Record Information
Version1.0
Creation date2010-04-08 22:04:25 UTC
Update date2015-07-20 21:30:21 UTC
Primary IDFDB000055
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameMalvidin 3-(6''-caffeoyl-glucoside)
DescriptionNot Available
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
Malvidin 3-O-(6''-caffeoyl-glucoside)db_source
Predicted Properties
PropertyValueSource
Water Solubility0.0561 mg/mLALOGPS
logP3.31ALOGPS
logP3.3ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)6.38ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area238.2 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity170.73 m3·mol-1ChemAxon
Polarizability63.93 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC32H31O15
IUPAC name3-{[(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)-1λ⁴-chromen-1-ylium
InChI IdentifierInChI=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/s1
InChI KeyInChIKey=LIEHUFTYLLDHTI-FCOFYTSKSA-O
Isomeric SMILESCOC1=CC(=CC(OC)=C1O)C1=[O+]C2=C(C=C1OC1O[C@H](COC(=O)\C=C\C3=CC(O)=C(O)C=C3)[C@@H](O)[C@H](O)[C@H]1O)C(O)=CC(O)=C2
Average Molecular Weight655.5795
Monoisotopic Molecular Weight655.166295322
Classification
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassPhenylpropanoids and polyketides
Sub ClassFlavonoids
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
  • Hydroxycinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Cinnamic acid or derivatives
  • Cinnamic acid ester
  • Glycosyl compound
  • O-glycosyl compound
  • Dimethoxybenzene
  • M-dimethoxybenzene
  • Methoxyphenol
  • 1-benzopyran
  • Benzopyran
  • Styrene
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Methoxybenzene
  • Catechol
  • Phenol
  • Fatty acid ester
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-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 DescriptorsNot Available
Physico-Chemical Properties - Experimental
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
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID75
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 IDNot Available
HET 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[2] Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.