IMPPAT Phytochemical information: 
Aristolic acid

Aristolic acid
Summary

SMILES: COc1cccc2c1ccc1c2c2OCOc2cc1C(=O)O
InChI: InChI=1S/C17H12O5/c1-20-13-4-2-3-10-9(13)5-6-11-12(17(18)19)7-14-16(15(10)11)22-8-21-14/h2-7H,8H2,1H3,(H,18,19)
InChIKey: WNMKOPJJPJHXJX-UHFFFAOYSA-N
DeepSMILES: COcccccc6cccc6cOCOc5cc9C=O)O
Scaffold Graph/Node/Bond level: c1ccc2c(c1)ccc1ccc3c(c12)OCO3
Scaffold Graph/Node level: C1CCC2C(C1)CCC1CCC3OCOC3C12
Scaffold Graph level: C1CCC2C(C1)CCC1CCC3CCCC3C12
Functional groups: cOC; c1cOCO1; cC(=O)O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Phenanthrenes and derivatives
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Phenanthrenoids
NP Classifier Class: Phenanthrenes
Synonymous chemical names:
aristolic acid
External chemical identifiers:
CID:CID_119465; ChEMBL:CHEMBL486801; FDASRS:0KM5VL3A48; SureChEMBL:SCHEMBL9871957
Chemical structure download


Aristolic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 296.28
Log P RDKit 3.43
Topological polar surface area (Å2) RDKit 64.99
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 17
Number of heavy atoms RDKit 22
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 15
Number of sp3 hybridized carbon atoms RDKit 2
Shape complexity RDKit 0.12
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 3
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 3
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4


Aristolic acid
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.733906


Aristolic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.85
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.46
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No