IMPPAT Phytochemical information: 
Genistein
Genistein
Summary

SMILES: Oc1ccc(cc1)c1coc2c(c1=O)c(O)cc(c2)O
InChI: InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)11-7-20-13-6-10(17)5-12(18)14(13)15(11)19/h1-7,16-18H
InChIKey: TZBJGXHYKVUXJN-UHFFFAOYSA-N
DeepSMILES: Occcccc6))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: c=O; cO; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Isoflavonoids
ClassyFire Subclass: Isoflav-2-enes
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Isoflavonoids
NP Classifier Class: Isoflavones
Synonymous chemical names:
4,5,7-trihydroxyisoflavone, 5,7,4'-trihydroxyisoflavone(genistein), genistein
External chemical identifiers:
CID:5280961; ChEMBL:CHEMBL44; ChEBI:28088; ZINC:ZINC000018825330; FDASRS:DH2M523P0H; SureChEMBL:SCHEMBL19166; MolPort-000-003-911
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Genistein
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 270.24
Log P RDKit 2.58
Topological polar surface area (Å2) RDKit 90.9
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 20
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 0
Shape complexity RDKit 0
Number of rotatable bonds RDKit 1
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
Genistein
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 0.6318
Genistein
ADMET 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 -6.05
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 0.0
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
Genistein
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000000442ESRRA893
ENSP00000003084CFTR961
ENSP00000155840KCNQ1800
ENSP00000162749TNFRSF1A800
ENSP00000206249ESR1996
ENSP00000215832MAPK1765
ENSP00000216117HMOX1839
ENSP00000216862CYP24A1938
ENSP00000219070MMP2947
ENSP00000221930TGFB1859
ENSP00000222304HAMP817
ENSP00000225831CCL2932
ENSP00000226444SULT1E1700
ENSP00000226730IL2818
ENSP00000227507CCND1864
ENSP00000228606CYP27B1938
ENSP00000228682GLI1800
ENSP00000228872CDKN1B854
ENSP00000229135IFNG806
ENSP00000237014TTR800
ENSP00000237612ABCG2912
ENSP00000239849TNFSF11846
ENSP00000241261TNFSF10741
ENSP00000241453FLT3800
ENSP00000244741CDKN1A862
ENSP00000245919FOSB800
ENSP00000251849RAF1735
ENSP00000252723EPO800
ENSP00000252809GDF15837
ENSP00000256078KRAS838
ENSP00000256429MBD2700
ENSP00000257189DSG3812
ENSP00000257904CDK4733
ENSP00000258743IL6952
ENSP00000260433CYP19A1962
ENSP00000260630CYP1B1727
ENSP00000261769CDH1868
ENSP00000262445MAP2K4817
ENSP00000262461SLC12A2824
ENSP00000262735PPARA825
ENSP00000262839TRPC5800
ENSP00000262948MAP2K2700
ENSP00000263025MAPK3756
ENSP00000263341IL1B855
ENSP00000263431PRKCG865
ENSP00000264498FGF2806
ENSP00000264657STAT3863
ENSP00000264709DNMT3A839
ENSP00000265171EGF894
ENSP00000265641CPT1A824
ENSP00000267163RB1700
ENSP00000269305TP53882
ENSP00000269571ERBB2946
ENSP00000270142SOD1824
ENSP00000270202AKT1960
ENSP00000275493EGFR899
ENSP00000278616ATM942
ENSP00000282077PDK1743
ENSP00000283916TMPRSS11D786
ENSP00000285379CA2824
ENSP00000287820PPARG964
ENSP00000288207CCNB2853
ENSP00000294728VCAM1822
ENSP00000295453ALPPL2844
ENSP00000297494NOS3978
ENSP00000299198CKB700
ENSP00000299421ILK824
ENSP00000300093PLK1800
ENSP00000302486MAP2K1763
ENSP00000302665IGF1882
ENSP00000304845UGT1A1732
ENSP00000305422CEBPB824
ENSP00000305651CXCL10800
ENSP00000309124OLR1800
ENSP00000309572TERT824
ENSP00000309845HRAS824
ENSP00000311032CASP3949
ENSP00000312652LEP781
ENSP00000313007PABPC1843
ENSP00000314151KLK3867
ENSP00000318820TPO700
ENSP00000318822BID700
ENSP00000320940NCOA1824
ENSP00000321656CDC25C844
ENSP00000321999PTH1R800
ENSP00000324806GSK3B727
ENSP00000326366PSEN1800
ENSP00000327652800
ENSP00000329357SP1700
ENSP00000330237CASP9722
ENSP00000332816PTK2B937
ENSP00000333685MAPK11700
ENSP00000337459NOS1786
ENSP00000337915CYP3A4775
ENSP00000338018HIF1A815
ENSP00000338157ZBTB16839
ENSP00000339527FOXO3955
ENSP00000341189PTK2943
ENSP00000342007CYP1A2943
ENSP00000342307FOXM1842
ENSP00000343838UGT1A10732
ENSP00000343925ESR2996
ENSP00000344352ATF3824
ENSP00000344609BTG3700
ENSP00000346768UGT1A9726
ENSP00000347379OCLN824
ENSP00000347942RET800
ENSP00000348069SREBF1816
ENSP00000350941SRC889
ENSP00000352516DNMT1846
ENSP00000354511COMT727
ENSP00000355627AGT812
ENSP00000355759PARP1779
ENSP00000356438PTGS2853
ENSP00000358548NRAS800
ENSP00000360020DIRAS3800
ENSP00000360025GADD45A854
ENSP00000360266JUN757
ENSP00000360317CYP2C8800
ENSP00000361125VEGFA786
ENSP00000361405MMP9948
ENSP00000362525UGT1A7732
ENSP00000362549UGT1A8726
ENSP00000363081DKK1824
ENSP00000363822AR959
ENSP00000363827HSPG2800
ENSP00000363965ALPL822
ENSP00000366936SHB800
ENSP00000367207MYC848
ENSP00000368683EDN1822
ENSP00000369050CYP1A1988
ENSP00000369547S100G800
ENSP00000369816SHBG866
ENSP00000371152ASAH1824
ENSP00000372023CHEK2938
ENSP00000375881ALPP844
ENSP00000378400LIMA1835
ENSP00000378699CDK1734
ENSP00000379140CXCL12700
ENSP00000382342ABCC1700
ENSP00000386884CXCR4938
ENSP00000387230UPP2800
ENSP00000387699CREB1818
ENSP00000388648CHEK1824
ENSP00000398632CD44838
ENSP00000398698TNF744
ENSP00000399968NCOA2800
ENSP00000401802PSMC6824
ENSP00000409007GDNF800
ENSP00000411532TOP2A924
ENSP00000411593GLRA1700
ENSP00000416293SLC2A1725
ENSP00000416330TGFBI800
ENSP00000417281MDM2817
ENSP00000418532UGT1A3700
ENSP00000420168GSTA2847
ENSP00000466799HSD17B1738
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.