# 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 pyrimidines and contains a 2-chlorophenyl group and a pyrazolyl group attached to the pyrimidine ring. The presence of these functional groups can influence the molecule's permeability.

The pyrimidine core is a heterocyclic aromatic compound, which generally contributes to the molecule's ability to interact with biological membranes. The aromatic nature of the pyrimidine ring can facilitate interactions with the lipid bilayer of cell membranes, potentially enhancing permeability.

The 2-chlorophenyl group introduces a chlorine atom, 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.

The pyrazolyl group is another heterocyclic aromatic ring, which can also interact with the membrane through π-π stacking or hydrophobic interactions. This can further support the molecule's permeability.

Overall, the combination of these aromatic and lipophilic groups suggests that the given molecule likely exhibits high permeability in the PAMPA assay.

Final answer: High permeability

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# 1

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

**Label:** 1

**Predi:** 0

**Correct:** 0

# 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 amino group at the second position and a methyl group at the first position on the quinazoline core influences its chemical properties and permeability.

In the context of the Parallel Artificial Membrane Permeability Assay (PAMPA), the artificial membrane mimics biological membranes, such as the lipid bilayer of cell membranes. The permeability of the given molecule is determined by its ability to cross this artificial membrane, which is influenced by several factors:

1. **Lipophilicity**: The quinazoline core is relatively hydrophobic, which suggests that the given molecule may have moderate to high lipophilicity. This property can enhance its ability to permeate lipid membranes.

2. **Polar Functional Groups**: The amino group introduces a polar character to the molecule, which can form hydrogen bonds with the membrane or the surrounding environment. This can affect the molecule's solubility and permeability, potentially increasing its ability to interact with the membrane.

3. **Molecular Size and Shape**: The overall size and shape of the molecule, including the methyl group, can influence its ability to fit into the membrane's structure. The methyl group may increase steric hindrance, potentially affecting permeability.

Considering these factors, the given molecule is likely to exhibit moderate permeability in the PAMPA assay. The balance between its hydrophobic core and polar functional groups suggests that it can interact with the artificial membrane, but the specific arrangement and size of the functional groups may limit its permeability compared to more lipophilic or smaller molecules.

Final answer: Low-to-moderate 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, specifically a modified adenosine. It consists of a purine base, which is adenine, attached to a sugar moiety, which is a ribose derivative. The presence of the purine base, adenine, suggests that the molecule is likely to interact with biological systems in a manner similar to other nucleosides, potentially participating in nucleic acid synthesis or metabolism.

The molecule has an amino group on the purine ring, which can enhance its solubility and potentially its ability to form hydrogen bonds with biological targets. The ribose-like sugar moiety is modified with an additional hydroxymethyl group, which can influence the molecule's overall polarity and solubility.

In the context of the Parallel Artificial Membrane Permeability Assay (PAMPA), the molecule's permeability is influenced by its ability to cross the artificial membrane, which mimics biological membranes. The presence of polar functional groups, such as amino and hydroxyl groups, suggests that the molecule may have moderate permeability due to their ability to form hydrogen bonds with the membrane. However, the overall size and hydrophilicity of the molecule, due to the sugar moiety and additional hydroxymethyl group, may limit its permeability compared to smaller, more lipophilic molecules.

Therefore, the given molecule is likely to have low-to-moderate permeability in the PAMPA assay, as its polar functional groups and sugar moiety may hinder its passage through the artificial membrane.

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 polycyclic compound with multiple rings and heteroatoms, including oxygen and nitrogen. The presence of these heteroatoms suggests potential hydrogen bonding capabilities, which can influence its interaction with the artificial membrane.

The molecule's structure includes methoxy groups, which are ether functional groups. These groups can increase lipophilicity, potentially enhancing the molecule's ability to permeate through the lipid-like environment of the artificial membrane.

Additionally, the polycyclic nature of the molecule indicates a rigid structure, which can affect its ability to fit into the membrane pores. The rigidity might either hinder or facilitate permeability depending on the size and shape of the membrane pores.

Overall, the combination of methoxy groups and the polycyclic framework suggests that the given molecule may exhibit moderate permeability in the artificial membrane, balancing between hydrophilic and lipophilic interactions.

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 derivative of hydroxyphenylindole, which is a class of compounds known for their biological activity. In this molecule, the presence of bromine atoms and a hydroxy group on the phenyl ring suggests that it has been modified to potentially enhance its interaction with biological membranes.

The artificial membrane used in the PAMPA assay is designed to mimic the lipid bilayer of cell membranes. The permeability of the given molecule is influenced by its structural features, such as the presence of halogen atoms (bromine) and the hydroxy group. These functional groups can increase the molecule's lipophilicity, which may enhance its ability to traverse the lipid membrane.

Additionally, the indole moiety is a planar, aromatic structure that can facilitate interactions with the membrane through π-π stacking or hydrophobic interactions. The methylene bridge connecting the phenyl and indole rings may also contribute to the molecule's flexibility, allowing it to adapt its conformation to better fit into the membrane.

Overall, the combination of these structural features suggests that the given molecule likely exhibits high permeability in the PAMPA assay, as it is designed to mimic the permeability of small molecules in biological systems.

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 biological activity, including antiparasitic and antifungal properties. The benzimidazole core is a bicyclic structure consisting of a benzene ring fused to an imidazole ring, which contributes to the molecule's ability to interact with biological targets.

The presence of the benzoyl group attached to the benzimidazole core increases the molecule's lipophilicity, enhancing its ability to permeate lipid membranes. This is because the benzoyl group is a hydrophobic moiety that can interact with the lipid bilayer of the artificial membrane, facilitating passage through it.

Additionally, the carbamate group in the molecule can also influence permeability. Carbamates are known to be relatively stable and can participate in hydrogen bonding, which may affect the molecule's interaction with the artificial membrane. However, the carbamate group is less hydrophobic compared to the benzoyl group, which might limit its contribution to permeability.

Overall, the combination of the benzimidazole core, the benzoyl group, and the carbamate group suggests that the given molecule would exhibit high permeability in the Parallel Artificial Membrane Permeability Assay (PAMPA), as these structural features enhance its ability to traverse 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:** 0

**Correct:** 0

# Response:
The given molecule is a complex polycyclic compound with a tetracyclic structure, which includes multiple fused rings. The presence of a nitrogen atom in the structure indicates that it is an azapolycyclic compound, which is a subclass of polycyclic compounds containing nitrogen. 

The structural complexity and the presence of multiple rings suggest that the molecule has a rigid and compact three-dimensional shape. This rigidity can influence its interaction with the artificial membrane, potentially allowing it to fit well into the membrane's structure. The nitrogen atom may also play a role in hydrogen bonding or ionic interactions with the membrane, which can further affect its permeability.

Given these structural features, the molecule is likely to have moderate permeability through the artificial membrane. The balance of rigidity and potential for specific interactions with the membrane suggests that it can traverse the membrane, but not necessarily with high speed or ease. Therefore, the permeability of the given molecule to the artificial membrane is likely to be low-to-moderate.

Final answer: Low-to-moderate 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:** 0

**Correct:** 1

# Response:
The given molecule is a derivative of folate, specifically a methylated form of folate. Its structure includes a pteridine ring, which is a key feature of folate compounds. This ring is substituted with an amino group and a methylamino group, which can influence the molecule's interaction with biological membranes.

The molecule also contains a benzoyl group linked to an amino group, which is connected to a pentanedioic acid moiety. The presence of the benzoyl group can enhance the molecule's lipophilicity, potentially increasing its ability to permeate lipid membranes.

In the context of the Parallel Artificial Membrane Permeability Assay (PAMPA), the artificial membrane mimics biological membranes. The given molecule's structure suggests that it may have moderate lipophilicity due to the benzoyl group, which could facilitate its passage through the membrane. However, the presence of polar groups, such as the amino and carboxylic acid groups, may also contribute to hydrogen bonding, which can affect its permeability.

Overall, the balance of lipophilic and hydrophilic properties in the given molecule suggests that it may have moderate permeability in the PAMPA assay, but the exact permeability would depend on the specific conditions of the assay.

Final answer: Low-to-moderate permeability.

------
# 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 also contribute to hydrogen bonding, which may enhance solubility and permeability.

2. **Trifluoromethyl Group**: The trifluoromethyl group is highly electronegative and lipophilic. This group can increase the molecule's lipophilicity, potentially enhancing its ability to permeate lipid membranes. However, it can also affect the molecule's overall polarity, which may have a dual effect on permeability.

3. **Phthalazine Carboxamide Moiety**: The phthalazine ring is a bicyclic aromatic system that can contribute to the rigidity and planarity of the molecule. The carboxamide group is polar and can form hydrogen bonds, which may aid in solubility and permeability. 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 can introduce additional polarity, which may enhance hydrogen bonding and solubility. This can also affect the electronic distribution within the molecule, potentially influencing its interaction with the artificial membrane.

Overall, the given molecule exhibits a combination 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 the lipid and aqueous phases of the membrane. 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.

------
# 9

**SMILES:** CCCCCN1C(=O)C2=C(C=C(C=C2)C(=O)NCCCN3CCCCC3)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 structure of the given molecule includes several key features that influence its permeability:

1. **Quinazoline Core**: The quinazoline core is a bicyclic structure that consists of a benzene ring fused to a pyrimidine ring. This core is relatively planar and aromatic, which can facilitate interactions with biological membranes through π-π stacking and hydrophobic interactions. The presence of this core often contributes to the molecule's ability to permeate lipid membranes.

2. **Piperidine Moiety**: The piperidine group is a six-membered nitrogen-containing heterocycle. This moiety is known for enhancing the solubility and permeability of molecules due to its basic nature, which can form hydrogen bonds and ionic interactions with the membrane. The piperidine group is attached via a propyl linker, which provides flexibility and may help the molecule to adapt its conformation to fit into the membrane.

3. **Butyl Chain**: The butyl chain is a hydrophobic alkyl group that can increase the lipophilicity of the molecule. This hydrophobic character can enhance the molecule's ability to interact with the lipid bilayer of the membrane, promoting permeability.

4. **Carboxamide Group**: The carboxamide group is polar and can form hydrogen bonds with the membrane or surrounding aqueous environment. This group can also contribute to the molecule's solubility and may play a role in its interaction with the membrane.

5. **Dioxo Groups**: The presence of two oxo groups (carbonyl groups) in the quinazoline ring can increase the molecule's polarity and ability to form hydrogen bonds. These groups can interact with polar sites on the membrane or in the surrounding environment, potentially affecting permeability.

Overall, the given molecule's combination of aromatic, hydrophobic, and polar features suggests that it may have moderate to high permeability in the PAMPA assay. The balance of hydrophobic and hydrophilic groups allows it to interact effectively with the artificial membrane, facilitating its passage through the membrane.

Final answer: High 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 permeate through lipid membranes. The presence of these rings suggests that the molecule may have a favorable interaction with the hydrophobic environment of the artificial membrane.

2. **Thiadiazole Ring**: The 1,3,4-thiadiazole moiety is a heterocyclic compound that can contribute to the molecule's overall stability and electronic properties. The sulfur and nitrogen atoms in the thiadiazole ring can participate in hydrogen bonding and other polar interactions, which may influence the molecule's permeability by balancing hydrophilic and hydrophobic interactions.

3. **Carboxamide Group**: The carboxamide group is a polar functional group that can form hydrogen bonds with the artificial membrane. This group can enhance the molecule's solubility in aqueous environments, potentially aiding in its permeability. However, the balance between hydrophilic and lipophilic properties will determine its overall permeability.

4. **Chlorine Substitution**: The chlorophenoxy group introduces a chlorine atom, which can increase the molecule's lipophilicity. Chlorine is a halogen that can enhance the membrane permeability by increasing the molecule's ability to interact with lipid bilayers.

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 aromatic rings and chlorine substitution likely contribute to its lipophilicity, while the carboxamide group provides a degree of hydrophilicity. This balance suggests that the molecule may exhibit moderate permeability, allowing it to traverse the artificial membrane effectively.

Final answer: Low-to-moderate permeability.

------
# 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 includes several functional groups and structural features that influence its permeability in the PAMPA assay. Let's break down these features:

1. **Benzodioxole Moiety**: The presence of the benzodioxole group, which is a methylenedioxyphenyl structure, contributes to the molecule's lipophilicity. This group can enhance the molecule's ability to interact with lipid membranes, potentially increasing its permeability.

2. **Triazolothiadiazole Core**: The triazolothiadiazole core is a fused heterocyclic system that can influence the molecule's electronic properties and rigidity. The presence of nitrogen and sulfur atoms in this core can form hydrogen bonds or dipole interactions with the artificial membrane, which may affect permeability.

3. **Phenyl Ring**: The phenyl group attached to the triazolothiadiazole core adds to the hydrophobic character of the molecule. This can enhance the molecule's ability to traverse lipid-rich environments, such as biological membranes.

Overall, the combination of these structural features suggests that the given molecule is likely to exhibit high permeability in the PAMPA assay. The lipophilic benzodioxole and phenyl groups, along with the potential for hydrogen bonding and dipole interactions from the triazolothiadiazole core, contribute to its ability to pass through 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 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, often enhancing permeability due to their planar aromatic structure. This can facilitate the passage of the molecule through the artificial membrane by allowing it to intercalate or stack between lipid molecules.

Additionally, the molecule includes a 1,2,4-oxadiazole ring, which is a five-membered heterocyclic ring containing two nitrogen atoms and one oxygen atom. This ring is relatively polar and can engage in hydrogen bonding and dipole-dipole interactions with the membrane, potentially increasing the molecule's affinity for the artificial membrane.

The presence of a methoxy group attached to the quinoline ring introduces an electron-donating effect, which can influence the electronic distribution across the molecule. This modification can enhance the lipophilicity of the molecule, thereby improving its ability to traverse the lipid-rich environment of the artificial 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 quinoline core, polar oxadiazole ring, and methoxy substituent collectively contribute to the molecule's ability to interact favorably with the artificial membrane, facilitating its passage.

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 to understand its 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.

2. **Dimethyl Substitution**: The dimethyl groups on the oxazole ring increase the hydrophobic character of the molecule. This can affect the balance between hydrophilicity and lipophilicity, potentially enhancing membrane permeability by increasing the molecule's ability to interact with the lipid components of the membrane.

3. **Phenyl Group**: The phenyl group attached to the oxazole ring adds to the hydrophobic nature of the molecule. Aromatic rings can participate in π-π interactions with the membrane, which may facilitate permeation.

4. **Morpholine Ring**: The morpholine ring is a six-membered heterocycle containing both nitrogen and oxygen. This ring can enhance the molecule's solubility and ability to form hydrogen bonds, which may improve permeability. Additionally, the morpholine ring can interact with the polar head groups of the artificial membrane, potentially aiding in permeation.

5. **Piperidine Ring**: The piperidine ring is a six-membered nitrogen-containing heterocycle. This structure is relatively flexible and can enhance the molecule's ability to fit into the membrane's structure. The presence of the piperidine ring can also contribute to the basicity of the molecule, which may affect its interaction with the membrane.

6. **Carboxamide Group**: The carboxamide group is polar and can form hydrogen bonds, which may enhance the molecule's solubility and interaction with the membrane. This group can also participate in dipole-dipole interactions, which may facilitate permeation.

Overall, the given molecule has a combination of hydrophobic and hydrophilic features, which suggests that it may have moderate permeability in the PAMPA assay. The balance of these features allows the molecule to interact with both the aqueous and lipid components of the membrane, potentially facilitating its passage through the artificial membrane.

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 suggests that the given molecule has a planar structure, which can facilitate interactions with the artificial membrane. The aromatic nature of the rings can also contribute to π-π stacking interactions, which may enhance the molecule's ability to permeate through the membrane.

The amide linkage in the given 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 potentially enhance its permeability.

Overall, the combination of aromatic rings and the amide linkage suggests that the given molecule may exhibit moderate to high permeability in the PAMPA assay, as the structural features favor interactions with the artificial membrane.

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 interaction with biological membranes.

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. The thiophen-2-yl group is a five-membered heterocyclic ring containing sulfur, which can contribute to the molecule's electronic properties and potentially enhance its ability to interact with the membrane.

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 influenced by its ability to traverse this membrane, which is determined by its lipophilicity, hydrogen bonding capacity, and overall molecular size.

Given the presence of the hydrophobic 2-methylphenyl group and the polar urea group, the molecule likely exhibits a balance of hydrophobic and hydrophilic properties. The thiophen-2-yl group may also contribute to the molecule's ability to interact with the membrane through π-π interactions or other non-covalent interactions.

Overall, the given molecule is expected to have moderate permeability in the PAMPA assay, as it possesses both hydrophobic and hydrophilic characteristics that allow it to interact with the artificial membrane, but may not be highly permeable due to the presence of the polar urea group and the potential for hydrogen bonding.

Final answer: Low-to-moderate permeability.

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# 16

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

**Label:** 0

**Predi:** 0

**Correct:** 1

# Response:
The given molecule is a derivative of purine, which is a heterocyclic aromatic organic compound. The structure of the given molecule includes a purine core, which is a fused bicyclic structure consisting of a pyrimidine ring fused to an imidazole ring. This core is modified by the presence of a carbonyl group at a specific position, forming a 7H-purin-6-one.

The presence of the carbonyl group (the oxo group) in the purine structure can influence the molecule's polarity and hydrogen bonding capabilities. The carbonyl group introduces a polar site that can participate in hydrogen bonding, potentially affecting the molecule's interaction with the artificial membrane.

In the context of the Parallel Artificial Membrane Permeability Assay (PAMPA), the artificial membrane mimics biological membranes, and the permeability of a molecule is influenced by its ability to interact with and pass through the membrane. The given molecule's purine core provides a planar, aromatic structure that can facilitate stacking interactions with the membrane, while the carbonyl group may enhance its solubility and interaction with the membrane's polar head groups.

Overall, the given molecule is likely to exhibit moderate permeability due to the balance between its aromatic, planar structure and the polar carbonyl group, which can interact with the membrane.

Final answer: Low-to-moderate 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 includes several functional groups and structural features that influence its permeability in the PAMPA assay. Let's break down these features to understand its 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 generally contribute to the lipophilicity of a molecule, which can enhance its ability to permeate through lipid membranes. However, the presence of these rings also means the molecule may have significant interactions with the artificial membrane, potentially affecting its permeability.

2. **Amino Group**: The presence of an amino group attached to the pyrazolo[3,4-d]pyrimidine ring introduces a site for hydrogen bonding. This can increase the molecule's solubility in water and may also facilitate interactions with the artificial membrane, which is designed to mimic biological membranes. The amino group can form hydrogen bonds with the membrane, potentially enhancing permeability.

3. **Carboxylic Acid Group**: The benzoic acid moiety contributes a carboxylic acid group, which is polar and can form hydrogen bonds. This group can also ionize under physiological conditions, which may affect the molecule's overall charge and solubility. The ionization can influence the molecule's interaction with the membrane, potentially increasing its permeability due to the formation of ionic interactions.

4. **Methyl Substituents**: The methyl groups on the pyrazolo[3,4-d]pyrimidine 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, 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 permeability in PAMPA assays. The aromatic rings and methyl groups contribute to lipophilicity, while the amino and carboxylic acid groups provide sites for hydrogen bonding and ionic interactions. These features suggest that the molecule would 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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# 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 to understand its permeability characteristics.

1. **Piperidine Ring**: The presence of a piperidine ring, which is a six-membered nitrogen-containing heterocycle, is a common feature in many bioactive compounds. Piperidine rings are known to enhance the lipophilicity of molecules, which can improve their ability to permeate lipid membranes. This suggests that the given molecule may have moderate to high permeability due to the piperidine ring.

2. **Carboxamide Group**: The carboxamide group attached to the piperidine ring can form hydrogen bonds, which may enhance the molecule's solubility in aqueous environments. However, this group can also interact with the artificial membrane, potentially facilitating permeation.

3. **Diethylaminoethyl Side Chain**: The diethylamino group is a basic moiety that can be protonated under physiological conditions, increasing the molecule's overall solubility in water. This can enhance the molecule's ability to interact with the polar head groups of the artificial membrane, potentially improving permeability.

4. **Fluorophenyl Group**: The presence of a fluorophenyl group introduces a hydrophobic aromatic ring, which can enhance lipophilicity. The fluorine atom can also influence the electronic properties of the phenyl ring, potentially affecting the molecule's interaction with the membrane.

5. **Thiazolo[3,2-a]imidazole Moiety**: This bicyclic structure is a heteroaromatic system that can contribute to the molecule's overall rigidity and planarity. The presence of nitrogen and sulfur atoms in this moiety can also participate in hydrogen bonding and other non-covalent interactions with the membrane.

Overall, the given molecule's combination of lipophilic and hydrophilic features, along with its ability to form hydrogen bonds and interact with the artificial membrane, suggests that it may have high permeability in the PAMPA assay. The balance of these structural elements allows the molecule to effectively traverse the artificial membrane, making it a candidate for further drug development studies.

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 indole derivative 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. **Indole Core**: The indole structure is a bicyclic compound consisting of a benzene ring fused to a pyrrole ring. This core is relatively planar and hydrophobic, which can facilitate membrane permeability due to its ability to interact with lipid bilayers through hydrophobic interactions.

2. **Methoxyphenyl Group**: The presence of a methoxy group on the phenyl ring increases the molecule's lipophilicity. Methoxy groups can enhance membrane permeability by increasing the compound's ability to dissolve in lipid membranes, which is beneficial for passive diffusion.

3. **Furan-2-ylmethyl Group**: The furan ring is a five-membered aromatic heterocycle that contributes to the molecule's overall aromaticity and lipophilicity. The presence of this group can enhance membrane permeability by increasing the molecule's ability to interact with lipid membranes.

4. **Methylamino Group**: The methylamino group introduces a basic nitrogen atom, which can form hydrogen bonds with the polar head groups of the artificial membrane. This can enhance the molecule's interaction with the membrane and potentially increase its permeability.

5. **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 facilitate or hinder permeability depending on the pH and the specific environment of the assay. In general, carboxylic acids can increase water solubility, which might reduce permeability through the membrane.

Overall, the given molecule has a balance of hydrophobic and hydrophilic groups. The indole core and methoxyphenyl group contribute to lipophilicity, enhancing membrane permeability, while the carboxylic acid group may reduce permeability due to its hydrophilic nature. The methylamino group can form hydrogen bonds, potentially aiding in membrane interaction. Considering these factors, the given molecule is likely to exhibit high permeability in the PAMPA assay.

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:** 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. Let's break down the structural features and their impact on permeability:

1. **Aromatic Rings**: The molecule contains multiple aromatic rings, including phenyl and piperazine rings. Aromatic rings generally contribute to lipophilicity, which can enhance membrane permeability due to their ability to interact with the lipid bilayer of the artificial membrane.

2. **Amide Linkage**: The presence of an amide group, formed by the carbonyl group attached to the nitrogen of the piperazine ring, can influence the molecule's polarity and hydrogen bonding capabilities. Amide linkages can form hydrogen bonds with the membrane, potentially affecting permeability.

3. **Fluorobenzoyl Group**: The fluorine atom in the fluorobenzoyl group is electronegative, which can influence the electronic distribution within the molecule. This can affect the molecule's ability to interact with the membrane, potentially enhancing permeability due to increased lipophilicity.

4. **Acetylphenyl Group**: The acetyl group attached to the phenyl ring introduces additional polarity and potential for hydrogen bonding. This can affect the balance between hydrophilicity and lipophilicity, which is crucial for membrane permeability.

5. **Carboxylic Acid Group**: The carboxylic acid group is a highly polar and hydrophilic functional group. It can form strong hydrogen bonds and ionic interactions with the membrane, which may hinder permeability due to its tendency to interact with the aqueous environment rather than the lipid bilayer.

Overall, the given molecule has a mix of lipophilic and hydrophilic characteristics due to its aromatic rings and functional groups. The balance between these properties will determine its permeability in the PAMPA assay. The presence of multiple aromatic rings and the fluorobenzoyl group likely contribute to high permeability, while the carboxylic acid group may reduce it due to its hydrophilic nature. Therefore, the given molecule is likely to have high permeability in the PAMPA assay.

Final answer: High 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 potential impact on permeability:

1. **Aromatic Rings**: The molecule contains multiple aromatic rings, including a bromobenzoyl group and a piperazine-linked phenyl ring. 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.

2. **Amide Linkage**: The molecule features an amide bond connecting the bromobenzoyl group to the piperazine ring. Amide linkages are relatively polar and can form hydrogen bonds, which may enhance solubility and permeability. However, the overall effect depends on the balance between the polar and nonpolar regions of the molecule.

3. **Piperazine Ring**: The piperazine moiety is a common feature in many pharmaceuticals and can enhance solubility due to its basic nitrogen atoms. This can improve permeability by increasing the molecule's ability to interact with the lipid bilayer of the artificial membrane.

4. **Carboxylic Acid Group**: The presence of a carboxylic acid group is significant for permeability. Carboxylic acids are polar and can form hydrogen bonds, which may enhance solubility in aqueous environments. However, they can also be ionized at physiological pH, which might reduce permeability through the lipid membrane.

Overall, the given molecule has a balance of lipophilic aromatic rings and polar functional groups. The presence of the piperazine ring and amide linkage suggests moderate permeability, while the carboxylic acid group may reduce permeability due to its polar nature. The bromine atom could also introduce some steric hindrance. Therefore, the given molecule is likely to exhibit low-to-moderate permeability in the PAMPA assay.

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 quinazoline derivative, which is a class of compounds known for their 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 ability to interact with various biological targets, often contributing to the molecule's pharmacological properties.

The presence of a triazole ring fused to the quinazoline core can enhance the molecule's stability and binding affinity to biological targets, potentially increasing its permeability through biological membranes. Triazoles are known for their ability to form hydrogen bonds and engage in π-π interactions, which can facilitate the passage of the molecule through lipid bilayers.

Additionally, the molecule contains a sulfonamide group attached to a phenyl ring. Sulfonamides are known for their ability to enhance the solubility and permeability of compounds due to their polar nature. This group can also participate in hydrogen bonding, which may further aid in the molecule's permeability.

The methyl groups present in the structure can increase the lipophilicity of the molecule, which may enhance its ability to permeate lipid membranes. However, the balance between hydrophilic and lipophilic properties is crucial in determining the overall permeability of the molecule.

In summary, the given molecule's quinazoline core, triazole ring, sulfonamide group, and methyl substituents collectively contribute to its potential high permeability in the Parallel Artificial Membrane Permeability Assay (PAMPA). These structural features suggest that the molecule can effectively interact with the artificial membrane, indicating a high permeability.

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:** 1

**Correct:** 0

# Response:
The given molecule is characterized by a nitrofuran moiety, which is a five-membered aromatic ring containing both a nitro group and a furan ring. This structural feature is known to contribute to the molecule's ability to interact with biological membranes.

The presence of the nitro group on the furan ring is particularly significant. Nitro groups are electron-withdrawing, which can influence the electronic properties of the furan ring, potentially enhancing the molecule's ability to penetrate lipid membranes. This is because the electron-withdrawing nature of the nitro group can increase the lipophilicity of the molecule, facilitating its passage through the lipid bilayer of the artificial membrane.

Additionally, the molecule contains an acetohydrazide group, which can form hydrogen bonds with the artificial membrane. This interaction can further stabilize the molecule's association with the membrane, potentially enhancing its permeability.

Overall, the combination of the nitrofuran moiety and the acetohydrazide group suggests that the given molecule likely exhibits high permeability in the Parallel Artificial Membrane Permeability Assay.

Final answer: High permeability

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# 24

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

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a complex organic compound that features a naphtho[2,1-b]chromen-4-one core structure, which is a fused ring system combining a naphthalene moiety with a chromenone. This core is further substituted with a morpholine group, which is a six-membered heterocyclic ring containing both oxygen and nitrogen atoms.

The naphtho[2,1-b]chromen-4-one core contributes to the molecule's planar and aromatic characteristics, which are important for its interaction with the artificial membrane. The planar structure allows for stacking interactions with the membrane, while the aromatic nature can facilitate π-π interactions with the membrane's aromatic residues.

The morpholine group introduces a degree of polarity and hydrophilicity to the molecule due to the presence of the oxygen and nitrogen atoms. This can enhance the molecule's solubility in aqueous environments and potentially improve its ability to interact with polar sites on the artificial membrane.

Overall, the combination of the aromatic core and the polar morpholine group suggests that the given molecule may exhibit moderate permeability through the artificial membrane. The aromatic system provides a balance of hydrophobic and hydrophilic interactions, allowing the molecule to traverse the membrane while maintaining sufficient interaction with the membrane's components.

Final answer: Low-to-moderate permeability.

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# 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 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 sulfur in the thiophene ring contributes to the molecule's lipophilicity, which can enhance its ability to permeate lipid membranes.

Additionally, the molecule features a 1-methyltetrazole group attached via a sulfanyl (thioether) linkage. The tetrazole ring is known for its ability to mimic the carboxylic acid group, often used in pharmaceuticals to improve solubility and bioavailability. The methyl group on the tetrazole ring can further influence the molecule's hydrophobicity and steric properties, potentially affecting its permeability.

Overall, the combination of the thienopyrimidine core and the tetrazole group, linked by a thioether bridge, suggests that the given molecule may exhibit moderate to high permeability through the artificial membrane, as it possesses both hydrophobic and polar characteristics that facilitate membrane interaction.

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 amide groups at each end. The presence of the N-hydroxy group on one of the nitrogen atoms introduces a hydroxamic acid functionality, which is known to enhance hydrogen bonding and potentially increase the molecule's polarity.

The artificial membrane used in the PAMPA assay is designed to mimic biological membranes, so the permeability of the given molecule will be influenced by its ability to interact with the membrane and its overall solubility in the medium. The hydroxamic acid group can form strong hydrogen bonds with the membrane, potentially increasing the molecule's affinity for the membrane and enhancing its permeability. However, the overall size and hydrophilic nature of the molecule, due to the hydroxamic acid group, may limit its ability to pass through the membrane, leading to a classification of low-to-moderate permeability.

Therefore, the given molecule is likely to have low-to-moderate permeability in the PAMPA assay.

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:** 1

**Correct:** 1

# Response:
The given molecule is a derivative of 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 influence its interaction with the artificial membrane.

The molecule also features an amino group attached to the pyridinone ring. Amino groups are known for their ability to form hydrogen bonds, which can enhance the molecule's solubility in water and potentially increase its permeability through the membrane.

Additionally, the molecule contains a phenyl ring substituted with a dimethylamino group. The dimethylamino group is a basic moiety that can participate in ionic interactions, which may further influence the molecule's permeability by interacting with the charged sites on the artificial membrane.

Overall, the combination of these functional groups suggests that the given molecule may exhibit moderate to high permeability in the PAMPA assay due to its ability to form hydrogen bonds and ionic interactions, as well as its potential solubility in aqueous environments.

Final answer: High 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 structure is known for its potential to interact with biological membranes due to the presence of both hydrophilic and lipophilic components.

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 ability to interact with biological targets through hydrogen bonding and other non-covalent interactions.

Additionally, the molecule has a dimethoxyphenyl group, which is a phenyl ring substituted with two methoxy groups. These methoxy groups can increase the lipophilicity of the molecule, potentially enhancing its ability to permeate lipid membranes.

The piperidine ring, being a six-membered nitrogen-containing heterocycle, can also contribute to the molecule's solubility and permeability. Piperidine rings are often found in compounds with good oral bioavailability due to their ability to traverse biological membranes.

Overall, the combination of these structural features suggests that the given molecule may have moderate to high permeability in the PAMPA assay, as it possesses both hydrophilic and lipophilic characteristics that facilitate membrane interaction.

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 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 component can contribute to the molecule's ability to interact with biological targets, potentially enhancing its permeability.

Additionally, the presence of a trimethoxyphenyl group, which is a phenyl ring substituted with three methoxy groups, can increase the lipophilicity of the molecule. This increased lipophilicity can enhance the molecule's ability to permeate lipid membranes, such as those found in biological systems.

Overall, the combination of these structural features suggests that the given molecule may have high permeability in the artificial membrane, as the piperidinecarboxamide, thiazole, and trimethoxyphenyl groups collectively contribute to its ability to traverse lipid barriers.

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 N-acylpiperidine, 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. **Piperidine Ring**: The presence of a piperidine ring, a six-membered nitrogen-containing heterocycle, contributes to the molecule's basicity and can enhance its ability to interact with biological membranes. Piperidine rings are often found in pharmacologically active compounds and can improve the molecule's solubility and permeability.

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 electronic properties, potentially affecting its ability to permeate the membrane. Thiazole rings are often involved in hydrogen bonding and π-π interactions, which can influence the molecule's binding affinity and permeability.

3. **Bromophenyl Group**: The presence of a bromine atom on the phenyl ring can increase the molecule's lipophilicity, which may enhance its ability to permeate lipid membranes. However, the bromine atom can also introduce steric hindrance, which might affect the molecule's overall permeability.

4. **Acetamide Group**: The acetamide group is a polar functional group that can participate in hydrogen bonding. This group can enhance the molecule's solubility in aqueous environments, which is important for its permeability across biological membranes.

Overall, the combination of these structural features suggests that the given molecule may have moderate permeability due to the balance between its hydrophilic and lipophilic components. The piperidine and thiazole rings can facilitate interactions with the membrane, while the bromophenyl group and acetamide group may enhance its solubility and 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.

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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 complex structure that includes several key components influencing its permeability. It features a quinoxaline core, which is a bicyclic aromatic compound. This core is known for its planar structure, which can facilitate interactions with biological membranes, potentially enhancing permeability.

Attached to the quinoxaline core is a pyridine ring with a methyl group substitution. Pyridine rings are aromatic and can contribute to the molecule's ability to interact with lipid bilayers, which is crucial for permeability. The presence of the methyl group can increase the hydrophobic character of the pyridine ring, potentially enhancing membrane permeability by increasing lipophilicity.

Additionally, the molecule contains an imidazole ring with a tert-butyl group. Imidazole is a five-membered ring containing nitrogen atoms, which can participate in hydrogen bonding and ionic interactions. The tert-butyl group is a bulky, hydrophobic substituent that can further increase the lipophilicity of the molecule, potentially improving its ability to permeate the membrane.

Overall, the combination of aromatic rings, hydrophobic substituents, and the potential for hydrogen bonding suggests that the given molecule likely exhibits high permeability in the PAMPA assay. The structural features promote interactions with the artificial membrane, enhancing its ability to traverse the barrier.

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:** 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 to understand its permeability.

1. **Imidazolidine-2,4-dione Moiety**: This part of the molecule is a cyclic urea derivative, which is known for its ability to form hydrogen bonds. The presence of this moiety can enhance the molecule's ability to interact with the artificial membrane, potentially increasing its permeability. However, the exact permeability will depend on the overall balance of hydrophilic and hydrophobic interactions.

2. **3-Chlorophenyl Group**: The chlorophenyl group introduces a hydrophobic character to the molecule. The presence of the chlorine atom can also influence the electronic properties of the phenyl ring, potentially affecting the molecule's interaction with the membrane. This group can contribute to the molecule's ability to penetrate the membrane by increasing its lipophilicity.

3. **Pyridine Ring**: The pyridine ring is a heteroaromatic structure that can participate in π-π interactions with the membrane. The nitrogen atom in the pyridine ring can also act as a hydrogen bond acceptor, which may enhance the molecule's interaction with the membrane.

4. **Benzoic Acid Moiety**: The carboxylic acid group in the benzoic acid moiety is a polar functional group that can form hydrogen bonds with the membrane. This group can also ionize under physiological conditions, which may affect the molecule's solubility and permeability. The presence of this group suggests that the molecule may have moderate permeability, as it can interact with both hydrophilic and hydrophobic components of the membrane.

Overall, the given molecule has a combination of hydrophilic and hydrophobic features, which suggests that it may have moderate permeability in the PAMPA assay. The balance of these features will determine its ability to traverse the artificial membrane, with the imidazolidine-2,4-dione and pyridine rings potentially enhancing its interaction with the membrane, while the benzoic acid moiety may limit its permeability due to its polar nature.

Final answer: Low-to-moderate 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:** 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 to understand its permeability:

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

2. **Sulfonamide Group**: The presence of a sulfonamide group is significant in drug design as it can enhance water solubility and influence permeability. Sulfonamides are known to interact with biological membranes, and their presence can affect the molecule's ability to permeate the artificial membrane.

3. **Piperazine Ring**: The piperazine moiety is a common feature in many pharmaceuticals and can contribute to the molecule's basicity. This can enhance the molecule's ability to permeate the membrane by interacting with the lipid bilayer or through ionizable forms.

4. **Thioether Linkage**: The thioether linkage (sulfur atom connecting two carbon atoms) can contribute to the lipophilicity of the molecule, potentially increasing its permeability. However, sulfur can also introduce steric hindrance, which might affect the molecule's ability to fit into the membrane.

5. **Dihydrobenzothiazole Moiety**: This moiety is a bicyclic structure that can contribute to the molecule's rigidity and overall shape. The presence of nitrogen and sulfur in this moiety can also influence the molecule's electronic properties, which may affect its interaction with the membrane.

6. **Amide Linkages**: The molecule contains multiple amide linkages, which can form hydrogen bonds with the membrane. This can either enhance or hinder permeability depending on the orientation and availability of these groups.

Overall, the given molecule's structure suggests a balance of lipophilic and hydrophilic properties, which is typical for molecules designed to interact with biological membranes. The presence of aromatic rings, sulfonamide, and piperazine groups suggests that the molecule may have moderate to high permeability in the PAMPA assay, allowing it to traverse the artificial membrane effectively. 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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# 34

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

**Label:** 0

**Predi:** None

**Correct:** 0

# Response:
The given molecule is a PAMPA permeability assay result, which indicates its ability to permeate through the artificial membrane. The molecule has a high permeability, as suggested by the result of '4'. This means that the molecule can effectively pass through the membrane, which is often indicative of good oral bioavailability and potential drug-like properties.

Final answer: 4

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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. **Piperidine Ring**: The presence of a dimethylamino group attached to a piperidine ring suggests that the molecule has basic properties. Piperidine rings are known for their ability to form hydrogen bonds and ionic interactions, which can enhance the molecule's solubility and permeability. The dimethylamino group can also participate in hydrogen bonding and may increase the molecule's overall polarity, potentially improving its permeability.

2. **Phenyl Group**: The phenyl group attached to the piperidine ring is a hydrophobic moiety. This hydrophobic character can facilitate the molecule's interaction with the lipid components of the artificial membrane, potentially enhancing its permeability. However, the balance between hydrophilic and hydrophobic properties will be crucial in determining the overall permeability.

3. **Quinazolinone Core**: The quinazolinone structure is a bicyclic system that can contribute to the molecule's rigidity and planarity. This core can interact with the artificial membrane through π-π stacking interactions, which are common in aromatic systems. The presence of nitrogen atoms in the quinazolinone ring can also participate in hydrogen bonding, which may further influence permeability.

4. **Thiazole Ring**: The thiazole ring is another heterocyclic component that can contribute to the molecule's electronic properties. The sulfur and nitrogen atoms in the thiazole ring can engage in polar interactions, which may enhance the molecule's ability to permeate the artificial membrane.

Overall, the given molecule's structure suggests a balance of hydrophilic and hydrophobic properties, with multiple functional groups capable of forming various interactions with the artificial membrane. These features collectively indicate that the molecule likely exhibits high permeability in the PAMPA assay.

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, each 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 nature often allows for favorable stacking interactions with the membrane, potentially enhancing 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. However, the balance between hydrophilic and lipophilic properties will determine the overall permeability.

3. **Morpholine Substituent**: The morpholine group is a heterocyclic amine that can enhance the molecule's solubility in aqueous environments. This group can also participate in hydrogen bonding, which may facilitate interaction with the membrane. The presence of the morpholine ring can also introduce some steric hindrance, potentially affecting the molecule's ability to permeate the membrane.

4. **Ethyl Linkage**: The ethyl linkage connecting the morpholine to the quinazoline core provides flexibility to the molecule. This flexibility can allow the molecule to adopt conformations that optimize its interaction with the membrane, potentially enhancing permeability.

Overall, the given molecule's structure suggests a balance between hydrophilic and lipophilic properties, with aromatic and heterocyclic components that can facilitate interactions with the artificial membrane. These features collectively suggest that the molecule may exhibit high permeability in the PAMPA assay.

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 potential impact on permeability:

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.

2. **Chloro Substituent**: The chloro group attached to the pyrazine ring introduces a degree of lipophilicity to the molecule. Chlorine atoms can increase the molecule's ability to interact with lipid membranes, potentially enhancing permeability.

3. **Benzoxazole Moiety**: The benzoxazole group is a bicyclic structure that combines aromatic and heterocyclic characteristics. This moiety can contribute to the molecule's overall stability and rigidity, which may affect its ability to traverse the membrane. The aromatic nature of benzoxazole can also facilitate π-π interactions with the membrane.

4. **Thiadiazole Ring**: The thiadiazole ring is another heterocyclic component that can influence the molecule's electronic properties. The sulfur and nitrogen atoms in this ring can participate in hydrogen bonding and other polar interactions, which may enhance permeability.

5. **Carboxamide Group**: The carboxamide functional group is polar and can form hydrogen bonds, which are crucial for solubility and permeability. This group can interact with the PAMPA membrane, potentially facilitating passage through the membrane.

6. **Pyrimidine Ring**: The pyrimidine ring is another aromatic heterocycle that can contribute to the molecule's overall stability and ability to interact with the membrane. Its presence can enhance the molecule's ability to engage in π-π stacking and other non-covalent interactions.

Overall, the given molecule exhibits a balance of polar and non-polar characteristics, with multiple functional groups capable of interacting with the PAMPA membrane. These features suggest that the molecule likely has high permeability, as it can effectively interact with and traverse the artificial membrane.

Final answer: High permeability.

------
# 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 potential 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, which can increase the lipophilicity of the molecule. This increased lipophilicity can enhance the molecule's ability to traverse lipid membranes, suggesting high permeability.

3. **Phenoxy Group**: The phenoxy group, which is an ether linkage between a phenyl ring and an oxygen atom, can increase the molecule's flexibility and solubility. This flexibility can allow the molecule to adapt to the membrane structure, potentially facilitating its passage through the artificial membrane.

4. **Methylsulfanyl Linkage**: The presence of a methylsulfanyl group (a sulfur atom bonded to a methyl group) can contribute to the molecule's overall lipophilicity. Sulfur-containing groups can also participate in specific interactions with the membrane, potentially enhancing permeability.

5. **Acetic Acid Moiety**: The acetic acid group introduces a polar, hydrophilic component to the molecule. While this group can enhance solubility in aqueous environments, it may also create a balance between hydrophilicity and lipophilicity, which is crucial for membrane permeability. The presence of this group suggests that the molecule may have moderate permeability, as it can interact with both hydrophilic and hydrophobic environments.

Overall, the given molecule's combination of lipophilic and hydrophilic features, along with its structural rigidity and flexibility, suggests that it may have high permeability in the PAMPA assay. The balance of these features allows the molecule to effectively interact with the artificial membrane, facilitating its passage.

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:** 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 to understand its permeability characteristics.

1. **Piperazine Ring**: The presence of a piperazine ring, which is a six-membered ring containing two nitrogen atoms, is a common feature in many pharmaceuticals. Piperazine rings are known for their ability to enhance the solubility and permeability of molecules. This is due to the presence of nitrogen atoms that can participate in hydrogen bonding and ionic interactions, which can facilitate the passage of the molecule through the artificial membrane.

2. **Pyridine Rings**: The given 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 contribute to the molecule's ability to interact with the artificial membrane through π-π stacking interactions and hydrogen bonding. However, the basicity of the nitrogen in the pyridine rings can also lead to increased solubility in water, which may enhance permeability.

3. **Carbothioamide Group**: The carbothioamide group in the molecule introduces a sulfur atom, which can participate in additional hydrogen bonding and dipole-dipole interactions. This group can also contribute to the overall polarity of the molecule, potentially enhancing its permeability.

4. **Dimethyl Substitution**: The dimethyl groups on the pyridine ring can increase the lipophilicity of the molecule. While increased lipophilicity can sometimes enhance membrane permeability, it can also hinder permeability if the molecule becomes too hydrophobic. In this case, the balance between hydrophilic and lipophilic properties will determine the overall permeability.

Considering these structural features, the given molecule is likely to exhibit a balance of hydrophilic and lipophilic properties, which is typical for molecules designed to interact with biological membranes. The presence of nitrogen atoms in the piperazine and pyridine rings, along with the carbothioamide group, suggests that the molecule can form hydrogen bonds and ionic interactions with the artificial membrane, potentially leading to high permeability. However, the dimethyl substitution may slightly reduce permeability by increasing lipophilicity. Overall, the given molecule is expected to have high permeability in the PAMPA assay.

Final answer: High 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, which is a class of compounds known for their potential pharmacological activity. The structure of the given molecule includes several key features that influence its permeability:

1. **Piperazine Ring**: The presence of a piperazine ring is a common feature in many pharmaceuticals, contributing to the molecule's ability to interact with biological targets. Piperazine rings are generally flexible and can adopt various conformations, which may enhance the molecule's ability to permeate biological membranes.

2. **Difluorophenyl Group**: The difluorophenyl moiety introduces fluorine atoms into the structure. Fluorine atoms can increase the lipophilicity of the molecule, which may enhance its ability to permeate lipid membranes. Additionally, fluorine can influence the electronic properties of the molecule, potentially affecting its interaction with biological targets.

3. **Pyridinyl Group**: The pyridinyl group, particularly with methyl substitution, can contribute to the molecule's overall lipophilicity. Pyridine rings are aromatic and can participate in π-π interactions with biological membranes or proteins, potentially aiding in permeability.

4. **Carbothioamide Group**: The carbothioamide functional group is a sulfur-containing moiety that can influence the molecule's polarity and hydrogen bonding capabilities. This group may enhance the molecule's solubility and permeability by interacting with polar environments within the membrane.

Overall, the combination of these structural features suggests that the given molecule may exhibit high permeability in the PAMPA assay due to its balanced lipophilicity and potential for favorable interactions with the artificial membrane.

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:** 0

**Correct:** 0

# 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 properties.

The presence of the sulfonamide group, which includes a sulfonyl functional group attached to an amine, is crucial for the molecule's ability to interact with biological membranes. This group can enhance the molecule's solubility and facilitate its passage through lipid membranes due to its polar nature.

Additionally, the molecule contains a dichlorophenyl moiety, which can influence its permeability. The presence of chlorine atoms on the phenyl ring can increase the lipophilicity of the molecule, potentially enhancing its ability to permeate lipid membranes. However, the balance between hydrophilic and lipophilic properties is essential for determining the overall permeability.

The isoxazole ring in the molecule adds another layer of complexity. Isoxazole is a heterocyclic compound that can contribute to the molecule's stability and binding interactions with biological targets. While it may not directly affect permeability, it can influence the overall pharmacokinetic profile of the molecule.

Overall, the combination of the sulfonamide group, dichlorophenyl moiety, and isoxazole ring suggests that the given molecule may exhibit moderate to high permeability in the PAMPA assay, depending on the balance between its hydrophilic and lipophilic properties.

Final answer: Low-to-moderate 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 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 is a key structural feature. Piperazine rings are known for their ability to enhance the solubility and permeability of molecules. 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 moiety contributes to the lipophilicity of the molecule. Chlorine atoms increase the hydrophobic character, which can enhance membrane permeability by facilitating passage through the lipid bilayer of the artificial membrane. However, the presence of two chlorine atoms may also introduce steric hindrance, potentially affecting the molecule's overall permeability.

3. **Pyridinyl Group**: The pyridinyl group, specifically the 6-methylpyridinyl, adds aromaticity and basicity to the molecule. The nitrogen in the pyridine ring can engage in hydrogen bonding and ionic interactions, which may aid in permeability. The methyl group on the pyridine ring can further modulate lipophilicity and steric properties, influencing the molecule's ability to traverse the membrane.

4. **Carbothioamide Group**: The carbothioamide functional group is a sulfur-containing moiety that can participate in hydrogen bonding and dipole interactions. This group may enhance the molecule's solubility and permeability by interacting with the polar components of the artificial membrane.

Overall, the given molecule's structure suggests a balance of hydrophilic and lipophilic properties, which is typical for molecules with moderate to high permeability in PAMPA assays. The piperazine ring and aromatic groups contribute to its ability to interact with the membrane, while the dichlorophenyl and pyridinyl groups enhance lipophilicity. Therefore, the given molecule is likely to exhibit high permeability in the PAMPA assay.

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 membranes, which can influence its permeability.

In the given molecule, the sulfonamide group is attached to a phenyl ring that is further substituted with a 3-chloro-4-fluorophenyl group. The presence of halogen atoms, such as chlorine and fluorine, can increase the lipophilicity of the molecule, which may enhance its ability to permeate lipid membranes. However, these halogen atoms can also introduce steric hindrance and electronic effects that may affect the overall permeability.

Additionally, the molecule contains an isoxazole ring, which is a five-membered heterocyclic compound containing nitrogen and oxygen. The presence of this ring can contribute to the molecule's overall polarity and may influence its interaction with the artificial membrane.

The acetamide group in the molecule can also play a role in its permeability. Amide groups are generally polar and can form hydrogen bonds, which may affect the molecule's solubility and permeability.

Overall, the combination of these functional groups suggests that the given molecule may have moderate permeability in the artificial membrane assay. The sulfonamide group and halogen substitutions may enhance permeability, while the isoxazole and acetamide groups may introduce some polarity and potential for hydrogen bonding, which could balance the overall permeability.

Final answer: Low-to-moderate permeability.

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# 44

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

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a derivative of phenazine, specifically a hexahydrophenazine. This means that the phenazine core, which is typically a planar aromatic system, has been partially hydrogenated, resulting in a more saturated and less planar structure. 

In the context of the Parallel Artificial Membrane Permeability Assay (PAMPA), the permeability of a molecule is influenced by its lipophilicity, molecular size, and the presence of functional groups that can interact with the membrane. The partial hydrogenation of the phenazine core in the given molecule likely increases its lipophilicity compared to the fully aromatic phenazine. This increased lipophilicity can enhance the molecule's ability to interact with the lipid-like environment of the artificial membrane, potentially leading to higher 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 form hydrogen bonds or ionic interactions with the membrane. Without specific data on these factors, we can infer that the given molecule is likely to exhibit moderate to high permeability due to its increased lipophilicity from the hexahydrogenation of the phenazine core.

Final answer: Low-to-moderate 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 tetracyclic structure that is characteristic of many biologically active alkaloids. This structural complexity often contributes to the molecule's ability to interact with biological targets, such as receptors or enzymes, due to its rigid and defined three-dimensional shape.

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

1. **Polycyclic Structure**: The rigid, multi-ring system of the yohimban framework can enhance the molecule's ability to traverse lipid membranes, as it provides a stable conformation that can interact with the lipid bilayer.

2. **Hydroxyl Groups**: The presence of hydroxyl groups in the molecule increases its hydrophilicity, which can 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 their positioning and the membrane's properties.

3. **Methoxy Groups**: The methoxy groups contribute to the molecule's lipophilicity, which can enhance its ability to permeate lipid membranes. These groups can also influence the electronic properties of the molecule, potentially affecting its interaction with the membrane.

4. **Overall Lipophilicity**: The balance between the hydrophilic hydroxyl groups and the lipophilic methoxy groups suggests that the given molecule may have moderate permeability. The methoxy groups can help the molecule penetrate the lipid membrane, while the hydroxyl groups may provide some solubility and interaction with the membrane.

Based on these structural considerations, the given molecule is likely to 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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# 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 with three ketone groups and two methyl groups attached to it. The presence of these functional groups and the overall structure of the molecule play a significant role in its permeability.

The purine ring system is relatively planar and aromatic, which can facilitate interactions with the artificial membrane. The ketone groups increase the molecule's polarity, which can enhance its ability to form hydrogen bonds with the membrane. However, the presence of methyl groups can increase the hydrophobic character of the molecule, potentially aiding in its permeability by interacting with the lipid components of the membrane.

Overall, the balance of polar and non-polar characteristics in the given molecule suggests that it may have moderate permeability in the PAMPA assay. The ketone groups and the purine ring system contribute to its ability to interact with the membrane, while the methyl groups may enhance its permeability by increasing its hydrophobic interactions.

Final answer: Low-to-moderate permeability.

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# 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:

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. The presence of nitrogen atoms in the imidazo ring can also contribute to hydrogen bonding and polar interactions, potentially increasing permeability.

2. **Chlorine Substitution**: The chlorine atom on the imidazo[1,2-a]pyridine ring can influence the molecule's lipophilicity. Chlorine is a relatively electronegative atom, which can enhance the molecule's ability to penetrate lipid membranes by increasing its overall hydrophobic character.

3. **Piperidin-1-yl Group**: The piperidine ring is a saturated, six-membered nitrogen-containing heterocycle. This group can increase the molecule's solubility and flexibility, which may aid in its permeation through the artificial membrane. The nitrogen in the piperidine ring can also participate in hydrogen bonding, further influencing permeability.

4. **Pyridin-2-amine Moiety**: The pyridine ring is another aromatic heterocycle that can contribute to the molecule's overall planarity and aromaticity. The amine group attached to the pyridine can form hydrogen bonds, which may enhance interaction with the membrane and improve permeability.

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 often desirable for good permeability in PAMPA assays. The presence of nitrogen atoms and the chlorine substitution likely enhance its ability to interact with the artificial membrane, indicating that the molecule is likely to have high permeability in the PAMPA assay.

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:** 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 common pharmacophore in medicinal chemistry, often associated with good membrane permeability due to its planar structure. This allows the molecule to interact favorably with lipid bilayers.

2. **Ethylsulfonyl Group**: The presence of an ethylsulfonyl group attached to the phenyl ring introduces a polar and electron-withdrawing sulfonyl group. This can enhance the molecule's solubility in aqueous environments, which is beneficial for permeability through biological membranes.

3. **Pyridine Ring**: The pyridine ring is a heteroaromatic structure that can participate in hydrogen bonding and π-π interactions with the membrane. This can facilitate the passage of the molecule through the membrane.

4. **Carbonyl Groups**: The molecule contains multiple carbonyl groups, which are polar and can form hydrogen bonds with the membrane. This can enhance the molecule's interaction with the membrane and potentially increase its permeability.

5. **Trifluoromethyl Group**: The trifluoromethyl group is highly electronegative and lipophilic, which can enhance the molecule's ability to penetrate lipid membranes. This group can also increase the metabolic stability of the molecule.

Overall, the combination of these structural features suggests that the given molecule is likely to have high permeability in the PAMPA assay. The balance of hydrophilic and lipophilic properties, along with the presence of functional groups that can interact with the membrane, supports its potential to traverse the artificial membrane efficiently.

Final answer: High 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 molecule increases its hydrophilicity. These polar groups can form hydrogen bonds with the artificial membrane, potentially enhancing its interaction with the membrane and improving permeability.

2. **Sulfanyl Group**: The sulfanyl group (a sulfur atom bonded to a phenyl ring) can contribute to the molecule's lipophilicity. While it may provide some degree of hydrophobic interaction with the membrane, its overall effect on permeability will depend on the balance with the hydrophilic groups.

3. **Phenyl Rings**: The phenyl rings in the structure contribute to the molecule's hydrophobic character. These aromatic rings can interact with the hydrophobic regions of the artificial membrane, potentially facilitating permeation.

4. **Methoxy Group**: The methoxy group attached to a phenyl ring can increase the molecule's lipophilicity. This group can enhance the ability of the molecule to traverse the membrane by interacting with the lipid components.

5. **Chloro Substituent**: The chloro group on the phenyl ring can also contribute to the lipophilicity of the molecule. However, it may also introduce steric hindrance, which could affect the molecule's ability to fit into the membrane pores.

Overall, the given molecule has a combination of hydrophilic and hydrophobic features, which suggests that it may have moderate permeability in the PAMPA assay. The balance between these features will determine how well the molecule can permeate the artificial membrane.

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, which influence its permeability in the PAMPA assay. 

Firstly, the molecule contains a cyclopentyl group, which is a non-polar, hydrophobic ring. This hydrophobic character can enhance the molecule's ability to permeate through lipid membranes, suggesting a potential for high permeability.

Secondly, the molecule features a pyrrolo[2,3-b]pyridine moiety. This bicyclic structure includes both a pyrrole and a pyridine ring, which can contribute to the molecule's overall polarity and potential for hydrogen bonding. The presence of nitrogen atoms in the pyridine ring can also enhance the molecule's ability to interact with polar environments, which might affect its permeability.

Additionally, the molecule has a phenyl group attached to the pyrrolo[2,3-b]pyridine, which is a planar, aromatic structure. Aromatic rings can increase the molecule's lipophilicity, potentially improving its permeability through the lipid-rich environment of the artificial membrane.

Finally, the molecule contains a carboxylic acid functional group. This acidic group is polar and can form hydrogen bonds, which may influence the molecule's solubility and permeability. The presence of the carboxylic acid group can also affect the molecule's ionization state, which is crucial for its interaction with the artificial membrane.

Overall, the combination of hydrophobic and polar features in the given molecule suggests that it may exhibit high permeability in the PAMPA assay, as it can interact with both lipid and polar environments.

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, which is structurally related to the kinase inhibitor rilpivirine. The presence of the quinazoline core is significant as it is a common scaffold in many kinase inhibitors, which often have high permeability due to their planar and aromatic nature. This allows them to easily traverse biological membranes.

The fluorine atom on the quinazoline ring can enhance the molecule's lipophilicity, potentially increasing its permeability by improving its ability to dissolve in lipid membranes. Fluorine is a small and highly electronegative atom, which can also influence the electronic distribution within the molecule, potentially affecting its interaction with the artificial membrane.

The molecule also contains a triazinyl group, which is a heterocyclic structure that can contribute to the molecule's overall stability and binding affinity. The presence of an amino group linked to the triazinyl moiety can enhance hydrogen bonding interactions, which may play a role in the molecule's permeability by facilitating interactions with the membrane or the PAMPA assay components.

Overall, the given molecule's structural features, such as the quinazoline core, fluorine substitution, and triazinyl group, suggest that it likely exhibits high permeability in the PAMPA assay.

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. 

The molecule contains a pyrrolopyridine moiety, which is a fused ring system combining pyrrole and pyridine. This structure is known for its planar aromatic nature, which can facilitate interactions with the artificial membrane, potentially enhancing permeability. The presence of the pyrrolopyridine moiety suggests that the molecule may have a favorable interaction with the membrane, contributing to its permeability.

Additionally, the molecule includes a pyrimidine ring, which is another aromatic heterocycle. Pyrimidines are often involved in hydrogen bonding and π-π stacking interactions, which can also enhance the molecule's ability to permeate the membrane.

The molecule also features an amide linkage, specifically a benzamide group. Amides are polar and can participate in hydrogen bonding, which may influence the molecule's solubility and permeability. The presence of the amide group can enhance the molecule's ability to interact with the polar components of the artificial membrane.

The methyl and isopropyl groups attached to the aromatic rings introduce hydrophobic characteristics, which can affect the molecule's overall lipophilicity. These groups may enhance the molecule's ability to traverse the lipid-rich environment of the artificial membrane.

Overall, the combination of aromatic rings, heterocycles, and functional groups in the given molecule suggests that it may have a favorable balance of hydrophobic and hydrophilic interactions, which can contribute to its permeability in the PAMPA assay. Therefore, the given molecule is likely to exhibit high permeability in the artificial membrane.

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 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. **Indole Core**: The presence of an indole moiety, which is a bicyclic structure consisting of a benzene ring fused to a pyrrole ring, contributes to the molecule's overall rigidity and planarity. This structural feature can enhance the molecule's ability to interact with the artificial membrane, potentially increasing its permeability.

2. **Hydroxy Group**: The hydroxy group attached to the indole ring can form hydrogen bonds with the membrane, which may facilitate the molecule's passage through the membrane. This functional group can also increase the molecule's solubility in aqueous environments, which is beneficial for permeability.

3. **Piperazine Ring**: The inclusion of a piperazine ring, which is a six-membered heterocyclic amine, introduces basicity to the molecule. This can affect the molecule's ionization state at physiological pH, potentially influencing its interaction with the membrane and its overall permeability.

4. **Phenyl and Methylideneamino Linkages**: The phenyl group and the methylideneamino linkage contribute to the molecule's hydrophobic character. These groups can enhance the molecule's ability to traverse lipid membranes by interacting with the hydrophobic regions of the artificial membrane.

5. **Ester Group**: The ester group in the molecule can be susceptible to hydrolysis, which might affect the molecule's stability and permeability. However, in the context of the PAMPA assay, the ester group is likely to remain intact, allowing the molecule to maintain its structural integrity and permeability.

Overall, the given molecule exhibits a combination of hydrophobic and hydrophilic properties, along with structural features that promote interaction with the artificial membrane. These characteristics suggest that the molecule would have high permeability in the PAMPA assay.

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:** 0

**Correct:** 1

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

The molecule contains a naphthalene moiety, which is a polycyclic aromatic hydrocarbon. This structure is known for its hydrophobic characteristics, which can enhance the molecule's ability to interact with lipid membranes. The presence of the naphthalene ring suggests that the molecule may have a degree of lipophilicity, which can contribute to its permeability through the artificial membrane.

Additionally, the molecule features an oxazole ring, which is a five-membered heterocyclic compound containing both nitrogen and oxygen. The oxazole ring can introduce some degree of polarity to the molecule, which may affect its solubility and permeability. The presence of this heterocyclic ring can also influence the molecule's ability to form hydrogen bonds, potentially affecting its interaction with the membrane.

The methoxy group attached to the oxazole ring adds to the molecule's polarity and can enhance its solubility in polar solvents. This group may also participate in hydrogen bonding, which can further influence the molecule's permeability.

Finally, the carboxylic acid group is a highly polar functional group that can significantly impact the molecule's solubility and permeability. Carboxylic acids are known to ionize in aqueous environments, which can enhance the molecule's solubility in water and potentially improve its permeability through the membrane.

Overall, the combination of hydrophobic aromatic systems and polar functional groups suggests that the given molecule may exhibit moderate permeability in the PAMPA assay. The balance of lipophilic and hydrophilic properties can facilitate its passage through the artificial membrane, but the exact permeability would depend on the specific conditions of the assay.

Final answer: Low-to-moderate 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 this 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 lipophilic 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 can enhance the molecule's ability to penetrate lipid membranes by increasing its hydrophobic character. This group can also participate in hydrophobic interactions with the lipid components of the membrane.

3. **Methoxy and Methyl Substituents**: The methoxy and methyl groups increase the lipophilicity of the molecule, which can further enhance its permeability. These groups can also influence the molecule's overall conformation and electronic distribution, potentially affecting its interaction with the artificial membrane.

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 allowing it to interact with the membrane in a more specific manner.

Overall, the combination of these structural features suggests that the given molecule would exhibit high permeability in the PAMPA assay. The balance of lipophilic and polar groups allows it to effectively interact with the artificial membrane, facilitating its passage through the membrane.

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 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 pyridine ring attached to the quinazoline core. Pyridine is a six-membered aromatic ring with one nitrogen atom, which can contribute to the molecule's ability to participate in hydrogen bonding and other polar interactions.

Additionally, the molecule has a difluorophenyl group attached to the nitrogen atom of the quinazoline core. The presence of fluorine atoms can increase the lipophilicity of the molecule, potentially enhancing its ability to permeate lipid membranes. Fluorine atoms can also influence the electronic properties of the molecule, which may affect its binding affinity to biological targets.

Overall, the combination of the quinazoline core, pyridine ring, and difluorophenyl group suggests that the given molecule may have moderate to high permeability in the PAMPA assay, as these structural features are commonly associated with good membrane permeability and bioavailability.

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:** 1

**Correct:** 1

# 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 features a quinazoline core, which is a bicyclic structure composed 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 two pyridinyl groups attached to the nitrogen atoms of the quinazoline core. These pyridinyl groups are aromatic heterocycles, which can enhance the molecule's ability to participate in π-π stacking interactions and hydrogen bonding, potentially increasing its binding affinity to biological targets.

The presence of a difluorophenyl group attached to the quinazoline core introduces fluorine atoms, which can significantly influence the molecule's physicochemical properties. Fluorine is highly electronegative, and its presence can increase the lipophilicity of the molecule, potentially enhancing its ability to permeate lipid membranes. Additionally, fluorine can affect the metabolic stability of the molecule, as it can make the compound more resistant to enzymatic degradation.

Overall, the structural features of the given molecule, including the quinazoline core, pyridinyl groups, and difluorophenyl moiety, suggest that it may have high permeability in the PAMPA assay due to its aromatic and lipophilic characteristics, which are conducive to membrane permeation.

Final answer: High 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.

In the given molecule, the sulfonamide group is attached to a benzene ring, which is further substituted with a hydroxy group and a nitrophenyl group. The hydroxy group can participate in hydrogen bonding, which may increase the molecule's solubility and interaction with polar environments. The nitrophenyl group introduces additional electron-withdrawing properties, which can affect the molecule's overall electronic distribution and potentially its reactivity.

The presence of a thiazole ring, which is a five-membered ring containing both sulfur and nitrogen, contributes to the molecule's heterocyclic nature. This ring can enhance the molecule's ability to interact with biological systems due to its aromaticity and potential for hydrogen bonding or π-π interactions.

The benzene ring linked to the thiazole ring through an amino group suggests that the molecule has a planar structure, which can facilitate its passage through lipid membranes. The overall structure, with its combination of polar and non-polar regions, suggests that the given molecule may have moderate permeability through the artificial membrane, as it possesses both hydrophilic and hydrophobic characteristics. The balance of these properties allows the molecule to interact with both aqueous and lipid environments, which is essential for its potential biological activity.

Final answer: Low-to-moderate permeability.

------
# 59

**SMILES:** C1=CC(=CC=C1NCC2=C(C=C(C=C2)N)O)[S+](=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 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.

In the given molecule, the sulfonamide group is attached to a phenyl ring, which is further substituted with an amino group. This substitution can increase the molecule's polarity and potentially improve its solubility in aqueous environments, which is beneficial for permeability through biological membranes.

Additionally, the molecule contains a thiazole ring, which is a five-membered ring containing both sulfur and nitrogen. The presence of this heterocyclic ring can contribute to the molecule's ability to form hydrogen bonds and engage in π-π interactions, which can further influence its permeability.

The amino group on the phenyl ring can also participate in hydrogen bonding, which may enhance the molecule's interaction with the artificial membrane. However, the overall size and complexity of the molecule, along with the presence of multiple functional groups, may also introduce steric hindrance and reduce its permeability.

Considering these structural features, the given molecule is likely to exhibit moderate permeability in the PAMPA assay, as the balance between hydrophilic and hydrophobic interactions, along with steric factors, will dictate its passage through the artificial membrane.

Final answer: Low-to-moderate permeability.

------
# 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 characterized by the presence of a sulfonamide group. This functional group is known for its ability to interact with biological membranes, often enhancing the molecule's permeability. 

The structure of the given molecule includes an aromatic sulfonamide moiety, which is a key feature that can facilitate membrane permeability. The sulfonamide group is polar and can form hydrogen bonds, which may enhance the molecule's solubility and permeability across lipid membranes. 

Additionally, the presence of an amino group attached to the phenyl ring can increase the molecule's basicity and ability to form hydrogen bonds, potentially improving its interaction with the artificial membrane. The methoxy group on the phenyl ring can also contribute to the molecule's lipophilicity, which may aid in its permeability by increasing its ability to dissolve in lipid bilayers.

The thiazole ring in the molecule is a heterocyclic aromatic compound that can enhance the molecule's stability and binding affinity to the membrane. The nitrogen and sulfur atoms in the thiazole ring can participate in additional hydrogen bonding and dipole interactions, which may further facilitate the molecule's permeability.

Overall, the combination of these functional groups 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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# 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 an aromatic amide, which suggests that it has a structure that includes an amide group attached to an aromatic ring. This structural feature is significant in determining the molecule's permeability.

The presence of the aromatic ring, specifically the phenyl group with a methoxy substituent, contributes to the molecule's lipophilicity, which can enhance its ability to permeate through lipid membranes. The methoxy group can also influence the electronic properties of the aromatic ring, potentially affecting the molecule's interaction with the artificial membrane.

The pyrrole ring in the molecule, which is a five-membered heterocyclic aromatic ring, can also contribute to the molecule's overall aromatic character. The presence of methyl groups on the pyrrole ring can increase the molecule's hydrophobicity, further enhancing its permeability through the membrane.

The amide group in the molecule is polar and can form hydrogen bonds, which may facilitate interactions with the artificial membrane. However, the overall structure, with its aromatic and hydrophobic components, suggests that the molecule's permeability is likely influenced more by its lipophilic characteristics than by the polar nature of the amide group.

Considering these structural features, the given molecule is likely to exhibit high permeability through the artificial membrane.

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 functional group attached to an aromatic ring. This structural feature is significant in determining the molecule's permeability.

The presence of the aromatic ring, specifically the chlorophenyl group, contributes to the molecule's lipophilicity, which can enhance its ability to permeate through lipid membranes. The chlorophenyl group is a common motif in drug design, often used to improve membrane permeability and bioavailability.

Additionally, the pyrrole ring in the given molecule is a heterocyclic aromatic compound, which can also contribute to the molecule's overall lipophilicity. The presence of methyl groups on the pyrrole ring can further increase the molecule's hydrophobic character, potentially enhancing its permeability through the artificial membrane.

The amide linkage in the molecule is a polar functional group, which can form hydrogen bonds with the artificial membrane. This interaction can influence the molecule's permeability by affecting its solubility and interaction with the membrane.

Overall, the combination of aromatic and heterocyclic structures, along with the amide linkage, suggests that the given molecule likely exhibits high permeability in the Parallel Artificial Membrane Permeability Assay (PAMPA).

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. This structure is known for its potential biological activity and is often used in pharmaceuticals.

The presence of the amino group on the thienopyrimidine core can enhance the molecule's ability to form hydrogen bonds, which may increase its interaction with the artificial membrane. This functional group can also contribute to the molecule's solubility and permeability.

The dimethoxyphenyl group attached to the thienopyrimidine core introduces two methoxy groups, which are electron-donating. These groups can increase the lipophilicity of the molecule, potentially enhancing its ability to permeate the lipid-like environment of the artificial membrane.

Overall, the combination of the thienopyrimidine core, the amino group, and the dimethoxyphenyl group suggests that the given molecule may exhibit moderate to high permeability in the PAMPA assay, as these structural features can facilitate interactions with the artificial membrane and enhance its permeability.

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. The pyridine ring, being aromatic, can also contribute to the molecule's ability to interact with lipid membranes.

2. **Carboxamide Group**: The carboxamide group is polar and can form hydrogen bonds with the artificial membrane. This can enhance the molecule's interaction with the membrane, potentially increasing permeability. However, it can also introduce some degree of polarity, which might limit permeability depending on the balance with other hydrophobic parts of the molecule.

3. **3,4-Dichlorophenyl Carbamoylamino Moiety**: The dichlorophenyl group is hydrophobic and can enhance the lipophilicity of the molecule, promoting membrane permeability. The chlorine atoms can also increase the molecule's ability to penetrate lipid bilayers due to their electron-withdrawing properties, which can affect the electronic distribution and enhance lipophilicity.

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

Overall, the given molecule contains a combination of hydrophobic and polar features. The aromatic and heterocyclic rings, along with the dichlorophenyl group, suggest that the molecule has a significant hydrophobic character, which is likely to enhance its permeability through the artificial membrane. The presence of polar groups like the carboxamide may also facilitate interactions with the membrane, potentially aiding in permeability. Therefore, the given molecule is expected to have high permeability in the PAMPA assay.

Final answer: High permeability

------
# 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 potential impact on permeability:

1. **Pyridine Ring**: The presence of a pyridine ring, which is a nitrogen-containing heterocycle, can enhance the molecule's ability to interact with the artificial membrane. Pyridine rings are known for their basicity and ability to form hydrogen bonds, which can facilitate interactions with the membrane. This can contribute to moderate to high permeability, depending on the overall balance of hydrophilic and lipophilic properties.

2. **Ethoxyphenyl Group**: The ethoxyphenyl moiety introduces an aromatic ring with an ethoxy substituent. The ethoxy group is relatively small and hydrophobic, which can enhance the lipophilicity of the molecule. This can improve the molecule's ability to traverse the lipid-like environment of the artificial membrane, potentially leading to higher permeability.

3. **Oxadiazole Ring**: The oxadiazole ring is a heterocyclic compound that can contribute to the molecule's overall stability and rigidity. This ring can also participate in hydrogen bonding and dipole interactions, which may enhance the molecule's interaction with the membrane. The presence of this ring can contribute to moderate permeability.

4. **Pyrrolidinone Moiety**: The pyrrolidinone group is a lactam, which is a cyclic amide. This group can engage in hydrogen bonding, which may enhance the molecule's solubility and interaction with the membrane. However, the cyclic nature of the lactam can also introduce some rigidity, which might affect the overall flexibility of the molecule and its ability to permeate the membrane.

Overall, the given molecule contains a combination of aromatic and heterocyclic features that can enhance its interaction with the artificial membrane. The balance of hydrophilic and lipophilic properties, along with the potential for hydrogen bonding and dipole interactions, suggests that the molecule may exhibit high permeability in the PAMPA assay.

Final answer: High permeability.

------
# 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 enhance the lipophilicity of the molecule. This can increase the molecule's ability to traverse lipid membranes, contributing to higher permeability.

2. **Aromatic Amine**: The molecule contains a dimethyl-substituted aniline group, which is an aromatic amine. Aromatic amines can participate in hydrogen bonding and π-π interactions, which may facilitate interaction with the artificial membrane. However, the presence of electron-donating methyl groups can also increase the lipophilicity of the aromatic ring, potentially enhancing permeability.

3. **Furan Ring**: The furan ring, another five-membered heterocycle, contributes to the molecule's overall aromatic character and lipophilicity. Furans are known to be relatively non-polar, which can aid in membrane permeability.

4. **Amide Linkage**: The acetamide group introduces a polar amide linkage, which can form hydrogen bonds with the artificial membrane. This can enhance the molecule's interaction with the membrane, potentially increasing permeability. However, the presence of the amide group also introduces some degree of polarity, which can balance the lipophilic effects of the other groups.

Overall, the given molecule's structure suggests a balance between lipophilic and polar characteristics. The thiazole and furan rings contribute to lipophilicity, while the aromatic amine and amide linkage introduce polar interactions. This balance suggests that the molecule would exhibit 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

------
# 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.

In the given molecule, the sulfonamide group is 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 increase the electron density on the benzene ring, potentially affecting the molecule's reactivity and interaction with the artificial membrane.

The hydroxyphenyl group contains a hydroxyl group, which is also capable of forming hydrogen bonds. This can enhance the molecule's solubility in water and its ability to interact with polar environments, such as the artificial membrane used in the PAMPA assay.

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 its ability to interact with biological targets due to the heteroatoms, which can participate in various non-covalent interactions.

Overall, the combination of these functional groups suggests that the given molecule may have moderate permeability in the PAMPA assay. The sulfonamide group, along with the hydroxy and methoxy groups, likely contribute to the molecule's ability to interact with the artificial membrane, while the thiazole ring may provide additional stability and interaction potential.

Final answer: Low-to-moderate permeability.

------
# 68

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

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a derivative of hydroxycoumarin, which is known for its potential biological activities, including anticoagulant and antimicrobial properties. The structure of the given molecule includes a coumarin core, which is a bicyclic compound consisting of a benzene ring fused to a lactone ring. This core is modified with a chlorine atom and a 3,5-dichloro-4-hydroxyphenylmethylidene group.

The presence of the dichloro and hydroxy groups on the phenyl ring can influence the molecule's polarity and hydrogen bonding capabilities, which are important factors in determining its permeability. The dichloro groups increase the lipophilicity of the molecule, which can enhance its ability to permeate lipid membranes. However, the hydroxy group can form hydrogen bonds, potentially increasing the molecule's solubility in aqueous environments and affecting its permeability.

The methylene bridge connecting the phenyl group to the coumarin core introduces a degree of rigidity and planarity to the molecule, which can influence its interaction with the artificial membrane. The overall balance of hydrophobic and hydrophilic properties, along with the structural rigidity, will determine the permeability of the given molecule through the artificial membrane.

Based on these structural features, the given molecule is likely to exhibit moderate permeability due to the presence of both lipophilic and hydrophilic groups, as well as the rigidity introduced by the methylene bridge. This balance of properties suggests that the molecule may have a moderate ability to traverse the artificial membrane, which is a common feature in molecules with mixed hydrophobic and hydrophilic characteristics.

Final answer: Low-to-moderate permeability.

------
# 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 methylene bridge connecting it to an indolinone moiety.

The presence of the hydroxy group on the phenyl ring can enhance the molecule's ability to form hydrogen bonds, which may increase its solubility and interaction with the artificial membrane. The dichloro substituents on the phenyl ring can increase the molecule's lipophilicity, potentially enhancing its ability to permeate through the lipid-like environment of the artificial membrane.

The methylene bridge connecting the phenyl ring to the indolinone moiety introduces a degree of rigidity and planarity to the molecule, which can influence its overall shape and how it interacts with the membrane. The indolinone moiety itself is a bicyclic structure that can contribute to the molecule's overall stability and potential binding interactions with the membrane.

Overall, the combination of these structural features suggests that the given molecule may exhibit moderate permeability through the artificial membrane, balancing its hydrophilic and lipophilic properties.

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:** 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. This structural feature can influence its permeability properties.

The molecule has a quinoline moiety, which is a bicyclic aromatic compound. Quinoline structures are known for their planar and rigid nature, which can facilitate interactions with the artificial membrane, potentially enhancing permeability.

Additionally, the molecule contains a sulfonamide group linked to a phenyl ring. Sulfonamides are known for their ability to form hydrogen bonds, which can affect the molecule's solubility and permeability. The presence of this group may contribute to moderate permeability due to its polar nature, which can interact with the polar components of the artificial membrane.

Overall, the combination of the quinoline moiety and the sulfonamide group suggests that the given molecule may exhibit moderate permeability in the PAMPA assay, balancing between hydrophobic interactions from the aromatic rings and polar interactions from the sulfonamide group.

Final answer: Low-to-moderate permeability.

------
# 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:** 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 often associated with moderate to high permeability in biological membranes due to the presence of both hydrophilic and hydrophobic regions.

The molecule contains a pyridine ring, which is a heteroaromatic ring with nitrogen. This contributes to the molecule's ability to engage in hydrogen bonding and other polar interactions, enhancing its solubility and permeability in aqueous environments.

Additionally, the molecule includes a thiazole ring, another heteroaromatic ring containing both sulfur and nitrogen. This ring can also participate in hydrogen bonding and may contribute to the molecule's overall stability and permeability.

The presence of a phenyl group, which is a simple aromatic ring, adds to the hydrophobic character of the molecule. This can facilitate the passage of the molecule through lipid membranes by allowing it to interact with the hydrophobic regions of the membrane.

Overall, the combination of aromatic rings, heteroatoms, and the amide linkage in the given molecule suggests that it likely exhibits high permeability in the PAMPA assay, allowing it to effectively traverse the artificial membrane.

Final answer: High 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 phenyl-tetrazole moiety. Aromatic rings generally enhance lipophilicity, which can increase the molecule's ability to permeate through lipid membranes. However, the presence of these rings also suggests potential interactions with the artificial membrane, which is designed to mimic biological membranes.

2. **Amide Linkage**: The amide group in the molecule is a polar functional group that can form hydrogen bonds. This can enhance the molecule's solubility in aqueous environments, which is beneficial for permeability in the PAMPA assay. The amide linkage also contributes to the molecule's overall stability and rigidity, potentially affecting its ability to pass through the membrane.

3. **Sulfamoyl Group**: The sulfamoyl group attached to the phenyl ring introduces additional polarity and the potential for hydrogen bonding. This group can enhance the molecule's solubility and may also interact with the membrane, influencing permeability.

4. **Tetrazole Ring**: The tetrazole ring is a heterocyclic aromatic compound that can contribute to the molecule's overall stability and lipophilicity. Tetrazoles are often used in pharmaceuticals to mimic carboxylic acids, which can enhance binding interactions with biological targets. In the context of permeability, the tetrazole ring may facilitate passage through the membrane due to its aromatic nature.

Overall, the given molecule's combination of aromatic rings, polar functional groups, and heterocyclic components suggests that it 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 and the overall molecular conformation.

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 antimicrobial 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 due to its polar nature.

In the given molecule, the sulfonamide group is attached to a phenyl ring, which is further substituted with a methoxy group. The methoxy group can increase the lipophilicity of the molecule, potentially enhancing its ability to permeate lipid membranes.

Additionally, the molecule contains a hydroxy group attached to a phenyl ring, which can form hydrogen bonds with the artificial membrane, potentially increasing its permeability. The presence of an amino group linked to a piperazine ring can also contribute to the molecule's overall solubility and permeability, as piperazine is a common moiety in pharmaceuticals that can enhance membrane permeability.

Overall, the combination of these functional groups suggests that the given molecule may have moderate to high permeability in the PAMPA assay, as the polar sulfonamide group and the lipophilic methoxy group work together to balance solubility and membrane permeability.

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:** 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 functional 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 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. However, the overall permeability will also depend on the size and lipophilicity of the entire molecule.

The molecule also contains aromatic rings, which can contribute to its ability to interact with the membrane through π-π interactions. Additionally, the presence of a chloro substituent on one of the phenyl rings can increase the molecule's lipophilicity, potentially enhancing its permeability.

However, the hydroxyl group and the piperazine moiety introduce polar characteristics that may hinder permeability due to their ability to form hydrogen bonds with the membrane, potentially leading to a balance between hydrophilic and lipophilic properties.

Overall, the given molecule is likely to exhibit low-to-moderate permeability in the artificial membrane, as the polar and non-polar characteristics are balanced, but not strongly favoring either side.

Final answer: Low-to-moderate 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:** 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 solubility and permeability of the molecule due to its polar nature.

In the given molecule, the sulfonamide group is attached to a phenyl ring, which is further substituted with a naphthalen-1-ylamino group. The naphthalene moiety is a polycyclic aromatic hydrocarbon, which can contribute to the lipophilicity of the molecule. This lipophilic character can enhance the ability of the molecule to permeate through lipid membranes.

The presence of the thiazole ring, which is a five-membered ring containing both sulfur and nitrogen, can also influence the molecule's permeability. Thiazole rings are known for their ability to participate in hydrogen bonding and other non-covalent interactions, which can affect the molecule's interaction with the artificial membrane.

Overall, the combination of the sulfonamide group, the naphthalene moiety, and the thiazole ring suggests that the given molecule may have moderate to high permeability in the PAMPA assay, as these structural features can enhance both hydrophilic and lipophilic interactions with the membrane.

Final answer: High 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:** 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 functional 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 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. However, the overall permeability will also depend on the other structural features of the molecule.

The molecule also contains a bromo-substituted phenyl group, which can increase the lipophilicity of the molecule. This may enhance its ability to permeate the membrane, but it could also be counterbalanced by the polar nature of the sulfonamide group.

Additionally, the presence of a hydroxy group on the phenyl ring can increase the molecule's hydrophilicity, potentially improving its solubility in aqueous environments and affecting its permeability.

Overall, the given molecule is likely to have moderate permeability due to the interplay between its polar sulfonamide group and the lipophilic bromo-substituted phenyl group. However, the exact permeability would need to be determined experimentally through the PAMPA assay.

Final answer: Low-to-moderate 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 functional 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 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. However, the overall permeability will also depend on the other structural features of the molecule.

The molecule also contains a chloro-substituted phenyl group, which can increase its lipophilicity. This may enhance its ability to permeate the membrane by increasing its solubility in lipid environments. However, the presence of the hydroxy group on the phenyl ring can introduce additional hydrogen bonding capabilities, which may counteract some of the lipophilic effects.

Additionally, the molecule includes a piperidine ring, which is a common structural motif in many pharmaceuticals. Piperidine rings can increase the basicity of the molecule, potentially affecting its interaction with the membrane and its overall permeability.

Overall, the given molecule's permeability to the artificial membrane is likely to be moderate, as the sulfonamide group and other functional groups present in the structure contribute to a balance of polar and lipophilic characteristics.

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 are key 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 further influence its permeability.

Additionally, the molecule has a pyridine ring substituted with a methoxy group. The methoxy group can increase the lipophilicity of the molecule, which is generally associated with better membrane permeability. The pyridine ring itself is a basic heterocycle that can participate in π-π stacking interactions with the membrane, potentially aiding in permeation.

The molecule also features a thiophene ring, which is a sulfur-containing heterocycle. Thiophene rings are known for their electron-rich nature, which can enhance the molecule's ability to interact with the membrane through π-π interactions. The methyl substitution on the thiophene ring can further increase the lipophilicity, contributing to the overall permeability.

The chiral center in the molecule, indicated by the (1R)-configuration, suggests that the molecule has stereochemistry that could influence its interaction with the membrane, potentially affecting its permeability.

Overall, the combination of aromatic systems, heterocycles, and functional groups in the given molecule suggests that it may exhibit high permeability in the PAMPA assay due to favorable interactions with the artificial membrane.

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. The presence of nitrogen atoms in the imidazo[1,2-a]pyridine ring can also contribute to hydrogen bonding and polar interactions, potentially increasing the molecule's permeability.

2. **Pyrazole Ring**: The pyrazole moiety is another aromatic heterocycle that can contribute to the molecule's overall stability and ability to traverse the membrane. The nitrogen atoms in the pyrazole ring can participate in hydrogen bonding, which may facilitate interaction with the membrane.

3. **Benzamide Group**: The benzamide portion of the molecule introduces a polar amide linkage, which can form hydrogen bonds with the membrane. This functional group is often involved in drug-receptor interactions, and its presence can enhance the molecule's solubility and permeability.

4. **Tert-Butyl Group**: The bulky tert-butyl group attached to the benzene ring can influence the molecule's lipophilicity. While it may reduce the overall polarity of the molecule, it can also increase the steric hindrance, potentially affecting how the molecule fits into the membrane's pores. This group can also enhance the molecule's stability and resistance to metabolic degradation.

Overall, the given molecule's combination of aromatic rings, nitrogen heteroatoms, and a tert-butyl group suggests that it may have moderate to high permeability in the PAMPA assay. The aromatic and heterocyclic components can facilitate interactions with the membrane, while the tert-butyl group may enhance lipophilicity and stability.

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 ring containing both sulfur and nitrogen. This heterocyclic structure can contribute to the molecule's overall stability and ability to interact with biological systems, potentially enhancing its permeability.

Additionally, the presence of a methoxy group on the phenyl ring can increase the molecule's lipophilicity, which may improve its ability to permeate lipid membranes. The hydroxy group on the phenyl ring can also contribute to hydrogen bonding, which may further enhance the molecule's interaction 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 sulfonamide group and thiazole ring can facilitate interactions with the membrane, while the methoxy and hydroxy groups can enhance lipophilicity and hydrogen bonding, respectively.

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, often through hydrogen bonding and ionic interactions.

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 due to its aromatic nature, which can facilitate interactions with biological membranes.

Additionally, the presence of a methoxy group on the phenyl ring can influence the molecule's lipophilicity, potentially enhancing its ability to permeate lipid membranes. The hydroxy group on the phenyl ring can also contribute to hydrogen bonding, which may further aid in membrane permeability.

Overall, the combination of these functional groups suggests that the given molecule may have moderate to high permeability through the artificial membrane, as the sulfonamide and benzoxazole groups are likely to facilitate interactions with the membrane, while the methoxy and hydroxy groups may enhance its lipophilicity and hydrogen bonding capabilities.

Final answer: High permeability

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# 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 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 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 interact with biological targets, potentially enhancing its permeability.

Additionally, the presence of aromatic rings, such as the phenyl and pyridine rings, can increase the molecule's lipophilicity. This can further aid in membrane permeability by allowing the molecule to better interact with the lipid components of the membrane.

The presence of a fluorine atom on the phenyl ring can also influence the molecule's permeability. Fluorine is a small, highly electronegative atom that can enhance the molecule's metabolic stability and membrane permeability by increasing its lipophilicity and altering its electronic properties.

Overall, the combination of these functional groups and structural features suggests that the given molecule likely exhibits high permeability in the PAMPA assay, allowing it to effectively interact with the artificial membrane.

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 core 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 permeability. However, it can also introduce some degree of polarity, which may affect the overall balance between hydrophilicity and lipophilicity.

Overall, the given molecule's combination of aromatic rings, fluorine substituents, and the quinazoline core suggests that it would have 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:** 0

**Correct:** 1

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

The molecule contains a triazole ring, which is a five-membered ring containing three nitrogen atoms. This heterocyclic structure can contribute to the molecule's ability to form hydrogen bonds and engage in π-π interactions, potentially enhancing its permeability through the artificial membrane.

Additionally, the molecule has a phenyl group linked to a piperidine moiety via an ether linkage. The piperidine ring is a saturated nitrogen-containing heterocycle, which can increase the molecule's solubility and facilitate its interaction with the membrane. The ether linkage provides flexibility and can influence the overall conformation of the molecule, potentially affecting its ability to permeate the membrane.

The presence of multiple aromatic rings, including the indazole and phenyl groups, can enhance the molecule's lipophilicity, which is often associated with increased permeability. However, the balance between hydrophilic and lipophilic properties will ultimately determine the permeability of the molecule.

Overall, the combination of these structural features suggests that the given molecule may exhibit moderate permeability in the PAMPA assay, balancing between hydrophilic and lipophilic interactions with the artificial membrane.

Final answer: Low-to-moderate permeability.

------
# 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. Here's a detailed analysis of its permeability based on its structure:

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 permeability. These groups can also contribute to the molecule's solubility in aqueous environments, which is important for its interaction with the membrane.

3. **Amide Linkages**: The molecule contains multiple amide linkages, which are polar and can participate in hydrogen bonding. These linkages can influence the molecule's overall conformation and its ability to interact with the membrane. Amide bonds are generally stable and can contribute to the rigidity of the molecule, which may affect its permeability.

4. **Chirality**: The molecule has several chiral centers, which can significantly impact its three-dimensional shape and how it interacts with the artificial membrane. The specific stereochemistry of these centers can influence the molecule's binding affinity and permeability.

5. **Methylamino Group**: The presence of a methylamino group can increase the basicity of the molecule, potentially affecting its interaction with the membrane. This group can also participate in hydrogen bonding, which may enhance permeability.

Overall, the given molecule's structure suggests that it has a combination of lipophilic and polar characteristics, which can contribute to moderate permeability in the PAMPA assay. The balance of these properties will determine how effectively the molecule can traverse the artificial membrane.

Final answer: Low-to-moderate permeability.

------
# 86

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

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a member of the isoquinoline family, which is known for its aromatic and heterocyclic structure. The presence of the isoquinoline core contributes to the molecule's overall stability and potential interactions with biological membranes.

The molecule contains an amino group attached to the aromatic ring, which can enhance its solubility in water and potentially facilitate interactions with the polar head groups of the artificial membrane. This functional group can also participate in hydrogen bonding, which may influence the molecule's permeability.

Additionally, the molecule has a 2-(dimethylamino)ethyl side chain. The dimethylamino group is a basic moiety that can be protonated under physiological conditions, which may increase the molecule's solubility and enhance its ability to interact with the membrane. This group can also contribute to the molecule's overall charge, affecting its permeability through the membrane.

The benzoisoquinoline-1,3-dione structure suggests that the molecule has a planar, rigid framework, which can facilitate its passage through the membrane by allowing it to fit into the lipid bilayer more easily. However, the presence of the dione groups may also introduce some degree of polarity, which could hinder permeability by interacting with the polar head groups of the membrane.

Overall, the combination of aromaticity, basicity, and potential for hydrogen bonding suggests that the given molecule may have moderate permeability through the artificial membrane, balancing between hydrophilic and lipophilic interactions.

Final answer: Low-to-moderate 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 known for its bioactive properties. The structure of the given molecule includes a pyrazole ring, which is a five-membered heterocyclic ring containing two nitrogen atoms. This pyrazole ring is attached to a piperidine ring, a six-membered ring containing one nitrogen atom. Additionally, the molecule features a biphenyl moiety, which consists of two phenyl rings connected to each other, with one of these phenyl rings substituted with a chlorine atom.

The biphenyl structure contributes to the molecule's hydrophobic character, which can enhance its ability to interact with lipid membranes. The presence of the chlorine atom on the phenyl ring can also influence the molecule's electronic properties, potentially affecting its interaction with the artificial membrane.

The piperidine ring, being a saturated nitrogen-containing heterocycle, can increase the molecule's solubility and may also participate in hydrogen bonding interactions with the artificial membrane.

Overall, the combination of these structural features suggests that the given molecule may exhibit moderate permeability through the artificial membrane, as the hydrophobic biphenyl moiety and the polar piperidine ring can balance the molecule's interaction with the membrane. However, the exact permeability would depend on the specific conditions of the PAMPA assay, such as the nature of the artificial membrane and the solvent used.

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 a pyridopyrimidine core, which is a bicyclic structure combining pyridine and pyrimidine rings. This core is known for its planar aromatic nature, which can facilitate interactions with the artificial membrane, potentially enhancing permeability. The presence of a trifluoromethyl group on the pyridopyrimidine ring can increase the lipophilicity of the molecule, which often correlates with higher membrane permeability due to increased hydrophobic interactions with the lipid components of the membrane.

Additionally, the molecule features a piperazine ring, which is a common motif in pharmaceuticals that can enhance solubility and permeability. The piperazine ring can also participate in hydrogen bonding and ionic interactions, which may aid in the molecule's passage through the membrane.

The phenyl ring attached to the piperazine is substituted with a methoxy group, which can further increase lipophilicity and potentially improve membrane permeability. The methoxy group can also participate in hydrogen bonding, which may assist in the molecule's interaction with the membrane.

Overall, the combination of aromatic rings, lipophilic substituents, and functional groups capable of hydrogen bonding suggests that the given molecule likely exhibits high permeability in the PAMPA assay.

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:** 0

**Correct:** 1

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

The presence of the trifluoromethyl group attached to the phenyl ring is a key feature. This group is known to enhance the lipophilicity of the molecule, which can increase its ability to permeate lipid membranes. The trifluoromethyl group is highly electronegative, which can also influence the molecule's interaction with the artificial membrane by affecting its electronic distribution.

The thiazole ring in the molecule contributes to its heterocyclic nature, which can impact the molecule's overall stability and reactivity. Thiazole rings are often involved in hydrogen bonding and π-π interactions, which can affect the molecule's binding affinity to the membrane.

Additionally, the presence of the imidazole ring introduces another heterocyclic component, which is known for its ability to participate in hydrogen bonding and coordination with metal ions. This can further influence the molecule's interaction with the membrane.

The carboxamide group in the molecule is a polar functional group that can form hydrogen bonds with the membrane, potentially enhancing its permeability. However, this group can also introduce some degree of polarity, which might limit the overall permeability depending on the balance with the other hydrophobic components.

Overall, the combination of these functional groups suggests that the given molecule likely exhibits a balance of hydrophobic and hydrophilic properties, which can result in moderate permeability through the artificial membrane. The trifluoromethyl group and aromatic rings contribute to its lipophilicity, while the heterocyclic rings and carboxamide group provide opportunities for specific interactions with the membrane.

Final answer: Low-to-moderate 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:** 1

**Correct:** 1

# 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 several structural features.

1. **Aromaticity and Hydrophobicity**: The presence of aromatic rings, such as the phenyl and acetylphenyl groups, contributes to the hydrophobic character of the molecule. This hydrophobicity can enhance the molecule's ability to permeate through the lipid-like environment of the artificial membrane, suggesting high permeability.

2. **Sulfonamide Group**: The sulfonamide moiety is known for its ability to form hydrogen bonds, which can facilitate interactions with the membrane. This group can also contribute to the molecule's solubility and permeability, potentially enhancing its ability to permeate the membrane.

3. **Methoxy and Methyl Groups**: The methoxy group on the pyrrole ring and the methyl group on the pyrrole and phenyl rings increase the lipophilicity of the molecule. These groups can enhance the molecule's ability to traverse the lipid bilayer of the artificial membrane, further suggesting high permeability.

4. **Pyrrole Ring**: The pyrrole ring is a heterocyclic aromatic compound that can contribute to the overall stability and planarity of the molecule. This structural feature can facilitate the passage of the molecule through the membrane by allowing it to maintain a planar conformation, which is favorable for permeation.

Overall, the combination of aromaticity, hydrophobicity, 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

------
# 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 to understand its permeability characteristics.

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 electron-withdrawing properties due to the electronegativity of the fluorine atoms. This can increase the molecule's lipophilicity, enhancing its ability to permeate through 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 also participate in hydrogen bonding. This feature can affect the molecule's overall polarity and solubility, which in turn influences its permeability.

5. **Pyrimidine Ring**: The pyrimidine ring is a heterocyclic aromatic compound that can contribute to the molecule's overall stability and rigidity. This structural feature can affect how the molecule fits into the membrane and its overall permeability.

Overall, the given molecule's combination of aromatic rings, electron-withdrawing groups, and polar functional groups suggests that it has a balance of hydrophobic and hydrophilic properties. This balance is likely to result in moderate permeability through the artificial membrane, as the molecule can interact with both hydrophobic and hydrophilic components of the membrane. Therefore, the permeability of the given molecule in the PAMPA assay is likely to be classified as low-to-moderate.

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:** 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 to understand its permeability characteristics.

1. **Aromatic Amide Structure**: 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. **Dimethylpyrrole Moiety**: The dimethylpyrrole component contributes to the molecule's hydrophobic character. Pyrrole rings are relatively small and can provide some flexibility to the molecule, potentially allowing it to fit into the membrane's structure more easily.

3. **Acetyl Group**: The acetyl group attached to the pyrrole ring introduces a polar character, which can enhance the molecule's ability to interact with the polar head groups of the artificial membrane. This group can also participate in hydrogen bonding, which may aid in membrane permeation.

4. **Bromophenyl Group**: The bromophenyl group adds to the hydrophobicity and may also contribute to the molecule's ability to penetrate the membrane. The presence of a bromine atom can increase the molecule's overall size and may affect its ability to fit into the membrane's pores.

5. **Dimethylaminoethoxy Group**: This group introduces a basic nitrogen atom, which can be protonated under physiological conditions, potentially enhancing the molecule's solubility in aqueous environments. This group can also participate in hydrogen bonding and ionic interactions, which may facilitate membrane permeation.

6. **Sulfamoyl Group**: The sulfamoyl group is a polar and potentially ionizable group, which can enhance the molecule's solubility in water and its ability to interact with the polar head groups of the artificial membrane. This group can also form hydrogen bonds, which may aid in membrane permeation.

Overall, the given molecule contains a combination of hydrophobic and hydrophilic groups, which suggests that it may have moderate permeability in the PAMPA assay. The aromatic amide and pyrrole moieties contribute to its ability to interact with the membrane, while the various polar and ionizable groups enhance its solubility and interaction with the membrane. However, the balance of these features will ultimately determine its permeability, and the presence of both hydrophobic and hydrophilic groups suggests that it may have a moderate permeability profile.

Final answer: Low-to-moderate 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:** 1

**Correct:** 0

# Response:
The given molecule is designed to interact with the extracellular signal-regulated kinase 2 (ERK2) enzyme, which is part of the mitogen-activated protein kinase (MAPK) pathway. This pathway is crucial in cellular processes such as cell division, differentiation, and secretion. The molecule's ability to permeate the artificial membrane is essential for its potential effectiveness as a therapeutic agent.

The structure of the given molecule includes a pyridine ring system, which is known for its ability to enhance the molecule's solubility and permeability. The presence of the amino group on the pyridine ring can increase the molecule's polarity, potentially improving its interaction with the polar environment of the artificial membrane.

Additionally, the molecule contains a carboxylic acid group, which can form hydrogen bonds and ionic interactions with the membrane, potentially facilitating its passage. The cyclopropylamino group introduces a small, non-polar moiety that may help the molecule to navigate through the lipid-rich environment of the membrane.

Overall, the combination of these functional groups suggests that the given molecule has the potential for high permeability through the artificial membrane, which is a critical factor for its activity as a kinase inhibitor.

Final answer: High 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 small molecule inhibitor targeting the mTOR pathway, specifically the mTORC1 component. The permeability of the molecule through the artificial membrane is influenced by its structural features, which include a combination of hydrophobic and hydrophilic elements.

The molecule contains a cyclohexyl group, which is a saturated hydrocarbon ring. This contributes to the hydrophobic character of the molecule, enhancing its ability to traverse lipid membranes. The presence of a phenyl group, which is an aromatic ring, also adds to the hydrophobicity and can facilitate interactions with the lipid bilayer of the artificial membrane.

Additionally, the molecule features a pyrano[2,3-d]pyrimidin-4-amine moiety, which introduces a heterocyclic structure with nitrogen atoms. This part of the molecule can engage in hydrogen bonding and other polar interactions, which may influence its solubility and permeability. The carboxylic acid group at the end of the molecule is a hydrophilic functional group that can enhance solubility in aqueous environments and may also participate in ionic interactions with the membrane.

Overall, the balance of hydrophobic and hydrophilic components in the given molecule suggests that it would exhibit moderate permeability through the artificial membrane, as it possesses both lipophilic and polar characteristics that facilitate membrane interaction.

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 structure. This contributes to the molecule's ability to interact with biological membranes, potentially enhancing its permeability.

The presence of a hydroxy group on the quinoline ring can increase the molecule's polarity, which may improve its solubility in aqueous environments and facilitate interactions with the polar head groups of the artificial membrane. This can enhance permeability by allowing the molecule to better orient and insert itself into the membrane.

The carboxamide group is another polar functional group that can form hydrogen bonds with the membrane, potentially increasing the molecule's affinity for the membrane and its permeability.

The N-substituent, which includes a phenyl group and a butyl chain, introduces a hydrophobic character to the molecule. This hydrophobic region can interact with the lipid bilayer of the artificial membrane, promoting insertion and permeation through the membrane.

Overall, the combination of aromatic, polar, and hydrophobic features in the given molecule suggests that it may have a balance of interactions that favor 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 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. **Imidazo[1,2-a]pyridine Core**: This bicyclic structure is a heteroaromatic system that contributes to the molecule's rigidity and planarity. Such aromatic systems can enhance lipophilicity, which often correlates with increased membrane permeability. However, the presence of nitrogen atoms in the ring can also introduce hydrogen bonding capabilities, which may affect permeability depending on the environment.

2. **Methylsulfonylphenyl Group**: The methylsulfonyl group is a polar moiety that can increase the molecule's overall polarity. This group can enhance solubility in aqueous environments, which is beneficial for permeability in PAMPA, as it involves a polar artificial membrane. The presence of the phenyl ring can also contribute to lipophilicity, balancing the polar effects of the sulfonyl group.

3. **Acetamido Group**: This group introduces additional hydrogen bonding potential due to the amide linkage. It can interact with the polar environment of the PAMPA membrane, potentially enhancing permeability through hydrogen bonding interactions.

4. **Methyl Ester**: The ester group is a common feature in many drug molecules and can influence permeability by increasing lipophilicity. However, esters can also be susceptible to hydrolysis, which might affect the stability of the molecule in the PAMPA assay.

Overall, the given molecule has a balance of lipophilic and polar features. The imidazo[1,2-a]pyridine core and phenyl ring contribute to lipophilicity, while the methylsulfonyl, acetamido, and methyl ester groups introduce polar characteristics. These features suggest that the molecule would have moderate permeability in the PAMPA assay, as it can interact with both the polar and non-polar components of the artificial membrane.

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:** 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 potential impact on permeability:

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 can facilitate π-π stacking interactions with the membrane, potentially increasing permeability.

2. **Morpholine Ring**: The presence of a morpholine ring introduces a polar, heterocyclic component to the molecule. This can enhance solubility in aqueous environments, which is beneficial for permeability. The morpholine ring can also participate in hydrogen bonding, which may aid in membrane interaction.

3. **Methanesulfonamide Group**: This functional group is polar and can form hydrogen bonds, which may enhance the molecule's solubility and interaction with the membrane. The sulfonamide group is often involved in ionic interactions, which can be crucial for permeability.

4. **Phenyl Ring**: The phenyl ring contributes to the overall hydrophobic character of the molecule. While it can enhance membrane permeability through hydrophobic interactions, its presence may also hinder permeability due to steric effects and limited aqueous solubility.

5. **Methanone Linkage**: The carbonyl group in the methanone linkage can participate in hydrogen bonding, which may aid in membrane interaction. However, it can also introduce some degree of polarity, which might affect the overall balance between hydrophilicity and lipophilicity.

Overall, the given molecule has a combination of hydrophobic and hydrophilic features, which suggests that it may exhibit moderate permeability in the PAMPA assay. The aromatic and polar components can facilitate interactions with the membrane, while the sulfonamide and morpholine groups can enhance solubility and binding affinity. However, the balance of these features will ultimately determine the molecule's permeability profile.

Final answer: Low-to-moderate 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 the key structural elements and their impact on permeability:

1. **Fluorophenyl Group**: The presence of a fluorophenyl group contributes to the molecule's lipophilicity, which can enhance its ability to permeate lipid membranes. The fluorine atom can also increase the molecule's stability and binding affinity to certain biological targets.

2. **Pyrazolopyrimidine Core**: This bicyclic structure is a common motif in many pharmaceuticals, known for its ability to interact with various biological targets. The rigidity and planarity of this core can facilitate passage through the artificial membrane by allowing the molecule to maintain a consistent orientation.

3. **Aminoethyl Linker**: The aminoethyl group provides a flexible linkage that can help the molecule adapt to the membrane's structure, potentially enhancing permeability. The presence of an amine group can also contribute to hydrogen bonding, which may aid in interaction with the membrane.

4. **Phosphate Group**: The dihydrogen phosphate moiety is hydrophilic and can enhance the molecule's solubility in aqueous environments. However, its presence may also hinder permeability due to its polar nature, which can limit the molecule's ability to cross lipid-rich membranes.

5. **Methoxypropoxy Linker**: This ether linkage provides additional flexibility and can influence the molecule's overall conformation. It may help the molecule to orient itself in a way that optimizes permeability through the membrane.

Overall, the given molecule has a balance of lipophilic and hydrophilic components, which suggests that it may exhibit moderate permeability in the PAMPA assay. The presence of the fluorophenyl group and pyrazolopyrimidine core likely contribute to its ability to permeate the membrane, while the phosphate group may limit its passage to some extent. Therefore, the molecule is likely to have a low-to-moderate permeability in the PAMPA assay.

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:** 1

**Correct:** 1

# 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 fused ring system consisting of a benzene ring and a pyranone ring. The presence of this core structure often contributes to the molecule's ability to interact with biological membranes, potentially enhancing its permeability.

Additionally, the molecule contains an aminophenyl group attached to the chromone core. The amino group is a polar functional group that can form hydrogen bonds, which may increase the molecule's solubility in aqueous environments and potentially facilitate its passage through the artificial membrane.

The morpholine ring, another key feature of the molecule, is a heterocyclic amine that can also contribute to 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 dipole interactions.

Overall, the combination of the chromone core, aminophenyl group, and morpholine ring suggests that the given molecule may exhibit moderate to high permeability in the PAMPA assay, as these structural features can facilitate interactions with the artificial membrane.

Final answer: High permeability.

------
# 100

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

**Label:** 1

**Predi:** 0

**Correct:** 0

# 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 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 may enhance the molecule's solubility in aqueous environments and facilitate its interaction with the membrane.

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 ability to interact with the membrane.

Additionally, there is a phenyl ring substituted with a chlorine atom and a cyclohexyl group. The chlorine atom is electronegative and can influence the molecule's lipophilicity, while the cyclohexyl group is a non-polar, hydrophobic moiety that can enhance the molecule's ability to penetrate lipid membranes.

Overall, the combination of these functional groups suggests that the given molecule may have moderate permeability in the PAMPA assay. The presence of polar groups like the carboxylic acid and methoxy group, along with the hydrophobic cyclohexyl group, indicates a balance between hydrophilic and lipophilic properties, which is typical for molecules with moderate permeability.

Final answer: Low-to-moderate 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 degree of rigidity and planarity, 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 provides a hydrophobic character to the molecule. This hydrophobicity can enhance the molecule's ability to permeate lipid membranes, as it can interact with the hydrophobic regions of the artificial membrane.

3. **Ethoxy and Morpholine Groups**: The ethoxy group introduces some degree of polarity, which can improve solubility in aqueous environments. The morpholine group, being a heterocyclic amine, can also contribute to the molecule's solubility and may participate in hydrogen bonding with the membrane.

4. **Pyridine and Piperidine Rings**: These nitrogen-containing heterocycles can enhance the molecule's ability to interact with the membrane through hydrogen bonding and dipole interactions. The pyridine ring, in particular, can engage in π-π interactions due to its aromatic nature.

5. **Ethyl and Methyl Groups**: These alkyl groups contribute to the overall hydrophobicity of the molecule, which can aid in permeability by enhancing interactions with the lipid components of the artificial membrane.

6. **Carboxamide Linkage**: The carboxamide linkage is a polar functional group that can form hydrogen bonds with the membrane, potentially increasing the molecule's affinity for the membrane.

Overall, the given molecule exhibits a balance of hydrophobic and hydrophilic properties, with multiple functional groups that can interact with the artificial membrane. These interactions suggest that the molecule would have moderate to high permeability in the PAMPA assay, as it can effectively traverse the membrane while maintaining sufficient interaction with the membrane components.

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 includes 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 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 carboxylic acid group attached to the pyridine ring. Carboxylic acid groups are polar and can form hydrogen bonds with the membrane, potentially increasing the molecule's solubility and permeability.

The imidazole ring in the molecule is another aromatic heterocycle that can engage in hydrogen bonding and π-π interactions, similar to the pyridine ring. Imidazole rings are often found in biologically active compounds and can enhance the molecule's ability to permeate biological membranes.

The methoxyphenyl group is an aromatic ring with a methoxy substituent, which can increase the lipophilicity of the molecule. This lipophilic character can enhance the molecule's ability to permeate lipid membranes, such as the artificial membrane used in the PAMPA assay.

Overall, the combination of these functional groups and aromatic systems suggests that the given molecule is likely to have high permeability in the artificial membrane, as it possesses both polar and non-polar characteristics that facilitate interaction with the membrane.

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 the key components 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, suggesting a potential for moderate to 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 and permeability. The presence of this group suggests that the given molecule may have moderate to high permeability due to its ability to interact with the membrane.

3. **Methoxy Linkage**: The methoxy group acts as a linker between the pyrazole ring and the phenyl ring. This ether linkage can increase the molecule's lipophilicity, which may enhance its ability to traverse the lipid components of the artificial membrane. The presence of this linkage suggests a moderate permeability, as it can balance the polar and non-polar characteristics of the molecule.

4. **Chlorophenyl Group**: The chlorophenyl group, with its chlorine substituent, adds to the lipophilic character of the molecule. The chlorine atom can also participate in halogen bonding, which may further influence the molecule's interaction with the membrane. This group can contribute to the overall permeability by enhancing the molecule's ability to penetrate the lipid bilayer of the artificial membrane.

Overall, the given molecule's structural features, including the pyrazole ring, carboxylic acid group, methoxy linkage, and chlorophenyl group, suggest that it has moderate to high permeability in the PAMPA assay. These features collectively enhance the molecule's ability to interact with the artificial membrane, facilitating its permeation.

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 potential impact on permeability:

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 facilitate interactions with the lipid bilayer of the artificial membrane, potentially increasing 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 within 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 participate in hydrogen bonding. This group can enhance the molecule's solubility in aqueous environments, which is crucial for its interaction with the PAMPA membrane. However, it may also introduce some steric hindrance, potentially reducing permeability.

Overall, the given molecule's structure suggests a balance between hydrophobic and hydrophilic properties. The indole and phenyl groups contribute to hydrophobic interactions, while the pyrrolidinone and carboxamide groups introduce polar characteristics. These features collectively suggest that the given molecule likely exhibits high permeability in the PAMPA assay, as it can effectively interact with the artificial membrane.

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 fluorophenyl group, a pyrazolopyridine moiety, and a benzamide group. Aromatic rings generally contribute to lipophilicity, which can enhance the molecule's ability to permeate through lipid membranes. However, the presence of a fluorine atom on the phenyl ring can increase the molecule's polarity, potentially affecting its permeability.

2. **Fluorine Substitution**: The fluorine atom on the phenyl ring can influence the electronic properties of the molecule, potentially affecting its interaction with the artificial membrane. Fluorine is highly electronegative, which can increase the molecule's polarity and potentially reduce its permeability by making it more hydrophilic.

3. **Amide Linkage**: The benzamide group introduces an amide linkage, which is polar and can form hydrogen bonds. This can enhance the molecule's solubility in aqueous environments, but it may also hinder permeability through the lipid-rich artificial membrane due to the polar nature of the amide bond.

4. **Methoxyethyl Group**: The presence of a methoxyethyl group contributes to the molecule's overall polarity and solubility. This group can enhance the molecule's ability to interact with the aqueous environment of the PAMPA assay, but it may also reduce permeability through the lipid membrane due to its polar nature.

Overall, the given molecule has a balance of lipophilic aromatic rings and polar functional groups. While the aromatic rings may promote permeability through the lipid membrane, the polar groups, such as the fluorophenyl, amide, and methoxyethyl groups, may reduce it. Therefore, the molecule is likely to exhibit low-to-moderate permeability in the PAMPA assay.

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 aromatic rings, which contribute to its permeability characteristics in the PAMPA assay. 

The presence of the methoxy group on the phenyl ring can enhance the molecule's lipophilicity, which generally increases permeability through lipid membranes. The phenyl ring itself is a hydrophobic aromatic system that can also contribute to the molecule's ability to interact with the hydrophobic environment of the artificial membrane.

The pyridopyridine core is a bicyclic aromatic system that can provide additional stability and rigidity to the molecule, potentially facilitating its passage through the membrane by allowing it to fit into specific binding sites or channels. The aromatic nature of this core can also enhance interactions with the membrane through π-π stacking or other non-covalent interactions.

The piperazine ring, particularly with the methyl substitution, introduces a basic nitrogen atom that can participate in hydrogen bonding or ionic interactions with the membrane. This can influence the molecule's solubility and permeability, potentially enhancing its ability to traverse the membrane.

The carboxamide group is a polar functional group that can form hydrogen bonds with the membrane, which may aid in the molecule's permeability by providing additional interaction points. However, it can also introduce some degree of polarity, which might limit permeability depending on the balance with the other hydrophobic components.

Overall, the given molecule's combination of aromatic systems, lipophilic groups, and polar functional groups suggests that it 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.

------
# 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 potential 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. The presence of nitrogen atoms in the heterocyclic rings can also contribute to hydrogen bonding, potentially increasing the molecule's affinity for the membrane.

2. **Pyridine Ring**: The pyridine moiety is another aromatic ring that can participate in π-π interactions and hydrogen bonding. The electron-withdrawing nature of the pyridine nitrogen can also influence the electronic distribution of the molecule, potentially affecting its interaction with the membrane.

3. **Phenyl Group**: The phenyl group attached to the imidazo[1,2-a]pyridine core adds hydrophobic character to the molecule. This can enhance the molecule's ability to penetrate lipid membranes, as it can interact with the hydrophobic regions of the artificial membrane.

4. **Dimethylaminoethyl Side Chain**: This functional group introduces a basic nitrogen atom, which can be protonated under physiological conditions. This protonation can increase the molecule's solubility in aqueous environments, facilitating its interaction with the membrane. Additionally, the dimethylamino group can form ionic interactions with the membrane, potentially enhancing permeability.

5. **Carboxamide Group**: The carboxamide group can form hydrogen bonds with the artificial membrane, which may aid in the molecule's interaction and permeation. The presence of this group can also influence the overall polarity of the molecule, affecting its solubility and permeability.

Overall, the given molecule exhibits a combination of hydrophobic and hydrophilic properties, along with aromatic and basic characteristics. These features suggest that the molecule can effectively interact with the artificial membrane, likely resulting in high permeability.

Final answer: High permeability

------
# 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 to understand its permeability:

1. **Pyrrolopyridine Core**: The presence of a pyrrolopyridine core in the given molecule suggests a planar, aromatic structure. This core can enhance the molecule's ability to interact with the artificial membrane through π-π stacking interactions, which are common in aromatic systems. Such interactions can facilitate the passage of the molecule through the membrane.

2. **Carboxylic Acid Group**: The carboxylic acid group is a polar functional group that can form hydrogen bonds with the artificial membrane. This can increase the molecule's solubility in the membrane environment and enhance its permeability. However, the presence of this group can also introduce some degree of polarity, which might limit its permeability if the membrane is highly lipophilic.

3. **Chlorophenyl Group**: The chlorophenyl group adds 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.

4. **Methoxyethyl Linker**: The methoxyethyl linker provides flexibility and a degree of hydrophilicity to the molecule. This linker can help the molecule to adapt its conformation to fit into the membrane, potentially enhancing its permeability.

5. **Pyrrolidine Ring**: The pyrrolidine ring contributes to the molecule's overall rigidity and can affect its ability to fit into the membrane. The presence of this ring can also influence the molecule's pharmacokinetic properties, such as absorption and distribution.

Overall, the given molecule has a combination of aromatic, polar, and lipophilic features that suggest it may have moderate to high permeability in the PAMPA assay. The balance of hydrophilic and lipophilic groups, along with the structural rigidity and flexibility provided by the various functional groups, likely allows the molecule to interact effectively with the artificial membrane, facilitating its passage.

Final answer: High permeability

------
# 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 with several distinct structural features that influence its permeability in the PAMPA assay. 

Firstly, the presence of the spirocyclic structure, specifically the spiro[5.5]undecane, contributes to the rigidity and three-dimensional shape of the molecule. This rigidity can affect how the molecule interacts with the artificial membrane, potentially enhancing its ability to fit into specific binding sites or pass through the membrane.

Secondly, the molecule contains an isoquinoline moiety, which is a bicyclic aromatic structure. Aromatic rings can participate in π-π interactions with the membrane, which may facilitate permeation. However, the presence of the isoquinoline also introduces some degree of hydrophobicity, which can hinder permeability if the membrane is more hydrophilic.

Additionally, the molecule has a pyrazole ring with a ketone group. The pyrazole ring is a five-membered heterocycle containing nitrogen atoms, which can contribute to hydrogen bonding interactions with the membrane. The ketone group can also participate in hydrogen bonding, potentially enhancing the molecule's interaction with the membrane.

The isopropyl groups attached to the pyrazole and isoquinoline rings increase the hydrophobic character of the molecule, which may enhance its ability to permeate lipid membranes. However, these groups can also increase steric hindrance, potentially limiting the molecule's ability to pass through the membrane.

Overall, the given molecule's structural features suggest a balance between hydrophobic and hydrophilic interactions, as well as rigidity and flexibility. These factors collectively influence its permeability in the PAMPA assay, likely resulting in moderate permeability.

Final answer: Low-to-moderate permeability.

------
# 110

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

**Label:** 1

**Predi:** 0

**Correct:** 0

# 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 presence of the amino group on the thienopyridine core can enhance the molecule's ability to form hydrogen bonds, which may increase its solubility and permeability. The phenyl group attached to the thienopyridine core contributes to the molecule's hydrophobic character, which can facilitate its interaction with lipid membranes.

The overall structure of the given molecule suggests that it may have moderate permeability in the PAMPA assay. The balance between hydrophilic and hydrophobic properties, along with the potential for hydrogen bonding, indicates that the molecule can traverse the artificial membrane, but may not be highly permeable due to the presence of the bulky phenyl group and the relatively complex fused ring system.

Final answer: Low-to-moderate permeability.

------
# 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 with several functional groups and structural features that influence its permeability in the PAMPA assay. Let's break down these features to understand its 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. The presence of nitrogen atoms in the heterocyclic rings can also contribute to hydrogen bonding, which may facilitate membrane interaction.

2. **Morpholinyl Group**: The morpholine ring is a six-membered heterocycle containing both oxygen and nitrogen. This group is polar and can form hydrogen bonds, which may enhance the molecule's solubility in aqueous environments and its interaction with the polar head groups of the artificial membrane.

3. **Benzamide Moiety**: The benzamide group contains an amide linkage, which is polar and can participate in hydrogen bonding. This group can also interact with the membrane through dipole-dipole interactions, potentially increasing permeability.

4. **Hydroxyethyl Linkage**: The hydroxyethyl group introduces an additional polar site, which can enhance solubility and facilitate hydrogen bonding with the membrane.

Overall, the given molecule has multiple polar functional groups and aromatic systems that can interact with the artificial membrane. These features suggest that the molecule is likely to have high permeability in the PAMPA assay, as it can effectively interact with the membrane through various non-covalent interactions.

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 includes several functional groups and structural features that influence its permeability in the PAMPA assay. Let's break down these features to understand its permeability:

1. **Indazole Core**: The presence of the indazole moiety, 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 Substitution**: The bromine atom attached to the indazole ring can influence the molecule's electronic properties and lipophilicity. Bromine is a relatively large and electronegative atom, which can increase the molecule's overall lipophilicity. This can enhance the molecule's ability to traverse lipid membranes, suggesting higher permeability.

3. **Pyrrolidine-2-carboxamide Moiety**: The pyrrolidine ring is a five-membered nitrogen-containing heterocycle that can contribute to the molecule's flexibility and solubility. The carboxamide group is polar and can form hydrogen bonds, which may facilitate interactions with the membrane and improve solubility in aqueous environments, potentially enhancing permeability.

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 due to its polar nature. The presence of the morpholine ring can also enhance the molecule's ability to interact with the membrane through hydrogen bonding and dipole interactions, which may improve permeability.

Overall, the given molecule's combination of aromatic, heterocyclic, and polar functional groups suggests that it has a balance of hydrophobic and hydrophilic properties. This balance can facilitate its interaction with the artificial membrane, likely resulting in high permeability.

Final answer: High permeability

------
# 113

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

**Label:** 1

**Predi:** 0

**Correct:** 0

# 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 in the given molecule suggests a potential for moderate permeability. Quinazolines are known for their planar aromatic structure, which can facilitate interactions with the artificial membrane. However, the presence of nitrogen atoms in the quinazoline ring can also introduce hydrogen bonding capabilities, which may enhance its interaction with the membrane.

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 can allow the molecule to better fit into the membrane's structure, potentially enhancing its permeability. The nitrogen atom in this moiety can also participate in hydrogen bonding, further influencing its interaction with the membrane.

3. **Amide Linkage**: The amide group in the given molecule is a common feature in many bioactive compounds. Amides can form hydrogen bonds with the membrane, which can stabilize the interaction and potentially increase permeability. However, the presence of the amide linkage also introduces some rigidity to the molecule, which might limit its conformational flexibility.

4. **Methyl Substitution**: The methyl group attached to the tetrahydroquinoline ring can increase the lipophilicity of the molecule. Increased lipophilicity generally enhances membrane permeability, as it allows the molecule to better interact with the lipid components of the membrane.

Overall, the given molecule's structure suggests a balance of features that could result in moderate to high permeability in the PAMPA assay. The aromatic quinazoline core, combined with the flexible tetrahydroquinoline moiety and the lipophilic methyl group, likely contribute to its ability to traverse the artificial membrane. However, the specific permeability would ultimately depend on the exact nature of the interactions between the molecule and the membrane in the assay conditions.

Final answer: Low-to-moderate permeability.

------
# 114

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

**Label:** 1

**Predi:** 0

**Correct:** 0

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

1. **Piperidine Ring**: The presence of a piperidine ring, a six-membered nitrogen-containing heterocycle, is a common feature in many bioactive compounds. Piperidine rings are known for their ability to enhance the lipophilicity of molecules, which can improve membrane permeability. This is because the nitrogen atom can participate in hydrogen bonding, which may facilitate interaction with the membrane.

2. **Chlorophenyl Group**: The chlorophenyl group is a phenyl ring substituted with a chlorine atom. The presence of a chlorine atom can increase the lipophilicity of the molecule, which can enhance its ability to permeate lipid membranes. Additionally, the aromatic nature of the phenyl ring can contribute to π-π interactions with the membrane, potentially aiding in permeation.

3. **Pyrazole Ring**: The pyrazole ring is a five-membered heterocycle containing two nitrogen atoms. This ring can contribute to the molecule's overall stability and may also participate in hydrogen bonding. The presence of the pyrazole ring can influence the molecule's electronic properties, which may affect its interaction with the membrane.

4. **Benzamide Moiety**: The benzamide group consists of a benzene ring attached to an amide linkage. Amides are polar functional groups that can form hydrogen bonds, which may enhance the molecule's solubility in aqueous environments. However, the benzamide moiety can also contribute to the overall hydrophilicity of the molecule, potentially reducing its permeability through lipid membranes.

Overall, the given molecule contains both lipophilic and hydrophilic components. The lipophilic chlorophenyl and piperidine rings suggest that the molecule may have high permeability due to its ability to interact with lipid membranes. However, the polar benzamide group may counterbalance this by increasing solubility in aqueous environments, which could result in a more moderate permeability profile. Therefore, the given molecule is likely to exhibit low-to-moderate permeability in the PAMPA assay.

Final answer: Low-to-moderate permeability.

------
# 115

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

**Label:** 0

**Predi:** 0

**Correct:** 1

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

1. **Heterocyclic Rings**: The molecule contains multiple heterocyclic rings, including a pyrazolo[1,5-a]pyrimidine and a pyridine ring. These nitrogen-containing rings can enhance the molecule's ability to form hydrogen bonds and engage in polar interactions with the artificial membrane. This can increase its permeability by facilitating passage through the membrane.

2. **Aromaticity**: The presence of aromatic rings, such as the pyridine and phenyl groups, contributes to the molecule's lipophilicity. Aromatic rings can interact with the hydrophobic regions of the artificial membrane, potentially enhancing permeability by allowing the molecule to embed within the membrane.

3. **Carbonyl Group**: The carbonyl group in the pyridine-2-carbonyl moiety can participate in hydrogen bonding with the membrane, which may aid in permeability. However, it can also introduce some polarity, which might limit permeability depending on the balance with other hydrophobic features.

4. **Overall Structure**: The combination of aromatic and heterocyclic rings, along with the carbonyl group, suggests that the given molecule has a balance of hydrophobic and polar characteristics. This balance is often associated with moderate permeability in PAMPA assays, as the molecule can interact with both hydrophobic and hydrophilic components of the membrane.

Based on these structural features, the given molecule is likely to exhibit low-to-moderate permeability in the PAMPA assay. This is due to the interplay between its aromatic and heterocyclic components, which provide a balance of lipophilicity and polar interactions with the artificial membrane.

Final answer: Low-to-moderate permeability.

------
# 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. **Pyrido[2,3-d]pyrimidin-7-one Core**: This bicyclic structure is a fused ring system that contributes to the rigidity and planarity of the molecule. Such structures can enhance the molecule's ability to interact with biological membranes, potentially increasing its permeability. However, the presence of nitrogen atoms in the rings can also introduce polar characteristics, which may affect solubility and permeability.

2. **Morpholine Ring**: The morpholine ring is a six-membered heterocycle containing both oxygen and nitrogen. This ring can increase the molecule's hydrophilicity, which may enhance its solubility in aqueous environments. The presence of this ring can also facilitate hydrogen bonding with the artificial membrane, potentially improving permeability.

3. **Substituted Phenyl Group**: The phenyl group is substituted with a chloro and a fluoro group. These halogen substituents can increase the lipophilicity of the molecule, which may enhance its ability to permeate lipid membranes. However, the electron-withdrawing nature of these groups can also affect the electronic distribution within the molecule, potentially influencing its interaction with the membrane.

4. **Methyl Linkage**: The methyl group connecting the phenyl group to the pyrido[2,3-d]pyrimidin-7-one core provides a degree of flexibility, which can allow the molecule to adapt its conformation when interacting with the membrane. This flexibility can be beneficial for permeability, as it may enable the molecule to fit into the membrane more effectively.

Overall, the given molecule's structure suggests a balance between hydrophilic and lipophilic properties, 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 balance of these interactions will determine its exact permeability. Therefore, the given molecule is likely to exhibit low-to-moderate permeability in the PAMPA assay.

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:** 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 components and their potential impact on permeability:

1. **Pyrimidopyrimidine Core**: The presence of a pyrimidopyrimidine core suggests that the molecule has a relatively planar and rigid structure. This rigidity can enhance the molecule's ability to interact with the artificial membrane, potentially increasing its permeability. The core also contains nitrogen atoms, which can participate in hydrogen bonding, potentially aiding in membrane interaction.

2. **Morpholine Ring**: The morpholine ring is a heterocyclic amine that can increase the molecule's solubility in water due to its polar nature. This solubility is beneficial for permeability as it allows the molecule to dissolve in the aqueous environment of the PAMPA assay, facilitating its passage through the membrane.

3. **Difluorophenyl Group**: The difluorophenyl group introduces both hydrophobic and electronic effects. The fluorine atoms can enhance the molecule's lipophilicity, which may improve its ability to traverse lipid membranes. However, the presence of the fluorine atoms can also create steric hindrance, potentially affecting the molecule's overall conformation and permeability.

4. **Chloro Substituent**: The chloro substituent on the phenyl ring can further influence the molecule's lipophilicity and electronic properties. Chlorine is a relatively large atom that can affect the molecule's shape and its ability to interact with the membrane.

Overall, the given molecule's structure suggests a balance between hydrophilic and lipophilic properties, which is typical for molecules with moderate permeability in PAMPA assays. The presence of polar groups like the morpholine ring and the pyrimidopyrimidine core, combined with the lipophilic difluorophenyl group, suggests that the molecule may have moderate permeability, allowing it to interact with the artificial membrane while still being soluble in the assay environment.

Final answer: Low-to-moderate permeability.

------
# 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 potential impact on permeability:

1. **Triazole Ring**: The presence of a triazole ring is significant in drug design due to its stability and ability to participate in hydrogen bonding. This heterocyclic ring can enhance the molecule's ability to interact with biological membranes, potentially increasing its permeability.

2. **Piperidine Ring**: The piperidine moiety is a six-membered nitrogen-containing ring that is commonly found in pharmaceuticals. It is known for its basicity and ability to form hydrogen bonds, which can facilitate the molecule's interaction with the artificial membrane, possibly enhancing permeability.

3. **Methoxy Groups**: The methoxy groups attached to the phenyl rings contribute to the molecule's lipophilicity. Increased lipophilicity can enhance the ability of the molecule to traverse lipid membranes, suggesting higher permeability.

4. **Benzoyl Group**: The benzoyl group, which is a phenyl ring attached to a carbonyl group, can also contribute to the molecule's lipophilicity. This group can enhance the molecule's ability to penetrate the lipid bilayer of the artificial membrane.

5. **Carbonyl Group**: The carbonyl group in the benzoyl moiety can participate in hydrogen bonding, which may aid in the molecule's interaction with the membrane and potentially increase permeability.

Overall, the given molecule's combination of heterocyclic rings, lipophilic methoxy groups, and functional groups capable of hydrogen bonding suggests that it would exhibit high permeability in the PAMPA assay. These structural features enable the molecule to effectively interact with the artificial membrane, facilitating its passage through the membrane.

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 triazole family, which is known for its diverse biological activities. The molecule's structure includes a triazole ring, which is a five-membered ring containing three nitrogen atoms. This triazole ring is often associated with high stability and resistance to metabolic degradation, which can enhance the molecule's bioavailability.

The molecule also contains a piperidine ring, which is a six-membered ring with one nitrogen atom. Piperidine rings are commonly found in pharmaceuticals due to their ability to enhance the solubility and permeability of compounds. The presence of this ring suggests that the molecule may have favorable pharmacokinetic properties.

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

The benzoyl group in the structure is a phenyl ring attached to a carbonyl group. This group can contribute to the molecule's overall hydrophobic character, which may facilitate its passage through lipid-rich environments, such as cell membranes.

Overall, the combination of these structural features suggests that the given molecule likely has high permeability to the artificial membrane, as it possesses both hydrophilic and hydrophobic characteristics that can aid in membrane permeation.

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:** 0

**Correct:** 0

# Response:
The given molecule is a complex organic compound that features several distinct functional groups and structural components, 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 ring is a six-membered nitrogen-containing heterocycle. This structure is relatively flexible and can enhance the molecule's solubility and permeability. The presence of the nitrogen atom can also facilitate hydrogen bonding interactions with the membrane, potentially increasing permeability.

3. **Triazol-3-one Moiety**: The triazol-3-one group is a five-membered ring containing nitrogen atoms, which can participate in hydrogen bonding and other polar interactions. This group can enhance the molecule's ability to interact with the polar components of the artificial membrane, potentially increasing its permeability.

4. **Methoxyphenyl Group**: The methoxyphenyl group introduces an aromatic ring with a methoxy substituent. The aromatic ring can engage in π-π interactions with the membrane, while the methoxy group can enhance solubility and polarity. This can contribute to moderate permeability due to the balance between hydrophobic and hydrophilic interactions.

Overall, the given molecule's structural features suggest that it may exhibit moderate to high permeability in the PAMPA assay. The combination of rigid and flexible components, along with polar and non-polar groups, allows the molecule to interact effectively with the artificial membrane, facilitating its passage through the membrane.

Final answer: Low-to-moderate permeability.

------
# 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 member of the triazoles, which are known for their diverse biological activities. The structure of the given molecule includes several key features that influence its permeability:

1. **Triazole Ring**: The presence of a triazole ring is significant as it often contributes to the molecule's stability and ability to interact with biological targets. Triazoles are known for their ability to form hydrogen bonds and participate in π-π interactions, which can enhance the molecule's binding affinity to biological membranes.

2. **Fluorophenyl Group**: The fluorine atom in the fluorophenyl group can increase the lipophilicity of the molecule, which may enhance its ability to permeate lipid membranes. 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 can increase the molecule's overall polarity, which may affect its solubility and permeability. The presence of this group can also influence the molecule's ability to form hydrogen bonds, which is crucial for its interaction with the membrane.

4. **Piperidine Ring**: The piperidine ring is a common structural motif in many pharmaceuticals and can enhance the molecule's ability to permeate biological membranes. Its presence can also contribute to the molecule's overall conformational flexibility, which may aid in its interaction with the membrane.

Overall, the combination of these structural features suggests that the given molecule may exhibit moderate to high permeability in the PAMPA assay. The balance of lipophilic and polar groups, along with the triazole ring, likely facilitates its passage through the artificial membrane.

Final answer: High permeability

------
# 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 to understand its permeability:

1. **Piperidine Rings**: The molecule contains two piperidine rings, one of which is substituted with a cyclopropyl group. Piperidine rings are typically hydrophilic due to their nitrogen atom, which can participate in hydrogen bonding. However, the presence of bulky groups like cyclopropyl and tert-butyl can increase the lipophilicity of the molecule, potentially enhancing its ability to permeate the lipid-rich environment of the artificial membrane.

2. **Sulfonyl Group**: The sulfonyl group attached to the pyrrolopyrimidine core is a polar functional group that can increase the molecule's solubility in water. This group can also participate in hydrogen bonding, which may facilitate interactions with the polar head groups of the artificial membrane.

3. **Pyrrolopyrimidine Core**: The pyrrolopyrimidine core is a bicyclic structure 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 enhancing its permeability.

4. **Amino Group**: The presence of an amino group on the piperidine ring can increase the molecule's hydrophilicity and ability to form hydrogen bonds. This can enhance the molecule's interaction with the polar head groups of the artificial membrane, potentially improving its permeability.

5. **Tert-butyl Group**: The tert-butyl group is a bulky, hydrophobic moiety that can increase the lipophilicity of the molecule. This can enhance the molecule's ability to permeate the lipid bilayer of the artificial membrane.

Overall, the given molecule has a combination of hydrophilic and lipophilic features, which suggests that it may have moderate to high permeability in the PAMPA assay. The balance of polar and non-polar groups allows it to interact with both the polar head groups and the lipid tails of the artificial membrane, facilitating its passage through the membrane.

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:** 1

**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 ring and a thiophene 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 permeation through the membrane.

2. **Methoxy Group**: The presence of a methoxy group on the phenyl ring introduces a degree of polarity to the molecule. This can enhance solubility in polar environments and may also influence the molecule's ability to form hydrogen bonds with the membrane, potentially aiding in permeability.

3. **Oxazole Ring**: The oxazole ring is a heterocyclic aromatic compound that can contribute to the molecule's overall stability and rigidity. The nitrogen and oxygen atoms in the oxazole ring can participate in hydrogen bonding, which may affect the molecule's interaction with the membrane.

4. **Thiophene Ring**: The thiophene ring is another aromatic heterocycle that can enhance the molecule's lipophilicity. This can improve the molecule's ability to traverse the hydrophobic regions of the artificial membrane.

5. **Carbamoyl and Carbamoylamine Groups**: These functional groups introduce additional polar characteristics to the molecule. The carbamoyl group can form hydrogen bonds, which may enhance the molecule's interaction with the polar regions of the membrane. The carbamoylamine group can also participate in hydrogen bonding, potentially aiding in permeability.

Overall, the given molecule's combination of aromatic rings, polar functional groups, and heterocyclic elements suggests that it would exhibit high permeability in the PAMPA assay. The balance of hydrophobic and hydrophilic interactions allows the molecule to effectively interact with the artificial membrane, facilitating its passage through the membrane.

Final answer: High permeability

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# 124

**SMILES:** CC(C)C1=CC(=NN1)C(=O)N2CC[C@H](C2)NC(=O)C3CC3

**Label:** 0

**Predi:** 0

**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 to understand its permeability characteristics.

1. **Cyclopropanecarbonyl Group**: The presence of a cyclopropanecarbonyl group introduces a degree of rigidity and steric hindrance to the molecule. Cyclopropane rings are known for their strained three-membered structure, which can affect the molecule's overall conformation and potentially its ability to interact with the artificial membrane. This structural feature might contribute to moderate permeability due to the steric effects and the potential for specific interactions with the membrane.

2. **Pyrrolidine Ring**: The pyrrolidine ring is a five-membered nitrogen-containing heterocycle. This ring can enhance the molecule's solubility and ability to form hydrogen bonds, which are crucial for permeability. The presence of the pyrrolidine ring can facilitate interactions with the membrane, potentially increasing permeability.

3. **Carboxamide Group**: The carboxamide group is a polar functional group that can form hydrogen bonds with the artificial membrane. This group is likely to enhance the molecule's solubility in aqueous environments and can contribute to its permeability by facilitating interactions with the membrane.

4. **1-(1-Methylpropyl)pyrazole Moiety**: The pyrazole ring is a five-membered aromatic heterocycle that can contribute to the molecule's overall stability and ability to interact with the membrane. The methylpropyl substituent adds hydrophobic character, which might influence the balance between hydrophilic and hydrophobic interactions with the membrane, potentially affecting permeability.

Overall, the given molecule contains a mix of polar and non-polar features, along with structural rigidity and potential for hydrogen bonding. These characteristics suggest that the molecule may exhibit moderate permeability in the PAMPA assay, balancing between hydrophilic and hydrophobic interactions with the artificial membrane.

Final answer: Low-to-moderate 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 a complex organic compound with several functional groups and heterocyclic structures that influence its permeability in the PAMPA assay. 

The presence of the fluorine atom in the pyrazolo[4,3-b]pyridine moiety can enhance the molecule's lipophilicity, which often increases membrane permeability. Fluorine can also affect the electronic properties of the molecule, potentially facilitating interactions with the artificial membrane.

The pyrazolo[4,3-b]pyridin-2-one core is a bicyclic structure that can contribute to the molecule's rigidity and planarity, which may enhance its ability to traverse the membrane by fitting into the membrane's lipid bilayer more effectively.

The methoxyethoxy group attached to the quinazolinone moiety introduces a degree of polarity to the molecule, which can influence its solubility and permeability. This group may enhance the molecule's ability to interact with the polar head groups of the artificial membrane, potentially increasing permeability.

The quinazolinone structure itself is a known pharmacophore in many bioactive compounds, and its presence in the given molecule suggests potential interactions with the membrane through hydrogen bonding or π-π stacking.

Overall, the combination of lipophilic and polar functional groups, along with the rigid bicyclic structures, suggests that the given molecule likely exhibits high permeability in the PAMPA assay.

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 potential impact on 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 influence the molecule's interaction 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 affect its permeability by interacting with the polar head groups of the artificial membrane.

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.

Overall, the given molecule's structure suggests a balance of hydrophilic and hydrophobic properties, with multiple functional groups capable of interacting with the artificial membrane. The presence of heterocyclic rings, amino and hydroxyl groups, and a tert-butyl group suggests that the molecule may exhibit moderate permeability in the PAMPA assay, allowing it to interact with the membrane while maintaining some solubility in the aqueous environment.

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 organic compound with multiple functional groups and ring systems, which can influence its permeability in the PAMPA assay. Let's break down the structural features and their potential impact on permeability:

1. **Pyridine Ring with Chlorine Substitution**: The presence of a chlorinated pyridine ring can increase the lipophilicity of the molecule. Chlorine atoms can enhance the molecule's ability to interact with lipid membranes, potentially increasing its permeability.

2. **Imidazo[1,2-a]pyridine Moiety**: This bicyclic structure is relatively planar and aromatic, which can facilitate interactions with the lipid bilayer of the artificial membrane. Aromatic systems often enhance permeability due to their ability to engage in π-π interactions with the membrane.

3. **Piperidine Ring**: The piperidine ring is a saturated, flexible, and polar structure that can enhance the molecule's solubility in aqueous environments. This balance of hydrophilic and lipophilic properties can aid in permeability.

4. **Azaspirodecane System**: The spirocyclic structure introduces rigidity and three-dimensionality to the molecule. This can affect how the molecule fits into the membrane, potentially influencing its permeability.

5. **Methanone Group**: The carbonyl group in the methanone moiety can form hydrogen bonds with the membrane, which may enhance permeability by stabilizing interactions with the membrane.

Overall, the given molecule contains a combination of lipophilic and hydrophilic features, along with aromatic and flexible components, which suggest that it may have moderate to high permeability in the PAMPA assay. The balance of these structural elements allows the molecule to interact favorably with the artificial membrane, facilitating its passage through the membrane.

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. Let's break down the structural components and their potential impact on permeability:

1. **Indole Core**: The indole structure is a bicyclic compound consisting of a benzene ring fused to a pyrrole ring. This core is relatively planar and hydrophobic, which can facilitate membrane permeability due to its ability to interact with lipid bilayers through hydrophobic interactions.

2. **Fluorine Substitution**: The presence of a fluorine atom on the indole ring can influence the molecule's electronic properties and lipophilicity. Fluorine is highly electronegative, which can enhance the molecule's ability to penetrate lipid membranes by increasing its overall lipophilicity.

3. **Pyrazole Ring**: The pyrazole ring is a five-membered heterocycle containing two nitrogen atoms. This ring can participate in hydrogen bonding and other polar interactions, which may affect the molecule's solubility and permeability. The presence of a methyl group on the pyrazole ring can further modulate its lipophilicity and steric properties.

4. **Pyrimidinyl Group**: The pyrimidinyl group is another heterocyclic component that can engage in hydrogen bonding and other polar interactions. This group can enhance the molecule's ability to interact with biological targets, but it may also affect permeability by introducing polar characteristics.

5. **Carbonyl Group**: The carbonyl group in the indole-3-one moiety is a polar functional group that can participate in hydrogen bonding. This group may influence the molecule's solubility and permeability by increasing its interaction with aqueous environments.

Overall, the given molecule's structure suggests a balance between hydrophobic and hydrophilic properties. The indole core and fluorine substitution likely contribute to high permeability through lipid membranes, while the pyrazole and pyrimidinyl groups introduce polar characteristics that may affect solubility and permeability. Therefore, the given molecule is likely to exhibit high permeability in the PAMPA assay.

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. This structure suggests that it has a rigid, planar framework, which is typical of many alkaloids. The presence of multiple rings, including aromatic and heterocyclic rings, contributes to its stability and potential interactions with biological membranes.

The molecule contains a hydroxyethyl group, which can enhance its solubility in water due to the presence of the hydroxyl group. This functional group can also participate in hydrogen bonding, which may facilitate interactions with the artificial membrane.

Additionally, the molecule has an isopropylamino group, which introduces a basic nitrogen atom. This can lead to ionic interactions with the negatively charged components of the artificial membrane, potentially increasing its permeability.

Overall, the combination of aromatic rings, heterocyclic structures, and functional groups like hydroxyethyl and isopropylamino suggests that the given molecule may have moderate to high permeability in the PAMPA assay, as these features can enhance its ability to interact with and pass through the artificial membrane.

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:** 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.

Firstly, the molecule contains a furan ring, which is a five-membered aromatic ring with one oxygen atom. Furan rings are known for their planar structure and aromaticity, which can enhance the molecule's ability to interact with the artificial membrane through π-π stacking interactions. This can contribute to moderate permeability.

Additionally, the molecule includes a methoxyphenyl group, which 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, potentially enhancing interactions with the membrane. This feature can also contribute to moderate permeability due to the increased lipophilicity and potential for van der Waals interactions.

The cyclobutyl group in the molecule is a four-membered aliphatic ring, which introduces some rigidity and steric bulk. This can affect the molecule's ability to fit into the membrane pores, potentially reducing permeability. However, the cyclobutyl group is relatively small and may not significantly hinder permeability.

The presence of an amino group and a pyrimidinone moiety introduces polar functional groups, which can form hydrogen bonds with the membrane. This can enhance the molecule's solubility and interaction with the membrane, potentially increasing permeability.

Overall, the combination of aromatic rings, polar functional groups, and a small aliphatic ring suggests that the given molecule would exhibit moderate permeability in the PAMPA assay. The balance of hydrophobic and hydrophilic interactions, along with the structural rigidity and flexibility, allows the molecule to interact effectively with the artificial membrane.

Final answer: Low-to-moderate 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 cyclopenta[a]phenanthrene core structure, which is a common framework in many natural steroids. This structure is characterized by a series of fused rings, including a cyclopentane ring and three phenanthrene rings. The presence of multiple chiral centers in the molecule suggests that it has a specific three-dimensional conformation, which is crucial for its biological activity and interaction with biological membranes.

The molecule contains several functional groups that influence its permeability:

1. **Hydroxyl Groups**: The presence of multiple hydroxyl groups (–OH) increases the molecule's polarity, which can enhance its solubility in aqueous environments. This can facilitate the molecule's interaction with the polar head groups of the artificial membrane, potentially increasing its permeability.

2. **Ketone Groups**: The presence of ketone groups (C=O) contributes to the molecule's overall polarity and can participate in hydrogen bonding with the membrane. This can also affect the molecule's ability to permeate the membrane by interacting with the membrane's polar regions.

3. **Methyl Groups**: The presence of several methyl groups (–CH₃) increases the hydrophobic character of the molecule. This can enhance the molecule's ability to interact with the hydrophobic regions of the artificial membrane, potentially increasing its permeability.

4. **Double Bonds**: The presence of a double bond in the side chain can introduce rigidity to the molecule, affecting its conformation and how it interacts with the membrane. The configuration of this double bond (Z) can influence the overall shape of the molecule and its ability to fit into the membrane.

Overall, the given molecule's structure suggests that it has a balance of hydrophilic and hydrophobic properties, which can facilitate its permeation through the artificial membrane. The specific arrangement of functional groups and the stereochemistry of the molecule are likely to play a significant role in determining its permeability.

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 to understand its 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 interaction with the membrane.

2. **Bromophenyl Group**: The bromophenyl moiety introduces a halogen atom (bromine) into the structure, which can increase the lipophilicity of the molecule. This increased lipophilicity can enhance the molecule's ability to permeate through the lipid-rich artificial membrane.

3. **Pyridinyl Group**: The pyridinyl group is a heteroaromatic ring that can participate in π-π interactions with the membrane. This can also contribute to the molecule's permeability by facilitating its passage through the membrane.

4. **Cyano Group**: The cyano group is a polar functional group that can engage in dipole-dipole interactions with the membrane. While it may not increase lipophilicity, it can still contribute to the molecule's overall ability to interact with the membrane.

5. **Alkyl Chain**: The butan-2-yl group provides a hydrophobic character to the molecule, which can enhance its permeability by increasing its solubility in the lipid bilayer of the artificial membrane.

Overall, the given molecule has a combination of hydrophilic and hydrophobic features, which suggests that it can effectively interact with the artificial membrane. The presence of hydrogen bonding, π-π interactions, and dipole-dipole interactions, along with the increased lipophilicity due to the bromophenyl group, likely contribute to its high permeability in the PAMPA assay.

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. 

The pyrimidine core is a heterocyclic aromatic compound, which generally contributes to the molecule's ability to interact with biological membranes. The presence of the pyrimidine ring can enhance the molecule's ability to permeate through lipid membranes due to its planar structure and aromaticity, which facilitate interactions with the lipid bilayer.

Additionally, the molecule contains a phenyl group attached to the pyrimidine ring. This phenyl group can increase the hydrophobic character of the molecule, which may enhance its ability to permeate through the lipid-rich environment of the artificial membrane.

The molecule also features a pyridinyl group, which is another aromatic heterocycle. The nitrogen atom in the pyridinyl group can participate in hydrogen bonding, which may affect the molecule's solubility and permeability. However, the presence of this group can also contribute to the overall aromaticity and planarity of the molecule, potentially aiding in membrane permeation.

Furthermore, the molecule has a difluorophenyl group, which introduces fluorine atoms into the structure. Fluorine atoms can increase the lipophilicity of the molecule, enhancing its ability to permeate through lipid membranes. The presence of fluorine can also affect the electronic properties of the molecule, potentially influencing its interaction with the artificial membrane.

Overall, the combination of aromatic rings, the presence of nitrogen atoms, and the difluorophenyl group suggest that the given molecule likely exhibits high permeability in the PAMPA assay due to its ability to interact with the artificial membrane through hydrophobic interactions and potential hydrogen bonding.

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 heterocyclic compound with several 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. **Heterocyclic Core**: The molecule contains a tricyclic system with a thia and diaza component, which suggests a rigid and planar structure. This rigidity can enhance the molecule's ability to interact with the artificial membrane, potentially increasing its permeability. The presence of nitrogen and sulfur atoms in the rings can also contribute to hydrogen bonding and dipole interactions, which may facilitate membrane passage.

2. **Acetyl Groups**: The molecule has acetyl groups, which are polar and can form hydrogen bonds with the membrane. This can increase the molecule's solubility in the membrane environment, enhancing its permeability.

3. **Phenyl and Trifluoromethylphenyl Groups**: The phenyl and trifluoromethylphenyl groups contribute to the hydrophobic character of the molecule. These groups can interact with the lipid components of the artificial membrane, potentially increasing permeability through hydrophobic interactions.

4. **Trifluoromethyl Group**: The trifluoromethyl group is highly electronegative and can enhance the molecule's lipophilicity. This can improve the molecule's ability to traverse the lipid-rich environment of the artificial membrane.

Overall, the combination of polar and non-polar groups, along with the rigid heterocyclic structure, suggests that the given molecule is likely to have high permeability in the PAMPA assay. The balance of hydrophilic and hydrophobic interactions with the artificial membrane supports its ability to pass through the membrane efficiently.

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:** 1

**Correct:** 1

# 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 depends on the specific substituents attached to them.

2. **Halogen Substituents**: The molecule has halogen atoms, specifically chlorine and fluorine, attached to the phenyl ring. Halogen atoms can increase lipophilicity and membrane permeability due to their ability to participate in van der Waals interactions and potentially enhance the molecule's ability to penetrate lipid membranes.

3. **Amino Group**: The presence of an amine group on the quinazoline ring can influence the molecule's solubility and permeability. Amines can form hydrogen bonds, which may affect the molecule's interaction with the artificial membrane.

4. **Pyridine Ring**: The pyridine ring contributes to the molecule's basicity and can participate in hydrogen bonding and π-π interactions. This can influence the molecule's binding affinity to the artificial membrane.

Overall, the combination of aromatic rings, halogen substituents, and functional groups like the amine and pyridine ring suggests that the given molecule likely exhibits high permeability in the PAMPA assay. The balance of lipophilic and hydrophilic properties, along with the ability to form specific interactions with the membrane, supports this prediction.

Final answer: High permeability

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# 136

**SMILES:** C1CN(CCC1C#N)C2=NC(=CS2)C3=CC=C(C=C3)Br

**Label:** 1

**Predi:** 0

**Correct:** 0

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

Firstly, the molecule contains a thiazole ring, which is a five-membered heterocyclic ring containing both sulfur and nitrogen atoms. 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 contribute to moderate permeability, as the thiazole ring can facilitate some degree of penetration through the membrane.

Additionally, the molecule has a piperidine ring, which is a six-membered nitrogen-containing heterocycle. Piperidine rings are typically flexible and can adopt various conformations, which may aid in the molecule's ability to fit into the membrane's structure. The presence of the piperidine ring can also enhance the molecule's solubility and permeability due to its basic nitrogen, which can participate in ionic interactions with the membrane.

The molecule also features a bromophenyl group, which is a phenyl ring substituted with a bromine atom. The bromine atom can increase the lipophilicity of the molecule, which may enhance its ability to permeate through the lipid-rich regions of the artificial membrane. However, the presence of the bromine atom can also introduce steric hindrance, which might limit the molecule's overall permeability.

Finally, the molecule contains a nitrile group attached to the piperidine ring. Nitrile groups are polar and can engage in dipole-dipole interactions, which might influence the molecule's permeability. However, the nitrile group can also introduce some degree of polarity, which might hinder permeability due to reduced solubility in the lipid environment of the membrane.

Overall, the given molecule's permeability is likely to be moderate due to the interplay of its lipophilic and polar characteristics, as well as the structural flexibility provided by the piperidine ring. The thiazole and bromophenyl groups contribute to moderate permeability, while the nitrile group may introduce some polarity that could limit permeability.

Final answer: Low-to-moderate 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:** 1

**Correct:** 0

# 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, and its permeability is crucial for its potential as a drug candidate.

The molecule contains several key structural elements 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 combination of these structural features suggests that the given molecule may have moderate to high permeability in the artificial membrane. The balance of lipophilic and polar groups, along with the presence of flexible linkages, likely facilitates its passage through the membrane, making it a candidate for further drug development studies.

Final answer: High permeability

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# 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 member of pyridines and contains a nitrile group. The presence of the pyridine rings suggests that the molecule has aromatic characteristics, which can influence its permeability. Pyridine rings are known for their ability to participate in π-π interactions, which can enhance the molecule's ability to interact with the artificial membrane.

The tert-butyl group attached to the molecule introduces steric bulk, which can affect the molecule's ability to fit into the membrane pores. This steric hindrance might reduce the permeability by limiting the molecule's access to the membrane.

Additionally, the nitrile group is a polar functional group that can form hydrogen bonds or dipole-dipole interactions with the membrane. This can enhance the molecule's solubility in the membrane environment, potentially increasing its permeability.

Overall, the combination of aromatic pyridine rings and polar nitrile groups suggests that the given molecule may have moderate permeability due to the balance of hydrophobic and hydrophilic interactions with the artificial membrane. However, the steric effects from the tert-butyl group might slightly reduce its permeability.

Final answer: Low-to-moderate permeability.

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# 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.

In the given molecule, the sulfonamide group is attached to a phenyl ring, which is further substituted with a hydroxyethylamino group. This substitution can increase the molecule's hydrophilicity, potentially improving its solubility in aqueous environments and facilitating its interaction with the artificial membrane.

Additionally, the presence of a thiazole ring, which is a five-membered ring containing both sulfur and nitrogen, can contribute to the molecule's overall stability and ability to form hydrogen bonds. This can further influence the molecule's permeability by affecting its interaction with the membrane.

Overall, the combination of these functional groups suggests that the given molecule may exhibit moderate permeability through the artificial membrane, as the polar sulfonamide group and the hydrophilic hydroxyethylamino group can enhance its solubility and interaction with the membrane, while the aromatic and heterocyclic components may provide some stability and additional interactions.

Final answer: Low-to-moderate permeability.

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# 140

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

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a complex structure that includes several functional groups and heterocyclic components, which influence its permeability in the PAMPA assay. Let's break down the structural features and their potential 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 interactions. Quinazoline derivatives are known for their bioactivity, and their planar structure can facilitate passage through lipid membranes.

2. **Methoxy Groups**: The presence of methoxy groups on the phenyl and quinazoline rings increases the molecule's lipophilicity. Methoxy groups can enhance membrane permeability by increasing the molecule's ability to dissolve in lipid bilayers. They also contribute to the overall electronic properties of the molecule, potentially affecting its interaction with the membrane.

3. **Isoxazole Ring**: The isoxazole ring is a five-membered heterocycle containing both nitrogen and oxygen. This ring can participate in hydrogen bonding and dipole-dipole interactions, which may influence the molecule's binding to the artificial membrane. The isoxazole ring can also contribute to the molecule's overall stability and rigidity, which may affect its permeability.

4. **Overall Molecular Size and Shape**: The combination of these rings and functional groups results in a relatively large and complex molecular structure. While this complexity can lead to specific interactions with the membrane, it may also hinder permeability due to steric effects.

Considering these structural features, the given molecule is likely to exhibit moderate permeability in the PAMPA assay. The balance of lipophilic and polar characteristics, along with the presence of aromatic and heterocyclic rings, suggests that the molecule can interact with the artificial membrane, but the size and complexity may limit its passage.

Final answer: Low-to-moderate 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 known for its planar and aromatic nature, which can facilitate interactions with biological membranes.

The presence of the 3,4-dimethylphenyl group attached to the pyrazolopyrimidine core contributes to the hydrophobic character of the molecule. This hydrophobicity can enhance the molecule's ability to interact with lipid membranes, potentially increasing its permeability.

Additionally, the molecule has a methoxypropan-2-amine moiety. The methoxy group is an ether functional group, which can increase the molecule's solubility in organic solvents and may also influence its ability to permeate through the membrane by providing a degree of polarity.

Overall, the combination of the aromatic pyrazolopyrimidine core, the hydrophobic dimethylphenyl group, and the methoxypropan-2-amine moiety suggests that the given molecule likely exhibits high permeability in the PAMPA assay, as it possesses a balance of hydrophobic and polar characteristics that facilitate membrane interaction.

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 potential impact on permeability:

1. **Indole Moiety**: The presence of an indole ring, which is a bicyclic structure 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.

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 through the PAMPA membrane, which is typically polar.

3. **Carboxamide Group**: The carboxamide group is a polar functional group that can form hydrogen bonds with the membrane. This can enhance the molecule's interaction with the membrane and potentially increase its permeability.

4. **Phenyl Groups**: The presence of phenyl groups, both in the indole and attached to the sulfonyl group, contributes to the hydrophobic character of the molecule. These aromatic rings can facilitate van der Waals interactions with the membrane, which may aid in permeability.

5. **Overall Molecular Structure**: The combination of aromatic rings and polar functional groups suggests that the given molecule has a balance of hydrophobic and hydrophilic properties. This balance can enhance its ability to traverse the PAMPA membrane, indicating a potential for high permeability.

In summary, the given molecule's structural features, including the indole moiety, sulfonyl group, carboxamide group, and phenyl rings, suggest that it may exhibit high permeability in the PAMPA assay due to its ability to interact with the artificial membrane through a combination of hydrophobic and polar interactions.

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. The pyrazolo[3,4-d]pyrimidine core is known for its planar and aromatic nature, which can facilitate interactions with the artificial membrane. Aromatic systems often enhance permeability due to their ability to engage in π-π stacking and other non-covalent interactions with the membrane.

2. **Imidazole Group**: The presence of an imidazole ring introduces a polar and heteroaromatic component to the molecule. Imidazole rings are known for their ability to form hydrogen bonds, which can enhance the molecule's solubility and interaction with the membrane. This can contribute to moderate permeability, as the polar nature of the imidazole group can facilitate passage through the membrane while also allowing for specific interactions.

3. **Aromatic Substituents**: The given molecule contains a 3-chloro-6-methylphenyl group. The chloro substituent can influence the lipophilicity of the molecule, potentially enhancing its ability to traverse the lipid-rich environment of the artificial membrane. The methyl group adds to the hydrophobic character, which can also promote membrane permeability.

4. **Amino Linkages**: The presence of amino groups in the structure can enhance the molecule's ability to form hydrogen bonds, which may aid in its interaction with the membrane. These linkages can also contribute to the overall solubility of the molecule, which is crucial for permeability.

Overall, the combination of aromatic and heteroaromatic rings, along with polar functional groups, suggests that the given molecule would exhibit moderate to high permeability in the PAMPA assay. The balance of hydrophobic and hydrophilic characteristics allows it to interact effectively with the artificial membrane, facilitating its passage.

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 ring system. This bicyclic structure is relatively rigid and planar, which can facilitate interactions with the artificial membrane. The presence of nitrogen atoms in the ring can contribute to hydrogen bonding and polar interactions, potentially enhancing permeability.

2. **Dimethyl Substituents**: The dimethyl groups attached to the pyrazolopyridazine core increase the hydrophobic character of the molecule. This can enhance the ability of the molecule to interact with the lipid components of the artificial membrane, potentially increasing permeability.

3. **4-Methylphenyl Group**: The presence of a 4-methylphenyl group adds to the hydrophobicity and can also contribute to π-π stacking interactions with the membrane. This aromatic group can enhance the molecule's ability to traverse the membrane by interacting with the hydrophobic regions.

4. **Piperazine Moiety**: The piperazine ring is a flexible, nitrogen-containing heterocycle that can enhance solubility and permeability. The ethyl group attached to the piperazine can increase the lipophilicity of the molecule, which may aid in membrane permeation.

5. **Propyl Linker**: The propyl chain connecting the piperazine to the pyrazolopyridazine core provides flexibility and spatial separation, which can influence the overall conformation of the molecule and its ability to fit into the membrane.

Overall, the given molecule contains a combination of hydrophobic and polar features that suggest it may have moderate to high permeability in the PAMPA assay. The balance of hydrophobic and polar interactions, along with the rigid and flexible components, likely allows the molecule to effectively interact with the artificial membrane, facilitating its passage through the assay.

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 sulfonamide, which is a class of compounds known for their antimicrobial properties. To predict its permeability in the PAMPA assay, we need to consider the structural features of the molecule.

The molecule contains a 1,4-dioxo-1,2,3,4-tetrahydropyrazolyl group, which is a heterocyclic structure that can contribute to the molecule's overall polarity and potential hydrogen bonding capabilities. This group may enhance the molecule's ability to interact with the artificial membrane, potentially increasing its permeability.

Additionally, the molecule has a 2,3-dihydro-1H-indenyl moiety, which is a bicyclic structure that can provide rigidity and hydrophobic character. This feature might help the molecule to traverse the membrane by interacting with the lipid components of the artificial membrane.

The presence of a 2,3-dihydro-1,4-benzodioxinyl group introduces an aromatic ether, which can contribute to the molecule's overall lipophilicity. This can enhance the molecule's ability to permeate the membrane by increasing its solubility in the lipid bilayer.

The acetamide group in the molecule can form hydrogen bonds, which may facilitate interactions with the membrane and improve permeability.

Overall, the combination of these structural features suggests that the given molecule likely has moderate to high permeability in the PAMPA assay due to its balance of hydrophilic and hydrophobic properties, as well as its ability to form hydrogen bonds.

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 that features several distinct structural components, each contributing to its permeability characteristics in the PAMPA assay.

Firstly, the molecule contains a pyridine ring, which is a nitrogen-containing heterocycle. Pyridine rings are known for their ability to engage 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 includes an imidazo[1,2-a]pyridine moiety. This bicyclic structure is a fused ring system that can increase the rigidity of the molecule, potentially improving its ability to fit into the membrane's pores. The presence of nitrogen atoms in this moiety can also enhance the molecule's ability to form hydrogen bonds, further aiding its permeability.

The phenyl group attached to the imidazo[1,2-a]pyridine system is a hydrophobic aromatic ring. This hydrophobic character can facilitate the molecule's passage through the lipid components of the artificial membrane, promoting permeability.

Finally, the presence of a methanol group introduces a polar hydroxyl group, which can form hydrogen bonds with the membrane. This can enhance the molecule's solubility in the aqueous environment of the PAMPA assay, potentially improving its permeability.

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, as well as structural rigidity and the ability to form multiple interactions with the 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 potential impact on permeability:

1. **Fluorinated Aromatic Ring**: The presence of a trifluoromethyl group and two fluorine atoms on the aromatic ring increases the lipophilicity of the molecule. Fluorine atoms can enhance the molecule's ability to interact with lipid membranes, potentially increasing its permeability.

2. **Thiazole Ring**: The thiazole ring is a heterocyclic compound containing both sulfur and nitrogen. This ring can contribute to the molecule's overall stability and rigidity, which may affect its ability to permeate the membrane. The presence of sulfur can also influence the molecule's electronic properties, potentially affecting its interaction with the membrane.

3. **Phenoxy Group**: The phenoxy group, which is an ether linkage, can increase the molecule's flexibility and solubility. This group may help the molecule to better orient itself within the membrane, potentially enhancing permeability.

4. **Methylthio Linkage**: The methylthio group introduces a sulfur atom, which can increase the molecule's lipophilicity. This can enhance the molecule's ability to traverse lipid membranes.

5. **Acetic Acid Moiety**: The acetic acid group is a polar functional group that can increase the molecule's solubility in aqueous environments. However, it may also introduce some degree of polarity that could hinder membrane permeability due to the need for specific interactions with the membrane.

Overall, the given molecule's structure suggests that it has a balance of lipophilic and polar characteristics. The presence of fluorinated aromatic rings and sulfur-containing groups likely contribute to high permeability, while the acetic acid moiety may provide some solubility and 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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# 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 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 a sulfonamide group attached to a phenyl ring, which is further substituted with a hydroxy-methylphenyl group. This hydroxy group can form hydrogen bonds, potentially increasing the molecule's solubility and permeability.

Additionally, the molecule contains a thiazole ring, which is a five-membered ring containing both sulfur and nitrogen. The presence of this heterocyclic ring can contribute to the molecule's overall stability and ability to interact with biological targets, potentially enhancing its permeability.

The phenyl ring linked to the thiazole moiety suggests a planar structure, which can facilitate passage through lipid membranes due to its ability to intercalate between lipid molecules.

Overall, the combination of these functional groups and structural features suggests that the given molecule likely exhibits high permeability in the PAMPA assay, allowing it to effectively interact with the artificial membrane.

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 an aromatic amide, which suggests that it contains an amide functional group attached to an aromatic ring. This structural feature is often associated with moderate to high permeability in biological membranes due to the presence of both hydrophilic and hydrophobic regions.

The molecule contains a pyrrole ring, which is a five-membered aromatic heterocycle. Pyrrole 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 molecule has a trifluoromethoxy group attached to a phenyl ring. The trifluoromethoxy group is highly electronegative due to the presence of fluorine atoms, which can increase the molecule's lipophilicity. This can enhance the molecule's ability to permeate lipid membranes by increasing its solubility in nonpolar environments.

The carboxamide group in the molecule can form hydrogen bonds with the membrane, potentially aiding in its permeation. However, the presence of the trifluoromethoxy group may counteract this by increasing the overall lipophilicity of the molecule.

Overall, the combination of aromatic rings, the trifluoromethoxy group, and the carboxamide group suggests that the given molecule likely exhibits high permeability in the artificial membrane used in the PAMPA assay.

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 contributes to the molecule's ability to permeate through lipid membranes, as it can engage in π-π interactions and hydrogen bonding with the membrane components.

The presence of the carboxamide group in the molecule suggests that it can form hydrogen bonds, which may enhance its solubility in aqueous environments and facilitate its interaction with the polar head groups of the artificial membrane. This functional group can also contribute to the molecule's overall stability and binding affinity to the membrane.

Additionally, the hydroxyethyl group provides an additional site for hydrogen bonding, which can further enhance the molecule's interaction with the membrane. This group can increase the molecule's hydrophilicity, potentially improving its permeability by allowing it to interact more effectively with the polar regions of the membrane.

Overall, the combination of the benzimidazole core, carboxamide, and hydroxyethyl groups suggests that 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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# 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 can facilitate interactions with the artificial membrane and potentially enhance permeability.

Overall, the combination of the oxadiazole ring, methoxyphenyl groups, and amine functionality suggests that the given molecule may exhibit high permeability in the PAMPA assay due to its balanced hydrophilic and lipophilic properties.

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 membranes, which can influence its permeability.

In the given molecule, the presence of the sulfonamide group suggests that it may have moderate 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. However, the overall permeability will also depend on the other structural features of the molecule.

The molecule also contains aromatic rings, which can contribute to its lipophilicity. The presence of these rings can enhance the molecule's ability to interact with the lipid components of the membrane, potentially increasing its permeability. However, the hydrophilic nature of the sulfonamide group may counterbalance this effect, leading to a more moderate permeability.

Additionally, the molecule has a hydroxyl group attached to a phenyl ring, which can increase its hydrophilicity and potentially improve its solubility in aqueous environments. This could also affect its permeability by allowing it to form additional hydrogen bonds with the membrane.

Overall, the given molecule is likely to exhibit low-to-moderate permeability in the artificial membrane, balancing the effects of its polar and non-polar components.

Final answer: Low-to-moderate permeability.

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# 153

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

**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 framework is known for its potential biological activity and is often explored in drug discovery for its pharmacological properties.

The presence of a bromine atom on the thiophene ring can influence the molecule's lipophilicity and electronic properties, potentially enhancing its ability to interact with biological membranes. Bromine is a relatively large and electronegative atom, which can contribute to the molecule's overall hydrophobic character and may facilitate its passage through lipid membranes.

Additionally, the molecule contains a tetrazole ring, which is a five-membered ring containing four nitrogen atoms. The tetrazole moiety is known for its ability to mimic the carboxylic acid group, often used in medicinal chemistry to improve the pharmacokinetic properties of a compound. The presence of the tetrazole ring can also enhance the molecule's solubility and its ability to form hydrogen bonds, which may aid in its permeability across biological membranes.

The thienopyrimidine core, combined with the bromine and tetrazole substituents, suggests that the given molecule may exhibit moderate to high permeability in the PAMPA assay. This is due to the balance of hydrophobic and hydrophilic properties, as well as the potential for favorable interactions with the artificial membrane.

Final answer: High 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:** 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. **Imidazo[1,2-a]pyrazine 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. This core is often found in biologically active compounds, suggesting that the given molecule may have a favorable interaction with the membrane.

2. **Amino Group**: The presence of an amino group can increase the molecule's hydrophilicity, which may enhance its solubility in aqueous environments. However, it can also form hydrogen bonds with the membrane, potentially increasing permeability.

3. **Pyridine Carboxamide**: The pyridine ring is another aromatic system that can participate in π-π interactions with the membrane. The carboxamide group can form hydrogen bonds, which may aid in membrane interaction and permeability.

4. **Prop-2-enoyl Group**: This group contains an alkene, which can introduce some rigidity to the molecule. The presence of this group may influence the overall shape and flexibility of the molecule, affecting how it fits into the membrane.

5. **Pyrrolidine Ring**: The pyrrolidine ring is a saturated, non-aromatic heterocycle that can add to the molecule's structural complexity. It may influence the molecule's conformation and how it interacts with the membrane.

6. **Chirality**: The molecule has a chiral center, which can affect its interaction with the membrane. The specific stereochemistry (R configuration) may influence the molecule's binding affinity and permeability.

Overall, the given molecule has a combination of aromatic and polar functional groups that suggest it could have moderate to high permeability in the PAMPA assay. The balance of hydrophilic and hydrophobic interactions, along with the structural rigidity and flexibility provided by the various functional groups, likely contribute to its ability to traverse the artificial membrane.

Final answer: High 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 complex organic compound that includes several functional groups and structural features that influence its permeability in the PAMPA assay. 

The presence of the methoxy groups on the pyridine ring contributes to the molecule's lipophilicity, which can enhance its ability to permeate through the artificial membrane. These groups can increase the molecule's overall hydrophobic character, facilitating its passage through the lipid-like environment of the membrane.

Additionally, the imidazo[4,5-b]pyridine core is a bicyclic structure that can provide rigidity and stability to the molecule, potentially aiding in its interaction with the membrane. This core structure is often associated with bioactive compounds, which may also suggest a favorable interaction with the membrane.

The sulfinyl linkage, which connects the pyridine and imidazo[4,5-b]pyridine moieties, introduces a polar element to the molecule. This group can participate in hydrogen bonding or dipole-dipole interactions with the membrane, which may influence the permeability.

Overall, the combination of lipophilic methoxy groups, the rigid imidazo[4,5-b]pyridine core, and the polar sulfinyl linkage suggests that the given molecule likely exhibits high permeability in the PAMPA assay.

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 potential impact on permeability:

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 on the indazole 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.

3. **Benzoxazole Moiety**: The benzoxazole ring is another aromatic system that can contribute to the molecule's overall aromatic character. This can facilitate interactions with the membrane through similar π-π stacking interactions, potentially aiding in permeability.

4. **Piperidine Ring**: The piperidine ring is a saturated six-membered ring containing a nitrogen atom. This structure can increase the molecule's flexibility and solubility, which may enhance its ability to permeate the artificial membrane. The presence of a carbonyl group attached to the piperidine ring can also form hydrogen bonds with the membrane, potentially aiding in permeation.

5. **Carbonyl Group**: The carbonyl group in the piperidine ring can act as a hydrogen bond acceptor, which may facilitate interactions with the membrane and enhance permeability.

Overall, the given molecule's combination of aromatic rings, fluorine substitution, and functional groups like the carbonyl and piperidine ring suggest that it may have high permeability in the PAMPA assay. These structural features enable the molecule to engage in various non-covalent interactions with the artificial membrane, potentially allowing it to pass through efficiently.

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:** 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.

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

1. **Sulfonamide Group**: The presence of the sulfonamide moiety, specifically the 4-methylbenzenesulfonyl group, contributes to the molecule's polarity. This group can form hydrogen bonds and ionic interactions, which can enhance the molecule's solubility in aqueous environments and its ability to permeate biological membranes.

2. **Pyridine Ring**: The pyridine ring is a heteroaromatic structure that can participate in π-π interactions with the lipid bilayer of cell membranes. This can facilitate the passage of the molecule through the membrane.

3. **Thiazole Ring**: The thiazole ring is another heteroaromatic structure that can contribute to the molecule's overall stability and ability to interact with biological targets. The presence of sulfur and nitrogen in the thiazole ring can enhance the molecule's ability to form hydrogen bonds and coordinate with metal ions, which may be present in the membrane.

4. **Phenyl Group**: The phenyl group is a hydrophobic moiety that can interact with the lipid components of the membrane. This interaction can help the molecule to embed itself within the lipid bilayer, enhancing its permeability.

Overall, the combination of these functional groups 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 the sulfonamide group, in particular, indicates that the molecule is likely to have high permeability due to its ability to form strong interactions with the membrane.

Final answer: High 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:** 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 to understand its permeability characteristics.

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 hydrophobicity, which is crucial for permeability. The hydrophobic nature might hinder permeability if the membrane is more hydrophilic.

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 overall hydrophobicity of the molecule. This may reduce permeability if the membrane is polar.

5. **Aryl Amide Linkage**: The amide linkage between the pyrrole and the aryl group introduces a polar functional group that can participate in hydrogen bonding. This can enhance solubility and permeability, especially if the membrane is polar.

6. **Bromophenyl Group**: The presence of a bromine atom on the phenyl ring adds to the molecule's overall size and may affect its ability to fit into the membrane pores. The bromine atom is also relatively polarizable, which can influence interactions with the membrane.

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, potentially increasing permeability due to enhanced aromatic interactions.

Overall, the given molecule has a mix of polar and non-polar characteristics, with several functional groups that can interact with the artificial membrane. The balance of these interactions will determine its permeability. The presence of aromatic rings and polar functional groups suggests that the molecule may have moderate to high permeability, depending on the specific nature of the artificial membrane used in the PAMPA assay.

Final answer: Low-to-moderate permeability.

------
# 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 an aromatic ether, which indicates the presence of an ether linkage involving an aromatic ring. This structural feature can influence the molecule's permeability by affecting its solubility and interaction with the artificial membrane.

The molecule contains a phenoxyphenyl group, which is an aromatic ether. This group contributes to the molecule's lipophilicity, potentially enhancing its ability to interact with the hydrophobic regions of the artificial membrane. The presence of aromatic rings can also facilitate π-π interactions with the membrane, which may further increase permeability.

Additionally, the molecule includes a thiazole ring, which is a heterocyclic compound containing both sulfur and nitrogen. This ring can contribute to the molecule's overall polarity and may affect its ability to form hydrogen bonds or other interactions with the membrane.

The piperidine ring, which is a six-membered nitrogen-containing ring, can enhance the molecule's solubility in water due to its basic nature. This can improve the molecule's overall balance between hydrophilicity and lipophilicity, potentially aiding in its permeability through the membrane.

Overall, the combination of aromatic ether characteristics, aromatic rings, and heterocyclic components suggests that the given molecule may exhibit high permeability in the Parallel Artificial Membrane Permeability Assay (PAMPA).

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:** 0

**Correct:** 0

# 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.

Additionally, the methyl group on the indole ring can contribute to the molecule's hydrophobic character, which may facilitate its passage through the lipid components of the artificial membrane.

The phenyl group attached to the indole structure adds further hydrophobicity and aromaticity, which can enhance the molecule's ability to interact with the membrane through π-π stacking interactions and van der Waals forces.

The ethanone group, which is a carbonyl functional group, can also participate in hydrogen bonding and dipole-dipole interactions, potentially affecting the molecule's permeability by interacting with polar sites on the membrane.

Overall, the combination of aromatic, hydrophobic, and polar functional groups in the given molecule suggests that it may have moderate permeability through the artificial membrane, as it can engage in various non-covalent interactions with the membrane.

Final answer: Low-to-moderate permeability.

------
# 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 potential 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 hydrophilicity. Piperazine rings are often found in pharmaceuticals and can enhance the solubility of the molecule in aqueous environments, which is beneficial for permeability.

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 interact with lipid membranes. However, the overall effect on permeability will depend on the balance between hydrophilic and hydrophobic components.

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 ability to interact with the artificial membrane, potentially affecting its permeability. Nitro groups can also contribute to the molecule's overall polarity, which may impact its solubility and permeability.

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 ability to interact with the polar components of the artificial membrane, potentially increasing its permeability.

Overall, the given molecule contains a balance of hydrophilic and hydrophobic features, along with functional groups that can participate in various interactions with the artificial membrane. These characteristics suggest that the molecule may exhibit moderate permeability in the PAMPA assay, as it has both the ability to interact with the membrane and maintain solubility in the assay environment.

Final answer: Low-to-moderate permeability.

------
# 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 potential impact on permeability:

1. **Quinazoline Core**: The quinazoline moiety is a bicyclic structure that is relatively planar and aromatic. This can contribute to the molecule's ability to interact with the artificial membrane through π-π stacking interactions, which can enhance permeability.

2. **Chlorine Substitution**: The presence of a chlorine atom on the quinazoline ring can increase the lipophilicity of the molecule. This can enhance its ability to traverse lipid membranes, potentially increasing permeability.

3. **Oxadiazole Ring**: The 1,2,4-oxadiazole ring is a heterocyclic compound that can contribute to the molecule's overall stability and rigidity. The presence of nitrogen and oxygen atoms in this ring can also participate in hydrogen bonding, which may affect the molecule's interaction with the membrane.

4. **Benzoxazole Ring**: The benzoxazole moiety is another heterocyclic structure that can enhance the molecule's aromatic character. The nitrogen and oxygen atoms in this ring can also participate in hydrogen bonding, which may influence the molecule's permeability.

5. **Amino Group**: The amino group attached to the benzoxazole ring can increase the molecule's hydrophilicity, which may enhance its solubility in aqueous environments. This can balance the lipophilic nature of the rest of the molecule, potentially leading to moderate permeability.

6. **Tetrahydroquinazoline Structure**: The partially saturated quinazoline ring (tetrahydroquinazoline) can provide some flexibility to the molecule, which may facilitate its passage through the artificial membrane.

Overall, the given molecule has a combination of aromatic and heterocyclic structures that contribute to its lipophilicity, while the presence of polar functional groups like the amino group can enhance its solubility. 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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# 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 molecule's structure includes several functional groups that influence its permeability.

Firstly, the quinoline core is a bicyclic aromatic compound, which generally contributes to the molecule's ability to interact with biological membranes. Aromatic systems are known for their planar structure, which can facilitate passage through lipid bilayers due to favorable π-π interactions with the lipid tails.

The presence of a sulfonamide group in the molecule 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 molecule's interaction with the artificial membrane.

Additionally, the molecule contains a chloro and two fluoro substituents on the phenyl ring. Halogen atoms, such as chlorine and fluorine, can increase the lipophilicity of a compound, which may enhance its permeability. However, the electron-withdrawing nature of these halogens can also affect the electronic distribution within the molecule, potentially influencing its interaction with the membrane.

The oxo group in the quinoline ring introduces a polar site that can engage in hydrogen bonding, which may affect the molecule's overall permeability by interacting with polar sites on the artificial membrane.

Overall, the combination of aromaticity, sulfonamide functionality, and halogen substituents suggests that the given molecule may exhibit moderate to high permeability in the PAMPA assay, as these features collectively enhance its ability to interact with and pass through 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 structure of the given molecule 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 lipophilic.

2. **Carboxamide Group**: The presence of a carboxamide group in the molecule can enhance its ability to form hydrogen bonds with the membrane, potentially increasing its permeability. However, this group can also introduce some polarity, which might reduce permeability depending on the balance with other hydrophobic parts of the molecule.

3. **Piperidine Ring**: The piperidine moiety is a common feature in many pharmaceuticals and can enhance the molecule's solubility and permeability. The piperidine ring is a secondary amine, which can participate in hydrogen bonding and ionic interactions, potentially aiding in membrane permeation.

4. **Alkyl Chains**: The butyl and methylpropyl groups attached to the piperidine and quinazoline cores, respectively, increase the hydrophobic character of the molecule. These alkyl chains can enhance the lipophilicity of the molecule, which is often associated with better membrane permeability.

5. **Oxidized Quinazoline**: The dioxo groups in the quinazoline ring can contribute to the molecule's overall polarity. However, in the context of the entire molecule, these groups might not significantly hinder permeability due to the presence of other hydrophobic regions.

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 quinazoline core, combined with the piperidine ring and alkyl chains, likely facilitates its interaction with the artificial membrane, resulting in a high permeability profile.

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:** 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, which can influence its permeability.

The molecule contains several key structural features that contribute to its permeability:

1. **Sulfonamide Group**: The presence of the sulfonamide group, specifically the methoxybenzenesulfonyl moiety, is likely to increase the molecule's polarity. This can enhance its solubility in aqueous environments, which is important for permeability across biological membranes.

2. **Pyridine Ring**: The pyridine ring is a heterocyclic aromatic compound that can contribute to the molecule's ability to interact with biological targets. Its presence can also influence the molecule's electronic properties, potentially affecting its permeability.

3. **Thiazole Ring**: The thiazole ring is another heterocyclic aromatic compound that can enhance the molecule's ability to penetrate biological membranes. The presence of nitrogen and sulfur in the ring can contribute to the molecule's overall polarity and ability to form hydrogen bonds.

4. **Phenyl Group**: The phenyl group is a hydrophobic aromatic ring that can interact with lipid components of the membrane, potentially facilitating the molecule's passage through the membrane.

5. **Carboxamide Group**: The carboxamide group is a polar functional group that can form hydrogen bonds with the membrane, potentially aiding in its permeability.

Overall, the combination of these functional groups suggests that the given molecule may have moderate to high permeability in the PAMPA assay. The balance of hydrophilic and hydrophobic components, along with the ability to form hydrogen bonds, likely facilitates its interaction with the artificial membrane.

Final answer: High 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:** 1

**Correct:** 1

# 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 pyrimido[1,2-a]pyrimidine core, which is a bicyclic system combining pyrimidine and pyrimidine rings. This core is known for its planar structure, which can facilitate interactions with biological membranes.

The presence of the pyrimido[1,2-a]pyrimidine core suggests that the given molecule may have a relatively high permeability due to its planar and aromatic nature. Aromatic compounds often have good membrane permeability because they can pass through lipid bilayers more easily than non-aromatic or highly polar compounds.

Additionally, the molecule contains a 2-chloro-6-fluorophenyl group. The presence of halogen atoms like chlorine and fluorine can influence the molecule's lipophilicity, potentially enhancing its ability to permeate lipid membranes. Halogens can also participate in halogen bonding, which may affect the molecule's interaction with the artificial membrane.

The pyridin-3-yl group attached to the pyrimido[1,2-a]pyrimidine core adds another aromatic ring, which can further contribute to the molecule's overall aromatic character and lipophilicity. This group may also participate in π-π stacking interactions with the artificial membrane, potentially increasing permeability.

Overall, the combination of the pyrimido[1,2-a]pyrimidine core, the halogenated phenyl group, and the pyridinyl group 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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# 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 Moiety**: The molecule contains an indole structure, which is a bicyclic compound 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 aromaticity. This can enhance the molecule's ability to permeate through the artificial membrane, contributing 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 membrane permeability by facilitating interactions with the lipid bilayer of the artificial membrane.

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 aid in the molecule's solubility and permeability. However, the balance between hydrophobic and hydrophilic interactions will determine the overall 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 interaction with the membrane, potentially increasing its permeability.

5. **Amino Group**: The presence of an amino group linked to a pyridine ring can contribute to the molecule's basicity and ability to form hydrogen bonds. This can also influence the molecule's solubility and 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 moiety and dimethyl substitution likely contribute to its ability to permeate the artificial membrane, while the pyridine rings and carboxamide group provide additional interactions that can enhance its permeability. Therefore, the given molecule is likely to exhibit high permeability in the PAMPA assay.

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 molecule's ability to permeate through the lipid bilayer of the artificial membrane, contributing to higher permeability.

3. **Trifluoromethylphenyl Group**: The trifluoromethyl group is highly electronegative and lipophilic. It can increase the molecule's overall lipophilicity, which is beneficial for permeability. However, the electron-withdrawing nature of the trifluoromethyl group can also affect the molecule's interaction with the membrane, potentially reducing permeability if it causes steric hindrance or disrupts membrane integrity.

4. **Piperidine Ring**: The piperidine ring is a saturated nitrogen-containing heterocycle that can enhance the molecule's solubility and permeability. It can also provide a degree of flexibility to the molecule, allowing it to adapt to the membrane structure.

5. **Sulfonyl Group**: The sulfonyl group is polar and can form hydrogen bonds with the artificial membrane. This can increase the molecule's interaction with the membrane, potentially enhancing permeability. However, it can also introduce some degree of polarity, which might reduce permeability if it causes the molecule to be less lipophilic.

Overall, the given molecule has a combination of lipophilic and polar groups that suggest moderate to high permeability in the PAMPA assay. The methoxy and trifluoromethyl groups contribute to lipophilicity, while the sulfonyl and piperidine groups provide polar interactions. The triazole ring further supports stability and permeability. Therefore, the given molecule is likely to exhibit high permeability in the PAMPA assay.

Final answer: High permeability

------
# 169

**SMILES:** CC1CCCCN1C2=NC=NC(=C2[N+](=O)[O-])N

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a pyrimidine derivative with a piperidine ring and a nitro group attached to the pyrimidine core. The presence of the piperidine ring, which is a six-membered ring containing a nitrogen atom, suggests that the molecule may have moderate to high permeability due to the ring's ability to enhance lipophilicity and improve membrane permeability. Piperidine rings are often found in pharmaceutical compounds and can facilitate the crossing of biological membranes.

The nitro group on the pyrimidine ring can influence the molecule's electronic properties, potentially affecting its interaction with the artificial membrane. Nitro groups are electron-withdrawing, which can impact the overall polarity of the molecule. This could either enhance or reduce permeability depending on the balance of hydrophilic and lipophilic properties.

Overall, the combination of the piperidine ring and the nitro group on the pyrimidine core suggests that the given molecule may exhibit high permeability in the PAMPA assay, as these structural features are commonly associated with favorable membrane permeability characteristics.

Final answer: High permeability

------
# 170

**SMILES:** CC1=CC(=NC(=C1)NC(=S)N2CCN(CC2)C3=C(C=C(C=C3)Cl)[N+](=O)[O-])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 these features and their potential impact on permeability:

1. **Piperazine Ring**: The presence of a piperazine ring, which is a six-membered ring containing two nitrogen atoms, is a common feature in many pharmaceuticals. Piperazine rings are generally flexible and can enhance the solubility of the molecule in aqueous environments. This flexibility and solubility can facilitate the passage of the molecule through the artificial membrane, contributing to high permeability.

2. **Carbothioamide Group**: The carbothioamide group, which includes a thioamide linkage, can influence the molecule's polarity and hydrogen bonding capabilities. Thioamides are known for their ability to form hydrogen bonds, which can enhance interactions with the membrane and potentially increase 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, which can affect the molecule's overall polarity and electronic distribution. These groups can influence the molecule's ability to interact with the membrane, potentially affecting permeability. The chloro group can also enhance lipophilicity, which may aid in membrane permeation.

4. **Dimethylpyridine Moiety**: The dimethyl groups on the pyridine ring increase the lipophilicity of the molecule, which can enhance its ability to traverse lipid membranes. The pyridine ring itself is a heteroaromatic system that can participate in π-π interactions with the membrane, potentially aiding in permeability.

Overall, the given molecule's combination of a flexible piperazine ring, polar thioamide group, and lipophilic substituents suggests that it would exhibit high permeability in the PAMPA assay. The balance of hydrophilic and lipophilic properties, along with the ability to form hydrogen bonds and engage in π-π interactions, supports its potential to efficiently pass through the artificial membrane.

Final answer: High permeability

------
# 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. 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 ability to permeate biological membranes. This group is often involved in hydrogen bonding and ionic interactions, which can be crucial for membrane permeability.

2. **Aromatic Rings**: The molecule contains multiple aromatic rings, including a phenyl group and a thiazole ring. Aromatic rings can increase the lipophilicity of the molecule, which may enhance its ability to permeate lipid membranes. However, the balance between hydrophilicity and lipophilicity is crucial for permeability, and the presence of polar groups like the sulfonamide can counteract excessive lipophilicity.

3. **Thiazole Ring**: The thiazole ring is a 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 interaction with biological targets, potentially affecting permeability.

4. **Chlorine Substitution**: The presence of a chlorine atom on the aromatic ring can influence the molecule's electronic properties and its ability to interact with lipid membranes. Chlorine is a relatively electronegative atom, which can affect the molecule's overall polarity and potentially its 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 aromatic rings contribute to its ability to interact with the artificial membrane, while the thiazole ring and chlorine substitution may influence its stability and permeability profile.

Final answer: Low-to-moderate permeability.

------
# 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 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.

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 contribute to the molecule's ability to form hydrogen bonds and engage in π-π interactions, which can further influence its permeability.

Additionally, the molecule contains a methoxy group attached to 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 lipid membranes, as increased lipophilicity generally correlates with better membrane permeability.

The amino group in the molecule is linked to a phenyl ring, which can also participate in hydrogen bonding and other non-covalent interactions with the artificial membrane. This can further influence the molecule's permeability.

Overall, the combination of these functional groups suggests that the given molecule may have moderate to high permeability in the PAMPA assay, as the sulfonamide group, pyridine ring, methoxy group, and amino group collectively contribute to its ability to interact with and permeate the artificial membrane.

Final answer: High permeability

------
# 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 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 acetyl group on the pyrrole ring introduces a polar region, which can enhance the molecule's ability to form hydrogen bonds with the artificial membrane. This can increase its permeability by facilitating interactions with the membrane.

The pyrrole ring itself is a heterocyclic aromatic compound, which contributes to the overall hydrophobic character of the molecule. The methyl groups attached to the pyrrole ring further increase its hydrophobicity, potentially enhancing the molecule's ability to permeate the membrane by interacting with the lipid components.

The sulfonamide group attached to the phenyl ring is a polar and hydrophilic moiety. This group can form strong hydrogen bonds and ionic interactions with the membrane, which may aid in permeability by stabilizing the molecule's interaction with the membrane.

Overall, the combination of hydrophobic aromatic rings and polar functional groups suggests that the given molecule may have moderate permeability to the artificial membrane, as it can interact with both the hydrophobic and hydrophilic components of the membrane.

Final answer: Low-to-moderate permeability.

------
# 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:** 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 to understand its permeability:

1. **Aromatic Amide Group**: The presence of an aromatic amide group, which includes a benzamide moiety, 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. Aromatic amides are known for their ability to participate in π-π interactions, which can facilitate binding to the membrane.

2. **Sulfonamide Group**: The sulfonamide group is a polar functional group that can form hydrogen bonds with the artificial membrane. This group can increase the molecule's solubility in aqueous environments, which is beneficial for permeability. However, the sulfonamide group can also introduce some steric hindrance, which might limit the molecule's ability to pass through the membrane.

3. **Pyrrole Ring**: The pyrrole ring is a heterocyclic aromatic compound that contributes to the molecule's overall aromaticity. This can enhance the molecule's ability to interact with the membrane through π-π stacking interactions. The presence of an acetyl group on the pyrrole ring can also increase the molecule's lipophilicity, which may improve its permeability.

4. **Ethyl and Methyl Substituents**: The ethyl and methyl groups attached to the pyrrole ring increase the molecule's hydrophobic character. These groups can enhance the molecule's ability to traverse the lipid bilayer of the artificial membrane by increasing its lipophilicity.

5. **Acetylphenyl Group**: The acetylphenyl group contributes additional aromatic character and potential for hydrogen bonding through the acetyl group. This can enhance the molecule's interaction with the membrane, potentially increasing its permeability.

Overall, the given molecule has a combination of hydrophobic and hydrophilic features that suggest it may have moderate to high permeability in the PAMPA assay. The aromatic and lipophilic components can facilitate interaction with the membrane, while the polar groups can enhance solubility and interaction with the aqueous environment.

Final answer: High permeability

------
# 175

**SMILES:** COC1=CC2=C(C=C1)OC(=N2)NC3=NC(C4=C(N3)CCCC4=O)C5=C(C=NN5)Cl

**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 potential impact on permeability:

1. **Quinazoline Core**: The quinazoline moiety is a bicyclic structure that is relatively planar and aromatic. This can contribute to the molecule's ability to interact with the artificial membrane through π-π stacking interactions, which can enhance permeability. However, the presence of additional functional groups and heteroatoms can modify this effect.

2. **Chloro Substituent**: The chloro group on the quinazoline ring can increase the lipophilicity of the molecule, potentially enhancing its ability to permeate the lipid-like environment of the artificial membrane. However, the presence of chlorine can also introduce steric hindrance, which might affect the overall permeability.

3. **Methoxy Group**: The methoxy group is an electron-donating group that can increase the molecule's polarity. This can improve solubility in aqueous environments, which is beneficial for permeability in PAMPA. However, its presence might also affect the molecule's ability to interact with the membrane.

4. **Benzoxazole and Pyrimidinylamino Moieties**: The benzoxazole and pyrimidinylamino groups introduce additional aromaticity and potential hydrogen bonding sites. The benzoxazole can enhance lipophilicity, while the pyrimidinylamino group can form hydrogen bonds with the membrane, potentially aiding in permeability. The combination of these groups can create a balance between hydrophilic and lipophilic properties, which is often desirable for good permeability.

5. **Tetrahydroquinazoline Ring**: The partially saturated tetrahydroquinazoline ring can provide some flexibility to the molecule, which might help it to adapt to the membrane structure. This flexibility can be beneficial for permeability, as it allows the molecule to fit into the membrane more effectively.

Overall, the given molecule has a combination of aromatic and heteroaromatic rings, along with functional groups that can interact with the artificial membrane. The balance of lipophilic and hydrophilic properties suggests that the molecule may have moderate permeability, with the potential for some flexibility and interaction with the membrane. Therefore, the final answer is:

Final answer: Low-to-moderate permeability.

------
# 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. 

Firstly, the presence of the urea group in the molecule is significant. Urea groups are known to form hydrogen bonds, which can enhance the molecule's interaction with the artificial membrane. This interaction can increase the permeability of the molecule through the membrane, as hydrogen bonding can facilitate the passage of the molecule across the membrane.

Additionally, the molecule contains a piperidine ring, which is a six-membered ring containing nitrogen. Piperidine rings are often found in pharmaceuticals and can enhance the lipophilicity of the molecule. This increased lipophilicity can improve the molecule's ability to permeate lipid membranes, such as the artificial membrane used in the PAMPA assay.

The molecule also features aromatic rings, specifically chlorinated phenyl groups. The presence of chlorine atoms on the phenyl rings can increase the molecule's lipophilicity and potentially enhance its ability to permeate the membrane. Chlorine atoms can also influence the electronic properties of the aromatic ring, which may affect the molecule's interaction with the membrane.

Overall, the combination of these structural features suggests that the given molecule likely exhibits high permeability in the PAMPA assay. The urea group, piperidine ring, and chlorinated phenyl groups all contribute to the molecule's ability to interact with and permeate the artificial membrane.

Final answer: High permeability.

------
# 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 pyridine derivative, which is a class of compounds known for their aromatic properties. The structure of the given molecule includes a pyridine ring, which is a six-membered aromatic ring containing one nitrogen atom. This nitrogen atom contributes to the molecule's basicity and ability to participate in hydrogen bonding, which can influence its permeability.

Additionally, the molecule contains a spirocyclic structure, specifically a spiro[4,5-dihydro-1,3,2λ6,2'-azaspiro[4,5]deca-2,7,9-triene] moiety. This spirocyclic system introduces rigidity and a unique three-dimensional shape to the molecule, which can affect how it interacts with the artificial membrane. The presence of multiple nitrogen atoms in the spirocyclic structure may also enhance the molecule's ability to form hydrogen bonds and interact with polar sites on the membrane.

The dimethyl groups attached to the pyridine ring can increase the lipophilicity of the molecule, potentially enhancing its ability to permeate through the lipid-like environment of the artificial membrane.

Overall, the combination of aromaticity, basicity, hydrogen bonding potential, and lipophilicity suggests that the given molecule may exhibit high permeability in the Parallel Artificial Membrane Permeability Assay (PAMPA).

Final answer: High permeability

------
# 178

**SMILES:** CC[S+](=O)(NC1=CC=CC=C1C(=O)NC2=NC(=CS2)C3=CC=CC=C3)[O-]

**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. 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 that 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 planar and can engage in hydrogen bonding and other non-covalent interactions, which may aid in permeation.

3. **Phenyl Group**: The phenyl group attached to the thiazole ring is another aromatic component that can enhance the molecule's lipophilicity. This can improve the ability of the molecule to traverse the lipid-rich environment of the artificial membrane.

4. **Ethylsulfonylamino Group**: This functional group introduces a polar sulfonyl moiety, which can increase the molecule's solubility in aqueous environments. However, the presence of the sulfonyl group can also introduce steric hindrance and may affect the overall permeability by limiting the molecule's ability to fit through the membrane pores.

Overall, the given molecule's combination of aromatic and heterocyclic components, along with polar functional groups, suggests that it may exhibit moderate permeability in the PAMPA assay. The balance between hydrophobic and hydrophilic interactions will dictate its ability to permeate the artificial membrane.

Final answer: Low-to-moderate permeability.

------
# 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. The structure of the molecule includes a hydroxyphenyl group, which is a phenyl ring with a hydroxyl group attached. This hydroxyl group can form hydrogen bonds, which may enhance the molecule's solubility and interaction with the membrane.

Additionally, the molecule contains an indole-2-one moiety, which is a bicyclic structure consisting of a benzene ring fused to a pyrrole ring with a ketone group. This structure is relatively planar and can participate in π-π interactions with the membrane, potentially increasing its permeability.

The presence of a methylene bridge connecting the hydroxyphenyl group to the indole-2-one moiety introduces a degree of rigidity and planarity to the molecule, which can facilitate its passage through the membrane by allowing it to maintain a favorable orientation.

Overall, the combination of these structural features suggests that the given molecule may exhibit high permeability in the PAMPA assay, as it is likely to interact favorably with the artificial membrane through hydrogen bonding, π-π interactions, and its planar conformation.

Final answer: High permeability.

------
# 180

**SMILES:** C1CC2=C(C(N=C(N2)NC3=NC4=CC=CC=C4O3)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 distinct structural features that influence its permeability in the PAMPA assay. Let's break down these features and their potential impact on permeability:

1. **Quinazoline Core**: The quinazoline moiety is a bicyclic structure that is relatively planar and aromatic. This core can enhance the molecule's ability to interact with the artificial membrane through π-π stacking interactions, which are common in aromatic systems. This can contribute to moderate to high permeability.

2. **Chloro Substituent**: The presence of a chlorine atom on the quinazoline ring can increase the lipophilicity of the molecule. Chlorine is a halogen that can enhance the molecule's ability to penetrate lipid membranes, potentially increasing permeability.

3. **Benzoxazole Group**: The benzoxazole moiety is another aromatic system that can contribute to the molecule's overall lipophilicity and ability to interact with the membrane. The presence of nitrogen and oxygen in the heterocyclic ring can also form hydrogen bonds, which may aid in membrane interaction.

4. **Pyrimidinylamino Linkage**: The pyrimidine ring is a heterocyclic aromatic compound that can enhance the molecule's ability to form hydrogen bonds and engage in polar interactions with the membrane. The amino linkage provides flexibility and can facilitate the molecule's orientation and binding to the membrane.

5. **Tetrahydroquinazolinone Structure**: The partially saturated quinazolinone ring introduces some flexibility to the molecule, which can affect its ability to fit into the membrane's structure. The presence of a carbonyl group in the quinazolinone can also participate in hydrogen bonding, potentially aiding in membrane permeation.

Overall, the given molecule's combination of aromatic systems, halogen substitution, and heterocyclic components suggests that it has a balance of hydrophobic and polar characteristics. These features likely contribute to moderate to high permeability in the PAMPA assay, allowing the molecule to effectively interact with the artificial membrane.

Final answer: High permeability

------
# 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:** 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 potential impact on permeability:

1. **Benzoxazole Ring**: The presence of a benzoxazole moiety, which is a fused heterocyclic structure containing both nitrogen and oxygen, can contribute to the molecule's ability to interact with the artificial membrane. This ring system is relatively planar and aromatic, which can enhance the molecule's ability to penetrate lipid membranes due to its hydrophobic character.

2. **Pyridine Ring**: The pyridine ring is another aromatic heterocycle that can increase the molecule's lipophilicity. The nitrogen atom in the pyridine ring can participate in hydrogen bonding, which may affect the molecule's interaction with the membrane and its solubility in the assay environment.

3. **Nitro Group**: The nitro group is an electron-withdrawing group that can influence the electronic properties of the molecule. It can also affect the molecule's polarity and solubility, potentially reducing its permeability due to increased hydrophilicity.

4. **Amide Linkage**: The amide group is a polar functional group that can form hydrogen bonds. This can enhance the molecule's solubility in aqueous environments, but it may also hinder permeability through the membrane due to its polar nature.

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 interact with the lipid bilayer.

Overall, the given molecule contains a combination of hydrophobic and hydrophilic elements, which suggests that its permeability will be moderate. The aromatic rings and heterocycles contribute to lipophilicity, while the nitro and amide groups introduce polar characteristics. These features together suggest that the molecule will have a balance of solubility and membrane interaction, leading to a moderate permeability in the PAMPA assay.

Final answer: Low-to-moderate permeability.

------
# 182

**SMILES:** CN(C1=CC=CC=C1)C(=O)CSC2=NC3=C(CCCC3)C(=O)N2

**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.

Firstly, the molecule contains a quinazoline moiety, which is a bicyclic structure consisting of a benzene ring fused to a pyrimidine ring. This structure is known for its planar aromatic characteristics, which can facilitate interactions with the artificial membrane through π-π stacking and hydrophobic interactions. The presence of a carbonyl group in the quinazoline ring introduces a polar site, which can form hydrogen bonds with the membrane, potentially enhancing permeability.

Additionally, the molecule has a thioether linkage, indicated by the'sulfanyl' group. Thioethers are generally non-polar and can contribute to the lipophilicity of the molecule, enhancing its ability to traverse lipid membranes.

The N-methyl-N-phenylacetamide portion of the molecule introduces an amide group, which is polar and can participate in hydrogen bonding. This group can also contribute to the molecule's solubility and interaction with the membrane, potentially affecting permeability.

Overall, the combination of aromatic, polar, and non-polar features in the given molecule suggests that it may exhibit moderate permeability in the PAMPA assay. The aromatic and lipophilic components can facilitate membrane interaction, while the polar groups can enhance solubility and specific interactions with the membrane.

Final answer: Low-to-moderate 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 includes several functional groups and structural features that influence its permeability in the PAMPA assay. Let's break down these features to understand its permeability:

1. **Benzothiazine Core**: The molecule contains a benzothiazine core, which is a bicyclic structure consisting of a benzene ring fused to a thiazine ring. This core is relatively planar and aromatic, which can facilitate interactions with the artificial membrane through π-π stacking and hydrophobic interactions. Such interactions are common in molecules with aromatic systems, contributing to moderate to high permeability.

2. **Bromo Substituent**: The presence of a bromine atom on the phenyl ring can increase the molecule's lipophilicity. Bromine is a relatively large halogen, and its presence can enhance the molecule's ability to penetrate lipid membranes by increasing its hydrophobic character. This can contribute to higher permeability.

3. **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, it can also facilitate interactions with the membrane, potentially enhancing permeability.

4. **Methyl Group**: The methyl group attached to the benzothiazine core adds to the hydrophobic character of the molecule. This can further enhance the molecule's ability to interact with the lipid components of the artificial membrane, potentially increasing permeability.

Overall, the given molecule's combination of aromatic rings, a bromine substituent, and polar functional groups suggests that it would exhibit moderate to high permeability in the PAMPA assay. The balance of hydrophobic and hydrophilic interactions allows it to effectively traverse the artificial membrane.

Final answer: High permeability

------
# 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 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 benzamide moiety, which is a benzene ring linked to an amide group. This structure can contribute to the molecule's ability to permeate biological membranes due to the planar nature of the benzene ring, which can facilitate passage through lipid bilayers.

Additionally, the molecule contains a thiazole ring, which is a five-membered ring containing both sulfur and nitrogen. Thiazole rings are often found in bioactive compounds and can enhance the molecule's ability to bind to specific biological targets due to their aromaticity and electron-rich nature.

The presence of a methoxy group on the phenyl ring can also influence the molecule's permeability. Methoxy groups are electron-donating, which can increase the lipophilicity of the molecule, potentially enhancing its ability to permeate lipid membranes.

Overall, the combination of these functional groups suggests that the given molecule may have moderate to high permeability in the PAMPA assay, as the sulfonamide group, thiazole ring, and methoxy group collectively contribute to its ability to interact with and permeate biological membranes.

Final answer: High permeability.

------
# 185

**SMILES:** C1=CC=C2C(=C1)C(=NC(=N2)C3=CC=NC=C3)NC4=CC=NN4

**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. 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 ability to interact with various biological targets, often contributing to the molecule's pharmacological properties.

The molecule also features a pyridinyl group attached to the quinazoline core. Pyridine rings are aromatic and can enhance the molecule's ability to interact with biological membranes due to their planar structure and electron-rich nature, which can facilitate interactions with lipid bilayers.

Additionally, the molecule contains a pyrazolyl group linked to the quinazoline core. Pyrazole rings are five-membered heterocycles containing two nitrogen atoms, which can contribute to the molecule's ability to form hydrogen bonds and engage in π-π stacking interactions. This can further influence the molecule's permeability by enhancing its ability to traverse biological membranes.

Overall, the combination of these aromatic and heterocyclic groups in the given molecule suggests that it may have moderate to high permeability in the PAMPA assay. The presence of multiple aromatic systems and heteroatoms can facilitate interactions with the artificial membrane, potentially allowing the molecule to pass through with relative ease.

Final answer: High permeability

------
# 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:** 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 2-methylphenylsulfonylamino group, is likely to increase the molecule's hydrophilicity. This can enhance its ability to permeate through biological membranes, as the sulfonamide group can form hydrogen bonds with the membrane, facilitating transport.

2. **Aromatic Rings**: The molecule contains multiple aromatic rings, including a phenyl ring and a pyridine ring. Aromatic rings can increase the lipophilicity of the molecule, which may enhance its ability to permeate lipid membranes. However, the balance between hydrophilicity and lipophilicity is crucial for permeability.

3. **Thiazole Ring**: The thiazole ring is a heterocyclic compound that can contribute to the molecule's overall stability and ability to interact with biological targets. The presence of this ring may also influence the molecule's electronic properties, which can affect its permeability.

4. **Carboxamide Group**: The carboxamide group can participate in hydrogen bonding, which may aid in the molecule's interaction with the artificial membrane. This group can also contribute to the overall polarity of the molecule, potentially enhancing its permeability.

Overall, the given molecule's combination of hydrophilic and lipophilic groups suggests that it may have moderate permeability in the PAMPA assay. The sulfonamide group and aromatic rings contribute to its ability to interact with the membrane, while the thiazole and carboxamide groups may enhance its stability and polarity, respectively.

Final answer: Low-to-moderate permeability.

------
# 187

**SMILES:** C1=CC(=C(C=C1NC2=NC(=NC=C2)C3=CC=NC=C3)F)F

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a pyridine derivative with a difluorophenyl group and a pyridinylamino group. 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 rings in the structure can also contribute to the molecule's ability to permeate through membranes, as they are relatively planar and can participate in π-π stacking interactions with the lipid bilayer.

The amine group attached to the pyridine ring can form hydrogen bonds, which may aid in the molecule's solubility and permeability. However, the overall size and complexity of the molecule, along with the presence of multiple aromatic rings, might limit its permeability due to steric hindrance and potential interactions with the artificial membrane.

Considering these structural features, the given molecule is likely to have moderate permeability in the PAMPA assay, as the balance between hydrophobic and hydrophilic interactions, along with steric factors, will dictate its passage through the artificial membrane.

Final answer: Low-to-moderate permeability.

------
# 188

**SMILES:** C1CC(C2=C(C1)C3=C(N2)C(=CC=C3)Cl)NC(=O)C4=CC5=C(C=C4)OCO5

**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 to understand its permeability.

1. **Carbazole Moiety**: The molecule contains a tetrahydrocarbazole structure, which is a partially saturated derivative of carbazole. This moiety is known for its planar aromatic structure, which can facilitate interactions with the artificial membrane. The presence of the chlorine atom on the carbazole ring can enhance lipophilicity, potentially increasing the molecule's ability to permeate the membrane.

2. **Benzodioxole Ring**: The benzodioxole group is a bicyclic structure that contributes to the molecule's aromatic character. This group can enhance the molecule's ability to interact with the membrane through π-π stacking interactions, which are common in aromatic systems. The presence of this group suggests that the molecule may have moderate to high permeability due to these interactions.

3. **Carboxamide Group**: The carboxamide functional 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 beneficial for permeability. However, the overall effect of the carboxamide group on permeability will depend on the balance between its polar nature and the lipophilic character of the rest of the molecule.

4. **Overall Structure**: The combination of aromatic rings and the carboxamide group suggests that the given molecule has a balance of hydrophobic and hydrophilic properties. This balance is often associated with moderate permeability in PAMPA assays, as the molecule can interact with both the membrane and the aqueous environment.

In summary, the given molecule is likely to exhibit moderate permeability in the PAMPA assay due to its balanced hydrophobic and hydrophilic properties, the presence of aromatic rings, and the functional groups that can form hydrogen bonds.

Final answer: Low-to-moderate permeability.

------
# 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.

Secondly, the 1,2-oxazole ring is a heterocyclic structure that can contribute to the molecule's overall stability and rigidity. This ring system may also play a role in the molecule's ability to interact with the membrane, potentially affecting its permeability.

Additionally, the hydroxyphenyl group introduces a polar functional group, which can form hydrogen bonds with the membrane or the surrounding environment. This can influence the molecule's solubility and permeability, potentially enhancing its interaction with the membrane.

The carboxamide group is another polar functional group that can participate in hydrogen bonding. This group can also affect the molecule's solubility and permeability, potentially facilitating its passage through the membrane.

Overall, the combination of lipophilic and polar functional groups in the given molecule suggests that it may have moderate permeability in the PAMPA assay. The balance of hydrophobic and hydrophilic interactions will determine its ability to traverse the artificial membrane.

Final answer: Low-to-moderate permeability.

------
# 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 sulfonamide group is a key functional group that can influence the molecule's solubility and permeability.

The presence of the 3,4-dichlorophenyl group suggests that the molecule has increased lipophilicity, which can enhance its ability to permeate lipid membranes. This group is known for its electron-withdrawing properties, which can also affect the molecule's overall polarity and, consequently, its permeability.

The ethylamino linkage connects the dichlorophenyl group to the rest of the molecule, providing a flexible chain that can help the molecule adapt to the membrane's structure, potentially increasing its permeability.

The 1,2-oxazole ring is a heterocyclic component that can contribute to the molecule's overall stability and rigidity. This ring can also influence the molecule's electronic properties, which may affect its interaction with the artificial membrane.

The benzenesulfonamide moiety is a key structural feature that can enhance the molecule's solubility in aqueous environments, which is important for its permeability. The sulfonamide group is known for its ability to form hydrogen bonds, which can facilitate interactions with the membrane and improve permeability.

Overall, the combination of these structural features suggests that the given molecule likely has high permeability in the artificial membrane, as it possesses a balance of lipophilic and hydrophilic properties that favor membrane permeation.

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:

1. **Aromatic Rings**: The presence of multiple aromatic rings, such as the pyridine and phenyl groups, contributes to the molecule's lipophilicity. Aromatic rings can enhance the ability of the molecule to traverse lipid membranes, which is crucial for oral bioavailability. These rings also facilitate π-π interactions with the aromatic residues in the receptor binding site.

2. **Heterocyclic Components**: The pyrimidine and oxetane rings introduce heteroatoms (nitrogen and oxygen) into the structure, which can form hydrogen bonds with amino acid residues in the receptor binding site. The oxetane ring, in particular, is a small, strained four-membered ring that can enhance the molecule's metabolic stability and permeability by reducing its overall size and increasing its rigidity.

3. **Methyl Substituents**: The methyl group attached to the pyridine ring can increase the molecule's lipophilicity, further enhancing its ability to permeate lipid membranes. This substituent may also play a role in fine-tuning the molecule's binding affinity and selectivity for the EGFR.

Overall, the combination of aromatic rings, heterocyclic components, and methyl substituents suggests that the given molecule has a high potential for oral bioavailability and permeability through biological membranes. This is consistent with its intended use as an orally available inhibitor 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:** 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 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 molecule also features a pyridinyl group attached to the quinazoline core. Pyridine rings are aromatic and can enhance the molecule's ability to interact with biological systems through hydrogen bonding and π-π stacking interactions. This can increase the molecule's overall stability and binding affinity to its target.

Additionally, the molecule contains a substituted phenyl ring with a fluoro and a methyl group. The presence of the fluoro group can significantly influence the molecule's lipophilicity and electronic properties. Fluorine is highly electronegative, which can affect the molecule's ability to permeate biological membranes by altering its polarity and potentially enhancing its metabolic stability.

The methyl group on the phenyl ring can increase the molecule's lipophilicity, which may improve its ability to traverse lipid membranes. However, the balance between hydrophilic and lipophilic properties is crucial for membrane permeability, and the specific positioning of these groups will determine the overall permeability of the molecule.

In the context of the Parallel Artificial Membrane Permeability Assay (PAMPA), the given molecule's structural features suggest that it may exhibit moderate permeability. The quinazoline core and pyridinyl group contribute to its ability to interact with the membrane, while the fluoro and methyl substitutions influence its lipophilicity and electronic properties. These factors collectively determine the molecule's permeability, potentially allowing it to pass through the artificial membrane with a balance of hydrophilic and lipophilic interactions.

Final answer: Low-to-moderate permeability.

------
# 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 typically used to predict the permeability of a molecule across biological membranes, which is crucial for drug absorption and bioavailability.

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 solubility. 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 flexible and relatively small size.

2. **Isoindole Moiety**: The isoindole structure is a bicyclic compound that can enhance the molecule's rigidity and planarity. This rigidity can affect the molecule's ability to interact with the artificial membrane, potentially reducing its permeability. However, the presence of the carbonyl group in the isoindole moiety may enhance hydrogen bonding interactions with the membrane, which could improve permeability.

3. **Carbonyl Groups**: The molecule contains multiple carbonyl groups, which are polar functional groups. These groups can form hydrogen bonds with the artificial membrane, potentially increasing the molecule's permeability. However, they can also introduce steric hindrance, which might limit permeability.

4. **Methyl Substituents**: The presence of a methyl group on the isoindole moiety can increase the hydrophobic character of the molecule. This hydrophobicity can enhance membrane permeability by facilitating interactions with the lipid bilayer of the artificial membrane.

Overall, the given molecule's structure suggests that it may have moderate to high permeability in the PAMPA assay. The balance of hydrophobic and hydrophilic interactions, along with the presence of flexible and rigid components, likely contributes to its predicted permeability profile.

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 member of carbazoles, which are known for their planar aromatic structures. This particular molecule features a tetrahydrocarbazole moiety, which is a partially saturated version of the carbazole ring system. This saturation introduces some flexibility and reduces the overall planarity compared to fully aromatic carbazole derivatives.

The presence of the trimethoxybenzamide group contributes to the molecule's lipophilicity due to the three methoxy groups attached to the benzene ring. These methoxy groups can enhance the molecule's ability to interact with lipid environments, potentially increasing its permeability through the artificial membrane.

The amide linkage in the molecule provides a polar functional group that can form hydrogen bonds, which may influence the molecule's interaction with the membrane. However, the overall structure, with its combination of aromatic and aliphatic components, suggests that the molecule's lipophilic character is predominant.

Considering these structural features, the given molecule is likely to exhibit high permeability through the artificial membrane, as the balance of lipophilic and polar characteristics supports membrane permeation.

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, which influence its permeability in the PAMPA assay. Let's break down the structural components and their potential 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. **Methanone Linkage**: The methanone group (a carbonyl group) is a polar functional group that can form hydrogen bonds. This can influence the molecule's solubility and permeability, as it may interact with the polar components of the artificial membrane.

3. **Pyrimidinyl Group**: The pyrimidine ring is a heterocyclic aromatic compound that can contribute to the molecule's overall stability and ability to interact with biological membranes. The presence of nitrogen atoms in the pyrimidine ring can also participate in hydrogen bonding and ionic interactions.

4. **Piperazine Ring**: The piperazine moiety is a flexible, nitrogen-containing heterocycle that can enhance the molecule's solubility and permeability. Piperazine rings are often used in drug design to improve pharmacokinetic properties, including absorption and distribution.

5. **Methoxyanilino Group**: The methoxy group attached to the aniline moiety can increase the lipophilicity of the molecule, which may enhance its ability to permeate the artificial membrane. The aniline group can also participate in hydrogen bonding, which may affect the molecule's interaction with the membrane.

Overall, the given molecule contains a combination of lipophilic and polar functional groups, which suggests that it may have moderate to high permeability in the PAMPA assay. The balance of these groups allows the molecule to interact with both the lipid and polar components of the artificial membrane, facilitating its passage through the membrane.

Final answer: High permeability

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# 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 presence of the imidazopyridine core suggests that the molecule has a planar and aromatic structure, which can facilitate interactions with the artificial membrane. The aromaticity of the rings contributes to the molecule's ability to engage in π-π stacking interactions with the membrane, potentially enhancing its permeability.

Additionally, the molecule has a methoxyphenyl group attached to the imidazopyridine core. 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 traverse the lipid-like environment of the artificial membrane, thus improving its permeability.

Overall, the combination of the imidazopyridine core and the methoxyphenyl substituent suggests that the given molecule likely exhibits high permeability in the Parallel Artificial Membrane Permeability Assay.

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 potential impact on permeability:

1. **Piperidine Ring**: The presence of a piperidine ring, a six-membered nitrogen-containing heterocycle, is a common feature in many bioactive compounds. Piperidine rings can enhance the molecule's ability to interact with biological membranes due to their basic nitrogen, which can form hydrogen bonds and ionic interactions with the membrane.

2. **Thiocarbocarbamide Group**: The thiocarbocarbamide moiety, which includes a sulfur atom, can contribute to the molecule's overall lipophilicity. Sulfur-containing groups can enhance membrane permeability by increasing the molecule's ability to penetrate lipid bilayers.

3. **Pyridine Ring**: The pyridine ring, a six-membered aromatic ring with a nitrogen atom, can also participate in hydrogen bonding and π-π interactions with the membrane. The presence of a pyridine ring can enhance the molecule's ability to interact with the membrane, potentially increasing permeability.

4. **Trifluoromethyl Group**: The trifluoromethyl group is a highly electronegative substituent that can increase the lipophilicity of the molecule. This group can enhance membrane permeability by increasing the molecule's ability to dissolve in lipid environments.

5. **Methylpyridine Substituent**: The methyl group attached to the pyridine ring can increase the molecule's hydrophobic character, which may further enhance its ability to permeate lipid membranes.

Overall, the given molecule contains several functional groups that contribute to its lipophilicity and ability to interact with biological membranes. The combination of these groups suggests that the molecule would have high permeability in the PAMPA assay, allowing it to effectively traverse the artificial membrane.

Final answer: High permeability

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# 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 membranes due to its polar nature.

The molecule contains a dimethoxyphenyl group, which is a phenyl ring substituted with two methoxy groups. These methoxy groups can increase the lipophilicity of the molecule, potentially enhancing its ability to permeate lipid membranes. The presence of these groups can also influence the electronic properties of the phenyl ring, which may affect the molecule's interaction with the artificial membrane.

Additionally, the molecule includes 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 may also play a role in its ability to permeate the membrane by providing additional sites for hydrogen bonding or other interactions.

Overall, the combination of the sulfonamide group, the dimethoxyphenyl moiety, and the thiazole ring suggests that the given molecule may exhibit moderate permeability in the PAMPA assay. The sulfonamide group provides a polar character that can facilitate interaction with the membrane, while the methoxy groups and thiazole ring may enhance lipophilicity and stability, respectively.

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:** 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.

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 ability to permeate biological membranes due to its aromatic nature and potential for hydrogen bonding.

Additionally, the presence of a chlorophenyl group indicates that the molecule has a hydrophobic aromatic ring, which can enhance its ability to interact with lipid bilayers, thus increasing its permeability.

The hydroxy group attached to the phenyl ring can form hydrogen bonds, which may also aid in membrane permeability by interacting with polar head groups of the membrane lipids or proteins.

Overall, the combination of these functional groups suggests that the given molecule likely has high permeability to the artificial membrane, as it possesses both hydrophobic and hydrophilic characteristics that facilitate interaction with the membrane.

Final answer: High permeability

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# 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.

The molecule contains a quinazoline core, which is a bicyclic aromatic system. This core is known for its planar structure, which can facilitate interactions with the artificial membrane, potentially enhancing permeability. The aromatic nature of the quinazoline ring can also contribute to lipophilicity, which is often associated with better membrane permeability.

Additionally, the molecule has a methoxy group attached to a pyridine ring. The presence of this methoxy group can increase the molecule's lipophilicity, which may enhance its ability to permeate the membrane. The pyridine ring itself is a heteroaromatic system, which can also contribute to the molecule's overall aromatic character and influence its interaction with the membrane.

The molecule also features a piperazine ring, which is a six-membered heterocyclic amine. Piperazine rings are known for their basicity and ability to form hydrogen bonds, which can affect the molecule's solubility and permeability. The presence of a methyl group on the piperazine ring can further influence the molecule's lipophilicity and steric properties, potentially affecting its permeability.

Overall, the combination of aromatic systems, heterocyclic rings, and functional groups such as methoxy and methyl groups suggests that the given molecule may exhibit high permeability in the PAMPA assay due to its potential for lipophilic interactions and hydrogen bonding capabilities.

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:** 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 to understand its permeability.

1. **Indazole Ring System**: The molecule contains an indazole moiety, which is a bicyclic structure consisting of a benzene ring fused to a pyrazole ring. This structure is relatively planar and aromatic, which can enhance the molecule's ability to interact with the artificial membrane through π-π stacking interactions. The presence of the indazole ring suggests that the molecule may have moderate to high permeability due to its aromatic nature.

2. **Phenyl Groups**: The molecule includes two phenyl groups, one attached to the indazole and another as part of the acetamide linkage. These phenyl groups contribute to the hydrophobic character of the molecule, which can facilitate its passage through the lipid-like environment of the artificial membrane. The phenyl groups can also participate in hydrophobic interactions with the membrane, enhancing permeability.

3. **Acetamide Linkage**: The acetamide group introduces a polar amide bond, which can form hydrogen bonds with the artificial membrane. This functional group can increase the molecule's solubility in aqueous environments, potentially aiding in its permeability. However, the presence of the phenyl group attached to the acetamide may reduce the overall polarity, balancing the molecule's hydrophobic and hydrophilic properties.

4. **Methylphenyl Substituent**: The methyl group on the phenyl ring adds to the hydrophobic character of the molecule, which can further enhance its permeability through the membrane. The methyl group can also influence the steric properties of the molecule, potentially affecting how it fits into the membrane.

Overall, the given molecule's combination of aromatic rings, hydrophobic groups, and polar functional groups suggests that it would exhibit high permeability in the PAMPA assay. The balance of hydrophobic and hydrophilic properties, along with the ability to form non-covalent interactions with the membrane, supports its potential for efficient passage through the artificial membrane.

Final answer: High permeability.

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# 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:** 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 amide group contributes to the molecule's ability to form hydrogen bonds, which can enhance its interaction with the artificial membrane. This interaction is crucial for permeability, as it can facilitate the passage of the molecule through the membrane.

Additionally, the molecule contains a pyridine ring, which is a nitrogen-containing aromatic ring. The nitrogen atom in the pyridine ring can participate in hydrogen bonding and can also influence the molecule's electronic properties, potentially affecting its permeability.

The presence of a methoxy group on the phenyl ring can increase the molecule's lipophilicity, which may enhance its ability to permeate the membrane by increasing its solubility in the lipid bilayer.

The bromophenyl group introduces a bulky and electron-withdrawing substituent, which can affect the molecule's overall shape and electronic distribution. This can influence the molecule's ability to fit into the membrane and its overall permeability.

Overall, the combination of these functional groups and structural features suggests that the given molecule may exhibit moderate permeability in the artificial membrane, balancing between hydrophilic and lipophilic interactions.

Final answer: Low-to-moderate permeability.

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# 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:** 1

**Correct:** 1

# Response:
The given molecule is a derivative of the pyridinecarboxamide class, which is known for its potential biological activity. To predict its permeability in the PAMPA assay, we need to consider the structural features of the molecule.

The molecule contains a bicyclic structure, specifically an azabicyclo[2.2.2]octane moiety. This bicyclic structure is rigid and can influence the molecule's ability to fit into the membrane pores, potentially enhancing its permeability. The presence of nitrogen atoms in the bicyclic structure can also contribute to hydrogen bonding, which may affect the molecule's interaction with the membrane.

Additionally, the molecule has a pyridine ring, which is a common pharmacophore in many bioactive compounds. Pyridine rings can enhance lipophilicity, which is a key factor in membrane permeability. The lipophilic nature of the pyridine ring can facilitate the passage of the molecule through the lipid bilayer of the artificial membrane.

The molecule also contains a pyrimidinyl group, which can participate in additional hydrogen bonding and π-π interactions with the membrane. This can further influence its permeability by stabilizing the interaction with the membrane.

The acetamide group in the molecule can also contribute to its permeability. Amide groups are polar and can form hydrogen bonds, which may enhance the molecule's solubility and interaction with the membrane.

Overall, the combination of these structural features suggests that the given molecule likely has high permeability in the PAMPA assay due to its lipophilic pyridine ring, the rigid and nitrogen-containing bicyclic structure, and the polar acetamide group.

Final answer: High permeability.

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# 204

**SMILES:** C1CCC(C(C1)C2C3=C(CCCC3=O)NC(=N2)NC4NC5CCCCC5S4)Cl

**Label:** 1

**Predi:** 1

**Correct:** 1

# 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 potential impact on 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-thiazino[3,2-a]pyrimidin Core**: This bicyclic structure includes both nitrogen and sulfur heteroatoms, which can introduce polar characteristics. The presence of these heteroatoms can form hydrogen bonds or ionic interactions with the artificial membrane, potentially affecting the permeability. The balance between hydrophobic and polar regions will determine the overall permeability.

3. **Tetrahydroquinoline Moiety**: This part of the molecule is a partially saturated aromatic system, which can contribute to the molecule's rigidity and planarity. The aromatic nature can facilitate π-π interactions with the membrane, while the tetrahydro aspect may reduce steric hindrance, allowing better passage through the membrane.

4. **Carbonyl Group**: The carbonyl group in the structure is a polar functional group that can engage in hydrogen bonding with the membrane. This can enhance the molecule's interaction with the polar head groups of the artificial membrane, potentially increasing permeability.

5. **Chirality**: The stereochemistry indicated by the (1S) configuration can influence the molecule's three-dimensional shape, affecting how it fits into the membrane. Stereochemistry can play a crucial role in the molecule's ability to permeate the membrane, as it may affect the orientation and interaction with the membrane.

Overall, the given molecule's combination of hydrophobic and polar features, along with its structural rigidity and stereochemistry, suggests that it may have a balanced permeability profile. The presence of both lipophilic and polar groups indicates that the molecule could interact favorably with the artificial membrane, potentially leading to high permeability. However, the exact permeability would depend on the specific nature and composition of the artificial membrane used in the PAMPA assay.

Final answer: High permeability

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# 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:** 1

**Correct:** 0

# Response:
The given molecule is a sulfonamide, which is a class of compounds known for their ability to permeate biological membranes. The sulfonamide group, characterized by the presence of a sulfonyl functional group attached to an amine, is a key feature that contributes to the molecule's permeability.

In the given molecule, the sulfonamide group is linked to a pyrimidinyl moiety, which is a heterocyclic aromatic compound. The presence of the pyrimidine ring can enhance the molecule's ability to interact with biological membranes due to its planar structure, which can facilitate passage through lipid bilayers.

Additionally, the molecule contains a phenyl group, which is a hydrophobic aromatic ring. This hydrophobic character can also aid in membrane permeability by allowing the molecule to interact with the lipid components of the membrane.

The presence of a thioether linkage (sulfanyl group) in the molecule can also influence its permeability. Thioethers are generally more lipophilic, which can enhance the ability of the molecule to traverse lipid membranes.

Overall, the combination of these functional groups suggests that the given molecule likely exhibits high permeability in the PAMPA assay, as it possesses both hydrophobic and hydrophilic characteristics that facilitate interaction with the artificial membrane.

Final answer: High 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 benzamide derivative, which is a class of compounds known for their potential biological activity. The structure of the given molecule includes a benzamide moiety, which is a benzene ring attached to an amide group. This moiety is known to contribute to the molecule's ability to interact with biological targets, often through hydrogen bonding and hydrophobic interactions.

The molecule also contains a tetrahydro-1,3-benzothiazole ring system. This bicyclic structure includes a sulfur atom, which can influence the molecule's electronic properties and potentially its ability to permeate biological membranes. The presence of a sulfur atom can enhance the molecule's lipophilicity, which may facilitate its passage through lipid membranes.

Additionally, the tert-butyl group attached to the benzothiazole ring is a bulky hydrophobic moiety. This group can increase the molecule's overall hydrophobicity, which is often associated with improved membrane permeability. The tert-butyl group can also sterically hinder interactions with certain biological targets, potentially affecting the molecule's pharmacokinetic properties.

Overall, the combination of the benzamide moiety, the benzothiazole ring, and the tert-butyl group suggests that the given molecule may exhibit high permeability in the PAMPA assay due to its hydrophobic character and structural features that facilitate membrane interaction.

Final answer: High permeability.

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# 207

**SMILES:** C1=CN(C(=C1)C=C2C(=O)NC(=S)NC2=O)C3=CC=C(C=C3)O

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a member of the hydroxyphenyl compound family, which suggests the presence of a hydroxyl group attached to a phenyl ring. This hydroxyl group can form hydrogen bonds, which may enhance the molecule's solubility in water and potentially increase its permeability through the artificial membrane.

The molecule also contains a pyrrole ring, which is a five-membered heterocyclic compound with nitrogen. Pyrrole rings are known for their electron-rich nature, which can contribute to the molecule's ability to interact with the membrane through π-π interactions or hydrogen bonding.

Additionally, the molecule features a diazinane-dione structure, which is a six-membered ring containing two carbonyl groups. The presence of these carbonyl groups can increase the molecule's polarity, potentially enhancing its permeability by allowing it to form dipole-dipole interactions with the membrane.

The sulfanylidene group in the diazinane-dione ring introduces a sulfur atom, which can further contribute to the molecule's ability to form hydrogen bonds or coordinate with metal ions present in the membrane.

Overall, the combination of these functional groups suggests that the given molecule may exhibit moderate to high permeability through the artificial membrane due to its ability to form various non-covalent interactions with the membrane.

Final answer: High permeability.

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# 208

**SMILES:** C1COCCN1C2=NC=NC3=C2C=CC(=C3)NC(=O)C4=CC(=CC=C4)Br

**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 anticancer properties. The molecule contains several key structural features that influence its permeability.

Firstly, the quinazoline core is a bicyclic structure that contributes to the molecule's rigidity and planarity. This rigidity can enhance the molecule's ability to interact with biological membranes, as it can fit into membrane channels or interact with membrane proteins more effectively than flexible molecules.

Secondly, the presence of the morpholine ring, which is a heterocyclic amine, can increase the molecule's solubility in water. This is due to the presence of the oxygen and nitrogen atoms, which can form hydrogen bonds with water molecules. Increased solubility can enhance the molecule's ability to permeate biological membranes, as it can more easily dissolve in the aqueous environment of the membrane.

The bromine atom attached to the benzamide moiety can also play a role in the molecule's permeability. Halogen atoms like bromine can increase the lipophilicity of the molecule, which can enhance its ability to permeate lipid membranes. However, the presence of the bromine atom may also introduce steric hindrance, which could potentially limit the molecule's permeability.

Overall, the combination of the quinazoline core, the morpholine ring, and the bromine atom suggests that the given molecule may have moderate to high permeability in the PAMPA assay, as it possesses both hydrophilic and lipophilic characteristics that can facilitate membrane interaction.

Final answer: Low-to-moderate permeability.

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# 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:** 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 pyrimidine, pyrazole, and phenyl ring. Aromatic rings generally enhance lipophilicity, which can increase membrane permeability. However, the presence of these rings also suggests potential interactions with the membrane, which can either facilitate or hinder permeation depending on the specific interactions.

2. **Fluorine Substitution**: The presence of a fluorine atom on the pyrimidine ring can significantly affect the molecule's electronic properties. Fluorine is highly electronegative, which can increase the molecule's overall lipophilicity and potentially enhance its ability to permeate the membrane. Additionally, fluorine can influence the molecule's metabolic stability, which may indirectly affect permeability.

3. **Trifluoromethyl Group**: The trifluoromethyl group attached to the pyrazole ring is another lipophilic moiety that can enhance the molecule's permeability. This group is known for increasing the metabolic stability of compounds, which can prolong the molecule's presence in the biological environment, potentially enhancing its permeability.

4. **Amine Group**: The presence of an amine group in the pyrazole ring can introduce hydrogen bonding capabilities, which may facilitate interactions with the membrane or other molecules. This can either enhance or reduce permeability depending on the specific interactions.

5. **Pyridine Ring**: The pyridine ring contributes to the molecule's aromatic character and can also participate in hydrogen bonding due to the nitrogen atom. This can affect the molecule's solubility and permeability, potentially increasing it due to favorable interactions with the membrane.

Overall, the given molecule's structure suggests that it has a balance of lipophilic and polar characteristics, which can contribute to moderate permeability in the PAMPA assay. The presence of fluorine and trifluoromethyl groups likely enhances lipophilicity, while the amine and pyridine groups may facilitate specific interactions with the membrane. These factors collectively suggest that the molecule may exhibit moderate to high permeability in the PAMPA assay.

Final answer: Low-to-moderate 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 molecules, such as enzymes or receptors. This functional group can also enhance the molecule's solubility in aqueous environments, facilitating its transport across biological membranes.

Overall, the combination of these structural features suggests that the given molecule likely has high permeability in the PAMPA assay, as it possesses a balance of hydrophilic and lipophilic properties, as well as functional groups that can interact favorably with the artificial membrane.

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 certain pharmacological properties, such as acting on the central nervous system.

The molecule also contains a thiazole ring, which is a five-membered ring containing both sulfur and nitrogen atoms. This heterocyclic component can contribute to the molecule's ability to interact with biological targets, potentially enhancing its binding affinity and specificity.

Additionally, the presence of a dimethylamino group attached to a phenyl ring suggests that the molecule may have increased lipophilicity, which can influence its ability to cross lipid membranes. This group can also participate in hydrogen bonding and ionic interactions, which may affect the molecule's solubility and permeability.

Overall, the combination of these structural features suggests that the given molecule may have moderate permeability in the PAMPA assay, as the balance of hydrophilic and lipophilic properties can facilitate its passage through the artificial membrane. 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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# 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 hydrogen bonding and π-π interactions, which can affect the molecule's ability to interact with the artificial membrane. The presence of nitrogen atoms in the rings can also contribute to hydrogen bonding, potentially enhancing permeability.

2. **Methyl Substituents**: The given molecule has methyl groups attached to the pyrazolo[1,5-a]pyrimidine core and the phenyl rings. These methyl groups increase the hydrophobic character of the molecule, which can enhance its ability to permeate lipid membranes by increasing its lipophilicity.

3. **Phenyl Groups**: The molecule contains two phenyl rings, one of which is substituted with a chlorine atom. The phenyl rings contribute to the overall hydrophobicity and can facilitate interactions with the lipid components of the artificial membrane. The presence of a chlorine atom can also influence the electronic properties of the phenyl ring, potentially affecting the molecule's binding affinity to the membrane.

4. **Carboxamide Groups**: The presence of two carboxamide groups introduces polar characteristics to the molecule. These groups can form hydrogen bonds with the artificial membrane, potentially enhancing permeability by stabilizing interactions with the membrane.

5. **N-Methyl Substitution**: The N-methyl group on the carboxamide can further increase the hydrophobicity of the molecule, which may enhance its permeability through the lipid-rich artificial membrane.

Overall, the given molecule's combination of hydrophobic and polar functional groups suggests that it would have moderate to high permeability in the PAMPA assay. The balance of hydrophobic and polar interactions with the artificial membrane would facilitate its passage, making it suitable for further drug development studies.

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 to understand its permeability characteristics.

1. **Aromatic Rings**: The molecule contains multiple aromatic rings, including a phenyl ring substituted with bromo and chloro groups, and another phenyl ring with a methyl group. Aromatic rings generally contribute to lipophilicity, which can enhance membrane permeability due to their ability to interact with lipid bilayers.

2. **Halogen Substituents**: The presence of bromo and chloro substituents on the phenyl ring increases the molecule's lipophilicity. Halogen atoms can enhance membrane permeability by increasing the molecule's ability to penetrate lipid membranes, as they can form favorable interactions with the lipid bilayer.

3. **Cyclohexyl Group**: The cyclohexyl group is a non-aromatic, hydrophobic moiety that can increase the lipophilicity of the molecule. This can enhance the molecule's ability to traverse lipid membranes, contributing to higher permeability.

4. **Pyrazole Ring**: The pyrazole ring is a heterocyclic aromatic compound that can contribute to the molecule's overall stability and rigidity. While pyrazole rings can be involved in hydrogen bonding, their aromatic nature can also enhance lipophilicity, aiding in membrane permeability.

5. **Carboxamide Group**: The carboxamide group is a polar functional group that can participate in hydrogen bonding. This group can enhance solubility in aqueous environments, which might affect the overall permeability. However, its presence in conjunction with the other lipophilic groups may balance the molecule's permeability characteristics.

Overall, the given molecule's structure suggests that it has a balance of lipophilic and polar characteristics. The aromatic rings and halogen substituents likely contribute to high permeability through lipid membranes, while the carboxamide group may provide some solubility and interaction with aqueous environments. Therefore, the given molecule is likely to exhibit high permeability in the PAMPA assay.

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 with several functional groups and structural features that influence its permeability in the PAMPA assay. Let's break down the key components and their potential impact on permeability:

1. **Thienopyridine Core**: The thienopyridine structure is a bicyclic system that combines a thiophene ring with a pyridine ring. 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. The presence of nitrogen in the pyridine ring can also contribute to hydrogen bonding, potentially increasing permeability.

2. **Aromatic Substituents**: The molecule contains a 2-chloro-6-methoxyphenyl group. The chloro substituent can increase lipophilicity, which generally enhances membrane permeability. The methoxy group can also contribute to lipophilicity and may participate in hydrogen bonding, further influencing permeability.

3. **Carbamoyl Group**: The carbamoyl linkage (a carbonyl group adjacent to an amine) is polar and can form hydrogen bonds. This group may enhance the molecule's solubility in aqueous environments, which is beneficial for permeability in the PAMPA assay.

4. **Methoxy Group**: The methoxy group on the phenyl ring can increase lipophilicity and may also participate in hydrogen bonding, which can affect the molecule's interaction with the membrane.

5. **Methylthio Group**: The presence of a methylthio group can increase lipophilicity and may also contribute to the molecule's overall stability and interaction with the membrane.

6. **Ester Group**: The ethyl ester group is a common feature in many drug molecules and can enhance lipophilicity. However, esters can also be hydrolyzed, which might affect the molecule's stability in the PAMPA assay.

Overall, the given molecule has a combination of aromatic, polar, and lipophilic features that suggest it may have moderate to high permeability in the PAMPA assay. The balance of hydrophilic and lipophilic groups, along with the potential for hydrogen bonding and π-π interactions, likely facilitates its passage through the artificial membrane.

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 pharmaceuticals due to their basicity and ability to enhance the solubility and permeability of compounds.

The presence of a chlorophenyl group attached to the benzimidazole core introduces a lipophilic character, which can influence the molecule's ability to permeate lipid membranes. The chlorophenyl group can enhance the molecule's hydrophobic interactions with the lipid bilayer, potentially increasing its permeability.

Overall, the combination of the benzimidazole core, piperidine moiety, and chlorophenyl group suggests that the given molecule may exhibit moderate to high permeability in the PAMPA assay, as these structural features are commonly associated with favorable membrane permeability.

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:** 1

**Correct:** 1

# Response:
The given molecule is characterized by a 1,3-oxazole ring, which is a five-membered heterocyclic compound containing both oxygen and nitrogen atoms. This ring is known for its stability and ability to participate in hydrogen bonding, which can influence the molecule's interaction with the artificial membrane.

Attached to the oxazole ring is a dichlorophenyl group. The presence of two chlorine atoms on the phenyl ring increases the molecule's lipophilicity, which can enhance its ability to permeate through lipid membranes. Chlorine atoms can also contribute to the molecule's overall electronic properties, potentially affecting its interaction with the membrane.

Additionally, the molecule contains a methylamino group attached to the oxazole ring. This group introduces a basic nitrogen atom, which can form hydrogen bonds and potentially interact with acidic or polar sites on the artificial membrane. The presence of this group can also influence the molecule's solubility and permeability.

Finally, the carbonitrile group is a polar functional group that can engage in dipole-dipole interactions with the membrane. This group can also affect the molecule's overall polarity and solubility, which are important factors in determining permeability.

Overall, the combination of these functional groups suggests that the given molecule may exhibit moderate to high permeability in the PAMPA assay, as it possesses both lipophilic and polar characteristics that facilitate interaction with the artificial membrane.

Final answer: High 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:** 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. **Aromatic Rings**: The molecule contains multiple aromatic rings, including a pyrazole and a phenyl group. Aromatic rings can enhance lipophilicity, which generally 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 influencing the molecule's ability to interact with the membrane.

3. **Methoxy Linkage**: The methoxy group connecting the pyrazole and phenyl rings can increase the molecule's flexibility and solubility. This linkage may facilitate the molecule's passage through the membrane by allowing it to adopt conformations that better fit the membrane's structure.

4. **Thiazolidinedione Moiety**: The thiazolidinedione group is a heterocyclic structure that can contribute to the molecule's overall polarity. This group may interact with the membrane through hydrogen bonding or dipole interactions, potentially affecting permeability.

5. **Sulfone Group**: The presence of a sulfone group in the thiazolidinedione moiety introduces polarity and can enhance the molecule's solubility in aqueous environments. This group can also participate in hydrogen bonding, which may influence the molecule's interaction with the membrane.

Overall, the given molecule's combination of aromatic rings, fluorine substitution, methoxy linkage, thiazolidinedione moiety, and sulfone group suggests that it may have moderate to high permeability in the PAMPA assay. The balance of lipophilic and polar characteristics allows it to interact effectively with the artificial membrane, facilitating its passage.

Final answer: High 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:** 0

**Correct:** 0

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

The presence of multiple aromatic rings, such as the quinoline and phenyl groups, suggests that the molecule has a planar structure, which can facilitate interactions with the artificial membrane. Aromatic rings often participate in π-π stacking interactions, which can enhance the molecule's ability to permeate through the membrane.

The molecule also contains a chloro substituent on each of the phenyl rings. Chlorine atoms can increase the lipophilicity of the molecule, which generally enhances membrane permeability. However, the presence of a chloro group can also introduce steric hindrance, potentially affecting the molecule's ability to fit into the membrane pores.

The amino group attached to the phenyl ring can form hydrogen bonds with the membrane, which may either enhance or hinder permeability depending on the orientation and availability of the group. Amino groups can also increase the molecule's solubility in water, which might affect its permeability.

The methylimino group in the structure suggests the presence of a nitrogen atom that can participate in hydrogen bonding or other polar interactions, which may influence the molecule's permeability.

Overall, the given molecule's structure, with its aromatic rings, chloro substituents, and functional groups, suggests that it 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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# 219

**SMILES:** C1=CC(=CC(=C1)F)NC(=O)C2=CC(=NN2)C3=CC=CN3

**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 often associated with moderate to high permeability in biological membranes due to the presence of both hydrophilic and hydrophobic regions.

The molecule contains a pyrazole ring, which is a five-membered heterocyclic compound with two nitrogen atoms. This ring can contribute to the molecule's ability to form hydrogen bonds, enhancing its solubility and permeability.

Additionally, the molecule has a fluorophenyl group, which is a phenyl ring substituted with a fluorine atom. The presence of the fluorine atom can increase the lipophilicity of the molecule, potentially improving its ability to permeate lipid membranes.

The carboxamide group in the molecule is another key feature that can influence permeability. Amide groups are polar and can participate in hydrogen bonding, which may enhance the molecule's solubility in aqueous environments and its ability to permeate biological membranes.

Overall, the combination of these structural features suggests that the given molecule likely exhibits 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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# 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. The presence of these rings suggests that the molecule has a planar structure, which can facilitate interactions with the artificial membrane. The molecule contains a pyridine ring, which is known for its ability to participate in hydrogen bonding and dipole interactions, potentially enhancing its permeability.

Additionally, the indole moiety is a common structural motif in many bioactive compounds, and it can contribute to the molecule's ability to permeate biological membranes due to its hydrophobic character and potential for π-π stacking interactions.

The imidazo[1,2-a]pyridine component of the molecule is a bicyclic system that can enhance the molecule's rigidity and planarity, which may also aid in membrane permeability. This structural feature can facilitate the molecule's passage through the artificial membrane by allowing it to fit snugly within the membrane's lipid bilayer.

Overall, the combination of these aromatic and heterocyclic components suggests that the given molecule is likely to have high permeability in the Parallel Artificial Membrane Permeability 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 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.

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

1. **Benzoxazine Ring**: The presence of a benzoxazine moiety, which is a bicyclic structure containing both nitrogen and oxygen, can enhance the molecule's ability to interact with biological membranes. The aromatic nature of the benzoxazine ring can facilitate interactions with lipid bilayers, potentially increasing permeability.

2. **Chlorine Substitution**: The chloro group on the benzoxazine ring can influence the molecule's lipophilicity. Chlorine atoms are electronegative and can increase the overall hydrophobic character of the molecule, which may enhance its ability to permeate lipid membranes.

3. **Piperidine Ring**: The piperidine moiety is a saturated six-membered ring containing nitrogen. This structure is relatively flexible and can contribute to the molecule's overall conformational adaptability, which may affect its ability to permeate membranes.

4. **Carboxamide Linkage**: The carboxamide group is a polar functional group that can form hydrogen bonds with the membrane or surrounding environment. This can influence the molecule's solubility and permeability, potentially affecting its ability to cross the membrane.

5. **Isopropoxyphenyl Group**: The presence of an isopropoxy group attached to a phenyl ring 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's structure suggests that it may have moderate to high permeability in the PAMPA assay due to the presence of both hydrophobic and hydrophilic groups, as well as the ability to form hydrogen bonds and interact with lipid membranes.

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 significant role in its permeability characteristics. 

The core structure of the molecule is based on an indene-1-one framework, which is a bicyclic structure consisting of a benzene ring fused to a cyclopentenone. This core provides a planar and relatively rigid structure, which can facilitate interactions with the artificial membrane.

Attached to this core are two phenyl groups. One of these phenyl groups is substituted with a trifluoromethyl group, which is known for its electron-withdrawing properties. This substitution can increase the lipophilicity of the molecule, enhancing its ability to permeate through lipid membranes. The trifluoromethyl group can also influence the electronic distribution across the molecule, potentially affecting its interaction with the artificial membrane.

The other phenyl group is substituted with a methyl group, which is a small, non-polar substituent that can also contribute to the lipophilicity of the molecule. The presence of these aromatic rings and their substituents can facilitate π-π interactions with the artificial membrane, which is composed of lipophilic and hydrophilic regions.

Overall, the combination of the indene-1-one core, the trifluoromethyl group, and the methyl-substituted phenyl group suggests that the given molecule has a balance of hydrophobic and electronic properties that likely confer high permeability to the artificial 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:** 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 potential impact on 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 the artificial membrane. The aromaticity can facilitate π-π stacking interactions with the membrane, potentially increasing permeability.

2. **Pyridine Ring with Chlorine Substitution**: The presence of a chlorinated pyridine ring can influence the molecule's lipophilicity. Chlorine is an electronegative atom that can increase the molecule's overall hydrophobicity, which may enhance its ability to traverse lipid membranes. However, the chlorine atom can also introduce steric hindrance, which might affect the molecule's overall permeability.

3. **Pyrrolidine Moiety**: The pyrrolidine ring is a saturated, non-aromatic heterocycle that can increase the molecule's solubility in water. This feature might improve the molecule's ability to interact with the aqueous environment of the PAMPA assay, potentially enhancing its permeability.

4. **Methanone Linkage**: The carbonyl group in the methanone linkage can form hydrogen bonds with the artificial membrane, which might facilitate or hinder permeability depending on the orientation and availability of these groups.

Overall, the given molecule's structure suggests a balance between hydrophobic and hydrophilic properties, with aromatic and heterocyclic features that could enhance its interaction with the artificial membrane. The presence of the chlorinated pyridine and the imidazo[1,2-a]pyridine core likely contribute to moderate to high permeability, as these features can facilitate membrane interaction while the pyrrolidine moiety may enhance solubility.

Final answer: High 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 member of the phenazine family, which is known for its planar, aromatic structure. This particular molecule features a hydroxyl group attached to the phenazine core, which can influence its chemical properties and interactions with the artificial membrane.

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 the artificial membrane, which mimics biological membranes. The permeability is influenced by several factors, including the molecule's lipophilicity, size, and the presence of functional groups.

The phenazine core of the given molecule is a polycyclic aromatic compound, which generally contributes to lipophilicity. This can enhance the molecule's ability to interact with the lipid components of the artificial membrane, potentially increasing its permeability. However, the presence of the hydroxyl group introduces a polar character, which can form hydrogen bonds with the membrane or solvent, potentially affecting its permeability.

Overall, the balance between the lipophilic phenazine core and the polar hydroxyl group will dictate the permeability of the given molecule in the PAMPA assay. While the aromatic structure suggests a degree of lipophilicity, the hydroxyl group may moderate this effect, leading to a classification of low-to-moderate permeability.

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 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 molecule 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 how the molecule interacts with the artificial membrane.

Additionally, the molecule includes a thiazole ring, which is a five-membered ring containing both sulfur and nitrogen. Thiazole rings are often involved in hydrogen bonding and can contribute to the molecule's overall polarity. This can affect the molecule's solubility and permeability, as polar interactions with the membrane can either hinder or facilitate passage.

The combination of these functional groups suggests that the given molecule may have moderate permeability to the artificial membrane. The sulfonamide group, along with the methoxyphenyl and thiazole components, likely contribute to a balance of hydrophilic and lipophilic properties, which can influence its ability to permeate the membrane.

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 can increase the lipophilicity of the molecule. Lipophilicity is a crucial factor in membrane permeability, as it affects the molecule's ability to traverse lipid bilayers. The trifluoromethyl group can enhance the molecule's ability to interact with the hydrophobic regions of the artificial membrane, potentially increasing its permeability.

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 the molecule's passage through the membrane.

3. **Piperidine Ring**: The piperidine moiety is a saturated nitrogen-containing ring that can enhance the molecule's solubility and flexibility. This flexibility can allow the molecule to adapt its conformation to better fit the membrane, potentially increasing its permeability.

4. **Dihydropyrido[1,2-b][1,4]dazepin-6-one Core**: This bicyclic structure is a key component of the molecule. The presence of nitrogen atoms in this core can contribute to the molecule's ability to form hydrogen bonds or ionic interactions with the membrane. The rigidity of this core can also help maintain a specific conformation that may be favorable for permeation.

Overall, the given molecule's structural features suggest that it has a balance of lipophilic and hydrophilic properties, which is often desirable for good membrane permeability. The trifluoromethyl group increases lipophilicity, while the pyridine and piperidine rings provide opportunities for hydrogen bonding and ionic interactions. These factors 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 ability to permeate biological membranes due to its lipophilic nature. The presence of aromatic rings, such as the phenyl groups, contributes to its hydrophobic character, enhancing its ability to interact with lipid membranes. The fluorine atoms in the structure can also increase lipophilicity and membrane permeability by affecting the electronic distribution and potentially facilitating passage through the membrane.

The carbonyl group in the benzodiazepine ring system may also play a role in permeability, as it can form hydrogen bonds with the membrane, potentially aiding in its transport. Overall, the combination of aromatic rings, fluorine substituents, and the carbonyl group suggests that the given molecule likely exhibits high permeability in the PAMPA assay.

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, which is a class of compounds known for their diverse biological activities. The structure of the given molecule includes a pyrimidine ring, which is a six-membered heterocyclic aromatic ring containing two nitrogen atoms. This pyrimidine core is substituted with a piperidine ring and a phenyl group, which is further substituted with a dimethylamino group.

The presence of the pyrimidine ring suggests that the given molecule may have significant biological activity, as pyrimidines are often found in nucleotides and can interact with biological targets such as enzymes and receptors. The piperidine ring is a saturated six-membered ring containing nitrogen, which can enhance the molecule's solubility and bioavailability.

The dimethylamino group attached to the phenyl ring is an electron-donating group, which can influence the electronic properties of the molecule, potentially affecting its interaction with biological membranes. This group can also increase the molecule's lipophilicity, which may enhance its ability to permeate lipid membranes.

Overall, the combination of the pyrimidine core, piperidine ring, and dimethylamino group suggests that the given molecule may have moderate to high permeability in the PAMPA assay, as these structural features are commonly associated with good membrane permeability.

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. 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 phenyl ring, which is further substituted with a dichlorophenyl group. The presence of chlorine atoms on the phenyl ring can increase the lipophilicity of the molecule, potentially enhancing its ability to permeate lipid membranes. However, the dichlorophenyl group can also introduce steric hindrance, which might affect the molecule's overall permeability.

Additionally, the molecule contains a pyridinyl moiety linked through an acetamide bridge. The pyridine ring can contribute to the molecule's polarity and may affect its interaction with the artificial membrane. The acetamide linkage can also influence the molecule's solubility and permeability by providing a degree of flexibility and polarity.

Overall, the combination of these functional groups suggests that the given molecule may exhibit moderate permeability in the artificial membrane, balancing between lipophilicity and steric factors. 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.

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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 often involved in hydrogen bonding and can influence the molecule's solubility and permeability.

In the given molecule, the presence of the acetamido group suggests that it has polar characteristics, which can enhance its solubility in aqueous environments. This group can also participate in hydrogen bonding, which may facilitate interactions with the artificial membrane.

The molecule also contains a phenyl group, which is a hydrophobic aromatic ring. This group can interact with the hydrophobic regions of the artificial membrane, potentially enhancing permeability through van der Waals interactions.

Additionally, the thiophenyl group, which is a sulfur-containing heterocycle, can contribute to the molecule's overall electronic properties. This group can enhance the molecule's ability to interact with the membrane through π-π stacking or other non-covalent interactions.

The bromophenyl moiety introduces a halogen atom, which can increase the molecule's lipophilicity. This can affect the permeability by enhancing the molecule's ability to traverse lipid membranes.

Overall, the combination of polar and non-polar groups in the given molecule suggests that it may have moderate permeability to the artificial membrane. The balance of hydrophilic and hydrophobic interactions, along with the potential for hydrogen bonding and van der Waals interactions, likely contributes to its permeability characteristics.

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. This can enhance the molecule's ability to interact with the membrane, potentially increasing its permeability.

2. **Methyl Substituents**: The molecule contains methyl groups attached to the triazolopyridazine moiety. These small, non-polar groups can increase the lipophilicity of the molecule, which generally enhances membrane permeability by allowing the molecule to better interact with the lipid components of the membrane.

3. **Tetrahydropyrrolopyridine Moiety**: This part of the molecule includes a pyrrolo ring that is partially saturated, indicating the presence of hydrogen atoms that can participate in hydrogen bonding. The methyl group attached to this moiety also contributes to the lipophilicity of the molecule, which can further enhance its permeability.

4. **Benzonitrile Group**: The benzonitrile group is characterized by a benzene ring with a nitrile group (a carbon triple-bonded to nitrogen). The nitrile group is polar and can engage in dipole-dipole interactions with the membrane. However, the overall effect of this group on permeability is less clear and may depend on the balance between its polar nature and the overall lipophilicity of the molecule.

Overall, the given molecule exhibits a combination of polar and non-polar characteristics, with multiple nitrogen atoms and methyl groups contributing to its potential interactions with the artificial membrane. The balance of these features suggests that the molecule likely has high permeability in the PAMPA assay, as it can effectively interact with both the polar and non-polar components of the 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 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. **Benzimidazole Moiety**: The presence of the benzimidazole ring is significant as it is a heterocyclic aromatic compound. Benzimidazole is known for its ability to participate in hydrogen bonding and π-π stacking interactions. This can enhance the molecule's ability to interact with the artificial membrane, potentially increasing its permeability.

2. **Methoxy Group**: The methoxy group attached to the aromatic ring contributes to the molecule's lipophilicity. This can enhance the molecule's ability to traverse lipid membranes, which is a key factor in permeability.

3. **Fluorophenyl Group**: The fluorine atom in the fluorophenyl group 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.

4. **Nitrile Group**: The nitrile group is a polar functional group that can participate in hydrogen bonding. While it may introduce some polarity, its linear structure can also allow it to fit into the membrane's lipid bilayer, potentially facilitating permeation.

5. **Conjugated System**: The presence of a conjugated system, as indicated by the (E)-configuration, suggests that the molecule has a planar structure. This can enhance its ability to interact with the membrane through π-π interactions, potentially increasing permeability.

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 in PAMPA assays. The presence of the benzimidazole moiety, methoxy group, and fluorophenyl group likely contribute to its ability to interact with the artificial membrane, indicating that the molecule likely exhibits high permeability in the PAMPA assay.

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. This particular molecule features an acridinone core, which is a tricyclic structure consisting of two benzene rings fused to a pyridine ring, with a ketone group at one position. This core structure is known for its ability to intercalate with DNA, which is a key property for many acridine derivatives.

The presence of a chloro substituent on the acridine ring can influence the molecule's electronic properties, potentially affecting its interaction with biological membranes. Chlorine atoms can increase the lipophilicity of the molecule, which may enhance its ability to permeate lipid membranes.

Additionally, the molecule contains a diethylaminoethoxy side chain. This functional group is a tertiary amine, which can be protonated under physiological conditions, imparting a positive charge to the molecule. This positive charge can enhance the molecule's solubility in aqueous environments and may facilitate its interaction with negatively charged biological membranes.

The combination of the acridine core, chloro substituent, and diethylaminoethoxy side chain suggests that the given molecule may have moderate to high permeability through the artificial membrane. The planar aromatic structure of the acridine core allows for potential stacking interactions with lipid bilayers, while the charged side chain can enhance solubility and membrane interaction. These features collectively contribute to the molecule's ability to traverse the artificial membrane, indicating a potential for high permeability.

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 can facilitate interactions with the artificial membrane, potentially enhancing permeability due to favorable stacking interactions with the membrane's aromatic residues.

2. **Chloro Substituent**: The presence of a chlorine atom on the quinazoline ring can influence the molecule's lipophilicity. Chlorine is an electronegative atom that can increase the molecule's overall hydrophobicity, which may enhance its ability to permeate the lipid-like environment of the artificial membrane.

3. **Pyrimidinyl Group**: The pyrimidinyl group is a heterocyclic aromatic ring that can participate in hydrogen bonding and other polar interactions. This group may contribute to the molecule's ability to interact with the polar head groups of the artificial membrane, potentially aiding in permeability.

4. **Benzoxazole Moiety**: The benzoxazole ring is another aromatic system that can engage in π-π interactions with the membrane. Additionally, the presence of nitrogen and oxygen in the benzoxazole can form hydrogen bonds, which may further influence the molecule's interaction with the membrane.

5. **Tetrahydroquinazoline Structure**: The partially saturated tetrahydroquinazoline portion of the molecule introduces flexibility and a different three-dimensional shape compared to fully aromatic systems. This flexibility can allow the molecule to adapt its conformation to better fit the membrane's structure, potentially enhancing permeability.

Overall, the given molecule's combination of aromatic and heterocyclic components, along with its chloro substituent, suggests that it may exhibit high permeability in the PAMPA assay due to favorable interactions with the artificial membrane.

Final answer: High permeability

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# 235

**SMILES:** CNC1=NC=CC(=N1)C2=CC=CC3=CC=CC=C32

**Label:** 1

**Predi:** 1

**Correct:** 1

# 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, contributing to its ability to interact with biological membranes.

The presence of the pyrimidine ring in the given molecule is significant as it is a nitrogen-containing heterocycle. Pyrimidine rings are often involved in hydrogen bonding and can enhance the molecule's ability to interact with polar environments, such as those found in biological membranes.

The N-methyl group attached to the pyrimidine ring can increase the lipophilicity of the molecule, potentially enhancing its ability to permeate lipid membranes. This modification can also affect the molecule's overall steric properties, influencing how it fits into the membrane.

Overall, the combination of the quinoline moiety and the pyrimidine ring, along with the N-methyl group, suggests that the given molecule may have a favorable interaction with the artificial membrane, leading to a classification of high permeability in the PAMPA assay.

Final answer: High permeability.

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# 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:** 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 to understand its permeability:

1. **Dimethoxyphenyl Group**: The presence of the dimethoxyphenyl group, which is a phenyl ring substituted with two methoxy groups, contributes to 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.

2. **Cyclopenta[b]chromene Core**: This core structure is a fused ring system that includes both aromatic and non-aromatic components. The aromatic nature of the chromene ring can facilitate interactions with the lipid bilayer of the artificial membrane, enhancing permeability. However, the rigidity and size of the fused ring system may also limit permeability due to steric hindrance.

3. **Morpholine Group**: The morpholine moiety is a heterocyclic amine that can enhance the molecule's solubility in water. This group can form hydrogen bonds with the artificial membrane, potentially increasing permeability. Additionally, the presence of a flexible alkyl chain connecting the morpholine to the core structure allows for some degree of conformational flexibility, which can aid in permeation.

4. **Dione Functional Groups**: The presence of two carbonyl groups (dione) in the cyclopenta[b]chromene core can participate in hydrogen bonding and dipole-dipole interactions with the artificial membrane. These interactions can enhance permeability, but the overall effect depends on the balance with other hydrophilic and hydrophobic interactions.

Overall, the given molecule exhibits a combination of lipophilic and hydrophilic properties due to its aromatic rings, methoxy groups, and morpholine moiety. These features suggest that the molecule has a balanced permeability profile, likely resulting in moderate permeability in the PAMPA assay. The balance between lipophilicity and hydrophilicity, along with the structural rigidity and flexibility, contribute to its ability to traverse the artificial membrane.

Final answer: Low-to-moderate 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:** 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. 

The core structure of the molecule is based on an indene-1-one framework, which is a bicyclic structure consisting of a benzene ring fused to a cyclopentenone. This core provides a certain degree of rigidity and planarity, which can facilitate interactions with the artificial membrane.

Attached to this core are two phenyl groups. One of these phenyl groups is substituted with a trifluoromethyl group. The trifluoromethyl group is highly electronegative and can increase the lipophilicity of the molecule, enhancing its ability to permeate through the lipid-like environment of the artificial membrane.

The other phenyl group is substituted with an anilino group, which is an amino group attached to a phenyl ring. The presence of the anilino group can introduce hydrogen bonding capabilities, which may affect the molecule's interaction with the membrane. However, the anilino group is also relatively polar, which could reduce the overall lipophilicity of the molecule.

Overall, the given molecule has both lipophilic and polar characteristics due to its trifluoromethyl and anilino groups, respectively. The balance of these properties suggests that the molecule would exhibit moderate permeability in the PAMPA assay, as it can interact with both the hydrophobic and hydrophilic components of the artificial membrane.

Final answer: Low-to-moderate permeability.

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# 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 derivative of quinoline, which is a bicyclic compound consisting of a benzene ring fused to a pyridine ring. This 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 2-chlorophenyl group attached to the quinoline moiety introduces a chlorine atom, which can enhance the lipophilicity of the molecule. This increased lipophilicity can improve the molecule's ability to interact with lipid membranes, potentially increasing its permeability.

Additionally, the molecule contains a diethylamino group, which is a common feature in many pharmacologically active compounds. This group can contribute to the molecule's overall basicity and solubility, which may affect its permeability by influencing its interaction with the membrane's lipid bilayer and its ability to traverse it.

The overall structure, with its combination of aromatic rings, chlorine substitution, and amino groups, suggests that the given molecule may have moderate to high permeability in the PAMPA assay. The balance of hydrophobic and hydrophilic properties, along with the planar aromatic system, likely facilitates its passage through 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:** 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 sulfonamide group is attached to a thiophene ring, which is a five-membered aromatic ring containing sulfur. Thiophene rings are known for their electron-rich nature, which can enhance the molecule's ability to penetrate lipid membranes due to increased hydrophobic interactions.

Additionally, the molecule contains a phenyl group, which is a benzene ring, and a bromophenyl group, which is a benzene ring substituted with a bromine atom. The presence of these aromatic rings can further increase the molecule's lipophilicity, enhancing its ability to permeate through lipid membranes.

The acetamide linkage in the molecule provides a degree of flexibility and polarity, which can also influence the molecule's permeability by allowing it to interact with both hydrophilic and hydrophobic environments.

Overall, the combination of the sulfonamide group, thiophene ring, and aromatic groups suggests that the given molecule likely has high permeability to the artificial membrane, as these structural features enhance its ability to interact with and penetrate lipid bilayers.

Final answer: High 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:** 1

**Correct:** 1

# Response:
The given molecule is a complex indole derivative, which is a member of the indolyl carboxylic acids. To predict its permeability in the PAMPA assay, we need to consider the structural features that influence its interaction with the artificial membrane.

1. **Indole Core**: The indole structure is a bicyclic compound consisting of a benzene ring fused to a pyrrole ring. This core is relatively planar and aromatic, which can facilitate interactions with the membrane through π-π stacking and hydrophobic interactions. The presence of the indole core suggests that the molecule may have moderate to high permeability due to its aromatic nature.

2. **Carboxylic Acid Group**: The carboxylic acid moiety is a polar functional group that can form hydrogen bonds with the membrane. This group can increase the molecule's solubility in aqueous environments, which is beneficial for permeability. However, it can also introduce some degree of polarity, potentially limiting permeability through the membrane.

3. **Methoxy Group**: The methoxy group is an electron-donating group that can enhance the lipophilicity of the molecule. This can improve the molecule's ability to traverse the lipid bilayer of the artificial membrane, contributing to higher permeability.

4. **Phenyl and Cyclohexyl Groups**: The phenyl group, particularly with the ethenyl substitution, adds to the hydrophobic character of the molecule, which can enhance membrane permeability. The cyclohexyl group, being a non-aromatic, aliphatic ring, can also contribute to the hydrophobic interactions with the membrane, potentially increasing permeability.

5. **Pyrrolidine Ring**: The pyrrolidine ring is a secondary amine that can participate in hydrogen bonding and may affect the molecule's overall conformation. This can influence the molecule's ability to fit into the membrane's structure, potentially affecting permeability.

Overall, the given molecule's combination of aromatic and hydrophobic groups, along with polar functional groups, suggests that it may have moderate to high permeability in the PAMPA assay. The balance of hydrophobic and hydrophilic properties allows it to interact favorably with the artificial membrane, facilitating its passage.

Final answer: High permeability

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# 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 features several functional groups and structural elements that influence its permeability in the PAMPA assay. Let's break down these features to understand its permeability characteristics.

1. **Isoquinoline Core**: The molecule contains an isoquinoline core, which is a bicyclic structure consisting of a benzene ring fused to a pyridine ring. This core is relatively planar and aromatic, which can facilitate interactions with the artificial membrane through π-π stacking and hydrophobic interactions. The presence of this core suggests that the molecule may have moderate to high permeability due to its aromatic nature.

2. **Methoxy Groups**: The presence of two methoxy groups on the aromatic ring of the isoquinoline core increases the molecule's lipophilicity. Methoxy groups can enhance membrane permeability by increasing the molecule's ability to dissolve in lipid bilayers. This suggests that the given molecule may have high permeability due to these groups.

3. **Piperazine Ring**: The molecule includes a piperazine ring, which is a six-membered heterocyclic amine. Piperazine rings are known to increase the solubility and permeability of compounds due to their basic nitrogen atoms, which can form hydrogen bonds and ionic interactions with the membrane. This feature likely contributes to the molecule's permeability.

4. **Chlorophenyl Group**: The presence of a chlorophenyl group introduces additional hydrophobic character and potential for halogen bonding. The chlorine atom can participate in halogen bonding, which may enhance the molecule's interaction with the membrane. This group can also contribute to the overall lipophilicity of the molecule, potentially increasing its permeability.

5. **Carbonyl Group**: The carbonyl group in the molecule can participate in hydrogen bonding, which may facilitate interactions with the membrane. However, the presence of this group is counterbalanced by the overall lipophilic nature of the molecule, which is dominated by the aromatic and methoxy groups.

Overall, the given molecule's structure, characterized by its aromatic isoquinoline core, methoxy groups, piperazine ring, chlorophenyl group, and carbonyl group, suggests that it has high permeability in the PAMPA assay. The combination of hydrophobic and hydrophilic interactions, along with the ability to form hydrogen bonds and ionic interactions, supports its potential to permeate the artificial membrane efficiently.

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 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.

In the given molecule, the sulfonamide group is attached to a phenyl ring, which is a common structural motif that can increase lipophilicity. This lipophilic character can enhance the molecule's ability to permeate through lipid membranes, contributing to its permeability.

Additionally, the molecule contains a pyridine ring, which is a nitrogen-containing heterocycle. Pyridine rings can participate in hydrogen bonding and other interactions with the artificial membrane, potentially affecting the molecule's permeability.

The presence of a thiazole ring, another nitrogen and sulfur-containing heterocycle, can also influence the molecule's permeability. Thiazole rings are known for their ability to interact with various biological targets, which can impact the molecule's overall permeability.

The carboxamide group in the molecule can form hydrogen bonds, which may also play a role in its interaction with the artificial membrane.

Overall, the combination of these functional groups and structural motifs suggests that the given molecule may have moderate permeability in the PAMPA assay, as the sulfonamide group and other heterocycles can facilitate interactions with the membrane, while the phenyl and pyridine rings can enhance lipophilicity.

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 can enhance the molecule's ability to interact with the hydrophobic regions of the artificial membrane, potentially increasing its permeability.

2. **Chloro Substituent**: The chloro group on the benzodioxole ring can increase the molecule's lipophilicity, which may further enhance its permeability through the membrane by increasing its solubility in lipid environments.

3. **Piperidine Ring**: The piperidine moiety is a saturated nitrogen-containing heterocycle that can introduce basicity to the molecule. This basicity can facilitate interactions with the membrane through hydrogen bonding or ionic interactions, potentially aiding in permeability.

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 might not significantly hinder permeability unless the hydrolysis rate is high, which is not typically the case in short assays.

5. **Amino Group**: The presence of an amino group linked to the piperidine ring can enhance the molecule's ability to form hydrogen bonds with the membrane, potentially increasing its permeability.

Overall, the given molecule's combination of aromatic, lipophilic, and basic features suggests that it would exhibit high permeability in the PAMPA assay. The balance of hydrophobic and hydrophilic interactions, along with the potential for hydrogen bonding and ionic interactions, likely facilitates its passage through the artificial 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 several structural features.

The molecule contains an ethyl group attached to a phenyl ring, which is further substituted with ethoxy and methyl groups. These groups contribute to the molecule's lipophilicity, enhancing its ability to interact with the lipid components of the artificial membrane. The presence of these groups suggests that the molecule may have moderate to high permeability due to increased hydrophobic interactions.

Additionally, the molecule features a pyridine ring, which can participate in hydrogen bonding and other polar interactions. The pyrrolopyridine core is a bicyclic structure that can provide rigidity and planarity, potentially facilitating passage through the membrane by allowing the molecule to fit snugly within the membrane's structure.

The carboxamide group in the molecule can also engage in hydrogen bonding, which may further influence its permeability by interacting with polar sites on the membrane.

Overall, the combination of lipophilic and polar functional groups in the given molecule suggests that it may exhibit high permeability in the PAMPA assay, allowing it to effectively traverse the artificial membrane.

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 complex organic compound with several distinct structural features that influence its permeability in the PAMPA assay. Let's break down these features and their potential impact on permeability:

1. **Triazole Ring**: The presence of a triazole ring, which is a five-membered heterocyclic compound containing three nitrogen atoms, 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. **Oxadiazole Ring**: The oxadiazole ring, a five-membered heterocycle containing two nitrogen and one oxygen atom, can also contribute to the molecule's lipophilicity. This can enhance the molecule's ability to traverse lipid membranes, potentially leading to higher permeability.

3. **Benzoyl Group**: The benzoyl moiety, which is a phenyl ring attached to a carbonyl group, can increase the molecule's hydrophobic character. This can facilitate the passage of the molecule through the lipid bilayer of the artificial membrane, contributing to higher permeability.

4. **Carbamate Linkage**: The presence of a carbamate group, which is an ester of carbamic acid, can influence the molecule's solubility and permeability. Carbamates are often involved in hydrogen bonding, which can affect the molecule's interaction with the membrane and its overall permeability.

5. **Ethyl Ester Group**: The ethyl ester group at the end of the molecule can enhance lipophilicity, which is beneficial for membrane permeability. However, ester groups can also be hydrolyzed, which might affect the molecule's stability and permeability in the assay.

Overall, the given molecule's combination of heterocyclic rings, aromatic groups, and ester functionalities suggests 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.

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# 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, which is a non-polar, hydrophobic moiety, can enhance the molecule's lipophilicity. This can increase the molecule's ability to interact with the lipid components of the artificial membrane, potentially improving its permeability.

2. **Methoxyphenyl Group**: The methoxy group attached to the phenyl ring introduces a degree of polarity due to the presence of the oxygen atom. This can enhance the molecule's ability to form hydrogen bonds or dipole-dipole interactions with the membrane, potentially aiding in permeability.

3. **Triazolopyrazine Core**: The triazolopyrazine ring system is a heterocyclic structure that can contribute to the molecule's rigidity and planarity. This can affect how the molecule fits into the membrane, potentially facilitating or hindering permeability depending on the orientation and size of the molecule relative to the membrane pores.

4. **Carboxamide Group**: The carboxamide group is polar and can participate in hydrogen bonding. This functional group can enhance the molecule's solubility in aqueous environments and may also interact with the polar head groups of the artificial membrane, potentially aiding in permeability.

Overall, the given molecule's combination of hydrophobic and polar groups, along with its rigid heterocyclic core, suggests that it may have moderate permeability in the PAMPA assay. The balance of lipophilic and hydrophilic properties allows it to interact with both the lipid and polar components of the membrane, which is typical for molecules with moderate permeability.

Final answer: Low-to-moderate permeability.

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# 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 aromatic rings, including the phenyl and thiazole rings, can also contribute to the molecule's ability to interact with hydrophobic regions of the membrane, potentially aiding in its permeability.

The pyridine ring in the molecule can also play a role in its permeability. Pyridine is a basic heterocycle that can participate in hydrogen bonding and other polar interactions, which may help the molecule to interact with the polar head groups of the artificial membrane.

Overall, the combination of these functional groups suggests that the given molecule may have moderate to high permeability in the PAMPA assay, as it possesses both hydrophobic and hydrophilic characteristics that can facilitate interaction with the artificial membrane.

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 potential impact on permeability:

1. **Tert-butyl Ester Group**: The presence of a tert-butyl ester group in the molecule suggests that it may have moderate to high lipophilicity. This group can enhance the molecule's ability to interact with lipid membranes, potentially increasing its permeability through the artificial membrane.

2. **Chlorophenyl Group**: The chlorophenyl moiety contributes to the molecule's hydrophobic character. Chlorine atoms can enhance lipophilicity and may facilitate passage through the membrane by increasing the molecule's ability to dissolve in the lipid bilayer.

3. **Triazatricyclic Core**: The triazatricyclic structure is a complex, rigid framework that can influence the molecule's overall shape and electronic properties. This core may affect how the molecule interacts with the artificial membrane, potentially enhancing or hindering permeability depending on the fit and orientation within the membrane.

4. **Thia and Tetrazole Rings**: The presence of sulfur (thia) and nitrogen (tetrazole) atoms in the rings can introduce polar characteristics, which may affect the molecule's solubility and permeability. These heteroatoms can form hydrogen bonds or ionic interactions with the membrane, potentially influencing permeability.

5. **Methyl Substituents**: The methyl groups attached to the core structure can increase the hydrophobicity of the molecule, which may enhance its ability to permeate the membrane.

Overall, the given molecule's combination of lipophilic and polar features suggests that it may have moderate to high permeability in the PAMPA assay. The balance of hydrophobic and hydrophilic elements, along with the rigid tricyclic core, likely facilitates its interaction with the artificial membrane, allowing it to traverse the barrier effectively.

Final answer: High permeability

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# 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 member of the quinazoline class, which is known for its potential biological activity, often used in pharmaceuticals. The molecule contains several key structural 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 permeability due to its ability to interact with biological membranes, which are typically lipophilic.

2. **Pyridine Rings**: The presence of pyridine rings in the structure can enhance the molecule's ability to form hydrogen bonds and π-π interactions with the artificial membrane. These interactions can facilitate the passage of the molecule through the membrane.

3. **Difluorophenyl Group**: The difluorophenyl group introduces fluorine atoms, which can increase the lipophilicity of the molecule. Fluorine atoms can also enhance the metabolic stability of the molecule, potentially improving its permeability by reducing the likelihood of rapid degradation.

4. **Amino Linkage**: The amino linkage between the pyridine and quinazoline moieties can act as a hydrogen bond donor or acceptor, which may enhance the molecule's interaction with the membrane and improve its permeability.

5. **Carbonitrile Group**: The carbonitrile group is a polar functional group that can participate in hydrogen bonding and dipole-dipole interactions. This group may contribute to the molecule's solubility and permeability by interacting with the polar components of the membrane.

Overall, the combination of these structural features suggests that the given molecule is likely to have high permeability in the PAMPA assay, as it possesses a balance of hydrophobic and hydrophilic characteristics that facilitate interaction with 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:** 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, which can influence its permeability.

In the given molecule, the sulfonamide group is linked to a pyrimidinyl moiety, which is a heterocyclic aromatic compound. The presence of the pyrimidinyl group can contribute to the molecule's ability to permeate through biological membranes due to its planar structure, which can facilitate interactions with lipid bilayers.

Additionally, the molecule contains a chlorinated aromatic ring, which can enhance lipophilicity and membrane permeability due to the presence of the chlorine atom. The methoxy and methyl groups on the aromatic ring can also increase lipophilicity, further aiding in membrane permeability.

The thioether linkage in the molecule, connecting the sulfonamide group to the pyrimidinyl moiety, can also play a role in membrane permeability. Thioethers are generally more flexible than ethers, which can allow the molecule to adopt conformations that facilitate passage through the membrane.

Overall, the combination of these functional groups suggests that the given molecule likely exhibits high permeability in the PAMPA assay, as it possesses several features that enhance its ability to interact with and permeate through lipid membranes.

Final answer: High 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 potential impact on permeability:

1. **Piperidine Ring**: The presence of a piperidine ring, which is a six-membered ring containing one nitrogen atom, 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, potentially increasing permeability.

2. **Benzimidazole Core**: The benzimidazole moiety is a bicyclic structure that combines a benzene ring with an imidazole ring. This core is known for its stability and ability to participate in hydrogen bonding and π-π interactions. The benzimidazole structure can enhance the molecule's ability to permeate through lipid membranes due to its planar and aromatic nature.

3. **Urea Linkage**: The urea group in the molecule acts as a hydrogen bond donor and acceptor, which can facilitate interactions with the artificial membrane. Urea linkages are often involved in forming hydrogen bonds with the membrane, potentially enhancing permeability.

4. **Chloro and Methyl Substituents**: The chloro group on the phenyl ring can increase the lipophilicity of the molecule, which may enhance its ability to permeate through the lipid-rich environment of the artificial membrane. The methyl groups on both the phenyl ring and the piperidine ring can also contribute to the lipophilicity, further aiding in membrane permeability.

5. **Methyl Substitution on Benzimidazole**: The methyl group on the benzimidazole ring can increase the hydrophobic character of the molecule, which may improve its ability to traverse the lipid bilayer of the artificial membrane.

Overall, the given molecule's combination of aromatic rings, basic nitrogen atoms, and functional groups like urea and chloro substituents suggest that it would have 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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# 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 attached 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 group, which includes an amide linkage, 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 properties. The aromatic rings and heterocyclic components can enhance lipophilicity, while the sulfonamide and amide groups can provide some degree of hydrophilicity. This balance is crucial in determining the molecule's ability to permeate the artificial membrane in the PAMPA assay.

Final answer: Low-to-moderate permeability.

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# 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 that features several distinct structural elements, each contributing to its permeability characteristics in the PAMPA assay.

1. **Aromatic Rings**: The molecule contains a dichlorophenyl group and a pyrazolopyridine core. Aromatic rings, such as these, are known to enhance lipophilicity, which can increase the molecule's ability to permeate lipid membranes. The presence of chlorine atoms on the phenyl ring can further increase lipophilicity and potentially enhance membrane permeability due to the electron-withdrawing nature of chlorine, which can affect the electronic distribution across the molecule.

2. **Imidazo[1,2-a]pyridine Core**: This bicyclic structure is a fused heterocyclic system that can contribute to the molecule's rigidity and planarity. Such structural features can influence the molecule's ability to interact with the artificial membrane, potentially enhancing permeability by allowing the molecule to fit more snugly into the membrane's lipid bilayer.

3. **N,N-Dimethylcarboxamide Group**: This functional group introduces polar characteristics to the molecule, which can affect its solubility and permeability. The presence of the amide group can facilitate hydrogen bonding with the membrane, potentially aiding in permeation. However, the dimethyl substitution may also increase lipophilicity, balancing the overall permeability.

Overall, the given molecule's combination of aromatic rings, heterocyclic core, and polar functional groups suggests that it would exhibit high permeability in the PAMPA assay. The balance of lipophilic and polar characteristics allows the molecule to effectively interact with the artificial membrane, facilitating its passage through the lipid layer.

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 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.

2. **Aromatic Rings**: The presence of multiple aromatic rings, including a pyridine and a phenyl group, enhances the molecule's lipophilicity. Aromatic rings can participate in π-π interactions with the lipid components of the membrane, facilitating permeation.

3. **Methylation**: The methyl group attached to the phenyl ring increases the lipophilicity of the molecule, which can enhance its ability to traverse lipid membranes. Methyl groups can also influence the electronic properties of the aromatic ring, potentially affecting the molecule's interaction with the membrane.

4. **Amine Linkage**: The amine group in the quinazoline structure can form hydrogen bonds with the membrane, which may aid in permeability. However, the presence of this polar group can also introduce some degree of hydrophilicity, which might limit permeability depending on the balance with the lipophilic components.

Overall, the given molecule's combination of a quinazoline core, multiple aromatic rings, and a methyl group suggests that it would exhibit high permeability in the PAMPA assay. The balance of lipophilic and hydrophilic features allows it to effectively interact with the artificial membrane, facilitating its passage.

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 member of the chromones class, which are known for their aromatic and heterocyclic structures. The molecule features a chromone moiety, which is a bicyclic structure consisting of a benzene ring fused to a lactone. This chromone structure is known for its planar and aromatic characteristics, which can enhance the molecule's ability to interact with biological membranes.

Additionally, the molecule contains a thienopyrrole ring system, which is a sulfur-containing heterocycle. This contributes to the molecule's overall aromaticity and can influence its electronic properties, potentially affecting its interaction with the artificial membrane.

The presence of a piperidine ring, a six-membered nitrogen-containing heterocycle, adds to the molecule's structural complexity. Piperidine rings are often associated with increased solubility and can enhance the molecule's ability to permeate biological membranes due to their basic nature.

The carboxamide group attached to the piperidine ring introduces a polar functional group, which can form hydrogen bonds with the artificial membrane. This can influence the molecule's permeability by affecting its solubility and interaction with the membrane.

Overall, the combination of aromatic and heterocyclic structures, along with the polar carboxamide group, suggests that the given molecule may exhibit moderate permeability in the PAMPA assay. The aromatic and heterocyclic components can facilitate interactions with the membrane, while the carboxamide group can enhance solubility and binding affinity.

Final answer: Low-to-moderate permeability.

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# 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:** 1

**Correct:** 1

# Response:
The given molecule is an aromatic amide, which suggests that it has a structure that includes an amide 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 sulfonylamino group, which is a polar functional group. This group can increase the molecule's solubility in water, potentially aiding in its permeability through the membrane. The sulfonylamino group can also form hydrogen bonds with the membrane, which can further facilitate passage.

The acetyl group attached to the aromatic ring can also play a role in permeability. This group is relatively small and non-polar, which may allow the molecule to pass through the membrane without significant hindrance.

The pyrrole ring in the structure is a heterocyclic aromatic compound, which can contribute to the molecule's overall stability and ability to interact with the membrane. The presence of methyl and ethyl groups on the pyrrole ring can increase the molecule's lipophilicity, which may enhance its permeability by allowing it to dissolve in the lipid components of the membrane.

Overall, the combination of aromatic rings, polar functional groups, and hydrophobic alkyl groups suggests that the given molecule likely has high permeability in the Parallel Artificial Membrane Permeability Assay.

Final answer: High permeability

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# 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 can enhance lipophilicity, which generally increases membrane permeability. However, the presence of chlorine atoms on the phenyl ring can also introduce polar characteristics, potentially affecting the overall permeability.

2. **Amide Linkage**: The molecule has an amide linkage, which is a common feature in many bioactive compounds. Amides can form hydrogen bonds, which may enhance solubility and permeability. However, the presence of an amide group can also introduce some degree of polarity, which might reduce permeability through hydrophobic membranes.

3. **Sulfonamide Group**: The sulfonamide group is known for its ability to form strong hydrogen bonds, which can increase solubility and permeability. However, sulfonamides can also introduce some polarity, which might affect permeability.

4. **Thiadiazole Ring**: The thiadiazole ring is a heterocyclic compound that can contribute to the molecule's overall stability and lipophilicity. The presence of nitrogen and sulfur atoms in the ring can introduce polar characteristics, which might affect permeability.

5. **Carboxylate Ester**: The ethyl ester group is a common prodrug moiety that can enhance lipophilicity, potentially increasing permeability. However, esters can be hydrolyzed in biological systems, which might affect the molecule's stability and permeability.

Overall, the given molecule has a balance of hydrophobic and hydrophilic characteristics due to its aromatic rings, amide and sulfonamide groups, and ester functionality. These features suggest that the molecule may have moderate permeability in the PAMPA assay, as it can interact with both hydrophobic and hydrophilic environments. However, the specific permeability would depend on the exact nature of the artificial membrane used in the assay.

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. **Sulfonyl Group**: The sulfonyl group is a strong electron-withdrawing group, which can increase the molecule's polarity. This can enhance the molecule's solubility in aqueous environments, potentially improving its permeability through the membrane.

4. **Chloro and Trifluoromethyl Substituents**: The chloro and trifluoromethyl groups are hydrophobic and can increase the lipophilicity of the molecule. This can enhance the molecule's ability to traverse lipid-rich environments, such as biological membranes. However, these groups can also hinder permeability if they cause steric hindrance or disrupt the membrane's integrity.

5. **Piperidine Ring**: The piperidine ring is a saturated nitrogen-containing heterocycle that can increase the molecule's basicity and solubility. This can facilitate the molecule's interaction with the membrane and improve its permeability.

Overall, the given molecule has a balance of hydrophilic and hydrophobic properties, with polar groups that can form hydrogen bonds and hydrophobic groups that can interact with lipid membranes. These features suggest that the molecule would have moderate to high permeability in the PAMPA assay, as it can effectively interact with both the aqueous and lipid components of the membrane.

Final answer: High permeability.

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# 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 to understand its permeability characteristics.

1. **Phenyl Groups**: The molecule contains two 4-chlorophenyl groups and one 2,4-dichlorophenyl 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. The presence of chlorine atoms increases the electron-withdrawing capacity, potentially affecting the molecule's overall polarity and solubility.

2. **Pyrazole Ring**: The pyrazole ring is a five-membered heterocyclic structure containing two nitrogen atoms. This ring can participate in hydrogen bonding and other polar interactions, which may influence the molecule's binding affinity to the membrane. The presence of the pyrazole ring can also contribute to the molecule's rigidity, affecting its overall shape and how it fits into the membrane.

3. **Carboxamide Group**: The carboxamide group is a polar functional group that can form hydrogen bonds with the membrane. This group can increase the molecule's solubility in aqueous environments and may facilitate interactions with the polar head groups of the artificial membrane.

4. **Piperidine Ring**: The piperidine moiety is a six-membered nitrogen-containing ring that can enhance the molecule's basicity. This basicity can affect the molecule's ionization state, which in turn influences its permeability. The piperidine ring can also contribute to the molecule's overall flexibility, allowing it to adapt its conformation to fit into the membrane.

Overall, the given molecule's structure suggests a balance of hydrophobic and hydrophilic properties, with multiple aromatic rings contributing to hydrophobic interactions and polar functional groups facilitating hydrogen bonding. These features suggest that the molecule may have moderate permeability in the PAMPA assay, as it can interact with both hydrophobic and hydrophilic components of the membrane. 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.

------
# 260

**SMILES:** CC1=CC=C(C=C1)S(=O)(=O)NC2=C(C=CN=C2)C(=O)NCC3=CC=CC=C3

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a PAMPA permeability assay model, which is used to predict the permeability of a compound across biological membranes. The molecule is characterized by several functional groups and structural features that influence its permeability.

The molecule contains a pyridine ring, which is a nitrogen-containing heterocycle. Pyridine rings are known to enhance the lipophilicity of a compound, which can improve its ability to permeate lipid membranes. This is because the nitrogen atom can participate in hydrogen bonding and other interactions with the membrane, potentially facilitating passage through the membrane.

Additionally, the molecule has a sulfonamide group, which is a common feature in many pharmaceuticals. Sulfonamides can increase the solubility of a compound in water, which is important for bioavailability. However, they can also introduce steric hindrance and affect the overall permeability depending on the specific molecular environment.

The presence of a benzyl group (phenylmethyl) and a methylphenyl group (tolyl) further contributes to the lipophilicity of the molecule. These aromatic groups can enhance membrane permeability by increasing the hydrophobic character of the molecule, allowing it to interact more favorably with the lipid bilayer of the membrane.

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 hydrophilic and hydrophobic properties that facilitate membrane interaction and passage.

Final answer: High permeability

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# 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:** 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. This structural feature is significant in determining the molecule's permeability.

The presence of the aromatic amide group indicates that the molecule has a degree of rigidity and planarity, which can influence its ability to permeate through the artificial membrane. Aromatic rings are known for their ability to participate in π-π interactions, which can enhance the molecule's binding affinity to the membrane.

Additionally, the molecule contains a pyrrole ring, which is a five-membered heterocyclic aromatic ring. The presence of this ring can contribute to the molecule's overall aromaticity and influence its electronic properties, potentially affecting its permeability.

The acetyl group attached to the pyrrole ring introduces a polar functional group, which can enhance the molecule's solubility in polar environments, such as the aqueous phase of the PAMPA assay. This could facilitate its passage through the membrane.

The methoxy and dimethyl groups on the pyrrole ring increase the molecule's hydrophobic character, which may enhance its ability to interact with the lipid components of the artificial membrane.

The presence of a bromophenyl group introduces a bulky and electron-withdrawing substituent, which can affect the molecule's overall shape and electronic distribution. This could influence the molecule's ability to fit into the membrane's structure and its overall permeability.

Overall, the combination of aromaticity, polar functional groups, and hydrophobic substituents suggests that the given molecule may exhibit moderate permeability in the PAMPA assay, balancing between hydrophilic and hydrophobic interactions with the artificial membrane.

Final answer: Low-to-moderate 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 lipophilic.

2. **Fluorophenyl Group**: The presence of a fluorine atom on the phenyl ring can enhance the molecule's lipophilicity, which is beneficial for membrane permeability. Fluorine can also influence the electronic properties of the molecule, potentially affecting its interaction with the artificial membrane.

3. **Pyridine Ring**: The pyridine ring is a heterocyclic aromatic compound that can participate in hydrogen bonding and π-π interactions with the membrane. This can enhance the molecule's ability to permeate the membrane by stabilizing interactions with the membrane's lipophilic and polar regions.

4. **Pyrrolidine Group**: The pyrrolidine moiety is a saturated nitrogen-containing ring that can increase the molecule's solubility and flexibility. This can improve the molecule's ability to navigate through the membrane by providing a balance between hydrophilic and lipophilic properties.

Overall, the combination of these structural features suggests that the given molecule is likely to have high permeability in the PAMPA assay. The quinazoline core, along with the fluorophenyl and pyridine groups, contribute to its ability to interact favorably with the artificial membrane, while the pyrrolidine group enhances its solubility and flexibility.

Final answer: High permeability

------
# 263

**SMILES:** CNC1=C(C=CC(=N1)C2=CC=CC3=CC=CC=C32)C#N

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a member of the quinoline family, which is known for its aromatic heterocyclic structure. This particular molecule contains a quinoline moiety, which is a fused ring system consisting of a benzene ring and a pyridine ring. The presence of this quinoline structure contributes to the molecule's aromaticity and potential for π-π interactions, which can influence its permeability.

Additionally, the molecule features a naphthalenyl group, which is another aromatic system composed of two fused benzene rings. This naphthalenyl group can enhance the lipophilicity of the molecule, potentially increasing its ability to traverse lipid membranes.

The molecule also contains a nitrile group attached to the pyridine ring. Nitrile groups are polar and can participate in hydrogen bonding, which may affect the molecule's solubility and permeability. However, the presence of the nitrile group may also introduce some degree of polarity that could hinder permeability through non-polar membranes.

Furthermore, the molecule has a methylamino group attached to the pyridine ring. This group is basic and can form hydrogen bonds, which may influence the molecule's interaction with the artificial membrane. The methylamino group can also affect the overall polarity and solubility of the molecule.

Overall, the combination of aromatic systems and functional groups in the given molecule suggests that it may exhibit moderate permeability in the PAMPA assay. The aromatic rings contribute to lipophilicity, while the polar functional groups may introduce some polarity, balancing the molecule's permeability characteristics.

Final answer: Low-to-moderate permeability.

------
# 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, which contribute to its permeability characteristics in the PAMPA assay.

1. **N-arylpiperazine Structure**: The presence of the piperazine ring, which is a six-membered ring containing two nitrogen atoms, is a key feature. N-arylpiperazines are known for their ability to interact with biological membranes due to their basic nitrogen atoms, which can form hydrogen bonds and ionic interactions with the membrane. This can enhance the molecule's permeability.

2. **Aromatic Rings**: The molecule contains multiple aromatic rings, including a methoxyphenyl group and a pyrimidinyl group. Aromatic rings can increase lipophilicity, which often enhances membrane permeability. The methoxy group on the phenyl ring can also contribute to the molecule's overall lipophilicity and may affect its ability to interact with the membrane.

3. **Amide Linkage**: The methanone group (an amide linkage) in the molecule can participate in hydrogen bonding, which may influence the molecule's interaction with the membrane. Amide linkages are relatively stable and can contribute to the overall rigidity of the molecule, potentially affecting its permeability.

4. **Pyrimidine Ring**: The pyrimidine ring is a heterocyclic aromatic compound that can enhance the molecule's ability to permeate biological membranes. Pyrimidines are often involved in interactions with nucleic acids and proteins, which can be relevant in drug design.

Overall, the combination of these structural features suggests that the given molecule is likely to have high permeability in the PAMPA assay. The presence of aromatic rings and the piperazine moiety contribute to its lipophilicity and ability to interact with the artificial membrane, while the amide linkage and pyrimidine ring provide additional points for interaction and stability.

Final answer: High permeability

------
# 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 thieno[2,3-d]pyrimidine 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 thieno[2,3-d]pyrimidine moiety is a bicyclic structure that includes both sulfur and nitrogen atoms. The presence of these heteroatoms can enhance the molecule's ability to participate in hydrogen bonding and other polar interactions, which may affect its permeability across the artificial membrane.

The molecule also contains an amide linkage, which is a common functional group in many bioactive compounds. Amides can form hydrogen bonds, which may facilitate interactions with the artificial membrane, potentially enhancing permeability.

Overall, the combination of aromaticity, heteroatoms, and the amide linkage suggests that the given molecule may exhibit moderate permeability in the PAMPA assay, as these features can facilitate interactions with the membrane while also potentially limiting permeability due to steric and electronic factors.

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 that includes 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 also contains a thiazole ring, which is a five-membered ring containing both sulfur and nitrogen atoms. This heterocyclic structure can contribute to the molecule's overall stability and electronic properties, potentially affecting its interaction with the artificial membrane.

Additionally, the presence of a trifluoromethyl group attached to the phenyl ring can significantly enhance the lipophilicity of the molecule. The trifluoromethyl group is known for its electron-withdrawing properties, which can influence the molecule's ability to permeate through the membrane by increasing its hydrophobic character.

Overall, the combination of these structural features suggests that the given molecule may exhibit moderate to high permeability in the PAMPA assay, as the balance of hydrophobic and hydrophilic properties allows it to interact favorably with 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 potential 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. **Cyanophenyl Group**: The cyanophenyl group introduces a polar nitrile group, which can engage in hydrogen bonding and dipole-dipole interactions. This can affect the molecule's solubility and permeability, potentially increasing it due to the polar nature of the nitrile group.

3. **Methyl Substitution**: The methyl group on the indole ring can influence the molecule's lipophilicity. While small, the methyl group can increase the hydrophobic character of the molecule, which may enhance its ability to permeate lipid membranes.

4. **Pyridinylmethyl Moiety**: The pyridinylmethyl group adds another aromatic ring to the structure, which can contribute to the overall planarity and aromaticity of the molecule. This can further facilitate membrane permeation by allowing the molecule to interact with the lipid bilayer.

5. **Carboxamide Group**: The carboxamide group is polar and can form hydrogen bonds, which may affect the molecule's solubility and permeability. However, in the context of PAMPA, the presence of this group might not significantly hinder permeability due to its relatively small size and the overall balance of hydrophobic and hydrophilic features.

Overall, the given molecule's structure suggests that it has a balance of hydrophobic and hydrophilic properties, with multiple aromatic rings and polar functional groups. This combination is likely to result in 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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# 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 pyrimidinecarboxamide, which indicates that it contains a pyrimidine ring attached to a carboxamide group. The pyrimidine ring is a six-membered aromatic heterocycle containing two nitrogen atoms, which can contribute to the molecule's ability to interact with biological membranes.

The presence of the carboxamide group suggests that the molecule may have hydrogen bonding capabilities, which can influence its permeability by allowing it to form interactions with the artificial membrane. The carboxamide group can also increase the molecule's polarity, potentially affecting its solubility and permeability.

The 2-chloro-6-methylphenyl group attached to the pyrimidine ring introduces a chlorinated aromatic ring, which can enhance the molecule's lipophilicity. This increased lipophilicity can improve the molecule's ability to permeate through the lipid components of the artificial membrane.

Additionally, the 5-methylthio substituent on the pyrimidine ring introduces a sulfur atom, which can further influence the molecule's lipophilicity and electronic properties. The presence of the methylthio group can also affect the molecule's overall steric profile, potentially impacting its ability to fit into the membrane's structure.

Overall, the combination of these structural features suggests that the given molecule may exhibit high permeability in the artificial membrane, as it possesses both lipophilic and polar characteristics that facilitate interaction with the membrane.

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.

The molecule contains a pyridine ring, which is a six-membered aromatic ring with one nitrogen atom. This nitrogen atom can participate in hydrogen bonding and can also contribute to the molecule's overall polarity. The presence of the pyridine ring suggests that the molecule may have moderate polarity, which can influence its permeability through the artificial membrane.

Additionally, the molecule includes a methoxy group attached to a pyridine ring. The methoxy group is an electron-donating group, which can increase the electron density of the aromatic ring, potentially affecting the molecule's interaction with the membrane. This group can also contribute to the molecule's overall hydrophobic character, which may enhance its permeability through the membrane.

The molecule also features an indole moiety, which is a bicyclic structure consisting of a benzene ring fused to a pyrrole ring. Indole structures are known for their planar aromaticity, which can facilitate stacking interactions with other aromatic systems in the membrane. This can enhance the molecule's ability to permeate the membrane.

Furthermore, the molecule contains a carboxamide group, which is a polar functional group capable of forming hydrogen bonds. This group can increase the molecule's solubility in aqueous environments, which is beneficial for permeability in the PAMPA assay.

Overall, the combination of aromatic systems, polar functional groups, and electron-donating substituents suggests that the given molecule likely exhibits moderate to high permeability in the PAMPA assay, as it can engage in various interactions with the artificial membrane while maintaining a balance of hydrophilic and hydrophobic properties.

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 features several distinct structural components, each contributing to its permeability characteristics in the PAMPA assay.

1. **Aromatic Rings**: The molecule contains two aromatic rings, one being a butoxyphenyl group and the other a methylphenyl 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. **Piperidine Ring**: The presence of a piperidine ring, a six-membered nitrogen-containing heterocycle, can influence the molecule's basicity and solubility. Piperidine rings are often found in pharmacologically active compounds and can enhance the molecule's ability to permeate biological membranes due to their flexible and polar nature.

3. **Triazolone Moiety**: The triazolone group is a five-membered ring containing nitrogen atoms, which can participate in hydrogen bonding and other polar interactions. This moiety can enhance the molecule's solubility in aqueous environments and may also contribute to its ability to permeate the membrane by interacting with polar sites.

4. **Butoxy Chain**: The butoxy group attached to the phenyl ring introduces additional hydrophobic character to the molecule. This can further enhance the molecule's ability to permeate the membrane by increasing its lipophilicity.

Overall, the combination of aromatic rings, the piperidine ring, the triazolone moiety, and the butoxy chain suggests that the given molecule is likely to 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 the membrane.

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 through π-π stacking and hydrophobic interactions. This can enhance the molecule's permeability.

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 enhancing the molecule's ability to permeate the membrane by increasing its hydrophobic character.

3. **Piperazine Ring**: The piperazine moiety is a common feature in many pharmaceuticals and can contribute to the molecule's solubility and permeability. The nitrogen atoms in the piperazine ring can participate in hydrogen bonding, which may aid in the molecule's interaction with the membrane.

4. **Amine Groups**: The quinazoline-amine structure suggests the presence of amine groups, which can form hydrogen bonds with the artificial membrane. These interactions can be crucial for the molecule's permeability, as they can help stabilize the molecule's orientation and binding to the membrane.

Overall, the combination of aromatic systems, fluorinated groups, and nitrogen-containing heterocycles suggests that the given molecule is likely to exhibit high permeability in the PAMPA assay. These structural features enhance its ability to interact with the artificial membrane through hydrophobic interactions, π-π stacking, and hydrogen bonding, facilitating its passage through the membrane.

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 predict its permeability in the PAMPA assay, we need to consider the structural features of the molecule.

The molecule contains a pyridine ring, which is a nitrogen-containing heterocycle. Pyridine rings are known to enhance the lipophilicity of a molecule, which can improve its ability to permeate lipid membranes. This is because the nitrogen atom can participate in hydrogen bonding and other interactions with the membrane, potentially facilitating passage through the membrane.

Additionally, the molecule has a dimethylamino group attached to the phenyl ring. This group is electron-donating and can increase the overall lipophilicity of the molecule. The presence of this group may also influence the molecule's ability to interact with the artificial membrane, potentially enhancing its 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 impacting its permeability.

Overall, the combination of the pyridine ring, dimethylamino group, and furo[3,2-b]pyridine moiety suggests that the given molecule may exhibit high permeability in the PAMPA assay due to its enhanced lipophilicity and potential for favorable interactions with the artificial membrane.

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:** 1

**Correct:** 1

# 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 is known for its ability to interact with biological targets, often due to its aromatic and heterocyclic nature.

The molecule has several functional groups that influence its permeability:

1. **Thienopyridine Core**: The bicyclic structure provides a planar and rigid framework, which can facilitate interactions with biological membranes. The aromatic nature of the thiophene ring can enhance lipophilicity, potentially increasing membrane permeability.

2. **Ester Groups**: The presence of ethyl ester groups in the molecule can increase lipophilicity, which is often associated with higher permeability through lipid membranes. Esters can also undergo hydrolysis in biological systems, which might be relevant for the molecule's activity or metabolism.

3. **Piperidine Ring**: The piperidine moiety is a saturated nitrogen-containing ring that can enhance the molecule's solubility and potentially its ability to interact with biological targets. The presence of this group can also influence the molecule's pharmacokinetic properties, such as absorption and distribution.

4. **Amide Linkages**: The molecule contains amide linkages, which can form hydrogen bonds with biological molecules, potentially affecting its binding affinity and specificity. Amides are generally polar, which can influence the molecule's solubility and permeability.

Overall, the combination of the thienopyridine core, ester groups, piperidine ring, and amide linkages suggests that the given molecule may exhibit high permeability due to its lipophilic and aromatic characteristics, balanced with polar functional groups that can interact with biological targets.

Final answer: High 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 and the presence of an amide group, which can form hydrogen bonds with membrane components.

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 lipid membranes, increasing its permeability. The bromine atom on the phenyl ring can also contribute to the molecule's lipophilicity, potentially enhancing its permeability.

3. **Methoxy and Methyl Groups**: The methoxy group on the phenyl ring can increase the molecule's polarity, which may affect its solubility and permeability. The presence of a methyl group can also influence the molecule's lipophilicity, potentially enhancing its ability to permeate lipid membranes.

4. **Sulfonamide Linkage**: The sulfonamide group is known for its ability to form strong hydrogen bonds, which can influence the molecule's interaction with the artificial membrane. This group can also contribute to the molecule's overall polarity, which may affect its permeability.

Overall, the combination of aromatic rings, the benzamide core, and functional groups such as methoxy, methyl, and sulfonamide suggest that the given molecule is likely to have high permeability in the artificial membrane used in the PAMPA assay. These structural features enable the molecule to interact favorably with the lipid components of the membrane, facilitating its passage through the assay.

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:** 0

**Correct:** 0

# Response:
The given molecule is a complex natural product with a tricyclic core structure, which is often associated with significant biological activity. The presence of multiple rings and a rigid framework suggests that the molecule has a defined three-dimensional shape, which can influence its interaction with biological membranes.

The molecule contains several functional groups that are relevant to its permeability:

1. **Hydroxyl Groups**: The presence of two hydroxyl groups can increase the molecule's hydrophilicity, potentially enhancing its solubility in aqueous environments. This can facilitate its interaction with the polar head groups of the artificial membrane, which is composed of a diol.

2. **Acetate Ester**: The acetate group can influence the molecule's lipophilicity, which is crucial for permeability. Esters are often involved in hydrolysis reactions, which can affect the molecule's stability and permeability.

3. **Methyl and Methylidene Groups**: These groups contribute to the hydrophobic character of the molecule. The presence of these groups can enhance the molecule's ability to interact with the hydrophobic regions of the artificial membrane.

4. **Benzyl Group**: The benzyl moiety adds to the lipophilicity of the molecule, which can facilitate its passage through the lipid bilayer of the artificial membrane.

5. **Tricyclic Core**: The rigid tricyclic structure can provide a specific orientation for the functional groups, which may enhance or hinder the molecule's interaction with the membrane depending on the orientation and spatial arrangement.

Overall, the given molecule's combination of hydrophilic and hydrophobic groups, along with its rigid tricyclic structure, suggests that it may have moderate permeability through the artificial membrane. The balance of these features will determine its ability to traverse the membrane, with the hydrophilic groups potentially aiding in solubility and the hydrophobic groups facilitating membrane interaction.

Final answer: Low-to-moderate permeability.

------
# 276

**SMILES:** C1=CC=C(C=C1)CNC2=NC(=NC3=CC=CC=C32)NCC4=CC=CC=C4

**Label:** 1

**Predi:** 0

**Correct:** 0

# 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 molecule has two benzyl groups attached to the nitrogen atoms of the quinazoline core. These benzyl groups are hydrophobic and can enhance the lipophilicity of the molecule, potentially increasing its ability to permeate lipid membranes. The presence of these groups can also contribute to the molecule's overall steric bulk, which may affect its interaction with the artificial membrane.

Additionally, the molecule has amino groups attached to the quinazoline core. These groups can participate in hydrogen bonding, which may influence the molecule's solubility and permeability. The balance between the hydrophobic benzyl groups and the polar amino groups can affect the overall permeability of the molecule.

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 hydrophobic nature of the benzyl groups could facilitate membrane permeation, while the amino groups may provide some degree of solubility and interaction with the membrane. However, the exact permeability would depend on the specific conditions and the nature of the artificial membrane used in the assay.

Final answer: Low-to-moderate 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:** 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. **Dihydropyridine Core**: The presence of a 1,4-dihydropyridine ring is a key feature in many calcium channel blockers. This core is known for its ability to interact with biological membranes, often enhancing permeability due to its planar structure and potential for hydrogen bonding and ionic interactions.

2. **Aromatic Rings**: The molecule contains multiple aromatic rings, including a phenyl group and a nitrophenyl group. Aromatic rings can increase lipophilicity, which generally enhances membrane permeability. However, the nitro group on the phenyl ring introduces an electron-withdrawing effect, which might slightly reduce the overall lipophilicity and permeability.

3. **Alkyl Chains**: The presence of propyl and butyl chains contributes to the lipophilic character of the molecule. These chains can facilitate the passage of the molecule through the lipid bilayer of the artificial membrane by increasing hydrophobic interactions.

4. **Ester Groups**: The molecule contains ester linkages, which can influence its solubility and permeability. Esters are generally polar and can participate in hydrogen bonding, which may affect the molecule's interaction with the membrane.

5. **Piperidine Ring**: The piperidine moiety is a common structural feature in many pharmaceuticals, often enhancing the molecule's ability to cross biological membranes. Its presence in the molecule suggests potential for increased permeability due to its basic nitrogen, which can participate in ionic interactions.

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, alkyl chains, and functional groups like esters and piperidine rings likely contribute to its ability to traverse the artificial membrane, indicating a high permeability.

Final answer: High permeability

------
# 278

**SMILES:** C1=CC=C2C(=C1)/C(=C/C3=CC=CN3)/C(=O)N2

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a derivative of indole, which is a bicyclic structure consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. This structure is known for its planar and aromatic characteristics, which can influence the molecule's interaction with biological membranes.

The presence of the pyrrole moiety, a five-membered heterocyclic ring containing a nitrogen atom, 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.

Additionally, the indole structure is known for its lipophilicity, which can facilitate the passage of the molecule through lipid membranes. The conjugated system within the indole ring can also contribute to the molecule's ability to interact with the membrane through van der Waals forces and π-π stacking.

The methylene bridge connecting the pyrrole and indole moieties introduces a degree of flexibility, which may allow the molecule to adopt conformations that optimize its interaction with the membrane.

Overall, the combination of aromaticity, hydrogen bonding potential, and lipophilicity suggests that the given molecule likely exhibits high permeability in the Parallel Artificial Membrane Permeability Assay (PAMPA).

Final answer: High 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. **Thiazolopyrazinone Core**: The presence of a thiazolopyrazinone core suggests a relatively rigid and planar structure. This core can facilitate interactions with the artificial membrane, potentially enhancing permeability due to its ability to fit into membrane pores or interact with membrane lipids.

2. **Trifluoromethyl Group**: The trifluoromethyl group is known for increasing lipophilicity, which can enhance the molecule's ability to traverse lipid membranes. This group can also influence the electronic properties of the molecule, potentially affecting its interaction with the membrane.

3. **Methoxyphenyl Group**: The methoxyphenyl moiety contributes to the molecule's overall lipophilicity and can enhance its ability to interact with hydrophobic regions of the membrane. The presence of the methoxy group can also influence the electronic distribution, potentially affecting binding interactions with the membrane.

4. **Ethyl Linker**: The ethyl linker between the methoxyphenyl group and the thiazolopyrazinone core provides flexibility, allowing the molecule to adopt conformations that may be favorable for membrane permeation. This flexibility can help the molecule to adapt to the shape of the membrane pores.

5. **Methyl Group**: The methyl group on the thiazolopyrazinone core can contribute to the molecule's overall hydrophobic character, which may enhance its permeability through lipid-rich environments.

Overall, the given molecule's combination of lipophilic groups, rigid core structure, and flexible linkers suggests that it may have high permeability in the PAMPA assay. The balance of hydrophobic and electronic properties likely facilitates its interaction with the artificial membrane, allowing it to pass through with relative ease.

Final answer: High permeability

------
# 280

**SMILES:** CC1=CC=C(C=C1)S(=O)(=O)NC2=C(C=CN=C2)C(=O)NC3=NC(=CS3)C4CCC4

**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.

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. This ring can contribute to the molecule's electronic properties, potentially affecting its interaction with biological membranes.

Additionally, the molecule features a pyridine ring, which is a six-membered aromatic ring containing nitrogen. Pyridine rings are often involved in hydrogen bonding and can enhance the molecule's solubility in water, which may influence its permeability.

The cyclopentyl group attached to the thiazole ring introduces a non-polar, hydrophobic moiety, which can affect the molecule's overall balance between hydrophilicity and lipophilicity. This balance is crucial in determining the molecule's permeability, as it affects the ability to cross lipid membranes.

Overall, the combination of these functional groups and structural features suggests that the given molecule may have moderate permeability to the artificial membrane, as the presence of both hydrophilic and lipophilic components can facilitate its passage through the membrane while also allowing for specific interactions with the membrane components.

Final answer: Low-to-moderate permeability.

------
# 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:** 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 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 engage in π-π interactions, which can enhance the molecule's ability to permeate through the membrane.

Additionally, the molecule contains a sulfamoyl group attached to a phenyl ring. This group can increase the molecule's polarity, potentially enhancing its solubility in aqueous environments and thus its permeability through the membrane.

The acetyl group on the pyrrole ring can also contribute to the molecule's overall polarity and may affect its interaction with the membrane. However, the presence of methyl groups on the pyrrole ring can increase the hydrophobic character of the molecule, which might reduce its permeability due to decreased solubility in the membrane's environment.

Overall, the balance of these structural features suggests that the given molecule may exhibit moderate permeability in the artificial membrane, as the polar and non-polar regions are balanced, allowing for some degree of interaction with the membrane.

Final answer: Low-to-moderate permeability.

------
# 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 an aromatic amide, which suggests that it has a structure that includes an amide 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 stacking 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 can also participate in π-π interactions, further aiding in membrane permeability.

The acetyl groups present in the molecule can increase its 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.

Overall, the combination of aromatic rings, the amide linkage, and the acetyl groups suggest that the given molecule likely has high permeability in the Parallel Artificial Membrane Permeability Assay (PAMPA).

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 with several distinct structural features that influence its permeability in the PAMPA assay. Let's break down these features and their potential impact on permeability:

1. **Quinazoline Core**: The quinazoline moiety is a bicyclic structure that is relatively planar and aromatic. This core can enhance the molecule's ability to interact with the artificial membrane through π-π stacking interactions, which can contribute to its permeability. However, the presence of a chlorine atom on this ring may increase the molecule's lipophilicity, potentially enhancing its permeability by increasing its ability to dissolve in the lipid components of the membrane.

2. **Benzoxazole Ring**: The benzoxazole group is another aromatic system that can contribute to the molecule's overall planarity and ability to engage in π-π interactions with the membrane. The presence of a chlorine atom on this ring further increases the lipophilicity, which can enhance permeability by facilitating passage through the lipid bilayer.

3. **Pyrimidinylamino Linkage**: The pyrimidinylamino group introduces a nitrogen-rich heterocycle, which can form hydrogen bonds with the membrane or other molecules. This can influence the molecule's orientation and interaction with the membrane, potentially affecting its permeability. The presence of nitrogen atoms can also introduce polar characteristics, which might affect the balance between hydrophilicity and lipophilicity, impacting permeability.

4. **Tetrahydroquinazoline Component**: The partially saturated tetrahydroquinazoline portion of the molecule provides a degree of flexibility and may influence the overall conformation of the molecule. This flexibility can affect how the molecule fits into the membrane, potentially impacting its permeability.

Overall, the given molecule's combination of aromatic systems, chlorine substituents, and heterocyclic components suggests that it has a balance of hydrophilic and lipophilic properties. The aromatic and lipophilic characteristics are likely to dominate, suggesting that the molecule would exhibit high permeability in the PAMPA assay.

Final answer: High permeability

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# 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.

2. **Pyridine Ring**: The presence of a pyridine ring, which is a nitrogen-containing heterocycle, can enhance the molecule's ability to form hydrogen bonds and engage in π-π interactions with the membrane. This can increase the molecule's affinity for the lipid bilayer, potentially improving its permeability.

3. **Methoxyphenyl Group**: The methoxy group attached to the phenyl ring can increase the molecule's lipophilicity, which is often correlated with better membrane permeability. The methoxy group can also participate in hydrogen bonding, which may further facilitate interaction with the membrane.

4. **Phenyl Group**: The phenyl group contributes to the overall hydrophobic character of the molecule, which can enhance its ability to traverse lipid membranes. The aromatic nature of the phenyl group can also facilitate π-π stacking interactions with the lipid bilayer.

5. **Amine Linkage**: The amine group in the quinazoline structure can form hydrogen bonds with the membrane, potentially aiding in the molecule's permeation.

Overall, the combination of these structural features suggests that the given molecule is likely to have high permeability in the PAMPA assay. The planar and aromatic nature of the quinazoline core, along with the lipophilic and hydrogen-bonding capabilities of the pyridine, methoxyphenyl, and phenyl groups, all contribute to its ability to interact favorably with the artificial membrane.

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 typically have a cyclohexanone core structure with an aryl group attached. In this case, the aryl group is a 2-chlorophenyl group, which is a phenyl ring with a chlorine atom attached to the second position. 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 group, which is a polar functional group. The presence of the ketone can increase the molecule's ability to form hydrogen bonds, which may enhance its interaction with the polar components of the artificial membrane.

Additionally, the molecule contains a methylamino group attached to the cyclohexanone ring. This group introduces basicity to the molecule, which can affect its ionization state at physiological pH. The presence of the methylamino group can also enhance the molecule's solubility in aqueous environments, potentially improving its permeability through the membrane.

Overall, the combination of the aryl group, cyclohexanone core, and methylamino group suggests that the given molecule may have moderate permeability through the artificial membrane, as it possesses both hydrophobic and hydrophilic characteristics. However, the exact permeability would depend on the specific conditions of the PAMPA assay, such as pH and membrane composition.

Final answer: Low-to-moderate permeability.

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# 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 hydroxyquinoline derivative, which is known for its potential biological activity, including antimicrobial and antimalarial properties. The molecule's structure includes a quinoline core, which is a bicyclic aromatic compound consisting of a benzene ring fused to a pyridine ring. This core is substituted with a chlorine atom and a hydroxyl group, which can influence its chemical properties and biological activity.

The presence of the hydroxyl group on the quinoline ring can enhance the molecule's ability to form hydrogen bonds, potentially increasing its solubility in water and affecting its interaction with biological membranes. The chlorine atom can also impact the molecule's lipophilicity and electronic properties, which may influence its permeability across lipid membranes.

The methoxyphenyl group attached to the quinoline core introduces additional aromaticity and can further modulate the molecule's lipophilicity. The methoxy group is an electron-donating group, which can affect the electronic distribution within the molecule, potentially influencing its binding affinity and permeability.

The propanamide moiety is a small, polar group that can also contribute to the molecule's solubility and permeability. Amide groups are known for their ability to participate in hydrogen bonding, which can affect the molecule's interaction with the artificial membrane.

Overall, the combination of these structural features suggests that the given molecule may exhibit moderate permeability in the PAMPA assay, as the balance of hydrophilic and lipophilic groups can facilitate its passage through the artificial membrane while maintaining sufficient interaction with the membrane components.

Final answer: Low-to-moderate permeability.

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# 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:** 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. **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. This can enhance the molecule's ability to interact with the artificial membrane, potentially increasing its permeability. The presence of a methyl group on one of the indole rings can also influence the electronic properties, potentially affecting the molecule's overall polarity and permeability.

2. **Diketone Functionality**: The presence of two carbonyl groups (dioxo) in the indole structure introduces polar characteristics to the molecule. These carbonyl groups can form hydrogen bonds with the artificial membrane, which may facilitate or hinder permeability depending on the balance between hydrophilic and hydrophobic interactions.

3. **Propyl Linker**: The propyl chain acts as a flexible spacer that connects the indole groups to the rest of the molecule. This flexibility can allow the molecule to adopt conformations that optimize its interaction with the membrane, potentially enhancing permeability.

4. **Carbamimidothioate Group**: This functional group introduces additional polar characteristics to the molecule. The presence of sulfur and nitrogen atoms can form hydrogen bonds or ionic interactions with the membrane, which may influence permeability. The carbamimidothioate group can also contribute to the overall solubility of the molecule, which is a key factor in permeability.

Overall, the given molecule's structure suggests that it may have moderate permeability in the PAMPA assay. The balance of hydrophobic indole rings and hydrophilic carbonyl and carbamimidothioate groups suggests that the molecule can interact with the membrane, but the presence of multiple polar groups may limit its permeability compared to more hydrophobic compounds.

Final answer: Low-to-moderate permeability.

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# 288

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

**Label:** 1

**Predi:** 1

**Correct:** 1

# Response:
The given molecule is a member of acetophenones, which indicates the presence of an acetophenone moiety. This moiety consists of a phenyl group attached to a carbonyl group, which is known for its lipophilic properties. This lipophilicity can enhance the molecule's ability to interact with lipid membranes, potentially increasing its permeability.

The molecule also contains a thiazole ring, which is a five-membered heterocyclic compound containing both sulfur and nitrogen. Thiazole rings are often involved in biological activity due to their ability to participate in hydrogen bonding and π-π interactions. This can contribute to the molecule's ability to interact with biological targets, potentially affecting its permeability.

Additionally, the molecule features a piperidine ring, which is a six-membered nitrogen-containing heterocycle. Piperidine rings are known for their basicity and can enhance the solubility of the molecule in aqueous environments. This can facilitate the molecule's passage through biological membranes.

The carboxamide group in the molecule is another important functional group. Carboxamides can form hydrogen bonds, which can influence the molecule's interaction with the artificial membrane and its overall permeability.

Overall, the combination of these functional groups suggests that the given molecule may exhibit moderate to high permeability in the PAMPA assay due to its lipophilic acetophenone moiety, the potential for hydrogen bonding and π-π interactions from the thiazole ring, and the solubility-enhancing properties of the piperidine ring.

Final answer: High permeability

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# 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 the lipid-rich environment of the artificial membrane.

The sulfonamide group, which is linked to the phenyl ring, is a polar functional group that can form hydrogen bonds with the membrane. This can increase the molecule's solubility in the membrane and facilitate its passage.

Overall, the combination of aromaticity, hydrophobic acetyl groups, and polar sulfonamide functionality suggests that the given molecule likely exhibits high permeability in the Parallel Artificial Membrane Permeability Assay.

Final answer: High permeability

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# 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 can introduce some degree of flexibility and steric hindrance, which might affect the molecule's overall shape and how it fits into the membrane. The presence of a methyl group on the pyrrolidine ring can also influence the molecule's lipophilicity, potentially enhancing its permeability.

4. **Carbonyl Group**: The methanone linkage introduces a carbonyl group, which can act as a hydrogen bond acceptor. This functional group can interact with the membrane, potentially aiding in the molecule's permeation.

5. **Overall Structure**: The combination of aromatic and heterocyclic rings, along with the carbonyl group, 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, as it possesses a combination of aromaticity, flexibility, and functional groups that facilitate interaction with 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:** 0

**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 potential impact on permeability:

1. **Pyrazolopyridazine Core**: The presence of a pyrazolopyridazine core is significant as it 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 nitrogen atoms in the pyrazole and pyridazine rings can participate in hydrogen bonding, which may facilitate interaction with the membrane.

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 solubility in the membrane environment, potentially increasing its permeability.

3. **Phenyl and Butoxyphenyl Groups**: The phenyl and butoxyphenyl groups add hydrophobic character to the molecule. These groups can interact with the hydrophobic regions of the artificial membrane, which may facilitate permeation. However, the presence of these groups can also lead to steric hindrance, which might reduce permeability.

4. **Methyl and Butoxy Substituents**: The methyl and butoxy substituents on the phenyl ring increase the molecule's lipophilicity. This can enhance the ability of the molecule to traverse the lipid-like environment of the artificial membrane, potentially increasing permeability.

Overall, the given molecule has a balance of polar and non-polar features, which suggests that it may have moderate permeability in the PAMPA assay. The pyrazolopyridazine core and carboxamide group can facilitate interaction with the membrane, while the phenyl and butoxyphenyl groups contribute to lipophilicity. 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.

------
# 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. 

Firstly, the presence of the piperazine ring, a six-membered ring containing two nitrogen atoms, is a significant 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.

Additionally, the molecule contains a methanone group, which is a carbonyl group (C=O) linked to a methylene bridge. This functional group can participate in hydrogen bonding and dipole-dipole interactions, which may also contribute to the molecule's permeability.

The 3,4,5-trimethoxyphenyl moiety introduces three methoxy groups attached to a phenyl ring. Methoxy groups are electron-donating and can increase the lipophilicity of the molecule, potentially enhancing its ability to permeate lipid membranes. However, the presence of these groups can also affect the molecule's overall polarity and solubility, which must be balanced when considering permeability.

The 2-chlorophenyl group introduces a chlorine atom to the phenyl ring, which can influence the molecule's electronic properties and lipophilicity. Chlorine is a relatively electronegative atom, and its presence can affect the molecule's ability to interact with the artificial membrane, potentially enhancing permeability due to increased lipophilicity.

Overall, the combination of these structural features suggests that the given molecule may exhibit high permeability in the PAMPA assay, as the balance of hydrophilic and lipophilic properties, along with the ability to form hydrogen bonds, supports efficient passage through the artificial membrane.

Final answer: High permeability.

------
# 293

**SMILES:** COC1=CC=CC(=C1)NC2=NC(=NC3=CC=CC=C32)C4=CC=NC=C4

**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, including anticancer and anti-inflammatory properties. The molecule contains several key structural features that influence its permeability.

Firstly, the quinazoline core is a bicyclic structure that contributes to the molecule's rigidity and planarity. This rigidity can enhance the molecule's ability to interact with biological membranes, as it can fit into the lipid bilayer more effectively than flexible molecules. The planar nature of the quinazoline ring system can also facilitate stacking interactions with aromatic amino acids in proteins, which may enhance binding affinity to biological targets.

Additionally, the molecule has a pyridinyl group attached to the quinazoline core. The presence of this nitrogen-containing heterocycle can increase the molecule's polarity and hydrogen bonding capacity, which may improve its solubility in aqueous environments and its ability to interact with polar sites on biological membranes.

The methoxyphenyl group attached to the nitrogen atom of the quinazoline ring introduces an electron-donating methoxy group. This can influence the electronic distribution across the molecule, potentially affecting its interaction with the artificial membrane. The methoxy group can also enhance the molecule's lipophilicity, which may facilitate its passage through the lipid-rich environment of the membrane.

Overall, the combination of the quinazoline core, pyridinyl group, and methoxyphenyl substituent suggests that the given molecule may exhibit high permeability in the PAMPA assay, as these structural features promote favorable interactions with the artificial membrane.

Final answer: High 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. The presence of these rings suggests that the molecule has a planar structure, which can facilitate interactions with the artificial membrane in the PAMPA assay.

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 permeate through the membrane.

Additionally, the molecule has a pyridine ring, which is another nitrogen-containing heterocycle. The presence of a methyl group on the pyridine ring can increase the lipophilicity of the molecule, potentially enhancing its permeability through the lipid-like environment of the artificial membrane.

The phenyl groups attached to the pyridine and pyrimidine rings contribute to the overall hydrophobic character of the molecule. These aromatic groups can engage in hydrophobic interactions with the membrane, further promoting permeability.

Overall, the combination of aromatic rings, heterocycles, and hydrophobic substituents suggests that the given molecule likely exhibits high permeability in the PAMPA assay.

Final answer: High permeability

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# 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 benzoate ester, which is a type of ester derived from benzoic acid. This structural feature suggests that the molecule has a relatively non-polar ester group, which can influence its permeability through the artificial membrane.

The presence of the pyrroloquinazoline moiety indicates a bicyclic structure that can contribute to the molecule's rigidity and potential interactions with the membrane. The dicyano groups attached to this moiety introduce polar characteristics, which can enhance the molecule's ability to form hydrogen bonds or dipole-dipole interactions with the membrane.

The amino group linked to the benzoate ester can also participate in hydrogen bonding, potentially increasing the molecule's solubility and permeability. However, the overall balance of hydrophobic and hydrophilic regions in the molecule will determine its permeability.

Considering these structural features, the given molecule is likely to exhibit moderate permeability due to the presence of both polar and non-polar regions, as well as the potential for hydrogen bonding and dipole interactions.

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:** 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 components and their potential impact on permeability:

1. **1,3-Oxazole Ring**: The presence of the 1,3-oxazole ring is significant as it is a heterocyclic aromatic compound. This ring can contribute to the molecule's overall stability and rigidity, which may enhance its ability to permeate the artificial membrane. Aromatic rings often facilitate interactions with the membrane through π-π stacking or other non-covalent interactions.

2. **Furan Ring**: The furan ring is another heterocyclic aromatic component. Like the oxazole ring, it can contribute to the molecule's aromatic character, potentially aiding in membrane permeability. The furan ring is relatively planar and can engage in π-π interactions, which may enhance the molecule's ability to traverse the membrane.

3. **Phenylmethoxyphenyl Group**: This group introduces a bulky, hydrophobic moiety to the molecule. The phenyl rings can participate in hydrophobic interactions with the membrane, which may facilitate permeation. The methoxy group can also contribute to the molecule's overall lipophilicity, enhancing its ability to pass through the lipid-like environment of the artificial membrane.

4. **Amino Group**: The presence of an amino group can introduce hydrogen bonding capabilities, which may affect the molecule's solubility and permeability. In the context of PAMPA, the amino group can form hydrogen bonds with the membrane, potentially aiding in permeation.

5. **Carbonitrile Group**: The carbonitrile group is a polar functional group that can engage in dipole-dipole interactions. While it may introduce some polarity to the molecule, its small size and linear structure might not significantly hinder permeability.

Overall, the given molecule contains a combination of aromatic and heterocyclic rings, hydrophobic groups, and polar functionalities. These features suggest that the molecule is likely to have high permeability in the PAMPA assay, as it can engage in various non-covalent interactions with the artificial membrane, facilitating its passage.

Final answer: High permeability

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# 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 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 potential impact on permeability:

1. **Triazoloquinazoline Core**: This bicyclic system is a key feature of the given molecule. Quinazolines are known for their planar aromatic structure, which can facilitate interactions with the artificial membrane. The triazole ring can contribute to the molecule's overall stability and rigidity, potentially enhancing its ability to permeate the membrane.

2. **Fluorophenyl Group**: The presence of a fluorine atom on the phenyl 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.

3. **Thioether Linkage**: The sulfanyl (thioether) linkage connects the triazoloquinazoline core to the butanamide moiety. Thioethers can influence the molecule's flexibility and overall conformation, which may affect its ability to permeate the membrane.

4. **Butanamide Moiety**: The amide group can form hydrogen bonds, which might interact with the artificial membrane. However, the presence of the butanamide group also introduces some polarity, which could reduce permeability compared to more lipophilic molecules.

5. **Dimethylpyrazole Group**: The pyrazole ring is another aromatic system that can contribute to the molecule's overall stability and lipophilicity. The dimethyl substitution increases the hydrophobic character of this group, potentially enhancing membrane permeability.

Overall, the given molecule contains several aromatic and lipophilic components, which suggest that it may have high permeability in the PAMPA assay. The combination of planar aromatic systems, fluorine substitution, and thioether linkage likely facilitates interactions with the artificial membrane, promoting 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 structure that includes a benzothiophene core, a furan ring, and a quinoline moiety. These structural features play a significant role in determining its permeability in the PAMPA assay.

The benzothiophene core is a bicyclic structure that combines a benzene ring with a thiophene ring. This core is known for its planar and aromatic nature, which can facilitate interactions with the artificial membrane, potentially enhancing permeability.

The furan ring is a five-membered aromatic heterocycle containing oxygen. Its presence can contribute to the molecule's overall polarity and ability to form hydrogen bonds, which may influence its interaction with the membrane and its permeability.

The quinoline moiety is another aromatic heterocycle, known for its planar structure and ability to participate in π-π stacking interactions. This can further enhance the molecule's ability to interact with the membrane, potentially increasing its permeability.

Overall, the combination of these aromatic and heterocyclic rings in the given molecule suggests that it may have a high degree of permeability in the PAMPA assay due to its ability to engage in various non-covalent interactions with the artificial membrane.

Final answer: High permeability.

------
# 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. 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 a thiazole ring, which is a five-membered ring containing both sulfur and nitrogen. This heterocyclic ring can contribute to the molecule's overall stability and ability to interact with biological targets, potentially enhancing its permeability.

Additionally, the presence of a chloro substituent on the phenyl ring can increase the lipophilicity of the molecule, which may improve its ability to permeate lipid membranes. However, the chloro group can also introduce steric hindrance, which might affect the molecule's overall permeability.

The benzamide moiety in the structure is a common feature in many bioactive compounds, often contributing to the molecule's ability to form hydrogen bonds with biological targets. This can enhance the molecule's interaction with the artificial membrane, potentially increasing its permeability.

Overall, the combination of these functional groups suggests that the given molecule may exhibit moderate to high permeability in the PAMPA assay, as the polar sulfonamide group and the lipophilic chloro substituent work together to balance solubility and membrane permeability.

Final answer: Low-to-moderate permeability.

------
# 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.

The molecule contains a cyclopenta[a]phenanthrene core, which is a hallmark of steroid structures. This core is relatively rigid and hydrophobic, which often facilitates the passage of steroid molecules through lipid membranes. The presence of the hydroxyimino group and the ethyl group attached to the steroid backbone can influence the molecule's polarity and solubility, potentially affecting its permeability.

The acetate ester group in the molecule can also play a role in its permeability. Ester groups can increase the lipophilicity of a compound, which may enhance its ability to permeate lipid membranes. However, esters can also be hydrolyzed in biological systems, which might affect the molecule's stability and permeability.

Overall, the combination of the steroid core, the hydroxyimino group, and the acetate ester suggests that the given molecule likely exhibits high permeability to the artificial membrane, as these features are generally conducive to membrane permeability.

Final answer: High permeability

------
# 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 on the benzopyran ring can enhance the molecule's ability to form hydrogen bonds, which may increase its solubility in water and potentially improve its permeability through the artificial membrane. However, the trimethyl groups attached to the pyran ring contribute to the molecule's hydrophobic character, which can hinder its permeability by reducing its solubility in the aqueous environment of the PAMPA.

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.

Final answer: Low-to-moderate permeability.

------
# 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 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 common pharmacophore in medicinal chemistry, often associated with good membrane permeability due to its planar aromatic structure. This allows the molecule to interact favorably with lipid membranes.

2. **Diethylsulfamoyl Group**: The presence of the diethylsulfamoyl group introduces a polar sulfonamide linkage. Sulfonamides are known to enhance water solubility, which can improve permeability by increasing the molecule's ability to interact with the aqueous environment of biological membranes.

3. **Cyano Group**: The cyano group is a polar functional group that can influence the molecule's electronic properties. While it may reduce lipophilicity, it can also participate in hydrogen bonding, potentially aiding in membrane permeability.

4. **Phenyl Ring**: The phenyl ring contributes to the overall hydrophobic character of the molecule, which can facilitate passage through lipid-rich environments like cell membranes.

Overall, the given molecule's structure suggests a balance between hydrophilic and hydrophobic properties, which is typical for molecules with moderate to high permeability in PAMPA assays. The combination of aromatic rings and polar functional groups likely allows the molecule to interact effectively with both lipid and aqueous phases, enhancing its permeability across the artificial membrane.

Final answer: High permeability

------
# 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 with several functional groups and structural features that influence its permeability in the PAMPA assay. Let's break down these features to understand its permeability:

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 increase the hydrophobic character of the molecule, which can enhance its ability to permeate lipid membranes. This group is likely to facilitate the molecule's interaction with the hydrophobic regions of the artificial membrane.

2. **Imidazo[1,2-a]pyridine Core**: This bicyclic structure is a heteroaromatic system that can contribute to the molecule's overall stability and rigidity. The presence of nitrogen atoms in the imidazo[1,2-a]pyridine core can also participate in hydrogen bonding or ionic interactions with the membrane, potentially affecting permeability.

3. **Amide Linkage**: The amide group in the molecule is a polar functional group that can form hydrogen bonds with the membrane. This can influence the molecule's solubility and permeability, potentially allowing it to interact with the membrane in a more polar environment.

4. **Methyl Ester Group**: The ester group in the molecule is another polar functional group that can also participate in hydrogen bonding. However, esters are generally more lipophilic than carboxylic acids, which may enhance the molecule's ability to permeate the membrane.

Overall, the given molecule has a combination of hydrophobic and polar features that suggest it may have moderate permeability in the PAMPA assay. The dichlorophenyl group increases lipophilicity, while the amide and ester groups provide opportunities for polar interactions with the membrane. These features together suggest that the molecule can traverse the artificial membrane, but the exact permeability would depend on the specific conditions of the assay and the nature of the membrane used.

Final answer: Low-to-moderate permeability.

------
# 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 potential impact on permeability:

1. **tert-Butyl Ester Group**: The presence of a tert-butyl ester group in the molecule suggests that it may have moderate to high lipophilicity. Ester groups can enhance the lipophilicity of a molecule, which can improve its ability to permeate lipid membranes. However, esters can also be susceptible to hydrolysis, which might affect the stability of the molecule in the PAMPA assay.

2. **Piperazine Ring**: The piperazine ring is a common structural motif in many pharmaceuticals and can contribute to the molecule's overall basicity. This basicity can enhance the molecule's solubility in aqueous environments, which is beneficial for permeability. Additionally, the piperazine ring can interact with the artificial membrane through hydrogen bonding or ionic interactions, potentially increasing permeability.

3. **Phenyl and Furan Rings**: The phenyl and furan rings provide aromatic character to the molecule, which can enhance lipophilicity. Aromatic rings can also participate in π-π interactions with the artificial membrane, potentially facilitating permeation. However, the presence of these rings might also lead to steric hindrance, which could impede permeability.

4. **Cyano Group**: The cyano group is a polar functional group that can increase the molecule's overall polarity. This can enhance solubility in aqueous environments, which is beneficial for permeability. However, the cyano group might also introduce some degree of polarity that could hinder permeability through the lipid-rich artificial membrane.

5. **Overall Structure**: The combination of these functional groups suggests that the given molecule has a balance of lipophilic and polar characteristics. The presence of the tert-butyl ester and aromatic rings likely contributes to moderate to high lipophilicity, while the piperazine and cyano groups provide some degree of aqueous solubility. This balance can result in moderate permeability through the artificial membrane, but the actual permeability would depend on the specific interactions between the molecule and the membrane.

Based on these structural features, the given molecule is likely to exhibit low-to-moderate permeability in the PAMPA assay.

Final answer: Low-to-moderate permeability.

------
# 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 properties.

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.

Additionally, the molecule contains an oxazole ring, which is a five-membered heterocyclic compound containing both oxygen and nitrogen. This ring can contribute to the molecule's overall stability and may also play a role in its ability to permeate the membrane due to its aromatic nature.

The cyclopropyl group is a small, three-membered ring 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 its permeability.

The presence of the methylphenyl group adds to the hydrophobic character of the molecule, which can further influence its permeability by promoting interactions with the lipid bilayer of the membrane.

Overall, the combination of these functional groups suggests that the given molecule is likely to have high permeability in the Parallel Artificial Membrane Permeability Assay (PAMPA).

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 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. **Aromatic Rings**: The molecule contains two aromatic rings, one with a bromo and a fluoro substituent, and the other with two methyl groups. Aromatic rings can enhance lipophilicity, which generally increases permeability through lipid membranes. However, the presence of halogen atoms like bromine and fluorine can also introduce polar characteristics, potentially affecting permeability by interacting with polar sites in the membrane.

2. **Piperidine Ring**: The presence of a piperidine ring, a six-membered nitrogen-containing heterocycle, can influence the molecule's basicity and solubility. Piperidine rings are often associated with increased permeability due to their ability to form hydrogen bonds and interact with polar sites in the membrane.

3. **Urea Linkage**: The urea linkage in the molecule can contribute to hydrogen bonding capabilities, which may enhance interaction with the membrane. Urea groups are often polar, which can affect the molecule's solubility and permeability.

4. **Alkyl Chains**: The molecule has alkyl chains connecting the aromatic rings and the piperidine ring. These chains can increase lipophilicity, which generally enhances membrane permeability. However, their length and flexibility can also affect how the molecule fits into the membrane.

Overall, the given molecule's structure suggests a balance of lipophilic and polar characteristics. The aromatic rings and alkyl chains contribute to lipophilicity, potentially enhancing permeability, while the piperidine ring and urea linkage introduce polar characteristics that can facilitate interaction with the membrane. The presence of halogen substituents may further modulate these interactions. Therefore, the given molecule is likely to exhibit high permeability in the PAMPA assay.

Final answer: High permeability

------
# 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 with several functional groups that influence its permeability in the PAMPA assay. Let's break down the structural components and their impact on permeability:

1. **Pyrazolopyridine 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 contribute to membrane permeability due to their ability to traverse lipid bilayers more efficiently.

2. **Furan Ring**: The presence of a furan ring, a five-membered aromatic heterocycle, can also contribute to the molecule's overall aromaticity and enhance its lipophilicity. This can improve the molecule's ability to penetrate the membrane by increasing its solubility in lipid environments.

3. **Ethyl Group**: The ethyl group attached to the pyrazolopyridine core increases the molecule's hydrophobic character, which can enhance its permeability by improving its ability to dissolve in lipid membranes.

4. **Cyano Group**: The cyano group is a polar functional group that can form hydrogen bonds with the artificial membrane. While it may introduce some polarity, its presence is relatively small compared to the overall hydrophobic character of the molecule.

5. **Methyl Group**: The methyl group contributes to the hydrophobic nature of the molecule, potentially enhancing its permeability by increasing its lipophilicity.

6. **Carboxylate Ester**: The ester group is a polar moiety that can participate in hydrogen bonding and dipole-dipole interactions with the membrane. However, in the context of PAMPA, esters are often hydrolyzed, which can affect the molecule's permeability.

Overall, the given molecule's combination of aromatic systems, hydrophobic groups, 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 lipid layer.

Final answer: High permeability

------
# 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 a class of compounds known for their potential biological activity. The structure of the given molecule includes a thieno[2,3-d]pyrimidine core, which is a bicyclic system combining a thiophene ring and a pyrimidine ring. This core is known for its rigidity and planarity, which can influence the molecule's ability to interact with biological membranes.

The presence of a fluorophenyl group attached to the thienopyrimidine core introduces a fluorine atom, which can enhance the molecule's lipophilicity. Fluorine is a small, highly electronegative atom that can increase the molecule's ability to penetrate lipid membranes by enhancing its hydrophobic interactions.

Additionally, the methylamino group contributes to the molecule's polarity and potential hydrogen bonding capabilities. This group can interact with the polar head groups of lipid bilayers, potentially facilitating membrane permeation.

Overall, the combination of the thienopyrimidine core, the fluorophenyl group, and the methylamino group suggests that the given molecule may exhibit moderate to high permeability in the PAMPA assay, as these structural features can enhance its ability to traverse the artificial membrane.

Final answer: High permeability

------
# 309

**SMILES:** C1CCN(CC1)C2=NC(=CS2)C3=CC=C(C=C3)Br

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a member of the thiazole family, characterized by a five-membered ring containing both sulfur and nitrogen atoms. This thiazole ring is known for its electron-rich nature, which can influence the molecule's interaction with biological membranes.

The molecule also contains a piperidine ring, a six-membered nitrogen-containing heterocycle, which is commonly found in many pharmacologically active compounds. The presence of the piperidine ring can enhance the molecule's solubility and ability to interact with biological targets, potentially increasing its permeability.

Additionally, the molecule features a bromophenyl group, which is a phenyl ring substituted with a bromine atom. The bromine atom can increase the lipophilicity of the molecule, which may enhance its ability to traverse lipid membranes. However, the presence of the bromine atom can also introduce steric hindrance, which might affect the molecule's overall permeability.

In the context of the Parallel Artificial Membrane Permeability Assay (PAMPA), the given molecule's structural features suggest that it may exhibit moderate permeability. The thiazole ring and piperidine moiety contribute to its potential permeability, while the bromophenyl group may enhance lipophilicity, balancing the overall permeability profile. Therefore, the given molecule is likely to have a low-to-moderate permeability in the PAMPA assay.

Final answer: Low-to-moderate permeability.

------
# 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 with several distinct structural features that influence its permeability in the PAMPA assay. Let's break down these features and their potential impact on permeability:

1. **Chlorine Substitution**: The presence of a chlorine atom on the pyridine ring can increase the lipophilicity of the molecule. Chlorine is a relatively electronegative atom, and its presence can enhance the molecule's ability to interact with lipid membranes, potentially increasing its permeability.

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. Pyridine rings are known for their ability to participate in π-π stacking interactions, which can facilitate the passage of the molecule through the artificial membrane.

3. **Benzoxazole Moiety**: The benzoxazole group is a bicyclic structure that can enhance the molecule's rigidity and planarity. This structural feature can improve the molecule's ability to traverse the membrane by allowing it to fit more snugly into the lipid bilayer.

4. **Triazole Ring**: The triazole ring is a five-membered heterocycle that can contribute to the molecule's overall stability and resistance to metabolic degradation. The presence of nitrogen atoms in the triazole ring can also enhance hydrogen bonding interactions, which may aid in the molecule's permeability.

5. **Tetrahydroquinazolinone Core**: The tetrahydroquinazolinone structure is a partially saturated heterocyclic compound that can influence the molecule's flexibility and conformational adaptability. This flexibility can be beneficial for the molecule to adopt a conformation that optimizes its interaction with the artificial membrane.

Overall, the combination of these structural features suggests that the given molecule is likely to exhibit high permeability in the PAMPA assay. The presence of lipophilic and aromatic groups, along with heteroatoms capable of forming hydrogen bonds, indicates that the molecule can effectively interact with the artificial membrane, facilitating its passage.

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 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 that can facilitate interactions with the artificial membrane. Aromatic rings often enhance lipophilicity, which can improve membrane permeability.

2. **Methoxy Group**: The presence of a methoxy group on the aromatic ring can increase the molecule's lipophilicity. This group can also participate in hydrogen bonding, which may affect the molecule's interaction with the membrane.

3. **Sulfonyl Group**: The sulfonyl group attached to the phenyl ring is a polar functional group that can enhance the molecule's solubility in aqueous environments. This group can also form hydrogen bonds, which may influence the molecule's orientation and interaction with the membrane.

4. **Pyrrole Ring**: The pyrrole ring is a heterocyclic aromatic compound that can contribute to the overall aromaticity of the molecule. This can enhance the molecule's ability to interact with the membrane through π-π stacking interactions.

5. **Morpholine Ring**: The morpholine ring is a heterocyclic amine that can increase the molecule's solubility and potentially improve its pharmacokinetic properties. The presence of this ring can also influence the molecule's ability to form hydrogen bonds with the membrane.

Overall, the given molecule's combination of aromatic rings, polar functional groups, and heterocyclic components suggests that it may have moderate to high permeability in the PAMPA assay. The balance of lipophilic and hydrophilic properties allows it to interact effectively with the artificial membrane, potentially facilitating its passage through the membrane.

Final answer: High permeability

------
# 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 through biological membranes.

The presence of the methyl groups on the benzene rings can increase the lipophilicity of the molecule, enhancing its ability to interact with lipid membranes. However, the overall size and complexity of the dibenzothiazepine core may limit its permeability due to steric hindrance and potential interactions with the artificial membrane.

The carboxamide group attached to the dibenzothiazepine core can form hydrogen bonds, which may facilitate interactions with the membrane or the artificial membrane used in the PAMPA assay. This functional group can also contribute to the molecule's solubility and permeability characteristics.

Considering these structural features, the given molecule is likely to exhibit low-to-moderate permeability in the PAMPA assay. This is due to the balance between its lipophilic aromatic rings and the polar carboxamide group, which may hinder its passage through the artificial membrane.

Final answer: Low-to-moderate permeability.

------
# 313

**SMILES:** C1CN(CCN1)C2=NC(=CS2)C3=CC=C(C=C3)Br

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a member of the thiazoles and contains a piperazine ring. The thiazole ring is a five-membered heterocyclic compound containing both sulfur and nitrogen atoms, which can contribute to the molecule's ability to interact with biological membranes. The presence of the piperazine ring, a six-membered ring containing two nitrogen atoms, can enhance the molecule's solubility and ability to form hydrogen bonds, potentially increasing its permeability.

The molecule also features a bromophenyl group, which is a phenyl ring substituted with a bromine atom. The bromine atom can increase the lipophilicity of the molecule, which may enhance its ability to permeate lipid membranes. However, the presence of the bromine atom can also introduce steric hindrance, which might affect the molecule's overall permeability.

Overall, the combination of the thiazole ring, piperazine ring, and bromophenyl group suggests that the given molecule may have moderate permeability due to the balance of hydrophilic and lipophilic properties. The piperazine and thiazole rings can facilitate interactions with the membrane, while the bromophenyl group may enhance lipophilicity, contributing to moderate permeability.

Final answer: Low-to-moderate permeability.

------
# 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 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 methoxyphenyl group attached to the benzimidazole core. The presence of the methoxy group can increase the lipophilicity of the molecule, potentially enhancing its ability to permeate lipid membranes.

The molecule also features a piperidine ring, which is a six-membered nitrogen-containing heterocycle. Piperidine rings are often found in pharmacologically active compounds and can contribute to the molecule's overall solubility and permeability.

The methanone linkage in the molecule connects the benzimidazole and piperidine moieties. This functional group can participate in hydrogen bonding and may influence the molecule's overall conformation and interaction with the artificial membrane.

In the context of the Parallel Artificial Membrane Permeability Assay (PAMPA), the given molecule's structural features suggest that it may exhibit moderate permeability. The benzimidazole core and methoxyphenyl group contribute to its lipophilicity, while the piperidine ring may enhance its solubility. These characteristics can facilitate the molecule's passage through the artificial membrane, but the overall permeability will depend on the balance between these factors and the specific conditions of the assay.

Final answer: Low-to-moderate permeability.

------
# 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 interact with metal ions and has been used in various applications, including as a chelating agent.

The molecule also contains a difluorophenyl group attached via a methylene bridge. The presence of fluorine atoms in the phenyl ring can significantly influence the molecule's lipophilicity and electronic properties. Fluorine is highly electronegative, which can enhance the molecule's ability to interact with biological membranes by increasing its hydrophobic character and potentially improving its ability to penetrate lipid bilayers.

The quinoline core, with its planar aromatic structure, can facilitate interactions with the artificial membrane through π-π stacking or hydrophobic interactions. The hydroxyl group on the quinoline ring can also form hydrogen bonds with the membrane, potentially enhancing permeability.

Overall, the combination of the quinoline core, the hydroxyl group, and the difluorophenyl moiety suggests that the given molecule may exhibit moderate to high permeability in the PAMPA assay, as these structural features can enhance its ability to 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:** 1

**Correct:** 1

# Response:
The given molecule is a member of the quinazolines, which are known for their 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 often associated with good pharmacokinetic properties, including membrane permeability.

The molecule also contains a methoxy group attached to a phenyl ring, which can enhance lipophilicity, potentially increasing membrane permeability. The presence of a benzyl group further contributes to the lipophilic character, which can facilitate passage through lipid membranes.

Additionally, the molecule features an acetamide group, which can form hydrogen bonds with the artificial membrane, potentially affecting its permeability. However, the overall structure suggests that the lipophilic components dominate, likely resulting in high permeability through the artificial membrane.

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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# 317

**SMILES:** CC(C)OC1=CC=CC(=C1)C2=CSC(=N2)N3CCC(CC3)C(=O)N

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a piperidinecarboxamide, which is characterized by the presence of a piperidine ring attached to a carboxamide group. This structure is known for its potential biological activity and is often used in pharmaceuticals.

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

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. Its presence often contributes to moderate permeability due to its balance of hydrophilic and lipophilic properties.

2. **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 may facilitate its passage through the membrane.

3. **Thiazole Ring**: The thiazole ring is a five-membered heterocycle containing both sulfur and nitrogen. This ring is relatively planar and can contribute to the molecule's overall rigidity. The presence of the thiazole ring can enhance the molecule's ability to penetrate the membrane due to its aromatic nature, which can interact with the lipid bilayer.

4. **Phenyl Group with an Ether Linkage**: The phenyl group is attached to the thiazole ring via an ether linkage, where the ether oxygen is connected to an isopropyl group. This ether linkage can increase the molecule's lipophilicity, which may enhance its ability to permeate the membrane. The isopropyl group can also contribute to the molecule's steric profile, potentially affecting its interaction with the membrane.

Overall, the given molecule's structure suggests that it may have moderate to high permeability in the PAMPA assay. The combination of the piperidine ring, thiazole ring, and phenyl group with an ether linkage likely provides a balance of hydrophilic and lipophilic properties, facilitating its passage through the artificial membrane.

Final answer: Low-to-moderate permeability.

------
# 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:** 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. **Aromatic Rings**: The molecule contains multiple aromatic rings, including a pyrimidine ring and phenyl rings. Aromatic rings can enhance lipophilicity, which generally increases membrane permeability. However, the presence of these rings can also lead to steric hindrance, potentially reducing permeability.

2. **Chloro Substituent**: The presence of a chloro group on the pyrimidine ring can increase the lipophilicity of the molecule, which may enhance permeability. However, the electronegative nature of chlorine can also affect the molecule's ability to interact with the membrane, potentially reducing permeability.

3. **Ether Linkage**: The ether linkage between the phenyl rings can contribute to the molecule's flexibility, which may facilitate its passage through the membrane. Ethers are generally polar, which can affect the balance between hydrophilicity and lipophilicity, potentially impacting permeability.

4. **Amine Group**: The presence of an amine group, particularly the piperazine moiety, can increase the molecule's hydrophilicity. This can enhance solubility in aqueous environments, which is beneficial for permeability. However, the basic nature of the amine can also lead to interactions with the membrane, potentially affecting permeability.

5. **Acryloyl Amide**: The acryloyl amide group introduces a degree of polarity and potential for hydrogen bonding, which can influence the molecule's interaction with the membrane. This group can also affect the overall stability and solubility of the molecule, impacting permeability.

Overall, the given molecule's structure suggests a balance between lipophilic and hydrophilic properties, with multiple aromatic rings and functional groups that can influence its permeability. The presence of both lipophilic and hydrophilic groups suggests that the molecule may have moderate permeability in the PAMPA assay, with potential for both high and low permeability depending on the specific interactions with the artificial membrane.

Final answer: Low-to-moderate permeability.

------
# 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 suggests that it contains an ester functional group derived from benzoic acid. This structural feature is often associated with moderate permeability in biological membranes due to the presence of both hydrophobic and hydrophilic regions.

The molecule has a complex structure with several functional groups that influence its permeability:

1. **Phenolic Hydroxyl Groups**: The presence of hydroxyl groups on the phenyl rings contributes to the molecule's hydrophilicity. These groups can form hydrogen bonds with the artificial membrane, potentially enhancing permeability by interacting with polar sites on the membrane.

2. **Methyl Group**: The methyl group on the pyrazole ring adds a degree of hydrophobicity, which can facilitate interaction with the lipid components of the artificial membrane. This balance of hydrophilic and hydrophobic regions is crucial for membrane permeability.

3. **Ester Linkage**: The ester linkage in the benzoate moiety can influence the molecule's lipophilicity, which is a key factor in permeability. Esters are generally more lipophilic than their corresponding acids, which can enhance the ability of the molecule to traverse lipid membranes.

4. **Pyrazole Ring**: The pyrazole ring is a heterocyclic aromatic compound that can contribute to the molecule's overall stability and ability to interact with the membrane. The aromatic nature of the pyrazole ring can facilitate π-π interactions with the membrane, potentially enhancing permeability.

Overall, the given molecule's combination of hydrophilic and hydrophobic groups, along with its aromatic and heterocyclic features, suggests that it would exhibit moderate permeability in the artificial membrane used in the PAMPA assay.

Final answer: Low-to-moderate permeability.

------
# 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, which can enhance the molecule's lipophilicity and metabolic stability. The fluorine atom can also influence the electronic properties of the phenyl ring, potentially affecting the molecule's binding affinity to biological targets.

In the context of the Parallel Artificial Membrane Permeability Assay (PAMPA), the given molecule's permeability is likely influenced by its overall lipophilicity, the presence of polar functional groups, and the ability of the thiazole and piperidine rings to interact with the artificial membrane. The carboxamide group can form hydrogen bonds, which may enhance the molecule's interaction with the membrane.

Overall, the combination of these structural features suggests that the given molecule may exhibit moderate permeability in the PAMPA assay, balancing lipophilic and hydrophilic interactions with the artificial membrane.

Final answer: Low-to-moderate permeability.

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# 321

**SMILES:** C1C(C2(CN1CC3=CC=C(C=C3)O)CN(C2)C4=CC=CC=C4)CNC5=CC=CC=C5

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a complex structure that includes several functional groups and structural features that influence its permeability. Let's break down these features to understand its permeability characteristics.

1. **Phenyl Groups**: The molecule contains multiple phenyl groups, which are aromatic rings. These rings can enhance the lipophilicity of the molecule, which generally increases its ability to permeate lipid membranes. However, the presence of these rings also means that the molecule may have significant steric hindrance, which can affect its ability to pass through the membrane.

2. **Diazaspiro Structure**: The spirocyclic structure, specifically the diazaspiro component, introduces rigidity and a unique three-dimensional shape to the molecule. This rigidity can affect the molecule's ability to fit into the membrane pores, potentially reducing its permeability. However, the spiro structure can also provide a specific orientation that might facilitate interaction with the membrane.

3. **Hydroxyl Group**: The presence of a hydroxyl group (–OH) in the molecule can increase its hydrophilicity, which might enhance its solubility in aqueous environments. This can improve the molecule's ability to interact with the polar head groups of the artificial membrane, potentially increasing its permeability.

4. **Aminomethyl Groups**: The aminomethyl groups introduce basic nitrogen atoms, which can form hydrogen bonds with the membrane. This can enhance the molecule's interaction with the membrane, potentially increasing its permeability. However, the basicity of these groups can also lead to ionization, which might affect the molecule's overall charge and, consequently, its permeability.

Overall, the given molecule's permeability is influenced by its lipophilic phenyl groups, the rigid and unique spirocyclic structure, and the hydrophilic and basic functional groups. These features suggest that the molecule may have moderate permeability, as the balance between lipophilicity and hydrophilicity, along with steric and electronic factors, will dictate its interaction with the artificial membrane.

Final answer: Low-to-moderate permeability.

------
# 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:** 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 membranes due to its polar nature.

In the given molecule, the presence of the sulfonamide group, specifically the 3-fluorobenzenesulfonamide moiety, suggests that it has polar characteristics, which can influence its permeability. The fluorine atom on the benzene ring can increase the molecule's lipophilicity, potentially enhancing its ability to permeate lipid membranes.

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 targets, potentially affecting its permeability.

The benzamide portion of the molecule, with its amide linkage, can also play a role in permeability. Amides are generally polar and can form hydrogen bonds, which may facilitate interaction with the artificial membrane.

Overall, the combination of these functional groups suggests that the given molecule may have moderate permeability due to the balance of polar and non-polar characteristics. The sulfonamide group contributes to polar interactions, while the aromatic and heterocyclic components may enhance lipophilicity, allowing the molecule to traverse the artificial membrane.

Final answer: Low-to-moderate permeability.

------
# 323

**SMILES:** C1=CSC(=C1)C2=NN=C(O2)NC(=O)C3=CC=C(C=C3)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 components to understand its permeability characteristics.

1. **Carbonyl Group**: The presence of the carbonyl group (C=O) in the benzamide moiety is a key feature. Carbonyl groups are polar, which can enhance the molecule's ability to interact with polar environments, such as the aqueous phase in biological systems. This polarity can facilitate the molecule's passage through the PAMPA membrane, contributing to its permeability.

2. **Amide Linkage**: The benzamide structure includes an amide linkage, which is a common feature in many bioactive molecules. Amides are generally stable and can form hydrogen bonds, which may help the molecule interact with the membrane and enhance its permeability.

3. **Chloro Substituent**: The chloro group on the benzene ring can influence the molecule's lipophilicity. Chlorine is a halogen that can increase the lipophilic character of the molecule, potentially enhancing its ability to traverse lipid membranes. However, it can also introduce steric hindrance, which might affect the molecule's overall permeability.

4. **Thiophene Ring**: The thiophene ring is a sulfur-containing heterocycle that can contribute to the molecule's overall lipophilicity. Thiophene rings are known for their ability to interact with lipid environments, which can enhance membrane permeability.

5. **Oxadiazole Ring**: The oxadiazole ring is a heterocyclic compound that can contribute to the molecule's stability and rigidity. This ring can also participate in hydrogen bonding and dipole interactions, which may aid in the molecule's permeability.

Overall, the given molecule contains a combination of polar and non-polar features, which suggests that it may have moderate permeability in the PAMPA assay. The presence of the carbonyl group and amide linkage can facilitate interactions with the aqueous phase, while the chloro substituent and thiophene ring can enhance lipophilicity, aiding in membrane permeability. However, the specific arrangement and interactions of these groups will ultimately determine the molecule's permeability profile.

Final answer: Low-to-moderate 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 typically consists of a methane group bonded to two aromatic rings. This structural feature can influence the molecule's permeability properties.

The presence of the diphenylmethane moiety, with two phenyl rings attached to a central carbon, suggests that the molecule has a relatively large and planar structure. This can enhance its ability to interact with the artificial membrane, potentially increasing its permeability. The aromatic rings can engage in π-π interactions with the membrane, which may facilitate passage through the membrane.

Additionally, the diazepan ring in the structure introduces a degree of flexibility and polarity to the molecule. The nitrogen atoms in the diazepan ring can form hydrogen bonds or ionic interactions with the membrane, which may also contribute to its permeability.

Overall, the combination of the aromatic rings and the diazepan ring suggests that the given molecule may exhibit high permeability in the Parallel Artificial Membrane Permeability Assay.

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 adamantanamine, which is known for its high lipophilicity and structural rigidity due to the adamantane framework. This structural feature often enhances the molecule's ability to permeate lipid membranes.

The molecule contains a hydroxyimino group, which can participate in hydrogen bonding, potentially affecting its interaction with the artificial membrane. However, the presence of the bulky adamantyl group is likely to dominate the molecule's behavior, promoting lipophilic interactions with the membrane.

Additionally, the phenyl groups in the structure contribute to the overall hydrophobic character, further supporting membrane permeability. The presence of a methylamino linkage suggests some degree of flexibility and potential for hydrogen bonding, but the overall structure is expected to favor lipophilic interactions.

Considering these structural elements, the given molecule is likely to exhibit high permeability in the artificial membrane, as the lipophilic and rigid nature of the adamantyl group and the phenyl rings dominate its interaction with the 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:** 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. **Aromatic Rings**: The molecule contains multiple aromatic rings, including a quinoline moiety 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 reducing permeability.

2. **Naphthyridine Core**: The naphthyridine structure is a bicyclic aromatic system that can contribute to the molecule's rigidity and planarity. This rigidity can affect how the molecule interacts with the artificial membrane, potentially enhancing permeability due to better alignment with the membrane.

3. **Oxan-4-yl Group**: The presence of an oxan-4-yl group introduces an ether linkage, which can increase the molecule's polarity. This can lead to moderate permeability as polar groups can form hydrogen bonds with the membrane, facilitating passage.

4. **2-Methylprop-2-ynyl Group**: This group contains an alkyne and a methyl branch, which can increase lipophilicity. The alkyne may also introduce some rigidity to the molecule, which can affect its interaction with the membrane.

5. **Cyanide Group**: The nitrile group (cyano group) is polar and can form hydrogen bonds or dipole-dipole interactions with the membrane. This can enhance permeability, but the overall effect will depend on the balance with other polar and nonpolar groups in the molecule.

Overall, the given molecule has a combination of lipophilic and polar features. The aromatic rings and naphthyridine core suggest a degree of lipophilicity, which can enhance permeability. However, the polar groups, such as the oxan-4-yl and cyano groups, may also contribute to moderate permeability by facilitating interactions with the membrane. Therefore, the given molecule is likely to exhibit low-to-moderate permeability in the PAMPA assay.

Final answer: Low-to-moderate 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 tricyclic framework, specifically a dibenzodiazepine core, which is a hallmark of this class. This core consists of two benzene rings fused to a seven-membered diazepine ring. 

The presence of the diazepine ring contributes to the molecule's ability to interact with various biological targets, such as neurotransmitter receptors in the central nervous system. The tricyclic structure is relatively rigid, which can influence the molecule's ability to cross biological membranes.

The molecule also features a chlorine atom attached to one of the benzene rings. This halogen substitution can enhance lipophilicity, potentially increasing the molecule's ability to permeate lipid membranes.

Additionally, the molecule contains a piperazine ring, which is a six-membered ring with two nitrogen atoms. This moiety can enhance solubility and may also contribute to the molecule's ability to interact with biological targets due to its basic nature, which can form hydrogen bonds or ionic interactions.

Overall, the combination of the tricyclic core, the chlorine substituent, and the piperazine ring suggests that the given molecule may exhibit moderate to high permeability in the PAMPA assay, as these structural features are commonly associated with enhanced membrane permeability.

Final answer: High permeability

------
# 328

**SMILES:** CCC1=CC=C(C=C1)NC(=O)C2=NN3C=CC=NC3=C2

**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 ring, specifically the 4-ethylphenyl group, contributes to the molecule's lipophilicity, which can enhance its ability to permeate through lipid membranes. Aromatic rings are known to interact with hydrophobic environments, which is a key factor in membrane permeability.

Additionally, the pyrazolo[1,5-a]pyrimidine core is a heterocyclic aromatic compound, which can also contribute to the molecule's overall lipophilicity. The nitrogen atoms in the heterocyclic ring can participate in hydrogen bonding, which may affect the molecule's interaction with the artificial membrane.

The carboxamide group in the molecule can form hydrogen bonds, which may influence the molecule's solubility and permeability. However, in this context, the aromatic and heterocyclic components are likely to dominate the permeability characteristics.

Overall, the given molecule's combination of aromatic and heterocyclic structures, along with the amide group, suggests that it would exhibit high permeability in the Parallel Artificial Membrane Permeability Assay.

Final answer: High permeability

------
# 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 biphenyl class, which indicates that it contains a biphenyl moiety. This structural feature is known for its hydrophobic character, which can influence the molecule's permeability.

The molecule also contains a cyclopropylmethyl group, which is a small, rigid, and hydrophobic moiety. This group can enhance the lipophilicity of the molecule, potentially increasing its ability to permeate through lipid membranes.

Additionally, the presence of a pyrazolo[1,5-a]pyrimidine core suggests a heterocyclic structure that can contribute to the molecule's overall stability and ability to interact with biological membranes. The pyrimidine ring is often involved in hydrogen bonding and other interactions, which can affect permeability.

Overall, the combination of the biphenyl moiety, cyclopropylmethyl group, and pyrazolo[1,5-a]pyrimidine core suggests that the given molecule may exhibit high permeability due to its hydrophobic and lipophilic characteristics, which facilitate passage through lipid membranes.

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 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.

Attached to the benzimidazole core is a tert-butyl group, which is a bulky alkyl group. This group can increase the lipophilicity of the molecule, potentially enhancing its ability to permeate lipid membranes. The presence of the tert-butyl group can also influence the molecule's steric properties, affecting how it fits into the membrane or interacts with other molecules.

Additionally, the molecule contains a piperidine moiety, which is a six-membered nitrogen-containing heterocycle. Piperidine rings are often found in pharmaceuticals due to their basicity and ability to form hydrogen bonds, which can improve the molecule's solubility and permeability.

The methanone linkage in the molecule connects the benzimidazole and piperidine components. This carbonyl group can participate in additional hydrogen bonding and dipole-dipole interactions, which may further influence the molecule's permeability.

Overall, the combination of the benzimidazole core, the lipophilic tert-butyl group, and the piperidine moiety suggests that the given molecule may have moderate to high permeability in the PAMPA assay, as these structural features can enhance its ability to interact with and permeate the artificial membrane.

Final answer: High permeability

------
# 331

**SMILES:** C1CN(CCC1C(=O)N)C2=NC(=CS2)C3=CC4=CC=CC=C4C=C3

**Label:** 1

**Predi:** 1

**Correct:** 1

# 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.

Firstly, the naphthalene moiety is a polycyclic aromatic hydrocarbon, which is known for its hydrophobic properties. This hydrophobicity can enhance the molecule's ability to interact with the lipid components of the artificial membrane, potentially increasing its permeability.

The thiazole ring is a heterocyclic compound containing both sulfur and nitrogen atoms. This ring can participate in hydrogen bonding and other polar interactions, which may influence the molecule's solubility and permeability. The presence of the thiazole ring can also contribute to the overall rigidity of the molecule, which might affect its ability to pass through the membrane.

The piperidine ring is a saturated nitrogen-containing heterocycle, which can enhance the molecule's solubility in water due to its basic nitrogen atom. This can improve the molecule's interaction with the aqueous environment of the PAMPA assay, potentially increasing its permeability.

Finally, the carboxamide group is a polar functional group that can form hydrogen bonds with the artificial membrane. This group can enhance the molecule's solubility and may also facilitate its interaction with the membrane, contributing to its permeability.

Overall, the combination of hydrophobic aromatic systems and polar functional groups in the given molecule suggests that it may exhibit high permeability in the PAMPA assay, as it can effectively interact with both the lipid and aqueous components of the membrane.

Final answer: High 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 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 heterocyclic compound containing nitrogen atoms. The presence of nitrogen atoms can enhance the molecule's ability to form hydrogen bonds, which may increase its interaction with the artificial membrane. This core structure is often associated with bioactive compounds, suggesting potential permeability.

2. **Dimethyl and Methylphenyl Substituents**: The dimethyl groups on the pyrazolo[1,5-a]pyrimidine core increase the hydrophobic character of the molecule. This hydrophobicity can enhance the molecule's ability to traverse lipid membranes, contributing to higher permeability. The methylphenyl group further adds to the hydrophobic nature, potentially improving membrane permeability.

3. **Propanamide Linkage**: The amide group in the propanamide linkage can participate in hydrogen bonding, which may facilitate interaction with the membrane. However, the overall effect of the amide group on permeability is balanced by the hydrophobic nature of the rest of the molecule.

4. **Fluorophenylmethyl Group**: The presence of a fluorine atom in the phenyl ring can influence the molecule's electronic properties, potentially affecting its interaction with the membrane. Fluorine can enhance the lipophilicity of the molecule, which may improve 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 combination of aromatic rings, nitrogen-containing heterocycles, and functional groups like amides and fluorophenyl groups contribute to its ability to interact with the artificial membrane, likely resulting in high permeability.

Final answer: High permeability

------
# 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 complex organic compound that includes several functional groups and structural features that influence its permeability in the PAMPA assay. 

The molecule contains a quinolinone core, which is a bicyclic structure consisting of a benzene ring fused to a pyridone ring. This core is known for its planar structure, which can facilitate interactions with the artificial membrane, potentially enhancing permeability. The presence of the quinolinone moiety often contributes to the molecule's ability to traverse biological membranes due to its aromatic nature and potential for π-π stacking interactions.

Attached to the quinolinone core is a butyl chain, which acts as a flexible linker. This chain can increase the molecule's lipophilicity, enhancing its ability to interact with the lipid components of the artificial membrane, thus potentially improving permeability.

The molecule also features a piperazine ring, which is a six-membered heterocyclic amine. Piperazine rings are known for their basicity and ability to form hydrogen bonds, which can influence the molecule's solubility and permeability. The presence of this ring can enhance the molecule's interaction with the membrane, potentially increasing permeability.

Additionally, the molecule contains a dichlorophenyl group. The presence of chlorine atoms can increase the lipophilicity of the molecule, which may enhance its ability to permeate the membrane. However, the dichlorophenyl group can also introduce steric hindrance, which might reduce permeability by limiting the molecule's ability to fit into the membrane pores.

Overall, the combination of these structural features suggests that the given molecule may exhibit moderate to high permeability in the PAMPA assay, as the balance of lipophilicity, aromaticity, and hydrogen bonding potential is favorable for membrane interaction.

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:** 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 to understand its 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 hydrophobic interactions, which are important for permeability.

2. **3-Methylphenyl Substituent**: Attached to the benzimidazole is a 3-methylphenyl group. The methyl group adds a degree of hydrophobicity to the molecule, which can enhance its ability to interact with the lipid components of the artificial membrane. The phenyl ring itself is also aromatic, contributing to the overall hydrophobic character of the molecule.

3. **Piperidine Ring**: The molecule also contains a piperidine ring, which is a six-membered nitrogen-containing heterocycle. Piperidine is a common motif in pharmaceuticals and can enhance the solubility of the molecule in aqueous environments. The presence of a methyl group on the piperidine ring can further increase the hydrophobicity and potentially affect the molecule's conformational flexibility.

4. **Methanone Linkage**: The methanone group (a carbonyl group) acts as a linker between the benzimidazole and the piperidine ring. The carbonyl group can participate in hydrogen bonding, which may influence the molecule's interaction with the artificial membrane. However, the presence of this group does not significantly increase the overall hydrophobicity of the molecule.

Overall, the given molecule exhibits a balance of hydrophobic and hydrophilic properties due to its aromatic rings, methyl groups, and piperidine ring. The combination of these features suggests that the molecule would have moderate permeability in the PAMPA assay, as it can interact with both the hydrophobic and hydrophilic components of the artificial membrane. However, the specific permeability would ultimately depend on the exact nature of the artificial membrane used in the assay.

Final answer: Low-to-moderate permeability.

------
# 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:** 0

**Correct:** 0

# 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 may have some degree of lipophilicity. Aromatic systems can enhance membrane permeability due to their ability to interact with lipid bilayers through π-π interactions and van der Waals forces.

2. **Bromo Substitution**: The bromine atom on the pyrrolo[2,3-d]pyrimidine ring can increase the molecule's lipophilicity, potentially enhancing its ability to permeate lipid membranes. However, it may also introduce steric hindrance, which could affect the molecule's overall permeability.

3. **Amino Group**: The presence of an amino group on the pyrrolo[2,3-d]pyrimidine ring can introduce hydrogen bonding capabilities, which may facilitate interactions with the artificial membrane. This can enhance permeability by allowing the molecule to form hydrogen bonds with the membrane's polar head groups.

4. **Sugar Moiety**: The oxolane ring, which is a sugar-like structure, is substituted with hydroxyl groups. These hydroxyl groups can form hydrogen bonds with the membrane, potentially increasing the molecule's solubility and permeability. The stereochemistry of the sugar moiety (indicated by the specific configuration of the chiral centers) can also influence the molecule's interaction with the membrane.

5. **Alkyl Chain**: The presence of a tert-butyl group attached to the urea moiety introduces significant steric bulk, which can affect the molecule's ability to fit into the membrane's lipid bilayer. This bulky group may hinder permeability by preventing the molecule from aligning properly with the membrane.

6. **Urea Linkage**: The urea linkage in the molecule can participate in hydrogen bonding, which may facilitate interactions with the membrane. However, the overall effect on permeability will depend on the balance between the hydrophilic and hydrophobic interactions.

Considering these structural features, the given molecule likely exhibits a combination of lipophilic and hydrophilic interactions with the artificial membrane. The balance of these interactions will determine its overall permeability. In general, the presence of aromatic and lipophilic groups suggests that the molecule may have moderate to high permeability, but the bulky tert-butyl group and the hydrophilic sugar moiety could reduce this permeability somewhat.

Final answer: Low-to-moderate permeability.

------
# 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 to understand its permeability characteristics.

1. **Trifluoromethyl Group**: The presence of a trifluoromethyl group on the pyrimidine ring contributes to the molecule's lipophilicity. This group is known to enhance the membrane permeability due to its ability to increase the molecule's overall hydrophobicity, which facilitates its passage through lipid membranes.

2. **Pyrimidine Ring**: The pyrimidine ring is a heterocyclic aromatic compound that can interact with the artificial membrane through π-π stacking interactions. This can enhance the molecule's permeability by stabilizing its interaction with the membrane.

3. **Sulfonyl Group**: The sulfonyl group attached to the pyrimidine ring 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 trifluoromethyl group, potentially allowing the molecule to maintain sufficient permeability.

4. **Thiophene Ring**: The thiophene ring is another aromatic heterocycle that can contribute to the molecule's overall stability and interaction with the membrane. Its presence may enhance the molecule's ability to permeate the membrane due to its planar structure and aromaticity.

5. **Propanamide Moiety**: The propanamide group introduces an amide linkage, which can participate in hydrogen bonding. This group may slightly reduce the overall permeability due to its polar nature, but its impact is likely mitigated by the other lipophilic components of the molecule.

6. **Phenoxy Group with Trifluoromethoxy Substitution**: The phenoxy group, particularly with a trifluoromethoxy substitution, adds to the molecule's lipophilicity and may enhance its ability to permeate the membrane. The trifluoromethoxy group is known for its electron-withdrawing properties, which can further stabilize the molecule's interaction with the membrane.

Overall, the given molecule exhibits a balance of lipophilic and polar characteristics, with several aromatic and electron-withdrawing groups that likely enhance its permeability through the artificial membrane. Therefore, the molecule is expected to have high permeability in the PAMPA assay.

Final answer: High permeability

------
# 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 structure that includes several key components influencing its permeability. Let's break down these components and their impact on permeability:

1. **Biphenyl Moiety**: The presence of a biphenyl group, which consists of two phenyl rings connected by a single bond, contributes to the molecule's hydrophobic character. This hydrophobicity can enhance the molecule's ability to interact with lipid membranes, potentially increasing its permeability through the artificial membrane.

2. **Thiazole Ring**: The thiazole ring is a five-membered heterocyclic compound containing both sulfur and nitrogen. This ring can introduce some degree of polarity and potential hydrogen bonding 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.

3. **Piperidine Ring**: The piperidine ring is a six-membered nitrogen-containing heterocycle. This ring is typically polar and can enhance the molecule's solubility in aqueous environments. The presence of the piperidine ring can also contribute to the molecule's ability to form hydrogen bonds, which may facilitate its interaction with the artificial membrane.

4. **Carboxamide Group**: The carboxamide group is a functional group that can participate in hydrogen bonding due to the presence of both a carbonyl group and an amine. This group can increase the molecule's polarity and solubility, which may enhance its permeability through the membrane.

Overall, the given molecule's structure suggests a balance of hydrophobic and polar characteristics. The biphenyl moiety likely enhances hydrophobic interactions, while the thiazole, piperidine, and carboxamide groups contribute to polar interactions. This combination of features suggests that the given molecule may exhibit high permeability through the artificial membrane, as it can effectively interact with both the hydrophobic and hydrophilic components of the membrane.

Final answer: High permeability.

------
# 338

**SMILES:** C1=CC=NC(=C1)C(=O)NC2=CC=C(C=C2)[S+](=O)(NC3=NC=CS3)[O-]

**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. This structural feature is significant in determining the molecule's permeability.

The presence of the aromatic rings, specifically the phenyl and pyridine rings, 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 amide linkage in the molecule contributes to its polarity and hydrogen bonding capability. Amides can form hydrogen bonds with the membrane, which may aid in the molecule's permeability. However, the amide group can also introduce some degree of rigidity and steric hindrance, potentially limiting the molecule's ability to permeate.

The thiazole ring, a five-membered heterocyclic ring containing both sulfur and nitrogen, adds to the molecule's heteroaromatic character. This can further influence the molecule's electronic properties and its ability to interact with the membrane.

Overall, the combination of aromatic rings and the amide linkage suggests that the given molecule may exhibit moderate permeability in the PAMPA assay. The balance between the planar aromatic structure and the polar amide group likely allows for sufficient interaction with the membrane, but may not be enough to achieve high permeability.

Final answer: Low-to-moderate permeability.

------
# 339

**SMILES:** CC1=CC=C(C=C1)C2=NC(=NC=C2)N3CCC(CC3)C(=O)N

**Label:** 1

**Predi:** 1

**Correct:** 1

# 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, potentially increasing its ability to permeate lipid membranes. The methyl group on the phenyl ring can further increase the hydrophobic character, which may facilitate passage through the lipid bilayer of the artificial membrane.

The piperidine ring is a saturated six-membered ring containing a nitrogen atom, which can contribute to the molecule's basicity and ability to form hydrogen bonds. This can affect the molecule's solubility and permeability, as the nitrogen can interact with the polar head groups of the artificial membrane.

Overall, the combination of the aromatic pyrimidine and phenyl groups, along with the piperidine ring, suggests that the given molecule may have moderate to high permeability in the PAMPA assay, as these structural features can enhance its ability to interact with and permeate the artificial membrane.

Final answer: High permeability

------
# 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 includes several functional groups and structural features that influence its permeability in the PAMPA assay. Let's break down these features to understand its permeability:

1. **Benzimidazole Moiety**: The presence of a benzimidazole ring is significant as it is a planar, aromatic structure that can interact with the artificial membrane through π-π stacking and hydrogen bonding. This can enhance the molecule's permeability by facilitating its passage through the membrane.

2. **Phenyl and Ethoxyphenyl Groups**: The phenyl and ethoxyphenyl groups contribute to the hydrophobic character of the molecule. These groups can interact with the lipid components of the artificial membrane, promoting permeability by increasing the molecule's affinity for the membrane's hydrophobic regions.

3. **Piperazinone Ring**: The piperazinone ring is a heterocyclic structure that can participate in hydrogen bonding and other polar interactions with the membrane. This can enhance the molecule's solubility and permeability, allowing it to traverse the membrane more efficiently.

4. **Ethyl Linker**: The ethyl linker between the phenyl group and the piperazinone ring provides flexibility and spatial separation, which can influence the molecule's ability to fit into the membrane's structure and pass through it.

Overall, the given molecule's combination of aromatic, hydrophobic, and heterocyclic features suggests that it would have high permeability in the PAMPA assay. The aromatic rings and heterocyclic components facilitate interactions with the membrane, while the hydrophobic groups enhance its ability to penetrate the lipid layers of the 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 derivative of proline, which is an amino acid known for its role in protein structure. The molecule contains several key structural features that influence its permeability:

1. **Indole Ring**: The presence of an indole moiety, which is a bicyclic structure consisting of a benzene ring fused to a pyrrole ring, contributes to the molecule's hydrophobic character. This can enhance the molecule's ability to interact with lipid membranes, potentially increasing its permeability.

2. **Indole Substitution**: The indole ring is substituted with a 1H-indol-3-yl group, which can further influence the molecule's interaction with the artificial membrane. The aromatic nature of the indole can facilitate π-π interactions with the membrane, potentially enhancing permeability.

3. **Proline Derivative**: As a proline derivative, the molecule has a cyclic structure that can impact its conformational flexibility. Proline's rigid ring structure can affect how the molecule fits into the membrane, potentially influencing permeability.

4. **Amide Linkage**: The presence of an amide bond (propanoyl amino linkage) contributes to the molecule's overall polarity and hydrogen bonding capacity. This can affect the molecule's solubility and permeability, as amide bonds can form hydrogen bonds with the membrane, potentially enhancing permeability.

5. **Ethylphenyl Group**: The ethylphenyl group adds additional hydrophobic character to the molecule. This can enhance the molecule's ability to embed within the lipid bilayer of the artificial membrane, potentially increasing permeability.

Overall, the combination of hydrophobic and aromatic groups, along with the cyclic structure of proline, suggests that the given molecule may have high permeability in the artificial membrane. The balance of hydrophobic and polar features allows it to interact effectively with the membrane, facilitating its passage.

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:** 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. **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. **Piperazine Ring**: The piperazine moiety is a common feature in many pharmaceuticals and can contribute to the molecule's solubility and permeability. The presence of this nitrogen-containing heterocycle can enhance the molecule's ability to interact with the membrane through hydrogen bonding or ionic interactions.

4. **Benzothiazine Core**: The benzothiazine structure is a bicyclic system that can contribute to the rigidity and overall shape of the molecule. This core can influence the molecule's ability to fit into the membrane's pores, potentially affecting its permeability.

5. **Carbonyl Group**: The carbonyl group in the molecule can participate in hydrogen bonding, which may facilitate interactions with the membrane. However, it can also introduce some degree of polarity, which might reduce permeability if it is not balanced by sufficient hydrophobic interactions.

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 fluorine substitution likely enhance its lipophilicity, while the piperazine and carbonyl groups provide opportunities for polar interactions. This combination of features suggests that the molecule would exhibit moderate permeability in the PAMPA assay.

Final answer: Low-to-moderate permeability.

------
# 343

**SMILES:** CCOC(=O)C1=C(C(=C(N1)C)CCC(=O)N2CCN(CC2)C3=CC=CC(=C3C)C)C

**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 to understand its permeability:

1. **Piperazine Ring**: The presence of a piperazine ring, which is a six-membered ring 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. **Dimethylphenyl Group**: The dimethylphenyl group is a phenyl ring substituted with two methyl groups. This hydrophobic aromatic group can enhance the lipophilicity of the molecule, which is often associated with increased membrane permeability. The presence of methyl groups can also affect the steric properties, potentially aiding in the passage through the membrane.

3. **Pyrrole Ring**: The pyrrole ring is a five-membered heterocyclic aromatic ring containing one nitrogen atom. Pyrrole rings can contribute to the overall aromaticity and electron-rich nature of the molecule, which may influence its interaction with the membrane. The presence of methyl groups on the pyrrole ring can further enhance lipophilicity.

4. **Ethyl Ester Group**: The ethyl ester group is an ester functional group attached to an ethyl chain. Esters are generally polar and can participate in hydrogen bonding, which may affect the solubility and permeability of the molecule. However, the ester group can also be hydrolyzed, which might influence the stability of the molecule in the PAMPA assay.

5. **Overall Structure**: The combination of these functional groups suggests that the given molecule has a balance of hydrophilic and hydrophobic properties. The piperazine and ester groups provide potential sites for hydrogen bonding and solubility, while the dimethylphenyl and pyrrole groups contribute to lipophilicity.

Considering these structural features, the given molecule is likely to exhibit moderate permeability in the PAMPA assay. The balance of hydrophilic and hydrophobic properties, along with the presence of functional groups that can interact with the artificial membrane, suggests that it can traverse the membrane to some extent, but may not be highly permeable due to the potential for interactions that could slow its passage.

Final answer: Low-to-moderate permeability.

------
# 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 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 potential impact on permeability:

1. **Benzothiazole Core**: The presence of a benzothiazole moiety, which is a bicyclic structure consisting of a benzene ring fused to a thiazole 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 due to favorable stacking interactions with the membrane components.

2. **Cyclopentyl Group**: The cyclopentyl 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 traverse lipid membranes, suggesting a higher permeability.

3. **Amide Linkages**: The molecule contains two amide groups, one as part of the benzamide structure and another as part of the acetamide moiety. Amide groups can form hydrogen bonds with the artificial membrane, which may facilitate interaction and permeation. However, they can also introduce some degree of polarity, which might limit permeability depending on the balance with other hydrophobic regions.

4. **Acetamide Group**: The acetamide group adds to the molecule's overall polarity and can participate in hydrogen bonding. This group may enhance solubility in aqueous environments, which is relevant for the PAMPA assay, but it might also limit permeability if it causes the molecule to interact too strongly with the aqueous phase rather than the membrane.

Overall, the given molecule's structure suggests a balance between hydrophobic and polar characteristics. The benzothiazole core and cyclopentyl group likely contribute to its lipophilicity, promoting permeability, while the amide linkages provide potential for hydrogen bonding with the membrane. This combination of features suggests that the molecule would exhibit high permeability in the PAMPA assay.

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 includes a piperidine ring attached to a carboxamide group. This structural feature is significant in drug design as piperidine rings often enhance the pharmacokinetic properties of a molecule, such as its ability to cross biological membranes.

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 ability to participate in hydrogen bonding and π-π interactions, which can influence the molecule's binding affinity and permeability.

Additionally, the presence of an acetylphenyl group introduces an aromatic ring with an acetyl substituent. This aromatic group can enhance the lipophilicity of the molecule, potentially increasing its ability to permeate lipid membranes.

Overall, the combination of these structural features suggests that the given molecule may exhibit high permeability in the PAMPA assay due to its lipophilic aromatic rings and the presence of functional groups that can interact with 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 potential 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 compound that can contribute to the molecule's overall planarity and rigidity. This structural feature can facilitate interactions with the artificial membrane, potentially enhancing permeability.

3. **Pyridine Ring**: The pyridine ring is another heterocyclic aromatic component that can also contribute to the molecule's lipophilicity and ability to interact with the membrane. The nitrogen atom in the pyridine ring can participate in hydrogen bonding, which may influence the molecule's orientation and interaction with the membrane.

4. **Propan-2-yl Group**: The isopropyl group attached to the pyrimidine ring introduces steric bulk and hydrophobic character to the molecule. This can enhance the molecule's ability to penetrate lipid membranes by increasing its lipophilicity.

5. **Amine Group**: The presence of an amine group in the pyrimidine ring can introduce basicity to the molecule, which may affect its solubility and permeability. Amines can form hydrogen bonds and ionic interactions with the membrane, potentially facilitating passage through the membrane.

Overall, the given molecule's combination of aromatic rings, fluorine substitution, and hydrophobic groups suggests that it may have a high degree of lipophilicity and the ability to interact favorably with the artificial membrane. This suggests that the molecule likely exhibits 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.

Additionally, the molecule features a pyrrolidinyl group. Pyrrolidine is a saturated five-membered ring containing a nitrogen atom, which can contribute to the molecule's basicity and ability to form hydrogen bonds. This group can increase the molecule's solubility and potentially improve its pharmacokinetic properties.

The combination of these functional groups suggests that the given molecule may have moderate permeability through the artificial membrane. The aromatic and heterocyclic components can facilitate interactions with the membrane, while the pyrrolidinyl group may enhance solubility and permeability. However, the overall permeability will depend on the balance between these interactions and the hydrophilic or lipophilic nature of the entire molecule.

Final answer: Low-to-moderate permeability.

------
# 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 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 ring containing two nitrogen atoms, is known to enhance the molecule's solubility and permeability. Piperazine rings are often found in pharmaceuticals due to their ability to improve the pharmacokinetic properties of a compound.

2. **Methoxyphenyl Group**: The methoxy group attached to the phenyl ring can increase the lipophilicity of the molecule. This can enhance the ability of the molecule to traverse lipid membranes, contributing to its permeability.

3. **Quinoline Moiety**: The quinoline structure is a bicyclic aromatic compound that can interact with biological membranes. Quinoline derivatives are known for their ability to penetrate cell membranes, which may contribute to the molecule's permeability.

4. **Sulfonyl Group**: The sulfonyl group is a polar functional group that can enhance the molecule's solubility in aqueous environments. This group can also participate in hydrogen bonding, which may facilitate interactions with the artificial membrane.

5. **Piperidine Ring**: The piperidine ring is a saturated six-membered ring containing a nitrogen atom. This structure is commonly found in bioactive compounds and can contribute to the molecule's overall stability and 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 lipophilic and hydrophilic components, along with the presence of nitrogen-containing rings, supports its ability to interact favorably with the artificial 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 ability to interact with biological membranes due to its planar aromatic structure. This class of compounds often exhibits good permeability due to their ability to traverse lipid bilayers.

The molecule contains a benzimidazole core, which is a bicyclic structure consisting of a benzene ring fused to an imidazole ring. This core is known for its stability and ability to engage in hydrogen bonding and π-π interactions, which can enhance membrane permeability.

Additionally, the molecule has an amino group attached to a phenoxy moiety. The presence of the amino group can increase the molecule's polarity, potentially improving its solubility in aqueous environments and facilitating its interaction with the polar head groups of the artificial membrane.

The cyclohexanecarboxamide moiety introduces a flexible, non-aromatic ring that can increase the molecule's overall hydrophobic character. This can enhance its ability to embed within the lipid-like environment of the artificial membrane.

Overall, the combination of the benzimidazole core, the amino group, and the cyclohexanecarboxamide moiety 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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# 350

**SMILES:** CN1C=CC2=C1C=CC(=C2)C3=CSC(=N3)N4CCC(CC4)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. This structure 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 molecule's permeability is determined by its ability to pass through a synthetic membrane that mimics biological membranes. The permeability is influenced by several factors, including the molecule's lipophilicity, size, and the presence of functional groups that can interact with the membrane.

For the given molecule, the presence of the indole ring, which is a bicyclic structure consisting of a benzene ring fused to a pyrrole ring, contributes to its lipophilicity. This can enhance the molecule's ability to interact with lipid membranes, potentially increasing its permeability.

Additionally, the thiazole ring, which is a five-membered ring containing both sulfur and nitrogen, can also contribute to the molecule's overall lipophilicity and electronic properties. The thiazole ring can participate in hydrogen bonding and other interactions with the membrane, which may further influence permeability.

The piperidine ring, being a six-membered nitrogen-containing heterocycle, can enhance the molecule's solubility and may also play a role in its ability to interact with biological targets. The carboxamide group can form hydrogen bonds, which may affect the molecule's interaction with the membrane and its overall permeability.

Overall, the combination of these structural features suggests that the given molecule may exhibit 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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# 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 potential impact on permeability:

1. **Aromatic Amine Group**: The presence of an aromatic amine, specifically the phenyl group attached to the nitrogen atom, contributes to the molecule's ability to participate in π-π interactions and hydrogen bonding. This can enhance the molecule's solubility and interaction with the artificial membrane, potentially increasing its permeability.

2. **Thiazole Ring**: The thiazole ring is a heterocyclic compound containing both sulfur and nitrogen. This ring can contribute to the molecule's overall stability and lipophilicity, which may facilitate its passage through the lipid-like environment of the artificial membrane.

3. **Pyrimidine Ring**: The pyrimidine ring is another heterocyclic component that can enhance the molecule's ability to interact with biological membranes. The nitrogen atoms in the pyrimidine ring can participate in hydrogen bonding, which may aid in the molecule's permeation.

4. **Isobutyl Group**: The isobutyl group, attached to the nitrogen atom, is a hydrophobic alkyl chain that can increase the lipophilicity of the molecule. This hydrophobic character can enhance the molecule's ability to traverse the lipid bilayer of the artificial membrane.

Overall, the combination of aromatic, heterocyclic, and hydrophobic components in the given molecule suggests that it may have a high permeability in the PAMPA assay. The aromatic amine and thiazole ring can facilitate interactions with the membrane, while the pyrimidine ring and isobutyl group contribute to the molecule's lipophilicity, enhancing its permeability through the artificial membrane.

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 compound that includes several distinct structural features, each contributing to its permeability characteristics in the PAMPA assay.

1. **Piperazine Ring**: The presence of a piperazine ring, which is a six-membered ring containing two nitrogen atoms, is known to enhance the molecule's solubility and permeability. Piperazine rings are often found in pharmaceuticals due to their ability to improve bioavailability. In this molecule, the piperazine ring is substituted with a methoxyphenyl 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, aiding in its ability to traverse lipid membranes. The presence of phenyl groups can also facilitate π-π interactions with the artificial membrane, potentially enhancing permeability.

3. **Thiadiazole Ring**: The thiadiazole ring is a five-membered heterocyclic compound containing both sulfur and nitrogen atoms. This ring can contribute to the molecule's electronic properties, potentially affecting its interaction with the membrane. The thiadiazole ring is often associated with increased metabolic stability, which may indirectly influence permeability by prolonging the molecule's presence in the system.

4. **Methoxy Group**: The methoxy group attached to the phenyl ring can increase the molecule's lipophilicity, which is beneficial for membrane permeability. Methoxy groups can also participate in hydrogen bonding, which may influence the molecule's 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 presence of lipophilic aromatic rings, a piperazine moiety, and a thiadiazole ring all contribute to its ability to traverse the artificial membrane, making it a candidate for further drug development studies.

Final answer: High permeability

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# 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 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. **Fluorophenyl Group**: The presence of a fluorine atom on the phenyl 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. **Benzamide Moiety**: The benzamide group is a polar functional group that can form hydrogen bonds. This can influence the molecule's solubility and permeability, as it may interact with the polar components of the artificial membrane.

3. **Pyridine Ring**: The pyridine ring is a heteroaromatic structure that can contribute to the molecule's overall polarity. The nitrogen atom in the pyridine ring can participate in hydrogen bonding and other polar interactions, which may affect the molecule's permeability.

4. **Piperazine Ring**: The piperazine ring is a flexible, nitrogen-containing heterocycle that can enhance the molecule's solubility and permeability. The presence of nitrogen atoms in the piperazine ring can facilitate interactions with the artificial membrane, potentially increasing 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 molecule's ability to fit into the membrane and its overall conformational dynamics.

Overall, the given molecule contains a combination of lipophilic and polar features that suggest it may have moderate to high permeability in the PAMPA assay. The balance of hydrophobic and hydrophilic interactions, along with the presence of aromatic and heterocyclic rings, likely allows the molecule to traverse the artificial membrane effectively.

Final answer: High permeability

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# 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 potential impact on permeability:

1. **Phenolic Group**: The presence of a phenolic group, which is a hydroxyl group attached to a benzene ring, can enhance the molecule's polarity. This can increase the molecule's solubility in aqueous environments, which is beneficial for permeability through the PAMPA membrane, which is designed to mimic biological membranes.

2. **Fluorophenyl Group**: The fluorophenyl group introduces a fluorine atom into the aromatic ring. Fluorine is highly electronegative, which can affect the electronic distribution of the molecule. This can influence the molecule's lipophilicity and its ability to interact with the membrane, potentially enhancing permeability due to increased membrane affinity.

3. **Cyclopropylmethyl Group**: The cyclopropylmethyl group is a small, non-polar moiety that can increase the lipophilicity of the molecule. This can enhance the molecule's ability to traverse lipid membranes, contributing to its permeability.

4. **Dihydropyridopyridine Moiety**: The dihydropyridopyridine structure is a bicyclic system that can contribute to the rigidity and planarity of the molecule. This structural feature can affect how the molecule fits into the membrane, potentially facilitating or hindering permeability depending on the orientation and interaction with the membrane.

Overall, the given molecule contains a combination of polar and non-polar groups, as well as aromatic and aliphatic components, which collectively influence its permeability. The balance of these features suggests that the molecule may exhibit moderate to high permeability in the PAMPA assay, as it has both hydrophilic and hydrophobic characteristics that can interact favorably with the artificial membrane.

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 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 known to enhance lipophilicity. This increased lipophilicity can facilitate the passage of the molecule through the lipid-like environment of the artificial membrane, suggesting high permeability.

2. **Pyridine Ring**: The pyridine ring is a heteroaromatic structure that can participate in hydrogen bonding and other polar interactions. While it may introduce some polarity, its aromatic nature can still allow the molecule to interact favorably with the membrane, contributing to its overall permeability.

3. **Thiazole Ring**: The thiazole ring is another heteroaromatic component that can engage in polar interactions. The presence of nitrogen and sulfur in the ring can enhance the molecule's ability to form hydrogen bonds and coordinate with polar sites on the membrane, potentially increasing its permeability.

4. **Sulfonyl Group**: The sulfonyl group is a strong electron-withdrawing group that can increase the molecule's polarity. This group can enhance the molecule's ability to interact with polar sites on the membrane, potentially improving its permeability.

5. **Carboxamide Group**: The carboxamide group is a polar functional group that can form hydrogen bonds. This group can interact with polar sites on the membrane, potentially aiding in the molecule's permeability.

Overall, the given molecule's combination of lipophilic biphenyl and polar functional groups suggests that it 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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# 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:** 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 typically enhances the molecule's ability to interact with biological membranes, as it can form hydrogen bonds and engage in polar interactions. This can contribute to the molecule's permeability across biological membranes.

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 molecule also features a benzyl group, which is a hydrophobic moiety that can further increase lipophilicity, potentially improving membrane permeability.

However, the presence of a fluorophenyl group introduces a polar fluorine atom, which can affect the overall polarity of the molecule. While fluorine can enhance metabolic stability and binding affinity, it may also reduce permeability due to its electronegativity and ability to form strong hydrogen bonds.

Overall, the combination of these functional groups suggests that the given molecule may have moderate permeability due to the balance between hydrophobic and hydrophilic characteristics. The sulfonamide group and the chloro substituent likely contribute to its ability to permeate the artificial membrane, while the fluorophenyl group may introduce some limitations.

Final answer: Low-to-moderate permeability.

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# 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 ability to permeate biological membranes. The sulfonamide group is a key feature that contributes to the molecule's permeability. This group is known for its polar nature, which can enhance the molecule's ability to interact with polar environments, such as those found in biological membranes.

The presence of the cyclopropane ring in the molecule can also influence its permeability. Cyclopropane rings are small and rigid, which can affect the overall shape and flexibility of the molecule. This rigidity can sometimes enhance membrane permeability by reducing the molecule's overall size and allowing it to fit more easily into the membrane's lipid bilayer.

Additionally, the aromatic ring systems, such as the phenyl group, can contribute to the molecule's ability to permeate membranes. Aromatic rings can engage in π-π interactions with the lipid components of the membrane, which can facilitate the molecule's passage through the membrane.

Overall, the combination of these structural features suggests that the given molecule likely has high permeability to the artificial membrane used in the PAMPA assay.

Final answer: High permeability

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# 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 member of the triazole family, which is known for its diverse biological activities and potential pharmaceutical applications. The structure of the given molecule includes a triazole ring, which is a five-membered ring containing three nitrogen atoms. This triazole ring is connected to a tricyclic system, which consists of a fused ring structure that includes a pyrrole and a diazatricyclo system. 

The presence of the triazole ring is significant because it often contributes to the molecule's ability to interact with biological targets, such as enzymes or receptors, due to its electron-rich nature and potential to form hydrogen bonds. The triazole ring can also enhance the molecule's stability and resistance to metabolic degradation.

The molecule also features a 3-chlorophenyl group attached to the triazole ring. The presence of the chlorophenyl group can influence the molecule's lipophilicity, which is a key factor in determining its ability to permeate biological membranes. The chlorophenyl group can increase the molecule's hydrophobic character, potentially enhancing its ability to pass through lipid-rich environments, such as cell membranes.

Additionally, the presence of methyl groups on the pyrrole ring can further influence the molecule's lipophilicity and steric properties. These methyl groups can increase the overall hydrophobicity of the molecule, which may aid in membrane permeability.

Overall, the combination of the triazole ring, the chlorophenyl group, and the methyl groups suggests that the given molecule may exhibit high permeability to the artificial membrane, as these structural features are likely to enhance its ability to interact with and permeate lipid-rich environments.

Final answer: High permeability.

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# 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 a dimethyl-substituted furan ring indicates that the molecule has a degree of hydrophobicity. Furan rings are aromatic and contribute to the overall lipophilicity of the molecule, which can enhance its ability to permeate lipid membranes. The dimethyl groups further increase the hydrophobic character, potentially improving membrane permeability by increasing the molecule's affinity for lipid bilayers.

Secondly, the molecule contains a trifluoromethyl group attached to a phenyl ring. The trifluoromethyl group is highly electronegative and can influence the molecule's electronic properties. This group can enhance the molecule's lipophilicity while also affecting its metabolic stability and membrane permeability. The presence of this group can increase the molecule's ability to interact with lipid membranes, potentially improving its permeability.

The tricyclic structure, which includes a triazolopyridine moiety, adds to the complexity of the molecule. The triazole ring is a five-membered heterocycle containing nitrogen atoms, which can participate in hydrogen bonding and other polar interactions. This can affect the molecule's solubility and permeability, potentially allowing it to interact with polar sites on the artificial membrane.

Overall, the combination of hydrophobic and polar features in the given molecule suggests that it may have moderate to high permeability in the PAMPA assay. The balance of lipophilic and polar characteristics allows the molecule to interact effectively with the artificial membrane, facilitating its passage through the membrane.

Final answer: High permeability.

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# 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 hydroxylated benzamide derivative with a chloro substituent and a pyridinylmethylamino group. The presence of these functional groups can influence its permeability in the PAMPA assay.

The hydroxyl group on the benzene ring can form hydrogen bonds, which may enhance the molecule's solubility and interaction with the artificial membrane. However, it can also introduce steric hindrance, potentially affecting the molecule's ability to permeate the membrane.

The chloro substituent on the benzene ring is a small, electronegative group that can influence the molecule's lipophilicity. Chlorine atoms can increase the molecule's ability to interact with lipid membranes, potentially enhancing permeability.

The pyridinylmethylamino group introduces a basic nitrogen atom, which can participate in ionic interactions with the membrane. This group may also contribute to the molecule's overall polarity, affecting its permeability.

Overall, the combination of these functional groups suggests that the given molecule may exhibit moderate permeability in the PAMPA assay, balancing between hydrophilic and lipophilic interactions.

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 properties, which can enhance the molecule's ability to interact with lipid membranes. The presence of the methoxy group can also influence the electronic distribution across 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 accept protons. This basic nature can facilitate interactions with acidic environments, such as those found in biological membranes, potentially enhancing permeability.

Additionally, the molecule features a thienopyridine moiety, which is a bicyclic structure combining a thiophene and a pyridine ring. The thiophene ring is a sulfur-containing heterocycle, which can contribute to the molecule's overall lipophilicity. The pyridine ring, being aromatic and nitrogen-containing, can also influence the molecule's electronic properties and solubility.

The methanone linkage in the molecule acts as a carbonyl group, which can participate in hydrogen bonding and other polar interactions. This functional group can affect the molecule's overall polarity and its ability to permeate through the membrane.

In summary, the given molecule's permeability in the PAMPA assay is likely influenced by its aromatic and heterocyclic structures, which contribute to its hydrophobic and lipophilic characteristics. The presence of the methoxy group and piperazine ring may enhance its ability to interact with lipid membranes, while the methanone linkage can influence its polarity. Overall, these structural features suggest that the molecule may exhibit high permeability in the PAMPA assay.

Final answer: High permeability

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# 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 phenyl 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 thiazole ring, and a pyridine ring. These rings can enhance the molecule's lipophilicity, which can improve 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 amide linkage in the molecule contributes to its overall polarity and ability to form hydrogen bonds. This can affect the molecule's solubility and permeability, often resulting in moderate permeability due to the balance between hydrophilic and lipophilic properties.

4. **Methoxy Group**: The methoxy group on the phenyl ring can increase the molecule's lipophilicity, potentially enhancing its permeability through lipid membranes. However, it also adds to the overall polarity of the molecule, which can affect its solubility and permeability.

Overall, the given molecule is likely to exhibit moderate permeability due to the interplay between its hydrophilic and lipophilic components. The sulfonamide group, along with the aromatic and amide functionalities, suggests that the molecule can interact with both polar and non-polar environments, which is typical for compounds with moderate permeability in PAMPA assays.

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 to understand its 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 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 components of the artificial membrane. The phenol group, on the other hand, can form hydrogen bonds, which may also facilitate interaction with the membrane.

3. **Imidazo[4,5-b]pyridine Moiety**: This bicyclic heteroaromatic system is known for its planar structure and ability to participate in π-π stacking interactions. The presence of nitrogen atoms in the imidazo[4,5-b]pyridine ring can also contribute to hydrogen bonding and ionic interactions, which may affect the molecule's permeability.

4. **Amino Methyl Linkage**: The amino group linked to a methyl group can enhance the molecule's ability to form hydrogen bonds and ionic interactions with the artificial membrane. This can increase the molecule's solubility and permeability.

5. **Chirality**: The given molecule has several chiral centers, which can influence its three-dimensional shape and how it interacts with the artificial membrane. The specific stereochemistry may affect the molecule's ability to fit into the membrane's structure, impacting its permeability.

Overall, the combination of these structural features suggests that the given molecule has a balance of hydrophilic and hydrophobic properties, which can facilitate its interaction with the artificial membrane. This balance, along with the potential for hydrogen bonding and ionic interactions, likely results in a high permeability in the PAMPA assay.

Final answer: High permeability

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# 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 break down the structural components and their impact on permeability:

1. **Quinoline Core**: The quinoline structure is a bicyclic aromatic compound that contributes to the molecule's planarity and rigidity. This planar structure can facilitate interactions with the artificial membrane, potentially enhancing permeability. Quinoline derivatives are often known for their ability to penetrate biological membranes due to their aromatic nature.

2. **Carboxamide Group**: The presence of a carboxamide group introduces hydrogen bonding capabilities. This functional group can form hydrogen bonds with the artificial membrane, which may enhance the molecule's interaction with the membrane and improve permeability. However, the carboxamide group can also introduce some polarity, which might reduce permeability depending on the balance with other hydrophobic parts of the molecule.

3. **Sulfamoyl Group**: The sulfamoyl group is a sulfonamide derivative, which is known for its ability to form strong hydrogen bonds. This group can enhance the molecule's solubility and interaction with the membrane, potentially increasing permeability. However, the sulfonamide moiety can also introduce some polarity, which might affect permeability.

4. **3,5-Dimethylphenoxy Moiety**: The dimethylphenoxy group is a hydrophobic aromatic moiety that can enhance the lipophilicity of the molecule. This increased lipophilicity can improve the molecule's ability to permeate the artificial membrane, as it can better interact with the lipid components of the membrane.

5. **Furan-2-ylmethyl Group**: The furan ring is a heteroaromatic moiety that can contribute to the molecule's overall aromaticity and planarity. This can enhance membrane permeability by facilitating interactions with the membrane. Additionally, the furan ring can introduce some polarity, which might affect the balance between hydrophilicity and lipophilicity.

Overall, the given molecule has a combination of aromatic and polar functional groups that suggest a balance between hydrophilic and lipophilic properties. The quinoline core, along with the hydrophobic and aromatic moieties, likely contribute to high permeability in the PAMPA assay, while the polar groups may provide some interaction with the membrane. Therefore, the given molecule is expected to have high permeability in the PAMPA assay.

Final answer: High permeability

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# 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:** 1

**Correct:** 1

# 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 structural elements and their potential 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 contribute to the molecule's rigidity and planarity, potentially enhancing its ability to interact with the artificial membrane. Conjugated systems can also influence the electronic properties of the molecule, which may affect its interaction with 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. This can facilitate the molecule's interaction with the polar head groups of the artificial membrane, potentially increasing its permeability.

3. **Amide Linkage**: The amide group in the molecule can form hydrogen bonds with the membrane, which may stabilize the interaction between the molecule and the membrane. This can contribute to the molecule's permeability by allowing it to remain associated with the membrane surface.

4. **Bicyclic Structure**: The bicyclic structure, specifically the oxabicycloheptene moiety, adds to the rigidity of the molecule. This rigidity can help the molecule maintain a specific conformation that may be favorable for interaction with the membrane.

5. **Keto Groups**: The presence of keto groups can also contribute to the molecule's ability to form hydrogen bonds with the membrane. These groups can enhance the molecule's interaction with the membrane, potentially increasing its permeability.

Overall, the given molecule's combination of conjugated systems, hydroxy and keto groups, and amide linkages suggests that it may have a favorable interaction with the artificial membrane, leading to high permeability. The rigidity and planarity introduced by the conjugated triene and bicyclic structures further support this potential.

Final answer: High 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:** 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. **Imidazo[1,2-a]pyrazine 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. **Benzyl Group**: The presence of a benzyl group introduces a hydrophobic moiety, which can increase the molecule's lipophilicity. This can enhance membrane permeability as lipophilic compounds tend to partition into lipid bilayers more readily.

3. **Phenylmethoxyphenyl Group**: This group contributes additional aromatic character and hydrophobicity. The methoxy group can also introduce some degree of polarity, which might help in balancing the overall lipophilicity of the molecule. The presence of two aromatic rings can further facilitate interactions with the membrane.

4. **2-Methoxyethyl Side Chain**: This side chain introduces some polarity due to the ether linkage, which can enhance solubility in aqueous environments. This may help the molecule to interact with the polar head groups 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 lipophilic and hydrophilic character. This balance is often associated with moderate permeability in PAMPA assays, as it allows the molecule to interact with both the lipid and aqueous phases of the membrane.

Based on these structural features, the given molecule is likely to exhibit low-to-moderate permeability in the PAMPA assay. This is because its balanced lipophilicity and hydrophilicity allow it to interact with the artificial membrane, but not so strongly that it becomes trapped in the membrane or exhibits high resistance.

Final answer: Low-to-moderate 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 potential 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 can enhance the lipophilicity of the molecule, which often correlates with increased membrane permeability.

2. **Acetyl Group**: The acetyl group attached to the thiazole ring introduces a polar character to the molecule. This can affect the molecule's solubility and permeability. The acetyl group can form hydrogen bonds with the artificial membrane, potentially enhancing permeability by facilitating interactions with the membrane's polar head groups.

3. **Phenyl Ring**: The phenyl group is a hydrophobic aromatic ring that can increase the lipophilicity of the molecule. This can enhance the molecule's ability to traverse lipid membranes, contributing to higher permeability.

4. **Furan-2-carboxamide Moiety**: The furan ring is another aromatic heterocycle, which can contribute to the molecule's overall lipophilicity. The carboxamide group introduces additional polar character, which can affect solubility and permeability. The balance between the hydrophobic furan ring and the polar carboxamide group can influence the molecule's ability to interact with the membrane.

Overall, the given molecule contains a combination of hydrophobic and polar elements that suggest it may have moderate to high permeability in the PAMPA assay. The thiazole and phenyl rings contribute to lipophilicity, while the acetyl and carboxamide groups provide polar interactions, potentially facilitating passage through 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:** 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 potential 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.

2. **Carboxamide Group**: The carboxamide group is a polar functional group that can form hydrogen bonds with the membrane or surrounding environment. This can influence the molecule's solubility and permeability, potentially reducing it due to the polar nature of the amide.

3. **N-(2-(2,3-difluorophenyl)ethyl) Substituent**: The presence of fluorine atoms in the phenyl ring can increase the lipophilicity of the molecule, enhancing its ability to permeate lipid membranes. Fluorine atoms can also affect the electronic properties of the molecule, potentially influencing its interaction with the membrane.

4. **2-ethoxy-4-phenylphenyl Methyl Substituent**: This bulky substituent includes an ethoxy group and a phenyl ring, which can increase the hydrophobic character of the molecule. The ethoxy group can also contribute to the molecule's solubility in organic solvents, which may aid in permeation through the membrane.

Overall, the given molecule contains a combination of lipophilic and polar features. The presence of fluorine and aromatic rings suggests a high degree of lipophilicity, which is likely to enhance permeability through the artificial membrane. However, the polar carboxamide group may reduce permeability by increasing interactions with the aqueous environment. The balance of these features suggests that the given molecule likely exhibits high permeability in the PAMPA assay.

Final answer: High permeability

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# 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 complex organic compound that features several functional groups and aromatic rings, which play a crucial role in its permeability characteristics. 

The molecule contains a benzoxazole core, which is a bicyclic structure consisting of a benzene ring fused to an oxazole ring. This core is known for its stability and planarity, which can facilitate interactions with biological membranes. The presence of the oxazole ring can also contribute to the molecule's ability to participate in hydrogen bonding, which may affect its permeability.

Attached to the benzoxazole core is a phenyl ring substituted with three methoxy groups. Methoxy groups are electron-donating and increase the lipophilicity of the molecule. This increased lipophilicity can enhance the molecule's ability to permeate lipid membranes, as it allows the molecule to interact more favorably with the hydrophobic environment of the membrane.

Additionally, the molecule has a phenyl ring with a methylthio substituent. The methylthio group is a sulfur-containing functional group that can increase the molecule's overall hydrophobicity. Sulfur atoms can also participate in specific interactions with biological targets, which may influence the molecule's permeability and binding properties.

Overall, the combination of aromatic rings, methoxy groups, and a methylthio substituent suggests that the given molecule likely has high permeability in the PAMPA assay. The lipophilic nature of the methoxy and methylthio groups, along with the stable benzoxazole core, contribute to its ability to traverse the artificial membrane efficiently.

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 can enhance lipophilicity, which often correlates with increased membrane permeability. The aromatic nature of this core can facilitate interactions with the lipid bilayer of the artificial membrane, potentially enhancing permeability.

2. **Methyl and Oxo Substituents**: The methyl group on the thieno[3,2-b]pyrrole moiety increases the hydrophobic character of the molecule, which can further enhance its ability to permeate lipid membranes. The oxo group (carbonyl) can participate in hydrogen bonding, which might influence the molecule's interaction with the membrane, potentially affecting permeability.

3. **Piperidine Ring**: The piperidine ring is a saturated six-membered nitrogen-containing ring, which is relatively flexible and can enhance the solubility of the molecule. This ring can also contribute to the basicity of the molecule, which might affect its interaction with the acidic components of the artificial membrane.

4. **4-Methylphenyl Group**: The presence of the 4-methylphenyl group introduces additional hydrophobicity and aromaticity. This can enhance the molecule's ability to interact with the hydrophobic regions of the artificial membrane, potentially increasing permeability.

5. **Amide Linkage**: The amide bond connecting the piperidine ring to the rest of the molecule is a polar functional group that can participate in hydrogen bonding. This can influence the molecule's solubility and permeability, potentially affecting its interaction with the membrane.

Overall, the given molecule's combination of aromatic, hydrophobic, and polar features suggests that it may exhibit high permeability in the PAMPA assay, as it can effectively interact with the artificial 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:** 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. **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 pyrrole ring contributes to the overall aromaticity, which can also facilitate passage through lipid membranes.

2. **Ethyl Substituent**: The ethyl group attached to the thieno[3,2-b]pyrrole core 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 increasing permeability.

3. **Carboxamide Group**: The carboxamide functional group is polar and can form hydrogen bonds. This can influence the molecule's solubility and permeability, often providing a balance between hydrophilic and lipophilic properties. In the context of PAMPA, this group may facilitate interactions with the membrane's polar head groups or aqueous environment.

4. **Piperidine Ring**: The piperidine ring is a saturated nitrogen-containing heterocycle that can enhance the molecule's basicity and solubility. It may also contribute to the molecule's ability to interact with the membrane through hydrogen bonding or ionic interactions.

5. **4-Ethylphenyl Group**: The presence of the 4-ethylphenyl group adds to the lipophilicity of the molecule. The phenyl ring can engage in π-π interactions with the aromatic residues in the membrane, while the ethyl group further enhances hydrophobic interactions.

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. These features likely contribute to moderate permeability, allowing the molecule to traverse the membrane while still being subject to some resistance due to its polar and aromatic components.

Final answer: Low-to-moderate permeability.

------
# 372

**SMILES:** CCOC1=C(C=C(C=C1)CCNC(=O)C2=NC3=CC=CC=C3C=C2)OCC

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a quinoline derivative with a carboxamide functional group. The quinoline moiety is a bicyclic aromatic compound consisting of a benzene ring fused to a pyridine ring. This 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 carboxamide group in the molecule suggests potential hydrogen bonding capabilities, which can affect the molecule's solubility and permeability. Carboxamides are polar functional groups that can form hydrogen bonds with water and other polar molecules, which may enhance the molecule's solubility in aqueous environments.

The ethoxy groups attached to the phenyl ring contribute to the molecule's lipophilicity. These groups can increase the hydrophobic character of the molecule, which may facilitate its passage through lipid membranes. However, the balance between hydrophilic and lipophilic properties will determine 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 permeability. The quinoline core provides a degree of rigidity and planarity, which can aid in membrane passage, while the ethoxy groups enhance lipophilicity. However, the carboxamide group may also introduce some hydrophilic character, potentially limiting permeability due to interactions with the aqueous environment.

Therefore, the given molecule is likely to have low-to-moderate permeability in the PAMPA assay.

Final answer: Low-to-moderate 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 due to their ability to traverse lipid bilayers.

The molecule contains a benzimidazole core, which is a bicyclic structure consisting of a benzene ring fused to an imidazole ring. This core is known for its stability and ability to engage in π-π interactions, which can enhance the molecule's ability to permeate through lipid membranes.

Additionally, the molecule has 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 the molecule's lipophilicity, thereby increasing its permeability through lipid membranes.

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.

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 benzimidazole 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. **Benzimidazole Core**: The presence of the benzimidazole moiety contributes to the molecule's ability to interact with biological membranes. Benzimidazole rings are planar and aromatic, which can facilitate interactions with lipid bilayers through π-π stacking and hydrophobic interactions. This can enhance the molecule's permeability across the artificial membrane.

2. **Piperidine Moiety**: The piperidine ring is a saturated nitrogen-containing heterocycle that can increase the molecule's solubility and permeability. The presence of the piperidine group can also enhance the molecule's ability to form hydrogen bonds, which may aid in its interaction with the artificial membrane.

3. **Benzoate Ester Group**: The ester functional group in the benzoate moiety 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 stability of the molecule in the membrane environment.

4. **Overall Lipophilicity**: The combination of aromatic rings and ester groups suggests that the given molecule has a moderate to high lipophilicity. This lipophilicity is likely to facilitate its passage through the artificial membrane, as it can interact with the hydrophobic components of the membrane.

Based on these structural features, the given molecule is likely to exhibit high permeability in the Parallel Artificial Membrane Permeability Assay (PAMPA).

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 an aromatic amide, which suggests that it has a certain degree of rigidity and planarity due to the presence of an aromatic ring. This structural feature can influence its permeability by affecting how the molecule interacts with the artificial membrane.

The molecule contains a pyrrole ring, which is a five-membered aromatic heterocycle. The presence of methyl groups on this pyrrole ring can increase the hydrophobic character of the molecule, potentially enhancing its ability to permeate through the membrane by interacting with hydrophobic regions.

Additionally, the molecule has a sulfonyl group attached to a piperidine ring. The sulfonyl group is a polar functional group, which can increase the molecule's overall polarity. This can lead to increased solubility in aqueous environments, which is beneficial for permeability through biological membranes.

The amide linkage in the molecule is another important feature. Amides are generally polar and can form hydrogen bonds, which can facilitate interactions with the membrane and potentially enhance permeability.

Overall, the combination of aromaticity, hydrophobic methyl groups, polar sulfonyl group, and polar amide linkage suggests that the given molecule may have moderate permeability through the artificial membrane, balancing between hydrophobic and hydrophilic interactions.

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 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. **Indole Core**: The presence of the indole moiety is significant. Indole is a bicyclic structure that is relatively planar and hydrophobic. This core can facilitate interactions with the lipid components of the artificial membrane, enhancing permeability. The indole structure is often associated with good membrane permeability due to its aromatic nature and ability to participate in π-π interactions.

2. **Carboxamide Group**: The carboxamide group is polar and can form hydrogen bonds. While this group can increase solubility in aqueous environments, it can also interact with the polar head groups of the artificial membrane, potentially aiding in permeability. However, it may also introduce some steric hindrance, which could limit permeability.

3. **Pyridine Ring**: The pyridine ring is a heteroaromatic structure that can engage in π-π stacking and hydrogen bonding. The presence of methyl groups on the pyridine ring can increase lipophilicity, which may enhance permeability through the lipid-rich artificial membrane.

4. **Ethoxy and Dimethoxyphenyl Groups**: These groups are ether-linked aromatic rings that increase the lipophilicity of the molecule. The ethoxy and dimethoxy groups can enhance the molecule's ability to traverse the lipid bilayer of the artificial membrane by increasing its hydrophobic character.

5. **Ethyl Linker**: The ethyl chain connecting the pyridine and phenyl groups provides flexibility and spatial separation between the aromatic systems. This flexibility can help the molecule to adapt its conformation to fit into the membrane, potentially enhancing permeability.

Overall, the given molecule's combination of aromatic systems, polar functional groups, and lipophilic substituents suggests 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, making it suitable for further drug development studies.

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 ring structure. This aromatic system 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. This group can increase the molecule's polarity and potentially enhance its ability to form hydrogen bonds with the artificial membrane, which may affect its permeability.

Additionally, the molecule has a benzyl group attached to a nitrogen atom, forming a benzylamino moiety. This group can contribute to the molecule's lipophilicity, which is often associated with increased membrane permeability due to enhanced solubility in lipid environments.

The presence of the isopropyl group attached to the nitrogen atom further increases the molecule's hydrophobic character, which can also promote permeability through lipid membranes.

Overall, the combination of the naphthalene ring, the ketone group, and the benzylamino moiety suggests that the given molecule likely exhibits high permeability in the artificial membrane due to its balanced hydrophobic and hydrophilic properties.

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 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. **Cyclopropyl Group**: The presence of a cyclopropyl group, which is a three-membered carbon ring, can increase the lipophilicity of the molecule. This lipophilic nature can enhance the molecule's ability to traverse lipid membranes, suggesting high permeability.

2. **1,3-Oxazole Ring**: The oxazole ring is a five-membered heterocyclic compound containing both nitrogen and oxygen. This ring can contribute to the molecule's overall stability and rigidity, potentially affecting its ability to interact with the artificial membrane. The presence of heteroatoms can also influence hydrogen bonding and electronic interactions, which may impact permeability.

3. **Ethoxyphenyl Group**: The ethoxy group attached to a phenyl ring can increase the lipophilicity of the molecule, similar to the cyclopropyl group. This can enhance membrane permeability by increasing the molecule's solubility in lipid environments.

4. **Benzene Sulfonamide**: The sulfonamide group is a key functional group that can influence the molecule's solubility and permeability. Sulfonamides are known for their ability to form hydrogen bonds, which can affect the interaction with the artificial membrane. However, the presence of the sulfonamide group can also introduce some degree of polarity, which might reduce permeability compared to purely hydrophobic molecules.

Overall, the given molecule contains several lipophilic groups, such as the cyclopropyl and ethoxyphenyl groups, which suggest high permeability due to increased solubility in lipid environments. However, the presence of the sulfonamide group introduces some polarity, which might moderate the overall permeability. Therefore, the given molecule is likely to 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 fusion of a thiophene ring and a pyrrole ring. The presence of sulfur in the thiophene ring can enhance lipophilicity, which generally increases membrane permeability. The pyrrole ring contributes to the overall aromaticity, which can also facilitate passage through lipid membranes.

2. **Methyl Substitution**: The methyl group attached to the thieno[3,2-b]pyrrole core 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 increasing permeability.

3. **Carboxamide Group**: The carboxamide group is polar and can form hydrogen bonds. While this group can interact with the membrane, it may also introduce some degree of polarity that could limit permeability. However, in the context of PAMPA, the balance of hydrophobic and hydrophilic interactions is crucial, and the presence of this group may not significantly hinder permeability.

4. **Ethoxyphenyl Group**: The ethoxyphenyl moiety introduces additional aromaticity and lipophilicity. The ethoxy group can enhance solubility in organic solvents, which is beneficial for permeability in PAMPA. The phenyl ring can also participate in π-π interactions with the membrane, potentially aiding in permeation.

Overall, the given molecule's structure suggests that it has a balance of hydrophobic and hydrophilic properties, with several aromatic and lipophilic features that likely contribute to high permeability in the PAMPA assay. The combination of the thieno[3,2-b]pyrrole core, methyl substitution, and ethoxyphenyl group all support its ability to traverse the artificial membrane efficiently.

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 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.

The molecule also contains a methoxy group attached to a phenyl ring, which can increase its lipophilicity. This can potentially enhance the molecule's ability to permeate through lipid membranes, contributing to its permeability.

Additionally, the presence of a thiophene ring, a sulfur-containing heterocycle, can also influence the molecule's permeability. Thiophene rings are known for their aromatic stability and can interact with hydrophobic regions of membranes, potentially aiding in permeation.

Overall, the combination of these functional groups suggests that the given molecule may exhibit moderate permeability through the artificial membrane, as the polar sulfonamide group and the lipophilic methoxy and thiophene groups can facilitate interactions with both polar and non-polar regions of the membrane.

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:** 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, which can influence its permeability.

The molecule contains several key structural features that contribute to its permeability:

1. **Sulfonamide Group**: The presence of the sulfonamide group is likely to increase the molecule's polarity, which can enhance its solubility in aqueous environments. This group can also form hydrogen bonds with the artificial membrane, potentially increasing permeability.

2. **Chloro and Methoxy Substituents**: The chloro group on the phenyl ring can increase the molecule's lipophilicity, which may enhance its ability to permeate lipid membranes. The methoxy group, being an electron-donating group, can also influence the electronic properties of the phenyl ring, potentially affecting the molecule's interaction with the membrane.

3. **Thiazolopyrimidine Core**: The thiazolopyrimidine core is a heterocyclic structure that can contribute to the molecule's overall rigidity and planarity. This can affect how the molecule fits into the membrane and its overall permeability.

4. **Methyl Group**: The presence of a methyl group on the phenyl ring can increase the molecule's hydrophobic character, which may enhance its ability to permeate lipid-rich environments like biological membranes.

Overall, the combination of these structural features suggests that the given molecule may have moderate to high permeability in the artificial membrane, as the sulfonamide group enhances solubility and permeability, while the lipophilic and hydrophobic groups may facilitate passage through the membrane.

Final answer: High permeability

------
# 382

**SMILES:** C1=CC=NC(=C1)C2=NC(=CC(=O)N2)CSC3=CC=C(C=C3)Cl

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a pyridine derivative with a complex structure that includes a pyrimidinone core, a pyridine ring, and a chlorophenyl group connected via a thioether linkage. 

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

1. **Lipophilicity**: The presence of the chlorophenyl group contributes to the lipophilic 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.

2. **Polar and Ionic Interactions**: The pyrimidinone and pyridine rings introduce polar characteristics to the molecule. These heterocyclic rings can participate in hydrogen bonding and other polar interactions with the membrane, which may affect the permeability.

3. **Thioether Linkage**: The sulfur atom in the thioether linkage can influence the molecule's overall polarity and flexibility. This linkage may also affect the molecule's ability to traverse the membrane by providing a degree of conformational flexibility.

4. **Overall Molecular Size and Shape**: The combination of aromatic rings and heteroatoms can create a relatively rigid structure, which may impact the molecule's ability to fit through the membrane pores.

Considering these factors, the given molecule is likely to exhibit moderate permeability in the PAMPA assay. The balance between lipophilic and polar characteristics, along with the structural rigidity, suggests that while the molecule can interact with the membrane, it may not easily pass through due to potential steric hindrance.

Final answer: Low-to-moderate permeability.

------
# 383

**SMILES:** CCOC1=C(C=C(C=C1)CCNC(=O)C2=CC=NN2CC3=CC=CC(=C3)C)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. **Aromatic Rings**: The molecule contains two aromatic rings, one being a dimethoxyphenyl group and the other 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, potentially increasing permeability.

2. **Methoxy Groups**: The presence of methoxy groups on the phenyl ring introduces electron-donating properties, which can increase the lipophilicity of the molecule. This can further enhance the molecule's ability to permeate through the lipid-rich environment 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's structure. This flexibility can aid in permeation by allowing the molecule to adopt conformations that optimize interaction with the membrane.

4. **Carboxamide Group**: The carboxamide group is polar and can form hydrogen bonds. While this group can interact with the polar head groups of the artificial membrane, it may also introduce some degree of polarity that could hinder permeability. However, its presence is balanced by the hydrophobic aromatic rings, which dominate the molecule's overall character.

5. **Pyrazole Ring**: The pyrazole ring is a heterocyclic aromatic compound that can contribute to the molecule's overall stability and rigidity. This structural feature can influence the molecule's ability to interact with the membrane, potentially affecting permeability.

Overall, the given molecule's structure suggests that it has a balance of hydrophobic and hydrophilic properties, with the aromatic rings and methoxy groups likely contributing to high permeability through the artificial membrane. The presence of the carboxamide group and the pyrazole ring may provide some additional interactions with the membrane, but the overall lipophilic character is likely to dominate, resulting in high permeability.

Final answer: High 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:** 1

**Correct:** 1

# Response:
The given molecule is a sulfonamide, which is a class of compounds known for their antimicrobial properties. The sulfonamide group in the molecule 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 presence of the 2-fluorophenyl group and the 2-fluorophenyl sulfonyl moiety suggests that the molecule has increased lipophilicity, which can enhance its ability to permeate lipid membranes. Fluorine atoms can also increase the metabolic stability of the molecule, potentially allowing it to remain active for longer periods within a biological system.

The pyrimidine ring in the structure is a heterocyclic aromatic compound, which can contribute to the molecule's ability to interact with various biological targets. The presence of a chloro substituent on the pyrimidine ring can further influence the molecule's electronic properties, potentially affecting its binding affinity and 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 electronic characteristics that favor membrane interaction and permeation.

Final answer: High 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 potential biological activity, often associated with central nervous system effects.

The molecule's permeability in the PAMPA assay can be influenced by several structural features:

1. **Aromatic Rings**: The presence of two benzene rings contributes to the molecule's lipophilicity, which generally enhances membrane permeability. Aromatic rings can interact with the lipid bilayer of the artificial membrane, facilitating passage.

2. **Thiazepine Ring**: The thiazepine ring, containing both sulfur and nitrogen, can introduce some degree of polarity. However, the overall effect is likely minimal compared to the aromatic character of the benzene rings.

3. **N-cyclohexyl Group**: The cyclohexyl group attached to the nitrogen atom adds bulk and hydrophobicity to the molecule. This can further enhance lipophilic interactions with the membrane, promoting permeability.

4. **Carboxamide Group**: The carboxamide group introduces some polarity and potential for hydrogen bonding. While this can affect solubility and permeability, its impact is likely balanced by the overall lipophilic nature of the molecule.

5. **Methyl Group**: The methyl group contributes to the hydrophobic character, which can enhance membrane permeability by increasing lipophilicity.

Overall, the given molecule's structure suggests that it has a high degree of lipophilicity due to its aromatic and hydrophobic groups. This is likely to result in high permeability through the artificial membrane in the PAMPA assay.

Final answer: High permeability

------
# 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 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. **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 quinoline 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. **Acetamide Linkage**: The acetamide group provides additional hydrogen bonding potential, which can influence the molecule's interaction with the membrane. This group can enhance solubility and may facilitate passage through the membrane by interacting with polar sites.

4. **4-Chlorophenyl Methyl Group**: The chlorophenyl group adds to the lipophilicity of the molecule, which can enhance membrane permeability. The presence of the chlorine atom can also influence the electronic properties of the phenyl ring, potentially affecting the molecule's interaction with the membrane.

5. **4-Methylpiperazinylsulfonyl Group**: This group introduces a bulky, polar moiety that can interact with the membrane through hydrogen bonding and van der Waals interactions. The piperazine ring can also contribute to the molecule's overall conformational flexibility, which may aid in permeation.

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 aromatic and lipophilic components enhance membrane interaction, while the polar groups improve solubility and interaction with the membrane's polar regions.

Final answer: Low-to-moderate permeability.

------
# 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 a range of biological activities and pharmacological properties.

To predict the permeability of the given molecule in the PAMPA assay, we need to consider the following structural elements:

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 a polar functional group that can form hydrogen bonds with the artificial membrane. This interaction can influence the molecule's permeability by affecting its solubility and ability to traverse the membrane.

3. **Thiazole Ring**: The thiazole ring is a heterocyclic compound containing both sulfur and nitrogen. This ring can contribute to the molecule's electronic properties and may enhance its ability to interact with the membrane through π-π stacking or other non-covalent interactions.

4. **Dihydrobenzodioxepin Moiety**: The dihydrobenzodioxepin group is a bicyclic structure that can increase the molecule's lipophilicity. This lipophilic character can enhance the molecule's ability to permeate lipid membranes, such as the artificial membrane used in the PAMPA assay.

5. **Phenyl Group**: The phenyl group is a hydrophobic aromatic ring that can also contribute to the molecule's lipophilicity. This can further enhance its permeability by allowing it to interact with the hydrophobic regions of the membrane.

Overall, the combination of these structural features suggests that the given molecule is likely to have 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 a variety of non-covalent interactions, enhancing its ability to permeate the membrane.

Final answer: High permeability

------
# 388

**SMILES:** CCCC1=NC2=C(C=CC(=C2)C(=O)NC3CCCC3)SC4=C1C=C(C=C4)C

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is a dibenzothiazepine, which is a class of compounds known for their tricyclic structure. This structure typically consists of two benzene rings fused to a thiazepine ring, which is a seven-membered ring containing both sulfur and nitrogen atoms. The presence of these rings contributes to the molecule's overall rigidity and planarity, which can influence its permeability.

The molecule also contains a carboxamide group, which is a functional group consisting of a carbonyl group attached to an amine. This group can participate in hydrogen bonding, which may enhance the molecule's solubility and permeability by interacting with the polar sites of the artificial membrane.

Additionally, the molecule has a propyl group and a cyclopentyl group attached to the nitrogen atom of the carboxamide. These alkyl groups can increase the lipophilicity of the molecule, potentially enhancing its ability to permeate through the lipid-rich environment of the artificial membrane.

Overall, the combination of the dibenzothiazepine core, the carboxamide group, and the alkyl substituents suggests that the given molecule may exhibit moderate permeability in the artificial membrane, balancing between hydrophilic and lipophilic interactions.

Final answer: Low-to-moderate permeability.

------
# 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 potential impact on permeability:

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 ethanone group also contributes to 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 heterocyclic 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 overall shape and electronic properties of this core can affect how the molecule fits into the membrane.

4. **Methoxy Group**: The methoxy group attached to the phenyl ring can increase the molecule's polarity, which might enhance its solubility in aqueous environments. However, its presence can also affect the balance between hydrophilicity and lipophilicity, potentially moderating the overall permeability.

5. **Dihydro Component**: The dihydro aspect of the pyrazolo[1,5-a]pyrimidine indicates partial saturation, which can influence the flexibility and conformation of the molecule. This flexibility might affect how the molecule interacts with the membrane.

Overall, the given molecule's structure suggests a balance between lipophilic and polar characteristics. The aromatic and methoxy groups likely enhance lipophilicity, promoting membrane permeability, while the heterocyclic core and methoxy group may provide some degree of polarity. These features collectively suggest that the given molecule would exhibit high permeability in the PAMPA assay.

Final answer: High permeability

------
# 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 and electronic properties. Methoxy groups are electron-donating, which can enhance the molecule's ability to interact with biological membranes by increasing its lipophilicity. This can facilitate the passage of the molecule through lipid bilayers, potentially enhancing its permeability.

The triazolo-thiadiazine core itself is a fused heterocyclic system that can contribute to the molecule's overall stability and ability to interact with biological targets. The presence of nitrogen and sulfur atoms in the heterocyclic rings can also play a role in hydrogen bonding and other non-covalent interactions, which are important for the molecule's binding affinity and specificity.

Overall, the combination of the methoxy-substituted phenyl groups and the triazolo-thiadiazine core suggests that the given molecule may exhibit high permeability in the PAMPA assay due to its enhanced lipophilicity and potential for favorable interactions with the artificial membrane.

Final answer: High permeability.

------
# 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 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 multiple aromatic rings, including a thienopyrimidine core and a 4-methylphenyl group. Aromatic rings generally contribute to lipophilicity, which can enhance membrane permeability due to their ability to interact with lipid bilayers.

2. **Sulfanyl Group**: The presence of a sulfanyl (thioether) linkage, connecting the thienopyrimidine core to the tetrazole ring, can influence the molecule's polarity and solubility. Sulfanyl groups can enhance lipophilicity, which may improve membrane permeability.

3. **Tetrazole Ring**: The tetrazole moiety is a polar functional group that can participate in hydrogen bonding and ionic interactions. This can affect the molecule's solubility and permeability, potentially increasing it due to the ability to form interactions with the membrane.

4. **Overall Lipophilicity**: The combination of aromatic rings and the sulfanyl linkage suggests that the given molecule is likely to be lipophilic. This lipophilicity is generally associated with higher permeability in PAMPA assays, as it facilitates passage through the lipid-rich artificial membrane.

Based on these structural characteristics, the given molecule is likely to exhibit high permeability in the PAMPA assay due to its lipophilic nature and the presence of functional groups that can interact with the membrane.

Final answer: High permeability

------
# 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:** 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 to understand its permeability:

1. **Biphenyl Structure**: The presence of a biphenyl moiety, which consists of two phenyl rings connected by a single bond, 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.

2. **Piperidine Ring**: The piperidine ring is a six-membered nitrogen-containing heterocycle. This ring can introduce some degree of polarity to the molecule, which may facilitate interactions with the polar head groups of the artificial membrane. The presence of the piperidine ring can also affect the overall conformation of the molecule, potentially influencing its ability to permeate the membrane.

3. **Carboxylate Ester Group**: The ethyl ester group is a polar functional group that can participate in hydrogen bonding and dipole-dipole interactions with the artificial membrane. This group can enhance the solubility of the molecule in the membrane environment, which may improve its permeability.

4. **Amide Linkage**: The amide linkage in the molecule is a polar functional group that can form hydrogen bonds with the artificial membrane. This can contribute to the molecule's ability to permeate the membrane by stabilizing interactions with the membrane's polar regions.

5. **Overall Molecular Size and Complexity**: The given molecule is relatively large and complex, which can affect its permeability. Larger molecules may have reduced permeability due to steric hindrance and difficulty in navigating the membrane's structure.

Considering these structural features, the given molecule is likely to exhibit moderate permeability in the PAMPA assay. The hydrophobic biphenyl moiety and polar functional groups, such as the ester and amide linkages, suggest a balance between hydrophobic and hydrophilic interactions with the artificial membrane. This balance can facilitate moderate permeability, allowing the molecule to traverse the membrane while maintaining sufficient interaction with the membrane components.

Final answer: Low-to-moderate permeability.

------
# 393

**SMILES:** CC1=C(N(C(=C1C(=O)C)C)C)C(=O)NC2=CC(=CC=C2)[S+](=O)(N3CCCCCC3)[O-]

**Label:** 1

**Predi:** 0

**Correct:** 0

# Response:
The given molecule is an aromatic amide, which suggests that it has a structure that includes an amide group attached to an aromatic ring. This structural feature is often associated with certain physicochemical properties, such as the ability to participate in hydrogen bonding and interact with biological membranes.

The molecule contains a pyrrole ring, which is a five-membered aromatic heterocycle. The presence of methyl groups on the pyrrole ring can increase the hydrophobic character of the molecule, potentially enhancing its ability to permeate lipid membranes.

Additionally, the molecule has an acetyl group attached to the pyrrole ring, which can influence its polarity and solubility. The acetyl group is a small, polar moiety that can participate in hydrogen bonding, which may affect the molecule's interaction with the artificial membrane.

The phenyl group attached to the sulfonyl moiety contributes to the overall hydrophobicity of the molecule, which can enhance its ability to permeate through lipid-rich environments, such as biological membranes.

The sulfonyl group itself is a polar functional group that can increase the molecule's solubility in polar solvents. This group can also participate in hydrogen bonding, which may affect the molecule's interaction with the artificial membrane.

Overall, the combination of aromatic rings, hydrophobic methyl groups, and polar functional groups suggests that the given molecule may have moderate permeability to the artificial membrane, balancing between hydrophobic and hydrophilic interactions.

Final answer: Low-to-moderate permeability.

------
# 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:** 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.

In the given molecule, the sulfonamide group is linked to a phenyl ring, which can contribute to the molecule's overall lipophilicity. The presence of the sulfonamide group suggests that the molecule may have moderate permeability through the artificial membrane, as sulfonamides are generally able to traverse biological membranes due to their balance of hydrophilic and lipophilic properties.

Additionally, the molecule contains a methoxy group attached to a phenyl ring, which can increase its lipophilicity and potentially enhance its ability to permeate the membrane. The ethoxyphenyl moiety also contributes to the lipophilic character of the molecule, which may further facilitate its permeability.

Overall, the combination of these functional groups suggests that the given molecule would exhibit moderate to high permeability in the PAMPA assay, as it possesses both polar and non-polar characteristics that allow it to interact with the artificial membrane effectively.

Final answer: High permeability

------
# 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.

2. **Carboxylate Ester Group**: The ester group in the molecule, specifically the ethyl ester, can influence its solubility and permeability. Esters are generally more lipophilic than their corresponding acids, which can facilitate passive diffusion through lipid membranes. However, esters can also be hydrolyzed by esterases in biological systems, which might affect the molecule's stability and permeability.

3. **Propyl Side Chain**: The propyl group is a simple alkyl chain that increases the hydrophobic character of the molecule. This can enhance membrane permeability by increasing the molecule's ability to interact with the lipid components of the membrane.

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 group introduces a polar and potentially ionizable feature, which can influence the molecule's solubility and permeability. The presence of this group might also affect the molecule's ability to form hydrogen bonds with the membrane or other molecules.

Overall, the given molecule's structure suggests that it has a balance of hydrophobic and hydrophilic features, which can contribute to moderate permeability in the PAMPA assay. The aromatic benzofuran core and the ester group likely enhance lipophilicity, while the methoxyphenylsulfonylamino group introduces some polar character. These features collectively suggest that the molecule may exhibit moderate permeability, neither being highly permeable nor low-to-moderate permeable.

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 imidazolidine-2,4-dione class, which is known for its potential biological activity, often related to its ability to interact with various biological targets. The molecule's structure includes several key features that influence its permeability:

1. **Imidazolidine-2,4-dione Core**: This core is a cyclic urea derivative, which is often associated with good permeability due to its ability to form hydrogen bonds and interact with biological membranes. The presence of two carbonyl groups in the imidazolidine ring can enhance the molecule's ability to engage in hydrogen bonding, potentially increasing its permeability.

2. **Substituted Phenyl Groups**: The molecule contains a 4-fluorophenyl group and a 4-ethoxyphenyl group. The fluorine atom in the 4-fluorophenyl group can increase the lipophilicity of the molecule, which may enhance its ability to permeate lipid membranes. The ethoxy group in the 4-ethoxyphenyl moiety can also contribute to lipophilicity, further aiding in membrane permeability.

3. **Thiophene Ring**: The presence of a thiophene ring, which is a sulfur-containing heterocycle, can increase the molecule's overall lipophilicity. Thiophene rings are known to enhance the ability of molecules to penetrate lipid bilayers, which can contribute to high permeability.

4. **Amide Linkage**: The acetamide linkage in the molecule can participate in hydrogen bonding, which may facilitate interaction with the artificial membrane. This can also contribute to the molecule's overall stability and permeability.

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 hydrophilic and lipophilic properties that favor interaction with the artificial membrane.

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:** 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. This structural feature is significant in determining the molecule's permeability.

The piperidine ring is a six-membered ring containing one nitrogen atom, which contributes to the molecule's basicity and can enhance its ability to interact with biological membranes. The presence of the carboxamide group, which includes a carbonyl group (C=O) and an amine (NH2), can form hydrogen bonds, potentially increasing the molecule's solubility and interaction with the membrane.

Additionally, the molecule contains a thiazole ring, which is a five-membered ring with both sulfur and nitrogen atoms. This heterocyclic structure can contribute to the molecule's overall stability and ability to penetrate biological membranes.

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

Overall, the combination of these structural features suggests that the given molecule may have moderate permeability to the artificial membrane, as the balance of hydrophilic and lipophilic properties allows it to interact with both aqueous and lipid environments.

Final answer: Low-to-moderate 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 to understand its permeability characteristics.

1. **Indole Core**: The molecule contains an indole structure, which is a bicyclic compound 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, which can facilitate passage through lipid bilayers. This core structure is likely to contribute to the molecule's permeability.

2. **Pyrrolidinone Moiety**: The presence of a pyrrolidinone group, which is a five-membered lactam, can enhance the molecule's solubility and permeability. The lactam ring can participate in hydrogen bonding, which may aid in the molecule's interaction with the artificial membrane.

3. **Carboxamide Group**: The carboxamide functional group is known for its ability to form hydrogen bonds, which can influence the molecule's solubility and permeability. This group can interact with the polar components of the artificial membrane, potentially enhancing permeability.

4. **Dimethylphenyl Substituent**: The dimethylphenyl group is a hydrophobic aromatic ring that can increase the lipophilicity of the molecule. This hydrophobic character can enhance the molecule's ability to traverse lipid-rich environments, such as biological membranes.

5. **Methyl Substituents**: The presence of methyl groups on the indole and pyrrolidinone rings can increase the molecule's hydrophobicity, which may further enhance its permeability through the artificial membrane.

Overall, the given molecule's combination of aromatic, hydrophobic, 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.

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 calcium channel blocker. 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 a dihydropyridine core, which is a common feature in calcium channel blockers. This core is known for its ability to interact with the lipid bilayer of cell membranes, facilitating the molecule's passage through the membrane. The presence of the dihydropyridine ring contributes to the molecule's overall lipophilicity, which is a key factor in its permeability.

Additionally, the molecule has a nitrophenyl group attached to the dihydropyridine ring. The nitro group is an electron-withdrawing group, which can influence the electronic distribution of the molecule, potentially affecting its interaction with the artificial membrane.

The molecule also contains a benzylpiperidine moiety, which is a bulky hydrophobic group. This moiety can enhance the molecule's lipophilicity, further promoting its permeability through the membrane.

The presence of ester groups in the molecule can also play a role in its permeability. Esters are generally more lipophilic than their corresponding acids, which can facilitate the molecule's passage through the lipid-rich environment of the artificial membrane.

Overall, the combination of the dihydropyridine core, nitrophenyl group, benzylpiperidine moiety, and ester functionalities contribute to the molecule's high permeability in the PAMPA assay.

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 potential impact on permeability:

1. **Benzimidazole Core**: The presence of a benzimidazole moiety is significant. Benzimidazole is a bicyclic structure that is relatively planar and can engage in π-π stacking interactions. This can enhance the molecule's ability to interact with the artificial membrane, potentially increasing its permeability.

2. **Fluorophenyl Group**: The fluorophenyl group is a phenyl ring substituted with a fluorine atom. The fluorine atom is highly electronegative, which can influence the electronic distribution of the molecule. This can affect the molecule's lipophilicity and its ability to traverse the membrane. Fluorine can also enhance the metabolic stability of the molecule, which might indirectly affect permeability by prolonging the molecule's presence in the assay.

3. **Trifluoromethylpiperidine Moiety**: The trifluoromethyl group is known for increasing lipophilicity, which can enhance the molecule's ability to permeate lipid membranes. The piperidine ring is a saturated heterocycle that can provide structural rigidity and influence the overall conformation of the molecule, potentially affecting its interaction with the membrane.

4. **Methanone Linkage**: The methanone group (a carbonyl group) can participate in hydrogen bonding and dipole-dipole interactions. This functional group can influence the molecule's solubility and permeability by affecting its interaction with the membrane and the surrounding environment.

Overall, the given molecule contains several features that suggest it may have high permeability in the PAMPA assay. The combination of aromatic systems, fluorine substituents, and a carbonyl group likely contribute to a balance of lipophilicity and electronic properties that favor membrane permeation.

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 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. **Isoquinoline Moiety**: The presence of the isoquinoline structure contributes to the molecule's aromaticity and planarity. Aromatic and planar structures can enhance the molecule's ability to interact with the artificial membrane, potentially increasing permeability. However, the specific substituents on this moiety can also affect its overall permeability.

2. **Fluorophenyl Group**: The fluorophenyl group introduces a fluorine atom, which can increase the lipophilicity of the molecule. Fluorine's high electronegativity can also influence the electronic distribution across the molecule, potentially affecting its interaction with the membrane.

3. **Oxazole Ring**: The oxazole 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 pores, potentially influencing 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 interaction with the membrane, potentially increasing permeability.

5. **Dimethylpropanoyl Group**: This group is a bulky, hydrophobic moiety that can increase the molecule's lipophilicity. Increased lipophilicity often correlates with higher membrane permeability, as the molecule can more easily traverse lipid bilayers.

6. **Fluoro Substitution**: The presence of a fluorine atom in the phenyl ring can enhance the molecule's lipophilicity and membrane permeability due to its ability to form favorable interactions with the lipid components of the membrane.

Overall, the given molecule's combination of aromatic, heterocyclic, and lipophilic features suggests that it may have high permeability in the PAMPA assay. The balance of polar and non-polar groups, along with the presence of fluorine, likely facilitates its interaction with the artificial membrane, enhancing its permeability.

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:** 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 potential impact on permeability:

1. **Pyrazolopyrimidine Core**: The presence of a pyrazolopyrimidine core is significant. 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. Such interactions can facilitate the passage of the molecule through the membrane.

2. **Imino and Sulfanyl Groups**: The imino group (a nitrogen-containing functional group) and the sulfanyl group (a sulfur-containing functional group) can contribute to the molecule's polarity and hydrogen bonding capabilities. These groups may enhance the molecule's solubility in the aqueous environment of the PAMPA assay, potentially increasing its permeability.

3. **Aromatic Substituents**: The given molecule contains two aromatic rings: a 4-methylphenyl group and a 2-methylphenyl group. These hydrophobic aromatic rings can enhance the molecule's lipophilicity, which is often associated with increased membrane permeability. However, the balance between hydrophilic and lipophilic properties is crucial, and the overall effect will depend on the specific balance of these groups.

4. **Thioether Linkage**: The sulfanyl group connects the pyrazolopyrimidine core to the acetamide moiety. Thioether linkages can contribute to the molecule's flexibility and overall conformation, which may affect how the molecule fits into the membrane.

5. **Acetamide Moiety**: The acetamide group introduces additional hydrogen bonding potential, which can influence the molecule's solubility and interaction with the membrane. This group may also affect the overall polarity of the molecule.

In summary, the given molecule's structural features suggest a balance of hydrophilic and lipophilic properties, with aromatic and heterocyclic components that could facilitate membrane interaction. These characteristics are likely to result in a moderate to high permeability in the PAMPA assay, allowing the molecule to effectively traverse the artificial membrane.

Final answer: High 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 pyridopyrimidine derivative, which is a class of compounds known for their potential biological activity. The structure of the given molecule includes a pyridopyrimidine core, which is a bicyclic system combining pyridine and pyrimidine rings. This core is known for its ability to interact with various biological targets, often contributing to the molecule's pharmacological properties.

The molecule also features a 3-fluorophenyl group attached to a nitrogen atom. The presence of the fluorine atom can enhance the molecule's lipophilicity, potentially improving its ability to permeate lipid membranes. Fluorine is a small, highly electronegative atom that can also influence the electronic distribution within the molecule, which may affect its interaction with biological membranes.

Additionally, the molecule contains a phenylmethyl group attached to another nitrogen atom. This group can contribute to the overall hydrophobic character of the molecule, which is often beneficial for membrane permeability as it can facilitate passage through lipid bilayers.

The piperazine ring in the structure is a common motif in medicinal chemistry, often used to enhance the solubility and bioavailability of compounds. Piperazine can also provide flexibility to the molecule, allowing it to adopt conformations that may be favorable for permeation through the artificial membrane.

Overall, the combination of the pyridopyrimidine core, the fluorophenyl group, and the piperazine ring suggests that the given molecule may exhibit high permeability in the PAMPA assay, as these structural features are generally associated with favorable membrane permeability characteristics.

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 includes several functional groups and structural features that influence its permeability in the PAMPA assay. Let's break down these features:

1. **Furan Rings**: The molecule contains two furan rings, which are five-membered aromatic heterocycles with oxygen. Furan rings are relatively polar and can engage in π-π interactions and hydrogen bonding. This can enhance the molecule's solubility in polar environments, such as the PAMPA assay, and potentially increase its permeability.

2. **Ester Linkage**: The ester functional group in the molecule is formed between the oxoethyl group and the furan-2-ylmethyl group. Esters are generally polar and can participate in hydrogen bonding, which may facilitate the molecule's interaction with the PAMPA membrane. However, esters can also be susceptible to hydrolysis, which might affect the stability of the molecule in the assay.

3. **Thiophene Ring**: The thiophene ring is another five-membered aromatic heterocycle, but with sulfur instead of oxygen. Thiophene is less polar than furan, but it is still aromatic and can contribute to the molecule's overall lipophilicity. The presence of the thiophene ring may enhance the molecule's ability to permeate the membrane by increasing its hydrophobic character.

4. **Amino Group**: The amino group attached to the oxoethyl moiety is a basic functional group that can participate in hydrogen bonding and ionic interactions. This can increase the molecule's solubility in water and potentially enhance its permeability through the PAMPA membrane.

Overall, the given molecule has a combination of polar and non-polar characteristics due to its aromatic rings and functional groups. The presence of furan and thiophene rings suggests that the molecule may have moderate to high permeability in the PAMPA assay, as these rings can facilitate interactions with the membrane while also providing some hydrophobic character. However, the ester linkage may be a point of vulnerability to hydrolysis, which could affect the molecule's stability during the 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 play a significant role in its permeability characteristics. 

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 and aromatic nature, which can facilitate interactions with the artificial membrane, potentially enhancing permeability due to favorable stacking interactions and electronic properties.

Additionally, the molecule has a pyridine ring attached to the imidazo[1,2-a]pyridine core. Pyridine rings are known for their basicity and ability to participate in hydrogen bonding, which can influence the molecule's solubility and permeability. The presence of this pyridine ring may contribute to the molecule's ability to interact with the membrane through hydrogen bonding or dipole interactions.

The molecule also features an aniline group, which is an aromatic amine. Aniline groups can enhance permeability due to their ability to form hydrogen bonds and their relatively planar structure, which can facilitate passage through the membrane.

Furthermore, the presence of a methyl group on the imidazo[1,2-a]pyridine core and a propan-2-yl group on the aniline moiety can increase the lipophilicity of the molecule. Increased lipophilicity often correlates with higher membrane permeability, as it can enhance the molecule's ability to dissolve in the lipid bilayer of the membrane.

Overall, the combination of aromatic rings, basic nitrogen atoms, and lipophilic substituents in the given molecule suggests that it may exhibit high permeability in the Parallel Artificial Membrane Permeability Assay (PAMPA).

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 derivative of isoquinoline, which is a bicyclic compound consisting of a benzene ring fused to a pyridine ring. The presence of the dioxolo group, which is a methylenedioxy bridge, suggests that the molecule has additional oxygen atoms incorporated into its structure. This modification can influence the molecule's electronic properties and potentially its ability to interact with biological membranes.

The dihydro component indicates that the molecule has reduced aromaticity compared to fully aromatic isoquinoline, which can affect its chemical reactivity and solubility. The methyl group attached to the nitrogen atom in the isoquinoline structure can increase the molecule's lipophilicity, potentially enhancing its ability to permeate lipid membranes.

In the context of the PAMPA assay, the artificial membrane mimics biological membranes, and the molecule's permeability is determined by its ability to cross this model membrane. The presence of polar functional groups, such as the dioxolo moiety, can facilitate interactions with the membrane, potentially increasing permeability. However, the overall lipophilicity of the molecule, influenced by the methyl group and the aromatic system, may also play a significant role in its permeability.

Considering these structural features, the given molecule is likely to exhibit moderate permeability in the PAMPA assay, balancing its polar and non-polar characteristics.

Final answer: Low-to-moderate permeability.

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