1.0 2016-09-30 23:03:08 UTC 2020-06-04 20:47:26 UTC BMDB0003217 BMDB03217 Genistein Genistein, also known as prunetol or sophoricol, 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. Thus, genistein is considered to be a flavonoid lipid molecule. Genistein exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Genistein is a potentially toxic compound. 4',5,7-Trihydroxyisoflavone 5,7,4'-Trihydroxyisoflavone 5,7-Dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one Prunetol Sophoricol 4',5, 7-Trihydroxyisoflavone 4',5,7-Trihydroxy-isoflavone 4,5,7-Trihydroxy iso-flavone Genistein 85% HPLC Genisteol Genisterin Genestein C15H10O5 270.24 270.052823422 5,7-dihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one genistein 446-72-0 OC1=CC=C(C=C1)C1=COC2=CC(O)=CC(O)=C2C1=O 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 TZBJGXHYKVUXJN-UHFFFAOYSA-N 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. Organic compounds Phenylpropanoids and polyketides Isoflavonoids Isoflav-2-enes Isoflavones 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Benzene and substituted derivatives Chromones Heteroaromatic compounds Hydrocarbon derivatives Hydroxyisoflavonoids Organic oxides Organooxygen compounds Oxacyclic compounds Pyranones and derivatives Vinylogous acids 1-benzopyran 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Aromatic heteropolycyclic compound Benzenoid Benzopyran Chromone Heteroaromatic compound Hydrocarbon derivative Hydroxyisoflavonoid Isoflavone Monocyclic benzene moiety Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Phenol Pyran Pyranone Vinylogous acid Aromatic heteropolycyclic compounds 7-hydroxyisoflavones Isoflavonoids Isoflavonoids isoflavones Solid melting_point 301.5 °C logp 3.04 ALOGPS logs -3.34 ALOGPS logp 3.08 ChemAxon pka_strongest_acidic 6.55 ChemAxon pka_strongest_basic -5.3 ChemAxon iupac 5,7-dihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one ChemAxon average_mass 270.24 ChemAxon mono_mass 270.052823422 ChemAxon smiles OC1=CC=C(C=C1)C1=COC2=CC(O)=CC(O)=C2C1=O ChemAxon formula C15H10O5 ChemAxon 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 ChemAxon inchikey TZBJGXHYKVUXJN-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 -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Specdb::NmrTwoD 1871 Specdb::NmrOneD 1936 Specdb::NmrOneD 166384 Specdb::NmrOneD 166531 Specdb::CMs 872 Specdb::CMs 5885 Specdb::CMs 30547 Specdb::CMs 38544 Specdb::CMs 132739 Specdb::CMs 140473 Specdb::MsMs 6381 Specdb::MsMs 6382 Specdb::MsMs 6383 Specdb::MsMs 6384 Specdb::MsMs 6385 Specdb::MsMs 6386 Specdb::MsMs 6387 Specdb::MsMs 6389 Specdb::MsMs 6390 Specdb::MsMs 6391 Specdb::MsMs 6392 Specdb::MsMs 6393 Specdb::MsMs 6394 Specdb::MsMs 240994 Specdb::MsMs 240995 Specdb::MsMs 240996 Specdb::MsMs 243049 Specdb::MsMs 243050 Specdb::MsMs 243051 Specdb::MsMs 285617 Specdb::MsMs 285618 Specdb::MsMs 285619 Specdb::MsMs 285620 Specdb::MsMs 373654 Specdb::MsMs 373655 Adipose Tissue Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Adrenal Gland Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Epidermis Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Fibroblasts Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Intestine Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Liver Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Milk 0.000370 - 0.00740 uM Raw milk Antignac JP, Cariou R, Le Bizec B, Cravedi JP, Andre F: Identification of phytoestrogens in bovine milk using liquid chromatography/electrospray tandem mass spectrometry. Rapid Commun Mass Spectrom. 2003;17(12):1256-64. doi: 10.1002/rcm.1052. 12811748 Milk 0.0148 - 0.107 uM Raw milk. Range in australian herds King RA, Mano MM, Head RJ: Assessment of isoflavonoid concentrations in Australian bovine milk samples. J Dairy Res. 1998 Aug;65(3):479-89. 9718497 Milk 9.51 uM Raw milk. Diet: red clover, concentrate supplement Steinshamn H, Purup S, Thuen E, Hansen-Moller J: Effects of clover-grass silages and concentrate supplementation on the content of phytoestrogens in dairy cow milk. J Dairy Sci. 2008 Jul;91(7):2715-25. doi: 10.3168/jds.2007-0857. 18565930 Milk 11.175 uM Raw milk. Diet: red clover, no concentrate supplement Steinshamn H, Purup S, Thuen E, Hansen-Moller J: Effects of clover-grass silages and concentrate supplementation on the content of phytoestrogens in dairy cow milk. J Dairy Sci. 2008 Jul;91(7):2715-25. doi: 10.3168/jds.2007-0857. 18565930 Milk 7.438 uM Raw milk. Diet: white clover, concentrate supplement Steinshamn H, Purup S, Thuen E, Hansen-Moller J: Effects of clover-grass silages and concentrate supplementation on the content of phytoestrogens in dairy cow milk. J Dairy Sci. 2008 Jul;91(7):2715-25. doi: 10.3168/jds.2007-0857. 18565930 Milk 7.0679 uM Raw milk. Diet:white clover, no concentrate supplement Steinshamn H, Purup S, Thuen E, Hansen-Moller J: Effects of clover-grass silages and concentrate supplementation on the content of phytoestrogens in dairy cow milk. J Dairy Sci. 2008 Jul;91(7):2715-25. doi: 10.3168/jds.2007-0857. 18565930 Neuron Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Placenta Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Platelet Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Prostate Tissue Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Skeletal Muscle Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Testis Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 C06563 FDB011828 DB01645 4444448 5280961 28088 396 C00002526 Genistein 3398 CPD-3141 Baker, Wilson; Robinson, Robert. Synthetical experiments in the isoflavone group. IV. Synthesis of 2-methylirigenol. Journal of the Chemical Society (1929), Volume Date 1928, 152-61. King RA, Mano MM, Head RJ: Assessment of isoflavonoid concentrations in Australian bovine milk samples. J Dairy Res. 1998 Aug;65(3):479-89. 9718497 Antignac JP, Cariou R, Le Bizec B, Cravedi JP, Andre F: Identification of phytoestrogens in bovine milk using liquid chromatography/electrospray tandem mass spectrometry. Rapid Commun Mass Spectrom. 2003;17(12):1256-64. doi: 10.1002/rcm.1052. 12811748 Steinshamn H, Purup S, Thuen E, Hansen-Moller J: Effects of clover-grass silages and concentrate supplementation on the content of phytoestrogens in dairy cow milk. J Dairy Sci. 2008 Jul;91(7):2715-25. doi: 10.3168/jds.2007-0857. 18565930