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
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
Phytochemical - Human target proteins supported by experimental evidence associations
Human target proteins supported by experimental evidence
IMPPAT target identifierGene identifierHGNC symbolEntrez Gene identifierSource
TAR_EXP_000983ENSG00000141458NPC14864ChEMBL, NPASS
TAR_EXP_001900ENSG00000123595RAB9A9367ChEMBL, NPASS
TAR_EXP_001906ENSG00000118777ABCG29429ChEMBL
TAR_EXP_000283ENSG00000142973CYP4B11580ChEMBL
TAR_EXP_000285ENSG00000137869CYP19A11588BindingDB, ChEMBL, NPASS
TAR_EXP_000348ENSG00000146648EGFR1956BindingDB, ChEMBL, NPASS
TAR_EXP_000390ENSG00000142208AKT1207ChEMBL
TAR_EXP_000393ENSG00000105221AKT2208ChEMBL
TAR_EXP_000395ENSG00000091831ESR12099ChEMBL, NPASS
TAR_EXP_000397ENSG00000140009ESR22100ChEMBL, NPASS
TAR_EXP_000411ENSG00000165092ALDH1A1216NPASS
TAR_EXP_000417ENSG00000111275ALDH2217ChEMBL, NPASS
TAR_EXP_000450ENSG00000004487KDM1A23028BindingDB, ChEMBL
TAR_EXP_000456ENSG00000085662AKR1B1231NPASS
TAR_EXP_000475ENSG00000120948TARDBP23435NPASS
TAR_EXP_000499ENSG00000108839ALOX12239NPASS
TAR_EXP_000567ENSG00000177628GBA12629NPASS
TAR_EXP_000604ENSG00000112164GLP1R2740NPASS
TAR_EXP_000616ENSG00000111700SLCO1B328234ChEMBL, NPASS
TAR_EXP_000623ENSG00000162365CYP4A22284541ChEMBL
TAR_EXP_000645ENSG00000113580NR3C12908ChEMBL, NPASS
TAR_EXP_000665ENSG00000167600CYP2S129785ChEMBL
TAR_EXP_000676ENSG00000072506HSD17B103028NPASS
TAR_EXP_000281ENSG00000106258CYP3A51577ChEMBL
TAR_EXP_000687ENSG00000100644HIF1A3091NPASS
TAR_EXP_000280ENSG00000160868CYP3A41576ChEMBL, NPASS
TAR_EXP_000278ENSG00000197446CYP2F11572ChEMBL
TAR_EXP_000002ENSG00000117020AKT310000ChEMBL
TAR_EXP_000004ENSG00000094631HDAC610013ChEMBL
TAR_EXP_000018ENSG00000282301CYP3A7-CYP3A51P100861540ChEMBL
TAR_EXP_000061ENSG00000134538SLCO1B110599ChEMBL, NPASS
TAR_EXP_000128ENSG00000186526CYP4F811283ChEMBL
TAR_EXP_000143ENSG00000155016CYP2U1113612ChEMBL
TAR_EXP_000170ENSG00000186104CYP2R1120227ChEMBL
TAR_EXP_000182ENSG00000023839ABCC21244ChEMBL, NPASS
TAR_EXP_000262ENSG00000140465CYP1A11543ChEMBL
TAR_EXP_000263ENSG00000140505CYP1A21544ChEMBL
TAR_EXP_000264ENSG00000138061CYP1B11545BindingDB, ChEMBL, NPASS
TAR_EXP_000265ENSG00000255974CYP2A61548ChEMBL
TAR_EXP_000266ENSG00000198077CYP2A71549ChEMBL
TAR_EXP_000269ENSG00000197838CYP2A131553ChEMBL
TAR_EXP_000270ENSG00000197408CYP2B61555ChEMBL
TAR_EXP_000271ENSG00000165841CYP2C191557ChEMBL, NPASS
TAR_EXP_000272ENSG00000138115CYP2C81558ChEMBL
TAR_EXP_000273ENSG00000138109CYP2C91559ChEMBL, NPASS
TAR_EXP_000275ENSG00000108242CYP2C181562ChEMBL
TAR_EXP_000276ENSG00000272532CYP2D61565ChEMBL, NPASS
TAR_EXP_000277ENSG00000130649CYP2E11571ChEMBL
TAR_EXP_000279ENSG00000134716CYP2J21573ChEMBL
TAR_EXP_000701ENSG00000164120HPGD3248NPASS
TAR_EXP_000282ENSG00000187048CYP4A111579ChEMBL
TAR_EXP_000709ENSG00000108786HSD17B13292ChEMBL, NPASS
TAR_EXP_001280ENSG00000198074AKR1B1057016ChEMBL, NPASS
TAR_EXP_001300ENSG00000160801PTH1R5745NPASS
TAR_EXP_001306ENSG00000196396PTPN15770ChEMBL, NPASS
TAR_EXP_001360ENSG00000004700RECQL5965NPASS
TAR_EXP_001362ENSG00000173039RELA5970NPASS
TAR_EXP_001500ENSG00000021461CYP3A4364816ChEMBL
TAR_EXP_001547ENSG00000275349SMN16606ChEMBL, NPASS
TAR_EXP_001557ENSG00000012048BRCA1672NPASS
TAR_EXP_001567ENSG00000115415STAT16772NPASS
TAR_EXP_001230ENSG00000100030MAPK15594ChEMBL, NPASS
TAR_EXP_001568ENSG00000168610STAT36774BindingDB, NPASS
TAR_EXP_001683ENSG00000133742CA1759BindingDB, ChEMBL, NPASS
TAR_EXP_001684ENSG00000104267CA2760BindingDB, ChEMBL, NPASS
TAR_EXP_001686ENSG00000167434CA4762BindingDB, ChEMBL, NPASS
TAR_EXP_001689ENSG00000168748CA7766BindingDB, ChEMBL, NPASS
TAR_EXP_001691ENSG00000074410CA12771BindingDB, ChEMBL, NPASS
TAR_EXP_001728ENSG00000176208ATAD579915ChEMBL, NPASS
TAR_EXP_001791ENSG00000186115CYP4F28529ChEMBL
TAR_EXP_001818ENSG00000159228CBR1873BindingDB, ChEMBL, NPASS
TAR_EXP_000706ENSG00000291796APEX1328NPASS
TAR_EXP_001621ENSG00000141510TP537157NPASS
TAR_EXP_001206ENSG00000042088TDP155775NPASS
TAR_EXP_001819ENSG00000159231CBR3874ChEMBL, NPASS
TAR_EXP_001170ENSG00000112033PPARD5467NPASS
TAR_EXP_001176ENSG00000073067CYP2W154905ChEMBL
TAR_EXP_000711ENSG00000086696HSD17B23294BindingDB, ChEMBL, NPASS
TAR_EXP_000715ENSG00000044574HSPA53309NPASS
TAR_EXP_000773ENSG00000169083AR367BindingDB, ChEMBL, NPASS
TAR_EXP_000786ENSG00000177606JUN3725NPASS
TAR_EXP_000819ENSG00000235268KDM4E390245NPASS
TAR_EXP_000833ENSG00000160789LMNA4000NPASS
TAR_EXP_000840ENSG00000186529CYP4F34051ChEMBL
TAR_EXP_000851ENSG00000189221MAOA4128ChEMBL
TAR_EXP_000852ENSG00000069535MAOB4129ChEMBL, NPASS
TAR_EXP_000710ENSG00000130948HSD17B33293BindingDB
TAR_EXP_000880ENSG00000118058KMT2A4297NPASS
TAR_EXP_001148ENSG00000172115CYCS54205ChEMBL, NPASS
TAR_EXP_000853ENSG00000276155MAPT4137NPASS
TAR_EXP_001106ENSG00000085563ABCB15243ChEMBL
TAR_EXP_001105ENSG00000082175PGR5241ChEMBL, NPASS
TAR_EXP_001031ENSG00000112312GMNN51053NPASS
TAR_EXP_001119ENSG00000137193PIM15292ChEMBL, NPASS
TAR_EXP_000968ENSG00000109320NFKB14790NPASS
TAR_EXP_000966ENSG00000116044NFE2L24780NPASS
TAR_EXP_000898ENSG00000103222ABCC14363ChEMBL, NPASS