IMPPAT Phytochemical information: 
Bonducellin

Bonducellin
Summary

SMILES: COc1ccc(cc1)/C=C/1\COc2c(C1=O)ccc(c2)O
InChI: InChI=1S/C17H14O4/c1-20-14-5-2-11(3-6-14)8-12-10-21-16-9-13(18)4-7-15(16)17(12)19/h2-9,18H,10H2,1H3/b12-8+
InChIKey: DLQSYZMPSWHYMW-XYOKQWHBSA-N
DeepSMILES: COcccccc6))/C=C\COccC\6=O))cccc6)O
Scaffold Graph/Node/Bond level: O=C1C(=Cc2ccccc2)COc2ccccc21
Scaffold Graph/Node level: OC1C(CC2CCCCC2)COC2CCCCC21
Scaffold Graph level: CC1C(CC2CCCCC2)CCC2CCCCC21
Functional groups: cOC; c/C=C(\C)C(=O)c; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Homoisoflavonoids
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Flavonoids
NP Classifier Class: Aurones
Synonymous chemical names:
7-hydroxy-4'-methoxyhomoisoflavone(bonducelline), bonducellin
External chemical identifiers:
CID:CID_14079439; ChEMBL:CHEMBL450675; ZINC:ZINC000014454949
Chemical structure download


Bonducellin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 282.3
Log P RDKit 3.06
Topological polar surface area (Å2) RDKit 55.76
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 21
Number of heteroatoms RDKit 4
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 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 3
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 3


Bonducellin
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 0.86


Bonducellin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME 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 -5.93
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 No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No