CHEBI:28088 - genistein

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ChEBI Name genistein
ChEBI ID CHEBI:28088
Definition A 7-hydroxyisoflavone with additional hydroxy groups at positions 5 and 4'. It is a phytoestrogenic isoflavone with antioxidant properties.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:42763, CHEBI:5302, CHEBI:24204
Supplier Information ChemicalBook:CB6163787, eMolecules:532754, Selleckchem:Genistein, ZINC000018825330
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Genistein (C15H10O5) is a naturally occurring compound that structurally belongs to a class of compounds known as isoflavones. It is described as an angiogenesis inhibitor and a phytoestrogen. It was first isolated in 1899 from the dyer's broom, Genista tinctoria; hence, the chemical name. The compound structure was established in 1926, when it was found to be identical with that of prunetol. It was chemically synthesized in 1928. It has been shown to be the primary secondary metabolite of the Trifolium species and Glycine max.
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Formula C15H10O5
Net Charge 0
Average Mass 270.240
Monoisotopic Mass 270.05282
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
SMILES OC1=CC=C(C=C1)C1=COC2=C(C(O)=CC(O)=C2)C1=O
Metabolite of Species Details
Arabidopsis thaliana (NCBI:txid3702) Found in cell suspension culture (BTO:0000221). From MetaboLights See: MetaboLights Study
Brassica napus (NCBI:txid3708) Found in leaf lamina (BTO:0000719). From MetaboLights See: MetaboLights Study
Brassica napus (NCBI:txid3708) From MetaboLights See: MetaboLights Study
Vigna angularis (NCBI:txid3914) Found in seed (BTO:0001226). See: PubMed
Cordyceps sinensis (NCBI:txid72228) Found in mycelium (BTO:0001436). Ethanolic extract of dried mycelia See: PubMed
Homo sapiens (NCBI:txid9606) Found in blood plasma (BTO:0000118). See: PubMed
Homo sapiens (NCBI:txid9606) Found in urine (BTO:0001419). See: PubMed
Roles Classification
Biological Role(s): tyrosine kinase inhibitor
Any protein kinase inhibitor that interferes with the action of tyrosine kinase.
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.
phytoestrogen
Any compound produced by a plant that happens to have estrogenic activity.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
geroprotector
Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 2'-hydroxygenistein (CHEBI:70031) has functional parent genistein (CHEBI:28088)
2-hydroxy-2,3-dihydrogenistein (CHEBI:31080) 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 Sources
4',5,7-trihydroxyisoflavone ChEBI
4',5,7-trihydroxyisoflavone ChemIDplus
5,7,4'-Trihydroxyisoflavone KEGG COMPOUND
5,7-dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one ChEBI
Genistein KEGG COMPOUND
GENISTEIN PDBeChem
Brand Names Sources
Prunetol DrugBank
Sophoricol DrugBank
Manual Xrefs Databases
4444448 ChemSpider
C00002526 KNApSAcK
C06563 KEGG COMPOUND
CPD-3141 MetaCyc
D11680 KEGG DRUG
DB01645 DrugBank
FDB011828 FooDB
GEN PDBeChem
Genistein Wikipedia
HMDB0003217 HMDB
LMPK12050218 LIPID MAPS
LSM-5549 LINCS
View more database links
Registry Numbers Types Sources
263823 Reaxys Registry Number Reaxys
446-72-0 CAS Registry Number KEGG COMPOUND
446-72-0 CAS Registry Number ChemIDplus
Citations
Werner N, Werten S, Hoppen J, Palm GJ, Göttfert M, Hinrichs W (2022)
The induction mechanism of the flavonoid-responsive regulator FrrA.
The FEBS journal 289, 507-518 [PubMed:34314575]
[show Abstract]
Keller AN, Eckle SB, Xu W, Liu L, Hughes VA, Mak JY, Meehan BS, Pediongco T, Birkinshaw RW, Chen Z, Wang H, D'Souza C, Kjer-Nielsen L, Gherardin NA, Godfrey DI, Kostenko L, Corbett AJ, Purcell AW, Fairlie DP, McCluskey J, Rossjohn J (2017)
Drugs and drug-like molecules can modulate the function of mucosal-associated invariant T cells.
Nature immunology 18, 402-411 [PubMed:28166217]
[show Abstract]
Cassetta A, Stojan J, Krastanova I, Kristan K, Brunskole Švegelj M, Lamba D, Lanišnik Rižner T (2017)
Structural basis for inhibition of 17β-hydroxysteroid dehydrogenases by phytoestrogens: The case of fungal 17β-HSDcl.
The Journal of steroid biochemistry and molecular biology 171, 80-93 [PubMed:28259640]
[show Abstract]
Lee EB, Ahn D, Kim BJ, Lee SY, Seo HW, Cha YS, Jeon H, Eun JS, Cha DS, Kim DK (2015)
Genistein from Vigna angularis Extends Lifespan in Caenorhabditis elegans.
Biomolecules & therapeutics 23, 77-83 [PubMed:25593647]
[show Abstract]
Yokoyama T, Kosaka Y, Mizuguchi M (2015)
Structural Insight into the Interactions between Death-Associated Protein Kinase 1 and Natural Flavonoids.
Journal of medicinal chemistry 58, 7400-7408 [PubMed:26322379]
[show Abstract]
Yu D, Shin HS, Lee YS, Lee D, Kim S, Lee YC (2014)
Genistein attenuates cancer stem cell characteristics in gastric cancer through the downregulation of Gli1.
Oncology reports 31, 673-678 [PubMed:24297371]
[show Abstract]
Tian T, Li J, Li B, Wang Y, Li M, Ma D, Wang X (2014)
Genistein exhibits anti-cancer effects via down-regulating FoxM1 in H446 small-cell lung cancer cells.
Tumour biology : the journal of the International Society for Oncodevelopmental Biology and Medicine 35, 4137-4145 [PubMed:24379139]
[show Abstract]
Bouatra S, Aziat F, Mandal R, Guo AC, Wilson MR, Knox C, Bjorndahl TC, Krishnamurthy R, Saleem F, Liu P, Dame ZT, Poelzer J, Huynh J, Yallou FS, Psychogios N, Dong E, Bogumil R, Roehring C, Wishart DS (2013)
The human urine metabolome.
PloS one 8, e73076 [PubMed:24023812]
[show Abstract]
Pandit NT, Patravale VB (2011)
Design and optimization of a novel method for extraction of genistein.
Indian journal of pharmaceutical sciences 73, 184-192 [PubMed:22303062]
[show Abstract]
Trivella DB, Bleicher L, Palmieri Lde C, Wiggers HJ, Montanari CA, Kelly JW, Lima LM, Foguel D, Polikarpov I (2010)
Conformational differences between the wild type and V30M mutant transthyretin modulate its binding to genistein: implications to tetramer stability and ligand-binding.
Journal of structural biology 170, 522-531 [PubMed:20211733]
[show Abstract]
Lu H, Shi JX, Zhang DM, Chen HL, Qi M, Yin HX (2009)
Genistein, a soybean isoflavone, reduces the production of pro-inflammatory and adhesion molecules induced by hemolysate in brain microvascular endothelial cells.
Acta neurologica Belgica 109, 32-37 [PubMed:19402570]
[show Abstract]
Zhang M, Ikeda K, Xu JW, Yamori Y, Gao XM, Zhang BL (2009)
Genistein suppresses adipogenesis of 3T3-L1 cells via multiple signal pathways.
Phytotherapy research : PTR 23, 713-718 [PubMed:19107852]
[show Abstract]
Majid S, Kikuno N, Nelles J, Noonan E, Tanaka Y, Kawamoto K, Hirata H, Li LC, Zhao H, Okino ST, Place RF, Pookot D, Dahiya R (2008)
Genistein induces the p21WAF1/CIP1 and p16INK4a tumor suppressor genes in prostate cancer cells by epigenetic mechanisms involving active chromatin modification.
Cancer research 68, 2736-2744 [PubMed:18413741]
[show Abstract]
Helferich WG, Andrade JE, Hoagland MS (2008)
Phytoestrogens and breast cancer: a complex story.
Inflammopharmacology 16, 219-226 [PubMed:18815740]
[show Abstract]
Yu JY, Lee JJ, Lim Y, Kim TJ, Jin YR, Sheen YY, Yun YP (2008)
Genistein inhibits rat aortic smooth muscle cell proliferation through the induction of p27kip1.
Journal of pharmacological sciences 107, 90-98 [PubMed:18490856]
[show Abstract]
Nettles KW, Bruning JB, Gil G, Nowak J, Sharma SK, Sharma SK, Hahm JB, Kulp K, Hochberg RB, Zhou H, Katzenellenbogen JA, Katzenellenbogen BS, Kim Y, Joachmiak A, Greene GL (2008)
NFkappaB selectivity of estrogen receptor ligands revealed by comparative crystallographic analyses.
Nature chemical biology 4, 241-247 [PubMed:18344977]
[show Abstract]
Si H, Liu D (2007)
Phytochemical genistein in the regulation of vascular function: new insights.
Current medicinal chemistry 14, 2581-2589 [PubMed:17979711]
[show Abstract]
Ronis MJ, Little JM, Barone GW, Chen G, Radominska-Pandya A, Badger TM (2006)
Sulfation of the isoflavones genistein and daidzein in human and rat liver and gastrointestinal tract.
Journal of medicinal food 9, 348-355 [PubMed:17004897]
[show Abstract]
Huang X, Chen S, Xu L, Liu Y, Deb DK, Platanias LC, Bergan RC (2005)
Genistein inhibits p38 map kinase activation, matrix metalloproteinase type 2, and cell invasion in human prostate epithelial cells.
Cancer research 65, 3470-3478 [PubMed:15833883]
[show Abstract]
Li Y, Ahmed F, Ali S, Philip PA, Kucuk O, Sarkar FH (2005)
Inactivation of nuclear factor kappaB by soy isoflavone genistein contributes to increased apoptosis induced by chemotherapeutic agents in human cancer cells.
Cancer research 65, 6934-6942 [PubMed:16061678]
[show Abstract]
Li M, Zhang Z, Hill DL, Chen X, Wang H, Zhang R (2005)
Genistein, a dietary isoflavone, down-regulates the MDM2 oncogene at both transcriptional and posttranslational levels.
Cancer research 65, 8200-8208 [PubMed:16166295]
[show Abstract]
D'Souza N, Skonberg DI, Camire ME, Guthrie KE, Malison J, Lima L (2005)
Influence of dietary genistein levels on tissue genistein deposition and on the physical, chemical, and sensory quality of rainbow trout, Oncorhynchus mykiss.
Journal of agricultural and food chemistry 53, 3631-3636 [PubMed:15853412]
[show Abstract]
Crisafulli A, Altavilla D, Marini H, Bitto A, Cucinotta D, Frisina N, Corrado F, D'Anna R, Squadrito G, Adamo EB, Marini R, Romeo A, Cancellieri F, Buemi M, Squadrito F (2005)
Effects of the phytoestrogen genistein on cardiovascular risk factors in postmenopausal women.
Menopause (New York, N.Y.) 12, 186-192 [PubMed:15772566]
[show Abstract]
Kim S, Shin HJ, Kim SY, Kim JH, Lee YS, Kim DH, Lee MO (2004)
Genistein enhances expression of genes involved in fatty acid catabolism through activation of PPARalpha.
Molecular and cellular endocrinology 220, 51-58 [PubMed:15196699]
[show Abstract]
Sonee M, Sum T, Wang C, Mukherjee SK (2004)
The soy isoflavone, genistein, protects human cortical neuronal cells from oxidative stress.
Neurotoxicology 25, 885-891 [PubMed:15288519]
[show Abstract]
Manas ES, Xu ZB, Unwalla RJ, Somers WS (2004)
Understanding the selectivity of genistein for human estrogen receptor-beta using X-ray crystallography and computational methods.
Structure (London, England : 1993) 12, 2197-2207 [PubMed:15576033]
[show Abstract]
Ohno S, Nakajima Y, Inoue K, Nakazawa H, Nakajin S (2003)
Genistein administration decreases serum corticosterone and testosterone levels in rats.
Life sciences 74, 733-742 [PubMed:14654166]
[show Abstract]
Wisniewski AB, Klein SL, Lakshmanan Y, Gearhart JP (2003)
Exposure to genistein during gestation and lactation demasculinizes the reproductive system in rats.
The Journal of urology 169, 1582-1586 [PubMed:12629420]
[show Abstract]
Okamoto F, Okabe K, Kajiya H (2001)
Genistein, a soybean isoflavone, inhibits inward rectifier K(+) channels in rat osteoclasts.
The Japanese journal of physiology 51, 501-509 [PubMed:11564287]
[show Abstract]
Sallusto F, Poupot R, Clergue M, DePalma R, Fournié JJ (2000)
A flavonoid sulfate antigen activates human alphabeta CD8+ Th2 lymphocytes in pollen allergy.
European journal of immunology 30, 964-968 [PubMed:10741415]
[show Abstract]
Casagrande F, Darbon JM (2000)
p21CIP1 is dispensable for the G2 arrest caused by genistein in human melanoma cells.
Experimental cell research 258, 101-108 [PubMed:10912792]
[show Abstract]
Pike AC, Brzozowski AM, Hubbard RE, Bonn T, Thorsell AG, Engström O, Ljunggren J, Gustafsson JA, Carlquist M (1999)
Structure of the ligand-binding domain of oestrogen receptor beta in the presence of a partial agonist and a full antagonist.
The EMBO journal 18, 4608-4618 [PubMed:10469641]
[show Abstract]
Last Modified
11 October 2021