IMPPAT Phytochemical information: 
Aristolochic acids
Aristolochic acids
Summary

SMILES: [O-][N+](=O)c1cc2ccccc2c2c1c(cc1c2OCO1)C(=O)O.COc1cccc2c1cc([N+](=O)[O-])c1c2c2OCOc2cc1C(=O)O.COc1cccc2c1cc([N+](=O)[O-])c1c2c2OCOc2cc1C(=O)O
InChI: InChI=1S/2C17H11NO7.C16H9NO6/c2*1-23-12-4-2-3-8-9(12)5-11(18(21)22)14-10(17(19)20)6-13-16(15(8)14)25-7-24-13;18-16(19)10-6-12-15(23-7-22-12)14-9-4-2-1-3-8(9)5-11(13(10)14)17(20)21/h2*2-6H,7H2,1H3,(H,19,20);1-6H,7H2,(H,18,19)
InChIKey: FGGYSLIDOXIJNP-UHFFFAOYSA-N
DeepSMILES: [O-][N+]=O)cccccccc6cc%10cccc6OCO5))))))C=O)O.COcccccc6cc[N+]=O)[O-]))cc6cOCOc5cc9C=O)O.COcccccc6cc[N+]=O)[O-]))cc6cOCOc5cc9C=O)O
Functional groups: c[N+](=O)[O-]; c1cOCO1; cC(=O)O; cOC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Phenanthrenes and derivatives
ClassyFire Subclass: Aristolochic acids and derivatives
Synonymous chemical names:
aristolochic acids
External chemical identifiers:
CID:CID_56841539
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Aristolochic acids
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 993.8
Log P RDKit 10
Topological polar surface area (Å2) RDKit 315.16
Number of hydrogen bond acceptors RDKit 17
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 50
Number of heavy atoms RDKit 73
Number of heteroatoms RDKit 23
Number of nitrogen atoms RDKit 3
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 45
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.1
Number of rotatable bonds RDKit 8
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 9
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 9
Total number of rings RDKit 12
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 12
Aristolochic acids
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 4
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.07
Aristolochic acids
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.11
Solubility class [ESOL] SwissADME Insoluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -4.76
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 3
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes