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Exam 1 - Lecture 5 - 9, Organic functional groups and drug metabolism

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Total cards: 24•Content version: v4•Public deck•Updated: 8/1/2026

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#1
Front (Question)

Lipinski’s Rule of Five

Back (Answer)

orally active drug has no more than 1 violation of the following criteria Not more than 5 HBD Not more than 10 HBA Molecular weight under 500 g/mol Partition coefficient log P less than 5, 3-4 is optimal

#2
Front (Question)

rank Intramolecular forces between drug and binding site

Back (Answer)

Covalent (strongest, 200 - 400kJ) irreversible Electrostatic or Ionic ( 20 - 40 kJ) Hydrogen bonds ( 16 - 30 kJ) Van Der Waals (2 - 4 kJ)

#3
Front (Question)

Characteristics of Electrostatic or ionic bond

Back (Answer)

Takes place between 2 opposite charge groups Strong interactions in Hydrophilic environment Strength inversely proportional to distance, drops off less rapidly than other forms Most important initial interaction as drug enters binding site

#4
Front (Question)

Characteristics of Hydrogen Bonds

Back (Answer)

Between deficient hydrogen and electron rich heteroatom (N or O) optimum orientation where angle between X,H and Y is 180

#5
Front (Question)

H-Bond donor

Back (Answer)

Group with electron deficient hydrogen

#6
Front (Question)

H-Bond acceptor

Back (Answer)

Group with electron rich heteroatom

#7
Front (Question)

Strong hydrogen bond acceptors

Back (Answer)

carboxylate ion, phosphate ion, tertiary amine

#8
Front (Question)

Moderate hydrogen bond acceptors

Back (Answer)

Carboxylic acid, amide oxygen, ketone, ester, ether, alcohol

#9
Front (Question)

Poor hydrogen bond acceptors

Back (Answer)

Sulfur, fluorine, chlorine, aromatic ring, amide nitrogen,, aromatic amine

#10
Front (Question)

Good Hydrogen bond donor

Back (Answer)

Quaternary ammonium ion

#11
Front (Question)

Characteristics of Van Der Waals interaction

Back (Answer)

occur between hydrophobic region of drug and target interactions drop off rapidly with distance, crucial contribution to binding

#12
Front (Question)

Functional groups that exhibit Van Der Waals

Back (Answer)

Alkanes Aromatic Hydrocarbons Halogenated Hydrocarbons

#13
Front (Question)

Characteristics of Dipole-dipole interaction

Back (Answer)

occur if drug and binding site have dipole moments orientation is beneficial if other binding groups are position correctly orientation is detrimental if other binding groups are not positioned correctly strength decreases more quickly than electrostatic but less quickly than VdW with distance

#14
Front (Question)

Io-dipole vs Dipole-dipole

Back (Answer)

Ion-dipole stronger

#15
Front (Question)

Functional groups that form dipole-dipole

Back (Answer)

Ether and amines

#16
Front (Question)

Functional groups that form ion-dipole

Back (Answer)

Alcohols, sulfuric acids, quaternary ammonium, phenol

#17
Front (Question)

Bronsted-Lowery Acid

Back (Answer)

substance capable of giving a proton, acid turned into conjugate base

#18
Front (Question)

Bronsted-Lowery Base

Back (Answer)

substance capable of accepting proton, base turned into conjugate acid

#19
Front (Question)

Bronsted-Lowery neutral

Back (Answer)

functional groups that cannot give up or accept a proton

#20
Front (Question)

Hydrophobic and lipophilic

Back (Answer)

Water hating and lipid loving

#21
Front (Question)

Hydrophilic and lipophobic

Back (Answer)

Water loving and lipid hating

#22
Front (Question)

Lipophilic functional groups

Back (Answer)

Aromatic hydrocarbons, Halogenated Hydrocarbons, Thioethers, Alkanes, Alkenes

#23
Front (Question)

Hydrophilic functional groups

Back (Answer)

Alcohols, carboxylic acids, amines

#24
Front (Question)

Characteristics of alkane functional groups

Back (Answer)

They are lipophilic Can only do Van Der Waals Immisicble in water, but will dissolve in lipid solvent or oil layer Inert to conditions “on the shelf”, bc hard to oxidize C-H bond under atmospheric conditions