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Showing Compound Cyanidin 3-O-(6-trans-p-coumaroyl-2-O-beta-D-xylopyranosyl)-beta-D-glucopyranoside (FDB007035)

Record Information
Version1.0
Creation date2010-04-08 22:07:25 UTC
Update date2019-11-26 03:01:26 UTC
Primary IDFDB007035
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCyanidin 3-O-(6-trans-p-coumaroyl-2-O-beta-D-xylopyranosyl)-beta-D-glucopyranoside
Description{[(2R,3S,4S,5R,6S)-5-{[(2S,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-6-{[2-(3,4-dihydroxyphenyl)-7-hydroxy-5-oxo-5H-chromen-3-yl]oxy}-3,4-dihydroxyoxan-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,3S,4S,5R,6S)-5-{[(2S,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-6-{[2-(3,4-dihydroxyphenyl)-7-hydroxy-5-oxo-5H-chromen-3-yl]oxy}-3,4-dihydroxyoxan-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 Solubility0.21 g/LALOGPS
logP2.66ALOGPS
logP2.36ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)6.39ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area278.66 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity184.26 m³·mol⁻¹ChemAxon
Polarizability72.1 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC35H35O17
IUPAC name3-{[(2S,3R,4S,5S,6R)-3-{[(2S,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1λ⁴-chromen-1-ylium
InChI IdentifierInChI=1S/C35H34O17/c36-13-25-28(43)31(46)34(50-25)52-33-30(45)29(44)26(14-47-27(42)8-3-15-1-5-17(37)6-2-15)51-35(33)49-24-12-19-21(40)10-18(38)11-23(19)48-32(24)16-4-7-20(39)22(41)9-16/h1-12,25-26,28-31,33-36,43-46H,13-14H2,(H4-,37,38,39,40,41,42)/p+1/t25-,26-,28+,29-,30+,31-,33-,34+,35-/m1/s1
InChI KeyMKFRVEBQJPDQQX-LEHVFQNWSA-O
Isomeric SMILESOC[C@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C=C(O)C=C4O)[O+]=C3C3=CC(O)=C(O)C=C3)O[C@H](COC(=O)\C=C\C3=CC=C(O)C=C3)[C@@H](O)[C@@H]2O)[C@H](O)[C@H]1O
Average Molecular Weight727.6422
Monoisotopic Molecular Weight727.187424694
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
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Anthocyanidin
  • Coumaric acid ester
  • Cinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid or derivatives
  • Cinnamic acid ester
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • 1-benzopyran
  • Benzopyran
  • Styrene
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Fatty acid ester
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Fatty acyl
  • Monocyclic benzene moiety
  • Oxane
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Secondary alcohol
  • Carboxylic acid ester
  • Oxacycle
  • Acetal
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Primary alcohol
  • Hydrocarbon derivative
  • Alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • 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, Positivesplash10-004i-2300000900-0ebafdfe016a879158262016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-1400000900-146c82c9f208f3999a662016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00lu-9610002100-1a7e2baf5e8e6ef1dbfe2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0500000900-4d8e1551519162feb9b02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000t-0900000200-54bda022277f563392402016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fsm-3900000000-cd7943a767b8c2f9e7b42016-08-03View 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-O-(6-TRANS-P-COUMAROYL-2-O-BETA-D-XYLOPYRANOSYL)-BETA-D-GLUCOPYRANOSIDE
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
Black elderberryExpected 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).