1.0 2016-09-30 22:54:16 UTC 2020-06-04 20:47:06 UTC BMDB0002338 BMDB02338 Biochanin A Biochanin a, also known as olmelin or pratensol, belongs to the class of organic compounds known as 4'-o-methylisoflavones. These are isoflavones with methoxy groups attached to the C4' atom of the isoflavone backbone. Thus, biochanin a is considered to be a flavonoid lipid molecule. Biochanin a is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Biochanin a is a potentially toxic compound. 4'-Methylgenistein 5,7-Dihydroxy-3-(4-methoxyphenyl)-4H-1-benzopyran-4-one 5,7-Dihydroxy-3-p-methoxyphenyl-4H-chromen-4-one 5,7-Dihydroxy-4'-methoxyisoflavone Olmelin Pratensol Biochanin a, 14C-labeled Genistein 4-methyl ether 5,7-Dihydroxy-4'-methoxy-isoflavone 5,7-Dihydroxy-4'-methoxy-isoflavone (8ci) Biochanin Biochanine a C16H12O5 284.267 284.068473486 5,7-dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one biochanin 491-80-5 COC1=CC=C(C=C1)C1=COC2=CC(O)=CC(O)=C2C1=O InChI=1S/C16H12O5/c1-20-11-4-2-9(3-5-11)12-8-21-14-7-10(17)6-13(18)15(14)16(12)19/h2-8,17-18H,1H3 WUADCCWRTIWANL-UHFFFAOYSA-N belongs to the class of organic compounds known as 4'-o-methylisoflavones. These are isoflavones with methoxy groups attached to the C4' atom of the isoflavone backbone. Organic compounds Phenylpropanoids and polyketides Isoflavonoids O-methylated isoflavonoids 4'-O-methylisoflavones 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Anisoles Chromones Heteroaromatic compounds Hydrocarbon derivatives Hydroxyisoflavonoids Isoflavones Methoxybenzenes Organic oxides Oxacyclic compounds Phenoxy compounds Pyranones and derivatives Vinylogous acids 1-benzopyran 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 4p-o-methylisoflavone Alkyl aryl ether Anisole Aromatic heteropolycyclic compound Benzenoid Benzopyran Chromone Ether Heteroaromatic compound Hydrocarbon derivative Hydroxyisoflavonoid Isoflavone Methoxybenzene Monocyclic benzene moiety Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Phenol ether Phenoxy compound Pyran Pyranone Vinylogous acid Aromatic heteropolycyclic compounds 7-hydroxyisoflavones Isoflavonoids Isoflavonoids isoflavones methoxyisoflavone Solid logp 3.44 ALOGPS logs -3.69 ALOGPS logp 3.22 ChemAxon pka_strongest_acidic 6.55 ChemAxon pka_strongest_basic -4.7 ChemAxon iupac 5,7-dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one ChemAxon average_mass 284.267 ChemAxon mono_mass 284.068473486 ChemAxon smiles COC1=CC=C(C=C1)C1=COC2=CC(O)=CC(O)=C2C1=O ChemAxon formula C16H12O5 ChemAxon inchi InChI=1S/C16H12O5/c1-20-11-4-2-9(3-5-11)12-8-21-14-7-10(17)6-13(18)15(14)16(12)19/h2-8,17-18H,1H3 ChemAxon inchikey WUADCCWRTIWANL-UHFFFAOYSA-N ChemAxon polar_surface_area 75.99 ChemAxon refractivity 76.17 ChemAxon polarizability 28.68 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 5 ChemAxon donor_count 2 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::CMs 2196 Specdb::CMs 5768 Specdb::CMs 31408 Specdb::CMs 32045 Specdb::CMs 38374 Specdb::CMs 152073 Specdb::MsMs 19874 Specdb::MsMs 19875 Specdb::MsMs 19876 Specdb::MsMs 21179 Specdb::MsMs 21180 Specdb::MsMs 21181 Specdb::MsMs 21425 Specdb::MsMs 21426 Specdb::MsMs 21427 Specdb::MsMs 22730 Specdb::MsMs 22731 Specdb::MsMs 22732 Specdb::MsMs 285663 Specdb::MsMs 285664 Specdb::MsMs 285665 Specdb::MsMs 285666 Specdb::MsMs 285667 Specdb::MsMs 373634 Specdb::MsMs 373635 Specdb::MsMs 373636 Specdb::MsMs 373637 Specdb::MsMs 373638 Specdb::MsMs 374078 Specdb::MsMs 374079 Specdb::MsMs 374080 Milk 5.558 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 7.493 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 1.161 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 1.442 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 Milk 0.00457 +/- 0.000246 uM Raw milk. Nielsen TS, Norgaard JV, Purup S, Frette XC, Bonefeld-Jorgensen EC: Estrogenic activity of bovine milk high or low in equol using immature mouse uterotrophic responses and an estrogen receptor transactivation assay. Cancer Epidemiol. 2009 Jul;33(1):61-8. doi: 10.1016/j.canep.2009.04.003. Epub 2009 May 31. 19679050 C00814 4444068 FDB012223 5280373 17574 C00002510 397 Biochanin_A BIOCHANIN-A Gakhokidze, A. M. Synthesis of olmelin. Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation) (1950), 23 559-60. 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 Nielsen TS, Norgaard JV, Purup S, Frette XC, Bonefeld-Jorgensen EC: Estrogenic activity of bovine milk high or low in equol using immature mouse uterotrophic responses and an estrogen receptor transactivation assay. Cancer Epidemiol. 2009 Jul;33(1):61-8. doi: 10.1016/j.canep.2009.04.003. Epub 2009 May 31. 19679050