1.0 2010-04-08 22:12:42 UTC 2025-11-19 01:50:40 UTC FDB016876 Isorhamnetin 3-glucuronide 6-{[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4h-chromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid is a member of the class of compounds known as flavonoid-3-o-glucuronides. Flavonoid-3-o-glucuronides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C3-position. 6-{[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4h-chromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid is slightly soluble (in water) and a moderately acidic compound (based on its pKa). 6-{[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4h-chromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid can be found in a number of food items such as cloudberry, dill, strawberry, and chicory, which makes 6-{[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4h-chromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid a potential biomarker for the consumption of these food products. Isorhamnetin 3-glucuronide Isorhamnetin 3-O-glucuronide C22H20O13 492.3864 492.090390726 6-{[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid 6-{[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid 36687-76-0 COC1=C(O)C=CC(=C1)C1=C(OC2OC(C(O)C(O)C2O)C(O)=O)C(=O)C2=C(O)C=C(O)C=C2O1 InChI=1S/C22H20O13/c1-32-11-4-7(2-3-9(11)24)18-19(14(26)13-10(25)5-8(23)6-12(13)33-18)34-22-17(29)15(27)16(28)20(35-22)21(30)31/h2-6,15-17,20,22-25,27-29H,1H3,(H,30,31) VVZWHOMBDMMRSC-UHFFFAOYSA-N belongs to the class of organic compounds known as flavonoid-3-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C3-position. Flavonoid-3-O-glucuronides Organic compounds Phenylpropanoids and polyketides Flavonoids Flavonoid glycosides Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids 3'-O-methylated flavonoids 4'-hydroxyflavonoids 5-hydroxyflavonoids 7-hydroxyflavonoids Acetals Alkyl aryl ethers Anisoles Beta hydroxy acids and derivatives Carbonyl compounds Carboxylic acids Chromones Flavones Flavonoid-3-O-glycosides Heteroaromatic compounds Hexoses Hydrocarbon derivatives Methoxybenzenes Methoxyphenols Monocarboxylic acids and derivatives O-glucuronides O-glycosyl compounds Organic oxides Oxacyclic compounds Oxanes Phenoxy compounds Polyols Pyranones and derivatives Secondary alcohols Vinylogous acids 1-benzopyran 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 1-o-glucuronide 3p-methoxyflavonoid-skeleton 4'-hydroxyflavonoid 5-hydroxyflavonoid 7-hydroxyflavonoid Acetal Alcohol Alkyl aryl ether Anisole Aromatic heteropolycyclic compound Benzenoid Benzopyran Beta-hydroxy acid Carbonyl group Carboxylic acid Carboxylic acid derivative Chromone Ether Flavone Flavonoid-3-o-glucuronide Flavonoid-3-o-glycoside Glucuronic acid or derivatives Glycosyl compound Heteroaromatic compound Hexose monosaccharide Hydrocarbon derivative Hydroxy acid Hydroxyflavonoid Methoxybenzene Methoxyphenol 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 Phenol ether Phenoxy compound Polyol Pyran Pyranone Secondary alcohol Vinylogous acid logp 1.40 ALOGPS logs -2.46 ALOGPS solubility 1.71e+00 g/l ALOGPS logp 0.32 ChemAxon pka_strongest_acidic 2.65 ChemAxon pka_strongest_basic -3.7 ChemAxon iupac 6-{[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid ChemAxon average_mass 492.3864 ChemAxon mono_mass 492.090390726 ChemAxon smiles COC1=C(O)C=CC(=C1)C1=C(OC2OC(C(O)C(O)C2O)C(O)=O)C(=O)C2=C(O)C=C(O)C=C2O1 ChemAxon formula C22H20O13 ChemAxon inchi InChI=1S/C22H20O13/c1-32-11-4-7(2-3-9(11)24)18-19(14(26)13-10(25)5-8(23)6-12(13)33-18)34-22-17(29)15(27)16(28)20(35-22)21(30)31/h2-6,15-17,20,22-25,27-29H,1H3,(H,30,31) ChemAxon inchikey VVZWHOMBDMMRSC-UHFFFAOYSA-N ChemAxon polar_surface_area 212.67 ChemAxon refractivity 113.63 ChemAxon polarizability 45.09 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 13 ChemAxon donor_count 7 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 67458 Specdb::MsMs 67459 Specdb::MsMs 67460 Specdb::MsMs 125289 Specdb::MsMs 125290 Specdb::MsMs 125291 Specdb::MsMs 2813042 Specdb::MsMs 2813043 Specdb::MsMs 2813044 Specdb::MsMs 2896074 Specdb::MsMs 2896075 Specdb::MsMs 2896076 Specdb::CMs 51835 Specdb::CMs 72256 Specdb::CMs 131673 Specdb::CMs 139407 Chicory Type 1 specific Cichorium intybus 13427 Cloudberry Type 1 specific Rubus chamaemorus 57936 0.0 0.0 0.0 mg/100 g Dill Type 1 specific Anethum graveolens 40922 Red raspberry Type 1 specific Rubus idaeus 32247 0.0 0.0 0.0 mg/100 g Strawberry Type 1 specific Fragaria X ananassa 3747 0.0 0.0 0.0 mg/100 g