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Showing Compound p-Coumaroyl vitisin A (FDB000048)

Record Information
Version1.0
Creation date2010-04-08 22:04:25 UTC
Update date2018-05-28 22:34:11 UTC
Primary IDFDB000048
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namep-Coumaroyl vitisin A
Descriptionp-Coumaroyl vitisin A belongs to the class of organic compounds known as anthocyanidin 3-o-6-p-coumaroyl glycosides. These are anthocyanidin 3-O-glycosides where the carbohydrate moiety is esterified at the C6 position 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. p-Coumaroyl vitisin A is an extremely weak basic (essentially neutral) compound (based on its pKa).
CAS Number643-84-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Malvidin 3-(6-coumaroyl)-glucoside pyruvic acidHMDB
Malvidin 3-(6-coumaroyl)-glucoside pyruvic adductHMDB
Predicted Properties
PropertyValueSource
Water Solubility0.028 g/LALOGPS
logP3.19ALOGPS
logP3.8ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)2.11ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area244.27 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity183.94 m³·mol⁻¹ChemAxon
Polarizability68.47 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC35H31O16
IUPAC name7-carboxy-11-hydroxy-3-(4-hydroxy-3,5-dimethoxyphenyl)-4-{[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-2λ⁴,8-dioxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),2,4,6,9,11-hexaen-2-ylium
InChI IdentifierInChI=1S/C35H30O16/c1-45-22-9-16(10-23(46-2)28(22)39)32-33(19-13-24(34(43)44)48-20-11-18(37)12-21(49-32)27(19)20)51-35-31(42)30(41)29(40)25(50-35)14-47-26(38)8-5-15-3-6-17(36)7-4-15/h3-13,25,29-31,35,40-42H,14H2,1-2H3,(H3-,36,37,38,39,43,44)/p+1/t25-,29-,30+,31-,35?/m1/s1
InChI KeyGOINLVYYMYVHAQ-CJKUAQFFSA-O
Isomeric SMILESCOC1=CC(=CC(OC)=C1O)C1=[O+]C2=C3C(OC(=CC3=C1OC1O[C@H](COC(=O)\C=C\C3=CC=C(O)C=C3)[C@@H](O)[C@H](O)[C@H]1O)C(O)=O)=CC(O)=C2
Average Molecular Weight707.611
Monoisotopic Molecular Weight707.161209944
Classification
Description Belongs to the class of organic compounds known as anthocyanidin 3-o-6-p-coumaroyl glycosides. These are anthocyanidin 3-O-glycosides where the carbohydrate moiety is esterified at the C6 position 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 ParentAnthocyanidin 3-O-6-p-coumaroyl glycosides
Alternative Parents
Substituents
  • Anthocyanidin 3-o-6-p-coumaroyl-glycoside
  • Proanthocyanidin
  • Bi- and polyflavonoid skeleton
  • Anthocyanin
  • Anthocyanidin-3-o-glycoside
  • Flavonoid-3-o-glycoside
  • 3p-methoxyflavonoid-skeleton
  • Hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Anthocyanidin
  • Coumaric acid ester
  • Hydroxycinnamic acid or derivatives
  • Cinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Cinnamic acid ester
  • Glycosyl compound
  • O-glycosyl compound
  • Methoxyphenol
  • 1-benzopyran
  • Benzopyran
  • M-dimethoxybenzene
  • Dimethoxybenzene
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Styrene
  • Phenol ether
  • Fatty acid ester
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Fatty acyl
  • Benzenoid
  • Monocyclic benzene moiety
  • Oxane
  • Dicarboxylic acid or derivatives
  • Monosaccharide
  • Heteroaromatic compound
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid
  • Ether
  • Acetal
  • Polyol
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Alcohol
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID66
DrugBank IDNot Available
HMDB IDHMDB29239
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
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
FoodReference
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