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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 NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)Wishart Lab2021-06-20View Spectrum
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
2D NMR[1H, 13C] 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
  • Animalia
  • Plantae
  • 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
    External Links
    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 IDNot Available
    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 ]
    13. Si H, Liu D: Phytochemical genistein in the regulation of vascular function: new insights. Curr Med Chem. 2007;14(24):2581-9. [PubMed:17979711 ]
    14. 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: Effects of the phytoestrogen genistein on cardiovascular risk factors in postmenopausal women. Menopause. 2005 Mar;12(2):186-92. [PubMed:15772566 ]