IMPPAT Phytochemical information: 
Aristolochic acid IV
Aristolochic acid IV
Summary

SMILES: COc1cc(OC)c2c(c1)c1c3OCOc3cc(c1c(c2)[N+](=O)[O-])C(=O)O
InChI: InChI=1S/C18H13NO8/c1-24-8-3-10-9(13(4-8)25-2)5-12(19(22)23)15-11(18(20)21)6-14-17(16(10)15)27-7-26-14/h3-6H,7H2,1-2H3,(H,20,21)
InChIKey: GYBINMVKWZEICQ-UHFFFAOYSA-N
DeepSMILES: COcccOC))ccc6)ccOCOc5ccc9cc%13)[N+]=O)[O-]))))C=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; c[N+](=O)[O-]; cC(=O)O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Phenanthrenes and derivatives
ClassyFire Subclass: Aristolochic acids and derivatives
Synonymous chemical names:
aristolochic acid iv, aristolochic acid iv methylether
External chemical identifiers:
CID:CID_167493; ChEMBL:CHEMBL465004
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Aristolochic acid IV
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 371.3
Log P RDKit 3.35
Topological polar surface area (Å2) RDKit 117.36
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 1
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 3
Shape complexity RDKit 0.17
Number of rotatable bonds RDKit 4
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
Aristolochic acid IV
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.42
Aristolochic acid IV
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.06
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 3
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No