Dr. Ann Perkins is studying a series of 4 compounds. Which compound has chemical properties LEAST like those of orally available drugs, per the criteria discussed in class?

Compound ID Hydrogen-bond donors Hydrogen-bond acceptors Molecular mass LogP
Mol1 2 7 124.6 4.7
Mol2 1 3 312.2 2.5
Mol3 6 8 239.6 5.6
Mol4 3 2 329.2 1.6

Question

Dr. Ann Perkins is studying a series of 4 compounds. Which compound has chemical properties LEAST like those of orally available drugs, per the criteria discussed in class?

Compound ID     Hydrogen-bond donors     Hydrogen-bond acceptors     Molecular mass     LogP  
Mol1            2                        7                            124.6              4.7  
Mol2            1                        3                            312.2              2.5  
Mol3            6                        8                            239.6              5.6  
Mol4            3                        2                            329.2              1.6

BlackTom AI · Accepted Answer

To determine which compound is least like typical orally available drugs, we should compare each molecule against common drug-likeness criteria such as Lipinski's rules: H-bond donors (HBD) ≤ 5, H-bond acceptors (HBA) ≤ 10, molecular weight (MW) ≤ ~500 Da, and logP ≤ ~5. These properties generally favor oral bioavailability.

Mol4: HBD = 3, HBA = 2, MW = 329.2, LogP = 1.6. All of these values fall well within the conventional ranges for oral drugs (moderate HBD/HBA counts, MW under 500, and fairly lipophilic but not excessive logP). This compound aligns with typical oral-drug chemical space.

Mol2: HBD = 1, HBA = 3, MW = 312.2, LogP = 2.5. Also comfortably within Lipinski-like limits: low HBD/HBA, moderate MW, and low to moderate lipophilicity. This profile is characteristic of orally available drugs.

Mol1: HBD = 2, HBA = 7, MW = 124.6, LogP = 4.7. Here, HBD and HBA are reasonable, MW is small, and LogP is around 4.7, which is typical for many oral drugs. Overall, it fits the expected drug-like range, though the relatively high HBA is still acceptable within the usual limits.

Mol3: HBD = 6, HBA = 8, MW = 239.6, LogP = 5.6. This combination stands out for two reasons. First, HBD = 6 exceeds the common cutoff of 5, suggesting a tendency toward poor membrane permeability and solubility balance. Second, LogP = 5.6 is above the usual threshold (~5), indicating higher lipophilicity which can challenge oral bioavailability due to solubility issues. The simultaneous exceedance of HBD and LogP makes Mol3 notably less drug-like in the oral context compared with the others.

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