1.0 2016-09-30 23:20:09 UTC 2020-06-04 20:50:53 UTC BMDB0006101 BMDB06101 Enterolactone Enterolactone, also known as HPMF or 2,3-BHBB, belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety. Enterolactone is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Enterolactone is a potentially toxic compound. HPMF trans-2,3-Bis(3-hydroxybenzyl)-gamma-butyrolactone 2,3-BHBB 2,3-Bis(3'-hydroxybenzyl)butyrolactone, (trans)-(+-)-isomer 2,3-Bis(3'-hydroxybenzyl)butyrolactone BHMDF 3,4-Bis((3-hydroxyphenyl)methyl)dihydro-2-(3H)-furanone 2,3-Bis(3'-hydroxybenzyl)butyrolactone, (trans)-isomer (+/-)-enterolactone dihydro-3,4-Bis((3-hydroxyphenyl)methyl)-2(3H)-furanone Enterolactone C18H18O4 298.3331 298.120509064 3,4-bis[(3-hydroxyphenyl)methyl]oxolan-2-one HPMF OC1=CC=CC(CC2COC(=O)C2CC2=CC(O)=CC=C2)=C1 InChI=1S/C18H18O4/c19-15-5-1-3-12(8-15)7-14-11-22-18(21)17(14)10-13-4-2-6-16(20)9-13/h1-6,8-9,14,17,19-20H,7,10-11H2 HVDGDHBAMCBBLR-UHFFFAOYSA-N belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety. Organic compounds Lignans, neolignans and related compounds Furanoid lignans Tetrahydrofuran lignans Dibenzylbutyrolactone lignans 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Benzene and substituted derivatives Carbonyl compounds Carboxylic acid esters Gamma butyrolactones Hydrocarbon derivatives Lignan lactones Monocarboxylic acids and derivatives Organic oxides Oxacyclic compounds Tetrahydrofurans 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Aromatic heteromonocyclic compound Benzenoid Carbonyl group Carboxylic acid derivative Carboxylic acid ester Dibenzylbutyrolactone Gamma butyrolactone Hydrocarbon derivative Lactone Lignan lactone Monocarboxylic acid or derivatives Monocyclic benzene moiety Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Phenol Tetrahydrofuran Aromatic heteromonocyclic compounds Solid logp 3.20 ALOGPS logs -4.12 ALOGPS logp 3.61 ChemAxon pka_strongest_acidic 9.16 ChemAxon pka_strongest_basic -6 ChemAxon iupac 3,4-bis[(3-hydroxyphenyl)methyl]oxolan-2-one ChemAxon average_mass 298.3331 ChemAxon mono_mass 298.120509064 ChemAxon smiles OC1=CC=CC(CC2COC(=O)C2CC2=CC(O)=CC=C2)=C1 ChemAxon formula C18H18O4 ChemAxon inchi InChI=1S/C18H18O4/c19-15-5-1-3-12(8-15)7-14-11-22-18(21)17(14)10-13-4-2-6-16(20)9-13/h1-6,8-9,14,17,19-20H,7,10-11H2 ChemAxon inchikey HVDGDHBAMCBBLR-UHFFFAOYSA-N ChemAxon polar_surface_area 66.76 ChemAxon refractivity 82.71 ChemAxon polarizability 30.77 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 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 22488 Specdb::CMs 38957 Specdb::MsMs 82281 Specdb::MsMs 82282 Specdb::MsMs 82283 Specdb::MsMs 143598 Specdb::MsMs 143599 Specdb::MsMs 143600 Milk 0.0369 - 0.0825 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 90.503 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 72.402 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 130.056 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 90.503 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 123917 Enterolactone 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