GEN

GENISTEIN

Created: 1999-07-28
Last modified:  2020-06-05

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Chemical Details

Formal Charge0
Atom Count30
Chiral Atom Count0
Bond Count32
Aromatic Bond Count18
2D diagram of GEN
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Chemical Component Summary

NameGENISTEIN
Synonyms5,7-DIHYDROXY-3-(4-HYDROXYPHENYL)-4H-1-BENZOPYRAN-4-ONE; 4',5,7-TRIHYDROXYISOFLAVONE; PRUNETOL; GENISTEOL
Systematic Name (OpenEye OEToolkits)5,7-dihydroxy-3-(4-hydroxyphenyl)chromen-4-one
FormulaC15 H10 O5
Molecular Weight270.237
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04O=C1c3c(OC=C1c2ccc(O)cc2)cc(O)cc3O
SMILESCACTVS3.341Oc1ccc(cc1)C2=COc3cc(O)cc(O)c3C2=O
SMILESOpenEye OEToolkits1.5.0c1cc(ccc1C2=COc3cc(cc(c3C2=O)O)O)O
Canonical SMILESCACTVS3.341 Oc1ccc(cc1)C2=COc3cc(O)cc(O)c3C2=O
Canonical SMILESOpenEye OEToolkits1.5.0 c1cc(ccc1C2=COc3cc(cc(c3C2=O)O)O)O
InChIInChI1.03 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
InChIKeyInChI1.03 TZBJGXHYKVUXJN-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank IDDB01645 
NameGenistein
Groups investigational
DescriptionAn isoflavonoid derived from soy products. It inhibits protein-tyrosine kinase and topoisomerase-II (DNA topoisomerases, type II) activity and is used as an antineoplastic and antitumor agent. Experimentally, it has been shown to induce G2 phase arrest in human and murine cell lines. Additionally, genistein has antihelmintic activity. It has been determined to be the active ingredient in <I>Felmingia vestita</I>, which is a plant traditionally used against worms. It has shown to be effective in the treatment of common liver fluke, pork trematode and poultry cestode. Further, genistein is a phytoestrogen which has selective estrogen receptor modulator properties. It has been investigated in clinical trials as an alternative to classical hormone therapy to help prevent cardiovascular disease in postmenopausal women [A14417]. Natural sources of genistein include tofu, fava beans, soybeans, kudzu, and lupin.
Synonyms
  • 5,7-dihydroxy-3-(4-hydroxyphenyl)-chromen-4-one
  • 5,7,4'-trihydroxyisoflavone
  • Genisterin
  • Genisteol
  • Genistein
Brand Names
  • Fosteum
  • Vp-gstn
  • Tempo Hot Flash Relief
IndicationCurrently Genistein is being studied in clinical trials as a treatment for prostate cancer.
Categories
  • Anticarcinogenic Agents
  • Antineoplastic Agents
  • BCRP/ABCG2 Inhibitors
  • Benzopyrans
  • Chromones
CAS number446-72-0

Drug Targets

NameTarget SequencePharmacological ActionActions
Nuclear receptor coactivator 1MSGLGDSSSDPANPDSHKRKGSPCDTLASSTEKRRREQENKYLEELAELL...unknown
Estrogen receptor alphaMTMTLHTKASGMALLHQIQGNELEPLNRPQLKIPLERPLGEVYLDSSKPA...unknown
Nuclear receptor coactivator 2MSGMGENTSDPSRAETRKRKECPDQLGPSPKRNTEKRNREQENKYIEELA...unknown
Steroid hormone receptor ERR2MSSDDRHLGSSCGSFIKTEPSSPSSGIDALSHHSPSGSSDASGGFGLALG...unknownagonist
Steroid hormone receptor ERR1MSSQVVGIEPLYIKAEPASPDSPKGSSETETEPPVALAPGPAPTRCLPGH...unknownagonist
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL44
PubChem 5280961
ChEMBL CHEMBL44
ChEBI CHEBI:28088
CCDC/CSD GENIST01, ZIKPIU01, ZIKPIU, GENIST, EJEQER, EJEQUH, EZEJOK, YIKRAN, BOLBAH, OTIMUC, GENIST02, OQIWOD, CANPIU
COD 7211144, 7211143, 2019219