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Showing Compound Cyanidin 3-[2-(6-(E)-caffeoyl-glucoside)-glucoside] 5-glucoside (FDB029881)

Record Information
Version1.0
Creation date2012-01-13 17:26:16 UTC
Update date2015-07-21 07:01:39 UTC
Primary IDFDB029881
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCyanidin 3-[2-(6-(E)-caffeoyl-glucoside)-glucoside] 5-glucoside
DescriptionCyanidin 3-[2-(6-(E)-caffeoyl-glucoside)-glucoside] 5-glucoside 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. Thus, cyanidin 3-[2-(6-(e)-caffeoyl-glucoside)-glucoside] 5-glucoside is considered to be a flavonoid. Based on a literature review a significant number of articles have been published on Cyanidin 3-[2-(6-(E)-caffeoyl-glucoside)-glucoside] 5-glucoside.
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.72 g/LALOGPS
logP1.27ALOGPS
logP-1.2ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)6.66ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count22ChemAxon
Hydrogen Donor Count14ChemAxon
Polar Surface Area387.27 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity228.83 m³·mol⁻¹ChemAxon
Polarizability91.98 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC43H49O24
IUPAC name3-{[(2S,3R,4S,5S,6R)-6-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-4,5-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium
InChI IdentifierInChI=1S/C43H48O24/c1-59-25-9-17(4-6-21(25)48)39-26(12-19-23(61-39)10-18(46)11-24(19)62-41-37(57)34(54)31(51)27(13-44)64-41)63-43-40(67-42-38(58)35(55)32(52)28(14-45)65-42)36(56)33(53)29(66-43)15-60-30(50)7-3-16-2-5-20(47)22(49)8-16/h2-12,27-29,31-38,40-45,51-58H,13-15H2,1H3,(H3-,46,47,48,49,50)/p+1/t27-,28-,29-,31-,32-,33-,34+,35+,36+,37-,38-,40-,41-,42+,43-/m1/s1
InChI KeyDGVPBUDMTNUREK-FRWPPZSRSA-O
Isomeric SMILESCOC1=CC(=CC=C1O)C1=[O+]C2=C(C=C1O[C@@H]1O[C@H](COC(=O)\C=C\C3=CC(O)=C(O)C=C3)[C@@H](O)[C@H](O)[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C(O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)=CC(O)=C2
Average Molecular Weight949.8348
Monoisotopic Molecular Weight949.261377496
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-5-o-glycoside
  • Anthocyanidin-3-o-glycoside
  • Flavonoid-3-o-glycoside
  • 3p-methoxyflavonoid-skeleton
  • 4'-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Anthocyanidin
  • Phenolic glycoside
  • Hydroxycinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Cinnamic acid ester
  • Cinnamic acid or derivatives
  • O-glycosyl compound
  • Disaccharide
  • Glycosyl compound
  • Methoxyphenol
  • 1-benzopyran
  • Benzopyran
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Catechol
  • Phenol ether
  • Styrene
  • Fatty acid ester
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Benzenoid
  • Fatty acyl
  • Oxane
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Ether
  • Polyol
  • Monocarboxylic acid or derivatives
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Carbonyl group
  • Primary alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Alcohol
  • Organooxygen compound
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Role

Biological role:

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, Positivesplash10-03dr-0212903702-98dcd971d66cebca60932017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0imi-0417907401-3f874e0dcf2179affcd62017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0w4i-0849707000-edfd5a393ed1b7abeb382017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03ej-0600400409-0bd3207adedb48777c7b2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01pa-0200303916-af32516282bd5f95699e2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01w0-0902101611-5718299e334666765e1c2021-09-25View 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 IDHMDB41715
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 ID757
Duplicate IDSNot Available
Old DFC IDSNot Available
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