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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2021-09-23 03:30:22 UTC
Update Date2021-09-23 03:30:22 UTC
HMDB IDHMDB0301903
Secondary Accession NumbersNone
Metabolite Identification
Common 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.
Structure
Thumb
Synonyms
ValueSource
Malvidin-3-O-(6-O-cis-p-coumaryl-beta-D-glucoside)ChEBI
Malvidin-3-O-(6-O-cis-p-coumaryl-b-D-glucoside)Generator
Malvidin-3-O-(6-O-cis-p-coumaryl-β-D-glucoside)Generator
Chemical FormulaC32H31O14
Average Molecular Weight639.5801
Monoisotopic Molecular Weight639.1713807
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
Traditional 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
CAS Registry NumberNot Available
SMILES
COC1=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
InChI Identifier
InChI=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
Chemical Taxonomy
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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+244.0532859911
AllCCS[M+H-H2O]+242.94132859911
AllCCS[M+Na]+245.31832859911
AllCCS[M+NH4]+245.04132859911
AllCCS[M-H]-237.96132859911
AllCCS[M+Na-2H]-240.28732859911
AllCCS[M+HCOO]-242.97732859911
DeepCCS[M+H]+231.6930932474
DeepCCS[M-H]-229.96630932474
DeepCCS[M-2H]-263.99830932474
DeepCCS[M+Na]+237.94630932474

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Malvidin 3-(6''-p-coumarylglucoside) 10V, Positive-QTOFsplash10-0006-0000009000-1529ed333cd50bcf17412016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Malvidin 3-(6''-p-coumarylglucoside) 20V, Positive-QTOFsplash10-0005-0000009000-b13e71615c867fe01a662016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Malvidin 3-(6''-p-coumarylglucoside) 40V, Positive-QTOFsplash10-004j-1906006000-dc03ad30277d31293c792016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Malvidin 3-(6''-p-coumarylglucoside) 10V, Negative-QTOFsplash10-000i-0000009000-6bededbf765c77e8b5b12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Malvidin 3-(6''-p-coumarylglucoside) 20V, Negative-QTOFsplash10-000i-1000009000-a5266829db42ad504af02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Malvidin 3-(6''-p-coumarylglucoside) 40V, Negative-QTOFsplash10-056r-9803012000-6f0c68fe01165f68beb02016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-17Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB001593
KNApSAcK IDNot Available
Chemspider ID30779237
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID75691
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available