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Showing Compound Cyanidin 3-(6-caffeoylglucoside) 5-glucoside (FDB017172)

Record Information
Version1.0
Creation date2010-04-08 22:12:53 UTC
Update date2019-11-26 03:14:20 UTC
Primary IDFDB017172
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCyanidin 3-(6-caffeoylglucoside) 5-glucoside
DescriptionCyanidin 3-(6-caffeoylglucoside) 5-glucoside 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. Cyanidin 3-(6-caffeoylglucoside) 5-glucoside has been detected, but not quantified in, fats and oils and herbs and spices. This could make cyanidin 3-(6-caffeoylglucoside) 5-glucoside a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Cyanidin 3-(6-caffeoylglucoside) 5-glucoside.
CAS Number130009-41-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.31 g/LALOGPS
logP1.7ALOGPS
logP0.85ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)6.65ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area319.12 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity191.93 m³·mol⁻¹ChemAxon
Polarizability73.09 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC36H37O19
IUPAC name2-(3,4-dihydroxyphenyl)-3-{[6-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-7-hydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium
InChI IdentifierInChI=1S/C36H36O19/c37-12-25-28(44)30(46)32(48)35(54-25)52-23-10-16(38)9-22-17(23)11-24(34(51-22)15-3-5-19(40)21(42)8-15)53-36-33(49)31(47)29(45)26(55-36)13-50-27(43)6-2-14-1-4-18(39)20(41)7-14/h1-11,25-26,28-33,35-37,44-49H,12-13H2,(H4-,38,39,40,41,42,43)/p+1
InChI KeyVPWIBNQGHJUEJI-UHFFFAOYSA-O
Isomeric SMILESOCC1OC(OC2=CC(O)=CC3=[O+]C(=C(OC4OC(COC(=O)\C=C\C5=CC(O)=C(O)C=C5)C(O)C(O)C4O)C=C23)C2=CC(O)=C(O)C=C2)C(O)C(O)C1O
Average Molecular Weight773.6676
Monoisotopic Molecular Weight773.192904002
Classification
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
  • Anthocyanin
  • Anthocyanidin-5-o-glycoside
  • Anthocyanidin-3-o-glycoside
  • Flavonoid-3-o-glycoside
  • 7-hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • Hydroxyflavonoid
  • Anthocyanidin
  • Phenolic glycoside
  • Cinnamic acid ester
  • Cinnamic acid or derivatives
  • Hydroxycinnamic acid or derivatives
  • Coumaric acid or derivatives
  • O-glycosyl compound
  • Glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • Styrene
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Fatty acid ester
  • Phenol
  • Monosaccharide
  • Benzenoid
  • Monocyclic benzene moiety
  • Oxane
  • Fatty acyl
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Heteroaromatic compound
  • Secondary alcohol
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Polyol
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Primary alcohol
  • Alcohol
  • Hydrocarbon derivative
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCyanidin 3-(6-caffeoylglucoside) 5-glucoside, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-(6-caffeoylglucoside) 5-glucoside, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-(6-caffeoylglucoside) 5-glucoside, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-(6-caffeoylglucoside) 5-glucoside, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-(6-caffeoylglucoside) 5-glucoside, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-(6-caffeoylglucoside) 5-glucoside, TMS_1_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-(6-caffeoylglucoside) 5-glucoside, TMS_1_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-(6-caffeoylglucoside) 5-glucoside, TMS_1_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-(6-caffeoylglucoside) 5-glucoside, TMS_1_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-(6-caffeoylglucoside) 5-glucoside, TMS_1_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-(6-caffeoylglucoside) 5-glucoside, TMS_1_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-(6-caffeoylglucoside) 5-glucoside, TMS_1_12, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-(6-caffeoylglucoside) 5-glucoside, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-(6-caffeoylglucoside) 5-glucoside, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-(6-caffeoylglucoside) 5-glucoside, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-(6-caffeoylglucoside) 5-glucoside, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-(6-caffeoylglucoside) 5-glucoside, TBDMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-(6-caffeoylglucoside) 5-glucoside, TBDMS_1_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-(6-caffeoylglucoside) 5-glucoside, TBDMS_1_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-(6-caffeoylglucoside) 5-glucoside, TBDMS_1_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-(6-caffeoylglucoside) 5-glucoside, TBDMS_1_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-(6-caffeoylglucoside) 5-glucoside, TBDMS_1_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-(6-caffeoylglucoside) 5-glucoside, TBDMS_1_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCyanidin 3-(6-caffeoylglucoside) 5-glucoside, TBDMS_1_12, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0100000900-9c6f62903310481924d12016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-1200000900-c3803a49a56f4b3c84672016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dj-6900001200-c6e4e2625dfcc8c010182016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-1200000900-a98643c5a881cf740d652016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00fr-5700000900-73aa562b3723940f34ca2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9200000000-738eb313ccd2d201eb1d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0w2j-0530901400-fb8a1d5998466d2a1fdc2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0370813900-e046e54ce445eec305c82021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-1910020100-a626bdd2a15de799d9462021-09-22View 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 IDHMDB37983
CRC / DFC (Dictionary of Food Compounds) IDODW40-I:KWM95-P
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00006821
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 IDSCMQ73-Z:KWM95-P
Associated Foods
FoodContent Range AverageReference
Processing...
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