1.0 2011-09-21 00:34:44 UTC 2017-10-05 10:34:17 UTC FDB023788 Dihydrogenistein Dihydrogenistein is a metabolite of the soy isoflavone genistin (the glycoside conjugate of genistein) by intestinal bacteria. Isoflavones are one of the three major classes of phytoestrogens; phytoestrogens are a diverse group of plant-derived compounds that structurally and functionally mimic mammalian estrogen. The isoflavone genistin is one of the most prevalent in soy foods. They are biologically inactive; once ingested, they are cleaved by glucosidases to "aglycones", genistein. Epidemiological studies have associated high soy intake with a lowered risk for certain hormone-dependent disease. Many studies reveal that the incidence of prostate cancer and breast cancer is much lower in Asian people in comparison to people from the West and, and the prevailing contribution to this difference has been attributed to the diet. Soy foods and soy-derived products which contain abundant isoflavones are consumed in large quantities by Asian people. In vitro, isoflavone metabolites have dual functions: they can act as an estrogenic agonist or antagonist depending on the estrogen concentration. (PMID: 17499260, 16965913) [HMDB]. Dihydrogenistein is a biomarker for the consumption of soy beans and other soy products. 2,3-dihydro-5,7-Dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one 4',5,7-trihydroxy-Isoflavanone 4',5,7-Trihydroxyisoflavan-4-one 4',5,7-Trihydroxyisoflavanone C15H12O5 272.2528 272.068473494 5,7-dihydroxy-3-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one dihydrogenistein 21554-71-2 OC1=CC=C(C=C1)C1COC2=CC(O)=CC(O)=C2C1=O InChI=1S/C15H12O5/c16-9-3-1-8(2-4-9)11-7-20-13-6-10(17)5-12(18)14(13)15(11)19/h1-6,11,16-18H,7H2 UQGVUYNHDKMLSE-UHFFFAOYSA-N belongs to the class of organic compounds known as isoflavanones. These are polycyclic compounds containing an isoflavan skeleton which bears a ketone at position C4. Isoflavanones Organic compounds Phenylpropanoids and polyketides Isoflavonoids Isoflavans Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Aryl alkyl ketones Benzene and substituted derivatives Chromones Hydrocarbon derivatives Hydroxyisoflavonoids Isoflavanols Organic oxides Oxacyclic compounds Vinylogous acids 1-benzopyran 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Alkyl aryl ether Aromatic heteropolycyclic compound Aryl alkyl ketone Aryl ketone Benzenoid Benzopyran Chromane Chromone Ether Hydrocarbon derivative Hydroxyisoflavonoid Isoflavanol Isoflavanone Ketone Monocyclic benzene moiety Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Phenol Vinylogous acid hydroxyisoflavanone Solid logp 2.45 ALOGPS logs -3.08 ALOGPS solubility 2.28e-01 g/l ALOGPS logp 2.73 ChemAxon pka_strongest_acidic 7.9 ChemAxon pka_strongest_basic -3.9 ChemAxon iupac 5,7-dihydroxy-3-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one ChemAxon average_mass 272.2528 ChemAxon mono_mass 272.068473494 ChemAxon smiles OC1=CC=C(C=C1)C1COC2=CC(O)=CC(O)=C2C1=O ChemAxon formula C15H12O5 ChemAxon inchi InChI=1S/C15H12O5/c16-9-3-1-8(2-4-9)11-7-20-13-6-10(17)5-12(18)14(13)15(11)19/h1-6,11,16-18H,7H2 ChemAxon inchikey UQGVUYNHDKMLSE-UHFFFAOYSA-N ChemAxon polar_surface_area 86.99 ChemAxon refractivity 71.68 ChemAxon polarizability 26.59 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 5796 Specdb::CMs 38919 Specdb::CMs 149279 Specdb::MsMs 10778 Specdb::MsMs 10779 Specdb::MsMs 10780 Specdb::MsMs 17450 Specdb::MsMs 17451 Specdb::MsMs 17452 Specdb::MsMs 2775212 Specdb::MsMs 2775213 Specdb::MsMs 2775214 Specdb::MsMs 2907081 Specdb::MsMs 2907082 Specdb::MsMs 2907083 HMDB05897 #<Reference:0x000055ce3319b890> #<Reference:0x000055ce3319b6d8> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823