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Record Information
Version1.0
Created at2006-05-22 15:12:42 UTC
Updated at2021-08-10 02:54:36 UTC
NP-MRD IDNP0000024
Secondary Accession NumbersNone
Natural Product Identification
Common NameGenistein
DescriptionGenistein is one of several known isoflavones. Isoflavones compounds, such as genistein and daidzein, are found in a number of plants, but soybeans and soy products like tofu and textured vegetable protein are the primary food source. Genistein is a natural bioactive compound derived from legumes and has drawn because of its potentially beneficial effects on some human degenerative diseases. It has a weak estrogenic effect and is a well-known non-specific tyrosine kinase inhibitor at pharmacological doses. Epidemiological studies show that genistein intake is inversely associated with the risk of cardiovascular diseases. Data suggests a protective role of genistein in cardiovascular events. However, the mechanisms of the genistein action on vascular protective effects are unclear. Past extensive studies exploring its hypolipidemic effect resulted in contradictory data. Genistein also is a relatively poor antioxidant. However, genistein protects against pro-inflammatory factor-induced vascular endothelial barrier dysfunction and inhibits leukocyte-endothelium interaction, thereby modulating vascular inflammation, a major event in the pathogenesis of atherosclerosis. Genistein exerts a non-genomic action by targeting on important signaling molecules in vascular endothelial cells (ECs). Genistein rapidly activates endothelial nitric oxide synthase and production of nitric oxide in ECs. This genistein effect is novel since it is independent of its known effects, but mediated by the cyclic adenosine monophosphate/protein kinase A (cAMP/PKA) cascade. Genistein directly stimulates the plasma membrane-associated adenylate cyclases, leading to activation of the cAMP signaling pathway. In addition, genistein activates peroxisome proliferator-activated receptors, ligand-activated nuclear receptors important to normal vascular function. Furthermore, genistein reduces reactive oxygen species (ROS) by attenuating the expression of ROS-producing enzymes. These findings reveal the roles for genistein in the regulation of vascular function and provide a basis for further investigating its therapeutic potential for inflammatory-related vascular disease. (PMID: 17979711 ). Genistein is a biomarker for the consumption of soy beans and other soy products.
Structure
Data?1628564076
Synonyms
ValueSource
4',5,7-TrihydroxyisoflavoneChEBI
5,7,4'-TrihydroxyisoflavoneChEBI
5,7-Dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-oneChEBI
PrunetolChEBI
SophoricolChEBI
4',5, 7-TrihydroxyisoflavoneHMDB
4',5,7-Trihydroxy-isoflavoneHMDB
4,5,7-Trihydroxy iso-flavoneHMDB
Genistein 85% HPLCHMDB
GenisteolHMDB
GenisterinHMDB
GenesteinHMDB
Chemical FormulaC15H10O5
Average Mass270.2400 Da
Monoisotopic Mass270.05282 Da
IUPAC Name5,7-dihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one
Traditional Namegenistein
CAS Registry Number446-72-0
SMILES
[H]OC1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])OC2=C([H])C(O[H])=C([H])C(O[H])=C2C1=O
InChI Identifier
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
InChI KeyTZBJGXHYKVUXJN-UHFFFAOYSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 150 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 250 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 175 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 225 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, dmso, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 150 MHz, dmso, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 250 MHz, dmso, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 175 MHz, dmso, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, dmso, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, dmso, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 225 MHz, dmso, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, dmso, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, dmso, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25 MHz, dmso, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, dmso, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, dmso, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, dmso, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, dmso, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, dmso, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, dmso, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, dmso, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, dmso, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, dmso, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, dmso, predicted)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol, simulated)V.dorna832021-07-19View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol, simulated)V.dorna832021-09-07View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol, experimental)V.dorna832021-09-07View Spectrum
Species
Species of Origin
Species NameSourceReference
Acacia aduncaPlant
Acacia baileyanaPlant
Acacia binervataPlant
Acacia calamifoliaPlant
Acacia cardiophyllaPlant
Acacia chrysotrichaPlant
Acacia clunies-rossiaePlant
Acacia concurrensPlant
Acacia constableiPlant
Acacia cultriformisPlant
Acacia dealbataPlant
Acacia deaneiPlant
Acacia decurrensPlant
Acacia elataPlant
Acacia falciformisPlant
Acacia filicifoliaPlant
Acacia fimbriataPlant
Acacia holosericeaPlant
Acacia irrorataPlant
Acacia kettlewelliaePlant
Acacia lanigeraPlant
Acacia leucocladaPlant
Acacia longifoliaPlant
Acacia mabellaePlant
Acacia mearnsiiPlant
Acacia melanoxylonPlant
Acacia mollifoliaPlant
Acacia neriifoliaPlant
Acacia obtusifoliaPlant
Acacia oshanesiiPlant
Acacia oswaldiiPlant
Acacia parramattensisPlant
Acacia pycnanthaPlant
Acacia retinodesPlant
Acacia rigensPlant
Acacia silvestrisPlant
Acacia terminalisPlant
Acacia trachyphloiaPlant
Acacia vernicifluaPlant
Acacia vestitaPlant
Adenocarpus decorticansPlant
Adenocarpus foliolosusPlant
Allium sativumFooDB
Aloe veraPlant
Amphicarpaea bracteataPlant
Anacardium occidentaleFooDB
Anaxagorea luzonensis A.GRAYPlant
Andira inermisPlant
Apios americanaPlant
Arabidopsis thalianaPlant
Arachis hypogaeaFooDB
Asparagus officinalisFooDB
Baptisia albaPlant
Baptisia australisPlant
Baptisia bracteataPlant
Baptisia calycosaPlant
Baptisia cinereaPlant
Baptisia lanceolataPlant
Baptisia leconteiPlant
Baptisia megacarpaPlant
Baptisia nuttallianaPlant
Baptisia perfoliataPlant
Baptisia tinctoriaPlant
Bos taurusFooDB
Bowdichia nitidaPlant
Brassica oleraceaPlant
Brassica oleracea var. italicaFooDB
Bupleurum scorzonerifoliumPlant
Cajanus cajanFooDB
Cajanus scarabaeoidesPlant
Calicotome spinosaPlant
Calicotome villosaPlant
Calopogonium caeruleumPlant
Camptosema rubicundumPlant
Canavalia eurycarpaPlant
Canavalia gladiataPlant
Castanea sativaFooDB
Cicer arietinumFooDB
Citrus paradisiFooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Clitoria falcataPlant
Clitoria ternateaPlant
Cocos nuciferaFooDB
Coffea arabica L.FooDB
Coffea canephoraFooDB
CorylusFooDB
Crocus sativusPlant
Crotalaria junceaPlant
Cudrania cochinchinensis var. gerontogeaPlant
Cullen corylifoliumPlant
Cytisus albusPlant
Cytisus baeticusPlant
Cytisus commutatusPlant
Cytisus fontanesiiPlant
Cytisus monspessulanus L.Plant
Cytisus proliferusPlant
Cytisus ratisbonensisPlant
Cytisus scopariusPlant
Cytisus striatusPlant
Dalbergia odoriferaPlant
Desmodium gangeticumPlant
Desmodium uncinatumPlant
Dipogon lignosusPlant
Dunbaria villosaPlant
Echinosophora koreensisPlant
Echinospartum horridumPlant
Erinacea anthyllisPlant
Eriosema glomeratumPlant
Eriosema nutansPlant
Eriosema psoraleoidesPlant
Erycibe expansaPlant
Erythrina burttiiPlant
Erythrina latissimaPlant
Erythrina variegataPlant
Erythroxylum uleiPlant
Euchresta formosanaPlant
Fagelia bituminosa-
Feijoa sellowianaPlant
Ficus cordataPlant
Ficus nymphaeifoliaPlant
Ficus septicaPlant
Flemingia macrophyllaPlant
Flemingia philippinensisPlant
Flemingia strictaPlant
Flemingia strobiliferaPlant
Galactia jussiaeanaPlant
Genista acanthocladaPlant
Genista albidaPlant
Genista anglicaPlant
Genista canariensisPlant
Genista cupaniiPlant
Genista depressaPlant
Genista ephedroidesPlant
Genista hispanicaPlant
Genista hystrixPlant
Genista linifoliaPlant
Genista lobeliiPlant
Genista microphyllaPlant
Genista morisiiPlant
Genista obtusirameaPlant
Genista pulchellaPlant
Genista radiataPlant
Genista sagittalisPlant
Genista salzmanniiPlant
Genista scorpiusPlant
Genista sericeaPlant
Genista sessilifoliaPlant
Genista spartioidesPlant
Genista stenopetalaPlant
Genista subcapitataPlant
Genista tinctoriaPlant
Genista triacanthosPlant
Genista tridensPlant
Genista tridentataPlant
Genista ulicinaPlant
Glycine canescensPlant
Glycine clandestinaPlant
Glycine falcataPlant
Glycine latifoliaPlant
Glycine maxFooDB
Glycine tabacinaPlant
Glycine tomentellaPlant
Glycyrrhiza glabraPlant
Glycyrrhiza inflataPlant
Glycyrrhiza uralensisPlant
Halotydeus destructor-
Hardenbergia violaceaPlant
Helianthus annuus L.FooDB
Homo sapiens (Urine)Animalia
Hordeum vulgareFooDB
Hypericum scabrumPlant
Ipomoea batatasFooDB
Juglans regiaFooDB
Kennedia coccineaPlant
Kennedia nigricansPlant
Kennedia procurrensPlant
Kennedia rubicundaPlant
Lablab purpureusFooDB
Laburnum anagyroidesPlant
Lens culinarisFooDB
Lespedeza cyrtobotryaPlant
Lespedeza junceaPlant
Linum usitatissimumFooDB
Lupinus albusFooDB
Lupinus arboreusPlant
Lupinus arcticusPlant
Lupinus elegansPlant
Lupinus luteusPlant
Lupinus mutabilisPlant
Lupinus nanusPlant
Lupinus pilosusPlant
Lupinus sericeusPlant
Lupinus subcarnosusPlant
Lupinus texensisPlant
Maackia amurensisPlant
Maclura cochinchinensisPlant
Macroptilium bracteatumPlant
Macroptilium lathyroidesPlant
Macroptilium martiiPlant
Medicago arabicaPlant
Medicago sativaFooDB
Medicago truncatulaPlant
Millettia dielsianaPlant
Moringa oleiferaPlant
Moringa peregrinaPlant
Moringa stenopetalaPlant
Mucuna pruriensPlant
Neonotonia wightiiPlant
Neorautanenia amboensisPlant
Olea europaeaFooDB
Ononis spinosaPlant
Ormosia monospermaPlant
Oryza sativaFooDB
Otholobium bolusiiPlant
Otholobium bracteolatumPlant
Otholobium candicansPlant
Otholobium hirtumPlant
Otholobium spicatumPlant
Otholobium striatumPlant
Otholobium uncinatumPlant
Otholobium wilmsiiPlant
Passiflora edulisFooDB
Pericopsis laxifloraPlant
Phaseolus coccineusFooDB
Phaseolus lunatusFooDB
Phaseolus vulgarisFooDB
Phoenix dactyliferaFooDB
Piptanthus nepalensisPlant
Pistacia veraFooDB
Pisum sativumFooDB
Prunus armeniacaFooDB
Prunus aviumFooDB
Prunus avium L.FooDB
Prunus cerasusFooDB
Prunus domesticaFooDB
Prunus dulcisFooDB
Prunus spp.Plant
Pseudeminia comosaPlant
Pseudoeriosema borianiiPlant
Pseudovigna argenteaPlant
Psoralea aculeataPlant
Psoralea arboreaPlant
Psoralea axillarisPlant
Psoralea effusaPlant
Psoralea fascicularisPlant
Psoralea laxaPlant
Psoralea oligophyllaPlant
Psoralea repensPlant
Pterocarpus angolensisPlant
Pterocarpus marsupiumPlant
Pueraria candollei var. mirificaPlant
Pueraria lobataPlant
Pueraria mirificaPlant
Pueraria montana var. lobataPlant
Pueraria PhaseoloidesPlant
Pueraria tuberosaPlant
Punica granatumPlant
Retama monospermaPlant
Retama raetamPlant
Rhynchosia caribaeaPlant
Rhynchosia densifloraPlant
Rhynchosia hirsutaPlant
Rhynchosia phaseoloidesPlant
Rhynchosia pyramidalisPlant
Ribes nigrumFooDB
Sarcolobus globosus-
Securidaca inappendiculataPlant
Slackia isoflavoniconvertens-
Solanum tuberosumFooDB
Solori scandensPlant
Sophora secundifloraPlant
Sophora subprostrataPlant
Stemphilium sp. No. 644-
Strongylodon macrobotrysPlant
Styphnolobium japonicumPlant
Taxus fuanaPlant
Taxus wallichiana var. yunnanensisPlant
Tephrosia toxicariaPlant
Teyleria koordersiiPlant
Thermopsis alternifloraPlant
Thermopsis macrophyllaPlant
Thermopsis mollisPlant
Thermopsis rhombifoliaPlant
Thermopsis villosaPlant
ThunnusFooDB
Thunnus alalungaFooDB
Trifolium campestrePlant
Trifolium globosumPlant
Trifolium pannonicumPlant
Trifolium pratensePlant
Trifolium repensPlant
Trifolium riograndensePlant
Trifolium spp.Plant
Trigonella foenum-graecumFooDB
TriticumFooDB
Ulex boiviniiPlant
Ulex europaeusPlant
Ulex galliiPlant
Ulex genistoidesPlant
Ulex micranthusPlant
Ulex minorPlant
Ulex parviflorusPlant
Vaccinium macrocarponFooDB
Vandasina retusaPlant
Vicia fabaFooDB
Vigna angularisFooDB
Vigna mungoFooDB
Vigna radiataFooDB
Vigna subterraneaPlant
Vigna unguiculata ssp. unguiculataFooDB
Vitis vinifera L.FooDB
Wisteria brachybotrysPlant
Zea mays L.FooDB
Zingiber officinalePlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassIsoflav-2-enes
Direct ParentIsoflavones
Alternative Parents
Substituents
  • Hydroxyisoflavonoid
  • Isoflavone
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Vinylogous acid
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point301.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP3.04ALOGPS
logP3.08ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)6.55ChemAxon
pKa (Strongest Basic)-5.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity71.68 m³·mol⁻¹ChemAxon
Polarizability26.59 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0003217
DrugBank IDDB01645
Phenol Explorer Compound ID396
FoodDB IDFDB011828
KNApSAcK IDC00002526
Chemspider ID4444448
KEGG Compound IDC06563
BioCyc IDCPD-3141
BiGG IDNot Available
Wikipedia LinkGenistein
METLIN ID3398
PubChem Compound5280961
PDB IDNot Available
ChEBI ID28088
Good Scents IDrw1504491
References
General References
  1. Wisniewski AB, Klein SL, Lakshmanan Y, Gearhart JP: Exposure to genistein during gestation and lactation demasculinizes the reproductive system in rats. J Urol. 2003 Apr;169(4):1582-6. [PubMed:12629420 ]
  2. Ohno S, Nakajima Y, Inoue K, Nakazawa H, Nakajin S: Genistein administration decreases serum corticosterone and testosterone levels in rats. Life Sci. 2003 Dec 26;74(6):733-42. [PubMed:14654166 ]
  3. Kim S, Shin HJ, Kim SY, Kim JH, Lee YS, Kim DH, Lee MO: Genistein enhances expression of genes involved in fatty acid catabolism through activation of PPARalpha. Mol Cell Endocrinol. 2004 May 31;220(1-2):51-8. [PubMed:15196699 ]
  4. de Pascual-Teresa S, Hallund J, Talbot D, Schroot J, Williams CM, Bugel S, Cassidy A: Absorption of isoflavones in humans: effects of food matrix and processing. J Nutr Biochem. 2006 Apr;17(4):257-64. [PubMed:16109484 ]
  5. Huang X, Chen S, Xu L, Liu Y, Deb DK, Platanias LC, Bergan RC: Genistein inhibits p38 map kinase activation, matrix metalloproteinase type 2, and cell invasion in human prostate epithelial cells. Cancer Res. 2005 Apr 15;65(8):3470-8. [PubMed:15833883 ]
  6. Ronis MJ, Little JM, Barone GW, Chen G, Radominska-Pandya A, Badger TM: Sulfation of the isoflavones genistein and daidzein in human and rat liver and gastrointestinal tract. J Med Food. 2006 Fall;9(3):348-55. [PubMed:17004897 ]
  7. Fotsis T, Pepper MS, Aktas E, Breit S, Rasku S, Adlercreutz H, Wahala K, Montesano R, Schweigerer L: Flavonoids, dietary-derived inhibitors of cell proliferation and in vitro angiogenesis. Cancer Res. 1997 Jul 15;57(14):2916-21. [PubMed:9230201 ]
  8. Casagrande F, Darbon JM: p21CIP1 is dispensable for the G2 arrest caused by genistein in human melanoma cells. Exp Cell Res. 2000 Jul 10;258(1):101-8. [PubMed:10912792 ]
  9. Li Y, Ahmed F, Ali S, Philip PA, Kucuk O, Sarkar FH: Inactivation of nuclear factor kappaB by soy isoflavone genistein contributes to increased apoptosis induced by chemotherapeutic agents in human cancer cells. Cancer Res. 2005 Aug 1;65(15):6934-42. [PubMed:16061678 ]
  10. D'Souza N, Skonberg DI, Camire ME, Guthrie KE, Malison J, Lima L: Influence of dietary genistein levels on tissue genistein deposition and on the physical, chemical, and sensory quality of rainbow trout, Oncorhynchus mykiss. J Agric Food Chem. 2005 May 4;53(9):3631-6. [PubMed:15853412 ]
  11. Sonee M, Sum T, Wang C, Mukherjee SK: The soy isoflavone, genistein, protects human cortical neuronal cells from oxidative stress. Neurotoxicology. 2004 Sep;25(5):885-91. [PubMed:15288519 ]
  12. Li M, Zhang Z, Hill DL, Chen X, Wang H, Zhang R: Genistein, a dietary isoflavone, down-regulates the MDM2 oncogene at both transcriptional and posttranslational levels. Cancer Res. 2005 Sep 15;65(18):8200-8. [PubMed:16166295 ]
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