1.0 2020-05-06 19:44:04 UTC 2020-05-07 14:44:58 UTC BMDB0109727 Equol 7-O-glucuronide (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-{[(3S)-3-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}oxane-2-carboxylate C21H22O9 418.394 418.126382302 (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(3S)-3-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}oxane-2-carboxylic acid (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(3S)-3-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}oxane-2-carboxylic acid O[C@@H]1[C@@H](O)[C@H](OC2=CC3=C(C[C@H](CO3)C3=CC=C(O)C=C3)C=C2)O[C@@H]([C@H]1O)C(O)=O InChI=1S/C21H22O9/c22-13-4-1-10(2-5-13)12-7-11-3-6-14(8-15(11)28-9-12)29-21-18(25)16(23)17(24)19(30-21)20(26)27/h1-6,8,12,16-19,21-25H,7,9H2,(H,26,27)/t12-,16+,17+,18-,19+,21-/m1/s1 XDPLKWRSVXUQBN-LVEHSUOCSA-N belongs to the class of organic compounds known as flavonoid-7-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C7-position. Organic compounds Phenylpropanoids and polyketides Flavonoids Flavonoid glycosides Flavonoid-7-O-glucuronides 1-benzopyrans 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids 3'-hydroxyflavonoids 3-hydroxyflavonoids 4'-hydroxyflavonoids 5-hydroxyflavonoids Acetals Alkyl aryl ethers Benzene and substituted derivatives Beta hydroxy acids and derivatives Carbonyl compounds Carboxylic acids Catechins Catechols Flavonoid-7-O-glycosides Hexoses Hydrocarbon derivatives Monocarboxylic acids and derivatives O-glucuronides O-glycosyl compounds Organic oxides Oxacyclic compounds Oxanes Phenolic glycosides Polyols Pyrans Secondary alcohols 1-benzopyran 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 1-o-glucuronide 3'-hydroxyflavonoid 3-hydroxyflavonoid 4'-hydroxyflavonoid 5-hydroxyflavonoid Acetal Alcohol Alkyl aryl ether Aromatic heteropolycyclic compound Benzenoid Benzopyran Beta-hydroxy acid Carbonyl group Carboxylic acid Carboxylic acid derivative Catechin Catechol Chromane Ether Flavan Flavan-3-ol Flavonoid-7-o-glucuronide Flavonoid-7-o-glycoside Glucuronic acid or derivatives Glycosyl compound Hexose monosaccharide Hydrocarbon derivative Hydroxy acid Hydroxyflavonoid Monocarboxylic acid or derivatives Monocyclic benzene moiety Monosaccharide O-glucuronide O-glycosyl compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxane Phenol Phenolic glycoside Polyol Pyran Secondary alcohol Aromatic heteropolycyclic compounds logp 1.20 ALOGPS logs -2.73 ALOGPS logp 1.24 ChemAxon pka_strongest_acidic 3.01 ChemAxon pka_strongest_basic -3.7 ChemAxon iupac (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(3S)-3-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}oxane-2-carboxylic acid ChemAxon average_mass 418.394 ChemAxon mono_mass 418.126382302 ChemAxon smiles O[C@@H]1[C@@H](O)[C@H](OC2=CC3=C(C[C@H](CO3)C3=CC=C(O)C=C3)C=C2)O[C@@H]([C@H]1O)C(O)=O ChemAxon formula C21H22O9 ChemAxon inchi InChI=1S/C21H22O9/c22-13-4-1-10(2-5-13)12-7-11-3-6-14(8-15(11)28-9-12)29-21-18(25)16(23)17(24)19(30-21)20(26)27/h1-6,8,12,16-19,21-25H,7,9H2,(H,26,27)/t12-,16+,17+,18-,19+,21-/m1/s1 ChemAxon inchikey XDPLKWRSVXUQBN-LVEHSUOCSA-N ChemAxon polar_surface_area 145.91 ChemAxon refractivity 100.97 ChemAxon polarizability 41.56 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 9 ChemAxon donor_count 5 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 4 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Specdb::CMs 23849 Specdb::CMs 47512 Specdb::CMs 167938 Specdb::MsMs 318835 Specdb::MsMs 318836 Specdb::MsMs 318837 Specdb::MsMs 365767 Specdb::MsMs 365768 Specdb::MsMs 365769 Specdb::MsMs 2458640 Specdb::MsMs 2458641 Specdb::MsMs 2458642 Specdb::MsMs 2476574 Specdb::MsMs 2476575 Specdb::MsMs 2476576 Liver Metabolomics analysis was performed using GC-MS/LC-MS in multiparous Holstein dairy cows Shahzad K, Lopreiato V, Liang Y, Trevisi E, Osorio JS, Xu C, Loor JJ: Hepatic metabolomics and transcriptomics to study susceptibility to ketosis in response to prepartal nutritional management. J Anim Sci Biotechnol. 2019 Dec 18;10:96. doi: 10.1186/s40104-019-0404-z. eCollection 2019. 31867104 FDB029898 30777625 29979359