1.02011-04-11 17:01:52 UTC2019-11-26 03:20:55 UTCFDB021828EnterodiolEnterodiol 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-butanediolArbo 9C18H22O4302.3649302.1518091922,3-bis[(3-hydroxyphenyl)methyl]butane-1,4-diol2,3-bis[(3-hydroxyphenyl)methyl]butane-1,4-diol80226-00-2OCC(CC1=CC(O)=CC=C1)C(CO)CC1=CC=CC(O)=C1InChI=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,7-8,11-12H2DWONJCNDULPHLV-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 lignansOrganic compoundsLignans, neolignans and related compoundsDibenzylbutane lignansDibenzylbutanediol lignansAromatic homomonocyclic compounds1-hydroxy-2-unsubstituted benzenoids1-hydroxy-4-unsubstituted benzenoidsBenzene and substituted derivativesHydrocarbon derivativesPrimary alcohols1-hydroxy-2-unsubstituted benzenoid1-hydroxy-4-unsubstituted benzenoidAlcoholAromatic homomonocyclic compoundBenzenoidDibenzylbutanediolHydrocarbon derivativeMonocyclic benzene moietyOrganic oxygen compoundOrganooxygen compoundPhenolPrimary alcoholSolidlogp1.91logs-4.09solubility2.47e-02 g/llogp2.65pka_strongest_acidic9.79pka_strongest_basic-2.6iupac2,3-bis[(3-hydroxyphenyl)methyl]butane-1,4-diolaverage_mass302.3649mono_mass302.151809192smilesOCC(CC1=CC(O)=CC=C1)C(CO)CC1=CC=CC(O)=C1formulaC18H22O4inchiInChI=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,7-8,11-12H2inchikeyDWONJCNDULPHLV-UHFFFAOYSA-Npolar_surface_area80.92refractivity86.36polarizability32.34rotatable_bond_count7acceptor_count4donor_count4physiological_charge0formal_charge0Specdb::CMs114926Specdb::CMs129120Specdb::CMs814829Specdb::CMs814830Specdb::CMs814831Specdb::CMs814832Specdb::CMs814833Specdb::CMs814834Specdb::CMs814835Specdb::CMs814836Specdb::CMs814837Specdb::CMs814838Specdb::CMs814839Specdb::CMs814840Specdb::CMs814841Specdb::CMs814842Specdb::CMs814843Specdb::CMs814844Specdb::CMs814845Specdb::CMs814846Specdb::MsMs2227896Specdb::MsMs2229157Specdb::MsMs2230317Specdb::MsMs2231587Specdb::MsMs2232585Specdb::MsMs2234039Specdb::MsMs2234918Specdb::MsMs2252549Specdb::MsMs2253919Specdb::MsMs2254653Specdb::MsMs2258560Specdb::MsMs2258787Specdb::MsMs2259777Specdb::MsMs2260025Specdb::MsMs3400663Specdb::MsMs3400664Specdb::MsMs3400665Specdb::MsMs3400666Specdb::MsMs3400667Specdb::MsMs3400668HMDB05056#<Reference:0x0000555674e59668>AnatidaeType 1specificAnatidae8830BeefaloType 1specificBos taurus X Bison bison297284BisonType 1specificBison bison9901BuffaloType 1specificBubalus bubalis89462Cattle (Beef, Veal)Type 1specificBos taurus9913ChickenType 1specificGallus gallus9031Columbidae (Dove, Pigeon)Type 1specificColumbidae8930DeerType 1specificCervidae9850Domestic goatType 1specificCapra aegagrus hircus9925Domestic pigType 1specificSus scrofa domestica9825ElkType 1specificCervus canadensis1574408EmuType 1specificDromaius novaehollandiae8790European rabbitType 1specificOryctolagus9984Greylag gooseType 1specificAnser anser8843Guinea henType 1specificNumida meleagris8996HorseType 1specificEquus caballus9796Mallard duckType 1specificAnas platyrhynchos8839Milk (Cow)Type 2specific0.293380.4960.0109uMMountain hareType 1specificLepus timidus62621Mule deerType 1specificOdocoileus9871OstrichType 1specificStruthio camelus8801PheasantType 1specificPhasianus colchicus9054QuailType 1specificPhasianidae9005RabbitType 1specificLeporidae9979Rock ptarmiganType 1specificLagopus muta64668Sheep (Mutton, Lamb)Type 1specificOvis aries9940SquabType 1specificColumba8931TurkeyType 1specificMeleagris gallopavo9103Velvet duckType 1specificMelanitta fusca371864Wild boarType 1specificSus scrofa9823