1.0 2016-09-30 23:15:07 UTC 2020-06-04 20:44:37 UTC BMDB0005056 BMDB05056 Enterodiol Enterodiol, also known as 2,3-BHBBD or arbo 9, belongs to the class of organic compounds known as dibenzylbutanediol lignans. These are lignan compounds containing a 2,3-dibenzylbutane-1,4-diol moiety. Enterodiol is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Enterodiol is a potentially toxic compound. (-)-Enterodiol (2R,3R)-2,3-Bis[(3-hydroxyphenyl)methyl]-1,4-butanediol Arbo 9 [R-(R*,r*)]-2,3-bis[(3-hydroxyphenyl)methyl]-1,4-butanediol 2,3-Bis(3'-hydroxybenzyl)butane-1,4-diol 2,3-BHBBD 2,3-Bis(3-hydroxybenzyl)butane-1,4-diol Enterodiol C18H22O4 302.3649 302.151809192 (2R,3R)-2,3-bis[(3-hydroxyphenyl)methyl]butane-1,4-diol (-)-enterodiol 80226-00-2 OC[C@H](CC1=CC(O)=CC=C1)[C@H](CO)CC1=CC(O)=CC=C1 InChI=1S/C18H22O4/c19-11-15(7-13-3-1-5-17(21)9-13)16(12-20)8-14-4-2-6-18(22)10-14/h1-6,9-10,15-16,19-22H,7-8,11-12H2/t15-,16-/m0/s1 DWONJCNDULPHLV-HOTGVXAUSA-N belongs to the class of organic compounds known as dibenzylbutanediol lignans. These are lignan compounds containing a 2,3-dibenzylbutane-1,4-diol moiety. Organic compounds Lignans, neolignans and related compounds Dibenzylbutane lignans Dibenzylbutanediol lignans Dibenzylbutanediol lignans 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Benzene and substituted derivatives Hydrocarbon derivatives Primary alcohols 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Alcohol Aromatic homomonocyclic compound Benzenoid Dibenzylbutanediol Hydrocarbon derivative Monocyclic benzene moiety Organic oxygen compound Organooxygen compound Phenol Primary alcohol Aromatic homomonocyclic compounds lignan Solid logp 1.91 ALOGPS logs -4.09 ALOGPS logp 2.65 ChemAxon pka_strongest_acidic 9.79 ChemAxon pka_strongest_basic -2.6 ChemAxon iupac (2R,3R)-2,3-bis[(3-hydroxyphenyl)methyl]butane-1,4-diol ChemAxon average_mass 302.3649 ChemAxon mono_mass 302.151809192 ChemAxon smiles OC[C@H](CC1=CC(O)=CC=C1)[C@H](CO)CC1=CC(O)=CC=C1 ChemAxon formula C18H22O4 ChemAxon inchi InChI=1S/C18H22O4/c19-11-15(7-13-3-1-5-17(21)9-13)16(12-20)8-14-4-2-6-18(22)10-14/h1-6,9-10,15-16,19-22H,7-8,11-12H2/t15-,16-/m0/s1 ChemAxon inchikey DWONJCNDULPHLV-HOTGVXAUSA-N ChemAxon polar_surface_area 80.92 ChemAxon refractivity 86.36 ChemAxon polarizability 32.76 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 4 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Specdb::CMs 5539 Specdb::CMs 38848 Specdb::CMs 159548 Specdb::MsMs 47994 Specdb::MsMs 47995 Specdb::MsMs 47996 Specdb::MsMs 144861 Specdb::MsMs 144862 Specdb::MsMs 144863 Specdb::MsMs 2226610 Specdb::MsMs 2228099 Specdb::MsMs 2229036 Specdb::MsMs 2230430 Specdb::MsMs 2231469 Specdb::MsMs 2232715 Specdb::MsMs 2233843 Specdb::MsMs 2235113 Specdb::MsMs 2239897 Specdb::MsMs 2248222 Specdb::MsMs 2250173 Specdb::MsMs 2258684 Specdb::MsMs 2259870 Specdb::MsMs 2816278 Specdb::MsMs 2816279 Specdb::MsMs 2816280 Specdb::MsMs 2892491 Specdb::MsMs 2892492 Specdb::MsMs 2892493 Milk 0.00860 - 0.0132 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 0.232 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 0.298 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 0.43 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 0.496 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 102992 C18166 544560 115089 FDB021828 C00000702 Enterodiol Mahalanabis, K. K.; Mumtax, M.; Snieckuz, V. Dimetalated tertiary succinamides. Synthesis of several classes of lignans including the mammalian urinary lignans enterolactone and enterodiol. Tetrahedron Letters (1982), 23(39), 3975-8. 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