Malvidin 3-(6''-p-coumarylglucoside) 5-dimalonylglucoside (CHEM023853)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:19:55 UTC
Update Date2016-11-09 01:17:47 UTC
Accession NumberCHEM023853
Identification
Common NameMalvidin 3-(6''-p-coumarylglucoside) 5-dimalonylglucoside
ClassSmall Molecule
DescriptionMalvidin 3-(6''-p-coumarylglucoside) 5-dimalonylglucoside 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) 5-dimalonylglucoside is practically insoluble (in water) and a moderately acidic compound (based on its pKa). Malvidin 3-(6''-p-coumarylglucoside) 5-dimalonylglucoside can be found in hyssop, which makes malvidin 3-(6''-p-coumarylglucoside) 5-dimalonylglucoside a potential biomarker for the consumption of this food product.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC44H45O25
Average Molecular Mass973.813 g/mol
Monoisotopic Mass973.225 g/mol
CAS Registry Number144940-57-8
IUPAC Name5-{[(2S,3R,4R,5S,6R)-5-[(2-carboxyacetyl)oxy]-6-{[(2-carboxyacetyl)oxy]methyl}-3,4-dihydroxyoxan-2-yl]oxy}-7-hydroxy-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-{[(2S,3R,4R,5S,6R)-5-[(2-carboxyacetyl)oxy]-6-{[(2-carboxyacetyl)oxy]methyl}-3,4-dihydroxyoxan-2-yl]oxy}-7-hydroxy-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
SMILESCOC1=CC(=CC(OC)=C1O)C1=[O+]C2=CC(O)=CC(O[C@@H]3O[C@H](COC(=O)CC(O)=O)[C@@H](OC(=O)CC(O)=O)[C@H](O)[C@H]3O)=C2C=C1O[C@@H]1O[C@H](COC(=O)\C=C\C2=CC=C(O)C=C2)[C@@H](O)[C@H](O)[C@H]1O
InChI IdentifierInChI=1S/C44H44O25/c1-60-25-9-19(10-26(61-2)35(25)54)41-27(66-43-39(58)37(56)36(55)28(67-43)16-62-32(51)8-5-18-3-6-20(45)7-4-18)13-22-23(64-41)11-21(46)12-24(22)65-44-40(59)38(57)42(69-34(53)15-31(49)50)29(68-44)17-63-33(52)14-30(47)48/h3-13,28-29,36-40,42-44,55-59H,14-17H2,1-2H3,(H4-,45,46,47,48,49,50,51,54)/p+1/t28-,29-,36-,37+,38-,39-,40-,42-,43-,44-/m1/s1
InChI KeyWLRHEJRFVKWTOH-OUOHEMENSA-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
  • Anthocyanidin-5-o-glycoside
  • Anthocyanin
  • Anthocyanidin-3-o-glycoside
  • Flavonoid-3-o-glycoside
  • 3p-methoxyflavonoid-skeleton
  • 4'-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Anthocyanidin
  • Pentacarboxylic acid or derivatives
  • Phenolic glycoside
  • Coumaric acid ester
  • Cinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid or derivatives
  • Cinnamic acid ester
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • M-dimethoxybenzene
  • Methoxyphenol
  • Dimethoxybenzene
  • Anisole
  • Phenoxy compound
  • Methoxybenzene
  • Styrene
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fatty acid ester
  • Phenol
  • Alkyl aryl ether
  • Benzenoid
  • Oxane
  • Monosaccharide
  • 1,3-dicarbonyl compound
  • Monocyclic benzene moiety
  • Fatty acyl
  • Enoate ester
  • Heteroaromatic compound
  • Alpha,beta-unsaturated carboxylic ester
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Acetal
  • Carboxylic acid
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Polyol
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP2.57ALOGPS
logP1.49ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)2.94ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count21ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area383.86 ŲChemAxon
Rotatable Bond Count21ChemAxon
Refractivity231.89 m³·mol⁻¹ChemAxon
Polarizability91.7 ųChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-0000000009-ce6c916612559dc149c9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-0000000009-f779d0deba6643202cdeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000j-7301306039-206fc30b80d12c0fc612Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-1000000009-26275aec3699cdc3412eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0abi-9300000018-23c0f8b28e37be1753bdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zfr-9600001000-9353fc20ba4b744c0e23Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0301905
FooDB IDFDB001595
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID30780077
ChEBI IDNot Available
PubChem Compound ID101633887
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available