Drug-likeness

Check a structure against the Lipinski, Veber, Ghose, Egan and lead-likeness rules, with QED, a bioavailability radar and every descriptor behind the verdict.

Compound

Structure

ImatinibC₂₉H₃₁N₇O · 493.62 g/mol

raises logPlowers logP

Rule sets

Passes 3 of 5

Lipinski rule of fivePasses

All 4 criteria met.

Lipinski et al., Adv. Drug Deliv. Rev. 1997, 23, 3
VeberPasses

All 2 criteria met.

Veber et al., J. Med. Chem. 2002, 45, 2615
GhoseFails
- Molar refractivity 146.89 cm³/mol, above 130
- Molar mass 493.62 g/mol, above 480
Ghose et al., J. Comb. Chem. 1999, 1, 55
EganPasses

All 2 criteria met.

Egan et al., J. Med. Chem. 2000, 43, 3867
Lead-likenessFails
- Molar mass 493.62 g/mol, above 350
- logP 4.59, above 3.5
Teague et al., Angew. Chem. Int. Ed. 1999, 38, 3743
QED0.39

Quantitative estimate of drug-likeness from 0 to 1: the weighted geometric mean of eight property desirabilities.

Bickerton et al., Nat. Chem. 2012, 4, 90

Bioavailability radar

Shaded: the range suited to oral bioavailability. Red points fall outside it.

Axis	Value	Optimal
LipophilicitylogP	4.59	−0.7 to 5
SizeMolar mass	493.62 g/mol	150 to 500
PolarityTPSA	86.28 Å²	20 to 130
InsolubilitylogS (ESOL)	−5.81	−6 to 0
UnsaturationFraction Csp³	0.24	0.25 to 1
FlexibilityRotatable bonds	7	0 to 9

Descriptors

Property	Value	Limits
Molar mass	493.62 g/mol	Lipinski ≤ 500Ghose 160 to 480Lead-like 250 to 350
logPWildman–Crippen	4.59	Lipinski ≤ 5Ghose −0.4 to 5.6Egan ≤ 5.88Lead-like ≤ 3.5
TPSAtopological polar surface area, N and O	86.28 Å²	Veber ≤ 140Egan ≤ 131.6
NH and OHLipinski's donor count	2	Lipinski ≤ 5
N and OLipinski's acceptor count	8	Lipinski ≤ 10
H-bond donors	2	—
H-bond acceptors	7	—
Rotatable bonds	7	Veber ≤ 10Lead-like ≤ 7
Molar refractivityWildman–Crippen	146.89 cm³/mol	Ghose 40 to 130
Atomshydrogens included	68	Ghose 20 to 70
Heavy atoms	37	—
Fraction Csp³	0.24	—
Aromatic rings	4	—
Ringssmallest set of smallest rings	5	—
Formal charge	0	—
logSESOL estimate, log(mol/L)	−5.81	—

Details

logP and molar refractivity by atom

Each atom and its hydrogens get one of the Wildman–Crippen atom types; logP and molar refractivity are sums over the types. Point at a row to find the atom in the structure.

Atom	Type	Environment	logP	MR
C1+3 H	C8H1	methyl on an aromatic carbon	+0.454	5.635
C2	C21	aromatic carbon bearing an alkyl group	+0.136	3.509
C3+1 H	C18H1	aromatic CH	+0.281	4.407
C4+1 H	C18H1	aromatic CH	+0.281	4.407
C5	C22	aromatic carbon bearing nitrogen	+0.462	4.067
N6+1 H	N4H3	secondary aromatic amine	−0.305	3.963
C7	C5	carbon double-bonded to a heteroatom	−0.278	5.007
O8	O10	aryl carbonyl oxygen	+0.113	0.222
C9	C21	aromatic carbon bearing an alkyl group	+0.136	3.509
C10+1 H	C18H1	aromatic CH	+0.281	4.407
C11+1 H	C18H1	aromatic CH	+0.281	4.407
C12	C21	aromatic carbon bearing an alkyl group	+0.136	3.509
C13+2 H	C10H1	benzylic CH2	+0.194	4.602
N14	N7	tertiary amine	−0.319	1.839
C15+2 H	C3H1	aliphatic CH3 or CH2 bonded to a heteroatom	+0.043	4.867
C16+2 H	C3H1	aliphatic CH3 or CH2 bonded to a heteroatom	+0.043	4.867
N17	N7	tertiary amine	−0.319	1.839
C18+3 H	C3H1	aliphatic CH3 or CH2 bonded to a heteroatom	+0.166	5.924
C19+2 H	C3H1	aliphatic CH3 or CH2 bonded to a heteroatom	+0.043	4.867
C20+2 H	C3H1	aliphatic CH3 or CH2 bonded to a heteroatom	+0.043	4.867
C21+1 H	C18H1	aromatic CH	+0.281	4.407
C22+1 H	C18H1	aromatic CH	+0.281	4.407
C23+1 H	C18H1	aromatic CH	+0.281	4.407
C24	C22	aromatic carbon bearing nitrogen	+0.462	4.067
N25+1 H	N4H3	secondary aromatic amine	−0.305	3.963
C26	C22	aromatic carbon bearing nitrogen	+0.462	4.067
N27	N11	aromatic nitrogen	−0.324	2.202
C28+1 H	C18H1	aromatic CH	+0.281	4.407
C29+1 H	C18H1	aromatic CH	+0.281	4.407
C30	C20	aromatic carbon of a biaryl bond	+0.271	3.904
C31	C20	aromatic carbon of a biaryl bond	+0.271	3.904
C32+1 H	C18H1	aromatic CH	+0.281	4.407
C33+1 H	C18H1	aromatic CH	+0.281	4.407
C34+1 H	C18H1	aromatic CH	+0.281	4.407
N35	N11	aromatic nitrogen	−0.324	2.202
C36+1 H	C18H1	aromatic CH	+0.281	4.407
N37	N11	aromatic nitrogen	−0.324	2.202
Sum			4.590	146.894

Other definitions and the QED breakdown

H-bond acceptors, RDKit NumHAcceptors: 7
H-bond acceptors, RDKit Lipinski module SMARTS: 7
N and O, Lipinski: 8
H-bond donors, RDKit NumHDonors: 2
NH and OH, Lipinski: 2
TPSA with S and P: 86.28 Å²
Exact mass: 493.2590 Da
Components: 1

QED, property by property

Property	Value	Desirability
Molar mass	493.62	0.188
logP	4.59	0.652
H-bond acceptors (QED definition)	7	0.332
H-bond donors	2	0.792
TPSA	86.28	0.821
Rotatable bonds	7	0.533
Aromatic rings (QED definition)	4	0.035
Structural alerts	0	0.842

How the descriptors are defined

logP and molar refractivity follow Wildman and Crippen (J. Chem. Inf. Comput. Sci. 1999, 39, 868): every atom, hydrogens included, is assigned one of 72 atom types, defined by 110 SMARTS patterns, and the property is the sum of the type contributions. The type table and its order are RDKit's, so the numbers match RDKit's MolLogP and MolMR.

TPSA is Ertl's topological polar surface area (J. Med. Chem. 2000, 43, 3714) from nitrogen and oxygen only, as in Ertl's own implementation. The value with sulfur and phosphorus is listed under Details.

H-bond donors and acceptors are RDKit's definitions: donors are NH, OH, SH and aromatic NH; acceptors are N, O and S atoms with a free lone pair, which leaves out carboxylic acid OH groups, amide-type nitrogens and aromatic nitrogens that carry a hydrogen or a substituent, as in pyrrole or indole. Lipinski counted every NH and OH as a donor and every N and O as an acceptor, and the rule of five below uses those counts.

Rotatable bonds are acyclic single bonds between non-terminal heavy atoms, excluding bonds to triple-bonded atoms, amide, thioamide and amidine C–N bonds, and bonds to CF₃, CCl₃, CBr₃, tert-butyl and methyl groups (RDKit's strict definition).

Across the 31,358 compounds of our catalogue, logP, molar refractivity, TPSA, donors, acceptors, rotatable bonds and fraction Csp³ agree with RDKit for more than 99.9 % of structures; the exceptions are aromaticity edge cases such as fused N-oxides and large polycyclic aromatics.

What the rule sets say

Lipinski (Adv. Drug Deliv. Rev. 1997, 23, 3): poor absorption or permeation is more likely when more than one of these holds: molar mass above 500, logP above 5, more than 5 NH and OH, more than 10 N and O. Lipinski used ClogP; this page uses Wildman–Crippen logP against the same limit.

Veber (J. Med. Chem. 2002, 45, 2615): compounds with 10 or fewer rotatable bonds and a polar surface area of 140 Å² or less were likely to show good oral bioavailability in the rat.

Ghose (J. Comb. Chem. 1999, 1, 55): the qualifying range covering 80 % of known drugs, logP −0.4 to 5.6, molar refractivity 40 to 130, molar mass 160 to 480 and 20 to 70 atoms.

Egan (J. Med. Chem. 2000, 43, 3867): the edges of the absorption egg, logP 5.88 and TPSA 131.6 Å².

Lead-likeness (Teague, Davis, Leeson and Oprea, Angew. Chem. Int. Ed. 1999, 38, 3743): leads should leave room for optimisation; molar mass 250 to 350, logP up to 3.5 and at most 7 rotatable bonds, the limits SwissADME applies.

QED (Bickerton et al., Nat. Chem. 2012, 4, 90) maps molar mass, logP, acceptors, donors, polar surface area, rotatable bonds, aromatic rings and structural alerts onto desirability functions and combines them with the published mean weights.

How the radar is drawn

The radar follows SwissADME (Daina, Michielin and Zoete, Sci. Rep. 2017, 7, 42717). The shaded band on each axis is the range considered suitable for oral bioavailability: logP −0.7 to 5.0, molar mass 150 to 500 g/mol, TPSA 20 to 130 Å², logS −6 to 0, fraction Csp³ 0.25 or more and at most 9 rotatable bonds. A molecule drawn entirely inside the band is predicted to be orally bioavailable.

SwissADME uses XLOGP3; this page uses Wildman–Crippen logP. Solubility is estimated with ESOL (Delaney, J. Chem. Inf. Comput. Sci. 2004, 44, 1000), logS = 0.16 − 0.63 logP − 0.0062 MW + 0.066 RB − 0.74 AP, again with Wildman–Crippen logP in place of ClogP, so treat it as a rough estimate.