GMS6504 LECTURE 2 EXAM QUESTIONS AND ANSWERS
WITH COMPLETE SOLUTIONS VERIFIED
What is Lipinski's Rule of 5 regarding molecular mass?
Poor absorption or permeation are more likely when molecular mass is greater than 500
Da.
What does Lipinski's Rule of 5 say about lipophilicity?
Poor absorption or permeation are more likely when LogP is greater than 5.
According to Lipinski's Rule of 5, how many hydrogen bond donors can a
compound have?
More than 5 hydrogen bond donors (OH, FH, NH) increases the likelihood of poor
absorption.
According to Lipinski's Rule of 5, how many hydrogen bond acceptors can a
compound have?
More than 10 hydrogen bond acceptors increases the likelihood of poor absorption.
What is the definition of the partition coefficient?
The ratio of the equilibrium concentrations of a dissolved substance in a two-phase
system containing two large immiscible solvents (Water and n-octanol).
What is the range for the partition coefficient log P in improved Lipinski
parameters?
The range is -0.4 to +5.6.
,What is the acceptable range for molar refractivity in improved Lipinski
parameters?
Molar refractivity should be from 40 to 130.
What is the acceptable molecular weight range in improved Lipinski parameters?
Molecular weight should be from 160 to 500.
What is the acceptable number of atoms in improved Lipinski parameters?
The number of atoms should be from 20 to 70.
What is the maximum polar surface area in improved Lipinski parameters?
The polar surface area should be no greater than 140 Ų.
What is a potential negative aspect of chemical reactivity in drug design?
Modification of proteins and/or nucleic acids can be bad if unanticipated and non-
selective.
What is a potential positive aspect of chemical reactivity in drug design?
Chemical reactivity can be good if it is selective.
What does it mean for a compound to be labile in biological systems?
It is prone to breaking down in the body to make a prodrug that can give an active drug.
What are some examples of chemically reactive functional groups?
Examples include epoxides and Michael acceptors.
Why are epoxides considered dangerous?
Epoxides are very reactive and are considered carcinogens.
What is a Michael acceptor?
A Michael acceptor is a carbonyl conjugated with a double bond and is very reactive.
Lipinski's Rule of 5: Poor absorption or permeation are more likely when:
, 1. Molecular mass greater than 500 Da
2. High lipophilicity (expressed as LogP greater than 5)
3. More than 5 hydrogen bond donors (OH,FH, NH)
4. More than 10 hydrogen bond acceptors
What is a potential negative effect of modifying proteins or nucleic acids?
It can be bad if unanticipated and non-selective.
What is a potential positive effect of modifying proteins or nucleic acids?
It can be good if selective.
What does it mean for a compound to be labile in biological systems?
It is prone to breaking down in the body to make a prodrug, then fall apart to give an
active drug.
What are some examples of chemically reactive functional groups?
Esters, amide bonds, disulfide bonds.
What is a disadvantage of compounds that may be degraded in vivo?
They may lose their effectiveness as drugs.
How can chemical reactivity be beneficial in drug design?
It can be incorporated into the design of pro-drugs.
What is an epoxide?
A carcinogen that is very reactive.
What is a Michael acceptor?
A carbonyl conjugated with a double bond that is very reactive.
What is the prodrug idea?
WITH COMPLETE SOLUTIONS VERIFIED
What is Lipinski's Rule of 5 regarding molecular mass?
Poor absorption or permeation are more likely when molecular mass is greater than 500
Da.
What does Lipinski's Rule of 5 say about lipophilicity?
Poor absorption or permeation are more likely when LogP is greater than 5.
According to Lipinski's Rule of 5, how many hydrogen bond donors can a
compound have?
More than 5 hydrogen bond donors (OH, FH, NH) increases the likelihood of poor
absorption.
According to Lipinski's Rule of 5, how many hydrogen bond acceptors can a
compound have?
More than 10 hydrogen bond acceptors increases the likelihood of poor absorption.
What is the definition of the partition coefficient?
The ratio of the equilibrium concentrations of a dissolved substance in a two-phase
system containing two large immiscible solvents (Water and n-octanol).
What is the range for the partition coefficient log P in improved Lipinski
parameters?
The range is -0.4 to +5.6.
,What is the acceptable range for molar refractivity in improved Lipinski
parameters?
Molar refractivity should be from 40 to 130.
What is the acceptable molecular weight range in improved Lipinski parameters?
Molecular weight should be from 160 to 500.
What is the acceptable number of atoms in improved Lipinski parameters?
The number of atoms should be from 20 to 70.
What is the maximum polar surface area in improved Lipinski parameters?
The polar surface area should be no greater than 140 Ų.
What is a potential negative aspect of chemical reactivity in drug design?
Modification of proteins and/or nucleic acids can be bad if unanticipated and non-
selective.
What is a potential positive aspect of chemical reactivity in drug design?
Chemical reactivity can be good if it is selective.
What does it mean for a compound to be labile in biological systems?
It is prone to breaking down in the body to make a prodrug that can give an active drug.
What are some examples of chemically reactive functional groups?
Examples include epoxides and Michael acceptors.
Why are epoxides considered dangerous?
Epoxides are very reactive and are considered carcinogens.
What is a Michael acceptor?
A Michael acceptor is a carbonyl conjugated with a double bond and is very reactive.
Lipinski's Rule of 5: Poor absorption or permeation are more likely when:
, 1. Molecular mass greater than 500 Da
2. High lipophilicity (expressed as LogP greater than 5)
3. More than 5 hydrogen bond donors (OH,FH, NH)
4. More than 10 hydrogen bond acceptors
What is a potential negative effect of modifying proteins or nucleic acids?
It can be bad if unanticipated and non-selective.
What is a potential positive effect of modifying proteins or nucleic acids?
It can be good if selective.
What does it mean for a compound to be labile in biological systems?
It is prone to breaking down in the body to make a prodrug, then fall apart to give an
active drug.
What are some examples of chemically reactive functional groups?
Esters, amide bonds, disulfide bonds.
What is a disadvantage of compounds that may be degraded in vivo?
They may lose their effectiveness as drugs.
How can chemical reactivity be beneficial in drug design?
It can be incorporated into the design of pro-drugs.
What is an epoxide?
A carcinogen that is very reactive.
What is a Michael acceptor?
A carbonyl conjugated with a double bond that is very reactive.
What is the prodrug idea?
