid moiety introduces a carboxylic acid group, which can enhance the molecule's solubility in aqueous environments, facilitating its interaction with the membrane.

5. **Methylthio Linkage**: The presence of a methylthio group (a sulfur-containing linkage) can contribute to the molecule's lipophilicity, which is often associated with increased membrane permeability.

Overall, the combination of these structural features suggests that the given molecule likely exhibits high permeability in the PAMPA assay. The balance of lipophilic and hydrophilic properties, along with the presence of functional groups that enhance stability and solubility, supports its ability to traverse the artificial membrane.

Final answer: High permeability

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# 148

**SMILES:** CC1=C(C(=CC=C1)CNC2=CC=C(C=C2)S(=O)(=O)NC3=NC=CS3)O

**Label:** 0

**Predi:** 1

**Correct:** 0

# Response:
The given molecule is a sulfonamide, which is a class of compounds known for their antibacterial properties. The sulfonamide group is characterized by the presence of a sulfonyl functional group attached to an amine. This group is known to enhance the molecule's ability to interact with biological targets, such as enzymes or receptors, due to its polar nature and ability to form hydrogen bonds.

In the given molecule, the sulfonamide group is attached to a benzene ring, which is further substituted with a hydroxy-methylphenyl group. The presence of the hydroxy group increases the molecule's hydrophilicity, which can enhance its solubility in aqueous environments and potentially improve its permeability across biological membranes.

Additionally, the molecule contains a thiazole ring, which is a five-membered heterocyclic compound containing both sulfur and nitrogen. The thiazole ring can contribute to the molecule's overall stability and ability to interact with biological targets, as it can participate in various non-covalent interactions, such as hydrogen bonding and π-π stacking.

The phenyl group linked to the thiazole ring provides a planar, aromatic structure that can facilitate interactions with hydrophobic regions of biological membranes. This aromatic character can also enhance the molecule's ability to permeate lipid bilayers due to its lipophilic nature.

Overall, the combination of the sulfonamide group, hydroxy group, and thiazole ring suggests that the given molecule may exhibit moderate to high permeability in the PAMPA assay, as these structural features can enhance its solubility, stability, and ability to interact with biological membranes.

Final answer: High permeability

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# 149

**SMILES:** C1=CC(=CC(=C1)OC(F)(F)F)NC(=O)C2=CC(=NN2)C3=CC=CN3

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several functional groups and structural elements that influence its permeability in the PAMPA assay. Let's break down these features and their impact on permeability:

1. **Aromatic Rings**: The molecule contains multiple aromatic rings, including a phenyl group and a pyrrole ring. Aromatic rings are generally hydrophobic, which can enhance the molecule's ability to interact with the lipid components of the artificial membrane. This interaction can facilitate the passage of the molecule through the membrane, contributing to high permeability.

2. **Trifluoromethoxy Group**: The presence of a trifluoromethoxy group on the phenyl ring introduces electron-withdrawing properties due to the highly electronegative fluorine atoms. This can increase the lipophilicity of the molecule, enhancing its ability to permeate through the lipid-rich environment of the artificial membrane.

3. **Pyrrole Ring**: The pyrrole ring is a five-membered heterocyclic aromatic compound that can contribute to the overall aromatic character of the molecule. This can also enhance lipophilicity and facilitate membrane permeation.

4. **Carboxamide Group**: The carboxamide group is a polar functional group that can form hydrogen bonds with the artificial membrane. While this group can increase the molecule's solubility in aqueous environments, its presence can also facilitate interactions with the membrane, potentially aiding in permeability.

5. **Overall Structure**: The combination of hydrophobic aromatic rings and polar functional groups suggests that the given molecule has a balanced lipophilic and hydrophilic character. This balance can enhance its ability to permeate the artificial membrane, as it can interact with both the lipid and aqueous phases.

In summary, the given molecule's structural features, including aromatic rings, a trifluoromethoxy group, and a carboxamide group, suggest that it would exhibit high permeability in the PAMPA assay. These features collectively enhance its ability to interact with the artificial membrane, facilitating its passage through the lipid-rich environment.

Final answer: High permeability.

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# 150

**SMILES:** C1CCC(CC1)C(=O)NCCC2=NC3=CC=CC=C3N2CCO

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a member of the benzimidazole class, which is known for its ability to interact with biological membranes due to its aromatic and heterocyclic structure. The benzimidazole moiety in the given molecule contributes to its potential for high permeability through the artificial membrane, as aromatic and heterocyclic compounds often have favorable interactions with lipid bilayers.

Additionally, the presence of the carboxamide group in the molecule can enhance its ability to form hydrogen bonds with the artificial membrane, potentially increasing its permeability. The carboxamide group can also contribute to the molecule's solubility and ability to interact with polar sites on the membrane.

The hydroxyethyl group attached to the ethyl chain provides an additional site for hydrogen bonding, which can further influence the molecule's interaction with the membrane. This group can enhance the molecule's solubility in aqueous environments, which is beneficial for permeability through the PAMPA, a model that mimics biological membranes.

Overall, the combination of the benzimidazole core, carboxamide group, and hydroxyethyl side chain suggests that the given molecule is likely to exhibit high permeability in the Parallel Artificial Membrane Permeability Assay.

Final answer: High permeability

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# 151

**SMILES:** COC1=CC=C(C=C1)NC2=NC(=NO2)C3=CC(=CC=C3)OC

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is characterized by the presence of a 1,2,4-oxadiazole ring, which is a five-membered heterocyclic ring containing two nitrogen atoms and one oxygen atom. This ring is known for its stability and ability to participate in hydrogen bonding and dipole interactions, which can influence the molecule's permeability.

Additionally, the molecule contains two methoxyphenyl groups. The methoxy group (-OCH3) is an electron-donating group that can enhance the lipophilicity of the molecule. This increased lipophilicity can improve the molecule's ability to permeate through lipid membranes, such as those found in biological systems.

The amine group attached to the oxadiazole ring can also play a role in permeability. Amines can form hydrogen bonds, which may facilitate interaction with the artificial membrane, potentially enhancing permeability.

Overall, the combination of the oxadiazole ring, methoxyphenyl groups, and the amine group suggests that the given molecule may exhibit high permeability in the PAMPA assay due to its balanced hydrophilic and lipophilic properties, which facilitate interaction with the artificial membrane.

Final answer: High permeability.

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# 152

**SMILES:** C1CNCCC1C2=CC=C(C=C2)NS(=O)(=O)C3=CC=C(C=C3)NCC4=C(C(=CC=C4)Cl)O

**Label:** 0

**Predi:** 0

**Correct:** 1

# Response:
The given molecule is a sulfonamide, which is a class of compounds known for their antibacterial properties. The sulfonamide group is characterized by the presence of a sulfonyl functional group attached to an amine. This group is known to enhance the molecule's ability to interact with biological targets, often through hydrogen bonding and ionic interactions.

In the given molecule, the sulfonamide group is attached to a phenyl ring, which is further substituted with a chloro group. The presence of the chloro group can influence the molecule's lipophilicity, potentially enhancing its ability to permeate lipid membranes. However, the chloro group can also introduce steric hindrance, which might affect the molecule's overall permeability.

Additionally, the molecule contains a hydroxy group attached to a piperidine ring. The hydroxy group can form hydrogen bonds, which may increase the molecule's solubility in aqueous environments and facilitate its interaction with polar sites on the artificial membrane.

The piperidine ring itself is a common structural motif in medicinal chemistry, often used to enhance the pharmacokinetic properties of a compound. Its presence in the given molecule suggests that it may contribute to the molecule's ability to traverse biological membranes by increasing its overall flexibility and conformational adaptability.

Overall, the combination of these functional groups suggests that the given molecule may exhibit moderate permeability in the artificial membrane assay. The sulfonamide group, along with the hydroxy and piperidine functionalities, likely contribute to a balance of hydrophilic and lipophilic properties, allowing the molecule to interact with the membrane while maintaining sufficient solubility.

Final answer: Low-to-moderate permeability.

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# 153

**SMILES:** CN1C(=NN=N1)SC2=NC=NC3=C2C(=CS3)Br

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a thienopyrimidine derivative, which is characterized by a fused bicyclic structure consisting of a thiophene ring and a pyrimidine ring. This core structure is known for its potential biological activity and is often used in pharmaceuticals.

The presence of a bromo substituent on the thiophene ring can influence the molecule's lipophilicity and electronic properties. Bromine is a relatively large and electronegative atom, which can increase the molecule's overall hydrophobicity and potentially enhance its ability to interact with lipid membranes.

The molecule also contains a tetrazole ring, which is a five-membered ring containing four nitrogen atoms. The tetrazole group is known for its ability to mimic the carboxylic acid group, often used in drug design to improve the pharmacokinetic properties of a compound. In this case, the tetrazole is linked to the thienopyrimidine core via a sulfanyl (thio) bridge, which can further influence the molecule's solubility and permeability.

The combination of these structural features suggests that the given molecule may have moderate to high permeability through the artificial membrane. The thienopyrimidine core provides a planar and aromatic structure that can facilitate passage through lipid bilayers, while the bromo substituent and the tetrazole group may enhance interactions with the membrane and improve overall permeability. However, the exact permeability would depend on the specific conditions of the PAMPA assay, such as the type of artificial membrane used and the presence of other competing molecules.

Final answer: Low-to-moderate permeability.

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# 154

**SMILES:** CC#CC(=O)N1CCC[C@H]1C2=NC(=C3N2C=CN=C3N)C4=CC=C(C=C4)C(=O)NC5=CC=CC=N5

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a complex organic compound with several functional groups and structural features that influence its permeability in the PAMPA assay. Let's analyze these features:

1. **Imidazo[1,2-a]pyrazine Core**: This bicyclic structure is a fused ring system that contributes to the rigidity and planarity of the molecule. Such structures often enhance the ability of a molecule to interact with biological membranes, potentially increasing permeability. However, the specific substituents on this core will also play a crucial role in determining the overall permeability.

2. **Amino Group**: The presence of an amino group can increase the molecule's polarity and hydrogen bonding capacity. This can enhance solubility in aqueous environments, which is beneficial for permeability through biological membranes. However, the balance between hydrophilicity and lipophilicity is crucial, and the presence of other hydrophobic groups may counteract this effect.

3. **Pyridine Carboxamide**: The pyridine ring is a heteroaromatic system that can contribute to the molecule's overall planarity and rigidity. The carboxamide group can participate in hydrogen bonding, which may facilitate interactions with the membrane or other molecules. The presence of this group can also influence the molecule's solubility and permeability.

4. **Prop-2-ynyl Group**: This alkyne group introduces a degree of hydrophobicity and rigidity to the molecule. Alkynes can also participate in π-π interactions, which may affect the molecule's interaction with the membrane.

5. **Pyrrolidine Ring**: The pyrrolidine ring is a saturated, non-aromatic five-membered ring that can add flexibility to the molecule. This flexibility can help the molecule adapt to the membrane's structure, potentially enhancing permeability.

6. **Overall Structure**: The combination of aromatic and aliphatic components, along with polar and non-polar groups, suggests that the given molecule has a balanced hydrophilic-lipophilic profile. This balance is often associated with moderate permeability in PAMPA assays, as it allows the molecule to interact with both the aqueous and lipid phases of the membrane.

In summary, the given molecule's structural features suggest that it has a balanced profile that could result in moderate permeability in the PAMPA assay. The presence of both hydrophilic and hydrophobic groups, along with a rigid and flexible framework, supports this conclusion.

Final answer: Low-to-moderate permeability.

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# 155

**SMILES:** CC1=CN=C(C(=C1OC)C)CS(=O)C2=NC3=C(N2)C=CC(=N3)OC

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a derivative of imidazopyridine, which is a bicyclic compound consisting of an imidazole ring fused to a pyridine ring. This core structure is known for its biological activity and is often used in pharmaceuticals.

The molecule features several functional groups that influence its permeability:

1. **Methoxy Groups**: The presence of methoxy groups on the pyridine ring increases the molecule's lipophilicity, which can enhance its ability to permeate lipid membranes. These groups can also influence the electronic properties of the aromatic ring, potentially affecting the molecule's interaction with the artificial membrane.

2. **Methyl Groups**: The methyl groups on the pyridine ring contribute to the hydrophobic character of the molecule, further increasing its lipophilicity. This can enhance membrane permeability by facilitating passage through the lipid bilayer.

3. **Sulfinyl Linkage**: The sulfinyl group connects the pyridine moiety to the imidazopyridine core. This linkage can influence the molecule's overall polarity and may affect its ability to interact with the artificial membrane. The presence of sulfur can also introduce potential sites for metabolic transformation, which may impact permeability.

4. **Imidazopyridine Core**: The imidazopyridine structure is relatively planar and aromatic, which can facilitate stacking interactions with the artificial membrane. This core structure is often associated with good membrane permeability due to its ability to interact with lipid bilayers.

Overall, the combination of methoxy and methyl groups increases the lipophilicity of the given molecule, which is likely to enhance its permeability through the artificial membrane. The sulfinyl linkage and imidazopyridine core contribute to the molecule's ability to interact with the membrane, potentially allowing for moderate to high permeability.

Final answer: High permeability

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# 156

**SMILES:** C1CN(CCC1C2=NOC3=C2C=CC(=C3)F)C(=O)C4CC(=O)N(C4)C5=NNC6=CC=CC=C65

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound with several distinct structural features that influence its permeability in the PAMPA assay. Let's break down these features and their implications:

1. **Indazole Moiety**: The presence of the indazole ring, which is a bicyclic structure consisting of a benzene ring fused to a pyrazole ring, contributes to the molecule's aromaticity and planarity. This can enhance the molecule's ability to interact with the artificial membrane through π-π stacking interactions, potentially increasing its permeability.

2. **Fluorine Substitution**: The fluorine atom attached to the indazole ring is electronegative and can influence the electronic distribution within the molecule. This can affect the molecule's lipophilicity, potentially enhancing its ability to traverse lipid membranes by increasing its overall hydrophobic character.

3. **Benzoxazole Moiety**: The benzoxazole ring is another aromatic system that can contribute to the molecule's overall stability and ability to interact with the membrane. The presence of this heterocyclic structure can also enhance the molecule's ability to form hydrogen bonds, which may facilitate its passage through the membrane.

4. **Piperidinone Structure**: The piperidinone ring is a six-membered ring containing a ketone group. This structure can provide a degree of flexibility and polarity to the molecule, which may influence its permeability. The ketone group can participate in hydrogen bonding, potentially aiding in the molecule's interaction with the membrane.

5. **Overall Molecular Size and Complexity**: The given molecule is relatively large and complex, which can affect its permeability. While larger molecules may have more surface area to interact with the membrane, they may also face steric hindrance or difficulty in fitting through the membrane pores.

In summary, the given molecule's aromatic and heterocyclic structures, along with the presence of a fluorine atom, suggest that it may have a moderate to high permeability in the PAMPA assay. The balance of hydrophobic and hydrophilic interactions, along with the molecule's size and flexibility, will ultimately determine its ability to permeate the artificial membrane.

Final answer: High permeability

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# 157

**SMILES:** CC1=CC=C(C=C1)S(=O)(=O)NC2=CN=CC(=C2)C(=O)NC3=NC(=CS3)C4=CC=CC=C4

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a sulfonamide, which is a class of compounds known for their antibacterial properties. The sulfonamide group is characterized by the presence of a sulfonyl functional group attached to an amine. In this molecule, the sulfonamide group is linked to a phenyl ring, which can influence its lipophilicity and, consequently, its permeability.

The molecule also contains a thiazole ring, which is a five-membered heterocyclic compound containing both sulfur and nitrogen. This ring can contribute to the molecule's electronic properties, potentially affecting its interaction with the artificial membrane.

Additionally, the molecule features a pyridine ring, which is a six-membered heterocyclic aromatic ring containing nitrogen. Pyridine rings are known for their ability to participate in hydrogen bonding and π-π interactions, which can influence the molecule's permeability by affecting its solubility and interaction with the membrane.

The presence of these functional groups and heterocyclic rings suggests that the given molecule may have moderate permeability due to the balance between hydrophilic and lipophilic properties. The sulfonamide group can enhance solubility in aqueous environments, while the aromatic rings and heteroatoms can facilitate interactions with the lipid components of the artificial membrane.

Overall, the combination of these structural features suggests that the given molecule would exhibit low-to-moderate permeability in the Parallel Artificial Membrane Permeability Assay (PAMPA).

Final answer: Low-to-moderate permeability.

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# 158

**SMILES:** CC1=C(C=C(C=C1)NC(=O)C2=C(C(=C(N2)C)C(=O)C)C)[S+](=O)(NC3=CC=C(C=C3)Br)[O-]

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several functional groups and structural elements that influence its permeability in the PAMPA assay. Let's break down the key components and their impact on permeability:

1. **Pyrrole Ring**: The presence of a pyrrole ring, which is a five-membered aromatic heterocycle containing nitrogen, contributes to the molecule's aromaticity and potential for hydrogen bonding. This can enhance the molecule's ability to interact with the artificial membrane, potentially increasing its permeability.

2. **Acetyl Group**: The acetyl group attached to the pyrrole ring introduces a polar carbonyl group, which can form hydrogen bonds with the membrane. This can increase the molecule's solubility in the membrane environment, potentially enhancing its permeability.

3. **Dimethyl Substitution**: The dimethyl groups on the pyrrole ring increase the hydrophobic character of the molecule. This can affect the balance between hydrophilicity and lipophilicity, which is crucial for permeability. In general, increased hydrophobicity can enhance membrane permeability due to better interaction with the lipid bilayer.

4. **Aryl Sulfide Linkage**: The sulfanyl (thioether) linkage connects the pyrrole moiety to an aryl group. Thioethers are generally non-polar and can contribute to the lipophilicity of the molecule. This can facilitate passage through the lipid-rich environment of the artificial membrane.

5. **Aryl Amide Linkage**: The amide linkage between the pyrrole and the aryl sulfide group introduces a polar site that can participate in hydrogen bonding. This can enhance solubility and interaction with the membrane, potentially increasing permeability.

6. **Bromophenyl Group**: The presence of a bromine atom on the phenyl ring adds to the molecule's overall lipophilicity and can also influence its electronic properties. The bromine atom can enhance the molecule's ability to interact with the membrane through van der Waals forces.

7. **Methoxyphenyl Group**: The methoxy group on the phenyl ring is an electron-donating group that can increase the electron density of the aromatic ring. This can affect the molecule's interaction with the membrane and its overall stability in the environment.

Overall, the given molecule exhibits a balance of hydrophilic and lipophilic properties due to its diverse functional groups. The presence of aromatic rings, polar groups, and hydrophobic substituents suggests that the molecule would have moderate to high permeability in the PAMPA assay, as it can effectively interact with both the aqueous and lipid phases of the membrane.

Final answer: High permeability

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# 159

**SMILES:** C1CN(CCC1C(=O)N)C2=NC(=CS2)C3=CC=C(C=C3)OC4=CC=CC=C4

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is characterized by several key structural features that influence its permeability in the PAMPA assay. 

Firstly, the presence of the phenoxyphenyl group indicates that the molecule has aromatic rings, which can enhance lipophilicity. Aromatic rings are known to facilitate membrane permeability due to their ability to interact with lipid bilayers through π-π interactions and van der Waals forces. This can increase the molecule's ability to traverse the artificial membrane.

Secondly, the thiazole ring is a heterocyclic compound containing both sulfur and nitrogen. This ring can contribute to the molecule's overall polarity and hydrogen bonding potential, which may affect its permeability. The thiazole ring can also participate in additional interactions with the membrane, potentially enhancing permeability.

The piperidine ring is a saturated nitrogen-containing heterocycle that can increase the molecule's solubility and overall stability. This ring can also contribute to the molecule's basicity, which may influence its interaction with the artificial membrane.

Finally, the carboxamide group is a polar functional group that can form hydrogen bonds with the membrane. This group can enhance the molecule's solubility in aqueous environments, which is important for permeability in the PAMPA assay.

Overall, the combination of aromatic rings, heterocyclic structures, and polar functional groups in the given molecule suggests that it would exhibit high permeability in the PAMPA assay due to its ability to interact with the artificial membrane through various non-covalent interactions.

Final answer: High permeability.

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# 160

**SMILES:** CC1=C(C2=C(N1C3=CC=CC=C3)C=CC(=C2)O)C(=O)C

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a derivative of indole, which is a bicyclic structure consisting of a benzene ring fused to a pyrrole ring. This core structure is known for its planar and aromatic characteristics, which can influence the molecule's interaction with biological membranes.

The presence of a hydroxy group on the indole ring introduces a polar functional group, which can form hydrogen bonds with the artificial membrane. This can enhance the molecule's solubility in aqueous environments and potentially increase its permeability through the membrane.

Additionally, the methyl group on the indole ring can contribute to the molecule's hydrophobic interactions with the membrane, potentially aiding in its permeation.

The phenyl group attached to the indole structure adds further hydrophobic character, which can facilitate the molecule's passage through the lipid bilayer of the artificial membrane.

The ethanone group, which is a carbonyl functional group, can also participate in hydrogen bonding and dipole-dipole interactions, which may further influence the molecule's permeability.

Overall, the combination of aromatic, hydrophobic, and polar functional groups in the given molecule suggests that it may have moderate to high permeability through the artificial membrane, as these features can facilitate interactions with both the lipid and aqueous phases of the membrane.

Final answer: High permeability.

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# 161

**SMILES:** CC1=CC(=NC(=C1)NC(=S)N2CCN(CC2)C3=CC(=CC=C3)[N+](=O)[O-])C

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a complex organic compound that features several functional groups and structural elements that influence its permeability in the PAMPA assay. Let's break down these features and their impact on permeability:

1. **Piperazine Ring**: The presence of a piperazine ring, which is a six-membered heterocyclic compound containing two nitrogen atoms, contributes to the molecule's basicity and potential for hydrogen bonding. Piperazine rings are often found in pharmaceuticals and can enhance the solubility and permeability of the molecule due to their ability to interact with biological membranes.

2. **Dimethylphenyl Group**: The dimethylphenyl moiety introduces hydrophobic characteristics to the molecule. The methyl groups can increase the lipophilicity, which may enhance the ability of the molecule to traverse lipid membranes. However, the balance between hydrophilic and hydrophobic properties is crucial for permeability.

3. **Nitrophenyl Group**: The nitro group on the phenyl ring is a strong electron-withdrawing group, which can affect the electronic distribution of the molecule. This can influence the molecule's interaction with the artificial membrane, potentially reducing permeability due to increased polarity and potential for ionic interactions.

4. **Carbothioamide Group**: The carbothioamide functional group introduces both sulfur and nitrogen atoms, which can participate in hydrogen bonding and other polar interactions. This group can enhance the molecule's solubility in aqueous environments and may facilitate its passage through the membrane.

5. **Pyridine Ring**: The pyridine ring is a heteroaromatic structure that can contribute to the molecule's overall stability and ability to interact with biological targets. The nitrogen in the pyridine ring can participate in hydrogen bonding and coordinate with metal ions, which may affect the molecule's permeability.

Overall, the given molecule exhibits a balance of hydrophilic and hydrophobic properties, with potential for hydrogen bonding and ionic interactions. The presence of the piperazine ring and carbothioamide group suggests that the molecule may have moderate to high permeability in the PAMPA assay, as these features can facilitate interaction with the artificial membrane. However, the nitrophenyl group may slightly reduce permeability due to its electron-withdrawing nature and potential for ionic interactions.

Final answer: Low-to-moderate permeability.

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# 162

**SMILES:** C1CC2=C(C(N=C(N2)NC3=NC4=C(O3)C=CC(=C4)F)C5=C(C=NN5)Cl)C(=O)C1

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound with several functional groups and heterocyclic rings that influence its permeability in the PAMPA assay. Let's break down the structural features and their impact on permeability:

1. **Quinazoline Core**: The quinazoline moiety is a bicyclic structure that is relatively planar and aromatic. This contributes to the molecule's ability to interact with the artificial membrane through π-π stacking and hydrophobic interactions. The presence of a chlorine atom on the quinazoline ring can enhance lipophilicity, which generally increases membrane permeability.

2. **Benzoxazole Ring**: The benzoxazole ring is another aromatic system that can contribute to the molecule's overall hydrophobic character. The presence of a fluorine atom on this ring can further increase lipophilicity and membrane permeability due to the strong electronegativity of fluorine, which can enhance the molecule's ability to penetrate lipid membranes.

3. **Pyrimidine Ring**: The pyrimidine ring is a heterocyclic aromatic compound that can participate in hydrogen bonding due to the presence of nitrogen atoms. This can affect the molecule's solubility and permeability. The oxo group (carbonyl) on the pyrimidine ring can also engage in hydrogen bonding, potentially influencing the molecule's interaction with the membrane.

4. **Amino Linkage**: The amino group connecting the pyrimidine and quinazoline rings can act as a hydrogen bond donor or acceptor, which may facilitate interactions with the membrane or other molecules in the environment.

Overall, the given molecule has a combination of aromatic and heterocyclic structures, along with functional groups that can enhance lipophilicity and facilitate interactions with the artificial membrane. These features suggest that the molecule would exhibit high permeability in the PAMPA assay, allowing it to effectively traverse the membrane.

Final answer: High permeability

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# 163

**SMILES:** C1CC(=O)NC2=CC(=C(C=C21)S(=O)(=O)NC3=CC(=C(C=C3)F)Cl)F

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a quinoline derivative, which is a class of compounds known for their diverse biological activities. The quinoline core is a bicyclic structure consisting of a benzene ring fused to a pyridine ring. This core structure is known for its planar and aromatic nature, which can facilitate interactions with biological membranes.

The molecule contains several functional groups that influence its permeability:

1. **Sulfonamide Group**: The presence of a sulfonamide group is significant for permeability. Sulfonamides are known to enhance the solubility of compounds, which can improve their ability to permeate biological membranes. This group can also participate in hydrogen bonding, which may aid in the interaction with the artificial membrane.

2. **Chloro and Fluoro Substituents**: The chloro and fluoro groups on the phenyl ring and the quinoline core can influence the lipophilicity of the molecule. These halogen atoms can increase the molecule's ability to penetrate lipid membranes due to their electron-withdrawing properties, which can enhance the overall hydrophobic character of the molecule.

3. **Fluoro Substituent on Quinoline**: The fluoro group on the quinoline ring can further modulate the electronic properties of the molecule, potentially affecting its interaction with the artificial membrane. Fluorine atoms can increase the metabolic stability of the molecule, which may prolong its activity in biological systems.

4. **Keto Group**: The presence of a keto group in the quinoline ring can also play a role in the molecule's permeability. This group can participate in hydrogen bonding, which may affect the molecule's solubility and interaction with the membrane.

Overall, the combination of these functional groups suggests that the given molecule may exhibit high permeability in the PAMPA assay. The aromatic quinoline core, along with the electron-withdrawing halogens and the sulfonamide group, likely contribute to its ability to traverse the artificial membrane.

Final answer: High permeability

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# 164

**SMILES:** CCCCCN1C(=O)C2=C(C=C(C=C2)C(=O)NCCCN3CCC(CC3)C)NC1=O

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a quinazoline derivative, which is a class of compounds known for their diverse biological activities. The quinazoline core is a bicyclic structure consisting of a benzene ring fused to a pyrimidine ring. This core is known for its planar structure, which can facilitate interactions with biological targets, such as enzymes or receptors.

The molecule contains several functional groups and side chains that influence its permeability:

1. **Quinazoline Core**: The quinazoline structure is relatively planar and hydrophobic, which can enhance the molecule's ability to permeate lipid membranes. This is due to the aromatic nature of the benzene and pyrimidine rings, which can engage in π-π interactions with the lipid bilayer.

2. **Carboxamide Group**: The presence of a carboxamide group introduces a polar character to the molecule. This group can form hydrogen bonds with the artificial membrane, potentially increasing its interaction with the membrane and enhancing permeability.

3. **Piperidine Ring**: The piperidine moiety is a six-membered nitrogen-containing ring that can increase the molecule's solubility and permeability. The basic nitrogen in the piperidine ring can participate in ionic interactions with the membrane, which may facilitate passage through the lipid bilayer.

4. **Alkyl Chains**: The butyl and methylpropyl groups attached to the piperidine and quinazoline cores, respectively, contribute to the hydrophobic character of the molecule. These alkyl chains can enhance the molecule's ability to embed within the lipid membrane, promoting permeability.

Overall, the combination of the quinazoline core, polar carboxamide group, and hydrophobic alkyl chains suggests that the given molecule would exhibit high permeability in the Parallel Artificial Membrane Permeability Assay (PAMPA). The balance of hydrophobic and hydrophilic properties allows the molecule to effectively interact with the artificial membrane, facilitating its passage.

Final answer: High permeability

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# 165

**SMILES:** COC1=CC=CC=C1S(=O)(=O)NC2=C(C=CN=C2)C(=O)NC3=NC(=CS3)C4=CC=CC=C4

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a sulfonamide, which is a class of compounds known for their antimicrobial properties. The sulfonamide group is characterized by the presence of a sulfonyl functional group attached to an amine. This group is known to enhance the molecule's ability to interact with biological targets, often through hydrogen bonding and ionic interactions.

The molecule also contains a pyridine ring, which is a nitrogen-containing heterocycle. Pyridine rings are known to increase the solubility and bioavailability of compounds due to their basic nature and ability to participate in hydrogen bonding.

Additionally, the molecule features a thiazole ring, which is another nitrogen and sulfur-containing heterocycle. Thiazole rings are often found in bioactive compounds and can contribute to the molecule's ability to penetrate biological membranes due to their planar structure and electronic properties.

The presence of a phenyl group adds hydrophobic character to the molecule, which can enhance its ability to interact with lipid membranes. This hydrophobic interaction is crucial for the permeability of the molecule through the lipid bilayer of cell membranes.

The methoxy group attached to the benzene ring can increase the molecule's lipophilicity, potentially enhancing its permeability by increasing its ability to dissolve in lipid environments.

Overall, the combination of these functional groups suggests that the given molecule has a balance of hydrophilic and hydrophobic properties, which is likely to result in moderate permeability through the artificial membrane. The sulfonamide group, in particular, is known for its ability to interact with biological targets, which may also contribute to its permeability profile.

Final answer: Low-to-moderate permeability.

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# 166

**SMILES:** C1=CC(=C(C=C1Cl)C2=NC3=NC=CN=C3C(=N2)NC4=CC=NC=C4)F

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a pyrimidine derivative, which is a class of compounds known for their diverse biological activities. The structure of the given molecule includes a pyrimidine core, which is a six-membered heterocyclic aromatic ring containing two nitrogen atoms. This core is known for its ability to participate in hydrogen bonding and π-π stacking interactions, which can enhance the molecule's ability to interact with biological targets.

The presence of the pyridinyl groups attached to the pyrimidine core increases the molecule's polarity and potential for hydrogen bonding, which can influence its solubility and permeability. These groups can also contribute to the molecule's ability to interact with polar environments, such as those found in biological membranes.

The 2-chloro-6-fluorophenyl group introduces both lipophilic and electron-withdrawing characteristics to the molecule. The chloro and fluoro substituents can enhance the molecule's ability to penetrate lipid membranes by increasing its lipophilicity, while also affecting its electronic properties, which can influence its interaction with biological targets.

Overall, the combination of the pyrimidine core, pyridinyl groups, and the chloro-fluoro phenyl group suggests that the given molecule may have moderate permeability in the PAMPA assay. The balance of hydrophilic and lipophilic properties, along with the potential for hydrogen bonding and π-π interactions, indicates that the molecule can traverse the artificial membrane, but may require additional modifications to enhance its permeability if needed.

Final answer: Low-to-moderate permeability.

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# 167

**SMILES:** CC1(CNC2=C1C=CC(=C2)NC(=O)C3=C(N=CC=C3)NCC4=CC=NC=C4)C

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several functional groups and structural motifs that influence its permeability in the PAMPA assay. Let's break down the key structural elements and their impact on permeability:

1. **Indole Core**: The molecule contains an indole moiety, which is a bicyclic structure consisting of a benzene ring fused to a pyrrole ring. Indole derivatives are known for their ability to interact with biological membranes due to their planar structure and aromatic nature. This can facilitate passage through lipid bilayers, suggesting that the given molecule might exhibit moderate to high permeability.

2. **Dimethyl Substitution**: The presence of two methyl groups on the indole ring increases the hydrophobic character of the molecule. This hydrophobicity can enhance the molecule's ability to interact with the lipid components of the artificial membrane, potentially increasing its permeability.

3. **Pyridine Rings**: The molecule contains two pyridine rings, which are nitrogen-containing heterocycles. Pyridine rings can participate in hydrogen bonding and other polar interactions, which may influence the molecule's solubility and permeability. However, the presence of these rings can also introduce some degree of polarity, which might balance the hydrophobic effects of the indole and methyl groups.

4. **Carboxamide Linkage**: The carboxamide group is a polar functional group that can form hydrogen bonds. This group can enhance the molecule's solubility in aqueous environments, which is important for its interaction with the PAMPA membrane. The presence of this group may also contribute to the overall balance between hydrophobic and hydrophilic properties, potentially affecting permeability.

Overall, the given molecule's structure suggests that it has a balance of hydrophobic and hydrophilic characteristics, with the indole core and dimethyl substitution likely contributing to moderate to high permeability. The pyridine rings and carboxamide group may provide additional interactions with the membrane, further influencing its permeability profile. Therefore, the final answer is:

Final answer: High permeability.

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# 168

**SMILES:** COC1=CC=C(C=C1)N2C(=O)NC(=N2)C3CCN(CC3)[S+](=O)(C4=CC=CC(=C4)C(F)(F)F)[O-]

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound with several functional groups that influence its permeability in the PAMPA assay. Let's break down the structural features and their impact on permeability:

1. **Triazole Ring**: The presence of a triazole ring is significant as it is a heterocyclic compound that can enhance the molecule's stability and lipophilicity. This can contribute to moderate to high permeability as triazole rings are often involved in interactions with biological membranes.

2. **Methoxyphenyl Group**: The methoxy group attached to the phenyl ring increases the lipophilicity of the molecule. This can enhance the ability of the molecule to traverse lipid membranes, suggesting a higher permeability.

3. **Trifluoromethylphenyl Group**: The trifluoromethyl group is highly electronegative and lipophilic. This group can increase the molecule's ability to penetrate lipid bilayers, contributing to higher permeability. Additionally, the presence of fluorine atoms can enhance metabolic stability, which is beneficial for drug-like properties.

4. **Piperidine Ring**: The piperidine ring is a saturated nitrogen-containing heterocycle that can increase the molecule's solubility and permeability. It can also provide a basic site that may interact with acidic environments in the membrane, potentially aiding in permeation.

5. **Sulfonyl Group**: The sulfonyl group is polar and can enhance the molecule's solubility in aqueous environments. However, its presence can also introduce steric hindrance and reduce permeability due to its size and polarity.

Overall, the given molecule has a combination of lipophilic and polar groups that suggest moderate to high permeability in the PAMPA assay. The balance of hydrophobic and hydrophilic properties, along with the presence of the triazole and piperidine rings, likely facilitates its passage through the artificial membrane.

Final answer: High permeability

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# 169

**SMILES:** CC1CCCCN1C2=NC=NC(=C2[N+](=O)[O-])N

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a derivative of pyrimidine, which is a heterocyclic aromatic organic compound. The presence of the pyrimidine ring is significant as it is a common scaffold in many biologically active compounds, including nucleotides and various pharmaceuticals. This ring contributes to the molecule's ability to interact with biological targets, potentially enhancing its permeability.

The molecule also contains a nitro group attached to the pyrimidine ring. Nitro groups are electron-withdrawing and can influence the electronic properties of the molecule. This can affect the molecule's ability to permeate through biological membranes by altering its polarity and solubility. The presence of the nitro group may reduce the overall permeability due to its potential to increase the molecule's hydrophilicity.

Additionally, the molecule features a piperidine ring, which is a six-membered nitrogen-containing heterocycle. Piperidine rings are known to enhance the lipophilicity of molecules, which can improve their ability to permeate lipid membranes. The presence of the piperidine moiety in the given molecule suggests that it may have a favorable balance between hydrophilic and lipophilic properties, potentially enhancing its permeability.

Overall, the combination of the pyrimidine ring, the nitro group, and the piperidine moiety suggests that the given molecule may have moderate permeability. The pyrimidine and piperidine rings contribute to lipophilicity, while the nitro group may introduce some hydrophilic character, resulting in a balance that could facilitate passage through the artificial membrane.

Final answer: Low-to-moderate permeability.

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# 170

**SMILES:** CC1=CC(=NC(=C1)NC(=S)N2CCN(CC2)C3=C(C=C(C=C3)Cl)[N+](=O)[O-])C

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a complex organic compound that features several functional groups and structural elements that influence its permeability in the PAMPA assay. Let's break down these features and their impact on permeability:

1. **Piperazine Ring**: The presence of a piperazine ring, a six-membered heterocyclic structure containing two nitrogen atoms, is a key feature. Piperazine rings are known for their ability to enhance the solubility and permeability of molecules due to their basic nature and potential for hydrogen bonding. This can facilitate the passage of the molecule through the artificial membrane.

2. **Carbothioamide Group**: The carbothioamide group, which includes a thioamide linkage, can contribute to the molecule's overall polarity. This group can engage in hydrogen bonding and dipole-dipole interactions, which may enhance the molecule's interaction with the membrane and improve its permeability.

3. **Chloro and Nitro Substituents**: The chloro group on the phenyl ring and the nitro group on the pyridine ring introduce electron-withdrawing effects. These groups can influence the electronic distribution within the molecule, potentially affecting its ability to interact with the membrane. The chloro group can also enhance lipophilicity, which may aid in membrane permeability.

4. **Dimethylpyridine Moiety**: The dimethyl groups on the pyridine ring increase the lipophilicity of the molecule. This can enhance the ability of the molecule to traverse lipid membranes, contributing to its permeability.

5. **Overall Structure**: The combination of these functional groups and structural elements suggests that the given molecule has a balance of hydrophilic and lipophilic properties. The piperazine and carbothioamide groups provide hydrophilic characteristics, while the chloro and dimethylpyridine groups contribute to lipophilicity. This balance is often associated with moderate permeability in PAMPA assays, as it allows the molecule to interact with both the aqueous and lipid phases of the membrane.

In summary, the given molecule is likely to exhibit moderate permeability in the PAMPA assay due to its balanced hydrophilic and lipophilic properties, as well as its ability to engage in various intermolecular interactions.

Final answer: Low-to-moderate permeability.

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# 171

**SMILES:** CC1=CC=C(C=C1)S(=O)(=O)NC2=CC=CC(=C2Cl)C(=O)NC3=NC(=CS3)C4=CC=CC=C4

**Label:** 0

**Predi:** 0

**Correct:** 1

# Response:
The given molecule is a sulfonamide, which is a class of compounds known for their antimicrobial properties. The sulfonamide group is characterized by the presence of a sulfonyl functional group attached to an amine. In this molecule, the sulfonamide group is attached to a benzene ring, which is further substituted with a chlorine atom. This substitution can influence the molecule's electronic properties and potentially its interaction with biological membranes.

The molecule also contains a thiazole ring, which is a five-membered heterocyclic compound containing both sulfur and nitrogen. Thiazole rings are often found in bioactive molecules and can contribute to the molecule's ability to interact with biological targets.

The presence of a phenyl group attached to the thiazole ring can enhance the lipophilicity of the molecule, which may facilitate its passage through lipid membranes. However, the overall permeability of the molecule will also depend on the balance between its hydrophilic and lipophilic properties.

The benzamide moiety in the molecule can also play a role in its permeability. Amide groups are generally polar, which can increase the molecule's solubility in water and potentially its permeability through aqueous environments.

Considering these structural features, the given molecule is likely to exhibit moderate permeability in the PAMPA assay. The presence of both hydrophilic and lipophilic groups suggests that it may have a balanced solubility profile, allowing it to interact with both the aqueous and lipid components of the artificial membrane. However, the exact permeability would need to be experimentally determined through the PAMPA assay.

Final answer: Low-to-moderate permeability.

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# 172

**SMILES:** COC1=CC=CC(=C1O)CNC2=CC=C(C=C2)S(=O)(=O)NC3=CN=CC=C3

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a sulfonamide, which is a class of compounds known for their antibacterial properties. The sulfonamide group is characterized by the presence of a sulfonyl functional group attached to an amine. This group is known to enhance the molecule's ability to interact with biological targets, such as enzymes or receptors, due to its polar nature and ability to form hydrogen bonds.

In the given molecule, the sulfonamide group is attached to a pyridine ring, which is a nitrogen-containing heterocycle. The presence of the pyridine ring can increase the molecule's ability to interact with biological systems due to its aromatic nature and potential for hydrogen bonding and π-π interactions.

The molecule also contains a methoxy group attached to a phenyl ring. The methoxy group is an electron-donating group, which can influence the electronic properties of the phenyl ring, potentially affecting the molecule's overall polarity and solubility. This can impact the molecule's ability to permeate through biological membranes.

Additionally, the molecule has an amino group linked to a phenyl ring, which can participate in hydrogen bonding and increase the molecule's solubility in aqueous environments. This can enhance the molecule's permeability by allowing it to interact favorably with the polar environment of the artificial membrane.

Overall, the combination of these functional groups suggests that the given molecule has a balance of hydrophilic and hydrophobic properties, which can facilitate its permeability through the artificial membrane. The sulfonamide group, in particular, is likely to play a significant role in enhancing the molecule's interaction with the membrane, contributing to its permeability. Therefore, the given molecule is likely to exhibit high permeability in the Parallel Artificial Membrane Permeability Assay (PAMPA).

Final answer: High permeability

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# 173

**SMILES:** CC1=C(N(C(=C1C(=O)C)C)C)C(=O)NC2=CC(=CC=C2)[S+](=O)(N(C)C)[O-]

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a complex organic compound that features several functional groups and structural elements that influence its permeability in the PAMPA assay. Let's break down these features and their impact on permeability:

1. **Pyrrole Ring**: The core structure of the given molecule includes a pyrrole ring, which is a five-membered heterocyclic aromatic ring containing nitrogen. Pyrrole rings are relatively planar and aromatic, which can enhance the molecule's ability to interact with the artificial membrane through π-π stacking interactions. This can contribute to moderate to high permeability, depending on the overall size and lipophilicity of the molecule.

2. **Acetyl Group**: The presence of an acetyl group on the pyrrole ring introduces a polar carbonyl group. This can increase the molecule's overall polarity, potentially enhancing its solubility in aqueous environments and facilitating interactions with the polar head groups of the artificial membrane. However, the acetyl group's size and position may also introduce steric hindrance, which could limit permeability.

3. **Dimethyl Substituents**: The dimethyl groups on the pyrrole ring increase the hydrophobic character of the molecule. These groups can enhance lipophilicity, which is generally associated with higher permeability through lipid membranes. However, the balance between hydrophilic and hydrophobic properties will determine the overall permeability.

4. **Sulfamoyl Group**: The sulfamoyl group attached to the phenyl ring introduces additional polarity and potential for hydrogen bonding. This group can interact with the polar components of the artificial membrane, potentially enhancing permeability. However, the presence of a bulky sulfamoyl group may also introduce steric hindrance, which could limit permeability.

5. **Methylphenyl Group**: The methyl group on the phenyl ring increases the hydrophobic character of the molecule. This can enhance lipophilicity, which is generally associated with higher permeability. The aromatic nature of the phenyl ring can also facilitate π-π interactions with the artificial membrane.

Overall, the given molecule exhibits a balance of hydrophilic and hydrophobic properties, with aromatic and polar functional groups that can interact with the artificial membrane. The presence of both polar and non-polar groups suggests that the molecule may have moderate to high permeability, depending on the specific balance of these interactions and the size of the molecule relative to the membrane pores.

Final answer: Low-to-moderate permeability.

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# 174

**SMILES:** CCC1=C(C=C(C=C1)NC(=O)C2=C(C(=C(N2)C)C(=O)C)C)[S+](=O)(NC3=CC=C(C=C3)C#N)[O-]

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a sulfonamide, which is a class of compounds known for their antibacterial properties. In the context of the Parallel Artificial Membrane Permeability Assay (PAMPA), the permeability of the molecule is influenced by its structural features.

The molecule contains several functional groups that contribute to its permeability:

1. **Sulfonamide Group**: This group is known for its ability to form hydrogen bonds, which can enhance the molecule's solubility and permeability. The presence of the sulfonamide group suggests that the molecule may have moderate to high permeability due to its ability to interact with the artificial membrane.

2. **Aromatic Rings**: The molecule contains multiple aromatic rings, including a phenyl group and a pyrrole ring. Aromatic rings can increase lipophilicity, which may enhance membrane permeability. However, the presence of electron-withdrawing groups, such as the acetyl group on the phenyl ring, can affect the overall balance between hydrophilicity and lipophilicity.

3. **Acetyl Group**: The acetyl group on the phenyl ring introduces a polar character, which can enhance hydrogen bonding and solubility. This group may contribute to moderate permeability by balancing the lipophilic nature of the aromatic ring.

4. **Ethyl and Methyl Substituents**: These alkyl groups increase the hydrophobic character of the molecule, which can enhance membrane permeability by increasing lipophilicity. However, their presence may also lead to steric hindrance, potentially reducing permeability.

5. **Amide Linkage**: The amide linkage in the molecule can participate in hydrogen bonding, which may enhance solubility and permeability. However, the presence of the amide group can also introduce rigidity, which may affect the molecule's ability to fit into the membrane.

Overall, the given molecule's structural features suggest that it may have moderate to high permeability in the PAMPA assay. The balance between hydrophilic and lipophilic groups, along with the ability to form hydrogen bonds, supports its potential to permeate the artificial membrane.

Final answer: Low-to-moderate permeability.

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# 175

**SMILES:** COC1=CC2=C(C=C1)OC(=N2)NC3=NC(C4=C(N3)CCCC4=O)C5=C(C=NN5)Cl

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound with several distinct structural features that influence its permeability in the PAMPA assay. Let's break down these features and their implications:

1. **Quinazoline Core**: The presence of a quinazoline moiety in the given molecule suggests potential interactions with biological membranes. Quinazolines are known for their planar aromatic structure, which can facilitate stacking interactions with lipid bilayers, enhancing permeability.

2. **Chloro Substituent**: The chloro group on the quinazoline ring can influence the molecule's lipophilicity. Chlorine atoms can increase the hydrophobic character of a molecule, which may enhance its ability to permeate lipid membranes. However, the presence of a chloro group can also introduce steric hindrance, potentially affecting the molecule's overall permeability.

3. **Benzoxazole Ring**: The benzoxazole moiety contributes to the molecule's aromaticity and can participate in hydrogen bonding and π-π interactions with the artificial membrane. This can enhance the molecule's ability to permeate the membrane by stabilizing interactions with the lipid bilayer.

4. **Pyrimidinyl Group**: The pyrimidinyl group, particularly with its attached methoxy substituent, adds to the molecule's complexity. The methoxy group can increase the molecule's solubility in organic solvents, which is beneficial for permeability. Additionally, the pyrimidinyl group can engage in hydrogen bonding, which may facilitate interaction with the membrane.

5. **Tetrahydroquinazoline Structure**: The partially saturated tetrahydroquinazoline ring introduces flexibility to the molecule. This flexibility can allow the molecule to adapt its conformation to fit into the membrane, potentially enhancing permeability.

Overall, the given molecule's combination of aromatic rings, heteroatoms, and substituents suggests that it has a balance of hydrophobic and hydrophilic properties, which is often desirable for good permeability. The presence of multiple aromatic systems and functional groups capable of hydrogen bonding indicates that the molecule can effectively interact with the artificial membrane, likely resulting in high permeability.

Final answer: High permeability

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# 176

**SMILES:** CC1=C(C=C(C=C1)NC(=O)NCC2CCN(CC2)CC3=CC(=CC=C3)Cl)Cl

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several functional groups and structural elements that influence its permeability in the PAMPA assay. Let's break down the key components and their impact on permeability:

1. **Urea Linkage**: The presence of a urea group in the molecule is significant. Urea linkages are polar and can form hydrogen bonds, which generally enhance the molecule's solubility in water. This increased solubility can facilitate the molecule's interaction with the artificial membrane, potentially leading to higher permeability.

2. **Aromatic Rings**: The molecule contains two aromatic rings: a chlorophenyl group and a methylphenyl group. Aromatic rings can contribute to the molecule's lipophilicity, which is the ability to dissolve in fats, oils, and non-polar solvents. This lipophilicity can enhance the molecule's ability to permeate lipid membranes, such as the artificial membrane used in the PAMPA assay.

3. **Chlorine Substituents**: The presence of chlorine atoms on the phenyl rings can further influence the molecule's lipophilicity. Chlorine is an electronegative atom that can increase the electron density of the aromatic ring, potentially enhancing the molecule's ability to interact with the hydrophobic regions of the artificial membrane.

4. **Piperidine Ring**: The piperidine moiety is a saturated nitrogen-containing heterocycle that can contribute to the molecule's basicity. This basicity can affect the molecule's ionization state, which in turn influences its permeability. The piperidine ring can also provide a degree of flexibility to the molecule, allowing it to adapt its conformation to better fit the membrane.

5. **Methyl Group**: The methyl group attached to the phenyl ring can increase the hydrophobic character of the molecule, which may enhance its permeability through the lipid-rich artificial membrane.

Overall, the given molecule's combination of polar and non-polar characteristics, along with its ability to form hydrogen bonds and interact with lipid membranes, suggests that it would exhibit high permeability in the PAMPA assay. The balance of hydrophilic and hydrophobic properties, along with the structural flexibility provided by the piperidine ring, likely facilitates its passage through the artificial membrane.

Final answer: High permeability

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# 177

**SMILES:** CC1=CC(=C(N1C2=CC=NC=C2)C)C3=NN=C4N3CCCCC4

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex structure that includes several key features influencing its permeability in the PAMPA assay. Let's break down these features and their implications:

1. **Pyridine Ring**: The presence of a pyridine ring, which is a six-membered aromatic ring containing one nitrogen atom, contributes to the molecule's polarity and potential hydrogen bonding capabilities. This can enhance the molecule's solubility in aqueous environments, which is beneficial for permeability through the PAMPA membrane, a model for biological membranes.

2. **Dimethyl Substitution**: The dimethyl groups on the pyridine ring increase the hydrophobic character of the molecule. This can affect the balance between hydrophilicity and lipophilicity, potentially enhancing the molecule's ability to interact with the lipid components of the artificial membrane, promoting permeability.

3. **Triazolopyridazine Moiety**: This bicyclic structure, which includes a triazole ring fused to a pyridazine ring, adds complexity to the molecule. The triazole ring can participate in hydrogen bonding and π-π interactions, which may facilitate binding to the membrane. The pyridazine component can also contribute to the molecule's overall aromaticity and stability, potentially aiding in permeation.

4. **Tetrahydropyrroloazepine System**: This part of the molecule introduces a partially saturated, seven-membered ring system. The presence of nitrogen atoms in this system can enhance the molecule's ability to form hydrogen bonds and interact with the membrane. The saturation level of this ring can influence the flexibility and conformational adaptability of the molecule, which is crucial for fitting into the membrane's structure.

Overall, the given molecule's combination of aromatic rings, nitrogen heteroatoms, and hydrophobic substituents suggests that it has a balanced profile of hydrophilic and lipophilic properties. This balance is often associated with moderate to high permeability in PAMPA assays, as it allows the molecule to effectively interact with both the aqueous and lipid phases of the membrane. Therefore, the given molecule is likely to exhibit high permeability in the PAMPA assay.

Final answer: High permeability

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# 178

**SMILES:** CC[S+](=O)(NC1=CC=CC=C1C(=O)NC2=NC(=CS2)C3=CC=CC=C3)[O-]

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a benzamide derivative, which is a class of compounds known for their potential biological activity. The structure of the given molecule includes several key features that influence its permeability:

1. **Benzamide Core**: The benzamide moiety is a planar aromatic structure, which can facilitate interactions with the artificial membrane through π-π stacking and hydrophobic interactions. This can enhance the molecule's permeability.

2. **Thiazole Ring**: The presence of a thiazole ring, which is a five-membered heterocyclic compound containing both sulfur and nitrogen, can contribute to the molecule's ability to penetrate the membrane. The thiazole ring is relatively polar, which can enhance solubility and membrane permeability due to its ability to form hydrogen bonds and other polar interactions.

3. **Phenyl Group**: The phenyl group attached to the thiazole ring adds to the hydrophobic character of the molecule. This can enhance membrane permeability by allowing the molecule to interact with the lipid bilayer of the artificial membrane.

4. **Ethylsulfonylamino Group**: This group introduces a sulfonyl moiety, which is highly polar and can increase the molecule's solubility in aqueous environments. The presence of this group can also enhance the molecule's ability to form hydrogen bonds, potentially improving its interaction with the membrane.

Overall, the combination of aromatic and polar functional groups in the given molecule suggests that it would have moderate to high permeability in the PAMPA assay. The balance of hydrophobic and hydrophilic properties allows the molecule to interact effectively with the artificial membrane, facilitating its passage through the membrane.

Final answer: High permeability

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# 179

**SMILES:** C1=CC=C2C(=C1)/C(=C\C3=CC=C(C=C3)O)/C(=O)N2

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a derivative of hydroxyphenyl compounds, which are known for their ability to interact with biological membranes due to their aromatic and hydroxyl functional groups. The presence of the hydroxyphenyl group suggests that the molecule can form hydrogen bonds, which may enhance its interaction with the artificial membrane.

The indole-2-one structure in the given molecule is a bicyclic compound that is often found in biologically active molecules. This structure can contribute to the molecule's ability to permeate through lipid membranes due to its planar and aromatic nature, which allows for favorable interactions with the lipid bilayer of the artificial membrane.

The methylene bridge connecting the hydroxyphenyl group to the indole-2-one core introduces a degree of rigidity and planarity to the molecule. This structural feature can facilitate the passage of the molecule through the membrane by allowing it to maintain a relatively flat conformation, which is beneficial for permeation.

Overall, the combination of the hydroxyphenyl group, the indole-2-one core, and the methylene bridge suggests that the given molecule is likely to exhibit high permeability in the artificial membrane, as these features enhance its ability to interact with and traverse the lipid environment of the membrane.

Final answer: High permeability

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# 180

**SMILES:** C1CC2=C(C(N=C(N2)NC3=NC4=CC=CC=C4O3)C5=C(C=NN5)Cl)C(=O)C1

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a complex organic compound with several distinct structural features that influence its permeability in the PAMPA assay. Let's break down these features and their implications:

1. **Benzoxazole Moiety**: The presence of the benzoxazole group, which is a bicyclic structure containing both benzene and oxazole rings, contributes to the molecule's aromatic character. Aromatic compounds often have enhanced lipophilicity, which can facilitate membrane permeability. However, the benzoxazole's heteroatoms (oxygen and nitrogen) can also introduce polar characteristics, potentially affecting the molecule's overall solubility and permeability.

2. **Pyrimidine Ring**: The pyrimidine ring is another heterocyclic component of the given molecule. Pyrimidines are known for their ability to participate in hydrogen bonding due to the nitrogen atoms in the ring. This can influence the molecule's interaction with the artificial membrane, potentially enhancing permeability through hydrogen bonding interactions with the membrane's polar sites.

3. **Thiazole Ring**: The thiazole ring, which contains both sulfur and nitrogen, adds to the molecule's heteroaromatic nature. Thiazoles are known for their electron-rich properties, which can affect the molecule's ability to interact with the membrane. The presence of sulfur can also contribute to the molecule's lipophilicity, potentially enhancing permeability.

4. **Tetrahydroquinazolinone Core**: The tetrahydroquinazolinone structure is a partially saturated quinazoline ring, which can influence the molecule's flexibility and conformational adaptability. This flexibility can be beneficial for fitting into the membrane's structure, potentially enhancing permeability. The carbonyl group in the quinazolinone can also participate in hydrogen bonding, which may affect the molecule's interaction with the membrane.

5. **Overall Structure**: The combination of aromatic and heterocyclic rings, along with the presence of polar functional groups, suggests that the given molecule has a balance of lipophilic and hydrophilic properties. This balance is crucial for permeability, as it allows the molecule to interact with both the hydrophobic and hydrophilic components of the artificial membrane.

Considering these structural features, the given molecule is likely to exhibit moderate permeability in the PAMPA assay. The presence of multiple aromatic and heterocyclic rings suggests a degree of lipophilicity, while the polar functional groups can facilitate interactions with the membrane. This balance of properties typically results in moderate permeability, neither extremely high nor extremely low.

Final answer: Low-to-moderate permeability.

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# 181

**SMILES:** CC1=C(C=C(C=C1)C(=O)NC2=CC3=C(C=C2)OC(=N3)C4=CN=CC=C4)[N+](=O)[O-]

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound with several functional groups and structural features that influence its permeability in the PAMPA assay. Let's break down these features and their impact on permeability:

1. **Benzoxazole Ring**: The presence of a benzoxazole moiety contributes to the molecule's aromaticity and planarity. Aromatic and planar structures often enhance membrane permeability due to their ability to intercalate with lipid bilayers, facilitating passive diffusion.

2. **Pyridine Ring**: The pyridine ring is a heteroaromatic structure that can participate in hydrogen bonding and π-π interactions with the membrane. This can enhance the molecule's ability to interact with the artificial membrane, potentially increasing its permeability.

3. **Nitro Group**: The nitro group is an electron-withdrawing group that can influence the molecule's polarity and solubility. While it may decrease the overall lipophilicity of the molecule, it can also participate in specific interactions with the membrane, potentially affecting permeability.

4. **Amide Linkage**: The amide group is a polar functional group that can form hydrogen bonds with the membrane. This can enhance the molecule's solubility in aqueous environments and facilitate interactions with the membrane, potentially increasing permeability.

5. **Methyl Group**: The methyl group is a small, non-polar substituent that can increase the lipophilicity of the molecule. This can enhance membrane permeability by increasing the molecule's ability to dissolve in the lipid bilayer.

Overall, the given molecule has a combination of aromatic and polar features that suggest it may have moderate to high permeability in the PAMPA assay. The balance of hydrophilic and lipophilic groups allows it to interact favorably with the artificial membrane, facilitating its passage through the membrane.

Final answer: High permeability

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# 182

**SMILES:** CN(C1=CC=CC=C1)C(=O)CSC2=NC3=C(CCCC3)C(=O)N2

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several distinct structural components, each contributing to its permeability characteristics in the PAMPA assay.

1. **Quinazoline Core**: The molecule contains a quinazoline moiety, which is a bicyclic structure consisting of a benzene ring fused to a pyrimidine ring. This core is known for its planar aromatic structure, which can facilitate interactions with the artificial membrane through π-π stacking and hydrophobic interactions. The presence of a carbonyl group (oxo) in the quinazoline ring introduces a polar site, which can form hydrogen bonds with the membrane, potentially enhancing permeability.

2. **Thioether Linkage**: The molecule features a thioether linkage, where a sulfur atom connects the quinazoline core to the rest of the molecule. Thioethers are generally non-polar and can contribute to the lipophilicity of the molecule, enhancing its ability to traverse lipid membranes.

3. **Amide Group**: The presence of an amide group in the molecule introduces a polar site that can participate in hydrogen bonding. This functional group can interact with the polar head groups of the artificial membrane, potentially influencing permeability.

4. **Phenyl Group**: The phenyl group attached to the nitrogen atom of the amide contributes to the overall hydrophobic character of the molecule. This aromatic ring can engage in hydrophobic interactions with the membrane, aiding in permeability.

5. **N-Methyl Substitution**: The N-methyl group on the amide nitrogen increases the molecule's lipophilicity, which can enhance its ability to permeate the artificial membrane.

Overall, the given molecule's combination of aromatic, polar, and non-polar features suggests that it would exhibit high permeability in the PAMPA assay. The balance of hydrophobic and hydrophilic interactions allows it to effectively interact with the artificial membrane, facilitating its passage through the model lipid bilayer.

Final answer: High permeability

------
# 183

**SMILES:** CN1C2=C(C=CC(=C2)C(=O)NCC3=CC=C(C=C3)Br)[S@@](=O)C4=CC=CC=C4C1=O

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several functional groups and structural elements that influence its permeability in the PAMPA assay. Let's break down the key components and their impact on permeability:

1. **Benzothiazine Core**: The presence of a benzothiazine moiety, which is a bicyclic structure combining a benzene ring with a thiazine ring, contributes to the molecule's rigidity and planarity. This structural feature can enhance the molecule's ability to interact with the artificial membrane, potentially increasing its permeability. The aromatic nature of the benzene ring can facilitate π-π interactions with the membrane, which may aid in permeation.

2. **Bromo Substituent**: The bromine atom attached to the phenyl ring introduces a degree of lipophilicity to the molecule. Halogen atoms like bromine can enhance membrane permeability by increasing the molecule's ability to traverse lipid bilayers. However, the presence of a bromine atom can also introduce steric hindrance, which might affect the overall permeability depending on the orientation and spatial arrangement of the molecule.

3. **Amide Group**: The carboxamide functional group is polar and can form hydrogen bonds with the artificial membrane. This interaction can be beneficial for permeability as it allows the molecule to establish specific interactions with the membrane, potentially aiding in its passage. However, the amide group can also introduce some degree of hydrophilicity, which might limit permeability if it leads to unfavorable interactions with the membrane.

4. **Methyl Group**: The methyl group attached to the benzothiazine core adds to the hydrophobic character of the molecule. This can enhance the molecule's ability to interact with the lipid components of the artificial membrane, potentially increasing permeability.

Overall, the given molecule's structure suggests a balance between hydrophobic and hydrophilic interactions with the artificial membrane. The aromatic and halogenated components likely contribute to high permeability, while the amide group provides a degree of polarity that can facilitate specific interactions. Therefore, the given molecule is likely to exhibit high permeability in the PAMPA assay.

Final answer: High permeability

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# 184

**SMILES:** CC1=CC=C(C=C1)S(=O)(=O)NC2=C(C=CC(=C2)C(=O)NC3=NC(=CS3)C4=CC=CC=C4)OC

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a sulfonamide, which is a class of compounds known for their antibacterial properties. The sulfonamide group is characterized by the presence of a sulfonyl functional group attached to an amine. This group is known to enhance the molecule's ability to interact with biological targets, such as enzymes or receptors, due to its polar nature and ability to form hydrogen bonds.

In the given molecule, the sulfonamide group is attached to a benzamide moiety, which is a benzene ring linked to an amide group. The presence of the benzamide structure can contribute to the molecule's ability to permeate biological membranes, as it can enhance lipophilicity and facilitate interactions with lipid bilayers.

The molecule also contains a thiazole ring, which is a five-membered heterocyclic compound containing both sulfur and nitrogen. Thiazole rings are often found in bioactive molecules and can contribute to the molecule's overall stability and ability to interact with biological targets.

Additionally, the methoxy group on the phenyl ring can increase the molecule's lipophilicity, potentially enhancing its ability to permeate lipid membranes. The phenyl ring itself is a hydrophobic aromatic group that can also contribute to membrane permeability by interacting with the lipid components of the membrane.

Overall, the combination of these functional groups suggests that the given molecule may have moderate to high permeability in the PAMPA assay, as the presence of both polar and non-polar groups allows for a balance of solubility and membrane interaction. The sulfonamide group, in particular, is likely to play a significant role in the molecule's permeability, as it can facilitate interactions with the artificial membrane.

Final answer: High permeability.

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# 185

**SMILES:** C1=CC=C2C(=C1)C(=NC(=N2)C3=CC=NC=C3)NC4=CC=NN4

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a complex organic compound that features several aromatic and heterocyclic components, which are key to understanding its permeability characteristics.

The core structure of the given molecule is a quinazoline ring, which is a bicyclic compound consisting of a benzene ring fused to a pyrimidine ring. Quinazolines are known for their planar structure, which can facilitate interactions with biological membranes. The presence of this core suggests that the molecule may have a certain degree of lipophilicity, which can enhance its ability to permeate lipid membranes.

Attached to the quinazoline core is a pyridinyl group. Pyridine rings are aromatic and can contribute to the overall hydrophobic character of the molecule. This can further enhance membrane permeability by allowing the molecule to interact with the lipid bilayer of the membrane.

Additionally, the molecule contains a pyrazolyl group. Pyrazole rings are five-membered heterocycles containing two nitrogen atoms, which can introduce some degree of polarity to the molecule. This can affect the molecule's solubility and permeability, potentially increasing its ability to interact with polar sites on the membrane.

The amine group attached to the quinazoline ring can also play a role in permeability. Amines can form hydrogen bonds, which may facilitate interactions with the membrane or enhance solubility in aqueous environments.

Overall, the combination of aromatic and heterocyclic rings, along with the amine group, suggests that the given molecule has a balance of hydrophobic and polar characteristics. This balance can lead to moderate permeability in the PAMPA assay, allowing the molecule to interact with the artificial membrane but not necessarily achieving high permeability.

Final answer: Low-to-moderate permeability.

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# 186

**SMILES:** CC1=CC=C(C=C1)S(=O)(=O)NC2=C(C=CN=C2)C(=O)NC3=NC(=CS3)C4=CC=CC=C4Cl

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a sulfonamide, which is a class of compounds known for their antimicrobial properties. The sulfonamide group is characterized by the presence of a sulfonyl functional group attached to an amine. This group is known to enhance the molecule's ability to interact with biological membranes due to its polar nature, which can facilitate passage through lipid bilayers.

The structure of the given molecule includes several key features that influence its permeability:

1. **Sulfonamide Group**: The presence of the sulfonamide moiety contributes to the molecule's overall polarity, which can enhance its permeability through the artificial membrane. This group is often involved in hydrogen bonding and ionic interactions, which can aid in the molecule's transport across the membrane.

2. **Aromatic Rings**: The molecule contains multiple aromatic rings, including a phenyl ring, a pyridine ring, and a thiazole ring. These rings can contribute to the molecule's lipophilicity, which can enhance its ability to traverse lipid membranes. However, the balance between hydrophilic and lipophilic properties is crucial for permeability.

3. **Chlorine Substitution**: The presence of a chlorine atom on the phenyl ring can increase the molecule's lipophilicity, potentially enhancing its membrane permeability. Halogen atoms like chlorine can also participate in halogen bonding, which may influence the molecule's interaction with the membrane.

4. **Amide Linkage**: The amide group in the molecule can participate in hydrogen bonding, which may facilitate interaction with the membrane and improve permeability. Amide linkages are often found in bioactive molecules and can play a role in the molecule's overall stability and permeability.

Overall, the given molecule's combination of polar and non-polar features suggests that it may have moderate to high permeability in the artificial membrane. The sulfonamide group, along with the aromatic and halogenated components, likely contribute to a balance of hydrophilic and lipophilic properties that favor permeability.

Final answer: High permeability

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# 187

**SMILES:** C1=CC(=C(C=C1NC2=NC(=NC=C2)C3=CC=NC=C3)F)F

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a pyridine derivative with a difluorophenyl group and a pyridazinylamine moiety. The presence of the difluorophenyl group suggests that the molecule has increased lipophilicity due to the fluorine atoms, which can enhance membrane permeability by increasing the molecule's ability to interact with lipid bilayers. The pyridine and pyridazine rings contribute to the molecule's aromatic character, which can also facilitate passage through lipid membranes due to π-π interactions with the lipid bilayer.

The amine group attached to the pyridazine ring can form hydrogen bonds, which may aid in the molecule's interaction with the artificial membrane. However, the overall structure, with its aromatic rings and fluorine substituents, suggests that the molecule's permeability is likely higher due to its ability to traverse lipid environments effectively. Therefore, the given molecule is expected to have high permeability in the Parallel Artificial Membrane Permeability Assay (PAMPA).

Final answer: High permeability

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# 188

**SMILES:** C1CC(C2=C(C1)C3=C(N2)C(=CC=C3)Cl)NC(=O)C4=CC5=C(C=C4)OCO5

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several distinct structural components, each contributing to its permeability characteristics in the PAMPA assay.

Firstly, the molecule contains a tetrahydro-1H-carbazole moiety. This structure is a partially saturated derivative of carbazole, which is a tricyclic aromatic compound. The presence of the tetrahydro component indicates that the aromaticity is reduced, which can increase the molecule's flexibility and potentially enhance its ability to permeate through the artificial membrane. This is because the reduced aromaticity can lead to a more favorable interaction with the membrane, allowing the molecule to adopt conformations that facilitate passage through the membrane.

Additionally, the molecule has a chloro substituent on the carbazole ring. The presence of a chlorine atom can influence the molecule's lipophilicity, which is a key factor in determining permeability. Chlorine is a relatively electronegative atom, and its presence can increase the overall lipophilicity of the molecule. This can enhance the molecule's ability to interact with the lipid components of the artificial membrane, potentially increasing its permeability.

The molecule also features a benzodioxole moiety, which is a bicyclic structure consisting of a benzene ring fused with a dioxole ring. This moiety is known for its electron-rich aromatic system, which can contribute to the molecule's overall stability and ability to engage in π-π interactions with the membrane. The benzodioxole group can also enhance the molecule's lipophilicity, further promoting its permeability.

Finally, the molecule contains an amide linkage, which is a common functional group in many bioactive compounds. Amides are generally polar and can form hydrogen bonds, which may aid in the molecule's interaction with the membrane. However, the presence of the amide group can also introduce some degree of polarity, which might reduce permeability if the membrane is more polar or hydrophilic.

Overall, the structural features of the given molecule, including the tetrahydro-carbazole moiety, chloro substituent, benzodioxole group, and amide linkage, suggest that it would exhibit high permeability in the PAMPA assay. These features collectively enhance the molecule's lipophilicity and ability to interact with the artificial membrane, facilitating its passage through the membrane.

Final answer: High permeability.

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# 189

**SMILES:** COC1=CC(=CC(=C1OC)OC)NC(=O)C2=CC(=NO2)C3=CC=CC=C3O

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is characterized by several structural features that influence its permeability in the PAMPA assay. 

Firstly, the presence of the 3,4,5-trimethoxyphenyl group contributes to the molecule's lipophilicity. Methoxy groups are electron-donating and increase the hydrophobic character of the molecule, which can enhance its ability to permeate through the lipid-like environment of the artificial membrane. This increased lipophilicity often correlates with higher permeability.

Secondly, the molecule contains an isoxazole ring, which is a five-membered heterocycle containing both nitrogen and oxygen. Isoxazole rings can contribute to the molecule's overall stability and rigidity, potentially affecting its ability to interact with the membrane. The presence of heteroatoms like nitrogen and oxygen can also introduce hydrogen bonding capabilities, which may influence the molecule's interaction with the membrane and its overall permeability.

Additionally, the molecule features a hydroxyphenyl group, which introduces a polar functional group. The hydroxyl group can form hydrogen bonds with the membrane, potentially enhancing the molecule's interaction with the membrane and affecting its permeability. However, the presence of this polar group may also introduce some degree of hydrophilicity, which could counterbalance the lipophilic effects of the methoxy groups.

Overall, the combination of lipophilic methoxy groups and polar hydroxyl groups, along with the structural rigidity provided by the isoxazole ring, suggests that the given molecule may exhibit a balance of permeability characteristics. While the methoxy groups may promote high permeability through the membrane, the hydroxyl group and the isoxazole ring could introduce some degree of complexity in its interaction with the membrane, potentially leading to a moderate permeability profile.

Final answer: Low-to-moderate permeability.

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# 190

**SMILES:** CC1=CC(=NO1)NS(=O)(=O)C2=CC=C(C=C2)NCCC3=CC(=C(C=C3)Cl)Cl

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a sulfonamide, which is a class of compounds known for their potential as pharmaceuticals due to their ability to permeate biological membranes. The permeability of the given molecule can be analyzed by examining its structural features.

The molecule contains a sulfonamide group, which is known to enhance the solubility and permeability of compounds. This group can form hydrogen bonds with the artificial membrane, facilitating its passage through the membrane.

Additionally, the presence of the 3,4-dichlorophenyl group contributes to the molecule's lipophilicity, which can enhance its ability to permeate lipid membranes. The dichloro substitution on the phenyl ring can also increase the molecule's stability and resistance to metabolic degradation, potentially improving its permeability.

The ethylamino linkage provides a flexible connection between the phenyl ring and the rest of the molecule, which can help the molecule to adapt its conformation to fit through the membrane pores.

The isoxazole ring, with its heteroaromatic nature, can also contribute to the molecule's overall stability and permeability. The presence of the isoxazole ring can enhance the molecule's ability to interact with the membrane through π-π interactions or hydrogen bonding.

Overall, the combination of these structural features suggests that the given molecule likely exhibits high permeability in the Parallel Artificial Membrane Permeability Assay (PAMPA).

Final answer: High permeability

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# 191

**SMILES:** CC1=CN=C(N=C1NCC2=CC=C(C=C2)C3=CN=CC=C3)C4=CC=CC=C4C5COC5

**Label:** 0

**Predi:** 1

**Correct:** 0

# Response:
The given molecule is designed to interact with the epidermal growth factor receptor (EGFR), which is a transmembrane receptor tyrosine kinase. The molecule's structure includes several key features that influence its permeability and activity as an antineoplastic agent.

1. **Pyrimidine Core**: The presence of a pyrimidine ring is crucial for the molecule's ability to interact with the ATP-binding site of EGFR. This heterocyclic structure is often involved in forming hydrogen bonds and π-π interactions with the target protein, enhancing the molecule's binding affinity and specificity.

2. **Aromatic Systems**: The molecule contains multiple aromatic rings, including a pyridine and a phenyl group. These rings contribute to the molecule's lipophilicity, which can enhance its ability to traverse lipid membranes. The aromatic systems also facilitate stacking interactions with the aromatic residues in the EGFR binding site, further stabilizing the molecule's binding.

3. **Methyl Substitution**: The methyl group on the pyrimidine ring can influence the molecule's electronic properties and steric profile. This substitution may affect the molecule's overall shape and how it fits into the EGFR binding pocket, potentially enhancing its selectivity and potency.

4. **Oxetane Ring**: The oxetane moiety is a four-membered ether ring that can increase the molecule's metabolic stability and oral bioavailability. The strained nature of the oxetane ring can also influence the molecule's conformational flexibility, which may be important for its interaction with EGFR.

5. **Amine Linkage**: The amine group connecting the pyridine and phenyl rings can participate in hydrogen bonding, which is essential for the molecule's binding to EGFR. This linkage also contributes to the molecule's overall polarity and solubility, which can affect its permeability.

The combination of these structural features allows the given molecule to effectively permeate the artificial membrane, as indicated by its classification as having high permeability. This permeability is essential for the molecule's oral bioavailability and its ability to reach its target site, EGFR, in the body. The molecule's high permeability, along with its structural features, supports its role as an effective antineoplastic agent by facilitating its interaction with and inhibition of EGFR.

Final answer: High permeability

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# 192

**SMILES:** CC1=C(C=C(C=C1)NC2=NC(=NC3=CC=CC=C32)C4=CC=NC=C4)F

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a quinazoline derivative, which is a class of compounds known for their biological activity, often used in pharmaceuticals. The molecule's structure includes a quinazoline core, which is a bicyclic compound consisting of a benzene ring fused to a pyrimidine ring. This core is known for its planar structure, which can facilitate interactions with biological targets.

The molecule also features a pyridinyl group attached to the quinazoline core. Pyridine rings are aromatic and can enhance the molecule's ability to participate in π-π stacking interactions, which are important for binding to biological targets such as enzymes or receptors.

Additionally, the molecule contains a substituted phenyl ring with a fluoro and a methyl group. The presence of the fluoro group can increase the molecule's lipophilicity, which may enhance its ability to permeate lipid membranes. Fluorine atoms can also influence the electronic properties of the molecule, potentially affecting its binding affinity and selectivity.

The amine group attached to the quinazoline core can form hydrogen bonds, which are crucial for the molecule's interaction with biological targets. This functional group can also contribute to the molecule's solubility and permeability.

Overall, the combination of the quinazoline core, pyridinyl group, and the substituted phenyl ring with a fluoro and a methyl group suggests that the given molecule has a balanced profile of hydrophobic and hydrophilic properties. This balance can facilitate its passage through lipid membranes, indicating that the molecule likely exhibits high permeability in the Parallel Artificial Membrane Permeability Assay (PAMPA).

Final answer: High permeability

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# 193

**SMILES:** CC1=CC=CC=C1C(=O)N2CCC(CC2)C(=O)N3CCC(CC3)N4CC5=CC=CC=C5C4=O

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a complex organic compound that can be analyzed for its permeability in the PAMPA assay. This assay is commonly used to predict the permeability of a molecule across biological membranes, which is crucial for drug development as it affects the bioavailability of the compound.

The structure of the given molecule includes several key features that influence its permeability:

1. **Piperidine Rings**: The molecule contains two piperidine rings. Piperidine is a six-membered ring containing one nitrogen atom, which can contribute to the molecule's basicity and hydrophilicity. The presence of these rings suggests that the molecule may have moderate permeability, as piperidine-containing compounds often exhibit good membrane permeability due to their ability to form hydrogen bonds and interact with lipid bilayers.

2. **Carbonyl Groups**: The molecule has multiple carbonyl groups (C=O), specifically in the form of carbonyl linkages to piperidine rings. Carbonyl groups can enhance the molecule's ability to form hydrogen bonds, which may improve its interaction with the artificial membrane. However, they can also increase the molecule's polarity, potentially reducing its permeability.

3. **Isoindole Moiety**: The isoindole structure in the molecule is a bicyclic compound that can contribute to the rigidity and planarity of the molecule. This rigidity can affect the molecule's ability to fit into the membrane pores, potentially reducing its permeability. However, the presence of the isoindole moiety may also enhance the molecule's ability to interact with specific biological targets.

4. **Methyl Substituent**: The methyl group attached to the isoindole moiety can increase the lipophilicity of the molecule, which may enhance its permeability by increasing its ability to dissolve in the lipid components of the membrane.

Overall, the given molecule's structure suggests that it may have moderate permeability in the PAMPA assay. The presence of piperidine rings and carbonyl groups indicates potential for hydrogen bonding and interaction with the membrane, while the isoindole moiety and methyl substituent contribute to the molecule's lipophilicity and rigidity. These factors collectively influence the molecule's ability to permeate the artificial membrane, resulting in a predicted moderate permeability.

Final answer: Low-to-moderate permeability.

------
# 194

**SMILES:** COC1=CC(=CC(=C1OC)OC)C(=O)NC2CCCC3=C2NC4=CC=CC=C34

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a derivative of carbazole, which is a tricyclic aromatic compound. The presence of the carbazole moiety suggests that the molecule has a rigid, planar structure, which can facilitate interactions with the artificial membrane. This structural feature is often associated with good permeability due to the ability of the aromatic rings to stack and interact with the membrane.

The molecule also contains a trimethoxybenzamide group. The methoxy groups are electron-donating, which can increase the lipophilicity of the molecule. This increased lipophilicity can enhance the molecule's ability to permeate through the lipid-rich environment of the artificial membrane.

Additionally, the amide linkage in the molecule can form hydrogen bonds with the membrane, potentially aiding in its permeation. However, the presence of the amide group also introduces some polarity, which might limit the permeability to some extent by reducing the overall lipophilicity.

Overall, the combination of the carbazole core, the trimethoxybenzamide group, and the amide linkage suggests that the given molecule likely has high permeability to the artificial membrane due to its balance of lipophilicity and potential for hydrogen bonding interactions.

Final answer: High permeability.

------
# 195

**SMILES:** COC1=CC=CC=C1NC2=NC(=NC=C2)N3CCN(CC3)C(=O)C4=CC=C(C=C4)F

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several functional groups and structural motifs that influence its permeability in the PAMPA assay. Let's break down the key structural elements and their impact on permeability:

1. **Fluorophenyl Group**: The presence of a fluorine atom on the phenyl ring can enhance the lipophilicity of the molecule. Fluorine is a small, highly electronegative atom that can increase the molecule's ability to interact with lipid membranes, potentially improving its permeability.

2. **Methanone Linkage**: The methanone group (a carbonyl group) is a polar functional group that can form hydrogen bonds with the artificial membrane. This can facilitate interactions with the membrane, potentially enhancing permeability.

3. **Pyrimidinyl Group**: The pyrimidine ring is a heterocyclic aromatic compound that can contribute to the molecule's overall planarity and rigidity. This structural feature can affect how the molecule fits into the membrane, potentially influencing its permeability.

4. **Piperazine Ring**: The piperazine moiety is a flexible, nitrogen-containing heterocycle that can enhance the solubility of the molecule in aqueous environments. This can be beneficial for permeability, as it allows the molecule to interact with the polar head groups of the artificial membrane.

5. **Methoxyanilino Group**: The methoxy group attached to the aniline moiety can increase the lipophilicity of the molecule, similar to the fluorophenyl group. This can enhance the molecule's ability to traverse the lipid-rich regions of the artificial membrane.

Overall, the given molecule contains a combination of lipophilic and polar functional groups that suggest it may have moderate to high permeability in the PAMPA assay. The balance of these groups allows the molecule to interact effectively with both the lipid and polar components of the artificial membrane, facilitating its passage through the membrane.

Final answer: High permeability

------
# 196

**SMILES:** COC1=CC=C(C=C1)C2=NC3=C(N2)C=CC=N3

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a member of the imidazopyridine class, which is characterized by a fused bicyclic structure consisting of an imidazole ring and a pyridine ring. This structural feature is significant in determining the molecule's permeability.

The imidazopyridine core contributes to the molecule's ability to interact with biological membranes due to its planar and aromatic nature. The presence of the pyridine ring can enhance the molecule's ability to participate in hydrogen bonding and π-π interactions, which are important for membrane permeability.

Additionally, the molecule has a methoxyphenyl group attached to it. The methoxy group is an electron-donating substituent, which can increase the lipophilicity of the molecule. This increased lipophilicity can enhance the molecule's ability to permeate lipid membranes, as it can more easily dissolve in the lipid bilayer.

Overall, the combination of the imidazopyridine core and the methoxyphenyl group suggests that the given molecule would have high permeability to the artificial membrane, as it is likely to interact favorably with the lipid components of the membrane.

Final answer: High permeability

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# 197

**SMILES:** CC1=CC(=NC=C1)NC(=S)N2CCCC(C2)NC3=CC=CC(=C3)C(F)(F)F

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several functional groups and structural elements that influence its permeability in the PAMPA assay. Let's break down these features and their impact on permeability:

1. **Piperidine Ring**: The presence of a piperidine ring, a six-membered nitrogen-containing heterocycle, contributes to the molecule's basicity and hydrophilicity. Piperidine rings are often found in bioactive compounds and can enhance the molecule's ability to interact with biological membranes. This ring can increase the molecule's permeability by providing a balance between hydrophilic and lipophilic properties.

2. **Thiocarbocarbamide Group**: The thiocarbocarbamide moiety introduces a sulfur atom, which can enhance the molecule's lipophilicity. Sulfur-containing groups can improve membrane permeability by increasing the molecule's ability to dissolve in lipid bilayers. However, the presence of sulfur can also introduce potential hydrogen bonding interactions, which may affect permeability depending on the environment.

3. **Pyridine Ring**: The pyridine ring, a six-membered nitrogen-containing aromatic ring, contributes to the molecule's aromaticity and basicity. Pyridine rings are known to enhance the molecule's ability to interact with biological targets through π-π stacking and hydrogen bonding. The presence of a pyridine ring can also increase the molecule's solubility in water, which may positively influence permeability.

4. **Trifluoromethyl Group**: The trifluoromethyl group is a highly electronegative substituent that can significantly alter the molecule's lipophilicity and electronic properties. This group can enhance the molecule's ability to penetrate lipid membranes by increasing its hydrophobic character. However, it can also reduce water solubility, which might decrease permeability in aqueous environments.

5. **Methylpyridine Substituent**: The methyl group attached to the pyridine ring can increase the molecule's lipophilicity, which may enhance membrane permeability. The presence of this group can also influence the electronic distribution within the molecule, potentially affecting its interaction with the artificial membrane.

Overall, the given molecule's structural features suggest a balance between hydrophilic and lipophilic properties, which is typical for molecules with moderate to high permeability in PAMPA assays. The combination of aromatic rings, basic nitrogen atoms, and lipophilic substituents likely contributes to its ability to traverse the artificial membrane, indicating a high permeability.

Final answer: High permeability

------
# 198

**SMILES:** COC1=CC=CC(=C1OC)CNC2=CC=C(C=C2)S(=O)(=O)NC3=NC=CS3

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a sulfonamide, which is a class of compounds known for their antibacterial properties. The sulfonamide group is characterized by the presence of a sulfonyl functional group attached to an amine. This group is known to enhance the molecule's ability to interact with biological targets, such as enzymes or receptors, due to its polar nature and ability to form hydrogen bonds.

The molecule also contains a thiazole ring, which is a five-membered ring containing both sulfur and nitrogen. This heterocyclic structure can contribute to the molecule's overall stability and ability to participate in various non-covalent interactions, such as hydrogen bonding and π-π stacking, which can enhance its binding affinity to biological targets.

The presence of the dimethoxyphenyl group indicates that the molecule has two methoxy groups attached to a phenyl ring. These methoxy groups are electron-donating, which can increase the electron density of the phenyl ring, potentially enhancing the molecule's ability to interact with electron-deficient sites on biological targets.

The molecule's overall structure suggests that it has a balance of hydrophilic and lipophilic properties. The sulfonamide group and thiazole ring contribute to its hydrophilicity, while the dimethoxyphenyl group adds some lipophilic character. This balance is crucial for the molecule's permeability, as it needs to be able to traverse biological membranes, which are typically lipophilic.

In the context of the Parallel Artificial Membrane Permeability Assay (PAMPA), the given molecule's structure suggests that it would exhibit moderate permeability. The sulfonamide group and thiazole ring may facilitate some degree of permeability due to their polar nature, but the dimethoxyphenyl group could limit this permeability by introducing some lipophilic characteristics. Therefore, the given molecule is likely to have low-to-moderate permeability in the PAMPA assay.

Final answer: Low-to-moderate permeability.

------
# 199

**SMILES:** C1=CC(=CC=C1NCC2=C(C=CC(=C2)Cl)O)S(=O)(=O)NC3=NC=CS3

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a sulfonamide, which is a class of compounds known for their antibacterial properties. The sulfonamide group is characterized by the presence of a sulfonyl functional group attached to an amine. This group is known to enhance the molecule's ability to interact with biological targets, such as enzymes or receptors, due to its polar nature and ability to form hydrogen bonds.

The structure of the given molecule includes several key features that influence its permeability:

1. **Sulfonamide Group**: The presence of the sulfonamide group contributes to the molecule's polarity, which can affect its permeability. This group can form hydrogen bonds with the artificial membrane, potentially increasing the molecule's interaction with the membrane and enhancing its permeability.

2. **Aromatic Rings**: The molecule contains multiple aromatic rings, including a phenyl ring and a thiazole ring. Aromatic rings can increase the lipophilicity of the molecule, which may facilitate its passage through the lipid bilayer of the artificial membrane. However, the balance between hydrophilicity and lipophilicity is crucial, and the presence of polar groups, such as the sulfonamide, can moderate this effect.

3. **Hydroxyl Group**: The hydroxyl group attached to the phenyl ring can form hydrogen bonds, which may enhance the molecule's interaction with the membrane. This group can also increase the molecule's solubility in aqueous environments, which is important for its transport across the membrane.

4. **Thiazole Ring**: The thiazole ring is a heterocyclic compound that can contribute to the molecule's overall stability and binding affinity. The presence of nitrogen and sulfur in the thiazole ring can participate in additional interactions with the membrane, potentially affecting permeability.

Overall, the given molecule's combination of polar and non-polar groups suggests that it may have moderate permeability in the PAMPA assay. The sulfonamide group and hydroxyl group contribute to its ability to interact with the membrane, while the aromatic rings and thiazole ring may enhance its lipophilicity, balancing its permeability characteristics.

Final answer: Low-to-moderate permeability.

------
# 200

**SMILES:** CN1CCN(CC1)C2=C(C=C(C=C2)NC3=NC(=NC4=CC=CC=C43)C5=CC=NC=C5)OC

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several functional groups and aromatic systems, which contribute to its permeability characteristics in the PAMPA assay.

1. **Aromatic Systems**: The molecule contains multiple aromatic rings, including a quinazoline core, a pyridine ring, and a piperazine ring. Aromatic systems are generally planar and can facilitate interactions with the artificial membrane through π-π stacking and van der Waals forces. These interactions can enhance the molecule's ability to permeate the membrane.

2. **Methoxy Group**: The presence of a methoxy group attached to the pyridine ring introduces an electron-donating effect, which can increase the lipophilicity of the molecule. This increased lipophilicity can enhance the molecule's ability to traverse the lipid-rich environment of the artificial membrane.

3. **Piperazine Ring**: The piperazine moiety is a flexible, nitrogen-containing heterocycle that can enhance the solubility of the molecule in aqueous environments. This balance of solubility and lipophilicity is crucial for permeability, as it allows the molecule to interact with both the aqueous and lipid phases of the membrane.

4. **Amine Groups**: The quinazoline core is substituted with amine groups, which can form hydrogen bonds with the artificial membrane. These interactions can stabilize the molecule's orientation and facilitate its passage through the membrane.

Overall, the combination of aromatic systems, methoxy and amine groups, and the piperazine ring suggests that the given molecule has a balance of hydrophilic and lipophilic properties, which is conducive to high permeability in the PAMPA assay. The molecule's ability to engage in various non-covalent interactions with the artificial membrane supports its potential for efficient permeation.

Final answer: High permeability

------
# 201

**SMILES:** CC1=CC=CC=C1C(=O)N2CCC3=C2C=CC(=C3)N4C=C(C=N4)NC(=O)CC5=CC=CC=C5

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a complex organic compound that includes several distinct structural features, each contributing to its permeability characteristics in the PAMPA assay.

1. **Indazole Ring System**: The presence of the indazole moiety, which is a bicyclic structure consisting of a benzene ring fused to a pyrazole ring, is significant. Indazole rings are known for their planar structure, which can facilitate interactions with the artificial membrane. The aromatic nature of the indazole can also enhance lipophilicity, potentially increasing the molecule's ability to permeate the membrane.

2. **Phenyl Groups**: The molecule contains multiple phenyl groups, which are aromatic rings. These groups contribute to the overall hydrophobic character of the molecule, enhancing its ability to interact with the lipid components of the artificial membrane. The presence of phenyl groups can also increase the molecule's ability to engage in π-π stacking interactions with the membrane.

3. **Amide Linkages**: The molecule features amide linkages, which are polar and can form hydrogen bonds. These linkages may facilitate interactions with the polar head groups of the artificial membrane, potentially aiding in permeability. However, the presence of amide bonds can also introduce some degree of rigidity and steric hindrance, which might limit the molecule's flexibility and permeability.

4. **Methyl Substituents**: The methyl group attached to the phenyl ring introduces a slight increase in hydrophobicity and steric bulk. This can influence the molecule's overall shape and how it fits into the membrane, potentially affecting its permeability.

Overall, the given molecule's structure suggests that it has a balance of hydrophobic and polar characteristics, which is typical for molecules with moderate permeability in PAMPA assays. The aromatic rings and indazole core contribute to its lipophilicity, while the amide linkages provide some polar interaction potential. This combination of features likely results in moderate permeability, allowing the molecule to traverse the artificial membrane but not excessively so.

Final answer: Low-to-moderate permeability.

------
# 202

**SMILES:** CC1=C(C=CC=N1)C(=O)NC2=CC(=C(C=C2)OC)[S+](=O)(NC3=CC=C(C=C3)Br)[O-]

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is an aromatic amide, which suggests that it contains an amide functional group attached to an aromatic ring. This structural feature is significant in determining the molecule's permeability.

The presence of the aromatic amide group indicates that the molecule has a planar structure, which can facilitate interactions with the artificial membrane. Aromatic rings are known for their ability to participate in π-π interactions, which can enhance the molecule's ability to permeate through the membrane.

The molecule also contains a methoxy group attached to one of the aromatic rings. This group can increase the molecule's lipophilicity, which is the ability to dissolve in fats, oils, and non-polar solvents. Increased lipophilicity generally enhances membrane permeability as it allows the molecule to more easily pass through the lipid bilayer of the artificial membrane.

Additionally, the molecule has a sulfonyl group attached to a phenyl ring. This group is polar and can form hydrogen bonds with the membrane, potentially aiding in the molecule's permeation by interacting with polar sites on the membrane.

The presence of a bromine atom on the phenyl ring can also influence permeability. Bromine is a relatively large atom, and its presence can affect the molecule's overall shape and electronic distribution. This can impact how the molecule interacts with the membrane, potentially enhancing or reducing permeability depending on the specific interactions.

Overall, the combination of aromatic rings, methoxy, sulfonyl, and bromine groups in the given molecule suggests that it may have moderate to high permeability in the artificial membrane, as these features collectively enhance its ability to interact with and pass through the membrane.

Final answer: High permeability

------
# 203

**SMILES:** CCC(CC)C1=NC(=NC(=C1)[C@H]2CN3CC[C@H]2C[C@@H]3CNC(=O)C)C4=CC=NC=C4

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a complex organic compound with several distinct structural features that influence its permeability in the PAMPA assay. Let's break down these features and their implications:

1. **Azabicyclo[2.2.2]octane Core**: This bicyclic structure is a rigid, three-dimensional framework that can enhance the molecule's stability and influence its interaction with the artificial membrane. The presence of nitrogen in the azabicyclo structure can also contribute to hydrogen bonding and ionic interactions, which may affect permeability.

2. **Pyridinyl and Pyrimidinyl Groups**: The pyridinyl and pyrimidinyl moieties are aromatic heterocycles that can participate in π-π stacking interactions with the membrane. These groups can also enhance the molecule's lipophilicity, which is crucial for permeability as it allows the molecule to interact with the lipid components of the membrane.

3. **Butan-2-yl Side Chain**: This alkyl side chain contributes to the hydrophobic character of the molecule, which can enhance its ability to traverse lipid membranes. The branching of the butan-2-yl group may also affect the molecule's overall shape and how it fits into the membrane.

4. **Acetamide Group**: The acetamide group introduces a polar functional group that can form hydrogen bonds with the membrane or surrounding environment. This group can also influence the solubility of the molecule, which is important for its permeability.

Overall, the given molecule's combination of hydrophobic and hydrophilic features, along with its rigid bicyclic structure, suggests that it may have moderate permeability in the PAMPA assay. The balance of lipophilic and polar groups allows it to interact with the artificial membrane, but the presence of multiple functional groups may also introduce some steric hindrance, potentially limiting its permeability compared to simpler molecules.

Final answer: Low-to-moderate permeability.

------
# 204

**SMILES:** C1CCC(C(C1)C2C3=C(CCCC3=O)NC(=N2)NC4NC5CCCCC5S4)Cl

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a complex structure that includes several distinct components contributing to its permeability characteristics. Let's break down the structural features and their implications for permeability:

1. **Cyclohexyl Group**: The presence of a cyclohexyl group, which is a non-polar, hydrophobic moiety, can enhance the molecule's lipophilicity. This hydrophobic character often facilitates the passage through lipid membranes, suggesting that the given molecule might have a favorable interaction with the lipid components of the artificial membrane.

2. **Tetrahydro-1,3-thiazine Ring**: This heterocyclic component contains both sulfur and nitrogen atoms, which can introduce polar characteristics. The presence of these heteroatoms can form hydrogen bonds or ionic interactions with the artificial membrane, potentially enhancing permeability. However, the overall effect will depend on the balance between hydrophobic and hydrophilic interactions.

3. **Tetrahydro-1,3-thiazolopyrimidinone Core**: This bicyclic structure includes both nitrogen and sulfur, contributing to the molecule's ability to engage in polar interactions. The pyrimidinone moiety can participate in hydrogen bonding, which may facilitate interaction with the polar head groups of the artificial membrane.

4. **Chlorine Substitution**: The chlorine atom introduces additional polarity and can participate in halogen bonding. This can enhance the molecule's interaction with the polar regions of the artificial membrane, potentially increasing permeability.

5. **Overall Structure**: The combination of hydrophobic and hydrophilic elements suggests that the given molecule has a balanced amphipathic nature. This balance is often associated with moderate permeability, as the molecule can interact with both the lipid and polar regions of the artificial membrane.

In summary, the given molecule's structural features suggest that it has a balanced amphipathic nature, which is likely to result in moderate permeability through the artificial membrane. The presence of both hydrophobic and hydrophilic groups allows it to interact with various components of the membrane, facilitating its passage.

Final answer: Low-to-moderate permeability.

------
# 205

**SMILES:** CC1=CC=C(C=C1)S(=O)(=O)C2=CN=C(NC2=O)SC(C)C(=O)NC3=CC=CC=C3

**Label:** 0

**Predi:** 0

**Correct:** 1

# Response:
The given molecule is a sulfonamide, which is a class of compounds known for their antimicrobial properties. The sulfonamide group is characterized by the presence of a sulfonyl functional group attached to an amine. In this molecule, the sulfonamide moiety is linked to a phenyl group and a pyrimidinyl group, which is a heterocyclic aromatic compound containing nitrogen atoms.

The presence of the sulfonamide group suggests that the given molecule may have moderate permeability in the PAMPA assay. Sulfonamides are generally polar due to the sulfonyl group, which can form hydrogen bonds with the artificial membrane. This polarity can facilitate interactions with the membrane, potentially allowing the molecule to permeate to some extent.

Additionally, the pyrimidinyl group, which contains nitrogen atoms, can also participate in hydrogen bonding and other polar interactions, further influencing the permeability. However, the overall size and complexity of the molecule, including the bulky phenyl and pyrimidinyl groups, may limit its permeability by creating steric hindrance and reducing the ability to fit through the membrane pores.

The presence of the thioether linkage (sulfanyl group) in the molecule may also impact its permeability. Thioethers can contribute to the lipophilicity of the molecule, which might enhance its ability to permeate the membrane, but this effect is balanced by the polar nature of the sulfonamide group.

In summary, while the given molecule has polar groups that can interact with the artificial membrane, its size and structural complexity suggest that it may have low-to-moderate permeability in the PAMPA assay.

Final answer: Low-to-moderate permeability.

------
# 206

**SMILES:** CC1=CC=CC=C1C(=O)NC2=NC3=C(S2)CC(CC3)C(C)(C)C

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a benzothiazole derivative, which is a class of compounds known for their diverse biological activities. The benzothiazole core is a bicyclic structure consisting of a benzene ring fused to a thiazole ring. This core is known for its stability and ability to interact with various biological targets.

The molecule also contains a tert-butyl group attached to the benzothiazole ring. The presence of this bulky hydrophobic group can enhance the molecule's lipophilicity, which often correlates with increased membrane permeability. Lipophilic molecules tend to have better permeability through lipid membranes due to their ability to dissolve in the lipid bilayer.

Additionally, the molecule features a 2-methylbenzamide moiety. The amide linkage in this moiety can form hydrogen bonds, which may influence the molecule's interaction with the artificial membrane. The methyl group on the benzene ring can also contribute to the overall hydrophobic character of the molecule, potentially enhancing its permeability.

Overall, the combination of the benzothiazole core, the tert-butyl group, and the 2-methylbenzamide moiety suggests that the given molecule likely exhibits high permeability through the artificial membrane due to its lipophilic nature and potential for hydrogen bonding interactions.

Final answer: High permeability.

------
# 207

**SMILES:** C1=CN(C(=C1)C=C2C(=O)NC(=S)NC2=O)C3=CC=C(C=C3)O

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a complex organic compound that features several functional groups and structural motifs that influence its permeability in the PAMPA assay. Let's break down the key structural elements and their impact on permeability:

1. **Hydroxyphenyl Group**: The presence of a hydroxyphenyl group introduces a polar hydroxyl group attached to a phenyl ring. This group can form hydrogen bonds with the artificial membrane, potentially increasing the molecule's interaction with the membrane and enhancing its permeability. However, the overall effect will depend on the balance between the hydrophilic nature of the hydroxyl group and the lipophilic character of the phenyl ring.

2. **Pyrrole Ring**: The pyrrole ring is a five-membered heterocyclic aromatic ring containing nitrogen. This ring can contribute to the molecule's overall aromaticity and planarity, which may facilitate its passage through the membrane by allowing it to interact with the lipid bilayer more effectively. The presence of the pyrrole ring can also influence the electronic distribution within the molecule, potentially affecting its interaction with the membrane.

3. **Diazinane-dione Core**: The diazinane-dione structure is a six-membered ring containing two carbonyl groups. This part of the molecule is relatively polar due to the carbonyl groups, which can engage in hydrogen bonding and dipole-dipole interactions with the membrane. The presence of these carbonyl groups can also increase the molecule's solubility in polar environments, which might enhance its permeability.

4. **Sulfanylidene Group**: The sulfanylidene group introduces a sulfur atom double-bonded to a carbon, which can contribute to the molecule's overall electronic properties. This group can also participate in weak interactions with the membrane, potentially affecting the molecule's permeability.

Overall, the given molecule contains a combination of polar and non-polar regions, aromatic rings, and functional groups capable of forming various interactions with the artificial membrane. These features suggest that the molecule may exhibit moderate permeability, as it has both hydrophilic and hydrophobic characteristics that can facilitate its passage through the membrane. However, the exact permeability will depend on the specific nature of the interactions between the molecule and the artificial membrane in the PAMPA assay.

Final answer: Low-to-moderate permeability.

------
# 208

**SMILES:** C1COCCN1C2=NC=NC3=C2C=CC(=C3)NC(=O)C4=CC(=CC=C4)Br

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a quinazoline derivative, which is a class of compounds known for their biological activity, particularly in the realm of pharmaceuticals. The molecule's structure includes several key features that influence its permeability.

Firstly, the quinazoline core is a bicyclic aromatic system, which contributes to the molecule's planarity and rigidity. This planar structure can facilitate interactions with biological membranes, potentially enhancing permeability. However, the presence of additional functional groups and substituents can either promote or hinder permeability.

The molecule contains a bromine atom attached to the benzamide moiety. Bromine is a relatively large and polarizable atom, which can increase the molecule's overall lipophilicity. This increased lipophilicity can enhance the molecule's ability to traverse lipid membranes, suggesting high permeability.

Additionally, the molecule has a morpholine ring, which is a heterocyclic amine. The presence of the morpholine ring introduces a degree of polarity and hydrogen bonding capability, which can influence the molecule's solubility and permeability. While the morpholine ring can enhance solubility in aqueous environments, it may also facilitate interactions with the artificial membrane, potentially contributing to moderate permeability.

The amide linkage in the benzamide portion of the molecule can also play a role in permeability. Amides are generally polar and can form hydrogen bonds, which may affect the molecule's interaction with the membrane.

Overall, the combination of the quinazoline core, the bromine substituent, and the morpholine ring suggests that the given molecule likely exhibits high permeability in the PAMPA assay, as these structural features collectively enhance lipophilicity and facilitate interactions with the artificial membrane.

Final answer: High permeability.

------
# 209

**SMILES:** C1=CC=C(C(=C1)C2=NC=C(C(=N2)NCC3=CC=C(C=C3)C4=CC=NN4)F)C(F)F

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound with several functional groups and aromatic rings that influence its permeability in the PAMPA assay. Let's break down the structural features and their impact on permeability:

1. **Aromatic Rings**: The molecule contains multiple aromatic rings, including a pyrimidine, pyrazole, and phenyl ring. Aromatic rings generally contribute to lipophilicity, which can enhance membrane permeability. However, the presence of these rings also means the molecule has a relatively rigid structure, which can affect its ability to fit into the membrane pores.

2. **Fluorine Substitution**: The presence of a fluorine atom on the pyrimidine ring can increase the molecule's lipophilicity and metabolic stability. Fluorine is a small, highly electronegative atom that can enhance the molecule's ability to penetrate lipid membranes.

3. **Trifluoromethyl Group**: The trifluoromethyl group on the pyrazole ring is another lipophilic moiety that can increase the molecule's overall hydrophobicity. This group is known to enhance membrane permeability due to its ability to interact with lipid bilayers.

4. **Amine Group**: The amine group attached to the phenyl ring can form hydrogen bonds with the membrane, potentially aiding in permeability. However, it can also introduce some degree of polarity, which might hinder permeability depending on the balance with the lipophilic groups.

5. **Pyrazole Ring**: The pyrazole ring is a heterocyclic aromatic compound that can contribute to the molecule's overall stability and rigidity. This can affect how the molecule interacts with the membrane, potentially enhancing permeability due to its planar structure.

Overall, the given molecule has a balance of lipophilic and polar features that suggest it may have moderate to high permeability in the PAMPA assay. The combination of aromatic rings, fluorine, and trifluoromethyl groups likely enhances its ability to interact with the lipid components of the artificial membrane, while the amine group may facilitate interactions with the membrane's polar head groups.

Final answer: High permeability

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# 210

**SMILES:** CC1=C(C=CN=C1)C2=NC3=CC=CC=C3C(=N2)NC4=CC(=C(C=C4)F)F

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a quinazoline derivative, which is a class of compounds known for their biological activity, often used in pharmaceuticals. The molecule's structure includes a quinazoline core, which is a bicyclic compound consisting of a benzene ring fused to a pyrimidine ring. This core is known for its ability to interact with various biological targets, contributing to the molecule's potential as a drug candidate.

The presence of a pyridine ring attached to the quinazoline core can enhance the molecule's ability to form hydrogen bonds and π-π interactions, which are important for binding to biological targets. The pyridine ring can also increase the molecule's solubility and overall stability.

The molecule also features a difluorophenyl group, which introduces fluorine atoms into the structure. Fluorine atoms can significantly affect the molecule's lipophilicity and electronic properties. The presence of fluorine can increase the molecule's metabolic stability and membrane permeability, as fluorine is highly electronegative and can form strong hydrogen bonds with biological targets.

The amine group attached to the quinazoline core can act as a hydrogen bond donor, which is crucial for the molecule's interaction with biological receptors or enzymes. This functional group can enhance the molecule's ability to permeate biological membranes by forming hydrogen bonds with the lipid bilayer.

Overall, the combination of the quinazoline core, pyridine ring, difluorophenyl group, and amine group suggests that the given molecule has a favorable balance of hydrophilic and lipophilic properties, which is likely to result in high permeability through the artificial membrane in the PAMPA assay. This permeability is essential for the molecule's potential as a drug, as it needs to efficiently reach its target site within the body.

Final answer: High permeability

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# 211

**SMILES:** CN(C)C1=CC=CC=C1C2=CSC(=N2)N3CCC(CC3)C(=O)N

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a piperidinecarboxamide, which indicates that it contains a piperidine ring attached to a carboxamide group. This structural feature is often associated with a degree of flexibility and solubility, which can influence the molecule's permeability.

The molecule also contains a thiazole ring, which is a five-membered heterocyclic compound containing both sulfur and nitrogen. Thiazole rings are known for their ability to participate in hydrogen bonding and π-π interactions, which can affect the molecule's interaction with the artificial membrane.

Additionally, the presence of a dimethylamino group attached to a phenyl ring introduces a basic site, which can enhance the molecule's solubility in aqueous environments and potentially improve its permeability through the membrane by increasing its interaction with the polar head groups of the artificial membrane.

Overall, the combination of these functional groups suggests that the given molecule may exhibit moderate permeability due to the balance of hydrophilic and hydrophobic interactions, as well as the potential for hydrogen bonding and π-π interactions with the artificial membrane.

Final answer: Low-to-moderate permeability.

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# 212

**SMILES:** CC1=CC=C(C=C1)NC(=O)C2=C3NC(=C(C(N3N=C2)C4=CC=CC=C4C)C(=O)NC5=CC=C(C=C5)Cl)C

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several functional groups and structural elements that influence its permeability in the PAMPA assay. Let's break down the key structural components and their impact on permeability:

1. **Pyrazolo[1,5-a]pyrimidine Core**: This bicyclic structure is a fused ring system that combines a pyrazole and a pyrimidine. Such heterocyclic systems are often involved in biological activity and can interact with biological membranes. The presence of nitrogen atoms in the rings can form hydrogen bonds, which may enhance interactions with the membrane.

2. **Methyl Substituents**: The given molecule has methyl groups attached to the pyrazolo[1,5-a]pyrimidine core and the phenyl rings. These hydrophobic groups can increase the lipophilicity of the molecule, which generally enhances membrane permeability as it allows the molecule to better interact with the lipid bilayer of the membrane.

3. **Phenyl Groups**: The molecule contains two phenyl rings, one of which is substituted with a chlorine atom. The aromatic rings can participate in π-π interactions with the membrane, potentially increasing permeability. The chlorine substituent can also contribute to the lipophilicity and may affect the electronic properties of the phenyl ring, further influencing membrane interaction.

4. **Carboxamide Groups**: The presence of two carboxamide groups introduces polar characteristics to the molecule. These groups can form hydrogen bonds with the membrane, which may either enhance or hinder permeability depending on the balance between hydrophilic and lipophilic interactions.

5. **Overall Lipophilicity and Hydrogen Bonding**: The combination of hydrophobic methyl and phenyl groups with polar carboxamide groups suggests that the given molecule has a balanced lipophilicity and potential for hydrogen bonding. This balance is crucial in determining the molecule's ability to permeate the artificial membrane, as it allows the molecule to interact with both the lipid and aqueous phases of the membrane.

In summary, the given molecule's structural features, including its heterocyclic core, methyl and phenyl substituents, and carboxamide groups, suggest that it would exhibit moderate to high permeability in the PAMPA assay. The balance of lipophilic and hydrophilic properties allows it to effectively interact with the artificial membrane, facilitating its passage.

Final answer: High permeability

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# 213

**SMILES:** CC1=C(C=CC=C1Cl)N2C(=C(C=N2)C(=O)NC3=C(C=C(C=C3)Br)F)C4CCNCC4

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several functional groups and structural elements that influence its permeability in the PAMPA assay. Let's break down these features and their impact on permeability:

1. **Pyrazole Core**: The central pyrazole ring is a five-membered heterocyclic compound containing two nitrogen atoms. Pyrazole rings are known for their stability and ability to participate in hydrogen bonding, which can enhance the molecule's interaction with the artificial membrane. This core structure is often associated with good permeability due to its planar and aromatic nature, which facilitates passage through lipid membranes.

2. **Amide Group**: The presence of a carboxamide group (a carbonyl group linked to a nitrogen atom) is significant for permeability. Amides can form hydrogen bonds, which may enhance the molecule's solubility and interaction with the membrane. However, the amide linkage can also introduce some rigidity and polarity, which might limit permeability depending on the overall balance with other hydrophobic or lipophilic parts of the molecule.

3. **Aromatic Rings**: The given molecule contains multiple aromatic rings, including a phenyl ring substituted with bromo and chloro groups, and another phenyl ring with a fluorine substituent. Aromatic rings generally increase lipophilicity, which can enhance membrane permeability. However, the presence of halogen substituents (bromo, chloro, and fluoro) can also introduce steric hindrance and alter electronic properties, potentially affecting the molecule's ability to permeate the membrane.

4. **Cyclohexyl Group**: The cyclohexyl group is a non-aromatic, saturated ring that can increase the lipophilicity of the molecule. Its bulkiness might hinder permeability by preventing the molecule from fitting snugly into the membrane pores. However, it can also contribute to the overall hydrophobic character, which is beneficial for permeability in lipid-rich environments.

5. **Substituents**: The bromo and chloro groups on the phenyl ring increase the molecule's lipophilicity, which can enhance permeability. The fluoro group can also contribute to lipophilicity while potentially affecting the electronic distribution, which might influence the molecule's interaction with the membrane.

Overall, the given molecule's structure suggests a balance between hydrophilic and lipophilic properties. The pyrazole core and aromatic rings contribute to lipophilicity, while the amide group and substituents provide opportunities for hydrogen bonding. This balance typically results in moderate to high permeability in the PAMPA assay, allowing the molecule to effectively interact with the artificial membrane.

Final answer: High permeability

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# 214

**SMILES:** CCOC(=O)N1CCC2=C(C1)SC(=C2C(=O)NC3=C(C=CC(=C3)Cl)OC)NCC4=C(C=CS4)C

**Label:** 0

**Predi:** 1

**Correct:** 0

# Response:
The given molecule is a complex organic compound that features several functional groups and structural elements that influence its permeability in the PAMPA assay. Let's break down the key components and their impact on permeability:

1. **Thienopyridine Core**: The presence of a thienopyridine core, which is a bicyclic structure combining a thiophene and a pyridine ring, contributes to the molecule's rigidity and planarity. This core can enhance the molecule's ability to interact with the artificial membrane, potentially increasing its permeability. The aromatic nature of the rings can facilitate π-π interactions with the membrane, which may aid in permeation.

2. **Methoxy and Chloro Substituents**: The methoxy group on the phenyl ring and the chloro substituent can influence the molecule's lipophilicity. The methoxy group is an electron-donating group, which can increase the electron density on the phenyl ring, potentially enhancing its interaction with the membrane. The chloro group is electron-withdrawing, which can also affect the electronic properties of the molecule, potentially increasing its lipophilicity and thus its permeability.

3. **Amino and Carbonyl Groups**: The presence of an amino group linked to the thienopyridine core and a carbonyl group in the ester moiety can form hydrogen bonds with the artificial membrane. These interactions can stabilize the molecule's orientation and enhance its permeability. However, the carbonyl group in the ester may also be susceptible to hydrolysis, which could affect the molecule's stability and permeability.

4. **Methylthio Group**: The methylthio group attached to the pyridine ring can increase the lipophilicity of the molecule, which is generally favorable for permeability. This group can also contribute to the overall stability of the molecule by providing steric bulk and electronic effects.

Overall, the given molecule's structural features suggest that it has a balance of hydrophobic and hydrophilic interactions, which can facilitate its permeability through the artificial membrane. The combination of aromatic rings, electron-donating and withdrawing groups, and hydrogen-bonding capabilities likely contribute to a moderate to high permeability profile in the PAMPA assay.

Final answer: High permeability

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# 215

**SMILES:** C1CCN(CC1)C(=O)C2=CC3=C(C=C2)N(C=N3)C4=CC=C(C=C4)Cl

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a member of the benzimidazole class, which is known for its potential biological activity and ability to interact with various biological targets. The structure of the given molecule includes a benzimidazole core, which is a bicyclic compound consisting of a benzene ring fused to an imidazole ring. This core is known for its stability and ability to participate in hydrogen bonding, which can enhance the molecule's interaction with biological membranes.

Additionally, the molecule contains a piperidine moiety, which is a six-membered nitrogen-containing heterocycle. Piperidine rings are often found in pharmacologically active compounds due to their basicity and ability to form hydrogen bonds, which can improve the molecule's solubility and permeability.

The presence of a chlorophenyl group attached to the benzimidazole core introduces a hydrophobic aromatic ring, which can enhance the molecule's lipophilicity. This increased lipophilicity can facilitate the molecule's passage through lipid membranes, potentially improving its permeability.

Overall, the combination of the benzimidazole core, piperidine moiety, and chlorophenyl group suggests that the given molecule may exhibit high permeability through the artificial membrane, as these structural features are conducive to membrane permeability and interaction with lipid bilayers.

Final answer: High permeability.

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# 216

**SMILES:** CNC1=C(N=C(O1)C2=C(C(=CC=C2)Cl)Cl)C#N

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is characterized by several functional groups and structural features that influence its permeability in the PAMPA assay. 

Firstly, the presence of the dichlorophenyl group contributes to the molecule's lipophilicity. Chlorine atoms are electronegative and can enhance the molecule's ability to interact with lipid membranes, potentially increasing its permeability. However, the dichlorophenyl group can also introduce steric hindrance, which might affect the molecule's ability to pass through the membrane.

The oxazole ring is a heterocyclic structure that can contribute to the molecule's rigidity and planarity. This structural feature can facilitate interactions with the artificial membrane, potentially enhancing permeability due to the favorable orientation and alignment of the molecule within the membrane.

The methylamino group introduces a basic nitrogen atom, which can form hydrogen bonds or ionic interactions with the membrane. This functional group can enhance the molecule's solubility in aqueous environments, which is important for its interaction with the PAMPA membrane.

Finally, the carbonitrile group is a polar functional group that can participate in hydrogen bonding and dipole-dipole interactions. This group can also influence the molecule's overall polarity and solubility, which are critical factors in determining its permeability.

Overall, the combination of lipophilic and polar functional groups, along with the structural rigidity provided by the oxazole ring, suggests that the given molecule may exhibit moderate permeability in the PAMPA assay. The dichlorophenyl group and the polar functional groups balance the molecule's ability to interact with the membrane, potentially leading to a moderate permeability profile.

Final answer: Low-to-moderate permeability.

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# 217

**SMILES:** CC1=C(C(=NO1)C2=CC=C(C=C2)F)COC3=NC=C(C=C3)C(=O)N4CCS(=O)(=O)CC4

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a complex organic compound with several functional groups and structural features that influence its permeability in the PAMPA assay. Let's break down these features and their potential impact on permeability:

1. **Aromatic Rings**: The molecule contains multiple aromatic rings, including a phenyl group and a thiazole ring. Aromatic rings can enhance lipophilicity, which often increases membrane permeability. However, the presence of a fluorine atom on the phenyl ring can also influence the electronic properties, potentially affecting the molecule's interaction with the membrane.

2. **Fluorine Substitution**: The fluorine atom on the phenyl ring can increase the molecule's lipophilicity and stability, which may enhance its permeability. Fluorine can also affect the electronic distribution, potentially altering the molecule's interaction with the membrane.

3. **Thiazole Ring**: The thiazole ring is a heterocyclic aromatic compound that can contribute to the molecule's overall stability and lipophilicity. This ring can also participate in hydrogen bonding and π-π interactions, which might influence the molecule's permeability.

4. **Methoxy Group**: The methoxy group attached to the thiazole ring can increase the molecule's lipophilicity, which generally enhances permeability. However, it can also introduce steric hindrance, which might affect the molecule's ability to interact with the membrane.

5. **Dioxepane Ring**: The dioxepane ring is a cyclic ether that can increase the molecule's solubility and flexibility. This ring can also influence the molecule's overall conformation, potentially affecting its permeability.

6. **Sulfonyl Group**: The sulfonyl group attached to the dioxepane ring is a polar functional group that can increase the molecule's hydrophilicity. This group can form strong hydrogen bonds and ionic interactions, which might enhance the molecule's solubility and permeability.

7. **Carbonyl Group**: The carbonyl group in the pyridinylmethanone moiety can participate in hydrogen bonding and dipole-dipole interactions. This group can also influence the molecule's polarity and solubility, which are important factors in permeability.

Overall, the given molecule has a combination of lipophilic and hydrophilic features, which suggests that it may have moderate permeability in the PAMPA assay. The presence of aromatic rings and fluorine substitution likely increases lipophilicity, while the sulfonyl and carbonyl groups contribute to hydrophilicity. The balance of these features will determine the molecule's ability to permeate the artificial membrane.

Final answer: Low-to-moderate permeability.

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# 218

**SMILES:** CN1C=NC=C1[C@@](C2=CC=C(C=C2)Cl)(C3=CC4=C(C=C3)N(C(=O)C=C4C5=CC(=CC=C5)Cl)C)N

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several functional groups and aromatic rings, which are key to its permeability characteristics in the PAMPA assay.

1. **Aromatic Rings**: The presence of multiple aromatic rings, including phenyl and quinoline rings, contributes to the molecule's hydrophobic character. Aromatic rings can facilitate interactions with the hydrophobic regions of the artificial membrane, enhancing permeability. The chlorophenyl groups add to this hydrophobicity and may also participate in π-π stacking interactions with the membrane.

2. **Amino Group**: The amino group attached to the phenyl ring can form hydrogen bonds with the artificial membrane, potentially increasing the molecule's solubility and permeability. This group can also act as a site for protonation, which may influence the molecule's overall charge and interaction with the membrane.

3. **Methyl Groups**: The presence of methyl groups, such as those on the quinoline and phenyl rings, increases the lipophilicity of the molecule. This can enhance the ability of the molecule to traverse the lipid bilayer of the artificial membrane.

4. **Quinolinone Core**: The quinolinone structure is a planar, aromatic system that can interact with the membrane through π-π interactions. The carbonyl group in the quinolinone can also participate in hydrogen bonding, which may aid in membrane permeation.

Overall, the given molecule's combination of aromatic rings, functional groups, and lipophilic characteristics suggest that it would have high permeability in the PAMPA assay. The balance of hydrophobic and hydrophilic interactions with the artificial membrane likely facilitates its passage through the membrane, indicating high permeability.

Final answer: High permeability

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# 219

**SMILES:** C1=CC(=CC(=C1)F)NC(=O)C2=CC(=NN2)C3=CC=CN3

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is an aromatic amide, which suggests that it contains an amide functional group attached to an aromatic ring. This structural feature is significant in determining the molecule's permeability.

The presence of the pyrazole rings in the structure indicates that the molecule has heterocyclic aromatic characteristics. Pyrazole rings are known for their ability to participate in hydrogen bonding and π-π stacking interactions, which can influence the molecule's interaction with the artificial membrane.

The 3-fluorophenyl group introduces a fluorine atom into the aromatic ring, which can affect the molecule's lipophilicity and electronic properties. Fluorine is highly electronegative, which can enhance the molecule's ability to interact with the membrane through dipole-dipole interactions or hydrogen bonding, depending on the environment.

The carboxamide group is another key feature, as it can form hydrogen bonds with the membrane, potentially increasing the molecule's permeability. However, the amide group can also introduce some rigidity and planarity to the molecule, which might affect its ability to fit into the membrane's pores.

Overall, the combination of aromatic rings, heterocycles, and functional groups like the fluorophenyl and carboxamide groups suggests that the given molecule may have moderate permeability due to its ability to engage in various non-covalent interactions with the artificial membrane. However, the specific permeability would depend on the exact nature of these interactions and the overall molecular conformation.

Final answer: Low-to-moderate permeability.

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# 220

**SMILES:** COC1=NC=C(C=C1)C2=CC(=CN3C2=CN=C3)C4=C5C=NNC5=CC=C4

**Label:** 0

**Predi:** 1

**Correct:** 0

# Response:
The given molecule is a complex structure that includes multiple aromatic rings and heterocycles, which are key to understanding its permeability characteristics. The molecule contains a pyridine ring, an indole moiety, and an imidazo[1,2-a]pyridine system. These features are significant in determining the molecule's interaction with the artificial membrane used in the PAMPA assay.

The pyridine ring is a nitrogen-containing heterocycle, which can participate in hydrogen bonding and dipole-dipole interactions. This can enhance the molecule's solubility and permeability, as the nitrogen atom can interact with the polar environment of the artificial membrane.

The indole moiety is a bicyclic structure that includes a benzene ring fused to a pyrrole ring. Indole is known for its planar structure and ability to participate in π-π stacking interactions. This can facilitate the molecule's passage through the membrane by allowing it to interact with other aromatic systems within the membrane.

The imidazo[1,2-a]pyridine system is another nitrogen-containing heterocycle, which can also engage in hydrogen bonding and dipole interactions. This contributes to the molecule's overall polarity and can enhance its permeability by allowing it to interact favorably with the membrane.

Overall, the combination of these aromatic and heterocyclic systems in the given molecule suggests that it can effectively interact with the artificial membrane, leading to high permeability. The presence of multiple nitrogen atoms and aromatic rings allows for a balance of hydrophilic and hydrophobic interactions, which is beneficial for permeability in the PAMPA assay.

Final answer: High permeability.

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# 221

**SMILES:** CC(C)OC1=CC=C(C=C1)CNC(=O)C2CCN(CC2)C(=O)N3CCOC4=C3C=C(C=C4)Cl

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that can be analyzed for its permeability based on its structural features. The molecule contains several key components that influence its behavior in the PAMPA assay:

1. **Benzoxazine Ring**: The presence of a benzoxazine moiety, specifically a 2-chloro-1,4-benzoxazine, suggests that the molecule has a relatively rigid and planar structure. This can enhance its ability to interact with the artificial membrane, potentially increasing its permeability. The chloro substituent may also contribute to the molecule's lipophilicity, aiding in membrane penetration.

2. **Piperidine Ring**: The piperidine ring is a saturated six-membered nitrogen-containing heterocycle. This structure is known for its basicity and ability to form hydrogen bonds, which can facilitate interactions with the membrane. The presence of a carboxamide group attached to the piperidine ring further enhances its ability to form hydrogen bonds, potentially increasing its permeability.

3. **Carboxamide Linkage**: The carboxamide group is a polar functional group that can participate in hydrogen bonding. This can increase the molecule's solubility in aqueous environments, which is beneficial for permeability in the PAMPA assay.

4. **Aromatic Ether**: The propan-2-yloxy group attached to a phenyl ring introduces an ether linkage, which can increase the molecule's lipophilicity. This can enhance the molecule's ability to traverse lipid membranes, contributing to its permeability.

Overall, the given molecule's structural features, such as the benzoxazine ring, piperidine ring, and aromatic ether, suggest that it has a balance of hydrophilic and lipophilic properties. This balance is often associated with moderate to high permeability in PAMPA assays, as it allows the molecule to interact effectively with both the aqueous and lipid phases of the membrane. Therefore, the given molecule is likely to exhibit high permeability in the PAMPA assay.

Final answer: High permeability

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# 222

**SMILES:** CC1=CC(=C(C=C1)C)NC2=C(C(=O)C3=CC=CC=C32)C4=CC=C(C=C4)C(F)(F)F

**Label:** 0

**Predi:** 1

**Correct:** 0

# Response:
The given molecule is a complex organic compound that features several functional groups and aromatic rings, which play a crucial role in its permeability characteristics.

The core structure of the given molecule is based on an indene framework, which is a bicyclic compound consisting of a benzene ring fused to a cyclopentene. This structure is known for its rigidity and planarity, which can facilitate interactions with the artificial membrane, potentially enhancing permeability.

Attached to this indene core are two phenyl groups, each substituted with different functional groups. One phenyl group is substituted with a trifluoromethyl group, which is highly electronegative and can increase the lipophilicity of the molecule. This increased lipophilicity can enhance the molecule's ability to traverse lipid membranes, contributing to higher permeability.

The other phenyl group is substituted with a methyl group, which is less electronegative compared to the trifluoromethyl group. While the methyl group also contributes to the overall hydrophobic character of the molecule, its effect is less pronounced than that of the trifluoromethyl group.

Additionally, the presence of an amino group linked to the indene core introduces a site for hydrogen bonding, which can influence the molecule's interaction with the artificial membrane. This functional group can form hydrogen bonds with the membrane, potentially affecting the permeability by either enhancing or reducing it, depending on the specific interactions.

Overall, the combination of aromatic rings, the trifluoromethyl group, and the amino group suggests that the given molecule likely exhibits high permeability in the artificial membrane, as these features collectively enhance its lipophilicity and facilitate interactions with the membrane.

Final answer: High permeability.

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# 223

**SMILES:** C1CCN(C1)C(=O)C2=NC(=C3N2C=CC=C3)C4=CN=C(C=C4)Cl

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a complex organic compound that features several distinct structural components, each contributing to its permeability characteristics in the PAMPA assay.

1. **Chloropyridine Moiety**: The presence of a chloropyridine group introduces a chlorine atom attached to a pyridine ring. Chlorine atoms can enhance lipophilicity, which often increases the permeability of a molecule through lipid membranes. However, the pyridine ring itself is a polar aromatic heterocycle, which can also interact with polar environments, potentially affecting the overall permeability balance.

2. **Imidazo[1,2-a]pyridine Core**: This bicyclic structure is a fused ring system combining an imidazole and a pyridine. The imidazole ring is known for its ability to participate in hydrogen bonding and other polar interactions, which can influence the molecule's solubility and permeability. The pyridine component, as mentioned earlier, is polar and can also engage in hydrogen bonding.

3. **Pyrrolidinylmethanone Group**: The pyrrolidine ring is a saturated five-membered nitrogen-containing ring, which is relatively non-polar. This can contribute to the lipophilicity of the molecule, potentially enhancing its permeability. The methanone linkage introduces a carbonyl group, which is polar and can form hydrogen bonds, affecting the molecule's interaction with the membrane.

Overall, the given molecule contains both lipophilic and polar components. The chloropyridine and pyrrolidinylmethanone groups contribute to lipophilicity, which generally enhances permeability through lipid membranes. However, the imidazo[1,2-a]pyridine core and the pyridine ring introduce polar characteristics that can interact with polar environments, potentially limiting permeability. The balance of these features suggests that the given molecule may exhibit moderate permeability in the PAMPA assay, as it has both lipophilic and polar components that can interact with the artificial membrane in a balanced manner.

Final answer: Low-to-moderate permeability.

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# 224

**SMILES:** C1=CC=C2C(=C1)N=C3C=CC=C(C3=N2)O

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule, 6-hydroxyphenazine, is a derivative of phenazine, which is a nitrogen-containing heterocyclic compound. The presence of the hydroxy group on the phenazine ring system significantly influences its chemical properties and permeability.

The phenazine core is a planar, aromatic structure, which contributes to the molecule's ability to interact with biological membranes. Aromatic compounds often have good lipophilicity, which can enhance their ability to permeate lipid membranes. However, the presence of the hydroxy group introduces a polar functional group, which can form hydrogen bonds with water molecules or other polar entities in the membrane.

In the context of the Parallel Artificial Membrane Permeability Assay (PAMPA), the artificial membrane mimics the lipid bilayer of biological membranes. The given molecule's permeability is determined by the balance between its lipophilic aromatic core and the polar hydroxy group. The hydroxy group can enhance solubility in aqueous environments, potentially reducing the overall lipophilicity of the molecule.

Considering these factors, the given molecule is likely to exhibit low-to-moderate permeability in the PAMPA assay. The hydroxy group may limit its ability to permeate the membrane compared to non-polar aromatic compounds, resulting in a moderate permeability profile.

Final answer: Low-to-moderate permeability.

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# 225

**SMILES:** COC1=CC=CC(=C1CNC2=CC=C(C=C2)S(=O)(=O)NC3=NC=CS3)O

**Label:** 0

**Predi:** 0

**Correct:** 1

# Response:
The given molecule is a sulfonamide, which is a class of compounds known for their antibacterial properties. The sulfonamide group is characterized by the presence of a sulfonyl functional group attached to an amine. This group is known to enhance the molecule's ability to interact with biological targets, such as enzymes or receptors, due to its polar nature and ability to form hydrogen bonds.

The molecule also contains a methoxyphenyl group, which is a phenyl ring substituted with a methoxy group. This substitution can increase the lipophilicity of the molecule, potentially enhancing its ability to permeate lipid membranes. The presence of the methoxy group can also influence the electronic properties of the phenyl ring, which may affect the molecule's interaction with the artificial membrane.

Additionally, the molecule features a thiazole ring, which is a five-membered ring containing both sulfur and nitrogen atoms. The thiazole ring can contribute to the molecule's overall stability and may also play a role in its binding affinity to biological targets due to its aromatic nature and ability to participate in π-π interactions.

The combination of these functional groups suggests that the given molecule may have moderate permeability to the artificial membrane. The sulfonamide group provides polar characteristics, which can facilitate interaction with the membrane, while the methoxyphenyl group may enhance lipophilicity, aiding in membrane permeation. However, the overall permeability will depend on the balance between these polar and non-polar characteristics, as well as the specific properties of the artificial membrane used in the assay.

Final answer: Low-to-moderate permeability.

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# 226

**SMILES:** C1CN(CCN(C1)C2=NC=C(C=C2)C(F)(F)F)CC3=CC(=O)N4C=CC=CC4=N3

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex structure that includes several key features influencing its permeability in the PAMPA assay. Let's break down these features and their implications:

1. **Trifluoromethyl Group**: The presence of a trifluoromethyl group on the pyridine ring is significant. This group is highly electronegative and lipophilic, which can enhance the molecule's ability to penetrate lipid membranes. The trifluoromethyl group can increase the overall hydrophobicity of the molecule, potentially improving its permeability through the artificial membrane.

2. **Pyridine Ring**: The pyridine ring is a heteroaromatic structure that can contribute to the molecule's overall stability and ability to interact with the membrane. The nitrogen in the pyridine ring can participate in hydrogen bonding or ionic interactions, which may facilitate binding to the membrane or active sites.

3. **Piperidine Ring**: The piperidine moiety is a saturated nitrogen-containing ring that can enhance the molecule's solubility and permeability. Piperidine rings are often found in pharmacologically active compounds due to their ability to interact with biological targets and improve membrane permeability.

4. **Dihydropyrido[1,2-a]pyrimidin-2-one Core**: This bicyclic structure is a fused ring system that can provide rigidity and planarity to the molecule. The presence of nitrogen atoms in this core can contribute to hydrogen bonding and ionic interactions, which may aid in the molecule's interaction with the membrane.

Overall, the given molecule's structural features suggest that it has a combination of hydrophobic and hydrophilic properties, which can facilitate its passage through the artificial membrane. The trifluoromethyl group enhances lipophilicity, while the piperidine and pyridine rings contribute to solubility and potential interactions with the membrane. These characteristics collectively suggest that the given molecule would exhibit high permeability in the PAMPA assay.

Final answer: High permeability

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# 227

**SMILES:** CC(C)(C)C1=CC=C(C=C1)C(=O)N2CC(=O)NC3=C(C2C4=CC=C(C=C4)F)C=C(C=C3)F

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a member of the benzodiazepine class, which is known for its central nervous system activity. The benzodiazepine core structure is a seven-membered diazepine ring fused to a benzene ring, which is a common feature in many psychoactive drugs. This core structure is crucial for the molecule's ability to interact with the GABA-A receptor, enhancing the inhibitory effects of the neurotransmitter GABA.

The presence of a fluorine atom on the benzodiazepine ring can significantly influence the molecule's pharmacokinetic properties, such as its lipophilicity and metabolic stability. Fluorine is a small, highly electronegative atom that can enhance the molecule's ability to cross biological membranes, such as the blood-brain barrier, thus increasing its central nervous system activity.

The molecule also contains a p-fluorophenyl group and a tert-butyl group. The p-fluorophenyl group contributes to the molecule's lipophilicity, which can enhance its ability to permeate lipid membranes. The tert-butyl group is a bulky hydrophobic moiety that can further increase the molecule's lipophilicity and may also play a role in steric interactions with biological targets.

Overall, the structural features of the given molecule, including the benzodiazepine core, fluorine substitution, and hydrophobic groups, suggest that it has high permeability to lipid membranes, which is consistent with its classification as a benzodiazepine with potential central nervous system activity.

Final answer: High permeability.

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# 228

**SMILES:** CC1=CN=C(N=C1C2=CC(=CC=C2)N(C)C)N3CCC(CC3)C(=O)N

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a pyrimidine derivative with a piperidine ring and a carboxamide group. The presence of these functional groups and the overall structure influence its permeability in the PAMPA assay.

1. **Pyrimidine Ring**: The pyrimidine core is a heterocyclic aromatic compound, which can contribute to the molecule's ability to interact with biological membranes. Pyrimidines are known for their planar structure, which can facilitate stacking interactions with aromatic amino acids in proteins or within lipid bilayers. This can enhance the molecule's permeability.

2. **Piperidine Ring**: The piperidine ring is a saturated six-membered ring containing a nitrogen atom. This ring can increase the molecule's solubility and flexibility, potentially aiding in its permeation through the artificial membrane. The presence of the piperidine ring can also influence the molecule's basicity, which may affect its interaction with the membrane.

3. **Carboxamide Group**: The carboxamide group is a polar functional group that can form hydrogen bonds with the artificial membrane. This can enhance the molecule's interaction with the membrane and potentially increase its permeability. However, the presence of this group can also introduce some degree of polarity, which might limit permeability if the membrane is highly lipophilic.

4. **Dimethylamino Group**: The dimethylamino group is a basic functional group that can participate in ionic interactions with the membrane. This group can enhance the molecule's solubility in aqueous environments and may facilitate its passage through the membrane by interacting with negatively charged components.

Overall, the given molecule's structure suggests that it has a balance of hydrophobic and hydrophilic properties, which can facilitate its permeability through the artificial membrane. The combination of aromatic, basic, and polar functional groups indicates that the molecule is likely to have moderate to high permeability in the PAMPA assay.

Final answer: High permeability

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# 229

**SMILES:** C1=CC=NC(=C1)N[S+](=O)(C2=CC=C(C=C2)NC(=O)CC3=CC(=C(C=C3)Cl)Cl)[O-]

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a sulfonamide, which is a class of compounds known for their antibacterial properties. The sulfonamide group is characterized by the presence of a sulfonyl functional group attached to an amine. In this molecule, the sulfonamide group is linked to a phenyl ring that is further substituted with dichloro groups. This dichlorophenyl moiety can influence the molecule's lipophilicity, potentially enhancing its ability to permeate lipid membranes.

The presence of the acetamide group, which is a carbonyl group attached to an amine, can also play a role in the molecule's permeability. Amide groups are generally polar, which can affect the solubility and permeability of the molecule. However, in this case, the acetamide group is connected to a phenyl ring, which can provide some degree of hydrophobic character, potentially aiding in membrane permeability.

The pyridinyl moiety, which is a nitrogen-containing heterocycle, can contribute to the molecule's overall polarity and hydrogen bonding capabilities. This can influence the molecule's interaction with the artificial membrane, potentially affecting its permeability.

Overall, the combination of the dichlorophenyl group, the sulfonamide linkage, and the pyridinyl moiety suggests that the given molecule may exhibit moderate permeability in the artificial membrane, balancing between hydrophilic and hydrophobic interactions.

Final answer: Low-to-moderate permeability.

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# 230

**SMILES:** CC(=O)NC1=CC=C(C=C1)NC(=O)C(C2=CC=CC=C2)NS(=O)(=O)C3=CC=C(S3)Br

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a sulfonamide, which is a class of compounds known for their antibacterial properties. The sulfonamide group is characterized by the presence of a sulfonyl functional group attached to an amine. This group is known to enhance the molecule's ability to interact with biological targets, such as enzymes or receptors, due to its polar nature and ability to form hydrogen bonds.

In the given molecule, the sulfonamide group is attached to a phenyl ring, which is a common structural motif in many bioactive compounds. The presence of the phenyl ring can contribute to the molecule's lipophilicity, potentially aiding in its ability to permeate lipid membranes.

Additionally, the molecule contains a thiophene ring, which is a five-membered aromatic ring containing sulfur. Thiophene rings are known to enhance the electronic properties of a molecule, which can influence its interaction with biological targets and its overall pharmacokinetic properties, including permeability.

The acetamido group in the molecule is another polar functional group that can participate in hydrogen bonding, which may further enhance the molecule's solubility and permeability.

The presence of a bromophenyl group introduces a halogen atom, which can affect the molecule's electronic distribution and lipophilicity. Bromine is a relatively large halogen, and its presence can increase the molecule's overall size and influence its interaction with biological membranes.

Overall, the combination of these functional groups suggests that the given molecule may have moderate to high permeability in the PAMPA assay due to its balance of polar and non-polar characteristics, as well as its ability to form hydrogen bonds and interact with lipid membranes.

Final answer: Low-to-moderate permeability.

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# 231

**SMILES:** CC1=CC(=C(N1C2=CC=CC(=C2)C#N)C)C3=NN=C4N3CCCCC4

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound with several distinct structural features that influence its permeability in the PAMPA assay. Let's break down these features and their implications:

1. **Triazolopyridazine Moiety**: This part of the molecule consists of a triazole ring fused to a pyridazine ring. The presence of nitrogen atoms in these heterocyclic rings can contribute to hydrogen bonding and polar interactions with the artificial membrane. These interactions can enhance the molecule's ability to permeate the membrane, suggesting high permeability.

2. **Dimethyl Substitution**: The dimethyl groups attached to the triazolopyridazine moiety increase the hydrophobic character of the molecule. This hydrophobicity can facilitate the passage of the molecule through the lipid-like environment of the artificial membrane, promoting permeability.

3. **Cyclopenta[b]pyridine Ring**: This bicyclic structure adds to the rigidity and planarity of the molecule, which can affect its ability to fit into the membrane's pores. The presence of a methyl group on this ring further enhances hydrophobic interactions, potentially increasing permeability.

4. **Benzonitrile Group**: The benzonitrile moiety introduces a nitrile group, which is polar and can engage in dipole-dipole interactions with the membrane. This can contribute to the molecule's overall ability to permeate the membrane, balancing the hydrophobic effects of the other parts of the molecule.

Overall, the given molecule exhibits a combination of polar and non-polar characteristics, with a balance of hydrophobic and hydrophilic interactions. These features suggest that the molecule would have high permeability in the PAMPA assay, as it can effectively interact with and traverse the artificial membrane.

Final answer: High permeability.

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# 232

**SMILES:** COC1=C(C=CC(=C1)/C=C(\C#N)/C2=NC3=CC=CC=C3N2)OCC4=CC=C(C=C4)F

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a member of benzimidazoles, which are known for their biological activity and potential pharmaceutical applications. The structure of the given molecule includes several key features that influence its permeability:

1. **Benzimidazole Moiety**: The presence of the benzimidazole ring is significant as it is a planar, aromatic heterocycle. This moiety can enhance the molecule's ability to interact with biological membranes due to its aromatic nature, which can facilitate stacking interactions with lipid bilayers. Benzimidazoles are often associated with good membrane permeability due to their ability to traverse lipid environments.

2. **Methoxy and Fluorophenyl Groups**: The methoxy group attached to the aromatic ring can increase the molecule's lipophilicity, which generally enhances membrane permeability. The presence of a fluorine atom in the fluorophenyl group can also increase lipophilicity and may improve the molecule's ability to penetrate lipid membranes due to the strong electron-withdrawing nature of fluorine, which can affect the electronic distribution of the molecule.

3. **Nitrile Group**: The nitrile group in the molecule can contribute to its polarity, which may affect its permeability. While nitrile groups can be polar, they are often involved in hydrogen bonding and dipole-dipole interactions, which can influence the molecule's interaction with the artificial membrane.

4. **Conjugated System**: The presence of a conjugated system, as indicated by the methoxyphenyl and nitrile linkage, can enhance the molecule's ability to interact with the membrane through π-π interactions. This conjugation can also affect the electronic properties of the molecule, potentially influencing its permeability.

Overall, the combination of these structural features suggests that the given molecule likely exhibits high permeability in the artificial membrane, as the aromatic and lipophilic characteristics are generally favorable for membrane permeation.

Final answer: High permeability

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# 233

**SMILES:** CCN(CC)CCN1C2=C(C=CC(=C2)OCCN(CC)CC)C(=O)C3=C1C=C(C=C3)Cl

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is an acridine derivative, which is a class of compounds known for their planar aromatic structures. The acridine core is a tricyclic structure consisting of two benzene rings fused to a pyridine ring. This planar structure is significant because it can facilitate interactions with biological membranes, often enhancing permeability due to its ability to intercalate between lipid bilayers.

The presence of a chloro substituent on the acridine ring can influence the molecule's electronic properties, potentially affecting its ability to interact with the artificial membrane. Chlorine atoms can increase the lipophilicity of the molecule, which may enhance its ability to traverse lipid membranes.

Additionally, the molecule contains a diethylaminoethoxy side chain. This functional group is a common feature in molecules designed to improve solubility and membrane permeability. The diethylamino group is a basic moiety that can participate in ionic interactions with the membrane, while the ethoxy linkage provides flexibility and helps in orienting the molecule within the membrane.

Overall, the combination of the acridine core, chloro substituent, and diethylaminoethoxy side chain suggests that the given molecule is likely to exhibit high permeability in the artificial membrane, as these structural features are conducive to membrane interaction and permeation.

Final answer: High permeability.

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# 234

**SMILES:** CN1C=C(C(=N1)C2C3=C(CCCC3=O)NC(=N2)NC4=NC5=CC=CC=C5O4)Cl

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several distinct structural components, each contributing to its permeability characteristics in the PAMPA assay.

1. **Quinazoline Core**: The quinazoline moiety is a bicyclic structure that is known for its planar aromatic nature. This planarity and aromaticity can facilitate interactions with the artificial membrane, potentially enhancing permeability. The presence of a chlorine atom on the quinazoline ring can also influence the molecule's lipophilicity, which is a key factor in membrane permeability. Chlorine atoms can increase the hydrophobic character of the molecule, which may enhance its ability to traverse lipid membranes.

2. **Pyrimidinyl Group**: The pyrimidinyl group is a heterocyclic aromatic ring that can contribute to the molecule's overall aromaticity and planarity. This can aid in membrane permeability by allowing the molecule to interact favorably with the lipid bilayer of the artificial membrane. The presence of a methyl group on the pyrimidine ring can further modulate lipophilicity, potentially enhancing permeability by increasing hydrophobic interactions with the membrane.

3. **Benzoxazole Moiety**: The benzoxazole ring is another heterocyclic aromatic structure that can contribute to the molecule's overall aromatic character. The benzoxazole group is known for its ability to participate in π-π stacking interactions, which can be beneficial for binding to the artificial membrane. Additionally, the presence of a nitrogen atom in the benzoxazole ring can introduce hydrogen bonding capabilities, which may also play a role in membrane permeability.

4. **Tetrahydroquinazolinone Structure**: The tetrahydroquinazolinone portion of the molecule introduces a partially saturated ring system, which can affect the overall rigidity and flexibility of the molecule. This structural feature may influence how the molecule fits into the membrane, potentially affecting its permeability.

Overall, the given molecule's combination of aromatic and heterocyclic structures, along with its functional groups, suggests that it may exhibit high permeability in the PAMPA assay. The presence of lipophilic and aromatic components likely enhances its ability to interact with the artificial membrane, facilitating its passage through the membrane.

Final answer: High permeability

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# 235

**SMILES:** CNC1=NC=CC(=N1)C2=CC=CC3=CC=CC=C32

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a derivative of quinoline, which is a heterocyclic aromatic organic compound. The structure of the given molecule includes a quinoline moiety, which is known for its planar aromatic structure. This planar nature can facilitate interactions with biological membranes, potentially enhancing permeability.

Additionally, the molecule contains a pyrimidine ring, which is a six-membered ring containing two nitrogen atoms. The presence of nitrogen atoms in the pyrimidine ring can contribute to hydrogen bonding and polar interactions, which may influence the molecule's ability to permeate through the artificial membrane.

The N-methyl group attached to the pyrimidine ring introduces a degree of lipophilicity, which can enhance the molecule's ability to traverse lipid membranes. However, the balance between hydrophilic and lipophilic properties will ultimately determine the permeability.

Overall, the combination of the aromatic quinoline moiety, the pyrimidine ring with nitrogen atoms, and the N-methyl group suggests that the given molecule may exhibit moderate to high permeability in the PAMPA assay, depending on the balance of these structural features.

Final answer: Low-to-moderate permeability.

------
# 236

**SMILES:** CC1=CC2=C(C=C1)OC3=C(C2=O)C(N(C3=O)CCCN4CCOCC4)C5=CC(=C(C=C5)OC)OC

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound with several functional groups and structural features that influence its permeability in the PAMPA assay. Let's break down these features and their impact on permeability:

1. **Dimethoxyphenyl Group**: The presence of methoxy groups on the phenyl ring increases the lipophilicity of the molecule. Methoxy groups are electron-donating, which can enhance the molecule's ability to interact with the lipid-like environment of the artificial membrane. This can increase the permeability of the molecule through the membrane.

2. **Cyclopenta[b]chromene Core**: This bicyclic structure contributes to the rigidity and planarity of the molecule. The chromene moiety is a fused aromatic system, which can facilitate π-π interactions with the membrane. The rigidity and planarity can also help the molecule to fit into the membrane's structure, potentially enhancing permeability.

3. **Morpholine Group**: The morpholine ring is a heterocyclic amine that can introduce some hydrophilicity to the molecule. This group can form hydrogen bonds with the membrane, which may aid in permeation. However, the balance between hydrophilic and lipophilic properties will determine the overall permeability.

4. **Dione Functionalities**: The presence of two carbonyl groups (dione) in the structure can participate in hydrogen bonding and dipole-dipole interactions with the membrane. These interactions can be beneficial for permeability, but they also introduce some degree of polarity, which might limit permeability if the balance with lipophilicity is not favorable.

5. **Methyl Substitution**: The methyl group on the chromene ring adds to the lipophilicity of the molecule, which can enhance its ability to traverse the lipid-like membrane.

Overall, the given molecule has a balance of lipophilic and hydrophilic features. The methoxy groups and the chromene core suggest a strong lipophilic character, which is likely to dominate the permeability profile. The morpholine and dione groups introduce some polar characteristics, which may allow for specific interactions with the membrane. In the context of the PAMPA assay, these features suggest that the given molecule would exhibit high permeability through the artificial membrane.

Final answer: High permeability

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# 237

**SMILES:** COC1=CC=C(C=C1)NC2=C(C(=O)C3=CC=CC=C32)C4=CC=C(C=C4)C(F)(F)F

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that includes several functional groups and aromatic rings, which influence its permeability in the PAMPA assay. 

The core structure of the molecule is based on an indene framework, which is a bicyclic compound consisting of a benzene ring fused to a cyclopentene. This structure is relatively planar and aromatic, contributing to the molecule's overall stability and potential for interaction with the artificial membrane.

Attached to this core are two phenyl groups, one of which is substituted with a trifluoromethyl group. The trifluoromethyl group is highly electronegative due to the presence of fluorine atoms, which can increase the lipophilicity of the molecule. This lipophilic character enhances the molecule's ability to traverse lipid membranes, suggesting high permeability.

Additionally, the other phenyl group is substituted with an anilino group, which contains an amino group attached to a phenyl ring. The presence of the amino group can introduce hydrogen bonding capabilities, which may facilitate interactions with the artificial membrane. However, the overall effect of this group on permeability would depend on the balance between its hydrophilic and lipophilic interactions.

The combination of these structural features suggests that the given molecule likely exhibits high permeability in the PAMPA assay due to its aromatic and lipophilic nature, enhanced by the trifluoromethyl group.

Final answer: High permeability.

------
# 238

**SMILES:** CCN(CC)CCCC(C)NC1=C2C=CC(=CC2=NC(=C1)/C=C/C3=CC=CC=C3Cl)Cl

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a quinoline derivative with a complex structure that includes several functional groups and substituents. To predict its permeability in the PAMPA assay, we need to consider the following structural features:

1. **Quinoline Core**: The presence of the quinoline core is significant as it is a planar aromatic system. Quinoline derivatives are known for their ability to interact with biological membranes due to their aromatic nature, which can facilitate stacking interactions with lipid bilayers. This suggests that the given molecule may have moderate to high permeability due to the quinoline core's ability to penetrate lipid membranes.

2. **Chlorophenyl Group**: The chlorophenyl group attached to the quinoline ring introduces a hydrophobic character to the molecule. Chlorine atoms can enhance lipophilicity, which may improve the molecule's ability to traverse lipid membranes. This group can also contribute to the overall stability of the molecule within the membrane environment.

3. **Diamine Side Chain**: The presence of a diaminopentane side chain introduces polar amine groups, which can form hydrogen bonds with the membrane or the artificial membrane in the PAMPA assay. These interactions can enhance the molecule's solubility in aqueous environments and potentially improve its permeability. However, the balance between hydrophobic and hydrophilic properties will determine the overall permeability.

4. **Diethyl Substitution**: The diethyl substitution on the diamine chain adds further hydrophobic character, which can enhance membrane permeability by increasing the molecule's lipophilicity.

Overall, the given molecule's structure suggests that it has a balance of hydrophobic and hydrophilic properties, with the quinoline core and chlorophenyl group contributing to its lipophilicity, while the diamine side chain provides potential for hydrogen bonding. This combination of features likely results in moderate to high permeability in the PAMPA assay, allowing the molecule to effectively interact with the artificial membrane.

Final answer: High permeability

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# 239

**SMILES:** CC1=C(C=CC(=C1)Br)NC(=O)C(C2=CC=CC=C2)NS(=O)(=O)C3=CC=CS3

**Label:** 0

**Predi:** 0

**Correct:** 1

# Response:
The given molecule is a sulfonamide, which is a class of compounds known for their antibacterial properties. The sulfonamide group is characterized by the presence of a sulfonyl functional group attached to an amine. In this molecule, the sulfonamide group is linked to a thiophene ring, which is a five-membered aromatic ring containing sulfur. This structural feature can influence the molecule's ability to interact with biological membranes.

The presence of the thiophene ring can enhance the molecule's lipophilicity, which is the ability to dissolve in fats, oils, and lipids. This property can facilitate the passage of the molecule through lipid membranes, potentially increasing its permeability. Additionally, the aromatic nature of the thiophene ring can contribute to the molecule's ability to engage in π-π interactions with aromatic amino acids in proteins, which may further influence its permeability.

The molecule also contains a phenyl group substituted with a bromine atom and a methyl group. The bromine atom is a relatively large and electronegative substituent, which can affect the molecule's electronic distribution and steric properties. This can influence the molecule's interaction with the artificial membrane, potentially affecting its permeability.

Overall, the combination of the sulfonamide group, thiophene ring, and substituted phenyl group suggests that the given molecule may exhibit moderate to high permeability in the PAMPA assay, depending on the balance of its lipophilic and electronic properties.

Final answer: Low-to-moderate permeability.

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# 240

**SMILES:** COC1=CC2=C(C=C1)C(=C(N2CC3=CC=C(C=C3)C=C)C(=O)O)CNC4CCCCC4

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a complex organic compound that belongs to the indole class, characterized by a bicyclic structure consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. This core structure is significant in many biologically active compounds.

The molecule features several functional groups and substituents that influence its permeability:

1. **Indole Core**: The indole structure is known for its planar and aromatic nature, which can facilitate interactions with biological membranes. The aromaticity and rigidity of the indole core can enhance the molecule's ability to traverse lipid membranes.

2. **Methoxy Group**: The presence of a methoxy group on the aromatic ring can increase the molecule's lipophilicity, enhancing its ability to permeate lipid bilayers. This group can also participate in hydrogen bonding, which may affect the molecule's interaction with the artificial membrane.

3. **Phenyl Methyl Group**: The phenyl ring attached via a methylene bridge contributes to the overall hydrophobic character of the molecule. This can further enhance membrane permeability by increasing the molecule's affinity for lipid environments.

4. **Cyclohexylamino Group**: The cyclohexylamino moiety introduces a bulky, hydrophobic group that can interact with the lipid components of the membrane. The presence of the amino group may also allow for hydrogen bonding or ionic interactions, which can influence the molecule's permeability.

5. **Carboxylic Acid Group**: The carboxylic acid group is a polar functional group that can form hydrogen bonds and ionic interactions with the membrane. This group can also affect the molecule's solubility and permeability, potentially limiting its passage through the membrane due to its polar nature.

Overall, the given molecule's combination of aromatic, hydrophobic, and polar groups suggests that it may exhibit moderate permeability in the PAMPA assay. The balance between hydrophobic and hydrophilic interactions will determine its ability to permeate the artificial membrane.

Final answer: Low-to-moderate permeability.

------
# 241

**SMILES:** CCN1C=C(C2=CC(=C(C=C2C1=O)OC)OC)C(=O)N3CCN(CC3)C4=CC(=CC=C4)Cl

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that can be analyzed for its permeability based on its structural features. The molecule contains several functional groups and structural motifs that influence its behavior in the PAMPA assay.

1. **Quinoline Core**: The presence of a quinoline core, which is a bicyclic structure consisting of a benzene ring fused to a pyridine ring, is significant. Quinoline derivatives are known for their ability to interact with biological membranes, often enhancing permeability due to their planar aromatic structure. This can facilitate passage through lipid bilayers.

2. **Methoxy Groups**: The two methoxy groups attached to the quinoline ring increase the molecule's lipophilicity. Methoxy groups can enhance membrane permeability by increasing the molecule's ability to dissolve in lipid environments, which is crucial for crossing biological membranes.

3. **Piperazine Ring**: The piperazine moiety, which is a six-membered ring containing two nitrogen atoms, is a common feature in many pharmaceuticals. It can enhance solubility and permeability due to its basic nature, which allows it to form ionic interactions with the membrane. The presence of a chlorophenyl group attached to the piperazine ring further increases lipophilicity, potentially improving membrane permeability.

4. **Carbonyl Group**: The carbonyl group (ketone) in the molecule can participate in hydrogen bonding with the membrane, which may aid in its permeation. However, the presence of this group can also introduce some polarity, which might reduce permeability compared to purely hydrophobic molecules.

Overall, the given molecule's structure suggests that it has a balance of hydrophobic and hydrophilic properties, which is typical for molecules with moderate to high permeability in PAMPA assays. The combination of aromatic rings, methoxy groups, and the piperazine moiety likely contributes to its ability to traverse the artificial membrane, indicating a high permeability.

Final answer: High permeability

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# 242

**SMILES:** C1=CC=C(C=C1)C2=CSC(=N2)NC(=O)C3=C(C=NC=C3)NS(=O)(=O)C4=CC=CC=C4C#N

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a sulfonamide, which is a class of compounds known for their antibacterial properties. The sulfonamide group is characterized by the presence of a sulfonyl functional group attached to an amine. In this molecule, the sulfonamide group is linked to a phenyl ring, which can influence the molecule's lipophilicity and, consequently, its permeability.

The presence of the cyano group on the phenyl ring introduces a polar characteristic, which can affect the molecule's solubility and permeability. The cyano group is a strong electron-withdrawing group, which can increase the molecule's polarity and potentially enhance its ability to interact with polar environments, such as aqueous media.

The pyridine ring in the structure contributes to the molecule's basicity and can participate in hydrogen bonding, which may facilitate interactions with the artificial membrane. Pyridine rings are often involved in π-π stacking interactions, which can stabilize the molecule's binding to the membrane.

The thiazole ring is a heterocyclic compound containing both sulfur and nitrogen, which can contribute to the molecule's overall stability and reactivity. The presence of this ring can enhance the molecule's ability to penetrate biological membranes due to its aromatic nature.

The benzamide moiety is a common structural feature in many bioactive compounds, and it can enhance the molecule's ability to interact with biological targets through hydrogen bonding and hydrophobic interactions.

Overall, the combination of these functional groups suggests that the given molecule may exhibit moderate permeability in the PAMPA assay. The balance of hydrophobic and hydrophilic characteristics, along with the potential for hydrogen bonding and π-π interactions, indicates that the molecule can traverse the artificial membrane, but may require some effort due to its complex structure.

Final answer: Low-to-moderate permeability.

------
# 243

**SMILES:** CCN1CCC(CC1)N(CC2=CC3=C(C=C2)OCO3)C(=O)NC4=C(C=CC(=C4)Cl)C(=O)OC

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound with several functional groups and structural features that influence its permeability in the PAMPA assay. Let's break down these features and their potential impact on permeability:

1. **Benzodioxole Ring**: The presence of a benzodioxole moiety, which is a fused aromatic ring system, contributes to the molecule's hydrophobic character. This hydrophobicity can enhance the molecule's ability to interact with the lipid components of the artificial membrane, potentially increasing its permeability.

2. **Piperidine Ring**: The piperidine ring is a saturated nitrogen-containing heterocycle. This ring can introduce basicity to the molecule, which may facilitate interactions with the membrane through hydrogen bonding or ionic interactions. The presence of an ethyl group on the piperidine ring can further increase the hydrophobicity, which may aid in membrane permeation.

3. **Chlorophenyl Group**: The chlorophenyl group is another aromatic moiety that contributes to the overall hydrophobicity of the molecule. The chlorine atom can also participate in halogen bonding, which may enhance binding to the membrane.

4. **Ester Linkage**: The ester group in the molecule, specifically the methyl ester, can be susceptible to hydrolysis. However, in the context of the PAMPA assay, the ester linkage may not significantly hinder permeability, as esters are relatively stable under neutral conditions.

5. **Amide Bond**: The amide linkage connecting the piperidine and benzodioxole moieties is a polar functional group that can participate in hydrogen bonding. This can influence the molecule's solubility and permeability, potentially allowing for some degree of interaction with the polar head groups of the artificial membrane.

Overall, the given molecule exhibits a balance of hydrophobic and polar characteristics, with multiple aromatic and heterocyclic components that can facilitate interactions with the artificial membrane. These features suggest that the molecule likely has high permeability in the PAMPA assay, as it can effectively traverse the lipid-rich environment of the membrane.

Final answer: High permeability

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# 244

**SMILES:** CCOC1=C(C=C(C=C1)CCNC(=O)C2=CC3=C(N2CC4=CC=CC(=N4)C)C=CC=N3)OCC

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a pyrrolopyridine derivative, which is a class of compounds known for their potential biological activity. In the context of the Parallel Artificial Membrane Permeability Assay (PAMPA), the molecule's permeability is influenced by its structural features.

The molecule contains several key functional groups and structural elements that contribute to its permeability:

1. **Ethoxy and Methylphenyl Groups**: The presence of an ethoxy group and a methylphenyl group in the molecule increases its lipophilicity. Lipophilic molecules tend to have higher permeability through lipid membranes, such as those found in biological systems. These groups can enhance the molecule's ability to interact with the hydrophobic environment of the artificial membrane.

2. **Pyrrolopyridine Core**: The pyrrolopyridine core is a bicyclic structure that can contribute to the molecule's rigidity and planarity. This structural feature can facilitate the molecule's passage through the membrane by allowing it to fit into the membrane's lipid bilayer more effectively. Additionally, the nitrogen atoms in the pyrrolopyridine ring can participate in hydrogen bonding, which may aid in the molecule's interaction with the membrane.

3. **Carboxamide Group**: The carboxamide group is a polar functional group that can form hydrogen bonds with the membrane. This group can enhance the molecule's solubility in aqueous environments, which is important for its transport across the membrane.

Overall, the combination of lipophilic groups, a rigid bicyclic core, and polar functional groups suggests that the given molecule would exhibit high permeability in the PAMPA assay. The balance of hydrophobic and hydrophilic properties allows the molecule to effectively interact with the artificial membrane, facilitating its passage.

Final answer: High permeability

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# 245

**SMILES:** CCOC(=O)C1=CC=C(C=C1)NC(=O)N2CC3=C(C[C@H]2C4=NC(=NO4)C(C)C)N=CN3

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a benzoate ester, which is a type of ester derived from benzoic acid. This structural feature is significant in the context of the Parallel Artificial Membrane Permeability Assay (PAMPA) because esters are often involved in drug permeability studies due to their ability to undergo hydrolysis and interact with biological membranes.

The molecule contains several key structural components that influence its permeability:

1. **Benzoate Ester Group**: The presence of the benzoate ester group suggests that the molecule may have moderate to high permeability. Esters are generally more lipophilic, which can enhance their ability to permeate lipid membranes. However, the ester linkage can also be a site for enzymatic hydrolysis, which may affect the molecule's stability and permeability.

2. **Triazole Ring**: The triazole ring is a heterocyclic compound that can contribute to the molecule's overall stability and lipophilicity. This ring can enhance the molecule's ability to interact with lipid bilayers, potentially increasing its permeability.

3. **Oxadiazole Ring**: The oxadiazole ring is another heterocyclic component that can influence the molecule's electronic properties and lipophilicity. This ring can also contribute to the molecule's ability to permeate through biological membranes.

4. **Carbamoyl Group**: The carbamoyl group is a functional group that can participate in hydrogen bonding. This can affect the molecule's solubility and permeability, potentially increasing its interaction with the artificial membrane.

5. **Phenyl Ring**: The phenyl ring is a hydrophobic aromatic group that can enhance the molecule's lipophilicity, aiding in its permeability through lipid-rich environments.

Overall, the combination of these structural features suggests that the given molecule likely has high permeability in the PAMPA assay. The balance of lipophilic and hydrophilic groups, along with the presence of heterocyclic rings, supports its ability to interact with the artificial membrane, facilitating its permeation.

Final answer: High permeability.

------
# 246

**SMILES:** COC1=CC=C(C=C1)C2=NOC(=N2)[C@@H]3CC4=C(CN3C(=O)NC5CCCCC5)NC=N4

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a complex structure that includes several distinct functional groups and ring systems, which contribute to its permeability characteristics in the PAMPA assay.

1. **Cyclohexyl Group**: The presence of a cyclohexyl group, a non-polar, hydrophobic moiety, can enhance the molecule's lipophilicity. This hydrophobic character can facilitate the molecule's interaction with the lipid components of the artificial membrane, potentially increasing its permeability.

2. **Methoxyphenyl Group**: The methoxyphenyl group introduces an aromatic ring with an ether linkage. The aromatic ring can participate in π-π interactions with the membrane, while the methoxy group can contribute to the molecule's overall polarity. This balance of hydrophobic and polar characteristics can influence the molecule's ability to traverse the membrane.

3. **Triazolopyrazine Ring System**: This bicyclic system is a heterocyclic structure that can contribute to the molecule's rigidity and planarity. The presence of nitrogen atoms in the ring can also introduce hydrogen bonding capabilities, which may affect the molecule's interaction with the membrane.

4. **Carboxamide Group**: The carboxamide group is polar and can form hydrogen bonds with the membrane. This functional group can enhance the molecule's solubility in aqueous environments and may facilitate its interaction with the membrane's polar head groups.

Overall, the given molecule's combination of hydrophobic and polar groups, along with its rigid and planar heterocyclic structure, suggests that it may have moderate permeability in the PAMPA assay. The balance of these features allows the molecule to interact with both the lipid and polar components of the artificial membrane, potentially enabling it to pass through the membrane with moderate efficiency.

Final answer: Low-to-moderate permeability.

------
# 247

**SMILES:** C1=CC=C(C=C1)C2=CSC(=N2)NC(=O)C3=C(C=NC=C3)NS(=O)(=O)C4=C(C=C(C=C4)F)F

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a sulfonamide, which is a class of compounds known for their antimicrobial properties. The sulfonamide group is characterized by the presence of a sulfonyl functional group attached to an amine. This group is known to enhance the molecule's ability to interact with biological membranes due to its polar nature, which can facilitate passage through lipid bilayers.

The presence of the difluorophenyl group in the molecule contributes to its lipophilicity, which can enhance membrane permeability by increasing the molecule's ability to dissolve in lipid environments. The fluorine atoms can also influence the electronic properties of the phenyl ring, potentially affecting the molecule's interaction with the artificial membrane.

The thiazole ring in the structure is a heterocyclic compound that can contribute to the molecule's overall stability and ability to interact with biological targets. Thiazole rings are often involved in hydrogen bonding and π-π interactions, which can be important for binding to specific sites on the artificial membrane.

The pyridine ring is another heterocyclic component that can enhance the molecule's ability to permeate through membranes. Pyridine rings are known for their basicity and ability to participate in hydrogen bonding, which can facilitate interactions with the membrane.

Overall, the combination of these functional groups and structural features suggests that the given molecule likely has high permeability to the artificial membrane. The balance of polar and non-polar characteristics, along with the presence of heterocyclic rings, supports its ability to traverse the membrane effectively.

Final answer: High permeability.

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# 248

**SMILES:** CC1=C(SC2=C1C(=N[C@H](C3=NN=C(N32)C)CC(=O)OC(C)(C)C)C4=CC=C(C=C4)Cl)C

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound with several distinct structural features that influence its permeability in the PAMPA assay. Let's break down these features and their implications:

1. **Tert-butyl Ester Group**: The presence of a tert-butyl ester group suggests that the molecule has increased lipophilicity. This group is bulky and hydrophobic, which can enhance the molecule's ability to interact with lipid membranes, potentially increasing its permeability.

2. **Chlorophenyl Group**: The 4-chlorophenyl moiety contributes to the molecule's overall hydrophobic character. The chlorine atom can also participate in halogen bonding, which may influence the molecule's interaction with the artificial membrane. This group can enhance the molecule's ability to traverse lipid bilayers, contributing to higher permeability.

3. **Triazatricyclic Core**: The triazatricyclic structure is a complex, rigid framework that can affect the molecule's conformational flexibility. This rigidity can influence how the molecule fits into the membrane, potentially affecting its permeability. The presence of nitrogen atoms in the tricyclic system may also allow for hydrogen bonding or ionic interactions with the membrane, which can either enhance or reduce permeability depending on the specific interactions.

4. **Tetrazole and Thia Moieties**: The tetrazole and thia components introduce heteroatoms (nitrogen and sulfur, respectively) into the structure, which can participate in hydrogen bonding and other polar interactions. These interactions can affect the molecule's solubility and permeability, potentially increasing it due to favorable interactions with the membrane.

5. **Methyl Substituents**: The presence of multiple methyl groups can increase the hydrophobic character of the molecule, which generally enhances permeability through lipid membranes.

Overall, the given molecule's combination of hydrophobic and rigid structural features, along with the presence of functional groups capable of interacting with the artificial membrane, suggests that it would exhibit high permeability in the PAMPA assay. The balance of lipophilic and polar interactions likely facilitates its passage through the membrane, making it a candidate for high permeability.

Final answer: High permeability

------
# 249

**SMILES:** C1=CC=C2C(=C1)C(=NC(=N2)C3=C(C=NC=C3)C#N)NC4=CC(=C(C=C4)F)F

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that belongs to the class of quinazolines. Its structure includes several key features that influence its permeability in the PAMPA assay.

1. **Quinazoline Core**: The quinazoline moiety is a bicyclic structure that is known for its planar and aromatic nature. This core contributes to the molecule's ability to interact with the artificial membrane, potentially enhancing its permeability due to the favorable stacking interactions and hydrophobic character.

2. **Pyridine Rings**: The presence of pyridine rings in the structure adds to the aromaticity and can influence the molecule's electronic properties. These rings can participate in π-π interactions with the membrane, which may facilitate permeation.

3. **Difluorophenyl Group**: The difluorophenyl group introduces fluorine atoms, which can enhance the lipophilicity of the molecule. Fluorine atoms are small and highly electronegative, which can increase the molecule's ability to penetrate lipid membranes by enhancing its overall hydrophobicity.

4. **Amino Linkage**: The amino linkage between the pyridine and quinazoline moieties can contribute to the molecule's flexibility and ability to form hydrogen bonds. This can affect the molecule's interaction with the membrane and its overall permeability.

5. **Carbonitrile Group**: The carbonitrile group is a polar functional group that can participate in hydrogen bonding and dipole-dipole interactions. While it may introduce some polarity, its presence in conjunction with the other hydrophobic and aromatic components could still allow for sufficient permeability.

Overall, the given molecule's combination of aromatic rings, fluorine substituents, and functional groups suggests that it would have high permeability in the PAMPA assay. The balance of hydrophobic and polar characteristics, along with the planar aromatic structure, likely facilitates its passage through the artificial membrane.

Final answer: High permeability

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# 250

**SMILES:** CC1=CC(=C(C=C1Cl)OC)NC(=O)CSC2=NC=C(C(=O)N2)S(=O)(=O)C3=CC=C(C=C3)C(C)(C)C

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a complex organic compound with several functional groups that influence its permeability in the PAMPA assay. Let's break down the structural features and their impact on permeability:

1. **Aromatic Rings**: The molecule contains multiple aromatic rings, including a chlorinated and methoxy-substituted phenyl ring, a phenyl ring with a tert-butyl group, and a pyrimidinyl ring. Aromatic rings generally enhance lipophilicity, which can increase membrane permeability due to their ability to interact with lipid bilayers through π-π interactions and van der Waals forces.

2. **Sulfur Linkage**: The presence of a sulfanyl (thioether) linkage between the pyrimidinyl ring and the acetamide moiety introduces a degree of flexibility and polarity. Sulfur atoms can participate in hydrogen bonding and can also affect the electronic properties of the molecule, potentially influencing its interaction with the membrane.

3. **Acetamide Group**: The acetamide group contributes to the molecule's polarity and can form hydrogen bonds with the membrane or the PAMPA assay components. This can enhance solubility in aqueous environments, which is crucial for permeability in biological systems.

4. **Tert-butyl Group**: The bulky tert-butyl group on the phenyl ring increases the steric hindrance, which can affect the molecule's ability to fit into the membrane pores. However, it also contributes to the lipophilicity of the molecule, potentially enhancing permeability through hydrophobic interactions.

5. **Chloro and Methoxy Substituents**: The chloro group is electronegative and can influence the electronic distribution within the molecule, potentially affecting its interaction with the membrane. The methoxy group is electron-donating and can increase lipophilicity, which may enhance permeability.

6. **Pyrimidinyl Ring**: The pyrimidinyl ring is a heterocyclic aromatic compound that can participate in π-π stacking interactions with the membrane. Its presence can also influence the molecule's overall electronic properties and solubility.

Overall, the given molecule's combination of aromatic rings, sulfur linkage, and various substituents suggests that it has a balance of hydrophobic and polar characteristics. This balance is likely to result in moderate permeability through the artificial membrane, as the molecule can interact with both the lipid and aqueous phases of the membrane.

Final answer: Low-to-moderate permeability.

------
# 251

**SMILES:** CC1=C(C=C(C=C1)NC(=O)NC2=CC3=C(C=C2N4CCCCC4)N(C(=O)N3C)C)Cl

**Label:** 0

**Predi:** 1

**Correct:** 0

# Response:
The given molecule is a complex organic compound that features several functional groups and structural elements that influence its permeability in the PAMPA assay. Let's break down these features and their implications:

1. **Benzimidazole Core**: The presence of a benzimidazole moiety in the given molecule suggests a potential for moderate to high permeability. Benzimidazole is a bicyclic structure that is relatively planar and can facilitate passage through lipid membranes due to its aromatic nature. This core can also engage in hydrogen bonding and π-π interactions, which may enhance its interaction with the artificial membrane.

2. **Piperidine Ring**: The piperidine ring is a saturated six-membered nitrogen-containing ring that can increase the molecule's basicity and solubility. This can enhance the molecule's ability to permeate through the membrane by increasing its interaction with the lipid bilayer and potentially forming ionic interactions with the membrane's polar head groups.

3. **Urea Linkage**: The urea linkage in the given molecule can contribute to hydrogen bonding capabilities, which may enhance its interaction with the artificial membrane. Urea groups are often involved in forming strong hydrogen bonds, which can stabilize the molecule's interaction with the membrane.

4. **Chloro and Methyl Substituents**: The chloro group on the phenyl ring can increase the lipophilicity of the molecule, which may enhance its permeability through the lipid-rich artificial membrane. The methyl group on the phenyl ring can also contribute to the molecule's lipophilicity, potentially aiding in membrane permeation.

5. **Overall Structure**: The combination of these functional groups and structural elements suggests that the given molecule is likely to have moderate to high permeability in the PAMPA assay. The aromatic and heterocyclic components, along with the lipophilic substituents, are likely to facilitate its passage through the artificial membrane.

Therefore, the given molecule is expected to exhibit high permeability in the PAMPA assay.

Final answer: High permeability

------
# 252

**SMILES:** CC1=CC=C(C=C1)S(=O)(=O)NC2=CC=CC=C2C(=O)NC3=NC(=C(S3)C)C4=CC=CC=C4

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a sulfonamide, which is a class of compounds known for their antibacterial properties. The sulfonamide group is characterized by the presence of a sulfonyl functional group attached to an amine. In this molecule, the sulfonamide group is linked to a phenyl ring, which can influence its solubility and permeability.

The molecule also contains a thiazole ring, which is a five-membered heterocyclic compound containing both sulfur and nitrogen. This ring can contribute to the molecule's overall stability and lipophilicity, potentially enhancing its ability to permeate biological membranes.

Additionally, the presence of a benzamide moiety, which includes an amide group attached to a benzene ring, can affect the molecule's polarity and hydrogen bonding capabilities. This can influence the molecule's interaction with the artificial membrane, potentially affecting its permeability.

Overall, the combination of these functional groups suggests that the given molecule may have moderate permeability due to the balance of hydrophobic and hydrophilic characteristics. The thiazole and phenyl rings contribute to lipophilicity, while the sulfonamide and benzamide groups provide some hydrophilic character. This balance is typical for molecules that need to traverse biological membranes while maintaining sufficient solubility in aqueous environments.

Final answer: Low-to-moderate permeability.

------
# 253

**SMILES:** CN(C)C(=O)C1=NC(=C2N1C=CN=C2)C3=C(C=C(C=C3)Cl)Cl

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound with several structural features that influence its permeability in the PAMPA assay. Let's break down these features and their implications:

1. **Dichlorophenyl Group**: The presence of a dichlorophenyl group, which is a phenyl ring substituted with two chlorine atoms, contributes to the molecule's lipophilicity. Chlorine atoms are electronegative and can enhance the molecule's ability to interact with lipid membranes, potentially increasing its permeability.

2. **Imidazo[1,2-a]pyridine Core**: This bicyclic structure is a fused ring system combining an imidazole and a pyridine ring. The nitrogen atoms in these rings can participate in hydrogen bonding and other polar interactions, which may affect the molecule's solubility and permeability. The rigidity of the fused ring system can also influence the molecule's ability to fit into the membrane pores.

3. **N,N-Dimethylcarboxamide Moiety**: The carboxamide group, particularly with N,N-dimethyl substitution, adds to the molecule's polarity. This functional group can form hydrogen bonds, which may enhance solubility in aqueous environments but can also affect membrane permeability by interacting with polar head groups of the membrane.

4. **Overall Lipophilicity**: The combination of lipophilic (dichlorophenyl) and polar (carboxamide) groups suggests that the given molecule has a balanced solubility profile, which is crucial for permeability. The dichlorophenyl group likely dominates, suggesting that the molecule may have a higher permeability due to its ability to traverse lipid-rich environments.

In summary, the given molecule's structural features, particularly the dichlorophenyl group and the imidazo[1,2-a]pyridine core, suggest that it has high permeability in the PAMPA assay. The balance between lipophilic and polar groups allows it to effectively interact with the artificial membrane, facilitating its passage.

Final answer: High permeability

------
# 254

**SMILES:** CC1=CC=CC=C1C2=NC3=CC=CC=C3C(=N2)NCC4=CC=C(C=C4)C5=CN=CC=C5

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a member of the quinazolines, which are known for their diverse biological activities, including their role as kinase inhibitors. The structure of the given molecule includes several key features that influence its permeability:

1. **Quinazoline Core**: The quinazoline moiety is a bicyclic structure that contributes to the molecule's planarity and rigidity. This core is often associated with good membrane permeability due to its ability to interact with lipid bilayers, facilitating passive diffusion.

2. **Aromatic Rings**: The presence of multiple aromatic rings, including the pyridine and phenyl groups, enhances the molecule's lipophilicity. Aromatic rings can participate in π-π interactions with the lipid components of the membrane, which can increase permeability.

3. **Methylenamine Linkage**: The methylenamine linkage connects the quinazoline core to the pyridinylphenyl group. This linkage provides flexibility to the molecule, allowing it to adapt its conformation to fit into the membrane's lipid bilayer.

4. **Substituted Phenyl Group**: The 2-methylphenyl group adds to the lipophilic character of the molecule. The methyl group can enhance hydrophobic interactions with the membrane, potentially increasing permeability.

Overall, the combination of a quinazoline core, multiple aromatic rings, and a flexible methylenamine linkage suggests that the given molecule likely exhibits high permeability in the PAMPA assay. These structural features enable the molecule to effectively interact with the artificial membrane, facilitating its passage through the lipid layer.

Final answer: High permeability

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# 255

**SMILES:** C1CN(CCC1C(=O)N)C2=NC(=CS2)C3=CC4=C(C=C3)OC=CC4=O

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a piperidinecarboxamide, which indicates that it contains a piperidine ring attached to a carboxamide group. This structural feature is often associated with a certain degree of flexibility and solubility, which can influence the molecule's permeability.

The molecule also contains a chromen-4-yl group, which is a derivative of chromene. Chromene structures are known for their aromatic properties, which can enhance the molecule's ability to interact with biological membranes through π-π interactions. This aromaticity can contribute to the molecule's overall lipophilicity, potentially increasing its permeability through lipid membranes.

Additionally, the molecule includes a thieno[3,2-b]pyridin-4-one moiety. This bicyclic structure combines sulfur and nitrogen heteroatoms, which can introduce polar characteristics to the molecule. The presence of these heteroatoms can enhance hydrogen bonding capabilities, which may affect the molecule's solubility and permeability. However, the aromatic nature of the thieno[3,2-b]pyridin-4-one moiety can also contribute to the molecule's lipophilicity, balancing its polar and non-polar properties.

Overall, the combination of aromatic and heteroaromatic features in the given molecule suggests that it may exhibit a balance of lipophilic and polar characteristics. This balance can result in moderate permeability through the artificial membrane, as the molecule can interact with both hydrophobic and hydrophilic environments. Therefore, the given molecule is likely to have low-to-moderate permeability in the Parallel Artificial Membrane Permeability Assay (PAMPA).

Final answer: Low-to-moderate permeability.

------
# 256

**SMILES:** CCC1=C(C=C(C=C1)NC(=O)C2=C(C(=C(N2)C)C(=O)C)C)[S+](=O)(NC3=CC=CC(=C3)C#N)[O-]

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a sulfonamide, which is a class of compounds known for their antibacterial properties. In the context of the Parallel Artificial Membrane Permeability Assay (PAMPA), the permeability of the molecule is influenced by its structural features.

The molecule contains several key functional groups and structural elements that contribute to its permeability:

1. **Sulfonamide Group**: The presence of the sulfonamide group, which includes a sulfonyl group attached to an amine, is a significant factor in the molecule's permeability. Sulfonamides are known for their ability to penetrate biological membranes, which is crucial for their activity as drugs. This group can enhance the molecule's solubility and facilitate its passage through lipid membranes.

2. **Aromatic Rings**: The molecule contains multiple aromatic rings, including a phenyl group and a pyrrole ring. Aromatic rings can increase the lipophilicity of the molecule, which often enhances membrane permeability. However, the presence of these rings can also lead to steric hindrance, potentially limiting permeability.

3. **Acetyl Group**: The acetyl group attached to the phenyl ring can influence the molecule's polarity and solubility. This group may enhance the molecule's ability to interact with lipid bilayers, contributing to its permeability.

4. **Ethyl and Methyl Substituents**: The ethyl and methyl groups on the pyrrole ring increase the hydrophobic character of the molecule. These groups can enhance membrane permeability by increasing the molecule's ability to dissolve in lipid environments.

5. **Amino Group**: The amino group attached to the phenyl ring can form hydrogen bonds with the membrane, potentially aiding in the molecule's permeability. However, it can also introduce some polarity, which may affect the balance between hydrophilicity and lipophilicity.

Overall, the given molecule's combination of hydrophobic and hydrophilic groups suggests that it may have moderate permeability in the PAMPA assay. The sulfonamide group, aromatic rings, and substituents contribute to its ability to interact with lipid membranes, while the balance of polar and non-polar groups may prevent it from being too hydrophobic or too hydrophilic. This balance is crucial for its potential as a drug, as it allows the molecule to effectively reach its target site within the body.

Final answer: Low-to-moderate permeability.

------
# 257

**SMILES:** CCOC(=O)C1=NN=C(S1)N[S+](=O)(C2=CC=C(C=C2)NC(=O)CC3=CC(=C(C=C3)Cl)Cl)[O-]

**Label:** 0

**Predi:** 0

**Correct:** 1

# Response:
The given molecule is a complex organic compound with several functional groups that influence its permeability in the PAMPA assay. Let's break down the structural features and their impact on permeability:

1. **Aromatic Rings**: The molecule contains a dichlorophenyl group and a phenyl group. Aromatic rings generally contribute to lipophilicity, which can enhance membrane permeability. However, the presence of chlorine atoms on the phenyl ring can increase the molecule's polarity, potentially reducing permeability due to decreased solubility in lipid membranes.

2. **Amide Linkage**: The molecule features an amide bond, which is a common structural motif in many bioactive compounds. Amides can form hydrogen bonds, which may facilitate interactions with the artificial membrane, potentially increasing permeability.

3. **Sulfonamide Group**: The sulfonamide linkage is known for its ability to form strong hydrogen bonds. This group can enhance the molecule's solubility in water, which might improve its permeability through the PAMPA membrane, which mimics biological membranes.

4. **Thiadiazole Ring**: The thiadiazole moiety is a heterocyclic compound that can contribute to the molecule's overall stability and electronic properties. This ring can influence the molecule's ability to interact with the membrane, potentially affecting permeability.

5. **Ester Group**: The ethyl ester group is a common feature in prodrugs, which can enhance lipophilicity and membrane permeability. However, esters can be hydrolyzed in biological systems, which might affect the molecule's stability and permeability.

Overall, the given molecule's permeability is likely influenced by the balance between its hydrophobic aromatic rings and polar functional groups like the sulfonamide and ester. The presence of both lipophilic and polar groups suggests that the molecule may exhibit moderate permeability in the PAMPA assay, with potential for both hydrophobic interactions and hydrogen bonding with the membrane.

Final answer: Low-to-moderate permeability.

------
# 258

**SMILES:** CN1C=C(C=C1C(=O)NC2=CC(=C(C=C2)Cl)C(F)(F)F)S(=O)(=O)N3CCCCCC3

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound with several functional groups that influence its permeability in the PAMPA assay. Let's break down the structural features and their impact on permeability:

1. **Pyrrole Ring**: The presence of a pyrrole ring, which is a five-membered aromatic heterocycle, contributes to the molecule's planarity and aromaticity. This can enhance the molecule's ability to interact with the artificial membrane, potentially increasing its permeability.

2. **Carboxamide Group**: The carboxamide group is a polar functional group that can form hydrogen bonds with the membrane. This interaction can facilitate the passage of the molecule through the membrane, contributing to moderate permeability.

3. **Chloro and Trifluoromethyl Substituents**: The chloro and trifluoromethyl groups are electron-withdrawing substituents that can increase the lipophilicity of the molecule. This increased lipophilicity can enhance the molecule's ability to traverse lipid membranes, suggesting higher permeability.

4. **Sulfonyl Group**: The sulfonyl group is a strong electron-withdrawing group that can increase the molecule's polarity. While this might reduce permeability due to increased hydrophilicity, its presence is balanced by the lipophilic substituents, potentially resulting in moderate permeability.

5. **Piperidine Ring**: The piperidine ring is a saturated nitrogen-containing heterocycle that can enhance the molecule's solubility and ability to form hydrogen bonds. This can contribute to moderate permeability by facilitating interactions with the membrane.

Overall, the given molecule exhibits a balance of lipophilic and polar characteristics due to its diverse functional groups. The aromatic and lipophilic components, such as the pyrrole ring and trifluoromethyl group, suggest that the molecule has high permeability, while the polar groups, like the carboxamide and sulfonyl, provide a counterbalancing effect, resulting in a moderate to high permeability profile in the PAMPA assay.

Final answer: High permeability.

------
# 259

**SMILES:** CC1=C(N(N=C1C(=O)NN2CCCCC2)C3=C(C=C(C=C3)Cl)Cl)C4=CC=C(C=C4)Cl

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a complex organic compound that features several functional groups and structural elements that influence its permeability in the PAMPA assay. Let's break down these features and their impact on permeability:

1. **Phenyl Groups**: The molecule contains two 4-chlorophenyl groups and one 2-chlorophenyl group. These aromatic rings contribute to the hydrophobic character of the molecule, which can enhance its ability to interact with the hydrophobic regions of the artificial membrane. However, the presence of chlorine atoms can also increase the molecule's overall polarity, potentially affecting its solubility and permeability.

2. **Pyrazole Ring**: The pyrazole ring is a five-membered heterocyclic structure that can contribute to the molecule's rigidity and planarity. This structural feature can influence the molecule's ability to fit into the membrane pores, potentially affecting its permeability.

3. **Carboxamide Group**: The carboxamide group is a polar functional group that can form hydrogen bonds with the membrane or surrounding environment. This can enhance the molecule's solubility in aqueous environments and may facilitate its passage through the membrane.

4. **Piperidine Ring**: The piperidine moiety is a saturated nitrogen-containing heterocycle that can increase the molecule's basicity. This can affect the molecule's ionization state, which in turn influences its permeability. The presence of the piperidine ring can also enhance the molecule's solubility in water due to its polar nature.

Overall, the given molecule's permeability in the PAMPA assay is likely influenced by a balance of hydrophobic and hydrophilic interactions. The aromatic rings and heterocyclic structures contribute to hydrophobic interactions, while the carboxamide and piperidine groups enhance hydrophilic interactions. The presence of chlorine atoms and the overall molecular structure suggest that the given molecule may exhibit moderate permeability, as it has both lipophilic and hydrophilic characteristics that need to be balanced for effective passage through the artificial membrane.

Final answer: Low-to-moderate permeability.

------
# 260

**SMILES:** CC1=CC=C(C=C1)S(=O)(=O)NC2=C(C=CN=C2)C(=O)NCC3=CC=CC=C3

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a sulfonamide, which is a class of compounds known for their antibacterial properties. The sulfonamide group is characterized by the presence of a sulfonyl functional group attached to an amine. In this molecule, the sulfonamide group is linked to a benzyl group, which is a phenyl ring attached to a methylene bridge. This benzyl group can enhance the lipophilicity of the molecule, potentially increasing its ability to permeate lipid membranes.

The molecule also contains a pyridine ring, which is a nitrogen-containing heterocycle. Pyridine rings can contribute to the molecule's ability to interact with biological targets through hydrogen bonding and π-π interactions, which may influence its permeability.

Additionally, the presence of a carboxamide group attached to the pyridine ring can enhance the molecule's solubility and ability to form hydrogen bonds, which may also affect its permeability.

Overall, the combination of these functional groups suggests that the given molecule may have moderate permeability due to the balance between its hydrophilic and lipophilic properties. The benzyl group increases lipophilicity, while the sulfonamide, pyridine, and carboxamide groups provide hydrophilic characteristics. This balance is typical for molecules that need to traverse biological membranes while maintaining sufficient solubility.

Final answer: Low-to-moderate permeability.

------
# 261

**SMILES:** CC1=C(N(C(=C1C(=O)C)C)C)C(=O)NC2=CC(=C(C=C2)OC)[S+](=O)(NC3=CC=C(C=C3)Br)[O-]

**Label:** 0

**Predi:** 1

**Correct:** 0

# Response:
The given molecule is a complex organic compound that features several functional groups and structural elements that influence its permeability in the PAMPA assay. Let's break down these features and their impact on permeability:

1. **Pyrrole Ring**: The presence of a pyrrole ring, which is a five-membered aromatic heterocycle containing nitrogen, contributes to the molecule's aromaticity and potential for hydrogen bonding. The pyrrole ring can enhance the molecule's ability to interact with the artificial membrane, potentially increasing its permeability.

2. **Acetyl Group**: The acetyl group attached to the pyrrole ring introduces a polar carbonyl group, which can form hydrogen bonds with the membrane. This can increase the molecule's solubility in the membrane environment, potentially enhancing its permeability.

3. **Methoxy and Dimethyl Substituents**: The methoxy group and the dimethyl substituents on the pyrrole ring increase the molecule's lipophilicity. Lipophilic molecules tend to have higher permeability through lipid membranes, suggesting that the given molecule may have moderate to high permeability due to these groups.

4. **Aromatic Amide Linkage**: The amide linkage connects the pyrrole ring to a phenyl group. Amides are generally polar and can participate in hydrogen bonding, which may aid in the molecule's interaction with the membrane. However, the presence of an aromatic amide may also contribute to some rigidity in the molecule's conformation, potentially affecting its ability to permeate the membrane.

5. **Bromophenyl Group**: The bromophenyl group introduces a bulky, electron-withdrawing bromine atom, which can influence the electronic distribution within the molecule. This may affect the molecule's ability to interact with the membrane, potentially reducing its permeability due to steric hindrance or altered electronic properties.

6. **Sulfamoyl Group**: The sulfamoyl group is a polar, hydrophilic moiety that can form strong hydrogen bonds. This group can increase the molecule's solubility in aqueous environments, which may enhance its permeability through the PAMPA membrane.

Overall, the given molecule's structure suggests a balance of hydrophilic and lipophilic properties, with several functional groups that can interact with the artificial membrane. The combination of aromaticity, polar functional groups, and lipophilic substituents likely results in moderate to high permeability in the PAMPA assay.

Final answer: High permeability

------
# 262

**SMILES:** C1CCN(C1)C2=C(C=C(C=C2)NC3=NC(=NC4=CC=CC=C43)C5=CC=NC=C5)F

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that belongs to the quinazoline class. Quinazolines are known for their diverse biological activities, often used in pharmaceuticals. The molecule's structure includes several key features that influence its permeability:

1. **Quinazoline Core**: The quinazoline core is a bicyclic structure that contributes to the molecule's rigidity and planarity. This core is often associated with good permeability due to its ability to interact with biological membranes, which are typically lipid-rich environments.

2. **Fluorophenyl Group**: The presence of a fluorine atom on the phenyl ring can enhance the molecule's lipophilicity, which is the ability to dissolve in fats, oils, and non-polar solvents. Fluorine's high electronegativity can also influence the electronic distribution within the molecule, potentially affecting its interaction with the artificial membrane.

3. **Pyridine and Pyrrolidine Rings**: The pyridine ring is a nitrogen-containing heterocycle that can participate in hydrogen bonding and other polar interactions. The pyrrolidine ring, a saturated nitrogen-containing heterocycle, adds to the molecule's flexibility and can enhance solubility in aqueous environments. These rings can influence the molecule's ability to traverse the membrane by providing sites for interaction with the membrane's polar head groups.

4. **Amino Group**: The presence of an amino group on the quinazoline ring can increase the molecule's basicity and ability to form hydrogen bonds. This can enhance the molecule's solubility in water and its interaction with the polar components of the artificial membrane.

Overall, the given molecule's combination of aromatic rings, heterocycles, and functional groups suggests that it has a balance of hydrophobic and hydrophilic properties, which is often desirable for good permeability. The quinazoline core, along with the fluorophenyl and heterocyclic groups, likely contribute to its ability to interact with the artificial membrane, indicating that it may have high permeability.

Final answer: High permeability

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# 263

**SMILES:** CNC1=C(C=CC(=N1)C2=CC=CC3=CC=CC=C32)C#N

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several functional groups and aromatic systems, which influence its permeability in the PAMPA assay.

Firstly, the presence of the naphthalene moiety, which is a polycyclic aromatic hydrocarbon, contributes to the hydrophobic character of the molecule. This hydrophobicity can enhance the molecule's ability to interact with the lipid components of the artificial membrane, potentially increasing its permeability.

Secondly, the pyridine ring in the structure is a heteroaromatic system that can participate in hydrogen bonding and other polar interactions. The nitrogen atom in the pyridine ring can act as a hydrogen bond acceptor, which may facilitate interactions with the polar head groups of the artificial membrane.

The nitrile group attached to the pyridine ring introduces a polar functional group, which can also engage in dipole-dipole interactions with the membrane. This group can enhance the molecule's solubility in polar solvents and may contribute to its overall permeability.

Lastly, the methylamino group is a secondary amine that can form hydrogen bonds and increase the molecule's overall polarity. This group can also enhance the molecule's solubility in polar environments, which may aid in its permeation through the artificial membrane.

Overall, the combination of hydrophobic and polar characteristics in the given molecule suggests that it may exhibit moderate to high permeability in the PAMPA assay, as it can effectively interact with both the lipid and polar components of the artificial membrane.

Final answer: High permeability.

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# 264

**SMILES:** CC1=CC=C(C=C1)C(=O)N2CCN(CC2)C3=NC=CC(=N3)NC4=CC=CC=C4OC

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several functional groups and structural motifs contributing to its permeability characteristics. Let's break down the structural components and their influence on permeability:

1. **Piperazine Ring**: The presence of a piperazine ring, which is a six-membered heterocyclic structure containing two nitrogen atoms, is a significant feature. Piperazine rings are known for their ability to enhance the solubility and permeability of molecules. This is due to the presence of nitrogen atoms, which can participate in hydrogen bonding and improve the molecule's interaction with biological membranes.

2. **Pyrimidine Ring**: The pyrimidine ring is another heterocyclic component in the given molecule. Pyrimidines are aromatic and can contribute to the molecule's overall stability and ability to interact with biological targets. The aromatic nature of the pyrimidine ring can facilitate π-π interactions with aromatic amino acids in proteins, potentially enhancing the molecule's ability to permeate biological membranes.

3. **Methanone Group**: The methanone group, which is a carbonyl group (C=O) attached to a phenyl ring, can influence the molecule's polarity and solubility. The carbonyl group is polar and can form hydrogen bonds, which may enhance the molecule's solubility in aqueous environments and its ability to permeate lipid membranes.

4. **Methoxyphenyl and Methylphenyl Groups**: These aromatic groups contribute to the lipophilicity of the molecule. The methoxy group (OCH3) is an electron-donating group, which can increase the electron density of the aromatic ring, potentially enhancing interactions with lipid bilayers. The methyl group (CH3) also contributes to the lipophilic character, which can facilitate membrane permeability by increasing the molecule's affinity for lipid environments.

Overall, the given molecule's structure suggests that it has a balance of hydrophilic and lipophilic properties, which is typical for molecules with moderate to high permeability in PAMPA assays. The presence of heterocyclic rings, aromatic groups, and functional groups capable of hydrogen bonding suggests that the molecule can effectively interact with both aqueous and lipid environments, enhancing its permeability across the artificial membrane.

Final answer: High permeability

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# 265

**SMILES:** C1CC2=C(C1)SC3=NC=NC(=C23)NC(=O)C4=CC=CO4

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a complex structure that includes a furan ring and a thienopyrimidine moiety. The furan ring is a five-membered aromatic ring containing one oxygen atom, which contributes to the molecule's overall aromaticity and potential for hydrogen bonding interactions. This can influence the molecule's solubility and permeability.

The thienopyrimidine moiety is a bicyclic structure that combines a thiophene ring and a pyrimidine ring. The presence of sulfur in the thiophene ring can enhance lipophilicity, which may improve the molecule's ability to traverse lipid membranes. The pyrimidine ring, being a nitrogen-containing heterocycle, can participate in hydrogen bonding and other polar interactions, which may affect the molecule's permeability.

The overall structure of the given molecule suggests that it has a balance of hydrophobic and hydrophilic characteristics, which is typical for molecules with moderate permeability. The aromatic rings can facilitate membrane permeability by allowing the molecule to interact with lipid bilayers, while the heteroatoms (oxygen, sulfur, and nitrogen) can engage in polar interactions that may influence the molecule's solubility and permeability.

Therefore, the given molecule is likely to exhibit low-to-moderate permeability in the PAMPA assay, as it possesses a combination of aromatic and heteroaromatic features that balance hydrophobic and hydrophilic interactions.

Final answer: Low-to-moderate permeability.

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# 266

**SMILES:** C1CN(CCC1C(=O)N)C2=NC(=CS2)C3=CC=CC=C3C(F)(F)F

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a piperidinecarboxamide, which is a type of compound featuring a piperidine ring attached to a carboxamide group. This structural motif is often associated with biological activity and can influence the molecule's pharmacokinetic properties, such as permeability.

The molecule contains several key structural components that contribute to its permeability:

1. **Piperidine Ring**: The piperidine ring is a six-membered nitrogen-containing heterocycle. This ring is relatively flexible and can enhance the molecule's ability to interact with biological membranes. Piperidine rings are commonly found in pharmaceuticals and are known to improve the solubility and permeability of compounds.

2. **Carboxamide Group**: The carboxamide group is a functional group that can form hydrogen bonds with biological targets or membranes. This can enhance the molecule's interaction with the artificial membrane, potentially increasing its permeability.

3. **Thiazole Ring**: The thiazole ring is a five-membered heterocycle containing both sulfur and nitrogen. This ring can contribute to the molecule's electronic properties and may influence its ability to permeate the membrane by affecting the overall polarity and electronic distribution of the molecule.

4. **Trifluoromethylphenyl Group**: The presence of a trifluoromethyl group attached to a phenyl ring can significantly impact the molecule's lipophilicity. The trifluoromethyl group is highly electronegative and can increase the molecule's ability to penetrate lipid membranes by enhancing its hydrophobic character.

Overall, the combination of these structural features suggests that the given molecule is likely to have high permeability in the PAMPA assay. The piperidine and thiazole rings, along with the trifluoromethyl group, contribute to a balance of hydrophilic and hydrophobic properties that favor membrane permeability. The carboxamide group can further enhance interactions with the membrane, supporting the molecule's ability to permeate the artificial membrane.

Final answer: High permeability.

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# 267

**SMILES:** CN1C=CC2=C(N=C(C=C21)C3=CC=CC=C3C#N)C(=O)NCC4=CN=CC=C4

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several functional groups and structural elements that influence its permeability in the PAMPA assay. Let's break down these features and their impact on permeability:

1. **Indole Core**: The presence of the indole moiety is significant as indole derivatives are known for their ability to permeate biological membranes. The indole structure is planar and aromatic, which can facilitate interactions with lipid bilayers, enhancing permeability.

2. **Cyanopyridine Group**: The cyano group attached to the pyridine ring introduces a polar character to the molecule. This can affect the molecule's solubility and permeability. The cyano group can form hydrogen bonds or dipole-dipole interactions with the artificial membrane, potentially increasing permeability.

3. **Methyl Substitution**: The methyl group on the indole ring can influence the molecule's lipophilicity. While small, the methyl group can enhance the hydrophobic character of the molecule, which may improve its ability to traverse the lipid-rich environment of the artificial membrane.

4. **Pyridine Ring**: The pyridine ring contributes to the aromatic character of the molecule, which can aid in membrane permeability due to its ability to participate in π-π interactions with the membrane.

5. **Carboxamide Group**: The carboxamide group is polar and can form hydrogen bonds, which may enhance the molecule's interaction with the artificial membrane. However, it can also introduce some degree of polarity that might limit permeability.

6. **Pyridinylmethyl Side Chain**: This side chain adds to the molecule's complexity and can influence its overall shape and flexibility. The pyridinylmethyl group can interact with the membrane through π-π stacking or hydrogen bonding, potentially enhancing permeability.

Overall, the given molecule's combination of aromatic rings, polar functional groups, and hydrophobic substituents suggests that it would exhibit high permeability in the PAMPA assay. The balance of hydrophobic and polar characteristics allows the molecule to effectively interact with the artificial membrane, facilitating its passage through the membrane.

Final answer: High permeability

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# 268

**SMILES:** CC1=C(C(=CC=C1)C)NC(=O)C2=NC(=NC=C2Cl)SC

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several functional groups and structural elements that influence its permeability in the PAMPA assay. Let's break down these features and their impact on permeability:

1. **Pyrimidine Ring**: The core structure of the given molecule is a pyrimidine ring, which is a heterocyclic aromatic compound. Pyrimidine rings are known for their planar structure, which can facilitate interactions with biological membranes. The aromatic nature of the pyrimidine ring can enhance the molecule's ability to pass through lipid membranes due to π-π stacking interactions and hydrophobic effects.

2. **Chloro Substituent**: The presence of a chloro group on the pyrimidine ring introduces a degree of polarity and can affect the molecule's overall lipophilicity. Chlorine atoms can increase the molecule's ability to interact with lipid bilayers, but they can also introduce steric hindrance, which might reduce permeability.

3. **Methyl Group**: The methyl group attached to the pyrimidine ring is a small, non-polar substituent that can increase the lipophilicity of the molecule. This can enhance membrane permeability by increasing the molecule's solubility in lipid environments.

4. **Thioether Linkage**: The thioether linkage (methylsulfanyl group) connects the pyrimidine ring to the phenyl ring. Thioethers are generally non-polar and can contribute to the lipophilicity of the molecule. This linkage can facilitate the passage of the molecule through lipid membranes by enhancing its hydrophobic interactions.

5. **Phenyl Ring**: The phenyl ring is another aromatic component that can contribute to the molecule's ability to permeate through membranes. Aromatic rings can engage in π-π interactions with the lipid bilayer, aiding in membrane permeability.

6. **Carboxamide Group**: The carboxamide group is a polar functional group that can form hydrogen bonds with the surrounding environment. While this group can increase the molecule's solubility in aqueous environments, it can also interact with polar sites on the membrane, potentially aiding in permeability.

Overall, the given molecule contains a combination of aromatic rings, a chloro substituent, and both polar and non-polar functional groups. These features suggest that the molecule has a balanced lipophilic and hydrophilic character, which is often desirable for good membrane permeability. The presence of aromatic rings and hydrophobic substituents likely contribute to high permeability, while the polar groups may facilitate interactions with the membrane surface. Therefore, the given molecule is likely to exhibit high permeability in the PAMPA assay.

Final answer: High permeability

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# 269

**SMILES:** CC1=CC(=C(C(=O)N1)CNC(=O)C2=C3C=CNC3=CC(=N2)C4=C(N=CC=C4)OC)C

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several functional groups and aromatic systems, which are key to its permeability characteristics in the PAMPA assay.

1. **Aromatic Systems**: The molecule contains multiple aromatic rings, including a pyridine ring and an indole ring. Aromatic systems are generally planar and can participate in π-π stacking interactions, which can enhance the molecule's ability to interact with the artificial membrane. These interactions can facilitate the passage of the molecule through the membrane, contributing to its permeability.

2. **Methoxy Group**: The presence of a methoxy group on the pyridine ring can increase the molecule's lipophilicity. Lipophilic molecules tend to have higher permeability as they can more easily traverse lipid membranes. The methoxy group can also influence the electronic properties of the pyridine ring, potentially affecting the molecule's interaction with the membrane.

3. **Carboxamide Group**: The carboxamide group is a polar functional group that can form hydrogen bonds with the artificial membrane. While this group can contribute to some degree of water solubility, which might reduce permeability, its ability to form hydrogen bonds can also facilitate specific interactions with the membrane, potentially aiding in permeation.

4. **Indole Ring**: The indole ring is a bicyclic structure that is often found in bioactive compounds. Its presence in the molecule suggests potential biological activity, which may also translate to moderate permeability. The indole ring can interact with the membrane through π-π stacking and other non-covalent interactions.

Overall, the given molecule's combination of aromatic systems, methoxy group, and carboxamide group suggests that it would exhibit moderate to high permeability in the PAMPA assay. The balance of lipophilic and polar characteristics allows it to interact favorably with the artificial membrane, facilitating its passage.

Final answer: High permeability

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# 270

**SMILES:** CCCCOC1=CC=C(C=C1)C(=O)N2CCC(CC2)C3=NNC(=O)N3C4=CC=C(C=C4)C

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that can be analyzed for its permeability based on its structural features. The molecule contains several key components that influence its permeability:

1. **Triazolone Ring**: The presence of a triazolone ring, which is a five-membered heterocyclic ring containing three nitrogen atoms, contributes to the molecule's ability to interact with biological membranes. This ring can enhance the molecule's ability to form hydrogen bonds and engage in polar interactions, which may facilitate its passage through the artificial membrane.

2. **Piperidine Ring**: The piperidine moiety, a six-membered nitrogen-containing ring, is known for its basicity and ability to form ionic interactions. This can increase the molecule's solubility in aqueous environments, potentially enhancing its permeability through the membrane.

3. **Butoxyphenyl Group**: The butoxyphenyl group introduces a hydrophobic character to the molecule. The presence of the butoxy chain can increase the lipophilicity of the molecule, which may enhance its ability to traverse lipid-rich membranes, such as the artificial membrane used in PAMPA.

4. **Methylphenyl Group**: The methyl group attached to the phenyl ring can further increase the lipophilicity of the molecule. This can also contribute to the molecule's ability to interact with the hydrophobic regions of the membrane.

Overall, the combination of polar and non-polar regions in the given molecule suggests that it may have moderate to high permeability in the PAMPA assay. The balance of hydrophilic and hydrophobic interactions allows the molecule to effectively interact with the artificial membrane, potentially facilitating its passage.

Final answer: High permeability

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# 271

**SMILES:** CN1CCN(CC1)C2=NC=CC(=C2)C3=NC4=CC=CC=C4C(=N3)NC5=CC(=C(C=C5)F)F

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex structure that includes several key functional groups and aromatic systems, which influence its permeability in the PAMPA assay.

1. **Aromatic Systems**: The molecule contains multiple aromatic rings, including a pyridine ring and a quinazoline ring. Aromatic systems are generally planar and can facilitate interactions with the artificial membrane, potentially enhancing permeability. The presence of these rings suggests that the molecule may have a degree of lipophilicity, which can aid in crossing lipid membranes.

2. **Fluorinated Aromatic Ring**: The presence of a difluorophenyl group introduces fluorine atoms, which can increase the lipophilicity of the molecule. Fluorine atoms can also influence the electronic properties of the aromatic ring, potentially affecting the molecule's ability to interact with the membrane.

3. **Piperazine Ring**: The piperazine moiety is a common feature in many pharmaceuticals and can enhance solubility and permeability. The nitrogen atoms in the piperazine ring can participate in hydrogen bonding, which may facilitate interaction with the membrane.

4. **Amino Groups**: The molecule contains amino groups attached to the quinazoline ring. These groups can form hydrogen bonds with the artificial membrane, potentially increasing permeability. However, they can also introduce polarity, which might reduce permeability if they are not balanced by sufficient hydrophobic character.

5. **Overall Structure**: The combination of aromatic systems, fluorine atoms, and the piperazine ring suggests that the given molecule has a balance of hydrophobic and hydrophilic properties. This balance is crucial for permeability, as it allows the molecule to interact with the lipid components of the membrane while maintaining sufficient solubility.

Considering these structural features, the given molecule is likely to exhibit high permeability in the PAMPA assay due to its aromatic nature, fluorine atoms, and the presence of the piperazine ring. These features collectively enhance its ability to interact with the artificial membrane, facilitating its passage through the lipid layers.

Final answer: High permeability.

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# 272

**SMILES:** CN(C)C1=CC=CC(=C1)C2=CN=C(C3=C2CCO3)NC4=CN=CC=C4

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a phenylpyridine, which is a structural motif known for its potential biological activity. To determine the permeability of this molecule in the PAMPA assay, we need to consider its structural features.

The molecule contains a pyridine ring, which is a nitrogen-containing heterocycle. Pyridine rings are known to enhance the solubility and permeability of compounds due to their polar nature. This can facilitate the passage of the molecule through the artificial membrane by interacting with the polar sites of the membrane.

Additionally, the molecule has a dimethylamino group attached to the phenyl ring. The presence of this electron-donating group can increase the lipophilicity of the molecule, which may enhance its ability to permeate lipid membranes. However, the dimethylamino group can also increase the molecule's overall polarity, which can balance the lipophilicity and potentially improve permeability.

The furo[3,2-b]pyridine moiety in the molecule introduces a fused heterocyclic system, which can contribute to the rigidity and planarity of the molecule. This structural feature can affect the molecule's ability to fit into the membrane pores, potentially enhancing permeability.

Overall, the combination of polar and lipophilic groups in the given molecule suggests that it may have moderate to high permeability in the PAMPA assay. The balance of these features allows the molecule to interact with both polar and non-polar regions of the artificial membrane, facilitating its passage.

Final answer: High permeability.

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# 273

**SMILES:** CCOC(=O)C1=C(SC2=C1CCN(C2)C(=O)OCC)NC(=O)CN3CCCCC3

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a thienopyridine derivative, which is a class of compounds known for their potential biological activity, often used in pharmaceuticals. The thienopyridine core is a bicyclic structure consisting of a thiophene ring fused to a pyridine ring. This core structure is known for its planar and aromatic characteristics, which can influence the molecule's ability to interact with biological membranes.

The presence of the ethyl ester group in the molecule suggests that it may have moderate lipophilicity, which can enhance its ability to permeate lipid membranes. Esters are often involved in increasing the hydrophobic character of a molecule, which can facilitate its passage through the lipid bilayer of cell membranes.

Additionally, the molecule contains a piperidine moiety, which is a six-membered nitrogen-containing ring. Piperidine rings are known to increase the basicity of a molecule, which can enhance its solubility in aqueous environments and potentially improve its interaction with biological targets. However, the piperidine ring may also introduce steric hindrance, which could affect the molecule's permeability.

The presence of multiple amide linkages in the molecule suggests potential hydrogen bonding capabilities, which can influence the molecule's interaction with the artificial membrane. Amide groups can form hydrogen bonds with the membrane's polar head groups, potentially facilitating or hindering permeability depending on the orientation and availability of these groups.

Overall, the combination of the thienopyridine core, ethyl ester group, piperidine moiety, and amide linkages suggests that the given molecule may exhibit moderate permeability in the artificial membrane. The balance of hydrophobic and hydrophilic characteristics, along with potential hydrogen bonding, will dictate its ability to traverse the membrane.

Final answer: Low-to-moderate permeability.

------
# 274

**SMILES:** CC1=C(C(=CC=C1)C)C(=O)NC2=CC(=C(C=C2)OC)[S+](=O)(NC3=CC=C(C=C3)Br)[O-]

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a benzamide derivative, which is a class of compounds known for their potential biological activity, often used in pharmaceuticals. The structure of the given molecule includes several key features that influence its permeability:

1. **Benzamide Core**: The presence of the benzamide moiety suggests that the molecule has a planar structure, which can facilitate interactions with biological membranes. Benzamides are known for their ability to permeate lipid bilayers due to their aromatic nature, which allows for van der Waals interactions with the lipid components of the membrane.

2. **Aromatic Rings**: The molecule contains multiple aromatic rings, including a bromophenyl group and a methoxyphenyl group. Aromatic rings are hydrophobic and can enhance the molecule's ability to interact with the hydrophobic regions of the artificial membrane, increasing its permeability.

3. **Bromine Substitution**: The bromine atom on the phenyl ring can increase the molecule's lipophilicity, which is the ability to dissolve in fats, oils, and lipids. This can enhance the molecule's permeability by allowing it to more easily pass through the lipid-rich environment of the membrane.

4. **Methoxy and Methyl Groups**: The methoxy and methyl groups on the phenyl rings can also contribute to the molecule's lipophilicity. These groups can increase the overall hydrophobic character of the molecule, which can enhance its ability to permeate the artificial membrane.

5. **Sulfonamide Linkage**: The sulfonamide group is a polar functional group that can form hydrogen bonds with the artificial membrane. While this may seem counterintuitive for permeability, the sulfonamide group can also help the molecule to orient itself correctly within the membrane, potentially facilitating its passage.

Overall, the combination of aromatic rings, halogen substitution, and polar functional groups in the given molecule suggests that it would have high permeability in the artificial membrane. The balance of hydrophobic and hydrophilic interactions allows the molecule to effectively interact with the membrane, enhancing its ability to permeate through it.

Final answer: High permeability.

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# 275

**SMILES:** C[C@H]1C/C=C/C2[C@@H](C(=C)[C@H](C3[C@@]2([C@H](/C=C/[C@](C1)(C)O)OC(=O)C)C(=O)N[C@H]3CC4=CC=CC=C4)C)O

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound with a tricyclic core structure, which is indicative of a rigid and potentially lipophilic framework. The presence of multiple rings, including a tricyclic system, suggests that the molecule has a relatively large and complex three-dimensional shape, which can influence its interaction with the artificial membrane.

The molecule contains several functional groups that are relevant to its permeability:

1. **Hydroxyl Groups**: The presence of two hydroxyl groups contributes to the molecule's polarity and potential for hydrogen bonding. These groups can enhance the molecule's solubility in aqueous environments and may facilitate interactions with the polar head groups of the artificial membrane.

2. **Acetate Ester**: The acetate group is an ester functional group, which can increase the lipophilicity of the molecule. Esters are often involved in passive diffusion through lipid membranes, suggesting that the acetate group may enhance the permeability of the molecule through the artificial membrane.

3. **Methyl and Methylidene Groups**: The presence of multiple methyl groups and a methylidene group increases the hydrophobic character of the molecule. These groups can enhance the molecule's ability to interact with the lipid components of the artificial membrane, potentially increasing its permeability.

4. **Benzyl Group**: The benzyl group adds to the lipophilicity of the molecule and can facilitate interactions with the hydrophobic regions of the artificial membrane. Aromatic groups like benzyl can also participate in π-π interactions, which may further influence the molecule's permeability.

5. **Tricyclic Core**: The rigid tricyclic core structure can affect the overall shape of the molecule, potentially allowing it to fit into specific regions of the artificial membrane. This structural feature can influence the molecule's ability to traverse the membrane by providing a defined conformation that may interact favorably with the membrane.

Overall, the combination of polar and non-polar functional groups, along with the rigid tricyclic core, suggests that the given molecule is likely to have moderate to high permeability in the artificial membrane. The balance of hydrophilic and hydrophobic interactions, along with the structural rigidity, supports its ability to diffuse through the membrane, making it suitable for further evaluation in drug discovery applications.

Final answer: High permeability

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# 276

**SMILES:** C1=CC=C(C=C1)CNC2=NC(=NC3=CC=CC=C32)NCC4=CC=CC=C4

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a derivative of quinazoline, which is a bicyclic compound consisting of a benzene ring fused to a pyrimidine ring. This core structure is known for its planar and aromatic characteristics, which can influence the molecule's ability to permeate through biological membranes.

The presence of the quinazoline core suggests that the given molecule may have moderate to high permeability due to its aromatic nature, which can facilitate interactions with the lipid bilayer of a membrane. Aromatic compounds often have good membrane permeability because they can engage in π-π interactions with the aromatic amino acids present in membrane proteins.

Additionally, the given molecule contains benzyl groups attached to the nitrogen atoms. These benzyl groups are also aromatic, contributing to the overall hydrophobic character of the molecule. This hydrophobicity can enhance the molecule's ability to traverse lipid-rich environments, such as cell membranes.

However, the presence of amine groups in the structure introduces potential sites for hydrogen bonding, which can affect the molecule's solubility and permeability. While these amine groups can form hydrogen bonds with the membrane, they may also increase the molecule's polarity, potentially reducing its permeability compared to a purely hydrophobic compound.

Overall, the given molecule's aromatic quinazoline core and benzyl substituents suggest that it may have high permeability, but the amine groups could introduce some degree of polarity that might moderate this permeability. Therefore, the final answer is: 

Final answer: High permeability.

------
# 277

**SMILES:** CC1=C(C(C(=C(N1)C)C(=O)OCCCN2CCC(CC2)(C3=CC=CC=C3)C4=CC=CC=C4)C5=CC(=CC=C5)[N+](=O)[O-])C(=O)OC

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a complex organic compound that includes several functional groups and structural features that influence its permeability in the PAMPA assay. Let's break down these features and their potential impact on permeability:

1. **Dihydropyridine Core**: The presence of a dihydropyridine ring is a key feature in many calcium channel blockers. This structure is generally lipophilic, which can enhance the molecule's ability to permeate lipid membranes. However, the specific substituents on this core can significantly alter its permeability.

2. **Dimethyl Substitution**: The dimethyl groups on the dihydropyridine ring increase the lipophilicity of the molecule. This can enhance membrane permeability by increasing the molecule's ability to dissolve in the lipid bilayer of the artificial membrane.

3. **Nitrophenyl Group**: The nitrophenyl group is a bulky and polar moiety. While it can contribute to the overall lipophilicity of the molecule, its presence may also introduce steric hindrance and polar interactions that could hinder permeability.

4. **Piperazine Ring**: The piperazine moiety is a common feature in many pharmaceuticals, often contributing to improved solubility and permeability. Its presence in the given molecule suggests that it may enhance permeability through its ability to form hydrogen bonds and interact with the membrane.

5. **Phenyl Groups**: The phenyl groups attached to the piperazine ring increase the hydrophobic character of the molecule, which can enhance permeability through lipid-rich environments. However, their size and aromatic nature may also introduce steric hindrance.

6. **Carboxylate Ester Groups**: The ester groups in the molecule can influence its solubility and permeability. Esters are generally more lipophilic than carboxylic acids, which can enhance membrane permeability. However, they may also be susceptible to hydrolysis, which could affect the molecule's stability in the assay.

Overall, the given molecule's structure suggests that it has a balance of lipophilic and polar features, which could result in moderate permeability in the PAMPA assay. The presence of the dihydropyridine core, dimethyl groups, and piperazine ring likely contribute to its ability to permeate the artificial membrane, while the nitrophenyl and phenyl groups may introduce some steric hindrance. The ester groups could also play a role in its permeability and stability.

Final answer: Low-to-moderate permeability.

------
# 278

**SMILES:** C1=CC=C2C(=C1)/C(=C/C3=CC=CN3)/C(=O)N2

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a complex organic compound that features a pyrrole ring and an indole moiety. The indole structure is a bicyclic system consisting of a benzene ring fused to a pyrrole ring, which is a common motif in many biologically active compounds. The presence of the indole structure often contributes to the molecule's ability to interact with biological targets, such as proteins and enzymes, due to its planar structure and ability to participate in π-π stacking interactions.

The pyrrole ring in the given molecule is a five-membered heterocycle containing a nitrogen atom. This ring is known for its electron-rich nature, which can enhance the molecule's ability to participate in hydrogen bonding and other non-covalent interactions.

The methylene bridge connecting the pyrrole and indole rings introduces a degree of rigidity and planarity to the molecule, which can influence its overall shape and how it fits into biological membranes or binding sites.

In the context of the Parallel Artificial Membrane Permeability Assay (PAMPA), the given molecule's structure suggests that it may have moderate permeability. The indole moiety can facilitate passage through the membrane due to its planar and lipophilic nature, but the presence of the pyrrole ring and the methylene bridge may introduce some steric hindrance or additional polar interactions that could limit its permeability. Overall, the balance of these structural features likely results in a moderate permeability profile, making it neither highly permeable nor completely impermeable to the artificial membrane.

Final answer: Low-to-moderate permeability.

------
# 279

**SMILES:** CC1=NN(C2=C1C(=CC(=O)N2)C(F)(F)F)CCC3=NC(=CS3)C4=CC=C(C=C4)OC

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound with several functional groups and structural features that influence its permeability in the PAMPA assay. Let's break down these features and their potential impact on permeability:

1. **Trifluoromethyl Group**: The presence of a trifluoromethyl group is known to increase the lipophilicity of a molecule. This group can enhance the molecule's ability to traverse lipid membranes, suggesting that the given molecule may have high permeability due to its increased hydrophobic character.

2. **Methoxyphenyl Group**: The methoxyphenyl moiety contributes to the overall lipophilicity of the molecule. The methoxy group can also participate in hydrogen bonding, which might affect the molecule's interaction with the artificial membrane. This group can enhance the molecule's ability to permeate the membrane, but its effect is balanced by the overall structure.

3. **Thiazolopyrazinone Core**: This bicyclic structure is relatively rigid and can influence the molecule's overall shape and electronic properties. The presence of nitrogen and sulfur atoms in the heterocyclic rings can contribute to polar interactions with the membrane, potentially affecting permeability. The rigidity of the core structure might also influence the molecule's ability to fit into the membrane pores, impacting its permeability.

4. **Methyl Group**: The methyl group is a small, non-polar substituent that can slightly increase the lipophilicity of the molecule. While it has a minimal impact on permeability, it can contribute to the overall hydrophobic character of the molecule.

Overall, the given molecule's combination of lipophilic groups and a rigid heterocyclic core suggests that it may have high permeability in the PAMPA assay. The trifluoromethyl and methoxyphenyl groups enhance lipophilicity, while the thiazolopyrazinone core provides structural stability and potential for polar interactions. These features collectively suggest that the molecule can effectively permeate the artificial membrane.

Final answer: High permeability.

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# 280

**SMILES:** CC1=CC=C(C=C1)S(=O)(=O)NC2=C(C=CN=C2)C(=O)NC3=NC(=CS3)C4CCC4

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a sulfonamide, which is a class of compounds known for their antimicrobial properties. The sulfonamide group is characterized by the presence of a sulfonyl functional group attached to an amine. This group is known to enhance the molecule's ability to interact with biological targets, often through hydrogen bonding and ionic interactions.

In the given molecule, the sulfonamide group is attached to a benzene ring, which is further substituted with a methyl group. This aromatic structure can contribute to the molecule's lipophilicity, potentially enhancing its ability to permeate lipid membranes.

The molecule also contains a thiazole ring, which is a five-membered heterocyclic compound containing both sulfur and nitrogen. Thiazole rings are often found in bioactive molecules and can contribute to the molecule's overall stability and ability to interact with biological targets.

Additionally, the molecule features a pyridine ring, which is a six-membered aromatic ring containing nitrogen. Pyridine rings are known for their ability to participate in hydrogen bonding and π-π interactions, which can further enhance the molecule's binding affinity to biological targets.

The cyclopentyl group attached to the thiazole ring introduces a non-polar, hydrophobic moiety, which can influence the molecule's overall solubility and permeability. This group may enhance the molecule's ability to traverse lipid membranes by increasing its hydrophobic character.

Overall, the combination of these functional groups and structural features suggests that the given molecule may exhibit moderate to high permeability in the PAMPA assay, as it possesses both hydrophilic and hydrophobic characteristics that facilitate interaction with the artificial membrane.

Final answer: High permeability

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# 281

**SMILES:** CC1=C(C(=CC=C1)C)N[S+](=O)(C2=CC=CC(=C2)NC(=O)C3=C(C(=C(N3)C)C(=O)C)C)[O-]

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several functional groups and structural elements that influence its permeability in the PAMPA assay. Let's break down these features and their implications:

1. **Aromatic Rings**: The molecule contains multiple aromatic rings, including a phenyl group and a pyrrole ring. Aromatic rings are generally hydrophobic, which can enhance the molecule's ability to interact with the hydrophobic regions of the artificial membrane. This can contribute to higher permeability.

2. **Acetyl Groups**: The presence of acetyl groups on both the phenyl ring and the pyrrole ring introduces polar characteristics to the molecule. These groups can form hydrogen bonds with the membrane, potentially increasing the molecule's solubility and permeability.

3. **Sulfonamide Group**: The sulfonamide linkage is a key feature in the molecule. Sulfonamides are known for their ability to form strong hydrogen bonds, which can enhance the molecule's interaction with the membrane. This group can also contribute to the overall polarity of the molecule, potentially improving its permeability.

4. **Dimethylpyrrole Moiety**: The dimethyl substitution on the pyrrole ring increases the hydrophobic character of this part of the molecule. This can enhance the molecule's ability to traverse the hydrophobic regions of the membrane, contributing to its permeability.

5. **Carboxamide Group**: The carboxamide group is another polar functional group that can participate in hydrogen bonding. This group can enhance the molecule's solubility in aqueous environments, which is beneficial for permeability in the PAMPA assay.

Overall, the given molecule exhibits a balance of hydrophobic and hydrophilic characteristics due to its aromatic rings, acetyl groups, sulfonamide linkage, and carboxamide group. These features suggest that the molecule would have high permeability in the PAMPA assay, as it can effectively interact with both the hydrophobic and hydrophilic components of the artificial membrane.

Final answer: High permeability.

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# 282

**SMILES:** CC1=C(NC(=C1C(=O)C)C)C(=O)NC2=CC(=CC=C2)S(=O)(=O)NC3=CC=CC=C3OC

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several functional groups and structural elements that influence its permeability in the PAMPA assay. Let's break down the key components and their impact on permeability:

1. **Pyrrole Ring**: The presence of a pyrrole ring, which is a five-membered aromatic heterocycle containing nitrogen, contributes to the molecule's aromaticity and potential for hydrogen bonding. This can enhance the molecule's ability to interact with the artificial membrane, potentially increasing its permeability.

2. **Acetyl Group**: The acetyl group attached to the pyrrole ring introduces a polar carbonyl group, which can form hydrogen bonds with the membrane. This can increase the molecule's solubility in the membrane environment, potentially enhancing its permeability.

3. **Methoxyphenyl Group**: The methoxy group on the phenyl ring is an electron-donating group that can increase the electron density of the aromatic ring. This can enhance the molecule's ability to interact with the membrane through π-π interactions, potentially increasing permeability.

4. **Sulfamoyl Group**: The sulfamoyl group is a polar, hydrophilic moiety that can form hydrogen bonds and ionic interactions with the membrane. This group can increase the molecule's solubility in aqueous environments, which is beneficial for permeability.

5. **Carboxamide Group**: The carboxamide group is another polar functional group that can participate in hydrogen bonding. This group can enhance the molecule's solubility and interaction with the membrane, potentially increasing permeability.

Overall, the given molecule contains several polar and aromatic groups that can interact with the artificial membrane through hydrogen bonding, π-π interactions, and other non-covalent interactions. These features suggest that the molecule would have high permeability in the PAMPA assay, as it can effectively interact with and traverse the membrane.

Final answer: High permeability.

------
# 283

**SMILES:** C1CC2=C(C(N=C(N2)NC3=NC4=C(O3)C(=CC=C4)Cl)C5=C(C=NN5)Cl)C(=O)C1

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several distinct structural components, each contributing to its permeability characteristics in the PAMPA assay.

1. **Quinazoline Core**: The quinazoline moiety is a bicyclic structure that is known for its planar aromatic nature. This planarity can facilitate interactions with the artificial membrane, potentially enhancing permeability. The presence of a chlorine atom on the quinazoline ring can increase lipophilicity, which often correlates with improved membrane permeability.

2. **Benzoxazole Ring**: The benzoxazole group is another aromatic system that can contribute to the molecule's overall lipophilicity. The oxygen and nitrogen atoms in the benzoxazole ring can participate in hydrogen bonding, which may influence the molecule's interaction with the membrane and its overall permeability.

3. **Pyrimidine Ring**: The pyrimidine ring is a heterocyclic aromatic compound that can also contribute to the molecule's lipophilicity. The presence of an amino group attached to the pyrimidine ring can introduce potential sites for hydrogen bonding, which may affect the molecule's solubility and permeability.

4. **Tetrahydroquinazoline Component**: The partially saturated tetrahydroquinazoline portion of the molecule introduces flexibility and a non-planar character to the structure. This flexibility can impact how the molecule fits into the membrane, potentially affecting its permeability.

Overall, the given molecule's combination of aromatic and heterocyclic rings, along with the presence of functional groups like chlorine and amino groups, suggests that it may exhibit moderate to high permeability in the PAMPA assay. The balance of lipophilic and polar characteristics allows the molecule to interact favorably with the artificial membrane, facilitating its passage through the membrane.

Final answer: High permeability

------
# 284

**SMILES:** COC1=CC=CC=C1C2=NC3=CC=CC=C3C(=N2)NCC4=CC=C(C=C4)C5=CN=CC=C5

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a quinazoline derivative, which is a class of compounds known for their diverse biological activities. The structure of the given molecule includes several key features that influence its permeability:

1. **Quinazoline Core**: The quinazoline moiety is a bicyclic structure that contributes to the molecule's planarity and rigidity. This core is often associated with good membrane permeability due to its ability to interact with lipid bilayers, enhancing the molecule's ability to traverse biological membranes.

2. **Pyridine Ring**: The presence of a pyridine ring, which is a nitrogen-containing heterocycle, can increase the molecule's polarity. This can affect its solubility and permeability, as polar molecules may have different permeability characteristics compared to non-polar ones. The pyridine ring can also participate in hydrogen bonding, which may influence the molecule's interaction with the artificial membrane.

3. **Methoxyphenyl Group**: The methoxy group attached to the phenyl ring introduces an electron-donating effect, which can affect the electronic properties of the molecule. This group can also enhance the molecule's lipophilicity, potentially improving its ability to permeate lipid membranes.

4. **Phenylpyridine Linkage**: The linkage of a phenyl group to a pyridine ring can contribute to the overall hydrophobic character of the molecule. This can facilitate interactions with the hydrophobic regions of the artificial membrane, promoting permeability.

Overall, the combination of these structural features suggests that the given molecule is likely to exhibit high permeability in the PAMPA assay. The quinazoline core, along with the methoxyphenyl and pyridine groups, contribute to a balance of hydrophobic and polar characteristics that favor membrane permeability.

Final answer: High permeability

------
# 285

**SMILES:** CNC1(CCCCC1=O)C2=CC=CC=C2Cl

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a member of the arylcyclohexylketones class, which is characterized by a cyclohexanone core structure with an aryl group attached. In this case, the aryl group is a 2-chlorophenyl moiety, which is a phenyl ring substituted with a chlorine atom. This substitution can influence the molecule's lipophilicity and electronic properties, potentially affecting its permeability.

The cyclohexanone core is a six-membered ring with a ketone functional group. This structure is relatively non-polar, which can enhance the molecule's ability to traverse lipid membranes. The presence of the ketone group can also participate in hydrogen bonding, which may affect the molecule's interaction with the artificial membrane.

The 2-(methylamino) substituent introduces a basic nitrogen atom, which can be protonated under physiological conditions, potentially increasing the molecule's solubility in aqueous environments. This functional group can also engage in hydrogen bonding and ionic interactions, which may influence the molecule's permeability by affecting its interaction with the membrane.

Overall, the combination of the aryl group, cyclohexanone core, and methylamino substituent suggests that the given molecule may exhibit moderate permeability in the PAMPA assay. The balance of lipophilic and polar characteristics allows it to interact with the artificial membrane, but the specific permeability will depend on the exact nature of these interactions.

Final answer: Low-to-moderate permeability.

------
# 286

**SMILES:** CCC(=O)NC(C1=CC=C(C=C1)OC)C2=CC(=C3C=CC=NC3=C2O)Cl

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a hydroxypyridinone derivative, which is a class of compounds known for their ability to chelate metal ions. The presence of the hydroxyl group on the quinoline ring contributes to its potential for hydrogen bonding, which can influence its solubility and permeability. 

The methoxyphenyl group attached to the molecule introduces a degree of lipophilicity, which can enhance the molecule's ability to traverse lipid membranes. However, the presence of the chloro substituent on the quinoline ring may affect the molecule's overall polarity and electronic distribution, potentially impacting its permeability.

In the context of the Parallel Artificial Membrane Permeability Assay (PAMPA), the artificial membrane mimics biological membranes, and the molecule's permeability is determined by its ability to diffuse through this membrane. The balance of hydrophilic and lipophilic properties, along with the electronic characteristics of the substituents, will dictate the molecule's permeability.

Given the structural features of the given molecule, it is likely to exhibit moderate permeability due to the presence of both hydrophilic and lipophilic groups, as well as the potential for specific interactions with the membrane. However, the exact permeability would depend on the specific conditions of the PAMPA assay and the nature of the artificial membrane used.

Final answer: Low-to-moderate permeability.

------
# 287

**SMILES:** CN1C=C(C2=CC=CC=C21)C3=C(C(=O)NC3=O)C4=CN(C5=CC=CC=C54)CCCSC(=N)N

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several distinct structural components, each contributing to its permeability characteristics in the PAMPA assay.

1. **Indole Moieties**: The molecule contains two indole groups. Indoles are aromatic heterocycles that are known for their planar structure and ability to participate in π-π stacking interactions. These interactions can enhance the molecule's ability to permeate through the artificial membrane by facilitating interactions with the membrane's aromatic residues or other planar structures.

2. **Diketone Functionality**: The presence of two carbonyl groups (dioxo) in the indole rings introduces polar characteristics to the molecule. These carbonyl groups can form hydrogen bonds with the membrane, potentially increasing the molecule's affinity for the membrane and enhancing its permeability.

3. **Imidazolidine Ring**: The imidazolidine moiety is a five-membered ring containing nitrogen atoms, which can contribute to the molecule's basicity and ability to form hydrogen bonds. This ring can interact with the membrane through hydrogen bonding or ionic interactions, which may facilitate permeation.

4. **Propyl Linker**: The propyl chain acts as a flexible linker between the imidazolidine and the indole groups. This flexibility allows the molecule to adopt conformations that may optimize its interaction with the membrane, potentially enhancing permeability.

5. **Carbamimidothioate Group**: This functional group introduces additional polar characteristics and potential sites for hydrogen bonding. The presence of sulfur in the carbamimidothioate group can also contribute to the molecule's overall lipophilicity, which may affect its permeability by balancing hydrophilic and lipophilic interactions with the membrane.

Overall, the given molecule's combination of aromatic, polar, and flexible structural features suggests that it would exhibit high permeability in the PAMPA assay. The indole groups provide aromatic interactions, while the polar functional groups and flexible linkers allow for hydrogen bonding and conformational adaptability, enhancing its ability to permeate the artificial membrane.

Final answer: High permeability

------
# 288

**SMILES:** CC(=O)C1=CC=C(C=C1)C2=CSC(=N2)N3CCC(CC3)C(=O)N

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a piperidinecarboxamide, which is a type of compound that includes a piperidine ring attached to a carboxamide group. The piperidine ring is a six-membered ring containing one nitrogen atom, which is known for its basicity and ability to participate in hydrogen bonding. This can influence the molecule's solubility and permeability.

The molecule also contains a thiazole ring, which is a five-membered ring with both sulfur and nitrogen atoms. Thiazole rings are often found in bioactive compounds and can contribute to the molecule's ability to interact with biological targets through hydrogen bonding and π-π interactions.

Additionally, the presence of an acetyl group attached to a phenyl ring introduces a degree of lipophilicity to the molecule. This can enhance the molecule's ability to permeate lipid membranes, as the acetyl group can interact with the hydrophobic regions of the membrane.

Overall, the combination of the piperidine ring, thiazole ring, and acetyl group suggests that the given molecule may have moderate permeability through the artificial membrane, as it possesses both hydrophilic and lipophilic characteristics. The piperidine and thiazole rings can facilitate interactions with the membrane, while the acetyl group can enhance lipid solubility.

Final answer: Low-to-moderate permeability.

------
# 289

**SMILES:** CC1=CC=CC=C1N[S+](=O)(C2=CC=CC(=C2)NC(=O)C3=C(C(=C(N3)C)C(=O)C)C)[O-]

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is an aromatic amide, which suggests that it contains an amide functional group attached to an aromatic ring. This structural feature is significant in determining the molecule's permeability.

The presence of the aromatic amide group indicates that the molecule has a planar structure, which can facilitate interactions with the artificial membrane. Aromatic rings are known for their ability to participate in π-π interactions, which can enhance the molecule's ability to permeate through the membrane.

Additionally, the molecule contains a pyrrole ring, which is a five-membered heterocyclic aromatic ring. The pyrrole ring contributes to the overall aromaticity and stability of the molecule, potentially aiding in its permeability.

The acetyl groups attached to the pyrrole and phenyl rings introduce hydrophobic characteristics, which can enhance the molecule's ability to traverse lipid membranes. These groups can also increase the molecule's lipophilicity, which is often associated with higher permeability.

The sulfamoyl group attached to the phenyl ring introduces a polar character, which can influence the molecule's solubility and permeability. This group can form hydrogen bonds with the membrane, potentially aiding in the molecule's permeation.

Overall, the combination of aromaticity, hydrophobic acetyl groups, and polar sulfamoyl group suggests that the given molecule likely exhibits high permeability in the artificial membrane, as these features facilitate interactions with the membrane and enhance its ability to permeate.

Final answer: High permeability.

------
# 290

**SMILES:** C[C@H]1CN(C[C@@H]1C2=NC(=NO2)C3=CN=CC=C3)C(=O)C4=NN(C5=CC=CC=C54)C

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that includes several distinct functional groups and structural features, which contribute to its permeability characteristics in the PAMPA assay.

1. **Indazole Moiety**: The presence of the indazole ring, which is a bicyclic structure consisting of a benzene ring fused to a pyrazole ring, contributes to the molecule's aromaticity and planarity. This can enhance the molecule's ability to interact with the artificial membrane through π-π stacking interactions, potentially increasing its permeability.

2. **Pyridine Rings**: The molecule contains two pyridine rings, which are six-membered aromatic rings with a nitrogen atom. These rings can also participate in π-π stacking and hydrogen bonding interactions, which may further facilitate the molecule's passage through the membrane.

3. **Pyrrolidine Ring**: The pyrrolidine ring is a five-membered nitrogen-containing heterocycle. This ring is relatively flexible and can adopt different conformations, which may allow the molecule to better fit into the membrane's structure, enhancing its permeability.

4. **Methyl Substituents**: The presence of methyl groups on the pyrrolidine ring can increase the lipophilicity of the molecule, which is often associated with improved membrane permeability. These groups can also influence the steric properties of the molecule, potentially affecting its ability to pass through the membrane.

5. **Carbonyl Group**: The carbonyl group (methanone) in the molecule can participate in hydrogen bonding and dipole-dipole interactions, which may facilitate the molecule's interaction with the membrane and its permeation.

Overall, the combination of aromatic rings, heterocycles, and lipophilic substituents in the given molecule suggests that it may have a high permeability in the PAMPA assay. The balance of hydrophilic and hydrophobic interactions, along with the structural flexibility, likely allows the molecule to effectively traverse the artificial membrane.

Final answer: High permeability

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# 291

**SMILES:** CCCCOC1=CC=C(C=C1)CNC(=O)C2=NN3CCCN(C(=O)C3=C2)CC4=CC=C(C=C4)C

**Label:** 0

**Predi:** 1

**Correct:** 0

# Response:
The given molecule is a complex organic compound that features several distinct structural components, each contributing to its permeability characteristics in the PAMPA assay.

1. **Pyrazolopyridazine Core**: The central structure of the given molecule is a pyrazolopyridazine ring system. This bicyclic framework is known for its rigidity and planarity, which can enhance the molecule's ability to interact with the artificial membrane. The presence of nitrogen atoms in the heterocyclic rings can also facilitate hydrogen bonding and dipole interactions with the membrane, potentially increasing permeability.

2. **Carboxamide Group**: The carboxamide functional group is a polar moiety that can form hydrogen bonds with the artificial membrane. This interaction can enhance the molecule's solubility and permeability, as it allows the molecule to better orient itself and interact with the membrane.

3. **Substituted Phenyl Groups**: The given molecule contains two phenyl groups, one of which is substituted with a butoxy group and the other with a methyl group. These aromatic rings can engage in π-π interactions with the membrane, which may contribute to the molecule's permeability. The butoxy group adds a hydrophobic character, which can influence the balance between hydrophilic and hydrophobic interactions with the membrane, potentially enhancing permeability.

4. **Methyl and Butoxy Substituents**: The methyl group on one phenyl ring and the butoxy group on the other can increase the lipophilicity of the molecule. This increased lipophilicity can enhance the molecule's ability to traverse the lipid-like artificial membrane, promoting permeability.

Overall, the combination of these structural features suggests that the given molecule is likely to exhibit high permeability in the PAMPA assay. The balance of polar and non-polar groups, along with the rigid and planar heterocyclic core, supports effective interaction with the artificial membrane, facilitating passage through it.

Final answer: High permeability

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# 292

**SMILES:** COC1=CC(=CC(=C1OC)OC)C(=O)N2CCN(CC2)C3=C(C=CC(=C3)Cl)Cl

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several functional groups and structural elements that influence its permeability in the PAMPA assay. Let's break down the key components and their impact on permeability:

1. **Piperazine Ring**: The presence of a piperazine ring, which is a six-membered heterocyclic structure containing two nitrogen atoms, is a common feature in many pharmaceuticals. This ring is known for its ability to enhance the solubility and permeability of molecules. The nitrogen atoms can participate in hydrogen bonding, which can facilitate the interaction of the molecule with the artificial membrane.

2. **Chlorophenyl Group**: The chlorophenyl group, which is a phenyl ring substituted with a chlorine atom, contributes to the lipophilicity of the molecule. The chlorine atom can enhance the molecule's ability to penetrate lipid membranes due to its electron-withdrawing properties, which can increase the overall hydrophobic character of the molecule.

3. **Trimethoxyphenyl Group**: The trimethoxyphenyl group, which is a phenyl ring substituted with three methoxy groups, adds to the lipophilicity and steric bulk of the molecule. Methoxy groups can increase the molecule's solubility in organic solvents and may also enhance membrane permeability by increasing the molecule's ability to interact with lipid bilayers.

4. **Methanone Linkage**: The methanone linkage (a carbonyl group) between the piperazine and the phenyl rings can act as a hydrogen bond acceptor. This functional group can participate in polar interactions with the artificial membrane, potentially aiding in the molecule's permeability.

Overall, the given molecule's structure suggests that it has a balance of hydrophilic and lipophilic properties, which is typical for molecules with moderate to high permeability in PAMPA assays. The piperazine ring and the presence of methoxy and chloro substituents likely contribute to its ability to traverse the artificial membrane, making it suitable for further evaluation in drug discovery processes.

Final answer: High permeability

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# 293

**SMILES:** COC1=CC=CC(=C1)NC2=NC(=NC3=CC=CC=C32)C4=CC=NC=C4

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a quinazoline derivative, which is a class of compounds known for their potential biological activity, including as kinase inhibitors. The structure of the given molecule includes a quinazoline core, which is a bicyclic compound consisting of a benzene ring fused to a pyrimidine ring. This core is known for its planar structure, which can facilitate interactions with biological targets.

The molecule also contains a pyridinyl group attached to the quinazoline core. Pyridine rings are aromatic and can participate in π-π stacking interactions, which may enhance the molecule's ability to interact with aromatic amino acids in protein binding sites.

Additionally, the molecule has a methoxyphenyl group attached to the nitrogen atom of the quinazoline. The methoxy group is an electron-donating group, which can influence the electronic properties of the phenyl ring, potentially affecting the molecule's overall polarity and solubility. The presence of the methoxy group can also enhance the molecule's ability to form hydrogen bonds, which may improve its binding affinity to biological targets.

In the context of the Parallel Artificial Membrane Permeability Assay (PAMPA), the given molecule's permeability is influenced by its overall lipophilicity, molecular size, and the presence of functional groups that can interact with the artificial membrane. The quinazoline core and pyridinyl group contribute to the molecule's lipophilicity, which can enhance its permeability through the lipid-like membrane. However, the methoxyphenyl group may introduce some polarity, which could moderate the overall permeability by reducing lipophilicity.

Overall, the given molecule is likely to exhibit moderate permeability in the PAMPA assay, balancing its lipophilic and polar characteristics. This balance is crucial for its potential as a bioactive compound, as it needs to traverse biological membranes to reach its target sites.

Final answer: Low-to-moderate permeability.

------
# 294

**SMILES:** CC1=NC=C(C=C1)C2=CC=C(C=C2)CNC3=NC(=NC=C3C)C4=CC=CC=C4C(C)C

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several aromatic rings and heterocyclic structures, which are key to its permeability characteristics. The molecule contains a pyrimidine core, which is a nitrogen-containing heterocycle. This core is known for its ability to participate in hydrogen bonding and π-π stacking interactions, which can enhance the molecule's ability to interact with biological membranes.

Additionally, the molecule has a pyridine ring, which is another nitrogen-containing aromatic ring. The presence of nitrogen atoms in these rings can increase the molecule's polarity, potentially improving its solubility in aqueous environments and facilitating its passage through lipid membranes.

The molecule also includes a phenyl group with a methyl substituent, as well as a propan-2-yl group attached to another phenyl ring. These hydrophobic groups can enhance the molecule's lipophilicity, which is often associated with increased membrane permeability. However, the balance between hydrophilic and hydrophobic properties is crucial in determining the overall permeability.

In the context of the Parallel Artificial Membrane Permeability Assay (PAMPA), the given molecule's structure suggests that it may exhibit moderate to high permeability. The presence of multiple aromatic rings and heterocycles indicates potential for strong interactions with the artificial membrane, while the balance of hydrophilic and hydrophobic groups suggests a favorable balance for permeability. Therefore, the given molecule is likely to have high permeability in the PAMPA assay.

Final answer: High permeability

------
# 295

**SMILES:** CCOC(=O)C1=CC=C(C=C1)NC(=O)CSC2=NC3=C(C=C2C#N)N4CCC3CC4

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a complex organic compound with several functional groups and structural features that influence its permeability in the PAMPA assay. Let's break down the key components and their impact on permeability:

1. **Amide Group**: The presence of the amide linkage, specifically the cyanoacetyl group attached to the amino group, contributes to the molecule's polarity. Amides are generally polar, which can enhance the molecule's solubility in aqueous environments, potentially increasing its permeability through the artificial membrane.

2. **Quinoxaline Ring System**: The quinoxaline moiety is a bicyclic aromatic system that can contribute to the molecule's rigidity and planarity. Aromatic systems often enhance lipophilicity, which can facilitate membrane permeability. However, the presence of the tetrahydro component suggests partial saturation, which may reduce the overall aromatic character and influence permeability accordingly.

3. **Sulfanyl Group**: The sulfanyl (thioether) linkage connects the quinoxaline moiety to the benzoate ester. Thioethers are generally non-polar and can enhance lipophilicity, which may aid in membrane permeability. However, the presence of sulfur can also introduce some degree of polarity.

4. **Benzoate Ester**: The ester group is a key feature in the molecule, contributing to its overall polarity and solubility. Esters are often involved in hydrolysis reactions, but in the context of PAMPA, they can enhance permeability due to their ability to interact with the membrane.

5. **Ethyl Ester Moiety**: The ethyl group attached to the ester increases the hydrophobic character of the molecule, which can enhance lipophilicity and, consequently, permeability.

Overall, the given molecule exhibits a balance of polar and non-polar characteristics. The presence of aromatic and partially saturated rings, along with polar functional groups like amides and esters, suggests that the molecule may have moderate permeability in the PAMPA assay. The combination of these features allows the molecule to interact with both hydrophilic and hydrophobic environments, facilitating its passage through the artificial membrane.

Final answer: Low-to-moderate permeability.

------
# 296

**SMILES:** CC(C1=CC=CC=C1)NC2=C(N=C(O2)C3=CC=C(O3)COC4=CC=C(C=C4)OC)C#N

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a complex organic compound with several functional groups and structural features that influence its permeability in the PAMPA assay. Let's break down these features and their potential impact on permeability:

1. **1,3-Oxazole Ring**: The presence of the 1,3-oxazole ring is a key structural feature. This heterocyclic aromatic ring is relatively planar and can participate in π-π stacking interactions. However, the oxazole ring itself is not particularly polar, which might limit its interaction with the polar headgroups of the artificial membrane. This could result in moderate permeability.

2. **Furan Ring**: The furan ring is another heterocyclic aromatic component. Like the oxazole, it is planar and can engage in π-π interactions. However, furan is more polar than benzene, which might enhance its interaction with the membrane. This could contribute to moderate permeability.

3. **Phenylmethoxyphenyl Group**: This group introduces a bulky aromatic moiety, which can enhance hydrophobic interactions with the membrane. The methoxy group adds some polarity, which might help in interacting with the membrane's polar headgroups. Overall, this group can contribute to moderate permeability due to its balance of hydrophobic and polar characteristics.

4. **Amino Group**: The anilino group (attached to the furan ring) introduces a basic nitrogen, which can form hydrogen bonds with the membrane. This can enhance permeability by facilitating interactions with the membrane's polar headgroups.

5. **Carbonitrile Group**: The nitrile group is a polar functional group that can engage in dipole-dipole interactions. This can enhance the molecule's ability to interact with the polar headgroups of the membrane, potentially increasing permeability.

Overall, the given molecule has a combination of aromatic and polar features that suggest moderate permeability. The aromatic rings provide hydrophobic interactions, while the polar functional groups (amino, nitrile, and methoxy) enhance interactions with the polar headgroups of the artificial membrane. The balance of these features likely results in a moderate permeability profile.

Final answer: Low-to-moderate permeability.

------
# 297

**SMILES:** CCC(C(=O)NC1=CC=C(C=C1)F)SC2=NC3=CC=CC=C3C4=NC(=NN42)CCC5=C(NN=C5C)C

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several distinct structural components, each contributing to its permeability characteristics in the PAMPA assay.

1. **Triazoloquinazoline Core**: The presence of a triazoloquinazoline moiety is significant. Quinazolines are known for their planar aromatic structure, which can facilitate interactions with the artificial membrane. The triazole ring, being a heterocyclic compound, can enhance the molecule's ability to form hydrogen bonds and π-π interactions with the membrane, potentially increasing permeability.

2. **Fluorophenyl Group**: The 4-fluorophenyl group introduces a fluorine atom, which can influence the molecule's lipophilicity and electronic properties. Fluorine is highly electronegative, which can enhance the molecule's ability to penetrate lipid membranes by increasing its overall hydrophobic character. Additionally, the presence of the fluorine atom can improve metabolic stability, which may indirectly affect permeability by prolonging the molecule's presence in the system.

3. **Thioether Linkage**: The thioether linkage (sulfanyl group) connecting the triazoloquinazoline core to the butanamide moiety can influence the molecule's flexibility and conformation. Sulfur atoms can participate in polar interactions, which may aid in the molecule's interaction with the membrane.

4. **Butanamide Moiety**: The butanamide group provides a polar amide linkage, which can form hydrogen bonds with the artificial membrane. This feature can enhance the molecule's solubility and interaction with the membrane, potentially increasing permeability.

5. **Dimethylpyrazole Group**: The dimethylpyrazole group contributes additional aromaticity and potential for hydrogen bonding. The methyl groups increase the molecule's hydrophobic character, which can enhance membrane permeability by increasing lipophilicity.

Overall, the given molecule's combination of aromatic rings, heteroatoms, and functional groups suggests that it has a balance of hydrophobic and hydrophilic properties, which is conducive to moderate to high permeability in the PAMPA assay. The presence of fluorine and heteroatoms like nitrogen and sulfur further supports its potential for effective interaction with the artificial membrane, enhancing its permeability.

Final answer: High permeability

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# 298

**SMILES:** C1=CC=C2C(=C1)C3=C(C2=O)C(SC4=CC=CC=C4N3)C5=CC=CO5

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several distinct structural components, each contributing to its permeability characteristics in the PAMPA assay.

Firstly, the molecule contains a benzothiophene moiety. Benzothiophene is a bicyclic structure consisting of a benzene ring fused to a thiophene ring. This structure is known for its aromaticity, which can enhance the molecule's lipophilicity. Lipophilicity is a key factor in determining the permeability of a molecule through lipid membranes, such as those found in biological systems. The presence of the benzothiophene moiety suggests that the given molecule may have a degree of hydrophobic character, which can facilitate its passage through the lipid layers of the artificial membrane.

Additionally, the molecule includes a furan ring. Furan is a five-membered aromatic ring containing an oxygen atom. While furan is less lipophilic than benzene, its aromatic nature can still contribute to the overall stability and planarity of the molecule. The presence of the furan ring may also influence the electronic distribution within the molecule, potentially affecting its interaction with the artificial membrane.

The spiro connection between the benzothiophene and the indole moiety introduces a unique three-dimensional structure. Spiro compounds are known for their rigidity and can impact the overall shape and conformation of the molecule. This structural feature may affect how the molecule fits into the membrane, potentially influencing its permeability.

The indole moiety is a bicyclic structure consisting of a benzene ring fused to a pyrrole ring. Indole is a common structural motif in many bioactive compounds and can contribute to the molecule's ability to interact with biological membranes. The presence of the indole moiety may enhance the molecule's ability to engage in π-π interactions with the membrane, further influencing its permeability.

Overall, the combination of these aromatic and spirocyclic structures suggests that the given molecule may exhibit moderate to high permeability in the PAMPA assay. The aromatic rings contribute to lipophilicity and potential membrane interactions, while the spiro connection adds structural rigidity that can affect the molecule's conformation and fit within the membrane.

Final answer: High permeability.

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# 299

**SMILES:** CC1=CC=C(C=C1)S(=O)(=O)NC2=C(C=C(C=C2)C(=O)NC3=NC(=CS3)C4=CC=CC=C4)Cl

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a sulfonamide, which is a class of compounds known for their antibacterial properties. The sulfonamide group is characterized by the presence of a sulfonyl functional group attached to an amine. In this molecule, the sulfonamide group is attached to a benzamide moiety, which is a benzene ring linked to an amide group.

The presence of the sulfonamide group suggests that the given molecule may have moderate permeability in the PAMPA assay. Sulfonamides are generally polar due to the sulfonyl group, which can form hydrogen bonds with the artificial membrane. This polarity can facilitate interactions with the membrane, potentially allowing the molecule to permeate to some extent.

Additionally, the molecule contains a thiazole ring, which is a five-membered ring containing both sulfur and nitrogen. This heterocyclic ring can contribute to the molecule's overall lipophilicity, which may enhance its ability to permeate the membrane. The presence of a chlorine atom on the phenyl ring can also increase lipophilicity, potentially aiding in membrane permeability.

However, the overall structure of the given molecule, with its multiple aromatic rings and polar functional groups, suggests that while it may have some permeability, it might not be highly permeable. The balance of polar and non-polar regions in the molecule indicates that it may have moderate permeability, with some potential for interaction with the artificial membrane but not enough to classify it as highly permeable.

Final answer: Low-to-moderate permeability.

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# 300

**SMILES:** CC[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)OC(=O)C)CCC4=C/C(=N/O)/CC[C@H]34

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a steroid, which is a class of organic compounds characterized by a specific arrangement of four cycloalkane rings that are fused together. This structural feature is crucial in determining the molecule's permeability.

In the given molecule, the steroid backbone is modified with an ethyl group and a 2-ethynyl group, which are common modifications in steroid chemistry that can influence the molecule's lipophilicity and, consequently, its permeability. The presence of these groups can enhance the molecule's ability to interact with lipid membranes, potentially increasing its permeability.

Additionally, the molecule contains a hydroxyimino group, which can form hydrogen bonds with the artificial membrane, potentially affecting its permeability. The acetate ester group in the molecule can also influence its solubility and permeability, as esters are often more lipophilic than their corresponding acids.

Overall, the combination of the steroid backbone, ethyl and ethynyl groups, and the hydroxyimino and acetate ester functionalities suggests that the given molecule may have moderate to high permeability in the PAMPA assay, as these structural features are generally associated with favorable interactions with lipid membranes.

Final answer: High permeability

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# 301

**SMILES:** CC1=C(C=CC2=C1OC(CC2)(C)C)O

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a member of the 1-benzopyrans, which are compounds characterized by a benzene ring fused to a pyran ring. This structural feature is significant in determining the molecule's permeability.

The presence of the hydroxy group (OH) on the benzopyran structure contributes to the molecule's polarity and potential for hydrogen bonding. This functional group can enhance the molecule's solubility in aqueous environments, which is crucial for its permeability across biological membranes.

The trimethyl substitution on the pyran ring increases the molecule's hydrophobic character. This can influence the molecule's ability to interact with the lipid components of the artificial membrane, potentially enhancing its permeability by facilitating passage through the lipid bilayer.

Overall, the balance between the hydrophilic hydroxy group and the hydrophobic trimethyl groups suggests that the given molecule may exhibit moderate permeability in the PAMPA assay. The hydroxy group can promote solubility and interaction with the aqueous environment, while the trimethyl groups can facilitate interaction with the lipid components of the membrane.

Final answer: Low-to-moderate permeability.

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# 302

**SMILES:** CCN(CC)S(=O)(=O)C1=CC=CC(=C1)C(=O)NC2=CC=C(C=C2)C#N

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a benzamide derivative, which is characterized by the presence of a benzoyl group attached to an amide linkage. This structural feature is significant in determining the molecule's permeability.

The molecule contains a diethylsulfamoyl group attached to a phenyl ring. The presence of the sulfonamide group, which is known for its polar nature, can enhance the molecule's solubility in aqueous environments. This polar group can form hydrogen bonds and ionic interactions with the artificial membrane, potentially increasing the molecule's permeability.

Additionally, the molecule has a cyano group attached to another phenyl ring. The cyano group is a polar functional group that can also participate in hydrogen bonding and dipole-dipole interactions. This can further influence the molecule's interaction with the artificial membrane, potentially enhancing its permeability.

The overall structure of the given molecule, with its combination of polar functional groups and aromatic rings, suggests that it may have moderate to high permeability in the PAMPA assay. The balance of hydrophobic aromatic rings and hydrophilic functional groups allows the molecule to interact favorably with the artificial membrane, facilitating its passage through the membrane.

Final answer: High permeability

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# 303

**SMILES:** COC(=O)CNC(=O)C1=NC(=C2N1C=CN=C2)C3=C(C=C(C=C3)Cl)Cl

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a complex organic compound that features several functional groups and structural elements that influence its permeability in the PAMPA assay. Let's break down the key components and their impact on permeability:

1. **Dichlorophenyl Group**: The presence of the dichlorophenyl moiety introduces hydrophobic characteristics to the molecule. The chlorine atoms increase the lipophilicity, which can enhance the molecule's ability to interact with the lipid components of the artificial membrane. This hydrophobic interaction often facilitates permeability through the membrane.

2. **Imidazo[1,2-a]pyridine Core**: This bicyclic structure is a heteroaromatic system that can contribute to the molecule's overall rigidity and planarity. The presence of nitrogen atoms in the imidazo-pyridine ring can also participate in hydrogen bonding or ionic interactions with the membrane, potentially aiding in permeation.

3. **Amide Linkage**: The amide group in the molecule is a polar functional group that can form hydrogen bonds with the membrane. This can enhance solubility in aqueous environments and facilitate interaction with the membrane, potentially increasing permeability.

4. **Methyl Ester Group**: The ester group is another polar moiety that can influence the molecule's solubility and permeability. Esters can undergo hydrolysis, but in the context of PAMPA, they may enhance membrane permeability by providing a balance between hydrophilicity and lipophilicity.

Overall, the given molecule's structure suggests that it has a balance of hydrophobic and hydrophilic properties, which is typical for molecules with moderate permeability in PAMPA assays. The dichlorophenyl group and imidazo-pyridine core contribute to lipophilicity and potential membrane interactions, while the amide and ester groups provide polar characteristics that can aid in solubility and permeability. Therefore, the given molecule is likely to exhibit moderate permeability in the PAMPA assay.

Final answer: Low-to-moderate permeability.

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# 304

**SMILES:** CC(C)(C)OC(=O)N1CCN(CC1)C2=CC=C(C=C2)NCC3=CC=C(O3)C4=CC=C(C=C4)C#N

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a complex organic compound that includes several functional groups and structural features that influence its permeability in the PAMPA assay. Let's break down these features and their impact on permeability:

1. **tert-Butyl Ester Group**: The presence of a tert-butyl ester group in the molecule suggests that it has a relatively large and hydrophobic moiety. This group can enhance the lipophilicity of the molecule, which often increases its ability to permeate lipid membranes. However, the ester linkage can also be a site for hydrolysis, which might affect the stability of the molecule in biological environments.

2. **Piperazine Ring**: The piperazine ring is a common structural motif in many pharmaceuticals and contributes to the molecule's basicity. This can enhance the molecule's solubility in aqueous environments and potentially improve its permeability through biological membranes. The presence of a piperazine ring can also facilitate interactions with biological targets, which is crucial for drug-like properties.

3. **Phenyl and Furan Groups**: The phenyl and furan groups contribute to the aromatic character of the molecule. Aromatic groups can enhance lipophilicity, which is beneficial for membrane permeability. However, the furan group, being an electron-rich heterocycle, might also participate in specific interactions with the artificial membrane, potentially affecting permeability.

4. **Cyano Group**: The cyano group is a polar functional group that can influence the molecule's overall polarity. While it may reduce lipophilicity, it can also form hydrogen bonds with the artificial membrane, potentially affecting permeability. The presence of this group might also impact the molecule's overall electronic properties, which can influence its interaction with the membrane.

5. **Overall Structure**: The combination of these functional groups results in a molecule with a balance of hydrophobic and hydrophilic properties. The large, lipophilic tert-butyl ester and aromatic groups suggest that the molecule may have high permeability through the artificial membrane. However, the presence of polar groups like the cyano and ester functionalities might moderate this permeability, leading to a balance that could result in low-to-moderate permeability.

In summary, the given molecule's structural features suggest that it has a balance of lipophilic and hydrophilic properties, which could result in moderate permeability through the artificial membrane used in the PAMPA assay.

Final answer: Low-to-moderate permeability.

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# 305

**SMILES:** CC1=CC=C(C=C1)N(C)S(=O)(=O)C2=CC=C(C=C2)C3=CN=C(O3)C4CC4

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a sulfonamide, which is a class of compounds known for their ability to permeate biological membranes. The sulfonamide group is a key functional group in this molecule, contributing to its permeability characteristics.

The presence of the sulfonamide group suggests that the given molecule has polar characteristics, which can enhance its solubility in aqueous environments. This group is known for its ability to form hydrogen bonds, which can facilitate interactions with the artificial membrane, potentially increasing permeability.

Additionally, the molecule contains an oxazole ring, which is a heterocyclic aromatic compound. The oxazole ring can contribute to the molecule's overall stability and rigidity, which may affect its ability to permeate the membrane. The aromatic nature of the oxazole ring can also enhance lipophilicity, which may aid in crossing lipid-rich membranes.

The cyclopropyl group is a small, non-polar moiety that can increase the lipophilicity of the molecule. This can enhance the molecule's ability to interact with the lipid components of the artificial membrane, potentially increasing permeability.

The presence of the methylphenyl group adds to the lipophilic character of the molecule, which can further enhance its ability to permeate the membrane.

Overall, the combination of polar and non-polar groups in the given molecule suggests that it may have moderate to high permeability in the artificial membrane, as it possesses both hydrophilic and lipophilic characteristics that can facilitate interaction with the membrane.

Final answer: High permeability.

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# 306

**SMILES:** CC1=CC(=C(C=C1)C)CN2CCC(CC2)CNC(=O)NC3=C(C=C(C=C3)Br)F

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a member of the piperidines, which are known for their cyclic structure containing five carbon atoms and one nitrogen atom. This piperidine ring is a common scaffold in medicinal chemistry due to its ability to enhance the pharmacokinetic properties of compounds.

The molecule features a urea linkage, which is a functional group characterized by a carbonyl group connected to two nitrogen atoms. This linkage is often involved in hydrogen bonding, which can influence the molecule's solubility and permeability.

The presence of a 2,4-dibromophenyl group introduces two bromine atoms on the phenyl ring. Bromine atoms are relatively large and electronegative, which can increase the molecule's overall molecular weight and potentially affect its lipophilicity. The dibromo substitution may also influence the molecule's electronic properties, potentially affecting its interaction with biological membranes.

Additionally, the 2-methylphenyl group contributes to the molecule's hydrophobic character. The methyl group can enhance lipophilicity, which may improve the molecule's ability to permeate lipid membranes.

Overall, the combination of the piperidine ring, urea linkage, and the brominated and methylated phenyl groups suggests that the given molecule may exhibit moderate to high permeability in the PAMPA assay. The balance of hydrophilic and hydrophobic components, along with the potential for hydrogen bonding, likely facilitates its passage through the artificial membrane.

Final answer: High permeability

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# 307

**SMILES:** CCOC(=O)C1=CC(=NC2=C1C(=NN2CCC#N)C)C3=CC=CO3

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a pyrazolopyridine derivative, which is a complex structure that includes several functional groups and aromatic systems. To determine its permeability in the PAMPA assay, we need to consider the structural features that influence its interaction with the artificial membrane.

1. **Aromatic Systems**: The molecule contains a furan ring and a pyrazolopyridine core. Aromatic systems, such as these, often contribute to the molecule's ability to interact with the membrane through π-π stacking and hydrophobic interactions. These interactions can enhance the molecule's permeability by facilitating its passage through the membrane.

2. **Ethyl Ester Group**: The presence of the ethyl ester group in the molecule can influence its lipophilicity. Esters are generally more lipophilic than their corresponding acids, which can enhance the molecule's ability to permeate lipid membranes. However, esters can also be susceptible to hydrolysis, which might affect the molecule's stability in the membrane environment.

3. **Cyano Group**: The cyano group is a polar functional group that can form hydrogen bonds with the membrane. While this might increase the molecule's affinity for the membrane, it can also decrease its overall lipophilicity, potentially limiting its permeability.

4. **Methyl Substitution**: The methyl group on the pyrazolopyridine core can increase the molecule's lipophilicity, which may enhance its permeability. However, the impact is likely to be small compared to the other functional groups.

Overall, the given molecule's structure suggests that it has a balance of hydrophobic and hydrophilic properties. The aromatic systems and ethyl ester group likely contribute to high permeability, while the cyano group may provide some polar interaction with the membrane. Therefore, the given molecule is likely to exhibit high permeability in the PAMPA assay.

Final answer: High permeability

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# 308

**SMILES:** CNC1=NC2=C(S1)C(CC(=O)N2)C3=CC=CC=C3F

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a thienopyrimidine derivative, which is characterized by a fused ring system consisting of a thiophene ring and a pyrimidine ring. This structural feature is significant in drug design due to its potential biological activity and ability to interact with various biological targets.

The presence of the fluorophenyl group attached to the thienopyrimidine core can influence the molecule's lipophilicity and electronic properties. The fluorine atom is highly electronegative, which can enhance the molecule's ability to interact with hydrophobic environments, such as lipid membranes. This can potentially increase the molecule's permeability across biological membranes.

The methylamino group contributes to the molecule's basicity and can form hydrogen bonds, which may facilitate interactions with polar environments or active sites in proteins. This functional group can also affect the solubility and distribution of the molecule in biological systems.

The thienopyrimidine core itself is a planar, aromatic system that can participate in π-π stacking interactions, which are important for binding to aromatic amino acids in proteins. This can enhance the molecule's ability to permeate through lipid bilayers, as it can interact with the lipid tails and headgroups.

Overall, the combination of these structural features suggests that the given molecule likely exhibits high permeability in the PAMPA assay, as it possesses a balance of hydrophobic and hydrophilic properties that facilitate membrane interaction and permeation.

Final answer: High permeability

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# 309

**SMILES:** C1CCN(CC1)C2=NC(=CS2)C3=CC=C(C=C3)Br

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a thiazole derivative with a piperidine ring and a bromophenyl group. The thiazole ring is a five-membered heterocyclic compound containing both sulfur and nitrogen atoms, which is known for its electron-rich nature and ability to participate in hydrogen bonding and π-π interactions. This can enhance the molecule's ability to interact with biological membranes.

The piperidine ring is a six-membered nitrogen-containing heterocycle, which is a common structural motif in many pharmaceuticals due to its basicity and ability to form hydrogen bonds. This can increase the molecule's solubility and enhance its interaction with biological targets.

The presence of the bromophenyl group introduces a lipophilic character to the molecule, which can increase its ability to permeate lipid membranes. The bromine atom can also participate in halogen bonding, which may further influence the molecule's interaction with the artificial membrane.

Overall, the combination of these structural features suggests that the given molecule is likely to have high permeability in the PAMPA assay due to its balanced hydrophilic and lipophilic properties, as well as its ability to form various non-covalent interactions with the artificial membrane.

Final answer: High permeability

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# 310

**SMILES:** C1CC2=C(C(N=C(N2)NC3=NC4=C(O3)C=CC=C4Cl)C5=C(C=NN5)Cl)C(=O)C1

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several distinct structural components, each contributing to its permeability characteristics in the PAMPA assay.

1. **Benzoxazole Moiety**: The presence of the chloro-substituted benzoxazole ring in the given molecule suggests a potential for moderate to high permeability. Benzoxazole rings are known for their planar aromatic structure, which can facilitate interactions with the artificial membrane, enhancing permeability. The chlorine atom can also influence the molecule's lipophilicity, potentially increasing its ability to traverse the membrane.

2. **Pyrimidinyl Group**: The pyrimidinyl group, which is linked to the benzoxazole ring, is a heterocyclic aromatic compound. This group can contribute to the molecule's overall aromaticity and planarity, which are favorable for permeability. The nitrogen atoms in the pyrimidine ring can participate in hydrogen bonding, which may aid in the molecule's interaction with the membrane.

3. **Benzoxazine Core**: The benzoxazine structure in the given molecule is a heterocyclic compound that can influence the molecule's flexibility and conformation. The presence of nitrogen and oxygen atoms in the benzoxazine ring can enhance the molecule's ability to form hydrogen bonds, which may facilitate its passage through the membrane.

4. **Chlorine Substitution**: The chloro group on the benzoxazole ring can increase the lipophilicity of the molecule, which is often associated with higher permeability. However, it can also introduce steric hindrance, which might slightly reduce permeability.

5. **Tetrahydro Structure**: The tetrahydro component of the benzoxazine ring indicates partial saturation, which can affect the molecule's rigidity and flexibility. This structural feature might influence the molecule's ability to fit into the membrane's pores, potentially affecting its permeability.

Overall, the combination of aromatic and heterocyclic components, along with the presence of functional groups that can engage in hydrogen bonding, suggests that the given molecule likely exhibits high permeability in the PAMPA assay. The balance of lipophilic and polar characteristics, along with the structural features that facilitate membrane interaction, supports this conclusion.

Final answer: High permeability

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# 311

**SMILES:** COC1=C(C=C(C=C1)S(=O)(=O)N2CCOCC2)NC(=O)C3=CC(=CC=C3)N4C=CC=C4

**Label:** 0

**Predi:** 1

**Correct:** 0

# Response:
The given molecule is a complex organic compound that features several functional groups and structural elements that influence its permeability in the PAMPA assay. Let's break down these features and their implications:

1. **Benzamide Core**: The presence of a benzamide moiety suggests that the molecule has a planar aromatic structure, which can facilitate interactions with the artificial membrane. Aromatic rings often enhance lipophilicity, which can improve membrane permeability.

2. **Methoxy Group**: The methoxy group attached to the aromatic ring increases the molecule's lipophilicity. This can enhance the ability of the molecule to traverse lipid membranes, contributing to higher permeability.

3. **Sulfonyl Group**: The sulfonyl group is a polar functional group that can form hydrogen bonds with the artificial membrane. While it may introduce some polarity, its presence is balanced by the lipophilic aromatic system, potentially allowing the molecule to maintain sufficient permeability.

4. **Pyrrole Ring**: The pyrrole ring is a heterocyclic aromatic compound that can contribute to the overall aromatic character of the molecule. This can enhance lipophilicity and facilitate membrane permeation.

5. **Morpholine Ring**: The morpholine ring is a heterocyclic amine that introduces polarity to the molecule. This can enhance solubility in aqueous environments, which is beneficial for interaction with the PAMPA membrane. However, its polar nature might limit the overall permeability compared to purely lipophilic compounds.

Overall, the given molecule exhibits a balance of lipophilic and polar characteristics. The aromatic and methoxy groups enhance lipophilicity, promoting membrane permeability, while the sulfonyl and morpholine groups introduce polar interactions that may moderate this effect. This balance suggests that the molecule likely exhibits high permeability in the PAMPA assay, as it can effectively interact with both the hydrophobic and hydrophilic components of the artificial membrane.

Final answer: High permeability

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# 312

**SMILES:** CC1=CC2=C(C=C1)SC3=C(C=C(C=C3)C(=O)NC4CCCC4)N=C2C

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a dibenzothiazepine, which is a tricyclic compound consisting of two benzene rings fused to a thiazepine ring. This structural framework is known for its rigidity and planarity, which can influence the molecule's ability to permeate biological membranes.

The presence of the thiazepine ring, which contains both sulfur and nitrogen, can contribute to the molecule's overall polarity and potential for hydrogen bonding. This can affect its solubility and permeability characteristics. The nitrogen atom in the thiazepine ring may also participate in interactions with the artificial membrane, potentially influencing permeability.

The methyl groups attached to the benzene rings can increase the hydrophobic character of the molecule, which may enhance its ability to interact with the lipid components of the artificial membrane. However, these groups can also create steric hindrance, potentially limiting the molecule's ability to fit into the membrane pores.

The carboxamide group at the end of the molecule introduces additional polarity and the potential for hydrogen bonding. This functional group can interact with the polar head groups of the artificial membrane, which may facilitate or hinder permeability depending on the balance between hydrophilic and hydrophobic interactions.

Overall, the given molecule's dibenzothiazepine core, combined with its specific functional groups, suggests that it may exhibit moderate permeability in the artificial membrane. The balance of hydrophobic and hydrophilic interactions, along with the structural rigidity, likely contributes to this permeability profile.

Final answer: Low-to-moderate permeability.

------
# 313

**SMILES:** C1CN(CCN1)C2=NC(=CS2)C3=CC=C(C=C3)Br

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a member of the thiazoles and contains a piperazine ring, which are both important structural features influencing its permeability.

The thiazole ring is a five-membered heterocyclic compound containing both sulfur and nitrogen atoms. This ring is known for its electron-rich nature, which can enhance the molecule's ability to interact with biological membranes. The presence of the thiazole ring often contributes to the molecule's ability to permeate lipid membranes due to its planar structure and potential for hydrogen bonding and π-π interactions.

The piperazine ring is a six-membered heterocyclic amine containing two nitrogen atoms. Piperazine rings are commonly found in pharmaceuticals and are known for their ability to enhance solubility and permeability. The nitrogen atoms in the piperazine ring can participate in hydrogen bonding, which can facilitate the molecule's interaction with the artificial membrane.

Additionally, the presence of the 4-bromophenyl group introduces a bromine atom, which can increase the molecule's lipophilicity. This can enhance the molecule's ability to permeate through the lipid-rich environment of the artificial membrane.

Overall, the combination of the thiazole and piperazine rings, along with the 4-bromophenyl group, suggests that the given molecule would exhibit high permeability in the Parallel Artificial Membrane Permeability Assay (PAMPA).

Final answer: High permeability

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# 314

**SMILES:** COC1=CC=CC=C1N2C=NC3=C2C=CC(=C3)C(=O)N4CCCCC4

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a member of the benzimidazole class, which is known for its ability to interact with various biological targets due to its aromatic and heterocyclic structure. The benzimidazole core is a bicyclic structure consisting of a benzene ring fused to an imidazole ring, which contributes to the molecule's planarity and potential for hydrogen bonding.

The presence of the methoxyphenyl group attached to the benzimidazole ring introduces additional aromaticity and potential for hydrophobic interactions. The methoxy group can also participate in hydrogen bonding due to the presence of the oxygen atom, which may enhance the molecule's solubility and interaction with polar environments.

The piperidine moiety, a six-membered nitrogen-containing ring, is known for its basicity and ability to form ionic interactions. This can increase the molecule's solubility in aqueous environments and potentially enhance its ability to cross biological membranes.

In the context of the Parallel Artificial Membrane Permeability Assay (PAMPA), the given molecule's structure suggests that it may have moderate permeability. The aromatic and heterocyclic components, such as the benzimidazole and methoxyphenyl groups, contribute to lipophilicity, which can facilitate membrane permeation. However, the presence of the piperidine ring may introduce some degree of polarity, which could limit permeability by interacting with polar sites on the membrane.

Overall, the balance of lipophilic and polar characteristics in the given molecule suggests that it may exhibit low-to-moderate permeability in the PAMPA assay, with potential for moderate interaction with the artificial membrane.

Final answer: Low-to-moderate permeability.

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# 315

**SMILES:** C1=CC2=C(C=CC(=C2N=C1)O)CNC3=C(C=C(C=C3)F)F

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a hydroxyquinoline derivative, which is characterized by the presence of a quinoline core with a hydroxyl group attached. This structure is known for its ability to chelate metal ions, which can influence its permeability properties.

The quinoline core contributes to the molecule's planar structure, which can facilitate its passage through lipid membranes due to favorable interactions with the lipid bilayer. The hydroxyl group on the quinoline ring can form hydrogen bonds with the membrane, potentially enhancing its permeability by stabilizing interactions with the membrane.

Additionally, the presence of the difluorophenyl group attached via a methylene bridge introduces fluorine atoms, which can increase the molecule's lipophilicity. Fluorine atoms are small and highly electronegative, which can enhance the molecule's ability to penetrate lipid membranes by increasing its overall hydrophobic character.

Overall, the combination of the planar quinoline structure, the hydroxyl group, and the difluorophenyl moiety suggests that the given molecule would exhibit high permeability in the PAMPA assay, as these features collectively enhance its ability to interact with and traverse the artificial membrane.

Final answer: High permeability.

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# 316

**SMILES:** CC(=O)NC1=CC=C(C=C1)OCC2=C(C=CC(=C2)C3=NC4=CC=CC=C4C(=O)N3CC5=CC=CC=C5)OC

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a member of the quinazolines, which are known for their diverse biological activities, including their role as kinase inhibitors. The structure of the given molecule includes several key features that influence its permeability:

1. **Quinazoline Core**: The quinazoline moiety is a bicyclic structure that contributes to the molecule's planarity and rigidity. This core is often associated with good membrane permeability due to its ability to interact with lipid bilayers, facilitating passive diffusion.

2. **Aromatic Rings**: The presence of multiple aromatic rings, including a benzyl group and a methoxyphenyl group, enhances the molecule's lipophilicity. Aromatic rings can participate in π-π interactions with the lipid components of the membrane, which can increase permeability.

3. **Methoxy Group**: The methoxy group attached to the phenyl ring can increase the molecule's lipophilicity, potentially enhancing its ability to traverse lipid membranes. However, it may also introduce some degree of polarity, which could affect the overall balance between hydrophilicity and lipophilicity.

4. **Acetamide Group**: The acetamide group introduces a degree of polarity to the molecule, which can affect its solubility and permeability. While it may hinder permeability due to its hydrophilic nature, it can also participate in hydrogen bonding with the membrane, potentially aiding in permeation.

5. **Phenylmethoxy Linkage**: The phenylmethoxy linkage acts as a flexible spacer that may influence the molecule's ability to fit into the membrane's lipid bilayer. This flexibility can allow the molecule to adapt its conformation to optimize interactions with the membrane.

Overall, the given molecule's combination of aromatic rings, a quinazoline core, and functional groups like methoxy and acetamide suggest that it has a balance of lipophilic and hydrophilic properties. This balance is likely to result in moderate permeability through the artificial membrane, allowing it to interact effectively with both the lipid and aqueous phases of the membrane.

Final answer: Low-to-moderate permeability.

------
# 317

**SMILES:** CC(C)OC1=CC=CC(=C1)C2=CSC(=N2)N3CCC(CC3)C(=O)N

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a piperidinecarboxamide, which is a type of compound characterized by the presence of a piperidine ring attached to a carboxamide group. This structural feature is often associated with a certain degree of lipophilicity and potential for hydrogen bonding, which can influence the molecule's permeability.

The molecule contains a thiazole ring, which is a five-membered heterocyclic compound containing both sulfur and nitrogen. Thiazole rings are known for their aromaticity and can contribute to the overall stability and electronic properties of the molecule. This aromatic ring can enhance the molecule's ability to interact with lipid membranes, potentially increasing its permeability.

Additionally, the molecule has a phenyl group substituted with an isopropoxy group. The presence of this bulky, hydrophobic group can increase the lipophilicity of the molecule, which is often associated with higher permeability through lipid membranes. The isopropoxy group can also influence the molecule's solubility and distribution within biological systems.

Overall, the combination of the piperidinecarboxamide structure, the thiazole ring, and the isopropoxy-substituted phenyl group suggests that the given molecule may exhibit high permeability through the artificial membrane due to its lipophilic and aromatic characteristics.

Final answer: High permeability.

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# 318

**SMILES:** CN1CCN(CC1)C2=CC=C(C=C2)NC3=NC=C(C(=N3)OC4=CC=CC(=C4)NC(=O)C=C)Cl

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that includes several functional groups and structural features that influence its permeability in the PAMPA assay. Let's break down these features and their impact on permeability:

1. **Aromatic Rings**: The molecule contains multiple aromatic rings, including a pyrimidine ring and phenyl rings. Aromatic rings can enhance the molecule's ability to interact with the artificial membrane through π-π stacking interactions. This can increase the molecule's permeability by facilitating its passage through the membrane.

2. **Chloro Substituent**: The presence of a chloro group on the pyrimidine ring can influence the molecule's lipophilicity. Chlorine atoms are electronegative and can increase the molecule's overall hydrophobicity, which may enhance its ability to permeate lipid membranes.

3. **Amino Linkages**: The molecule has amino groups that can form hydrogen bonds with the artificial membrane. These interactions can stabilize the molecule's orientation and facilitate its passage through the membrane. However, the presence of these groups can also introduce some degree of polarity, which might limit permeability if they are not balanced by sufficient hydrophobic interactions.

4. **Methoxy Group**: The methoxy group attached to the phenyl ring can increase the molecule's lipophilicity, which generally enhances permeability. However, it can also introduce steric hindrance, potentially limiting the molecule's ability to fit into the membrane pores.

5. **Piperazine Ring**: The piperazine moiety is a common feature in many pharmaceuticals and can influence the molecule's solubility and permeability. The presence of this ring can enhance the molecule's ability to interact with the membrane through hydrogen bonding and hydrophobic interactions, potentially increasing its permeability.

6. **Prop-2-enamide Moiety**: This functional group introduces some degree of polarity and potential for hydrogen bonding, which can affect the molecule's permeability. The balance between the polar and non-polar regions of the molecule will determine its overall permeability.

Considering these structural features, the given molecule is likely to exhibit high permeability in the PAMPA assay. The combination of aromatic rings, chloro substituents, and functional groups that promote hydrophobic interactions and hydrogen bonding suggests that the molecule can effectively traverse the artificial membrane.

Final answer: High permeability

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# 319

**SMILES:** CCCOC(=O)C1=CC=C(C=C1)OC2=C(NN=C2C3=C(C=C(C=C3)O)O)C

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a benzoate ester, which is a key structural feature influencing its permeability. The ester linkage in the molecule is formed between a benzoic acid and an alcohol, specifically a propyl group in this case. This esterification generally increases the lipophilicity of the molecule, which can enhance its ability to permeate lipid membranes.

The presence of hydroxyl groups on the phenyl rings and the pyrazole ring contributes to the molecule's polarity. These hydroxyl groups can form hydrogen bonds, which may facilitate interactions with the polar head groups of the artificial membrane. However, the overall effect of these hydroxyl groups on permeability is balanced by the lipophilic nature of the ester linkage and the aromatic rings, which tend to increase hydrophobic interactions with the membrane.

The pyrazole ring, which is a five-membered heterocyclic compound, can also play a role in the molecule's permeability. The nitrogen atom in the pyrazole ring can participate in hydrogen bonding and other polar interactions, potentially affecting the molecule's orientation and interaction with the membrane.

Overall, the balance of hydrophilic and hydrophobic interactions, along with the structural features of the ester linkage and aromatic rings, suggests that the given molecule likely exhibits moderate permeability in the artificial membrane. The ester group enhances lipophilicity, while the hydroxyl groups provide some polar interaction potential, resulting in a balance that may not be highly permeable but sufficient for the molecule to traverse the membrane.

Final answer: Low-to-moderate permeability.

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# 320

**SMILES:** C1CN(CCC1C(=O)N)C2=NC(=CS2)C3=CC=CC=C3F

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a piperidinecarboxamide, which is characterized by a piperidine ring attached to a carboxamide group. This structure is known for its potential biological activity and is often used in pharmaceuticals.

The molecule also contains a thiazole ring, which is a five-membered ring containing both sulfur and nitrogen atoms. This heterocyclic ring can contribute to the molecule's ability to interact with biological targets due to its aromatic nature and potential for hydrogen bonding.

Additionally, the presence of a fluorophenyl group introduces a fluorine atom into the phenyl ring. The fluorine atom can enhance the molecule's lipophilicity, which may improve its ability to permeate lipid membranes. Fluorine is also known to influence the electronic properties of the molecule, potentially affecting its binding affinity to biological targets.

Overall, the combination of these structural features suggests that the given molecule may have moderate permeability through the artificial membrane. The piperidine ring and thiazole ring contribute to the molecule's ability to interact with the membrane, while the fluorophenyl group may enhance its lipophilicity, aiding in permeability. However, the exact permeability would depend on the specific conditions of the PAMPA assay and the nature of the artificial membrane used.

Final answer: Low-to-moderate permeability.

------
# 321

**SMILES:** C1C(C2(CN1CC3=CC=C(C=C3)O)CN(C2)C4=CC=CC=C4)CNC5=CC=CC=C5

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex structure that includes several functional groups and structural features that influence its permeability in the PAMPA assay. Let's break down these features and their impact on permeability:

1. **Phenyl Groups**: The molecule contains multiple phenyl groups, which are aromatic rings. These rings can enhance lipophilicity, which is the ability of a molecule to dissolve in fats, oils, and lipids. Increased lipophilicity generally improves membrane permeability as it allows the molecule to interact more favorably with the lipid components of the artificial membrane.

2. **Diazaspiro Structure**: The presence of a diazaspiro structure, which is a bicyclic system containing nitrogen atoms, can influence the molecule's rigidity and overall shape. This structural feature can affect how the molecule fits into the membrane pores, potentially enhancing or hindering permeability depending on the size and shape of the membrane.

3. **Phenylmethylamino Group**: This group introduces an amine functionality, which can participate in hydrogen bonding and ionic interactions. The presence of the amine group can increase the molecule's solubility in water, which is important for its interaction with the aqueous environment of the PAMPA assay. However, the balance between hydrophilic and lipophilic properties will determine the overall permeability.

4. **Phenol Group**: The phenol group is a hydroxyl group attached to an aromatic ring, which can also participate in hydrogen bonding. This group can increase the molecule's solubility in water and may enhance its interaction with the polar components of the artificial membrane.

Considering these structural features, the given molecule is likely to exhibit a balance between hydrophilic and lipophilic properties. The presence of multiple phenyl groups suggests a high degree of lipophilicity, which would favor permeability through the lipid-rich regions of the artificial membrane. However, the phenol and amine groups introduce polar characteristics that may enhance solubility and interaction with the aqueous phase. Overall, the molecule is expected to have high permeability due to its lipophilic nature, but the specific balance of its functional groups will determine the exact permeability profile in the PAMPA assay.

Final answer: High permeability.

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# 322

**SMILES:** CC1=CC=C(C=C1)S(=O)(=O)NC2=C(C=C(C=C2)F)C(=O)NC3=NC(=CS3)C4=CC=CC=C4

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a sulfonamide, which is a class of compounds known for their antibacterial properties. The sulfonamide group is characterized by the presence of a sulfonyl functional group attached to an amine. This group is known to enhance the molecule's ability to interact with biological targets, such as enzymes or receptors, due to its polar nature and ability to form hydrogen bonds.

In the given molecule, the sulfonamide group is attached to a benzamide moiety, which is a benzene ring linked to an amide group. The presence of the amide group can further enhance the molecule's ability to form hydrogen bonds, increasing its solubility and potentially its permeability across biological membranes.

The molecule also contains a thiazole ring, which is a five-membered heterocyclic compound containing both sulfur and nitrogen. This ring can contribute to the molecule's overall stability and ability to interact with biological targets due to its aromatic nature and potential for hydrogen bonding.

The presence of a fluorine atom on the phenyl ring can influence the molecule's lipophilicity and electronic properties. Fluorine is highly electronegative, which can affect the electron distribution within the molecule, potentially enhancing its ability to penetrate lipid membranes.

Overall, the combination of these functional groups suggests that the given molecule may have moderate to high permeability in the PAMPA assay. The sulfonamide group, along with the amide and thiazole rings, likely contribute to the molecule's ability to interact with the artificial membrane, while the fluorine atom may enhance its lipophilicity, aiding in membrane permeability.

Final answer: High permeability.

------
# 323

**SMILES:** C1=CSC(=C1)C2=NN=C(O2)NC(=O)C3=CC=C(C=C3)Cl

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several distinct functional groups and structural elements, each contributing to its permeability characteristics in the PAMPA assay.

1. **Amide Group**: The presence of the benzamide moiety indicates that the molecule has an amide linkage. Amides are generally polar and can form hydrogen bonds, which can enhance the molecule's solubility in polar solvents. This polar nature can facilitate interactions with the polar head groups of the artificial membrane, potentially increasing permeability.

2. **Chloro Substituent**: The chloro group on the benzene ring introduces a degree of lipophilicity to the molecule. Chlorine atoms can increase the molecule's ability to interact with lipid membranes due to their electron-withdrawing properties, which can enhance the molecule's overall hydrophobic character. This can improve the molecule's ability to permeate through the lipid-like environment of the artificial membrane.

3. **Thiadiazole Ring**: The thiadiazole ring is a heterocyclic compound containing both sulfur and nitrogen atoms. This ring can contribute to the molecule's overall polarity and ability to participate in hydrogen bonding and dipole-dipole interactions. The presence of this ring can enhance the molecule's ability to interact with the polar regions of the artificial membrane.

4. **Furan Ring**: The furan ring is another heterocyclic component that contributes to the molecule's overall aromaticity and polarity. Furans are known for their ability to engage in π-π interactions and hydrogen bonding, which can facilitate the molecule's interaction with the artificial membrane.

Overall, the given molecule's combination of polar and non-polar functional groups suggests that it can effectively interact with both the polar and non-polar regions of the artificial membrane. The presence of aromatic rings and heteroatoms can enhance its ability to permeate through the membrane, indicating that the molecule likely exhibits high permeability in the PAMPA assay.

Final answer: High permeability

------
# 324

**SMILES:** CN1CCCN(CC1)C(C2=CC=CC=C2)C3=CC=C(C=C3)Cl

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a diarylmethane, which is characterized by having two aromatic rings connected through a single methylene bridge. This structural feature often contributes to the molecule's lipophilicity, which can influence its permeability across biological membranes.

In the context of the Parallel Artificial Membrane Permeability Assay (PAMPA), the artificial membrane mimics the lipid bilayer of biological membranes. The permeability of the given molecule is likely influenced by several factors:

1. **Aromatic Rings**: The presence of two aromatic rings, one of which is a chlorophenyl group, increases the molecule's lipophilicity. This can enhance its ability to interact with the hydrophobic environment of the artificial membrane, potentially increasing its permeability.

2. **Methylene Bridge**: The methylene group connecting the aromatic rings provides a flexible linkage that can facilitate the molecule's orientation and interaction with the membrane. This flexibility can aid in the molecule's ability to traverse the membrane.

3. **Piperazine Ring**: The piperazine moiety introduces a basic nitrogen atom, which can form hydrogen bonds or ionic interactions with the membrane. This can enhance the molecule's solubility and permeability, depending on the pH of the environment.

4. **Methyl Substitution**: The methyl group on the piperazine ring can further increase the molecule's lipophilicity, potentially enhancing its permeability through the membrane.

Overall, the combination of lipophilic aromatic rings, a flexible methylene bridge, and a basic piperazine ring suggests that the given molecule may exhibit high permeability in the PAMPA assay. This is due to its ability to interact favorably with the artificial membrane, balancing hydrophobic and hydrophilic interactions to facilitate passage through the membrane.

Final answer: High permeability

------
# 325

**SMILES:** CN(CC1=CC=C(C=C1)/C=C/C(=O)NO)CC23CC4CC(C2)CC(C4)C3

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a derivative of adamantine, which is a tricyclic amine known for its bulky, cage-like structure. This structural feature contributes to the molecule's lipophilicity, enhancing its ability to interact with lipid membranes. The presence of the adamantine moiety suggests that the molecule may have a high degree of hydrophobic interactions, which can facilitate its passage through the lipid layers of the artificial membrane.

Additionally, the molecule contains a hydroxyimino group attached to a prop-2-enamide moiety. The hydroxyimino group can form hydrogen bonds, which may aid in the molecule's interaction with the polar head groups of the artificial membrane. However, the overall structure is dominated by the lipophilic adamantine, which likely outweighs the polar interactions, promoting permeability.

The phenyl rings in the structure also contribute to the molecule's lipophilicity and may enhance its ability to traverse the membrane by providing additional hydrophobic interactions. The presence of a methylamino group linked to the phenyl ring can further influence the molecule's solubility and permeability, potentially enhancing its interaction with the membrane.

Overall, the combination of the lipophilic adamantine core, hydrophobic phenyl rings, and polar hydroxyimino group suggests that the given molecule would exhibit high permeability in the artificial membrane.

Final answer: High permeability

------
# 326

**SMILES:** CC(C)(C#N)C1=CC=C(C=C1)N2C3=C4C=C(C=CC4=NC=C3COC2=O)C5=CC6=CC=CC=C6N=C5

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several distinct structural elements, each contributing to its permeability characteristics in the PAMPA assay.

1. **Aromatic Rings**: The molecule contains multiple aromatic rings, including a quinoline moiety and a pyridine ring. Aromatic rings are generally hydrophobic, which can enhance the molecule's ability to interact with the hydrophobic regions of the artificial membrane. This interaction can facilitate the passage of the molecule through the membrane, contributing to high permeability.

2. **Naphthyridine Core**: The naphthyridine structure is a bicyclic aromatic system that can further enhance the molecule's lipophilicity. This core can increase the overall hydrophobic character of the molecule, promoting its permeability through the membrane.

3. **Oxan-4-yl Group**: The presence of an oxan-4-yl group introduces an ether linkage, which can influence the molecule's solubility and permeability. Ethers can provide some degree of polarity, which might help the molecule to interact with polar sites on the membrane, potentially aiding in its permeation.

4. **2-Methylpropanenitrile Moiety**: This functional group includes a nitrile group, which is polar and can form hydrogen bonds or dipole-dipole interactions with the membrane. While the nitrile group can introduce some polarity, its presence in a relatively small and hydrophobic context might not significantly hinder the overall permeability of the molecule.

5. **Overall Structure**: The combination of these structural features suggests that the given molecule has a balance of hydrophobic and polar characteristics. The aromatic and bicyclic systems contribute to its lipophilicity, while the nitrile group provides some polar interaction potential. This balance can result in moderate to high permeability, as the molecule can effectively interact with both hydrophobic and polar regions of the artificial membrane.

In summary, the given molecule's structural features, including aromatic rings, a naphthyridine core, and a nitrile group, suggest that it would exhibit high permeability in the PAMPA assay.

Final answer: High permeability

------
# 327

**SMILES:** CN1CCN(CC1)C2=NC3=C(C=CC(=C3)Cl)NC4=CC=CC=C42

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a member of the dibenzodiazepine class, which is known for its psychoactive properties. The structure of the given molecule includes a dibenzodiazepine core, which is a tricyclic system consisting of two benzene rings fused to a diazepine ring. This core structure is crucial for its interaction with biological targets, particularly the central nervous system.

The presence of a chlorine atom on the benzene ring can influence the molecule's lipophilicity, potentially enhancing its ability to cross lipid membranes. This modification can increase the molecule's overall hydrophobic character, which is often associated with improved membrane permeability.

Additionally, the molecule contains a piperazine ring substituted with a methyl group. The piperazine moiety is a common feature in many pharmaceutical compounds, often contributing to improved solubility and bioavailability. The methyl group on the piperazine can further modulate the molecule's pharmacokinetic properties, potentially affecting its permeability and distribution.

Overall, the combination of the dibenzodiazepine core, the chlorine substituent, and the piperazine ring with a methyl group suggests that the given molecule likely exhibits high permeability through the artificial membrane, as these structural features are generally associated with favorable interactions with lipid bilayers.

Final answer: High permeability.

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# 328

**SMILES:** CCC1=CC=C(C=C1)NC(=O)C2=NN3C=CC=NC3=C2

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is an aromatic amide, which suggests that it contains an amide functional group attached to an aromatic ring. This structural feature is significant in determining the molecule's permeability.

The presence of the pyrazolo[1,5-a]pyrimidine core indicates a bicyclic aromatic system, which contributes to the molecule's rigidity and planarity. Aromatic systems are generally more lipophilic, which can enhance the molecule's ability to traverse lipid membranes. However, the specific arrangement of the pyrazolo and pyrimidine rings may also introduce some degree of polarity, which can affect permeability.

The 4-ethylphenyl group attached to the nitrogen atom of the amide introduces additional hydrophobic character to the molecule. This ethyl group can increase the lipophilicity of the molecule, potentially enhancing its ability to permeate through the lipid-rich environment of the artificial membrane.

The carboxamide group is polar and can form hydrogen bonds, which may influence the molecule's interaction with the membrane. While this group can contribute to solubility in aqueous environments, its presence in the context of an aromatic system may also allow for some degree of penetration through the membrane by interacting with polar sites.

Overall, the combination of aromaticity, hydrophobic ethyl groups, and a polar amide group suggests that the given molecule likely exhibits moderate permeability in the artificial membrane. The balance of lipophilic and polar characteristics allows it to interact with both hydrophobic and hydrophilic components of the membrane, facilitating its passage.

Final answer: Low-to-moderate permeability.

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# 329

**SMILES:** CC1=NN2CCCN(C2=C1C3=CC=CC=C3C4=CC=CC=C4)CC5CC5

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a member of the biphenyls, which indicates that it contains a biphenyl moiety. This structural feature is known for its hydrophobic character, which can influence the molecule's permeability. Biphenyls are typically lipophilic, meaning they have a tendency to dissolve in fats, oils, and non-polar solvents. This lipophilicity can enhance the molecule's ability to permeate lipid membranes, such as those found in biological systems.

The presence of a cyclopropylmethyl group adds to the hydrophobic nature of the molecule. Cyclopropyl groups are small, three-membered rings that introduce a degree of strain and rigidity to the molecule. This can affect the molecule's overall conformation and its interaction with the artificial membrane.

The pyrazolo[1,5-a]pyrimidine core is a heterocyclic structure that can contribute to the molecule's overall stability and electronic properties. This core may also play a role in the molecule's ability to interact with the artificial membrane, potentially affecting its permeability.

Overall, the combination of the biphenyl moiety, cyclopropylmethyl group, and pyrazolo[1,5-a]pyrimidine core suggests that the given molecule is likely to exhibit high permeability in the artificial membrane, as these structural features promote lipophilicity and membrane interaction.

Final answer: High permeability.

------
# 330

**SMILES:** CC(C)(C)C1=CC=C(C=C1)N2C=NC3=C2C=CC(=C3)C(=O)N4CCCCC4

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a member of the benzimidazole class, which is known for its diverse biological activities. The structure of the given molecule includes a benzimidazole core, which is a bicyclic compound consisting of a benzene ring fused to an imidazole ring. This core is known for its ability to interact with various biological targets, often contributing to the molecule's pharmacological properties.

The presence of a tert-butyl group attached to the phenyl ring enhances the molecule's lipophilicity, which can increase its ability to permeate lipid membranes. This is because the tert-butyl group is a bulky, hydrophobic moiety that can facilitate interactions with the lipid bilayer of cell membranes.

Additionally, the molecule contains a piperidine moiety, which is a six-membered nitrogen-containing heterocycle. Piperidine rings are commonly found in pharmaceuticals due to their ability to enhance solubility and improve the pharmacokinetic profile of compounds. The piperidine group can also contribute to the molecule's basicity, potentially affecting its ionization state and, consequently, its permeability across biological membranes.

Overall, the combination of the benzimidazole core, the lipophilic tert-butyl group, and the piperidine moiety suggests that the given molecule may exhibit high permeability in the PAMPA assay, as these structural features are conducive to crossing lipid membranes.

Final answer: High permeability.

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# 331

**SMILES:** C1CN(CCC1C(=O)N)C2=NC(=CS2)C3=CC4=CC=CC=C4C=C3

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a complex structure that includes several distinct functional groups and aromatic systems, which contribute to its permeability characteristics in the PAMPA assay.

1. **Naphthalene Moiety**: The presence of a naphthalene group, which is a polycyclic aromatic hydrocarbon, suggests that the given molecule has a relatively hydrophobic character. Naphthalene rings are known for their ability to interact with lipid membranes, which can enhance the permeability of the molecule through the artificial membrane. This is due to the non-polar nature of the aromatic rings, which can insert into the lipid bilayer, facilitating passage.

2. **Thiazole Ring**: The thiazole ring is a five-membered heterocyclic compound containing both sulfur and nitrogen. This ring can contribute to the molecule's overall polarity and ability to form hydrogen bonds. While the thiazole ring can enhance solubility in aqueous environments, it also provides a balance between hydrophilic and lipophilic properties, which can be beneficial for permeability through the PAMPA membrane.

3. **Piperidine Ring with Carboxamide**: The piperidine ring is a six-membered nitrogen-containing heterocycle, which is typically more polar and can enhance the solubility of the molecule in aqueous environments. The carboxamide group attached to the piperidine ring introduces additional hydrogen bonding capabilities, which can further influence the molecule's interaction with the PAMPA membrane. The presence of these polar groups can enhance the molecule's ability to interact with the polar head groups of the artificial membrane, potentially increasing permeability.

Overall, the given molecule's structure suggests a balance between hydrophobic and hydrophilic properties, which is typical for molecules with moderate permeability in PAMPA assays. The naphthalene moiety provides lipophilic character, while the thiazole and piperidine-carboxamide groups contribute to polar interactions. This combination of features likely results in moderate permeability, allowing the molecule to traverse the artificial membrane while still interacting with the membrane's polar components.

Final answer: Low-to-moderate permeability.

------
# 332

**SMILES:** CC1=CC=C(C=C1)N2C(=C3C(=NN(C(=O)C3=N2)CCCC(=O)NCC4=CC=CC=C4F)C)C

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a member of the pyrazole family, which is characterized by a five-membered ring containing two adjacent nitrogen atoms. This structural feature often contributes to the molecule's ability to participate in hydrogen bonding and other interactions, which can influence its permeability.

The presence of the pyrazolo[1,5-a]pyrimidine core in the given molecule suggests a relatively rigid and planar structure, which can enhance its ability to interact with the artificial membrane. This core is known for its potential to engage in π-π stacking interactions due to the aromatic nature of the rings, which can facilitate passage through the membrane.

The molecule also contains a 3,5-dimethylphenyl group, which is a hydrophobic aromatic ring. This hydrophobic character can enhance the molecule's ability to traverse lipid membranes, as it can interact with the hydrophobic regions of the artificial membrane.

Additionally, the presence of a fluorophenyl group introduces a fluorine atom, which can increase the molecule's lipophilicity and potentially improve its permeability by enhancing its ability to dissolve in lipid environments.

The butanamide linkage in the molecule provides a flexible chain that can help the molecule adapt to the membrane's structure, potentially facilitating its passage.

Overall, the combination of aromatic rings, hydrophobic groups, and the pyrazole core suggests that the given molecule likely exhibits high permeability in the artificial membrane, as these features enhance its ability to interact with and dissolve in the lipid-like environment of the membrane.

Final answer: High permeability.

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# 333

**SMILES:** C1CC(=O)NC2=C1C=CC(=C2)OCCCCN3CCN(CC3)C4=C(C(=CC=C4)Cl)Cl

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a member of the piperazine class, which is known for its diverse pharmacological properties. The structure of the given molecule includes several key features that influence its permeability:

1. **Piperazine Ring**: The presence of a piperazine ring, which is a six-membered ring containing two nitrogen atoms, contributes to the molecule's basicity and ability to form hydrogen bonds. This can enhance the molecule's solubility and permeability, as it can interact favorably with the polar environment of the artificial membrane.

2. **Dichlorophenyl Group**: The dichlorophenyl moiety introduces hydrophobic characteristics to the molecule. The chlorine atoms increase the lipophilicity, which can enhance membrane permeability by allowing the molecule to interact with the lipid bilayer of the artificial membrane. However, the presence of chlorine can also affect the molecule's overall polarity and solubility.

3. **Butoxy Linker**: The butoxy chain acts as a flexible spacer that connects the piperazine ring to the quinolinone core. This linker can influence the molecule's conformational flexibility, potentially affecting how it fits into the membrane and its overall permeability.

4. **Quinolinone Core**: The quinolinone structure is a bicyclic system that contributes to the molecule's rigidity and planarity. This can affect the molecule's ability to traverse the membrane by providing a stable framework that may interact with the membrane's hydrophobic regions.

Overall, the given molecule's combination of hydrophilic and hydrophobic features, along with its structural rigidity and flexibility, suggests that it may have moderate permeability in the artificial membrane. The dichlorophenyl group and piperazine ring enhance lipophilicity, while the quinolinone core and butoxy linker provide structural stability and flexibility, respectively. These characteristics collectively influence the molecule's ability to permeate the artificial membrane.

Final answer: Low-to-moderate permeability.

------
# 334

**SMILES:** CC1CCCN(C1)C(=O)C2=CC3=C(C=C2)N(C=N3)C4=CC=CC(=C4)C

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that includes several functional groups and structural features that influence its permeability in the PAMPA assay. Let's break down these features and their impact on permeability:

1. **Benzimidazole Core**: The presence of a benzimidazole moiety is significant. Benzimidazole is a bicyclic structure that consists of a benzene ring fused to an imidazole ring. This core is known for its planar structure, which can facilitate interactions with the artificial membrane. The aromatic nature of the benzene ring can contribute to π-π stacking interactions with the membrane, potentially enhancing permeability.

2. **3-Methylphenyl Substituent**: The 3-methylphenyl group attached to the benzimidazole core introduces a hydrophobic character to the molecule. The methyl group increases the lipophilicity of the molecule, which can enhance its ability to traverse lipid membranes. This hydrophobic interaction is crucial for permeability, as it allows the molecule to interact favorably with the lipid components of the artificial membrane.

3. **Piperidine Ring**: The piperidine moiety, specifically a 4-methylpiperidine, adds a degree of flexibility and basicity to the molecule. Piperidine is a six-membered nitrogen-containing heterocycle, which can enhance the molecule's solubility in aqueous environments. The presence of a nitrogen atom can also facilitate hydrogen bonding with the membrane, potentially aiding in permeability.

4. **Methanone Linkage**: The methanone group acts as a linker between the benzimidazole and piperidine moieties. This carbonyl group can participate in hydrogen bonding, which may influence the molecule's orientation and interaction with the membrane. The carbonyl group can also contribute to the overall polarity of the molecule, affecting its permeability.

Overall, the given molecule's structure suggests that it has a balance of hydrophobic and hydrophilic properties, which is typical for molecules with moderate to high permeability in PAMPA assays. The aromatic and hydrophobic components, along with the potential for hydrogen bonding, suggest that the molecule can effectively interact with the artificial membrane, leading to a classification of high permeability.

Final answer: High permeability

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# 335

**SMILES:** CC(C)N(CCCNC(=O)NC1=CC=C(C=C1)C(C)(C)C)C[C@@H]2[C@@H]([C@H]([C@@H](O2)N3C=C(C4=C(N=CN=C43)N)Br)O)O

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several functional groups and structural motifs, which contribute to its permeability characteristics in the PAMPA assay.

1. **Aromatic and Heterocyclic Components**: The presence of a pyrrolo[2,3-d]pyrimidine moiety, which is a bicyclic aromatic system, suggests that the molecule has a degree of rigidity and planarity. This can enhance its ability to interact with the artificial membrane, potentially increasing its permeability. The aromatic nature of this moiety can also facilitate π-π interactions with the membrane.

2. **Bromo Substitution**: The bromine atom on the pyrrolo[2,3-d]pyrimidine ring introduces a significant degree of electron-withdrawing character. This can affect the electronic distribution across the molecule, potentially influencing its interaction with the membrane. The presence of a halogen can also enhance lipophilicity, which is a favorable property for membrane permeability.

3. **Amino Group**: The amino group on the pyrrolo[2,3-d]pyrimidine ring can participate in hydrogen bonding, which may enhance the molecule's interaction with the membrane. However, the presence of this group can also introduce some polarity, which might reduce permeability to a certain extent.

4. **Sugar-like Moiety**: The oxolane ring, which resembles a sugar moiety, is substituted with hydroxyl groups. These hydroxyl groups can form hydrogen bonds with the membrane, potentially increasing the molecule's solubility and interaction with the membrane. The stereochemistry of the oxolane ring (with specific R and S configurations) can also play a crucial role in the molecule's three-dimensional shape, affecting how it fits into the membrane.

5. **Alkyl and Tertiary Butyl Groups**: The presence of a tert-butyl group and an alkyl chain in the urea moiety contributes to the hydrophobic character of the molecule. These groups can enhance the lipophilicity, which is generally favorable for permeability through lipid membranes.

6. **Urea Linkage**: The urea linkage in the molecule can participate in hydrogen bonding, which might influence the molecule's interaction with the membrane. Urea groups are often involved in forming stable hydrogen bonds, which can affect the overall permeability.

Overall, the given molecule's combination of aromatic, heterocyclic, and hydrophobic components, along with its ability to form hydrogen bonds, suggests that it would have high permeability in the PAMPA assay. The balance of hydrophilic and hydrophobic properties, along with the structural rigidity and specific stereochemistry, likely facilitate its passage through the artificial membrane.

Final answer: High permeability

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# 336

**SMILES:** C1=CSC(=C1)C2=CC(=NC(=N2)S(=O)(=O)CCC(=O)NC3=CC=C(C=C3)OC(F)(F)F)C(F)(F)F

**Label:** 0

**Predi:** 1

**Correct:** 0

# Response:
The given molecule is a complex organic compound that includes several functional groups and structural features that influence its permeability in the PAMPA assay. Let's break down these features and their impact on permeability:

1. **Trifluoromethyl Groups**: The presence of trifluoromethyl groups in the molecule, specifically on the pyridine ring and the phenyl ring, increases the lipophilicity of the compound. This can enhance the molecule's ability to traverse lipid membranes, contributing to higher permeability.

2. **Pyridine Ring**: The pyridine ring is a heteroaromatic structure that can participate in π-π interactions with the artificial membrane. This can facilitate the passage of the molecule through the membrane, potentially increasing permeability.

3. **Thiophene Ring**: The thiophene ring, another heteroaromatic structure, can also engage in π-π interactions. Its presence may enhance the molecule's ability to interact with the membrane, contributing to permeability.

4. **Sulfonyl Group**: The sulfonyl group is a polar functional group that can form hydrogen bonds with the membrane. While it may introduce some polarity, its presence is balanced by the lipophilic groups, which could still allow for moderate permeability.

5. **Propanamide Moiety**: The amide group in the propanamide moiety can also form hydrogen bonds, which might influence the molecule's interaction with the membrane. However, the overall structure is dominated by lipophilic groups, suggesting that the amide's influence on permeability is less significant compared to the other groups.

6. **Trifluoromethoxyphenyl Group**: This group adds to the lipophilicity of the molecule, enhancing its ability to permeate the membrane. The ether linkage in the trifluoromethoxy group can also contribute to the molecule's overall stability and solubility profile.

Overall, the given molecule's structure, characterized by multiple lipophilic groups and heteroaromatic rings, suggests that it would have high permeability in the PAMPA assay. The balance of polar and non-polar groups allows it to interact favorably with the artificial membrane, facilitating its passage.

Final answer: High permeability.

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# 337

**SMILES:** C1CN(CCC1C(=O)N)C2=NC(=CS2)C3=CC=CC=C3C4=CC=CC=C4

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several distinct structural components, each contributing to its permeability characteristics in the PAMPA assay.

1. **Biphenyl Structure**: The presence of a biphenyl moiety, which consists of two phenyl rings connected by a single bond, is a significant contributor to the molecule's hydrophobic character. This hydrophobicity can enhance the molecule's ability to interact with the lipid components of the artificial membrane, potentially increasing its permeability.

2. **Thiazole Ring**: The thiazole ring, a five-membered heterocyclic compound containing both sulfur and nitrogen, adds to the molecule's overall aromaticity and electronic properties. The thiazole ring can participate in π-π interactions with the membrane, further facilitating permeation.

3. **Piperidine Ring**: The piperidine ring is a six-membered nitrogen-containing heterocycle that imparts basicity to the molecule. This basicity can influence the molecule's solubility and permeability, as the nitrogen atom can form hydrogen bonds or ionic interactions with the membrane, potentially enhancing permeability.

4. **Carboxamide Group**: The carboxamide group introduces a polar functional group to the molecule, which can form hydrogen bonds with the membrane. This group can also affect the molecule's solubility and permeability by providing a site for interaction with the polar components of the membrane.

Overall, the combination of hydrophobic biphenyl and aromatic thiazole rings, along with the polar carboxamide group and basic piperidine ring, suggests that the given molecule would exhibit high permeability in the PAMPA assay. The balance of hydrophobic and hydrophilic interactions allows the molecule to effectively traverse the artificial membrane.

Final answer: High permeability

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# 338

**SMILES:** C1=CC=NC(=C1)C(=O)NC2=CC=C(C=C2)[S+](=O)(NC3=NC=CS3)[O-]

**Label:** 0

**Predi:** 1

**Correct:** 0

# Response:
The given molecule is an aromatic amide, which suggests that it contains an amide functional group attached to an aromatic ring. This structural feature is significant in determining the molecule's permeability.

The molecule contains a pyridine ring, which is a nitrogen-containing aromatic ring. Pyridine rings are known for their ability to participate in hydrogen bonding and π-π interactions, which can enhance the molecule's ability to interact with the artificial membrane. This interaction can contribute to the molecule's permeability.

Additionally, the molecule has a thiazole ring, which is a five-membered ring containing both sulfur and nitrogen. Thiazole rings are often involved in biological activity due to their ability to form hydrogen bonds and participate in π-π stacking interactions. This can also enhance the molecule's permeability by facilitating interactions with the membrane.

The presence of a sulfonamide group, which is a sulfur atom double-bonded to two oxygen atoms and single-bonded to a nitrogen atom, is another key feature. Sulfonamides are known for their ability to form strong hydrogen bonds, which can increase the molecule's solubility and permeability.

Overall, the combination of aromatic rings, the amide linkage, and the sulfonamide group in the given molecule suggests that it can effectively interact with the artificial membrane, leading to high permeability.

Final answer: High permeability.

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# 339

**SMILES:** CC1=CC=C(C=C1)C2=NC(=NC=C2)N3CCC(CC3)C(=O)N

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a member of pyrimidines and contains a piperidine ring, which is a six-membered ring containing one nitrogen atom. The presence of the pyrimidine ring, which is a heterocyclic aromatic organic compound, suggests that the molecule has a planar structure, contributing to its ability to interact with biological membranes.

The molecule also features a 4-methylphenyl group attached to the pyrimidine ring. This aromatic group can enhance the lipophilicity of the molecule, which is a key factor in determining its permeability. Lipophilic molecules tend to have higher permeability through lipid membranes due to their ability to dissolve in the lipid bilayer.

Additionally, the molecule contains a carboxamide group attached to the piperidine ring. This functional group can form hydrogen bonds, which may influence the molecule's interaction with the artificial membrane. The presence of this group can also affect the molecule's solubility and permeability by introducing polar characteristics.

Overall, the combination of the pyrimidine ring, the lipophilic 4-methylphenyl group, and the polar carboxamide group suggests that the given molecule likely has moderate permeability through the artificial membrane. The balance of hydrophobic and hydrophilic properties allows it to interact with both the lipid and aqueous environments, facilitating its passage through the membrane.

Final answer: Low-to-moderate permeability.

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# 340

**SMILES:** CCOC1=CC=CC=C1N2CC(CC2=O)C3=NC4=CC=CC=C4N3CCOC5=CC=C(C=C5)C(C)(C)C

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several distinct structural components, each contributing to its permeability characteristics in the PAMPA assay.

1. **Benzimidazole Moiety**: The presence of a benzimidazole ring is significant in drug design due to its ability to interact with biological targets. This heterocyclic structure is known for its planar nature, which can facilitate interactions with the artificial membrane, potentially enhancing permeability.

2. **Phenyl and Ethoxyphenyl Groups**: The molecule contains phenyl groups, which are aromatic and hydrophobic. These groups can enhance lipophilicity, which is often associated with better membrane permeability. The ethoxyphenyl group, in particular, adds an ether linkage that can influence the molecule's solubility and permeability by providing a balance between hydrophilic and hydrophobic properties.

3. **Piperazinone Core**: The piperazinone ring is a six-membered heterocyclic structure that can contribute to the molecule's overall stability and rigidity. This core can affect the molecule's ability to traverse the membrane by providing a scaffold that supports the orientation of the functional groups.

4. **Alkyl Chains**: The presence of alkyl chains, such as the isopropyl group attached to the phenyl ring, increases the hydrophobic character of the molecule. This can enhance the molecule's ability to interact with the lipid components of the artificial membrane, potentially improving permeability.

Overall, the given molecule's combination of aromatic rings, heterocyclic structures, and alkyl chains suggests that it has a balanced hydrophilic-lipophilic profile. This balance is often associated with favorable permeability in PAMPA assays, indicating that the molecule likely exhibits high permeability through the artificial membrane.

Final answer: High permeability

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# 341

**SMILES:** CCC1=CC=C(C=C1)NC(=O)[C@H](CC2=CNC3=CC=CC=C32)NC(=O)[C@@H]4CC5=CC=CC=C5CN4

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that can be analyzed for its permeability based on its structural features. The molecule is a dipeptide, which means it is composed of two amino acid residues linked by a peptide bond. This structural feature is significant because peptides often have specific interactions with biological membranes, influencing their permeability.

The presence of the indole group, derived from the tryptophan residue, is a key factor in determining the molecule's permeability. Indole groups are known for their ability to engage in π-π interactions and hydrogen bonding, which can enhance the molecule's ability to interact with the artificial membrane. This interaction can increase the permeability of the molecule by facilitating its passage through the membrane.

Additionally, the molecule contains an ethylphenyl group, which is a hydrophobic moiety. This hydrophobic character can also contribute to the molecule's permeability by allowing it to interact with the lipid components of the artificial membrane, promoting its diffusion across the membrane.

The overall structure of the given molecule, with its combination of aromatic and hydrophobic groups, suggests that it can effectively interact with the artificial membrane, leading to a classification of high permeability. This is consistent with the typical behavior of small peptides and aromatic compounds in permeability assays.

Final answer: High permeability.

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# 342

**SMILES:** CC1=CC(=C(C=C1)C)CN2C3=C(C=CC(=C3)C(=O)N4CCN(CC4)C5=CC=CC=C5F)S(=O)C6=CC=CC=C6C2=O

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several distinct structural components, each contributing to its permeability characteristics in the PAMPA assay.

1. **Phenyl Groups**: The presence of phenyl groups, such as the 2,6-dimethylphenyl and the 2-fluorophenyl, contributes to the hydrophobic character of the molecule. These aromatic rings can enhance the molecule's ability to interact with the hydrophobic regions of the artificial membrane, potentially increasing its permeability.

2. **Fluorine Substitution**: The fluorine atom on the phenyl ring can influence the electronic properties of the molecule. Fluorine is highly electronegative, which can affect the molecule's overall polarity and potentially enhance its ability to permeate the membrane by increasing its lipophilicity.

3. **Benzothiazine Core**: The benzothiazine moiety is a bicyclic structure that includes both sulfur and nitrogen atoms. This core can contribute to the molecule's rigidity and overall shape, which may affect how it fits into the membrane. The presence of sulfur and nitrogen can also introduce polar characteristics, which might influence the molecule's interaction with the membrane.

4. **Piperazine Ring**: The piperazine ring is a common feature in many pharmaceuticals and can enhance the solubility and permeability of the molecule. The nitrogen atoms in the piperazine ring can participate in hydrogen bonding, which may facilitate interaction with the membrane.

5. **Carbonyl Group**: The carbonyl group in the molecule is a polar functional group that can form hydrogen bonds with the membrane. This can enhance the molecule's interaction with the membrane, potentially increasing its permeability.

Overall, the given molecule's structure suggests that it has a balance of hydrophobic and hydrophilic characteristics, which is typical for molecules with moderate to high permeability in PAMPA assays. The aromatic rings and fluorine substitution likely enhance its lipophilicity, while the piperazine and carbonyl groups provide opportunities for polar interactions. These features collectively suggest that the given molecule would exhibit high permeability in the PAMPA assay.

Final answer: High permeability

------
# 343

**SMILES:** CCOC(=O)C1=C(C(=C(N1)C)CCC(=O)N2CCN(CC2)C3=CC=CC(=C3C)C)C

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several distinct structural components, each contributing to its permeability characteristics in the PAMPA assay.

1. **Piperazine Ring**: The presence of a piperazine ring, which is a six-membered heterocyclic structure containing two nitrogen atoms, is significant. Piperazine rings are known for their ability to enhance the solubility and permeability of molecules due to their basic nature and potential for hydrogen bonding. This can facilitate the molecule's interaction with the artificial membrane, potentially increasing its permeability.

2. **Dimethylphenyl Group**: The dimethylphenyl moiety, which is a phenyl ring substituted with two methyl groups, contributes to the hydrophobic character of the molecule. This hydrophobicity can enhance the molecule's ability to traverse lipid membranes, as it may interact favorably with the lipid bilayer of the artificial membrane.

3. **Pyrrole Ring**: The pyrrole ring, a five-membered heterocyclic aromatic ring containing one nitrogen atom, adds to the molecule's aromatic character. Pyrrole rings can participate in π-π interactions with the membrane, potentially aiding in permeability. However, the presence of the pyrrole ring may also introduce some degree of polarity, which could influence the overall permeability balance.

4. **Ethyl Ester Group**: The ethyl ester functional group is an ester linkage that can affect the molecule's lipophilicity and stability. Esters are generally more lipophilic, which can enhance membrane permeability. However, esters can also be susceptible to hydrolysis, which might affect the molecule's stability in the PAMPA assay.

5. **Overall Structure**: The combination of these structural elements suggests that the given molecule has a balance of hydrophobic and hydrophilic properties, which is typical for molecules with moderate permeability in PAMPA assays. The piperazine and dimethylphenyl groups likely contribute to high permeability due to their hydrophobic and basic characteristics, while the pyrrole and ethyl ester groups may introduce some polarity and potential for interaction with the membrane.

In summary, the given molecule is likely to exhibit high permeability in the PAMPA assay due to its balanced hydrophobic and hydrophilic properties, as well as its ability to engage in various non-covalent interactions with the artificial membrane.

Final answer: High permeability

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# 344

**SMILES:** CC(=O)NC1=CC=C(C=C1)C(=O)NC2=CC3=C(C=C2)SC4=CC=CC=C4C(=O)N3C5CCCC5

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a member of the benzothiazines, which are known for their diverse biological activities. To predict its permeability in the PAMPA assay, we need to consider the structural features of the molecule.

The molecule contains a benzothiazine core, which is a bicyclic structure combining a benzene ring with a thiazine ring. This core is known for its planar and aromatic nature, which can facilitate interactions with biological membranes. The presence of the benzothiazine moiety suggests that the molecule may have moderate to high permeability due to its aromatic and heterocyclic nature, which can enhance lipophilicity and membrane affinity.

Additionally, the molecule has an acetamidobenzoyl group attached to the benzothiazine core. The acetamidobenzoyl group introduces an amide linkage, which can increase the molecule's polarity and potentially improve its solubility in aqueous environments. However, the aromatic nature of the benzoyl part can still contribute to membrane permeability by allowing the molecule to interact with lipid bilayers.

The cyclopentyl group attached to the benzothiazine core adds a non-polar, hydrophobic character to the molecule. This can enhance the molecule's ability to penetrate lipid membranes, contributing to its overall permeability.

In summary, the given molecule's benzothiazine core, aromatic groups, and cyclopentyl substituent suggest that it likely has high permeability in the PAMPA assay due to its balance of aromaticity, hydrophobicity, and moderate polarity.

Final answer: High permeability.

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# 345

**SMILES:** CC(=O)C1=CC=CC(=C1)C2=CSC(=N2)N3CCC(CC3)C(=O)N

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a piperidinecarboxamide, which is a type of compound that features a piperidine ring attached to a carboxamide group. This structural motif is often associated with various pharmacological activities due to its ability to interact with biological targets.

In the context of the Parallel Artificial Membrane Permeability Assay (PAMPA), the permeability of the given molecule is influenced by several key structural elements:

1. **Piperidine Ring**: The presence of the piperidine ring contributes to the molecule's basicity and can enhance its ability to permeate biological membranes. Piperidine rings are commonly found in many bioactive compounds and can improve the molecule's solubility and permeability.

2. **Thiazole Ring**: The thiazole ring is a heterocyclic compound containing both sulfur and nitrogen. This ring can enhance the molecule's ability to interact with biological targets through hydrogen bonding and π-π interactions. The thiazole ring can also contribute to the overall lipophilicity of the molecule, which can affect its permeability.

3. **Phenyl Group with Acetyl Substitution**: The phenyl group provides a hydrophobic character, which can facilitate membrane permeation by interacting with the lipid bilayer of the membrane. The acetyl substitution on the phenyl ring can further modulate the molecule's lipophilicity and electronic properties, potentially enhancing its permeability.

4. **Carboxamide Group**: The carboxamide group is polar and can form hydrogen bonds with the membrane or surrounding environment. This group can also contribute to the molecule's solubility in aqueous environments, which is important for its transport across biological membranes.

Overall, the combination of these structural features suggests that the given molecule likely exhibits high permeability in the PAMPA assay. The balance of hydrophobic and hydrophilic elements, along with the presence of functional groups capable of interacting with the membrane, supports its ability to traverse the artificial membrane.

Final answer: High permeability

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# 346

**SMILES:** CC(C)C1=CC=CC=C1C2=NC=C(C(=N2)NCC3CCN(C3)C4=NC=CN=C4)F

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound with several functional groups and structural features that influence its permeability in the PAMPA assay. Let's break down these features and their impact on permeability:

1. **Fluorinated Aromatic Ring**: The presence of a fluorine atom on the aromatic ring can increase the lipophilicity of the molecule. Fluorine is a small, highly electronegative atom that can enhance the molecule's ability to interact with lipid membranes, potentially increasing its permeability.

2. **Pyrimidine Ring**: The pyrimidine moiety is a heterocyclic aromatic ring that can contribute to the molecule's overall planarity and rigidity. This structural feature can facilitate the molecule's passage through the lipid bilayer by allowing it to fit snugly within the membrane's hydrophobic core.

3. **Pyridine Ring**: The pyridine ring is another heterocyclic aromatic structure that can enhance the molecule's ability to interact with the lipid membrane. The nitrogen atom in the pyridine ring can participate in hydrogen bonding or ionic interactions with the membrane, potentially aiding in permeation.

4. **Amino Group**: The presence of an amino group attached to the pyrimidine ring can increase the molecule's polarity and hydrogen bonding capacity. This functional group can enhance solubility in aqueous environments, which is important for the initial stages of permeation through the PAMPA assay.

5. **Isopropyl Group**: The isopropyl group attached to the pyrimidine ring is a hydrophobic alkyl group that can increase the lipophilicity of the molecule. This group can enhance the molecule's ability to embed within the lipid bilayer, promoting permeability.

Overall, the given molecule exhibits a balance of hydrophobic and hydrophilic features, with several aromatic and heterocyclic rings that facilitate interaction with the lipid membrane. The presence of fluorine and isopropyl groups further enhances lipophilicity, while the amino group contributes to solubility and potential hydrogen bonding. These structural characteristics suggest that the given molecule would have high permeability in the PAMPA assay.

Final answer: High permeability

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# 347

**SMILES:** C1CCCN(CC1)C2=NC(=NC3=CC=CC=C32)C4=CC=CC=N4

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a member of the quinazoline family, which is known for its diverse biological activities. The structure of the given molecule includes a quinazoline core, which is a bicyclic compound consisting of a benzene ring fused to a pyrimidine ring. This core is known for its planar structure, which can facilitate interactions with biological targets.

Attached to the quinazoline core is a pyridinyl group. Pyridine rings are aromatic and can participate in π-π stacking interactions, which may enhance the molecule's ability to interact with other aromatic systems in biological environments. The presence of the pyridinyl group can also increase the molecule's lipophilicity, potentially improving its ability to permeate lipid membranes.

Additionally, the molecule contains a pyrrolidinyl group. Pyrrolidine is a saturated five-membered nitrogen-containing ring, which can increase the molecule's solubility and enhance its ability to form hydrogen bonds. This group can also contribute to the overall basicity of the molecule, which may affect its ionization state and, consequently, its permeability.

In the context of the Parallel Artificial Membrane Permeability Assay (PAMPA), the given molecule's permeability is influenced by its ability to traverse a lipid-like membrane. The quinazoline core, along with the pyridinyl and pyrrolidinyl groups, suggests that the molecule has a balance of hydrophobic and hydrophilic properties, which can facilitate its passage through the membrane. However, the exact permeability would depend on the specific conditions of the assay, such as the type of membrane used and the presence of other molecules that might compete for permeation.

Overall, the given molecule is likely to exhibit moderate permeability due to its balanced hydrophilic and hydrophobic characteristics, as well as its ability to engage in various non-covalent interactions.

Final answer: Low-to-moderate permeability.

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# 348

**SMILES:** COC1=CC=CC=C1N2CCN(CC2)C3=NC4=C(C=C3)C=C(C=C4)S(=O)(=O)N5CCCCC5

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex structure that includes several functional groups and aromatic systems, which influence its permeability in the PAMPA assay. Let's break down the structural components and their impact on permeability:

1. **Piperazine Ring**: The presence of a piperazine ring, which is a six-membered ring containing two nitrogen atoms, contributes to the molecule's basicity and potential for hydrogen bonding. This can enhance the molecule's solubility in water and its ability to interact with the polar head groups of the artificial membrane, potentially increasing its permeability.

2. **Methoxyphenyl Group**: The methoxy group attached to the phenyl ring introduces an ether linkage, which can increase the lipophilicity of the molecule. This can facilitate the passage of the molecule through the lipid-like environment of the artificial membrane, contributing to higher permeability.

3. **Quinoline Core**: The quinoline moiety is a bicyclic aromatic system that can enhance the molecule's ability to intercalate with lipid bilayers. This aromatic system can also participate in π-π interactions with the artificial membrane, which may aid in permeation.

4. **Sulfonyl Group**: The sulfonyl group is a strong electron-withdrawing group that can increase the molecule's polarity. This can enhance the molecule's solubility in aqueous environments and its ability to form hydrogen bonds with the artificial membrane, potentially improving permeability.

5. **Piperidine Ring**: The piperidine ring is a saturated nitrogen-containing heterocycle that can contribute to the basicity and solubility of the molecule. This can facilitate interactions with the polar head groups of the artificial membrane, enhancing permeability.

Overall, the given molecule contains a combination of polar and non-polar groups, aromatic systems, and basic nitrogen atoms, which collectively suggest that it would have high permeability in the PAMPA assay. The balance of hydrophilic and lipophilic properties allows the molecule to effectively interact with the artificial membrane, facilitating its passage through the membrane.

Final answer: High permeability.

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# 349

**SMILES:** C1CCC(CC1)C(=O)NCCC2=NC3=CC=CC=C3N2CCOC4=CC=CC=C4N

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a member of the benzimidazole class, which is known for its diverse biological activities and ability to interact with various biological targets. The benzimidazole core is a bicyclic structure consisting of a benzene ring fused to an imidazole ring. This core is often associated with high permeability due to its planar and aromatic nature, which allows it to easily pass through lipid membranes.

In the given molecule, the benzimidazole moiety is linked to a cyclohexanecarboxamide group. The cyclohexane ring is a non-aromatic, saturated hydrocarbon, which can contribute to the molecule's overall lipophilicity. This lipophilic nature can enhance the molecule's ability to permeate lipid membranes, potentially increasing its permeability.

Additionally, the molecule contains an amino group attached to a phenoxyethyl chain. The presence of the amino group can introduce hydrogen bonding capabilities, which may influence the molecule's interaction with the artificial membrane. The phenoxy group, being an aromatic ether, can also contribute to the molecule's overall lipophilicity and may facilitate membrane permeation.

Overall, the combination of the benzimidazole core, the cyclohexanecarboxamide group, and the phenoxyethyl chain with an amino group suggests that the given molecule likely exhibits high permeability in the artificial membrane assay. This is due to the balance of lipophilic and hydrogen bonding characteristics that enhance its ability to traverse the membrane.

Final answer: High permeability.

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# 350

**SMILES:** CN1C=CC2=C1C=CC(=C2)C3=CSC(=N3)N4CCC(CC4)C(=O)N

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a piperidinecarboxamide, which is a type of compound that includes a piperidine ring attached to a carboxamide group. This structural feature is significant in drug design as piperidine rings are commonly found in pharmaceuticals due to their ability to enhance the solubility and bioavailability of compounds.

The molecule also contains a thiazole ring, which is a five-membered ring containing both sulfur and nitrogen atoms. Thiazole rings are known for their electron-rich nature, which can contribute to the molecule's ability to interact with biological targets through hydrogen bonding and π-π interactions.

Additionally, the presence of an indole moiety, which is a bicyclic structure consisting of a benzene ring fused to a pyrrole ring, is notable. Indole structures are prevalent in many natural products and pharmaceuticals due to their ability to mimic the structure of tryptophan, an essential amino acid. This can enhance the molecule's ability to interact with biological systems, potentially increasing its permeability and activity.

The overall structure of the given molecule, with its combination of a piperidine ring, thiazole, and indole, suggests that it may have favorable interactions with the artificial membrane used in the PAMPA assay. The presence of these heterocyclic components can enhance the molecule's ability to permeate the membrane, indicating that the given molecule likely exhibits high permeability in the PAMPA assay.

Final answer: High permeability.

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# 351

**SMILES:** CC(C)CNC1=NC(=NC=C1)NCC2=CSC(=N2)C3=CC=CC=C3

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several functional groups and structural motifs that influence its permeability in the PAMPA assay. Let's break down the structural components and their impact on permeability:

1. **Aromatic Rings**: The molecule contains a phenyl group and a thiazolopyrimidine moiety. Aromatic rings, such as phenyl and thiazole, contribute to the lipophilicity of the molecule. Lipophilicity is a key factor in membrane permeability, as it allows the molecule to interact with and penetrate lipid bilayers. Therefore, the presence of these aromatic rings suggests that the given molecule may have a moderate to high permeability.

2. **Thiazole Ring**: The thiazole ring is a heterocyclic compound containing both sulfur and nitrogen. This ring can enhance the molecule's ability to interact with biological membranes due to its aromatic nature and potential for hydrogen bonding. The thiazole ring may also contribute to the molecule's overall stability and solubility, which can further influence permeability.

3. **Pyrimidine Ring**: The pyrimidine ring is another heterocyclic component of the molecule. Pyrimidines are known for their ability to participate in hydrogen bonding and π-π stacking interactions, which can facilitate the molecule's interaction with the artificial membrane. This can enhance the permeability of the molecule.

4. **Amine Group**: The presence of an amine group in the pyrimidine ring can increase the molecule's polarity and solubility in aqueous environments. This can improve the molecule's ability to traverse the PAMPA membrane, which is typically composed of a lipid bilayer.

5. **Isobutyl Side Chain**: The isobutyl group attached to the nitrogen atom of the pyrimidine ring introduces a degree of hydrophobicity to the molecule. This can enhance the molecule's ability to interact with the lipid components of the membrane, potentially increasing its permeability.

Overall, the combination of aromatic rings, heterocyclic structures, and functional groups such as amines and alkyl chains suggests that the given molecule is likely to have high permeability in the PAMPA assay. The balance of hydrophobic and hydrophilic properties allows it to effectively interact with the artificial membrane, facilitating its passage through the lipid layer.

Final answer: High permeability

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# 352

**SMILES:** COC1=CC=CC(=C1)CNCC2=CC=CN2C3=NN=C(S3)N4CCN(CC4)C5=CC=CC=C5

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex structure that includes several functional groups and heterocyclic rings, which contribute to its permeability characteristics. Let's break down the structural components and their influence on permeability:

1. **Piperazine Ring**: The presence of a piperazine ring, which is a six-membered ring containing two nitrogen atoms, is known to enhance the solubility and permeability of molecules. Piperazine rings are often found in pharmaceuticals due to their ability to improve bioavailability. In this molecule, the piperazine ring is substituted with a phenyl group, which can further increase lipophilicity, potentially enhancing membrane permeability.

2. **Phenyl Groups**: The molecule contains multiple phenyl groups, which are aromatic rings. These rings can increase the lipophilicity of the molecule, which is often associated with better membrane permeability. However, the balance between hydrophobic and hydrophilic properties is crucial, and the presence of other polar groups will influence overall permeability.

3. **Methoxyphenyl Group**: The methoxy group attached to the phenyl ring introduces a degree of polarity, which can affect the molecule's ability to interact with the membrane. The methoxy group can enhance solubility in aqueous environments, which may aid in permeability.

4. **Thiadiazole Ring**: The thiadiazole ring is a heterocyclic compound containing both sulfur and nitrogen atoms. This ring can contribute to the molecule's electronic properties and may influence its interaction with the artificial membrane. The presence of heteroatoms can also affect the molecule's hydrogen bonding capabilities, which is important for permeability.

5. **Pyridine Ring**: The pyridine ring is another aromatic heterocycle that can contribute to the molecule's basicity and ability to form hydrogen bonds. This can affect the molecule's interaction with the membrane and its overall permeability.

Overall, the given molecule's structure suggests that it has a balance of hydrophobic and hydrophilic properties, which is typical for molecules with moderate to high permeability in PAMPA assays. The presence of aromatic rings and heterocycles, along with polar functional groups, indicates that the molecule can effectively interact with the artificial membrane, potentially leading to high permeability.

Final answer: High permeability

------
# 353

**SMILES:** COC1=CC=CC=C1N2CCN(CC2)CCN(C3=CC=CC=N3)C(=O)C4=CC=C(C=C4)F

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several functional groups and structural elements that influence its permeability in the PAMPA assay. Let's break down these features and their impact on permeability:

1. **Fluorophenyl Group**: The presence of a fluorine atom on the phenyl ring can enhance the lipophilicity of the molecule. Fluorine is a small, electronegative atom that can increase the molecule's ability to interact with lipid membranes, potentially improving its permeability.

2. **Benzamide Moiety**: The benzamide group is a polar functional group that can form hydrogen bonds. While this may contribute to some degree of water solubility, the overall effect on permeability will depend on the balance between hydrophilic and lipophilic properties. In this case, the benzamide group is likely to contribute to moderate permeability due to its ability to interact with both polar and non-polar environments.

3. **Pyridine Ring**: The pyridine ring is a heteroaromatic structure that can enhance the molecule's ability to interact with biological membranes. Pyridine rings are known for their ability to participate in π-π stacking interactions and hydrogen bonding, which can facilitate membrane permeation.

4. **Piperazine Ring**: The piperazine ring is a flexible, nitrogen-containing heterocycle that can enhance the solubility and permeability of the molecule. Piperazine rings are often used in drug design to improve pharmacokinetic properties, including membrane permeability.

5. **Ethyl Linker**: The ethyl chain connecting the piperazine and benzamide moieties provides flexibility and spatial separation between these functional groups. This can influence the overall conformation of the molecule and its ability to fit into the membrane.

Overall, the given molecule contains a combination of lipophilic and polar functional groups that suggest moderate to high permeability in the PAMPA assay. The presence of fluorine, aromatic rings, and heterocycles likely contribute to its ability to traverse the artificial membrane, while the benzamide and piperazine groups provide a balance of hydrophilic and lipophilic properties.

Final answer: High permeability

------
# 354

**SMILES:** C1CC1C2=NC3=C(CCN(CC3)CC4=CC=C(C=C4)F)C(=N2)C5=CC=C(C=C5)O

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound with several distinct structural features that influence its permeability in the PAMPA assay. Let's break down these features and their implications:

1. **Phenolic Group**: The presence of a phenolic group, which is a hydroxyl group attached to a benzene ring, contributes to the molecule's polarity. This can enhance the molecule's ability to form hydrogen bonds with the artificial membrane, potentially increasing its permeability. However, the phenolic group can also lead to moderate permeability due to its potential to interact strongly with the membrane, which might hinder diffusion.

2. **Cyclopropylmethyl Group**: The cyclopropylmethyl group is a small, non-polar moiety that can increase the lipophilicity of the molecule. This lipophilic character can enhance the molecule's ability to traverse lipid membranes, suggesting a higher permeability.

3. **Fluorophenyl Group**: The fluorophenyl group introduces a fluorine atom into the aromatic ring, which can increase the molecule's lipophilicity and metabolic stability. The presence of fluorine can also affect the electronic properties of the aromatic ring, potentially enhancing the molecule's ability to interact with the membrane.

4. **Dihydropyridopyrimidine Core**: This bicyclic structure is relatively rigid and can influence the overall shape of the molecule. The rigidity can affect how the molecule fits into the membrane, potentially impacting its permeability. The nitrogen atoms in the pyrimidine ring can also participate in hydrogen bonding, which might affect the molecule's interaction with the membrane.

Overall, the given molecule has a combination of polar and non-polar features, along with a rigid bicyclic core. These characteristics suggest that the molecule has a balance of properties that could result in moderate to high permeability in the PAMPA assay. The presence of both polar and non-polar groups allows the molecule to interact with the artificial membrane through various non-covalent interactions, which is essential for permeability.

Final answer: High permeability

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# 355

**SMILES:** C1=CC=C(C=C1)C2=CC=C(C=C2)S(=O)(=O)NC3=C(C=CN=C3)C(=O)NC4=NC(=CS4)C5=CC=CC=C5

**Label:** 0

**Predi:** 1

**Correct:** 0

# Response:
The given molecule is a sulfonamide, which is a class of compounds known for their antibacterial properties. The sulfonamide group is characterized by the presence of a sulfonyl functional group attached to an amine. This group is known to enhance the molecule's ability to interact with biological membranes due to its polar nature, which can facilitate passage through lipid bilayers.

The structure of the given molecule includes several key components that influence its permeability:

1. **Sulfonamide Group**: The presence of the sulfonamide moiety contributes to the molecule's overall polarity, which can enhance its permeability through lipid membranes. This group is often involved in hydrogen bonding and ionic interactions, which can aid in the molecule's interaction with the artificial membrane.

2. **Pyridine Ring**: The pyridine ring is a heteroaromatic structure that can contribute to the molecule's overall stability and ability to interact with biological membranes. The nitrogen atom in the pyridine ring can participate in hydrogen bonding, which may enhance the molecule's permeability.

3. **Phenyl Groups**: The phenyl groups in the structure provide hydrophobic character, which can facilitate the molecule's passage through the lipid-rich regions of the artificial membrane. The balance between hydrophilic and hydrophobic regions is crucial for determining the overall permeability of the molecule.

4. **Thiazole Ring**: The thiazole ring is another heteroaromatic structure that can contribute to the molecule's ability to interact with the artificial membrane. The presence of sulfur and nitrogen in the thiazole ring can enhance the molecule's ability to form hydrogen bonds and ionic interactions.

Overall, the given molecule's combination of polar and non-polar regions, along with its ability to form hydrogen bonds and ionic interactions, suggests that it would have high permeability in the artificial membrane. The balance of hydrophilic and hydrophobic components allows the molecule to effectively traverse the membrane, making it suitable for further biological interactions.

Final answer: High permeability.

------
# 356

**SMILES:** C1=CC=C(C=C1)CNC(=O)C2=NC(=NC=C2Cl)S(=O)(=O)CC3=CC=C(C=C3)F

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a sulfonamide, which is a class of compounds known for their antimicrobial properties. The sulfonamide group is characterized by the presence of a sulfonyl functional group attached to an amine. In this molecule, the sulfonamide group is linked to a pyrimidine ring, which is a heterocyclic aromatic organic compound containing nitrogen atoms.

The presence of the sulfonamide group typically contributes to the molecule's ability to interact with biological targets, such as enzymes or receptors, due to its ability to form hydrogen bonds and ionic interactions. This can enhance the molecule's permeability across biological membranes.

The pyrimidine ring in the given molecule provides a planar, aromatic structure that can facilitate interactions with biological membranes, potentially increasing permeability. The aromatic nature of the pyrimidine ring can also enhance the molecule's ability to pass through lipid bilayers due to its hydrophobic character.

Additionally, the molecule contains a 4-chloro substituent on the pyrimidine ring. Chlorine atoms can increase the lipophilicity of a compound, which may enhance its ability to permeate lipid membranes.

The presence of a fluorophenyl group attached via a methylene bridge introduces a fluorine atom, which is known to increase the metabolic stability of compounds and can also enhance lipophilicity. This can further contribute to the molecule's permeability by increasing its ability to dissolve in lipid environments.

Overall, the combination of the sulfonamide group, pyrimidine ring, chloro substituent, and fluorophenyl group suggests that the given molecule likely exhibits high permeability in the PAMPA assay, allowing it to effectively interact with biological targets.

Final answer: High permeability.

------
# 357

**SMILES:** CCC1=CC(=CC=C1)NS(=O)(=O)C2=CC3=C(C=C2)N(C(C3)C)C(=O)C4CC4

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a sulfonamide, which is a class of compounds known for their antibacterial properties. The sulfonamide group is characterized by the presence of a sulfonyl functional group attached to an amine. This group is known to enhance the molecule's ability to interact with biological membranes, which can influence its permeability.

In the given molecule, the sulfonamide group is attached to a cyclohexene ring, which is a six-membered ring containing a double bond. The presence of this unsaturated ring can contribute to the molecule's lipophilicity, potentially enhancing its ability to permeate lipid membranes.

Additionally, the molecule contains a 1-ethyl-3-methyl-1H-indole moiety. The indole structure is a bicyclic compound consisting of a benzene ring fused to a pyrrole ring. This structure is often associated with increased membrane permeability due to its planar and aromatic nature, which can facilitate passage through lipid bilayers.

The presence of a cyclopropane ring, which is a three-membered carbon ring, can also influence the molecule's conformation and rigidity. Cyclopropane rings are known to introduce strain into the molecular structure, which can affect the molecule's interaction with the artificial membrane.

Overall, the combination of the sulfonamide group, the cyclohexene ring, the indole moiety, and the cyclopropane ring suggests that the given molecule may exhibit high permeability in the PAMPA assay due to its potential for favorable interactions with the artificial membrane.

Final answer: High permeability.

------
# 358

**SMILES:** CC1=CC(=C(N1C2=CC(=CC=C2)Cl)C)C3=NN=C4N3CCCCC4

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several distinct structural components, each contributing to its permeability characteristics in the PAMPA assay.

Firstly, the presence of a chlorophenyl group indicates that the molecule has a hydrophobic aromatic ring with a chlorine substituent. This group can enhance the lipophilicity of the molecule, which generally increases its ability to permeate lipid membranes. The chlorophenyl group can also participate in hydrophobic interactions with the artificial membrane, potentially facilitating passage through the membrane.

Secondly, the molecule contains a trimethyl-dihydropyrazole moiety. The dihydropyrazole ring is a heterocyclic structure that can contribute to the molecule's overall stability and rigidity. The presence of methyl groups on the pyrazole ring increases the hydrophobic character of this part of the molecule, which may further enhance its permeability by promoting interactions with the lipid components of the artificial membrane.

Additionally, the tetrazole ring is a five-membered ring containing nitrogen atoms, which can contribute to the molecule's ability to form hydrogen bonds. While tetrazoles are often polar, their ability to form hydrogen bonds can also facilitate interactions with the polar head groups of the artificial membrane, potentially aiding in permeability.

Overall, the combination of hydrophobic aromatic and aliphatic groups, along with the polar tetrazole ring, suggests that the given molecule is likely to exhibit high permeability in the PAMPA assay. The balance of hydrophobic and polar characteristics allows the molecule to effectively interact with the artificial membrane, promoting its passage through the membrane.

Final answer: High permeability.

------
# 359

**SMILES:** CC1=CC(=C(N1C2=CC=CC(=C2)C(F)(F)F)C)C3=NN=C4N3CCCCC4

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several distinct structural components, each contributing to its permeability characteristics in the PAMPA assay.

Firstly, the presence of the trifluoromethyl group attached to a phenyl ring is significant. This group is known for its electron-withdrawing properties, which can influence the molecule's overall polarity and lipophilicity. The trifluoromethyl group can enhance the lipophilicity of the molecule, potentially increasing its ability to permeate lipid membranes. This is because the group's high electronegativity can reduce the overall polarity of the molecule, making it more compatible with lipid environments.

Secondly, the molecule contains a trimethyl-substituted triazolopyridine moiety. The triazole ring is a five-membered heterocyclic compound containing nitrogen atoms, which can participate in hydrogen bonding and other polar interactions. The presence of methyl groups on the triazole ring can further increase the lipophilicity of the molecule, enhancing its membrane permeability. The pyridine component, being a nitrogen-containing aromatic ring, can also contribute to the molecule's ability to interact with polar environments, although its aromatic nature may also allow for some degree of membrane permeability.

The tetrahydro component of the triazolopyridine indicates partial saturation, which can affect the flexibility and conformation of the molecule. This flexibility might allow the molecule to better adapt to the membrane environment, potentially facilitating its passage through the artificial membrane.

Overall, the combination of lipophilic and polar characteristics in the given molecule suggests that it would exhibit high permeability in the PAMPA assay. The balance of hydrophobic and hydrophilic interactions, along with the structural flexibility provided by the tetrahydro component, likely enables the molecule to effectively traverse the artificial membrane.

Final answer: High permeability.

------
# 360

**SMILES:** C1CCN(C1)C2=NC=C(C=C2)CNC(=O)C3=C(C=CC(=C3)Cl)O

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a monocarboxylic acid amide with a complex structure that includes several functional groups contributing to its permeability characteristics. Let's break down the structural features and their impact on permeability:

1. **Chloro Substituent**: The presence of a chloro group on the benzene ring can influence the molecule's lipophilicity. Chlorine is a relatively electronegative atom, which can increase the molecule's overall hydrophobicity. This can enhance the molecule's ability to interact with the lipid components of the artificial membrane, potentially increasing its permeability.

2. **Hydroxy Group**: The hydroxy group on the benzene ring introduces a polar character to the molecule. This group can form hydrogen bonds with the artificial membrane, which may facilitate interaction and permeation. However, the hydroxy group can also increase the molecule's overall polarity, which might reduce its permeability by limiting its ability to traverse the lipid-rich membrane.

3. **Amide Linkage**: The amide bond is a key structural feature that can influence the molecule's conformation and interaction with the membrane. Amides are generally polar and can participate in hydrogen bonding, which might aid in membrane interaction. However, the presence of the amide group can also introduce some rigidity to the molecule, potentially affecting its ability to fit into the membrane's structure.

4. **Pyridine and Pyrrole Rings**: The pyridine and pyrrole rings contribute to the aromatic character of the molecule. These heterocyclic rings can enhance the molecule's ability to interact with the membrane through π-π stacking interactions. Additionally, the nitrogen atoms in these rings can participate in hydrogen bonding or coordinate with metal ions in the membrane, potentially aiding in permeation.

5. **Pyrrolidine Group**: The pyrrolidine ring is a saturated, secondary amine that can increase the molecule's solubility in water. This group can also enhance the molecule's flexibility, allowing it to adapt to the membrane's structure more effectively. The presence of this group may improve the molecule's permeability by facilitating its passage through the membrane.

Overall, the given molecule's structure suggests a balance between hydrophobic and hydrophilic interactions, which is typical for molecules with moderate permeability in PAMPA assays. The presence of both polar and non-polar groups allows the molecule to interact with the artificial membrane, but the specific arrangement and nature of these groups will determine the extent of its permeability. Therefore, the given molecule is likely to exhibit low-to-moderate permeability in the PAMPA assay.

Final answer: Low-to-moderate permeability.

------
# 361

**SMILES:** COC1=CC=C(C=C1)CN2CCN(CC2)C(=O)C3=CC4=C(S3)CCC4

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several distinct structural components, each contributing to its permeability characteristics in the PAMPA assay.

Firstly, the molecule contains a methoxyphenyl group, which is a phenyl ring substituted with a methoxy group. This aromatic structure is known for its hydrophobic character, which can enhance the molecule's ability to interact with lipid membranes. The presence of the methoxy group can also influence the electronic properties of the phenyl ring, potentially affecting the molecule's overall polarity and solubility.

Secondly, the molecule includes a piperazine ring, which is a six-membered heterocyclic structure containing two nitrogen atoms. Piperazine rings are often associated with basicity due to the presence of nitrogen atoms, which can participate in hydrogen bonding and ionic interactions. This can enhance the molecule's solubility in aqueous environments and may facilitate its interaction with the artificial membrane.

Additionally, the molecule features a thienopyrrole moiety, which is a bicyclic structure combining a thiophene and a pyrrole ring. The presence of sulfur in the thiophene ring can contribute to the molecule's overall lipophilicity, while the pyrrole ring can participate in hydrogen bonding due to its nitrogen atom. This bicyclic system may enhance the molecule's ability to penetrate lipid membranes by increasing its hydrophobic interactions.

The methanone linkage in the molecule acts as a carbonyl group, which can engage in dipole-dipole interactions and hydrogen bonding. This functional group can influence the molecule's overall polarity and may play a role in its interaction with the artificial membrane.

Overall, the combination of hydrophobic aromatic rings, basic piperazine, and the bicyclic thienopyrrole structure suggests that the given molecule is likely to exhibit high permeability in the PAMPA assay. The balance of hydrophobic and hydrophilic properties, along with the potential for hydrogen bonding and ionic interactions, supports its ability to traverse the artificial membrane.

Final answer: High permeability.

------
# 362

**SMILES:** CC1=CC=C(C=C1)S(=O)(=O)NC2=C(C=CN=C2)C(=O)NC3=NC(=CS3)C4=CC(=CC=C4)OC

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a sulfonamide, which is a class of compounds known for their antimicrobial properties. The sulfonamide group is characterized by the presence of a sulfonyl functional group attached to an amine. This group is known to enhance the molecule's ability to interact with biological membranes, which can influence its permeability.

The structure of the given molecule includes several key components that contribute to its permeability:

1. **Sulfonamide Group**: The presence of the sulfonamide moiety, specifically the sulfonyl group attached to the 3-methoxyphenyl ring, is crucial for its permeability. Sulfonamides are known to have moderate permeability due to their ability to form hydrogen bonds and interact with polar environments, such as those found in biological membranes.

2. **Aromatic Rings**: The molecule contains multiple aromatic rings, including a methoxyphenyl group, a pyridine ring, and a thiazole ring. These rings contribute to the molecule's lipophilicity, which can enhance its ability to permeate lipid membranes. However, the presence of polar groups, such as the sulfonamide and amide, can counterbalance this by increasing hydrophilicity.

3. **Amide Linkage**: The carboxamide group in the molecule can form hydrogen bonds, which may facilitate interaction with the artificial membrane. This group can also contribute to the overall polarity of the molecule, affecting its permeability.

4. **Methoxy Group**: The methoxy group on the phenyl ring can increase the molecule's lipophilicity, potentially enhancing its permeability through lipid-rich environments.

Overall, the given molecule's structure suggests that it would have moderate permeability in the PAMPA assay. The balance between its lipophilic aromatic rings and polar functional groups, such as the sulfonamide and amide, likely results in a moderate ability to permeate the artificial membrane.

Final answer: Low-to-moderate permeability.

------
# 363

**SMILES:** CC1=C[C@H]([C@@H](C[C@H]1CC2=NC3=C(N2)C=CC(=N3)OC)C(C)C)CNCC4=CC=CC=C4O

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that includes several functional groups and structural features that influence its permeability in the PAMPA assay. Let's break down these features and their impact on permeability:

1. **Piperidine Ring**: The presence of a piperidine ring, which is a six-membered nitrogen-containing heterocycle, contributes to the molecule's basicity and potential for hydrogen bonding. This can enhance the molecule's solubility in water and its ability to interact with the polar head groups of the artificial membrane, potentially increasing its permeability.

2. **Methoxyphenol Group**: The methoxyphenol moiety introduces both hydrophobic and hydrophilic characteristics. The methoxy group can increase lipophilicity, which may enhance membrane permeability by allowing the molecule to interact with the lipid bilayer of the artificial membrane. However, the phenolic hydroxyl group can form hydrogen bonds, which may also facilitate interaction with the membrane.

3. **Imidazo[4,5-b]pyridine Moiety**: This bicyclic heteroaromatic system is relatively planar and can engage in π-π stacking interactions with the aromatic residues of the artificial membrane. The nitrogen atoms in the imidazole ring can also participate in hydrogen bonding, which may aid in membrane permeation.

4. **Methylamino Linkage**: The methylamino group acts as a bridge between the methoxyphenol and the imidazo[4,5-b]pyridine moieties. This linkage can enhance the molecule's flexibility, allowing it to adopt conformations that optimize interaction with the membrane.

5. **Chirality**: The given molecule has several chiral centers, which can influence its three-dimensional shape and, consequently, its ability to fit into the membrane's structure. The specific stereochemistry may affect the molecule's overall permeability by dictating how it interacts with the membrane.

Overall, the combination of these structural features suggests that the given molecule has a balance of hydrophilic and hydrophobic properties, which can facilitate its passage through the artificial membrane. The presence of multiple functional groups capable of hydrogen bonding and hydrophobic interactions likely enhances its permeability, making it suitable for the PAMPA assay. Therefore, the given molecule is likely to exhibit high permeability in the PAMPA assay.

Final answer: High permeability

------
# 364

**SMILES:** CC1=CC(=CC(=C1)NS(=O)(=O)C2=CC3=C(C=C2)NC=C(C3=O)C(=O)NCC4=CC=CO4)C

**Label:** 0

**Predi:** 1

**Correct:** 0

# Response:
The given molecule is a quinoline derivative with several functional groups that influence its permeability in the PAMPA assay. Let's analyze these groups and their impact on permeability:

1. **Quinoline Core**: The quinoline structure is a bicyclic aromatic compound, which generally contributes to the molecule's lipophilicity. This lipophilic nature can enhance the molecule's ability to permeate through lipid membranes, suggesting high permeability.

2. **Carboxamide Group**: The presence of a carboxamide group can influence the molecule's polarity and hydrogen bonding capabilities. While it may introduce some degree of polarity, the overall effect in this molecule is likely minimal due to the dominant lipophilic quinoline core.

3. **Sulfamoyl Group**: The sulfamoyl group, attached to the quinoline, introduces additional polarity and potential for hydrogen bonding. This group can enhance the molecule's solubility in aqueous environments, which may affect its permeability. However, its impact is balanced by the lipophilic nature of the quinoline core.

4. **3,5-Dimethylphenoxy Group**: This aromatic group adds to the lipophilicity of the molecule, further enhancing its membrane permeability. The presence of methyl groups can also increase steric bulk, potentially affecting the molecule's interaction with the artificial membrane.

5. **Furan-2-ylmethyl Group**: The furan ring is an aromatic heterocycle that contributes to the molecule's overall aromaticity and lipophilicity. This group can enhance the molecule's ability to interact with the lipid components of the artificial membrane, promoting permeability.

Overall, the given molecule's structure, dominated by its quinoline core and various aromatic and lipophilic groups, suggests that it would exhibit high permeability in the PAMPA assay. The balance of polar and non-polar groups allows it to effectively interact with the artificial membrane, facilitating its passage through the membrane.

Final answer: High permeability.

------
# 365

**SMILES:** CCCCC(C)/C=C(\C)/C=C(\C)/C(=O)NC1=CC(C2C(C1=O)O2)(/C=C/C=C/C=C/C(=O)NC3=C(CCC3=O)O)O

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a complex natural product with a variety of functional groups and structural features that influence its permeability in the PAMPA assay. Let's break down the key structural elements and their impact on permeability:

1. **Conjugated Triene System**: The molecule contains a conjugated triene system, which is a series of alternating double bonds. This feature can enhance the molecule's ability to interact with the lipid bilayer of the artificial membrane, potentially increasing its permeability. Conjugated systems can also contribute to the molecule's overall stability and rigidity, which may affect its ability to traverse the membrane.

2. **Hydroxy Groups**: The presence of hydroxy groups in the molecule can increase its hydrophilicity, which may enhance its solubility in aqueous environments. However, these groups can also form hydrogen bonds with the artificial membrane, potentially facilitating or hindering permeability depending on the specific interactions.

3. **Amide Linkage**: The amide group in the molecule is a polar functional group that can participate in hydrogen bonding. This can influence the molecule's interaction with the membrane, potentially affecting its permeability. Amides are generally considered to have moderate permeability due to their ability to form hydrogen bonds.

4. **Bicyclic Structure**: The bicyclic structure, specifically the oxabicycloheptene moiety, adds rigidity to the molecule. This rigidity can affect the molecule's ability to fit into the membrane's lipid bilayer, potentially influencing its permeability. Bicyclic structures can also impact the molecule's overall three-dimensional shape, which is crucial for membrane interaction.

5. **Ketone Groups**: The presence of multiple ketone groups can increase the molecule's polarity and ability to form hydrogen bonds. These groups can interact with the membrane, potentially affecting permeability. However, they may also create steric hindrance that could limit membrane passage.

Overall, the given molecule's permeability in the PAMPA assay is likely influenced by a combination of its hydrophilic and hydrophobic interactions, rigidity due to its bicyclic structure, and the presence of multiple functional groups that can form hydrogen bonds. These factors suggest that the molecule may have moderate permeability, balancing between hydrophilic and hydrophobic interactions with the artificial membrane.

Final answer: Low-to-moderate permeability.

------
# 366

**SMILES:** CC(C)C1=CC=C(C=C1)OCC2=NC3=C(N2CC4=CC=CC=C4)C(=O)N(CCN3)CCOC

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound with several functional groups and structural features that influence its permeability in the PAMPA assay. Let's analyze these features:

1. **Imidazo[1,2-a]pyrazine Core**: This bicyclic structure is a fused heterocyclic system that contributes to the rigidity and planarity of the molecule. Such structures are often involved in interactions with biological membranes, and their planar nature can facilitate passage through lipid bilayers. However, the presence of nitrogen atoms in the rings can also introduce hydrogen bonding capabilities, which may affect permeability.

2. **Benzyl Group**: The benzyl group is a hydrophobic moiety that can enhance the lipophilicity of the molecule. This increased lipophilicity can improve the molecule's ability to permeate lipid membranes, as it can interact with the hydrophobic tails of the lipid bilayer.

3. **Phenylmethoxyphenyl Group**: This group introduces additional aromaticity and hydrophobic character to the molecule. The methoxy group can also contribute to the molecule's overall polarity, potentially affecting its solubility and permeability. The presence of two phenyl rings can enhance the molecule's ability to interact with the lipid bilayer through π-π interactions.

4. **Methoxymethyl Group**: This group is a polar moiety that can increase the molecule's solubility in aqueous environments. It may also participate in hydrogen bonding, which can influence the molecule's interaction with the artificial membrane.

5. **Isopropyl Group**: The isopropyl group is another hydrophobic moiety that can enhance lipophilicity, aiding in membrane permeability.

Overall, the given molecule has a balance of hydrophobic and hydrophilic features, with a significant number of aromatic and lipophilic groups. These characteristics suggest that the molecule would have moderate to high permeability in the PAMPA assay, as it can effectively interact with the lipid components of the artificial membrane while also being soluble enough to traverse the membrane.

Final answer: High permeability

------
# 367

**SMILES:** CC(=O)C1=C(N=C(S1)NC(=O)C2=CC=CO2)C3=CC=CC=C3

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several functional groups and structural elements that influence its permeability in the PAMPA assay. Let's break down the key components and their impact on permeability:

1. **Thiazole Ring**: The presence of a thiazole ring, which is a five-membered heterocyclic compound containing both sulfur and nitrogen, contributes to the molecule's overall stability and rigidity. Thiazole rings are known for their ability to participate in hydrogen bonding and π-π interactions, which can enhance the molecule's ability to interact with the artificial membrane. This interaction can facilitate permeation, suggesting that the given molecule might exhibit high permeability.

2. **Acetyl Group**: The acetyl group attached to the thiazole ring introduces a polar character to the molecule. This group can engage in hydrogen bonding, which may enhance the molecule's solubility in aqueous environments and improve its interaction with the membrane. This could also contribute to moderate permeability, as the polar nature of the acetyl group can balance the hydrophobic interactions.

3. **Phenyl Group**: The phenyl group is a hydrophobic aromatic ring that can engage in π-π stacking interactions with the membrane. This hydrophobic interaction can enhance the molecule's permeability by allowing it to embed within the lipid bilayer of the artificial membrane. However, the presence of the phenyl group may also contribute to a balance between hydrophobic and hydrophilic interactions, potentially leading to moderate permeability.

4. **Furan-2-carboxamide Moiety**: The furan ring is another aromatic heterocycle that can participate in π-π interactions, similar to the phenyl group. The carboxamide group attached to the furan ring introduces additional hydrogen bonding capabilities, which can enhance solubility and membrane interaction. This moiety can contribute to the overall balance of hydrophobic and hydrophilic interactions, potentially leading to moderate permeability.

In summary, the given molecule contains a combination of aromatic and heterocyclic rings, along with polar functional groups, which collectively suggest a balance of hydrophobic and hydrophilic interactions. These features are likely to facilitate moderate to high permeability in the PAMPA assay, allowing the molecule to effectively interact with the artificial membrane.

Final answer: High permeability.

------
# 368

**SMILES:** CCOC1=C(C(=C(C=C1)CCNC(=O)C2=CC3=C(N2CC4=CC=CC=C4)C=CS3)F)OCC

**Label:** 0

**Predi:** 0

**Correct:** 1

# Response:
The given molecule is a complex organic compound that includes several functional groups and structural features that influence its permeability in the PAMPA assay. Let's break down these features and their impact on permeability:

1. **Thieno[3,2-b]pyrrole Core**: This bicyclic structure is a fused ring system that combines a thiophene and a pyrrole ring. The presence of sulfur in the thiophene ring can enhance lipophilicity, which generally increases membrane permeability. However, the overall rigidity and planarity of the fused ring system can also affect how the molecule interacts with the membrane, potentially limiting its permeability due to steric hindrance.

2. **Carboxamide Group**: The carboxamide group is a polar functional group that can form hydrogen bonds with the artificial membrane. This can increase the molecule's affinity for the membrane, potentially enhancing its permeability. However, the presence of this group also introduces some degree of polarity, which can counteract the lipophilic effects of the thiophene ring.

3. **N-(2-(2,4-difluorophenyl)ethyl) Substituent**: The difluorophenyl group is a phenyl ring substituted with two fluorine atoms. Fluorine atoms are highly electronegative, which can increase the molecule's overall polarity. This can decrease permeability by reducing the molecule's ability to dissolve in the lipid bilayer of the membrane. However, the ethyl linker provides some flexibility, which might help the molecule to adapt to the membrane structure.

4. **Phenylmethoxyphenyl Group**: This group consists of a phenyl ring attached to a methoxy group, which is further connected to another phenyl ring. The methoxy group is an electron-donating group that can increase lipophilicity, potentially enhancing membrane permeability. The presence of two phenyl rings can also contribute to the molecule's overall hydrophobic character, which is favorable for permeability.

Overall, the given molecule has both lipophilic and polar characteristics. The thiophene-pyrrole core and phenylmethoxyphenyl group contribute to its lipophilicity, which generally supports high permeability. However, the presence of polar groups, such as the carboxamide and difluorophenyl substituent, can introduce some degree of polarity, potentially limiting its permeability. In the context of the PAMPA assay, these factors suggest that the given molecule likely exhibits a balance of high and low permeability, leaning towards a moderate permeability profile.

Final answer: Low-to-moderate permeability.

------
# 369

**SMILES:** COC1=C(C(=C(C=C1)C2=CC3=C(C=C2)N=C(O3)C4=CC=C(C=C4)SC)OC)OC

**Label:** 0

**Predi:** 1

**Correct:** 0

# Response:
The given molecule is a member of the benzoxazole family, which is characterized by a fused benzene and oxazole ring. This structural feature is often associated with a degree of rigidity and planarity, which can influence the molecule's interaction with biological membranes.

The presence of the trimethoxyphenyl group, which consists of a phenyl ring substituted with three methoxy groups, contributes to the molecule's lipophilicity. Methoxy groups are electron-donating and can enhance the molecule's ability to interact with lipid environments, potentially increasing its permeability through the lipid bilayer of a biological membrane.

Additionally, the methylthio group attached to the phenyl ring introduces a sulfur atom, which can further influence the molecule's lipophilicity and electronic properties. Sulfur-containing groups are known to enhance membrane permeability due to their ability to engage in hydrophobic interactions and potentially form weak hydrogen bonds with the lipid bilayer.

Overall, the combination of the benzoxazole core, the trimethoxyphenyl group, and the methylthio group suggests that the given molecule is likely to exhibit high permeability through the artificial membrane, as these structural features enhance its lipophilicity and ability to interact with lipid environments.

Final answer: High permeability.

------
# 370

**SMILES:** CC1=CC=C(C=C1)CCNC(=O)C2CCCN(C2)C(=O)C3=CC4=C(N3C)C=CS4

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several distinct structural components, each contributing to its permeability characteristics in the PAMPA assay.

1. **Thieno[3,2-b]pyrrole Core**: This bicyclic structure is a fusion of a thiophene ring and a pyrrole ring. The presence of sulfur in the thiophene ring and nitrogen in the pyrrole ring can enhance the molecule's ability to interact with the artificial membrane, potentially increasing its permeability. The aromatic nature of these rings can facilitate π-π interactions with the membrane, which may aid in permeation.

2. **Methyl Substituents**: The methyl groups attached to the thieno[3,2-b]pyrrole core and the phenyl ring can increase the hydrophobic character of the molecule. This hydrophobicity can enhance the molecule's ability to traverse lipid membranes, contributing to higher permeability.

3. **Amide Linkage**: The presence of an amide bond in the molecule, specifically the carboxamide group attached to the piperidine ring, can influence its permeability. Amide bonds are relatively polar, which can affect the solubility and permeability balance. In PAMPA, the amide linkage may facilitate hydrogen bonding with the membrane, potentially aiding in permeation.

4. **Piperidine Ring**: The piperidine ring is a saturated nitrogen-containing heterocycle that can enhance the molecule's basicity and solubility. This can improve the molecule's interaction with the polar head groups of the artificial membrane, potentially increasing its permeability.

5. **Phenyl Ring with Methyl Substituent**: The phenyl ring, substituted with a methyl group, contributes to the overall hydrophobic character of the molecule. This can enhance the molecule's ability to interact with the lipid components of the artificial membrane, promoting permeability.

Overall, the given molecule's combination of aromatic rings, hydrophobic substituents, and polar functional groups suggests that it would exhibit high permeability in the PAMPA assay. The balance of hydrophobic and polar characteristics allows the molecule to effectively interact with the artificial membrane, facilitating its passage through the membrane.

Final answer: High permeability

------
# 371

**SMILES:** CCN1C2=C(C=C1C(=O)N3CCCC(C3)C(=O)NCCC4=CC=C(C=C4)C)SC=C2

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several distinct structural components, each contributing to its permeability characteristics in the PAMPA assay.

1. **Thieno[3,2-b]pyrrole Core**: This bicyclic structure is a fusion of a thiophene ring and a pyrrole ring. The presence of sulfur in the thiophene ring can enhance lipophilicity, which often correlates with increased membrane permeability. The aromatic nature of both rings can facilitate interactions with the lipid bilayer of the artificial membrane, potentially enhancing permeability.

2. **Ethyl Substituent**: The ethyl group attached to the thieno[3,2-b]pyrrole core increases the hydrophobic character of the molecule. This can further enhance the molecule's ability to traverse lipid membranes by increasing its solubility in the lipid bilayer.

3. **Piperidine Carboxamide Moiety**: The piperidine ring is a saturated nitrogen-containing heterocycle, which can contribute to the molecule's basicity and ability to form hydrogen bonds. The carboxamide group can also participate in hydrogen bonding, which may influence the molecule's interaction with the artificial membrane. However, the presence of the piperidine ring may also introduce some steric hindrance, potentially limiting permeability.

4. **4-Ethylphenyl Group**: This aromatic group is attached to the piperidine ring via an ethyl linker. The phenyl ring can enhance lipophilicity, similar to the thieno[3,2-b]pyrrole core, and may also participate in π-π interactions with the membrane. The ethyl linker provides some flexibility, which might help the molecule to adapt its conformation to fit into the membrane.

Overall, the given molecule's structure suggests that it has a balance of hydrophobic and hydrophilic properties, with several aromatic and heterocyclic components that can interact with the artificial membrane. These features likely contribute to a moderate to high permeability in the PAMPA assay, as the molecule can effectively partition into the lipid bilayer while also engaging in specific interactions with the membrane.

Final answer: High permeability

------
# 372

**SMILES:** CCOC1=C(C=C(C=C1)CCNC(=O)C2=NC3=CC=CC=C3C=C2)OCC

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a member of quinolines, which are known for their aromatic and heterocyclic structure. This particular molecule features a quinoline core, which is a bicyclic structure consisting of a benzene ring fused to a pyridine ring. This core is known for its planar and aromatic nature, which can facilitate interactions with biological membranes.

Attached to the quinoline core is a carboxamide group, which is a functional group containing a carbonyl group linked to a nitrogen atom. This group can participate in hydrogen bonding, which may influence the molecule's solubility and permeability.

The molecule also contains a 3,4-diethoxyphenyl group. The presence of ethoxy groups (ether functionalities) on the phenyl ring increases the lipophilicity of the molecule. This can enhance the molecule's ability to traverse lipid membranes, as increased lipophilicity often correlates with better membrane permeability.

The ethyl linkage between the diethoxyphenyl group and the quinoline core provides flexibility, which may allow the molecule to adapt its conformation to fit into the membrane's structure, potentially enhancing its permeability.

Overall, the combination of the aromatic quinoline core, the hydrogen bonding potential of the carboxamide group, and the lipophilic ethoxy groups suggests that the given molecule likely exhibits high permeability in the artificial membrane of the PAMPA assay.

Final answer: High permeability

------
# 373

**SMILES:** CC1=CC=C(C=C1)OCCN2C3=CC=CC=C3N=C2CCNC(=O)N4CCCCC4

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a member of the benzimidazole class, which is known for its ability to interact with biological membranes due to its planar aromatic structure. This class of compounds often exhibits good permeability across biological membranes, which is a desirable property for drug molecules as it can enhance bioavailability.

The structure of the given molecule includes a benzimidazole core, which is a bicyclic compound consisting of a benzene ring fused to an imidazole ring. This core is known for its stability and ability to participate in hydrogen bonding and π-π interactions, which can facilitate passage through lipid membranes.

Additionally, the molecule contains a piperidine ring, which is a six-membered nitrogen-containing heterocycle. Piperidine rings are commonly found in pharmaceuticals and can enhance the solubility and permeability of the compound due to their basic nature and ability to form hydrogen bonds.

The presence of a 4-methylphenoxyethyl group attached to the piperidine ring introduces a hydrophobic moiety, which can further enhance membrane permeability by increasing lipophilicity. This group can interact with the lipid bilayer of the membrane, promoting passive diffusion.

Overall, the combination of the benzimidazole core, piperidine ring, and hydrophobic substituents suggests that the given molecule likely exhibits high permeability in the PAMPA assay, allowing it to effectively traverse the artificial membrane.

Final answer: High permeability.

------
# 374

**SMILES:** CCOC(=O)C1=CC=C(C=C1)N2C=NC3=C2C=CC(=C3)C(=O)N4CCCCC4

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that includes several functional groups and structural features that influence its permeability in the PAMPA assay. Let's break down these features and their impact on permeability:

1. **Benzimidazole Core**: The presence of a benzimidazole moiety is significant. Benzimidazole is a bicyclic structure that consists of a benzene ring fused to an imidazole ring. This core is known for its planar structure, which can facilitate interactions with the artificial membrane. The aromatic nature of the benzene ring can also contribute to π-π stacking interactions with the membrane, potentially enhancing permeability.

2. **Piperidine Moiety**: The piperidine ring is a six-membered nitrogen-containing heterocycle. This group is relatively flexible and can increase the molecule's solubility in aqueous environments, which is beneficial for permeability. The presence of the piperidine ring can also enhance the molecule's ability to interact with the membrane through hydrogen bonding or dipole interactions.

3. **Ester Group**: The ester functional group, specifically the ethyl ester, is present in the molecule. Esters are generally polar and can participate in hydrogen bonding with the membrane. However, esters can also be susceptible to hydrolysis, which might affect the stability of the molecule in the PAMPA assay. The presence of the ester group may contribute to moderate permeability, as it can enhance solubility but also introduce some degree of hydrolytic instability.

4. **Benzoate Ester**: The benzoate ester is another polar functional group that can interact with the membrane through hydrogen bonding. This group can also contribute to the overall solubility of the molecule, potentially enhancing its permeability.

Overall, the given molecule contains a combination of aromatic, heterocyclic, and ester groups that contribute to its permeability. The benzimidazole core and piperidine moiety likely enhance interactions with the membrane, while the ester groups contribute to solubility and potential hydrolysis. These features suggest that the given molecule would exhibit high permeability in the PAMPA assay.

Final answer: High permeability

------
# 375

**SMILES:** CC1=CC(=C(N1)C(=O)NC2=CC(=CC=C2)[S+](=O)(N3CCCCCC3)[O-])C

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a complex organic compound that features several functional groups and structural elements that influence its permeability in the PAMPA assay. Let's break down these features and their impact on permeability:

1. **Aromatic Amide Group**: The presence of an aromatic amide group, which includes a carboxamide linked to a phenyl ring, contributes to the molecule's ability to participate in hydrogen bonding and π-π interactions. These interactions can enhance the molecule's affinity for the artificial membrane, potentially increasing its permeability. However, the amide group can also introduce some degree of rigidity and polarity, which might limit its permeability depending on the membrane's properties.

2. **Dimethylphenyl Group**: The dimethyl substitution on the phenyl ring increases the hydrophobic character of the molecule. This hydrophobicity can enhance the molecule's ability to traverse lipid membranes, suggesting higher permeability. However, the balance between hydrophobic and hydrophilic properties will determine the overall permeability.

3. **Pyrrole Ring**: The pyrrole ring is a heterocyclic aromatic compound that can contribute to the molecule's overall aromaticity and electron-rich nature. This can facilitate interactions with the membrane, potentially enhancing permeability. However, the pyrrole ring's nitrogen atom can also introduce polarity, which might affect permeability depending on the membrane's polarity.

4. **Sulfonyl Group**: The sulfonyl group attached to the phenyl ring is highly polar and can significantly increase the molecule's overall polarity. This group can enhance solubility in aqueous environments, which is beneficial for permeability in PAMPA assays. However, it can also hinder permeability if the membrane is predominantly hydrophobic.

5. **Piperidinyl Group**: The piperidinyl group is a saturated nitrogen-containing heterocycle that can increase the molecule's basicity and polarity. This group can enhance solubility and potentially improve permeability by interacting with polar sites on the membrane.

Overall, the given molecule's permeability is influenced by a balance of hydrophobic and hydrophilic interactions, aromaticity, and the presence of polar functional groups. The combination of these features suggests that the molecule may exhibit moderate permeability in the PAMPA assay, as it has both hydrophobic and hydrophilic characteristics, as well as the ability to engage in various interactions with the artificial membrane.

Final answer: Low-to-moderate permeability.

------
# 376

**SMILES:** CCOC1=C(C=C(C=C1)CCNC(=O)C2=CC3=CC=CC=C3N2CC4=CC(=CC(=N4)C)C)OCC

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several distinct structural components, each contributing to its permeability characteristics in the PAMPA assay.

1. **Indole Core**: The presence of the indole moiety is significant. Indole is a bicyclic structure consisting of a benzene ring fused to a pyrrole ring. This structure is relatively planar and hydrophobic, which can facilitate membrane permeability due to its ability to interact with lipid bilayers. The indole core is often found in bioactive compounds, suggesting that the given molecule may have favorable interactions with biological membranes.

2. **Carboxamide Group**: The carboxamide functional group is polar and can form hydrogen bonds. This group can enhance the solubility of the molecule in aqueous environments, which is beneficial for permeability. However, the balance between hydrophilic and hydrophobic properties will determine the overall permeability.

3. **Pyridine Ring**: The pyridine ring is a heteroaromatic structure that can also contribute to the molecule's ability to permeate membranes. Pyridine rings are known for their ability to engage in π-π interactions and hydrogen bonding, which can enhance binding to membrane components.

4. **Substituents on the Pyridine Ring**: The methyl and ethyl groups attached to the pyridine ring increase the hydrophobic character of the molecule. These alkyl groups can enhance the lipophilicity, which is often associated with increased membrane permeability.

5. **Ethoxy and Dimethylphenyl Groups**: The ethoxy group and the dimethylphenyl group attached to the phenyl ring increase the lipophilicity of the molecule. These groups can enhance the ability of the molecule to interact with the lipid components of the membrane, potentially increasing permeability.

Overall, the given molecule's structure suggests that it has a balance of hydrophobic and hydrophilic properties, which is typical for molecules with moderate to high permeability in PAMPA assays. The indole core, along with the various substituents, likely contribute to its ability to traverse the artificial membrane, making it suitable for further evaluation in drug discovery processes.

Final answer: High permeability

------
# 377

**SMILES:** CC(C)N(CCC(=O)C1=CC2=CC=CC=C2C=C1)CC3=CC=CC=C3

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a member of the naphthalene family, which indicates that it contains a naphthalene moiety. This aromatic hydrocarbon structure is known for its planar and hydrophobic characteristics, which can influence the molecule's permeability.

The molecule also contains a propanone group, which is a ketone functional group. Ketones can increase the polarity of a molecule, potentially affecting its permeability by interacting with the polar components of the artificial membrane.

Additionally, the molecule features a benzyl group attached to a nitrogen atom, forming a benzylamino moiety. This group can enhance the lipophilicity of the molecule, which may facilitate its passage through the lipid-rich environment of the artificial membrane.

The presence of a propan-2-yl group attached to the nitrogen atom further contributes to the molecule's hydrophobic character, potentially increasing its permeability by enhancing its solubility in lipid environments.

Overall, the combination of the naphthalene moiety, the ketone group, and the benzylamino moiety suggests that the given molecule likely exhibits high permeability through the artificial membrane due to its overall hydrophobic and lipophilic nature.

Final answer: High permeability.

------
# 378

**SMILES:** CCOC1=CC=CC=C1CNS(=O)(=O)C2=CC=C(C=C2)C3=CN=C(O3)C4CC4

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several distinct functional groups and structural motifs, each contributing to its permeability characteristics in the PAMPA assay.

1. **Oxazole Ring**: The presence of the oxazole ring, a five-membered heterocyclic structure containing both oxygen and nitrogen, is significant. Oxazole rings are known for their planar structure and ability to participate in hydrogen bonding. This can enhance the molecule's ability to interact with the artificial membrane, potentially increasing its permeability.

2. **Cyclopropyl Group**: The cyclopropyl group is a small, three-membered ring that introduces a degree of rigidity and strain to the molecule. This can affect the molecule's overall conformation and its ability to fit into the membrane pores. The cyclopropyl group may also influence the lipophilicity of the molecule, which is crucial for permeability.

3. **Ethoxyphenyl Moiety**: The ethoxy group attached to the phenyl ring increases the lipophilicity of the molecule. This can enhance the molecule's ability to traverse lipid membranes, contributing to higher permeability. The phenyl ring itself can also participate in π-π interactions with the membrane, further aiding in permeation.

4. **Benzene Sulfonamide**: The sulfonamide group is a polar functional group that can form hydrogen bonds with the membrane. While it may introduce some degree of polarity that could hinder permeability, its presence is often balanced by the lipophilic nature of the surrounding groups. The sulfonamide group can also contribute to the molecule's solubility, which is important for its interaction with the membrane.

Overall, the given molecule's structure suggests a balance between lipophilic and polar characteristics, with the oxazole and phenyl groups potentially enhancing membrane interaction and permeability. The cyclopropyl and ethoxy groups contribute to lipophilicity, while the sulfonamide group provides a degree of polarity. These features collectively suggest that the given molecule would exhibit high permeability in the PAMPA assay.

Final answer: High permeability

------
# 379

**SMILES:** CCOC1=C(C=C(C=C1)CCNC(=O)C2=CC3=C(N2C)C=CS3)OCC

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several functional groups and structural elements that influence its permeability in the PAMPA assay. Let's break down the key components and their impact on permeability:

1. **Thieno[3,2-b]pyrrole Core**: This bicyclic structure is a heterocyclic compound containing both sulfur and nitrogen atoms. The presence of these heteroatoms can enhance the molecule's ability to interact with the artificial membrane, potentially increasing its permeability. The aromatic nature of the thieno[3,2-b]pyrrole ring system can also contribute to lipophilicity, which is often associated with higher membrane permeability.

2. **Methyl Substitution**: The methyl group attached to the thieno[3,2-b]pyrrole core can increase the hydrophobic character of the molecule. This can enhance the molecule's ability to traverse lipid membranes, contributing to higher permeability.

3. **Carboxamide Group**: The carboxamide functional group is polar and can form hydrogen bonds with the artificial membrane. While this can provide some degree of interaction with the membrane, it may also introduce some degree of polarity that could limit permeability. However, in this molecule, the presence of the carboxamide is likely balanced by the hydrophobic and aromatic components.

4. **Ethoxyphenyl Group**: The ethoxyphenyl moiety introduces additional aromaticity and hydrophobicity to the molecule. The ethoxy group can also contribute to the overall lipophilicity, which is generally favorable for membrane permeability. The presence of this group suggests that the molecule may have a favorable balance of hydrophilic and hydrophobic properties, enhancing its ability to permeate the artificial membrane.

Overall, the given molecule's structure suggests that it has a balance of hydrophobic and hydrophilic properties, with significant aromatic and heteroatom content. This combination is likely to result in high permeability in the PAMPA assay, as the molecule can effectively interact with the artificial membrane while maintaining sufficient lipophilicity for permeation.

Final answer: High permeability.

------
# 380

**SMILES:** COC1=CC=CC(=C1O)CNC2=CC=C(C=C2)S(=O)(=O)NC3=CC=CS3

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a sulfonamide, which is a class of compounds known for their antibacterial properties. The sulfonamide group is characterized by the presence of a sulfonyl functional group attached to an amine. This group is known to enhance the molecule's ability to interact with biological targets, such as enzymes or receptors, due to its polar nature and ability to form hydrogen bonds.

In the given molecule, the sulfonamide group is attached to a phenyl ring, which is further substituted with a hydroxy-methoxyphenyl group. The presence of the hydroxy and methoxy groups increases the molecule's polarity and potential for hydrogen bonding, which can enhance its solubility and interaction with the artificial membrane.

The thiophen-2-ylsulfonamide moiety introduces a heterocyclic component, which can contribute to the molecule's overall lipophilicity. Thiophene rings are known for their aromatic stability and can enhance the molecule's ability to penetrate lipid membranes due to their planar structure.

Overall, the combination of polar and non-polar groups in the given molecule suggests that it may have moderate permeability through the artificial membrane. The sulfonamide group and hydroxy-methoxy substitutions increase its polarity, potentially aiding in solubility and interaction with the membrane, while the thiophene ring may contribute to lipophilicity, allowing some degree of membrane permeability. Therefore, the given molecule is likely to exhibit low-to-moderate permeability in the Parallel Artificial Membrane Permeability Assay (PAMPA).

Final answer: Low-to-moderate permeability.

------
# 381

**SMILES:** CC1=CC(=C(C=C1Cl)OC)NS(=O)(=O)C2=C(N=C3N(C2=O)C=CS3)C

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a sulfonamide, which is a class of compounds known for their antimicrobial properties. The sulfonamide group is characterized by the presence of a sulfonyl functional group attached to an amine. This group is known to enhance the molecule's ability to interact with biological targets, often through hydrogen bonding and ionic interactions.

The structure of the given molecule includes several key features that influence its permeability:

1. **Sulfonamide Group**: The presence of the sulfonamide group contributes to the molecule's polarity and ability to form hydrogen bonds. This can enhance its solubility in aqueous environments and facilitate interactions with polar sites on biological membranes.

2. **Aromatic Rings**: The molecule contains multiple aromatic rings, including a chlorinated and methoxy-substituted phenyl ring and a thiazolopyrimidine core. Aromatic rings can enhance lipophilicity, which may aid in membrane permeability by allowing the molecule to interact with the lipid bilayer of the membrane.

3. **Chlorine and Methoxy Substituents**: The chloro and methoxy groups on the phenyl ring can influence the electronic properties of the ring, potentially affecting the molecule's ability to penetrate the membrane. The chloro group can increase lipophilicity, while the methoxy group can enhance solubility and influence the electronic distribution.

4. **Thiazolopyrimidine Core**: This heterocyclic core is relatively planar and can interact with the membrane through π-π stacking interactions. The presence of nitrogen and sulfur atoms in the core can also contribute to hydrogen bonding and ionic interactions with the membrane.

Overall, the combination of polar and non-polar features in the given molecule suggests that it may have moderate permeability through the artificial membrane. The sulfonamide group and aromatic rings contribute to its ability to interact with the membrane, while the substituents on the phenyl ring and the thiazolopyrimidine core modulate its solubility and electronic properties.

Final answer: Low-to-moderate permeability.

------
# 382

**SMILES:** C1=CC=NC(=C1)C2=NC(=CC(=O)N2)CSC3=CC=C(C=C3)Cl

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a pyrimidine derivative with a complex structure that includes several functional groups and aromatic rings. To predict its permeability in the PAMPA assay, we need to consider the following structural features:

1. **Aromatic Rings**: The molecule contains a pyridine ring and a chlorophenyl group. Aromatic rings generally contribute to lipophilicity, which can enhance membrane permeability. The presence of these rings suggests that the molecule may have a degree of hydrophobic character, aiding in its ability to traverse lipid membranes.

2. **Chlorophenyl Group**: The chlorophenyl moiety introduces a chlorine atom, which can influence the electronic properties of the molecule. Chlorine is electronegative and can affect the molecule's overall polarity. This substitution may enhance the molecule's ability to interact with the lipid bilayer of the artificial membrane, potentially increasing permeability.

3. **Pyrimidinone Core**: The pyrimidinone core is a heterocyclic aromatic compound that can participate in hydrogen bonding and other non-covalent interactions. This core structure is relatively planar and can facilitate stacking interactions with the lipid components of the membrane, which may contribute to permeability.

4. **Methylthio Linkage**: The methylthio linkage connects the chlorophenyl group to the pyrimidinone core. Sulfur atoms can enhance lipophilicity and may also participate in specific interactions with the membrane, such as van der Waals forces or polar interactions.

Overall, the given molecule's combination of aromatic rings, the chlorophenyl group, and the pyrimidinone core suggests that it may have moderate to high permeability in the PAMPA assay. The balance of hydrophobic and polar characteristics, along with the potential for non-covalent interactions, supports its ability to permeate the artificial membrane.

Final answer: High permeability

------
# 383

**SMILES:** CCOC1=C(C=C(C=C1)CCNC(=O)C2=CC=NN2CC3=CC=CC(=C3)C)OCC

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a complex organic compound that features several functional groups and structural elements that influence its permeability in the PAMPA assay. Let's break down the key components and their impact on permeability:

1. **Aromatic Rings**: The molecule contains two aromatic rings: a dimethoxyphenyl group and a phenyl group. Aromatic rings are generally hydrophobic, which can enhance the molecule's ability to interact with the lipid components of the artificial membrane, promoting permeability. However, the presence of additional substituents can modify this effect.

2. **Dimethoxy Substituents**: The dimethoxy groups on the phenyl ring increase the molecule's overall hydrophobicity, which can enhance membrane permeability by increasing the molecule's ability to dissolve in the lipid bilayer of the artificial membrane.

3. **Ethyl Linker**: The ethyl chain connecting the dimethoxyphenyl group to the rest of the molecule provides flexibility and spatial separation, which can influence the molecule's ability to fit into the membrane and interact with the lipid bilayer.

4. **Pyrazole Ring**: The pyrazole ring is a heterocyclic aromatic compound that can contribute to the molecule's overall stability and rigidity. This ring can also participate in hydrogen bonding and other non-covalent interactions with the membrane, potentially affecting permeability.

5. **Carboxamide Group**: The carboxamide group is polar and can form hydrogen bonds with the artificial membrane. This group can enhance the molecule's solubility in aqueous environments, which is important for permeability. However, its presence may also introduce some degree of polarity that could hinder permeability if it interacts too strongly with the aqueous phase.

6. **Methylphenyl Group**: The methyl group on the phenyl ring adds to the hydrophobic character of the molecule, which can enhance permeability by increasing lipid solubility.

Overall, the given molecule's structure suggests that it has a balance of hydrophobic and hydrophilic properties, which is typical for molecules with moderate permeability in PAMPA assays. The aromatic rings and hydrophobic substituents likely promote interaction with the lipid membrane, while the polar carboxamide group may facilitate some aqueous interactions. This combination of features suggests that the molecule would exhibit moderate permeability in the PAMPA assay.

Final answer: Low-to-moderate permeability.

------
# 384

**SMILES:** C1=CC=C(C(=C1)CS(=O)(=O)C2=NC=C(C(=N2)C(=O)NC3=CC=CC=C3F)Cl)F

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a sulfonamide, which is a class of compounds known for their antimicrobial properties. The sulfonamide group is characterized by the presence of a sulfonyl functional group attached to an amine. In this molecule, the sulfonamide group is linked to a pyrimidine ring, which is a heterocyclic aromatic organic compound containing nitrogen atoms.

The presence of the sulfonamide group suggests that the given molecule may have moderate permeability in the PAMPA assay. Sulfonamides are generally polar due to the presence of the sulfonyl group, which can form hydrogen bonds with the artificial membrane. This polarity can facilitate interactions with the membrane, potentially allowing the molecule to permeate to some extent.

Additionally, the molecule contains a 2-fluorophenyl group and a 2-fluorophenyl sulfonyl moiety. The fluorine atoms can increase the lipophilicity of the molecule, which may enhance its ability to permeate the membrane by increasing its affinity for the lipid components of the artificial membrane.

However, the presence of a chlorine atom on the pyrimidine ring may also influence the permeability. Chlorine is a relatively large halogen, and its presence can increase the steric hindrance, potentially reducing the overall permeability of the molecule.

Overall, the balance of polar and non-polar characteristics, along with the specific functional groups present, suggests that the given molecule may exhibit low-to-moderate permeability in the PAMPA assay.

Final answer: Low-to-moderate permeability.

------
# 385

**SMILES:** CCCC1=NC2=C(C=CC(=C2)C(=O)NC3CCCCC3)SC4=C1C=C(C=C4)C

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a dibenzothiazepine, which is a tricyclic compound consisting of two benzene rings fused to a thiazepine ring. This structural framework is known for its rigidity and planarity, which can influence the molecule's ability to permeate biological membranes.

The presence of the carboxamide group in the molecule suggests potential hydrogen bonding capabilities, which can enhance interactions with the artificial membrane. This functional group can form hydrogen bonds with the membrane's polar head groups, potentially increasing permeability.

The cyclohexyl group attached to the nitrogen atom of the carboxamide can increase the lipophilicity of the molecule. This lipophilic character can facilitate the passage of the molecule through the lipid bilayer of the artificial membrane, enhancing permeability.

Additionally, the methyl group on the benzothiazepine ring can contribute to the overall hydrophobicity of the molecule, further promoting its ability to permeate the membrane.

Overall, the combination of these structural features suggests that the given molecule likely exhibits high permeability in the Parallel Artificial Membrane Permeability Assay (PAMPA).

Final answer: High permeability

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# 386

**SMILES:** CC1CCN(CC1)S(=O)(=O)C2=CC3=C(C=C2)N(C(=O)C=C3)CC(=O)NCC4=CC=C(C=C4)Cl

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a complex organic compound that features several functional groups and structural elements that influence its permeability in the PAMPA assay. Let's break down these features and their impact on permeability:

1. **Quinoline Core**: The presence of a quinoline moiety contributes to the molecule's aromaticity and planarity. Quinoline derivatives are known for their ability to interact with biological membranes, often enhancing permeability due to their lipophilic nature. This aromatic system can facilitate passage through the lipid bilayer of the artificial membrane.

2. **Sulfonamide Group**: The sulfonyl group attached to the piperidine ring introduces a polar character to the molecule. Sulfonamides are known for their ability to form hydrogen bonds, which can enhance solubility in aqueous environments and potentially improve interaction with the polar head groups of the artificial membrane.

3. **Piperidine Ring**: The piperidine moiety adds a degree of flexibility and basicity to the molecule. Piperidine rings can enhance membrane permeability by increasing the molecule's ability to interact with lipid bilayers, and the presence of a sulfonyl group can further modulate this interaction.

4. **Chlorophenyl Group**: The chlorophenyl group contributes to the lipophilicity of the molecule. Chlorine atoms can enhance the molecule's ability to penetrate lipid membranes due to increased hydrophobic interactions. However, the presence of a chlorine atom can also introduce steric hindrance, which might affect the overall permeability.

5. **Acetamide Linkage**: The acetamide group provides additional hydrogen bonding potential, which can influence the molecule's solubility and interaction with the artificial membrane. This group can also contribute to the overall stability of the molecule in the membrane environment.

Overall, the given molecule exhibits a balance of lipophilic and polar characteristics, which suggests that it would have moderate permeability in the PAMPA assay. The quinoline core and chlorophenyl group enhance lipophilicity, while the sulfonamide and acetamide groups provide polar interactions, resulting in a complex balance that likely allows the molecule to traverse the artificial membrane with moderate efficiency.

Final answer: Low-to-moderate permeability.

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# 387

**SMILES:** C1COC2=C(C=C(C=C2)C3=CN=C(S3)N4CCC(CC4)C(=O)NC5=CC=CC=C5)OC1

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a piperidinecarboxamide, which is a type of compound characterized by the presence of a piperidine ring attached to a carboxamide group. This structural feature is often associated with biological activity and can influence the molecule's pharmacokinetic properties, such as permeability.

In the context of the Parallel Artificial Membrane Permeability Assay (PAMPA), the permeability of the given molecule is determined by its ability to pass through a synthetic membrane that mimics biological membranes. The membrane used in PAMPA is designed to assess the compound's lipophilicity and its ability to traverse lipid bilayers.

The given molecule contains several key structural elements that contribute to its permeability:

1. **Piperidine Ring**: The piperidine ring is a six-membered nitrogen-containing heterocycle that is relatively flexible and can enhance the molecule's solubility and permeability. Its presence in the structure suggests that the molecule may have moderate to high permeability due to its ability to interact with the lipid components of the membrane.

2. **Carboxamide Group**: The carboxamide group is a polar functional group that can form hydrogen bonds with the membrane, potentially increasing the molecule's permeability. However, its polar nature may also limit permeability if it leads to strong interactions with the membrane, hindering passage.

3. **Thiazole Ring**: The thiazole ring is a five-membered heterocycle containing both sulfur and nitrogen. This ring can contribute to the molecule's overall lipophilicity, which is a key factor in permeability. The presence of the thiazole ring may enhance the molecule's ability to penetrate the membrane due to its aromatic and heterocyclic nature.

4. **Dihydrobenzodioxepin Moiety**: This moiety is a bicyclic structure that includes an ether linkage, which can increase the molecule's lipophilicity. The dihydrobenzodioxepin group may enhance the molecule's ability to interact with the lipid components of the membrane, potentially increasing permeability.

Overall, the given molecule's combination of a piperidine ring, thiazole ring, carboxamide group, and dihydrobenzodioxepin moiety suggests that it may have moderate to high permeability in the PAMPA assay. The balance of lipophilic and polar functional groups indicates that the molecule can effectively interact with the artificial membrane, facilitating its passage.

Final answer: High permeability

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# 388

**SMILES:** CCCC1=NC2=C(C=CC(=C2)C(=O)NC3CCCC3)SC4=C1C=C(C=C4)C

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a dibenzothiazepine, which is a class of compounds known for their tricyclic structure consisting of two benzene rings fused to a thiazepine ring. This structural feature is significant in determining the molecule's permeability.

The presence of the dibenzothiazepine core suggests that the given molecule has a relatively planar and rigid structure, which can facilitate its passage through the artificial membrane by allowing it to fit into the membrane's lipid bilayer. The aromatic rings in the dibenzothiazepine core can engage in π-π interactions with the membrane, enhancing its permeability.

Additionally, the molecule contains a carboxamide group, which can form hydrogen bonds with the membrane, potentially increasing its solubility and permeability. The propyl and cyclopentyl groups attached to the nitrogen atom in the carboxamide may also influence the molecule's lipophilicity, which is crucial for permeability. These alkyl groups can increase the hydrophobic character of the molecule, which may enhance its ability to traverse the lipid-rich environment of the artificial membrane.

Overall, the combination of the dibenzothiazepine core, aromatic rings, and functional groups in the given molecule suggests that it would exhibit high permeability in the Parallel Artificial Membrane Permeability Assay.

Final answer: High permeability

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# 389

**SMILES:** CC1=NN2CCCN(C2=C1C3=CC=CC=C3OCC4=CC=CC=C4)C(=O)CC5=CC6=C(C=C5)OCO6

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound with several distinct structural features that influence its permeability in the PAMPA assay. Let's break down these features and their implications:

1. **Benzodioxole Moiety**: The presence of a benzodioxole group, which is a methylenedioxyphenyl ring, contributes to the molecule's lipophilicity. This aromatic structure can enhance the molecule's ability to interact with lipid membranes, potentially increasing its permeability.

2. **Phenyl Ring**: The phenyl ring attached to the benzodioxole moiety further increases the lipophilic character of the molecule. Aromatic rings are known to facilitate membrane permeability due to their ability to engage in π-π interactions with the lipid bilayer.

3. **Dihydropyrazolo[1,5-a]pyrimidine Core**: This bicyclic structure introduces a degree of rigidity and complexity to the molecule. The presence of nitrogen atoms in the pyrimidine ring can form hydrogen bonds, which may influence the molecule's interaction with the artificial membrane. The dihydropyrazole component can also contribute to the molecule's overall stability and permeability.

4. **Methoxy Group**: The methoxy group attached to the pyrimidine ring can enhance the molecule's solubility and may also participate in hydrogen bonding, which can affect the molecule's interaction with the membrane.

5. **Ethanone Linkage**: The ethanone linkage connects the phenyl and pyrimidine moieties, providing a flexible linker that can influence the overall conformation of the molecule. This flexibility can impact how the molecule fits into the membrane and its ability to permeate.

Overall, the given molecule's combination of aromatic rings, heterocyclic structures, and functional groups suggests that it has a high potential for permeability through the artificial membrane. The lipophilic and aromatic characteristics are likely to dominate, facilitating interactions with the lipid components of the membrane, while the heteroatoms and functional groups may contribute to specific binding interactions. Therefore, the given molecule is expected to exhibit high permeability in the PAMPA assay.

Final answer: High permeability

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# 390

**SMILES:** COC1=CC(=C(C=C1)OC)C2=NN=C3N2N=C(CS3)C4=C(C=CC=C4OC)OC

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex heterocyclic compound that features a triazolo-thiadiazine core structure. This core is known for its potential biological activity and is often used in medicinal chemistry for its pharmacological properties.

The molecule contains two 2,3-dimethoxyphenyl groups attached to the triazolo-thiadiazine core. The presence of methoxy groups on the phenyl rings can significantly influence the molecule's lipophilicity. Methoxy groups are electron-donating, which can enhance the molecule's ability to interact with lipid membranes, potentially increasing its permeability.

The triazolo-thiadiazine core itself is a fused heterocyclic system that can contribute to the molecule's overall stability and ability to traverse biological membranes. The presence of nitrogen and sulfur atoms in the heterocyclic rings can facilitate hydrogen bonding and other non-covalent interactions with the artificial membrane, which is a key factor in determining permeability.

Overall, the combination of the methoxy-substituted phenyl groups and the triazolo-thiadiazine core suggests that the given molecule would exhibit high permeability in the Parallel Artificial Membrane Permeability Assay (PAMPA). This is due to the enhanced lipophilicity and potential for favorable interactions with the membrane.

Final answer: High permeability.

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# 391

**SMILES:** CCN1C(=NN=N1)SC2=NC=NC3=C2C(=CS3)C4=CC=C(C=C4)C

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a thienopyrimidine derivative, which is characterized by a thieno[2,3-d]pyrimidine core. This core structure is a fused heterocyclic system combining a thiophene ring and a pyrimidine ring. The presence of this core often contributes to the molecule's ability to interact with biological targets, potentially enhancing its pharmacological activity.

The molecule also features a 4-methylphenyl group attached to the thienopyrimidine core. The 4-methylphenyl group is a hydrophobic moiety, which can increase the lipophilicity of the molecule. This increased lipophilicity can enhance the molecule's ability to permeate lipid membranes, suggesting a potential for high permeability.

Additionally, the molecule contains a 2-(4-tetrazolyl)ethylthio group. The tetrazole ring is a nitrogen-rich heterocycle known for its ability to mimic carboxylic acids in biological systems, often used in drug design to improve binding affinity and metabolic stability. The presence of the tetrazole group may also contribute to the molecule's overall polarity and solubility, which can influence its permeability.

The thioether linkage (ethylthio) connecting the tetrazole to the thienopyrimidine core introduces a sulfur atom, which can enhance the molecule's lipophilicity and potentially improve its ability to traverse lipid membranes.

Overall, the combination of the thienopyrimidine core, the hydrophobic 4-methylphenyl group, and the polar tetrazole group suggests that the given molecule may exhibit high permeability in the PAMPA assay, allowing it to effectively interact with the artificial membrane.

Final answer: High permeability.

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# 392

**SMILES:** CCOC(=O)C1CCN(CC1)C(=O)C(C)(C)NC(=O)NC2=CC=C(C=C2)C3=CC=CC=C3

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a derivative of piperidine, which is a six-membered ring containing one nitrogen atom. This structural feature is significant as piperidine derivatives are often known for their ability to interact with biological membranes due to their basic nitrogen, which can form hydrogen bonds and ionic interactions.

The molecule contains an ethyl ester group, which is a common feature in many bioactive compounds. This ester group can enhance the lipophilicity of the molecule, potentially increasing its ability to permeate through lipid membranes. However, ester groups can also be hydrolyzed in biological systems, which might affect the molecule's stability and permeability.

Additionally, the molecule includes a biphenyl moiety, which consists of two phenyl rings connected by a single bond. This biphenyl structure contributes to the hydrophobic character of the molecule, which can enhance its ability to permeate through lipid-rich environments, such as cell membranes. The biphenyl group can also facilitate π-π interactions with aromatic amino acids in proteins, potentially affecting the molecule's binding affinity and permeability.

The presence of an amide linkage in the molecule is another important feature. Amides are generally stable and can form hydrogen bonds, which may aid in the molecule's interaction with the artificial membrane. The amide linkage can also influence the overall conformation of the molecule, potentially affecting its permeability.

Overall, the combination of the piperidine ring, ethyl ester group, biphenyl moiety, and amide linkage suggests that the given molecule may exhibit high permeability in the artificial membrane due to its balanced hydrophilic and hydrophobic properties, as well as its ability to form various non-covalent interactions.

Final answer: High permeability.

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# 393

**SMILES:** CC1=C(N(C(=C1C(=O)C)C)C)C(=O)NC2=CC(=CC=C2)[S+](=O)(N3CCCCCC3)[O-]

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several functional groups and structural elements that influence its permeability in the PAMPA assay. Let's break down these features and their impact on permeability:

1. **Pyrrole Ring**: The presence of a pyrrole ring, which is a five-membered aromatic heterocycle containing nitrogen, contributes to the molecule's aromaticity and potential for π-π interactions. This can enhance the molecule's ability to interact with the artificial membrane, potentially increasing its permeability.

2. **Acetyl Group**: The acetyl group attached to the pyrrole ring introduces a polar carbonyl group, which can form hydrogen bonds with the membrane. This can increase the molecule's solubility in the membrane environment, potentially enhancing its permeability.

3. **Dimethyl Substituents**: The dimethyl groups on the pyrrole ring increase the hydrophobic character of the molecule. This can facilitate the passage of the molecule through the lipid-like environment of the artificial membrane, promoting permeability.

4. **Sulfonyl Group**: The sulfonyl group is highly polar and can form strong hydrogen bonds. This group can enhance the molecule's solubility in aqueous environments and may also interact with the polar components of the artificial membrane, potentially increasing permeability.

5. **Phenyl and Piperidine Groups**: The phenyl group attached to the sulfonyl moiety provides additional aromatic character, which can aid in membrane interaction through π-π stacking. The piperidine ring, a six-membered nitrogen-containing heterocycle, can increase the molecule's basicity and solubility, potentially enhancing permeability.

Overall, the given molecule exhibits a balance of hydrophobic and hydrophilic characteristics, with multiple aromatic and polar functional groups. These features suggest that the molecule can effectively interact with the artificial membrane, leading to high permeability.

Final answer: High permeability

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# 394

**SMILES:** CCOC1=CC=CC=C1N(CC(=O)NC2=C(C=CC(=C2)OC)OC)S(=O)(=O)C3=CC=CC=C3

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a sulfonamide, which is a class of compounds known for their antibacterial properties. The sulfonamide group is characterized by the presence of a sulfonyl functional group attached to an amine. In this molecule, the sulfonamide group is linked to a phenyl ring, which is further substituted with an ethoxy group. This structural feature is significant as it can influence the molecule's ability to permeate biological membranes.

The presence of the sulfonamide group suggests that the given molecule may have moderate permeability due to the polar nature of the sulfonyl group, which can form hydrogen bonds with the artificial membrane. However, the ethoxy group on the phenyl ring can increase the lipophilicity of the molecule, potentially enhancing its ability to permeate the membrane.

Additionally, the molecule contains a methoxy group attached to another phenyl ring. This group can also contribute to the lipophilicity of the molecule, potentially improving its permeability. However, the methoxy group can also introduce steric hindrance, which might limit the molecule's ability to interact with the membrane.

Overall, the balance between the polar sulfonamide group and the lipophilic phenyl and ethoxy groups suggests that the given molecule may exhibit moderate permeability in the PAMPA assay. The presence of multiple aromatic rings and ether groups can also contribute to the molecule's ability to interact with the membrane, potentially leading to a moderate permeability profile.

Final answer: Low-to-moderate permeability.

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# 395

**SMILES:** CCCC1=C(C2=C(O1)C=CC(=C2)NS(=O)(=O)C3=CC=C(C=C3)OC)C(=O)OCC

**Label:** 0

**Predi:** 0

**Correct:** 1

# Response:
The given molecule is a complex organic compound that includes several functional groups and structural features that influence its permeability in the PAMPA assay. Let's break down these features and their potential impact on permeability:

1. **Benzofuran Core**: The presence of a benzofuran moiety suggests that the molecule has a planar aromatic structure. Aromatic compounds often have good lipophilicity, which can enhance membrane permeability due to their ability to interact with lipid bilayers through π-π interactions and van der Waals forces.

2. **Carboxylate Ester Group**: The ester group in the molecule, specifically the ethyl ester, can influence the molecule's polarity and solubility. Esters are generally less polar than carboxylic acids, which can improve the lipophilicity of the molecule. This may enhance its ability to permeate the lipid-rich environment of the artificial membrane.

3. **Propyl Side Chain**: The propyl group is a non-polar alkyl chain that contributes to the overall hydrophobic character of the molecule. This can further enhance membrane permeability by increasing the molecule's lipophilicity.

4. **Methoxyphenylsulfonylamino Group**: The methoxy group is an electron-donating group that can increase the electron density of the phenyl ring, potentially affecting the molecule's interaction with the membrane. The sulfonylamino linkage introduces a polar element, which can influence the molecule's solubility and permeability balance. The presence of both hydrophobic and hydrophilic components in this group suggests a potential for moderate permeability, as it can interact with both lipid and aqueous environments.

Overall, the given molecule's structure, with its combination of aromatic, ester, and alkyl groups, suggests that it has a balanced lipophilic and hydrophilic character. This balance is likely to result in moderate permeability through the artificial membrane, allowing it to interact with both the lipid and aqueous phases of the membrane.

Final answer: Low-to-moderate permeability.

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# 396

**SMILES:** CCOC1=CC=C(C=C1)NC(=O)CC2C(=O)N(C(=O)N2CCC3=C(C=CS3)C)C4=CC=C(C=C4)F

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a member of the hydantoin class, which is known for its cyclic imide structure. This structure is characterized by a five-membered ring containing two carbonyl groups and a nitrogen atom. The presence of this imide ring is significant as it often contributes to the molecule's ability to interact with biological membranes, potentially enhancing its permeability.

The molecule also contains a 4-ethoxyphenyl group, which is a phenyl ring substituted with an ethoxy group. This aromatic group can increase the lipophilicity of the molecule, which may enhance its ability to permeate lipid membranes. The ethoxy group can also contribute to the molecule's overall hydrophobic character, further aiding in membrane permeability.

Additionally, the molecule features a 4-methylthiophen-2-yl group, which is a thiophene ring substituted with a methyl group. Thiophene rings are known for their aromaticity and can contribute to the molecule's overall stability and ability to interact with lipid bilayers.

The acetamide linkage in the molecule provides a polar functional group, which can form hydrogen bonds with the artificial membrane. This can enhance the molecule's interaction with the membrane and potentially increase its permeability.

Overall, the combination of the imide ring, aromatic groups, and polar functional groups suggests that the given molecule likely has high permeability in the Parallel Artificial Membrane Permeability Assay (PAMPA).

Final answer: High permeability

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# 397

**SMILES:** COC1=CC=CC(=C1)C2=CSC(=N2)N3CCC(CC3)C(=O)N

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a piperidinecarboxamide, which is characterized by the presence of a piperidine ring attached to a carboxamide group. This structural feature is often associated with a degree of flexibility and the ability to form hydrogen bonds, which can influence the molecule's permeability.

The molecule also contains a thiazole ring, which is a five-membered heterocyclic compound containing both sulfur and nitrogen. Thiazole rings are known for their electron-rich nature, which can enhance the molecule's ability to interact with biological membranes through π-π interactions or hydrogen bonding.

Additionally, the presence of a methoxyphenyl group introduces a methoxy substituent on a phenyl ring. The methoxy group is an electron-donating group, which can increase the lipophilicity of the molecule. This can enhance the molecule's ability to permeate through lipid membranes, as increased lipophilicity often correlates with better membrane permeability.

Overall, the combination of the piperidine ring, thiazole ring, and methoxyphenyl group suggests that the given molecule may exhibit moderate to high permeability through the artificial membrane, as these structural features can facilitate interactions with the membrane and enhance lipophilicity.

Final answer: High permeability

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# 398

**SMILES:** CC1=CC(=C(C=C1)NC(=O)C2=C(C3=C(N2C)C=CC(=C3)C)N4CCCC4=O)C

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that includes several functional groups and structural features that influence its permeability in the PAMPA assay. Let's break down these features and their impact on permeability:

1. **Indole Core**: The presence of an indole core is significant as it is a planar, aromatic structure that can facilitate interactions with the artificial membrane. Indole rings are known for their ability to participate in π-π stacking interactions, which can enhance the molecule's ability to permeate through the membrane.

2. **Dimethylpyrazole Moiety**: The pyrazole ring, substituted with two methyl groups, contributes to the molecule's lipophilicity. The increased lipophilicity can enhance the molecule's ability to traverse lipid membranes, suggesting a potential for high permeability.

3. **Carboxamide Group**: The carboxamide group is a polar functional group that can form hydrogen bonds with the artificial membrane. While this may provide some degree of interaction with the membrane, it can also introduce some degree of polarity that might hinder permeability. However, in this case, the overall structure suggests that the lipophilic components dominate.

4. **Methyl Substituents**: The methyl groups attached to both the indole and pyrazole rings increase the hydrophobic character of the molecule. This hydrophobicity is likely to enhance the molecule's ability to permeate the lipid-rich environment of the artificial membrane.

Overall, the given molecule's structure, characterized by an indole core, a dimethylpyrazole moiety, and multiple methyl groups, suggests that it has high permeability in the PAMPA assay. The balance of aromaticity, lipophilicity, and hydrogen bonding potential indicates that the molecule can effectively interact with and permeate the artificial membrane.

Final answer: High permeability

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# 399

**SMILES:** CC1=C([C@H](C(=C(N1)C)C(=O)O[C@@H]2CCCN(C2)CC3=CC=CC=C3)C4=CC(=CC=C4)[N+](=O)[O-])C(=O)OC.Cl

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a dihydrochloride salt form of nifedipine, which is a well-known calcium channel blocker used in the treatment of hypertension and angina. The permeability of the given molecule in the PAMPA assay can be inferred from its structural features.

The core structure of the given molecule is a 1,4-dihydropyridine ring, which is a characteristic feature of calcium channel blockers. This ring is known for its ability to interact with L-type calcium channels in smooth muscle cells, leading to vasodilation and a subsequent reduction in blood pressure.

The presence of the nitrophenyl group attached to the dihydropyridine ring contributes to the lipophilicity of the molecule. This lipophilic character enhances the ability of the molecule to permeate lipid membranes, which is a crucial factor in its bioavailability and activity as a drug.

Additionally, the molecule contains a piperidine moiety linked through a methylene bridge. This structural feature can influence the molecule's overall conformation and flexibility, potentially affecting its ability to traverse biological membranes.

The dihydrochloride salt form indicates that the molecule is more soluble in aqueous environments, which can facilitate its absorption and distribution in the body. However, the presence of the hydrochloride groups may also affect the permeability by increasing the overall molecular size and potentially altering the interaction with the artificial membrane.

Overall, the combination of the dihydropyridine core, lipophilic nitrophenyl group, and the piperidine moiety suggests that the given molecule would exhibit high permeability in the PAMPA assay, allowing it to effectively interact with the artificial membrane and demonstrate its pharmacological activity.

Final answer: High permeability.

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# 400

**SMILES:** CC1=CC(=CC=C1)N2C=NC3=C2C=CC(=C3)C(=O)N4CCCC(C4)C(F)(F)F

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that includes several functional groups and structural features that influence its permeability in the PAMPA assay. Let's break down these features and their impact on permeability:

1. **Benzimidazole Core**: The presence of a benzimidazole moiety is significant as it is a bicyclic structure that can enhance the molecule's ability to interact with biological membranes. Benzimidazole rings are known for their planar structure, which can facilitate passage through lipid bilayers due to their ability to intercalate between lipid molecules.

2. **Fluorophenyl Group**: The fluorophenyl group attached to the benzimidazole ring introduces a fluorine atom, which can influence the molecule's lipophilicity and electronic properties. Fluorine is highly electronegative, which can enhance the molecule's ability to penetrate lipid membranes by increasing its overall hydrophobic character. Additionally, the presence of fluorine can improve metabolic stability, which may indirectly affect permeability by prolonging the molecule's presence in the system.

3. **Methylphenyl Group**: The methylphenyl group contributes to the hydrophobic character of the molecule, which is beneficial for membrane permeability. The methyl group can also affect the molecule's steric properties, potentially influencing how it fits into the membrane or interacts with other molecules.

4. **Piperidine Ring**: The piperidine ring is a saturated nitrogen-containing heterocycle that can enhance the molecule's solubility and permeability. Piperidine rings are often found in pharmacologically active compounds and can improve the molecule's ability to cross biological membranes due to their basic nitrogen, which can participate in hydrogen bonding and ionic interactions.

5. **Trifluoromethyl Group**: The trifluoromethyl group is another highly electronegative moiety that can increase the molecule's lipophilicity. This group is known to enhance membrane permeability by increasing the molecule's ability to dissolve in lipid environments. Additionally, the trifluoromethyl group can improve the metabolic stability of the molecule, which may also contribute to its permeability.

Overall, the given molecule's structural features, including the benzimidazole core, fluorophenyl and methylphenyl groups, piperidine ring, and trifluoromethyl group, suggest that it would exhibit high permeability in the PAMPA assay. These features collectively enhance the molecule's lipophilicity, stability, and ability to interact with lipid membranes, making it likely to pass through the artificial membrane with relative ease.

Final answer: High permeability

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# 401

**SMILES:** CCN(CC)C(=O)C1=COC(=N1)COC2=CC3=C(CCN(C3C4=CC(=CC=C4)F)C(=O)C(C)C)C=C2

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several functional groups and structural motifs, each contributing to its permeability characteristics in the PAMPA assay.

1. **Isoquinoline Moiety**: The presence of the dihydroisoquinoline structure suggests a degree of rigidity and planarity, which can influence the molecule's ability to interact with the artificial membrane. Isoquinoline derivatives are known for their potential to engage in π-π stacking interactions, which can enhance permeability by facilitating passage through the membrane.

2. **Fluorophenyl Group**: The fluorophenyl group introduces a fluorine atom, which can significantly affect the molecule's lipophilicity. Fluorine is highly electronegative, and its presence can increase the molecule's overall hydrophobic character. This can enhance the permeability by improving the molecule's ability to traverse lipid-rich environments, such as biological membranes.

3. **Methylamino Linkage**: The methylamino group provides a site for hydrogen bonding, which can influence the molecule's solubility and interaction with the membrane. This group can enhance the molecule's ability to form hydrogen bonds with the membrane, potentially increasing its permeability.

4. **Oxadiazole Ring**: The oxadiazole ring is a heterocyclic structure that can contribute to the molecule's overall stability and rigidity. This ring can also participate in hydrogen bonding and dipole interactions, which may aid in membrane permeability.

5. **Carboxamide Group**: The carboxamide group is polar and can form hydrogen bonds, which may enhance solubility and interaction with the membrane. However, it can also introduce some degree of polarity, which might reduce permeability by increasing the molecule's affinity for aqueous environments.

6. **Propanoyl and Isopropyl Groups**: These alkyl groups contribute to the molecule's hydrophobic character, which can enhance permeability by promoting interactions with the lipid components of the membrane.

Overall, the given molecule's structure suggests a balance of hydrophobic and hydrophilic properties, with several functional groups that can interact with the artificial membrane. The presence of fluorine, aromatic rings, and polar groups indicates that the molecule likely exhibits high permeability in the PAMPA assay, as it can effectively interact with and pass through the membrane.

Final answer: High permeability

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# 402

**SMILES:** CCC1=CC=CC=C1N2C(=N)C3=C(NN=C3N=C2SCC(=O)NC4=CC=C(C=C4)C)C

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a complex organic compound that features several distinct structural components, each contributing to its permeability characteristics in the PAMPA assay.

1. **Pyrazolopyrimidine Core**: The central structure of the given molecule is a pyrazolopyrimidine, which is a bicyclic system combining a pyrazole and a pyrimidine ring. This core is known for its planar and aromatic nature, which can facilitate interactions with the artificial membrane, potentially enhancing permeability. The aromaticity and rigidity of this core can allow the molecule to pass through the membrane more efficiently.

2. **Imino and Sulfanyl Groups**: The presence of an imino group (a nitrogen double-bonded to a carbon) and a sulfanyl group (a sulfur atom bonded to a carbon) in the structure introduces polar characteristics. These groups can form hydrogen bonds and other polar interactions with the membrane, which may aid in permeability. However, they can also introduce steric hindrance and increase the overall polarity of the molecule, which might reduce permeability depending on the balance with other hydrophobic parts.

3. **Aromatic Substituents**: The given molecule contains two aromatic rings: a 4-ethylphenyl group and a 4-methylphenyl group. These hydrophobic aromatic rings can enhance the lipophilicity of the molecule, promoting its ability to traverse the lipid-rich environment of the artificial membrane. The ethyl and methyl substituents further increase the hydrophobic character, potentially improving permeability.

4. **Thioether Linkage**: The sulfanyl group connects the pyrazolopyrimidine core to the acetamide moiety. Thioether linkages are generally stable and can contribute to the overall lipophilicity of the molecule. This linkage may facilitate the passage of the molecule through the membrane by providing a flexible connection between the core and the peripheral groups.

5. **Acetamide Moiety**: The acetamide group introduces additional polar characteristics, which can enhance solubility in aqueous environments. However, its presence may also create a balance between hydrophilicity and lipophilicity, potentially aiding in membrane permeability by allowing the molecule to interact with both polar and non-polar regions of the membrane.

Overall, the given molecule's structure suggests a balance between hydrophilic and lipophilic properties, with the aromatic and heterocyclic cores contributing to lipophilicity and the polar functional groups providing potential for hydrogen bonding and solubility. This balance likely results in moderate permeability, allowing the molecule to interact with the artificial membrane effectively while maintaining some solubility in aqueous environments.

Final answer: Low-to-moderate permeability.

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# 403

**SMILES:** C1CN(CC2=CN=C(C=C2N1)NC3=CC=CC=C3)CC4=CC(=CC=C4)F

**Label:** 0

**Predi:** 1

**Correct:** 0

# Response:
The given molecule is a pyridopyridine derivative, which is a bicyclic compound consisting of two pyridine rings fused together. This structure is known for its planar and aromatic characteristics, which can influence its permeability properties.

The presence of the pyridopyridine core suggests that the given molecule may have moderate to high permeability due to its aromatic nature. Aromatic compounds often have good lipophilicity, which can enhance their ability to permeate lipid membranes. This is because aromatic rings can participate in π-π interactions with the lipid bilayer, facilitating passage through the membrane.

Additionally, the molecule contains a phenyl group attached to a nitrogen atom, which is part of the pyridopyridine structure. This phenyl group can further contribute to the lipophilicity of the molecule, potentially increasing its permeability.

The fluorophenyl moiety introduces a fluorine atom, which can influence the molecule's electronic properties. Fluorine is highly electronegative, and its presence can enhance the molecule's ability to interact with the lipid membrane by increasing its overall lipophilicity. This can also affect the molecule's metabolic stability and permeability.

The piperazine ring in the structure is a common motif in many pharmaceuticals, known for its ability to enhance solubility and permeability. Piperazine can increase the flexibility of the molecule, allowing it to adopt conformations that may facilitate membrane permeation.

Overall, the combination of the pyridopyridine core, phenyl group, fluorophenyl moiety, and piperazine ring suggests that the given molecule likely has high permeability in the PAMPA assay. These structural features collectively contribute to its ability to interact favorably with the artificial membrane, enhancing its permeability.

Final answer: High permeability.

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# 404

**SMILES:** C1=COC(=C1)CNC(=O)COC(=O)CCC(=O)C2=CC=CS2

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a complex ester that features several functional groups contributing to its permeability characteristics. Let's break down the structural components and their influence on permeability:

1. **Furan Rings**: The molecule contains two furan rings, which are five-membered aromatic heterocycles with oxygen. Furan rings are relatively polar due to the presence of the oxygen atom, which can engage in hydrogen bonding and dipole-dipole interactions. This polarity can enhance the molecule's solubility in polar environments, such as aqueous media, which is beneficial for permeability through biological membranes.

2. **Ester Linkage**: The ester functional group in the molecule is formed between the furan-containing moiety and the rest of the structure. Esters are generally polar and can participate in hydrogen bonding, which may facilitate interaction with the artificial membrane. However, esters can also be susceptible to hydrolysis, which might affect the stability of the molecule in biological systems.

3. **Thiophene Ring**: The thiophene ring, another five-membered aromatic heterocycle, contains sulfur. Thiophene is less polar than furan due to the presence of sulfur, which is less electronegative than oxygen. This can reduce the overall polarity of the molecule, potentially decreasing its solubility in water and affecting its permeability.

4. **Ketone Group**: The presence of a ketone group (oxo) in the molecule introduces additional polarity. Ketones can engage in dipole-dipole interactions, which may enhance the molecule's interaction with the membrane. However, the ketone group can also be a site for metabolic transformation, which might impact the molecule's permeability and stability.

5. **Amino Group**: The amino group attached to the furan ring can increase the molecule's basicity and polarity. Amino groups are known for their ability to form hydrogen bonds, which can enhance solubility and permeability. However, the presence of the amino group may also introduce steric hindrance, affecting the molecule's ability to pass through the membrane.

Overall, the given molecule's permeability is influenced by the balance of its polar and non-polar components. The presence of multiple furan rings and the ketone group likely contribute to moderate polarity, enhancing solubility and permeability. However, the thiophene ring and ester linkage may reduce overall polarity and increase susceptibility to enzymatic degradation, respectively. These factors suggest that the given molecule would exhibit moderate permeability in the PAMPA assay.

Final answer: Low-to-moderate permeability.

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# 405

**SMILES:** CC1=CC=CC2=NC(=C(N12)NC3=CC=C(C=C3)C(C)C)C4=CN=CC=C4

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a complex organic compound that features several functional groups and aromatic rings, which influence its permeability in the PAMPA assay. 

The molecule contains an imidazo[1,2-a]pyridine core, which is a bicyclic structure combining an imidazole ring and a pyridine ring. This core is known for its planar aromatic nature, which can facilitate interactions with the artificial membrane, potentially enhancing permeability. The presence of this core structure often contributes to the molecule's ability to traverse biological membranes due to its aromatic and heterocyclic characteristics.

Additionally, the molecule has a pyridin-3-yl group, which is another aromatic ring. Aromatic rings are generally lipophilic, which can enhance the molecule's ability to interact with the lipid components of the artificial membrane, promoting permeability.

The molecule also features a 4-methyl group attached to the imidazo[1,2-a]pyridine core. Methyl groups can increase lipophilicity, which may further enhance the molecule's permeability by increasing its solubility in lipid environments.

Moreover, the molecule has an N-(4-propan-2-ylphenyl) group, which includes an isopropyl group attached to a phenyl ring. The isopropyl group is a bulky, hydrophobic moiety that can increase the molecule's overall lipophilicity, potentially improving its ability to permeate the artificial membrane.

Overall, the combination of aromatic rings, heterocyclic structures, and hydrophobic substituents in the given molecule suggests that it would exhibit high permeability in the PAMPA assay. These structural features facilitate interactions with the artificial membrane, enhancing the molecule's ability to permeate through it.

Final answer: High permeability.

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# 406

**SMILES:** CN1CCC2=CC3=C(C=C2C1)OCO3

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a member of the isoquinoline family, which is known for its aromatic heterocyclic structure. The molecule features a dioxolo ring fused to the isoquinoline core, which is a common structural motif in many bioactive compounds. This structural feature can influence the molecule's ability to interact with biological membranes.

The presence of the dioxolo ring introduces an oxygen-containing heterocycle, which can enhance the molecule's polarity and potentially increase its ability to form hydrogen bonds with the artificial membrane. This can facilitate the molecule's passage through the membrane by increasing its solubility in the membrane's lipid bilayer.

Additionally, the methyl group attached to the isoquinoline core can impact the molecule's lipophilicity, which is a key factor in determining permeability. Methyl groups can increase the hydrophobic character of the molecule, potentially enhancing its ability to traverse lipid-rich environments like biological membranes.

Overall, the combination of the aromatic isoquinoline core, the dioxolo ring, and the methyl group suggests that the given molecule may exhibit moderate permeability in the PAMPA assay, as it possesses both polar and non-polar characteristics that can facilitate interaction with the artificial membrane.

Final answer: Low-to-moderate permeability.

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