1.02010-04-08 22:04:25 UTC2019-11-26 02:54:30 UTCFDB000055Malvidin 3-(6''-caffeoyl-glucoside)Malvidin 3-(6''-caffeoyl-glucoside) is a member of the class of compounds known as flavonoid 3-o-p-coumaroyl glycosides. Flavonoid 3-o-p-coumaroyl glycosides are flavonoid 3-O-glycosides where the carbohydrate moiety is esterified with a p-coumaric acid. P-coumaric acid is an organic derivative of cinnamic acid, that carries a hydroxyl group at the 4-position of the benzene ring. Malvidin 3-(6''-caffeoyl-glucoside) is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Malvidin 3-(6''-caffeoyl-glucoside) can be found in grape wine, which makes malvidin 3-(6''-caffeoyl-glucoside) a potential biomarker for the consumption of this food product. Malvidin 3-O-(6''-caffeoyl-glucoside)C32H31O15655.5795655.1662953223-{[(3R,4S,5S,6R)-6-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-1lambda4-chromen-1-ylium3-{[(3R,4S,5S,6R)-6-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-1lambda4-chromen-1-ylium[H][C@]1(COC(=O)\C=C\C2=CC(O)=C(O)C=C2)OC(OC2=CC3=C(C=C(O)C=C3O)[O+]=C2C2=CC(OC)=C(O)C(OC)=C2)[C@]([H])(O)[C@@]([H])(O)[C@]1([H])OInChI=1S/C32H30O15/c1-42-22-8-15(9-23(43-2)27(22)38)31-24(12-17-19(35)10-16(33)11-21(17)45-31)46-32-30(41)29(40)28(39)25(47-32)13-44-26(37)6-4-14-3-5-18(34)20(36)7-14/h3-12,25,28-30,32,39-41H,13H2,1-2H3,(H4-,33,34,35,36,37,38)/p+1/t25-,28-,29+,30-,32?/m1/s1LIEHUFTYLLDHTI-FCOFYTSKSA-O belongs to the class of organic compounds known as flavonoid 3-o-p-coumaroyl glycosides. These are flavonoid 3-O-glycosides where the carbohydrate moiety is esterified with a p-coumaric acid. P-coumaric acid is an organic derivative of cinnamic acid, that carries a hydroxyl group at the 4-position of the benzene ring.Flavonoid 3-O-p-coumaroyl glycosidesOrganic compoundsPhenylpropanoids and polyketidesFlavonoidsFlavonoid glycosidesAromatic heteropolycyclic compounds1-benzopyrans1-hydroxy-2-unsubstituted benzenoids1-hydroxy-4-unsubstituted benzenoids3'-O-methylated flavonoids4'-hydroxyflavonoids5-hydroxyflavonoids7-hydroxyflavonoidsAcetalsAlkyl aryl ethersAnisolesAnthocyanidin-3-O-glycosidesAnthocyanidinsCarbonyl compoundsCatecholsCinnamic acid estersCoumaric acids and derivativesDimethoxybenzenesEnoate estersFatty acid estersFlavonoid-3-O-glycosidesHeteroaromatic compoundsHydrocarbon derivativesMethoxyphenolsMonocarboxylic acids and derivativesMonosaccharidesO-glycosyl compoundsOrganic cationsOrganic oxidesOxacyclic compoundsOxanesPhenoxy compoundsPolyolsSecondary alcoholsStyrenes1-benzopyran1-hydroxy-2-unsubstituted benzenoid1-hydroxy-4-unsubstituted benzenoid3p-methoxyflavonoid-skeleton4'-hydroxyflavonoid5-hydroxyflavonoid7-hydroxyflavonoidAcetalAlcoholAlkyl aryl etherAlpha,beta-unsaturated carboxylic esterAnisoleAnthocyanidinAnthocyanidin-3-o-glycosideAnthocyaninAromatic heteropolycyclic compoundBenzenoidBenzopyranCarbonyl groupCarboxylic acid derivativeCarboxylic acid esterCatecholCinnamic acid esterCinnamic acid or derivativesCoumaric acid or derivativesDimethoxybenzeneEnoate esterEtherFatty acid esterFatty acylFlavonoid 3-o-6-p-coumaroyl-glycosideFlavonoid-3-o-glycosideGlycosyl compoundHeteroaromatic compoundHydrocarbon derivativeHydroxycinnamic acid or derivativesHydroxyflavonoidM-dimethoxybenzeneMethoxybenzeneMethoxyphenolMonocarboxylic acid or derivativesMonocyclic benzene moietyMonosaccharideO-glycosyl compoundOrganic cationOrganic oxideOrganic oxygen compoundOrganoheterocyclic compoundOrganooxygen compoundOxacycleOxanePhenolPhenol etherPhenoxy compoundPolyolSecondary alcoholStyrenelogp3.31logs-4.09solubility5.61e-02 g/llogp3.3pka_strongest_acidic6.38pka_strongest_basic-3.6iupac3-{[(3R,4S,5S,6R)-6-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-1lambda4-chromen-1-yliumaverage_mass655.5795mono_mass655.166295322smiles[H][C@]1(COC(=O)\C=C\C2=CC(O)=C(O)C=C2)OC(OC2=CC3=C(C=C(O)C=C3O)[O+]=C2C2=CC(OC)=C(O)C(OC)=C2)[C@]([H])(O)[C@@]([H])(O)[C@]1([H])OformulaC32H31O15inchiInChI=1S/C32H30O15/c1-42-22-8-15(9-23(43-2)27(22)38)31-24(12-17-19(35)10-16(33)11-21(17)45-31)46-32-30(41)29(40)28(39)25(47-32)13-44-26(37)6-4-14-3-5-18(34)20(36)7-14/h3-12,25,28-30,32,39-41H,13H2,1-2H3,(H4-,33,34,35,36,37,38)/p+1/t25-,28-,29+,30-,32?/m1/s1inchikeyLIEHUFTYLLDHTI-FCOFYTSKSA-Opolar_surface_area238.2refractivity170.73polarizability63.93rotatable_bond_count10acceptor_count14donor_count8physiological_charge0formal_charge1Specdb::MsMs55341Specdb::MsMs55342Specdb::MsMs55343Specdb::MsMs110472Specdb::MsMs110473Specdb::MsMs110474Grape wineType 2specific0.1860040.1860041020.186004102mg/100 g