1.0 2016-09-30 23:18:48 UTC 2020-06-04 20:48:05 UTC BMDB0005808 BMDB05808 Formononetin Formononetin, also known as biochanin b, 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, formononetin is considered to be a flavonoid lipid molecule. Formononetin exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. 4'-O-Methyldaidzein 7-Hydroxy-3-(4-methoxyphenyl)-4-benzopyrone 7-Hydroxy-3-(4-methoxyphenyl)-4H-benzopyran-4-one 7-Hydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one 7-Hydroxy-4'-methoxyisoflavone Biochanin b Formononetol Formononetin, 4-(14)C-labeled 7-Hydroxy-3-(4-methoxyphenyl)-4H-benzopyran-4-one(9ci) 7-Hydroxy-4'-methoxy-isoflavone 7-Hydroxy-4'-methoxy-isoflavone (8ci) C16H12O4 268.268 268.073558866 7-hydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one formononetin 485-72-3 COC1=CC=C(C=C1)C1=COC2=C(C=CC(O)=C2)C1=O InChI=1S/C16H12O4/c1-19-12-5-2-10(3-6-12)14-9-20-15-8-11(17)4-7-13(15)16(14)18/h2-9,17H,1H3 HKQYGTCOTHHOMP-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 Alkyl aryl ethers Anisoles Chromones Heteroaromatic compounds Hydrocarbon derivatives Hydroxyisoflavonoids Isoflavones Methoxybenzenes Organic oxides Oxacyclic compounds Phenoxy compounds Pyranones and derivatives 1-benzopyran 1-hydroxy-2-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 Aromatic heteropolycyclic compounds 7-hydroxyisoflavones Isoflavonoids Isoflavonoids a 4'-methoxyisoflavone isoflavones methoxyisoflavone Solid melting_point 256 - 258 °C logp 3.56 ALOGPS logs -3.82 ALOGPS logp 2.88 ChemAxon pka_strongest_acidic 6.48 ChemAxon pka_strongest_basic -4.7 ChemAxon iupac 7-hydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one ChemAxon average_mass 268.268 ChemAxon mono_mass 268.073558866 ChemAxon smiles COC1=CC=C(C=C1)C1=COC2=C(C=CC(O)=C2)C1=O ChemAxon formula C16H12O4 ChemAxon inchi InChI=1S/C16H12O4/c1-19-12-5-2-10(3-6-12)14-9-20-15-8-11(17)4-7-13(15)16(14)18/h2-9,17H,1H3 ChemAxon inchikey HKQYGTCOTHHOMP-UHFFFAOYSA-N ChemAxon polar_surface_area 55.76 ChemAxon refractivity 74.18 ChemAxon polarizability 27.86 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 4 ChemAxon donor_count 1 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 5860 Specdb::CMs 32282 Specdb::CMs 38899 Specdb::CMs 99887 Specdb::CMs 157438 Specdb::MsMs 21062 Specdb::MsMs 21063 Specdb::MsMs 21064 Specdb::MsMs 22613 Specdb::MsMs 22614 Specdb::MsMs 22615 Specdb::MsMs 285679 Specdb::MsMs 285680 Specdb::MsMs 285681 Specdb::MsMs 285682 Specdb::MsMs 285683 Specdb::MsMs 285684 Specdb::MsMs 373787 Specdb::MsMs 373788 Specdb::MsMs 373789 Specdb::MsMs 373790 Specdb::MsMs 373791 Specdb::MsMs 373792 Specdb::MsMs 374081 Specdb::MsMs 374082 Specdb::MsMs 374889 Specdb::MsMs 439185 Specdb::MsMs 439404 Specdb::MsMs 439406 Specdb::MsMs 439408 Milk 0.0399 - 0.0760 uM Raw milk, range from both high equol and low equol milk - high = diet of mainly red clover 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 Milk 0.0168 uM Pasteurized organic milk Hoikkala A, Mustonen E, Saastamoinen I, Jokela T, Taponen J, Saloniemi H, Wahala K: High levels of equol in organic skimmed Finnish cow milk. Mol Nutr Food Res. 2007 Jul;51(7):782-6. doi: 10.1002/mnfr.200600222. 17576638 Milk 22.329 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 25.945 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 9.729 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 10.177 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 FDB012219 4444070 C00002525 5280378 C00858 395 18088 FORMONONETIN Formononetin Whalley J L; Bond T J; Botting N P Synthesis of 13C labelled daidzein and formononetin. Bioorganic & medicinal chemistry letters (1998), 8(18), 2569-72. Hoikkala A, Mustonen E, Saastamoinen I, Jokela T, Taponen J, Saloniemi H, Wahala K: High levels of equol in organic skimmed Finnish cow milk. Mol Nutr Food Res. 2007 Jul;51(7):782-6. doi: 10.1002/mnfr.200600222. 17576638 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