IMPPAT Phytochemical information: 
Aristolodione
Aristolodione
Summary

SMILES: COc1c(O)cc2c3c1c1ccccc1cc3N(C(=O)C2=O)C
InChI: InChI=1S/C18H13NO4/c1-19-12-7-9-5-3-4-6-10(9)15-14(12)11(16(21)18(19)22)8-13(20)17(15)23-2/h3-8,20H,1-2H3
InChIKey: JGDZUWXHWYXMSD-UHFFFAOYSA-N
DeepSMILES: COccO)cccc6cccccc6cc%10NC=O)C%14=O)))C
Scaffold Graph/Node/Bond level: O=C1Nc2cc3ccccc3c3cccc(c23)C1=O
Scaffold Graph/Node level: OC1NC2CC3CCCCC3C3CCCC(C1O)C23
Scaffold Graph level: CC1CC2CC3CCCCC3C3CCCC(C1C)C23
Functional groups: cOC; cO; cC(=O)C(=O)N(C)c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Aporphines
ClassyFire Subclass: 4,5-dioxoaporphines
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Aporphine alkaloids
Synonymous chemical names:
(2-hydroxy-1-methoxy-6-metyl-4h-dibenzo(de,g)quinoline-4,5-(6h)-dione), piperadione
External chemical identifiers:
CID:CID_184116; ChEBI:CHEBI:174938
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Aristolodione
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 307.31
Log P RDKit 2.87
Topological polar surface area (Å2) RDKit 66.84
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 5
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 16
Number of sp3 hybridized carbon atoms RDKit 2
Shape complexity RDKit 0.11
Number of rotatable bonds RDKit 0
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
Aristolodione
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 0.55
Aristolodione
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
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 -6.03
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 3
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No