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Showing Compound Cyanidin 3-galactoside p-coumaric acid ester (FDB007659)

Record Information
Version1.0
Creation date2010-04-08 22:07:43 UTC
Update date2019-11-26 03:01:44 UTC
Primary IDFDB007659
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCyanidin 3-galactoside p-coumaric acid ester
Description{[(2R,3R,4S,5R,6S)-6-{[2-(3,4-dihydroxyphenyl)-7-hydroxy-5-oxo-5H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl}[1-hydroxy-3-(4-hydroxyphenyl)prop-2-en-1-ylidene]oxidanium 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. Based on a literature review very few articles have been published on {[(2R,3R,4S,5R,6S)-6-{[2-(3,4-dihydroxyphenyl)-7-hydroxy-5-oxo-5H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl}[1-hydroxy-3-(4-hydroxyphenyl)prop-2-en-1-ylidene]oxidanium.
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.06 g/LALOGPS
logP3.23ALOGPS
logP3.8ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)6.39ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area219.74 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity157.81 m³·mol⁻¹ChemAxon
Polarizability59.38 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC30H27O13
IUPAC name2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4S,5R,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/C30H26O13/c31-16-5-1-14(2-6-16)3-8-25(36)40-13-24-26(37)27(38)28(39)30(43-24)42-23-12-18-20(34)10-17(32)11-22(18)41-29(23)15-4-7-19(33)21(35)9-15/h1-12,24,26-28,30,37-39H,13H2,(H4-,31,32,33,34,35,36)/p+1/t24-,26+,27+,28-,30-/m1/s1
InChI KeyQAOBEOXFSUJDJL-OROGXDDESA-O
Isomeric SMILESO[C@H]1[C@@H](COC(=O)\C=C\C2=CC=C(O)C=C2)O[C@@H](OC2=CC3=C(C=C(O)C=C3O)[O+]=C2C2=CC(O)=C(O)C=C2)[C@H](O)[C@H]1O
Average Molecular Weight595.5276
Monoisotopic Molecular Weight595.14516595
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
  • Anthocyanin
  • Anthocyanidin-3-o-glycoside
  • Flavonoid-3-o-glycoside
  • Hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Anthocyanidin
  • Coumaric acid ester
  • Cinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid or derivatives
  • Cinnamic acid ester
  • O-glycosyl compound
  • Glycosyl compound
  • 1-benzopyran
  • Benzopyran
  • Styrene
  • Catechol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fatty acid ester
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Fatty acyl
  • Benzenoid
  • Oxane
  • Monosaccharide
  • Monocyclic benzene moiety
  • Enoate ester
  • Heteroaromatic compound
  • Alpha,beta-unsaturated carboxylic ester
  • Secondary alcohol
  • Carboxylic acid ester
  • Oxacycle
  • Acetal
  • Organoheterocyclic compound
  • Polyol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Organic oxide
  • Alcohol
  • 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
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000092000-7de2decfd8bd19f3b6c02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0110098000-f22aa78942c38a2844732016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0941032000-c24ba17c47b36b09cdb72016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000090000-e00b5143612d3a500d242016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-1110193000-a677b7178e9fc2fb6faa2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a7l-7920000000-9052194ea5d339dc97882016-08-03View 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 IDCYANIDIN-3-GALACTOSIDE-P-COUMARIC-ACID-ESTER
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
CornExpected but not quantifiedNot AvailableDUKE
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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— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).