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Showing Compound Malvidin 3-(6''-p-coumarylglucoside) (FDB001593)

Record Information
Version1.0
Creation date2010-04-08 22:05:01 UTC
Update date2019-11-26 02:56:36 UTC
Primary IDFDB001593
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameMalvidin 3-(6''-p-coumarylglucoside)
DescriptionMalvidin 3-(6''-p-coumarylglucoside) 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''-p-coumarylglucoside) is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Malvidin 3-(6''-p-coumarylglucoside) can be synthesized from cis-4-coumaric acid. Malvidin 3-(6''-p-coumarylglucoside) can also be synthesized into malvidin. Malvidin 3-(6''-p-coumarylglucoside) can be found in common grape and grape, which makes malvidin 3-(6''-p-coumarylglucoside) a potential biomarker for the consumption of these food products. Malvidin 3-(6''-p-coumarylglucoside) may be a unique S.cerevisiae (yeast) metabolite.
CAS Number156577-22-9
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.03 g/LALOGPS
logP3.41ALOGPS
logP3.58ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)6.38ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area217.97 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity168.75 m³·mol⁻¹ChemAxon
Polarizability64.11 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC32H31O14
IUPAC name5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium
InChI IdentifierInChI=1S/C32H30O14/c1-41-22-9-16(10-23(42-2)27(22)37)31-24(13-19-20(35)11-18(34)12-21(19)44-31)45-32-30(40)29(39)28(38)25(46-32)14-43-26(36)8-5-15-3-6-17(33)7-4-15/h3-13,25,28-30,32,38-40H,14H2,1-2H3,(H3-,33,34,35,36,37)/p+1/t25-,28-,29+,30-,32-/m1/s1
InChI KeyHXQOVGDXCHFLOP-KWNZYCHBSA-O
Isomeric SMILESCOC1=CC(=CC(OC)=C1O)C1=[O+]C2=C(C=C1O[C@@H]1O[C@H](COC(=O)\C=C\C3=CC=C(O)C=C3)[C@@H](O)[C@H](O)[C@H]1O)C(O)=CC(O)=C2
Average Molecular Weight639.5801
Monoisotopic Molecular Weight639.1713807
Classification
Description 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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid 3-O-p-coumaroyl glycosides
Alternative Parents
Substituents
  • Flavonoid 3-o-6-p-coumaroyl-glycoside
  • Anthocyanin
  • Anthocyanidin-3-o-glycoside
  • Flavonoid-3-o-glycoside
  • 3p-methoxyflavonoid-skeleton
  • Hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Anthocyanidin
  • Coumaric acid ester
  • Hydroxycinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Cinnamic acid ester
  • Cinnamic acid or derivatives
  • Glycosyl compound
  • O-glycosyl compound
  • Dimethoxybenzene
  • M-dimethoxybenzene
  • 1-benzopyran
  • Methoxyphenol
  • Benzopyran
  • Phenoxy compound
  • Phenol ether
  • Styrene
  • Anisole
  • Methoxybenzene
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Fatty acid ester
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Fatty acyl
  • Benzenoid
  • Monocyclic benzene moiety
  • Oxane
  • Monosaccharide
  • Heteroaromatic compound
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Secondary alcohol
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Acetal
  • Polyol
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000009000-1529ed333cd50bcf17412016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0005-0000009000-b13e71615c867fe01a662016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004j-1906006000-dc03ad30277d31293c792016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000009000-6bededbf765c77e8b5b12016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1000009000-a5266829db42ad504af02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-9803012000-6f0c68fe01165f68beb02016-08-03View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00006903
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.