1.0 2011-03-17 23:25:05 UTC 2025-11-19 02:38:44 UTC FDB021629 Isorhamnetin 3-O-b-D-glucopyranoside Isorhamnetin 3-o-b-d-glucopyranoside, also known as isorhamnetin-3-O-galactoside, is a member of the class of compounds known as flavonoid-3-o-glycosides. Flavonoid-3-o-glycosides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. Thus, isorhamnetin 3-o-b-d-glucopyranoside is considered to be a flavonoid lipid molecule. Isorhamnetin 3-o-b-d-glucopyranoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Isorhamnetin 3-o-b-d-glucopyranoside can be found in a number of food items such as common grape, caraway, ginkgo nuts, and grape wine, which makes isorhamnetin 3-o-b-d-glucopyranoside a potential biomarker for the consumption of these food products. 3-Glucosylisorhamnetin 3,4',5,7-Tetrahydroxy-3'-methoxyflavone; 3-O-b-D-Glucopyranoside Isorhamnetin 3-glucoside Isorhamnetin 3-O-beta-D-glucopyranoside Isorhamnetin 3-O-beta-D-glucoside Isorhamnetin 3-O-glucoside C22H22O12 478.4029 478.111126168 5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one isorhamnetin 3-galactoside 5041-82-7 COC1=C(O)C=CC(=C1)C1=C(OC2OC(CO)C(O)C(O)C2O)C(=O)C2=C(O)C=C(O)C=C2O1 InChI=1S/C22H22O12/c1-31-12-4-8(2-3-10(12)25)20-21(17(28)15-11(26)5-9(24)6-13(15)32-20)34-22-19(30)18(29)16(27)14(7-23)33-22/h2-6,14,16,18-19,22-27,29-30H,7H2,1H3 CQLRUIIRRZYHHS-UHFFFAOYSA-N belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. Flavonoid-3-O-glycosides 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 Chromones Flavones Heteroaromatic compounds Hexoses Hydrocarbon derivatives Methoxybenzenes Methoxyphenols O-glycosyl compounds Organic oxides Oxacyclic compounds Oxanes Phenoxy compounds Polyols Primary alcohols Pyranones and derivatives Secondary alcohols Vinylogous acids 1-benzopyran 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 3p-methoxyflavonoid-skeleton 4'-hydroxyflavonoid 5-hydroxyflavonoid 7-hydroxyflavonoid Acetal Alcohol Alkyl aryl ether Anisole Aromatic heteropolycyclic compound Benzenoid Benzopyran Chromone Ether Flavone Flavonoid-3-o-glycoside Glycosyl compound Heteroaromatic compound Hexose monosaccharide Hydrocarbon derivative Hydroxyflavonoid Methoxybenzene Methoxyphenol Monocyclic benzene moiety Monosaccharide O-glycosyl compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxane Phenol Phenol ether Phenoxy compound Polyol Primary alcohol Pyran Pyranone Secondary alcohol Vinylogous acid Flavones and Flavonols logp 0.64 ALOGPS logs -2.59 ALOGPS solubility 1.22e+00 g/l ALOGPS melting_point Mp 215-218° (177-179°) logp 0.0011 ChemAxon pka_strongest_acidic 6.37 ChemAxon pka_strongest_basic -3 ChemAxon iupac 5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one ChemAxon average_mass 478.4029 ChemAxon mono_mass 478.111126168 ChemAxon smiles COC1=C(O)C=CC(=C1)C1=C(OC2OC(CO)C(O)C(O)C2O)C(=O)C2=C(O)C=C(O)C=C2O1 ChemAxon formula C22H22O12 ChemAxon inchi InChI=1S/C22H22O12/c1-31-12-4-8(2-3-10(12)25)20-21(17(28)15-11(26)5-9(24)6-13(15)32-20)34-22-19(30)18(29)16(27)14(7-23)33-22/h2-6,14,16,18-19,22-27,29-30H,7H2,1H3 ChemAxon inchikey CQLRUIIRRZYHHS-UHFFFAOYSA-N ChemAxon polar_surface_area 195.6 ChemAxon refractivity 113.76 ChemAxon polarizability 45.37 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 12 ChemAxon donor_count 7 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 1235095 Specdb::MsMs 1235096 Specdb::MsMs 1235097 Specdb::MsMs 1350577 Specdb::MsMs 1350578 Specdb::MsMs 1350579 Specdb::MsMs 3045082 Specdb::MsMs 3045083 Specdb::MsMs 3045084 Specdb::MsMs 3094627 Specdb::MsMs 3094628 Specdb::MsMs 3094629 Specdb::CMs 51832 Specdb::CMs 66540 Specdb::CMs 148883 Apple Type 1 specific Malus pumila 283210 0.0 0.0 0.0 mg/100 g Caraway Type 1 specific Carum carvi 48032 Chives Type 1 specific Allium schoenoprasum 74900 Common grape Type 1 specific Vitis vinifera 29760 0.056667 0.170000002 0.0 mg/100 g Corn Type 1 specific Zea mays 4577 Garden onion Type 1 specific Allium cepa 4679 Ginkgo nuts Type 1 specific Ginkgo biloba 3311 Grape wine Type 2 specific 0.266545 0.266545458 0.266545458 mg/100 g Guava Type 1 specific Psidium guajava 120290 Mugwort Type 1 specific Artemisia vulgaris 4220 Pear Type 1 specific Pyrus communis 23211 0.453333 0.453333336 0.453333336 mg/100 g Rocket salad (ssp.) Type 1 specific Eruca vesicaria ssp. sativa 29727 Sea-buckthornberry Type 1 specific Hippophae rhamnoides 193516 8.1 8.099999905 8.099999905 mg/100 g White lupine Type 1 specific Lupinus albus 3870 Hepatoprotective 981 Any compound that is able to prevent damage to the liver.