1.0 2011-04-11 17:01:52 UTC 2019-11-26 03:20:55 UTC FDB021828 Enterodiol Enterodiol is one of the most important lignan-type phytoestrogens identified in serum, urine, bile and seminal fluids of humans and animals. Phytoestrogens are a diverse group of compounds found in many edible plants that have, as their common denominator, a phenolic group that they share with estrogenic steroids. This phenolic group appears to play an important role in determining the estrogenic agonist/antagonistic properties of these compounds. Phytoestrogens have been categorized according to their chemical structures as isoflavones, lignans and coumestans. Enterodiol is formed by bacteria in the intestinal tract from the plant lignans matairesinol and secoisolariciresinol, which exist in various whole-grain cereals (barley, rye and wheat), seeds, nuts, legumes and vegetables. (PMID: 12270221, J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Sep 25;777(1-2):289-309.) [HMDB]. Enterodiol is a biomarker for the consumption of soy beans and other soy products. (-)-Enterodiol (2R,3R)-2,3-Bis[(3-hydroxyphenyl)methyl]-1,4-butanediol [R-(R*,r*)]-2,3-bis[(3-hydroxyphenyl)methyl]-1,4-butanediol Arbo 9 C18H22O4 302.3649 302.151809192 2,3-bis[(3-hydroxyphenyl)methyl]butane-1,4-diol 2,3-bis[(3-hydroxyphenyl)methyl]butane-1,4-diol 80226-00-2 OCC(CC1=CC(O)=CC=C1)C(CO)CC1=CC=CC(O)=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 DWONJCNDULPHLV-UHFFFAOYSA-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. Dibenzylbutanediol lignans Organic compounds Lignans, neolignans and related compounds Dibenzylbutane lignans Dibenzylbutanediol lignans Aromatic homomonocyclic compounds 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 Solid logp 1.91 ALOGPS logs -4.09 ALOGPS solubility 2.47e-02 g/l ALOGPS logp 2.65 ChemAxon pka_strongest_acidic 9.79 ChemAxon pka_strongest_basic -2.6 ChemAxon iupac 2,3-bis[(3-hydroxyphenyl)methyl]butane-1,4-diol ChemAxon average_mass 302.3649 ChemAxon mono_mass 302.151809192 ChemAxon smiles OCC(CC1=CC(O)=CC=C1)C(CO)CC1=CC=CC(O)=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 ChemAxon inchikey DWONJCNDULPHLV-UHFFFAOYSA-N ChemAxon polar_surface_area 80.92 ChemAxon refractivity 86.36 ChemAxon polarizability 32.34 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 4 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 114926 Specdb::CMs 129120 Specdb::CMs 814829 Specdb::CMs 814830 Specdb::CMs 814831 Specdb::CMs 814832 Specdb::CMs 814833 Specdb::CMs 814834 Specdb::CMs 814835 Specdb::CMs 814836 Specdb::CMs 814837 Specdb::CMs 814838 Specdb::CMs 814839 Specdb::CMs 814840 Specdb::CMs 814841 Specdb::CMs 814842 Specdb::CMs 814843 Specdb::CMs 814844 Specdb::CMs 814845 Specdb::CMs 814846 Specdb::MsMs 2227896 Specdb::MsMs 2229157 Specdb::MsMs 2230317 Specdb::MsMs 2231587 Specdb::MsMs 2232585 Specdb::MsMs 2234039 Specdb::MsMs 2234918 Specdb::MsMs 2252549 Specdb::MsMs 2253919 Specdb::MsMs 2254653 Specdb::MsMs 2258560 Specdb::MsMs 2258787 Specdb::MsMs 2259777 Specdb::MsMs 2260025 Specdb::MsMs 3400663 Specdb::MsMs 3400664 Specdb::MsMs 3400665 Specdb::MsMs 3400666 Specdb::MsMs 3400667 Specdb::MsMs 3400668 HMDB05056 #<Reference:0x000055ce317fe090> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Milk (Cow) Type 2 specific 0.29338 0.496 0.0109 uM Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823