CHEBI:28088 - genistein

ChEBI IDCHEBI:28088
ChEBI Namegenistein
Stars
DefinitionA 7-hydroxyisoflavone with additional hydroxy groups at positions 5 and 4'. It is a phytoestrogenic isoflavone with antioxidant properties.
Secondary ChEBI IDsCHEBI:5302, CHEBI:24204, CHEBI:42763
Last Modified11 October 2021
DownloadsMolfile
FormulaC15H10O5
Net Charge0
Average Mass270.240
Monoisotopic Mass270.05282
SMILESO=c1c(-c2ccc(O)cc2)coc2cc(O)cc(O)c12
InChIInChI=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
InChIKeyTZBJGXHYKVUXJN-UHFFFAOYSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Cordyceps sinensis (ncbitaxon:72228) mycelium (BTO:0001436) PubMed (21848266) Ethanolic extract of dried mycelia
Homo sapiens (ncbitaxon:9606)
blood plasma (BTO:0000118) PubMed (17449595)
urine (BTO:0001419) PubMed (24023812)
Brassica napus (ncbitaxon:3708)
leaf lamina (BTO:0000719) MetaboLights (MTBLS309) From MetaboLights
- MetaboLights (MTBLS312) From MetaboLights
Arabidopsis thaliana (ncbitaxon:3702) cell suspension culture (BTO:0000221) MetaboLights (MTBLS311) From MetaboLights
Vigna angularis (ncbitaxon:3914) seed (BTO:0001226) PubMed (25593647)
Roles Classification
Biological Roles:
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor  A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC 5.99.1.3 (also known as topoisomerase II and as DNA gyrase), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands.
human urinary metabolite  Any metabolite (endogenous or exogenous) found in human urine samples.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
tyrosine kinase inhibitor  Any protein kinase inhibitor that interferes with the action of tyrosine kinase.
phytoestrogen  Any compound produced by a plant that happens to have estrogenic activity.
Applications:
geroprotector  Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
genistein (CHEBI:28088) has role antineoplastic agent (CHEBI:35610)
genistein (CHEBI:28088) has role EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor (CHEBI:50750)
genistein (CHEBI:28088) has role geroprotector (CHEBI:176497)
genistein (CHEBI:28088) has role human urinary metabolite (CHEBI:84087)
genistein (CHEBI:28088) has role phytoestrogen (CHEBI:76989)
genistein (CHEBI:28088) has role plant metabolite (CHEBI:76924)
genistein (CHEBI:28088) has role tyrosine kinase inhibitor (CHEBI:38637)
genistein (CHEBI:28088) is a 7-hydroxyisoflavones (CHEBI:55465)
genistein (CHEBI:28088) is conjugate acid of genistein(1−) (CHEBI:74224)
Incoming Relation(s)
2-hydroxy-2,3-dihydrogenistein (CHEBI:31080) has functional parent genistein (CHEBI:28088)
2'-hydroxygenistein (CHEBI:70031) has functional parent genistein (CHEBI:28088)
5,7,4'-trihydroxy-6,8-diprenylisoflavone (CHEBI:66263) has functional parent genistein (CHEBI:28088)
genistein 4',7-disulfate (CHEBI:55454) has functional parent genistein (CHEBI:28088)
genistein 7-O-β-D-glucoside (CHEBI:27514) has functional parent genistein (CHEBI:28088)
genistein 8-C-glucoside (CHEBI:5304) has functional parent genistein (CHEBI:28088)
genistein sulfate (CHEBI:233021) has functional parent genistein (CHEBI:28088)
genistin 7-O-gentiobioside (CHEBI:145776) has functional parent genistein (CHEBI:28088)
prunetin (CHEBI:8600) has functional parent genistein (CHEBI:28088)
talosin A (CHEBI:66186) has functional parent genistein (CHEBI:28088)
talosin B (CHEBI:66187) has functional parent genistein (CHEBI:28088)
genistein(1−) (CHEBI:74224) is conjugate base of genistein (CHEBI:28088)
IUPAC Name 
5,7-dihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one
Synonyms  Source
GenisteinKEGG COMPOUND
5,7,4'-TrihydroxyisoflavoneKEGG COMPOUND
GENISTEINPDBeChem
4',5,7-trihydroxyisoflavoneChemIDplus
5,7-dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-oneChEBI
4',5,7-trihydroxyisoflavoneChEBI
Brand Names  Source
PrunetolDrugBank
SophoricolDrugBank
Manual XrefsDatabases
C06563KEGG COMPOUND
GENPDBeChem
DB01645DrugBank
GenisteinWikipedia
CPD-3141MetaCyc
C00002526KNApSAcK
HMDB0003217HMDB
4444448ChemSpider
LSM-5549LINCS
FDB011828FooDB
LMPK12050218LIPID MAPS
D11680KEGG DRUG
Registry NumbersSources
Reaxys:263823Reaxys
CAS:446-72-0KEGG COMPOUND
CAS:446-72-0ChemIDplus
Citations