IMPPAT Phytochemical information: 
biochanin A
biochanin A
Summary

SMILES: COc1ccc(cc1)c1coc2c(c1=O)c(O)cc(c2)O
InChI: InChI=1S/C16H12O5/c1-20-11-4-2-9(3-5-11)12-8-21-14-7-10(17)6-13(18)15(14)16(12)19/h2-8,17-18H,1H3
InChIKey: WUADCCWRTIWANL-UHFFFAOYSA-N
DeepSMILES: COcccccc6))ccoccc6=O))cO)ccc6)O
Scaffold Graph/Node/Bond level: O=c1c(-c2ccccc2)coc2ccccc12
Scaffold Graph/Node level: OC1C(C2CCCCC2)COC2CCCCC21
Scaffold Graph level: CC1C2CCCCC2CCC1C1CCCCC1
Functional groups: cOC; coc; c=O; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Isoflavonoids
ClassyFire Subclass: O-methylated isoflavonoids
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Isoflavonoids
NP Classifier Class: Isoflavones
Synonymous chemical names:
biochanin-a, Biochanin A, biochannin a, biochanin a, biochannin A, 5,7-dihydroxy-4-methoxy isoflavone, 5,7-dihydroxy-4'-methoxyisoflavone
External chemical identifiers:
CID:CID_5280373; ChEMBL:CHEMBL131921; ChEBI:CHEBI:17574; ZINC:ZINC000018847037; FDASRS:U13J6U390T; SureChEMBL:SCHEMBL61258; MolPort-000-424-557
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
biochanin A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 284.27
Log P RDKit 2.88
Topological polar surface area (Å2) RDKit 79.9
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 21
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 1
Shape complexity RDKit 0.06
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
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
biochanin A
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 Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.75601
biochanin A
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 No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.91
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No
biochanin A
Human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000342007CYP1A2700
ENSP00000362525UGT1A7700
ENSP00000361405MMP9700
ENSP00000355759PARP1700
ENSP00000346768UGT1A9700
ENSP00000343838UGT1A10700
ENSP00000236850APOA1800
ENSP00000304845UGT1A1700
ENSP00000299198CKB700
ENSP00000260630CYP1B1724
ENSP00000260433CYP19A1986
ENSP00000362549UGT1A8700
ENSP00000228606CYP27B1700
ENSP00000311032CASP3700
ENSP00000369050CYP1A1727
ENSP00000219070MMP2700
ENSP00000382342ABCC1700
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.