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Showing Compound Pelargonidin 3-O-[2-O-(6-(E)-caffeoyl-beta-D-glucopyranosyl)-6-O-(E)-caffeoyl-beta-D-glucopyranoside] 5-O-(beta-D-glucopyranoside) (FDB001726)

Record Information
Version1.0
Creation date2010-04-08 22:05:05 UTC
Update date2019-11-26 02:56:39 UTC
Primary IDFDB001726
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePelargonidin 3-O-[2-O-(6-(E)-caffeoyl-beta-D-glucopyranosyl)-6-O-(E)-caffeoyl-beta-D-glucopyranoside] 5-O-(beta-D-glucopyranoside)
DescriptionPelargonidin 3-o-[2-o-(6-(e)-caffeoyl-beta-d-glucopyranosyl)-6-o-(e)-caffeoyl-beta-d-glucopyranoside] 5-o-(beta-d-glucopyranoside) is a member of the class of compounds known as anthocyanidin 3-o-6-p-coumaroyl glycosides. Anthocyanidin 3-o-6-p-coumaroyl glycosides 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. Pelargonidin 3-o-[2-o-(6-(e)-caffeoyl-beta-d-glucopyranosyl)-6-o-(e)-caffeoyl-beta-d-glucopyranoside] 5-o-(beta-d-glucopyranoside) is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Pelargonidin 3-o-[2-o-(6-(e)-caffeoyl-beta-d-glucopyranosyl)-6-o-(e)-caffeoyl-beta-d-glucopyranoside] 5-o-(beta-d-glucopyranoside) can be found in radish, which makes pelargonidin 3-o-[2-o-(6-(e)-caffeoyl-beta-d-glucopyranosyl)-6-o-(e)-caffeoyl-beta-d-glucopyranoside] 5-o-(beta-d-glucopyranoside) a potential biomarker for the consumption of this food product.
CAS Number776278-54-7
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.15 g/LALOGPS
logP2.33ALOGPS
logP2.15ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)6.66ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count23ChemAxon
Hydrogen Donor Count15ChemAxon
Polar Surface Area424.57 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity265.89 m³·mol⁻¹ChemAxon
Polarizability104.99 ųChemAxon
Number of Rings8ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC51H53O26
IUPAC name3-{[(2S,3R,4S,5S,6R)-6-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3-{[(2S,3R,4S,5S,6R)-6-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl]oxy}-7-hydroxy-2-(4-hydroxyphenyl)-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium
InChI IdentifierInChI=1S/C51H52O26/c52-18-34-39(61)42(64)45(67)49(74-34)72-32-16-25(54)15-31-26(32)17-33(47(71-31)23-5-7-24(53)8-6-23)73-51-48(44(66)41(63)36(76-51)20-70-38(60)12-4-22-2-10-28(56)30(58)14-22)77-50-46(68)43(65)40(62)35(75-50)19-69-37(59)11-3-21-1-9-27(55)29(57)13-21/h1-17,34-36,39-46,48-52,61-68H,18-20H2,(H5-,53,54,55,56,57,58,59,60)/p+1/t34-,35-,36-,39-,40-,41-,42+,43+,44+,45-,46-,48-,49-,50+,51-/m1/s1
InChI KeyVFGAHYZGQSWYGB-RPCOPJSUSA-O
Isomeric SMILESOC[C@H]1O[C@@H](OC2=CC(O)=CC3=[O+]C(=C(O[C@@H]4O[C@H](COC(=O)\C=C\C5=CC(O)=C(O)C=C5)[C@@H](O)[C@H](O)[C@H]4O[C@@H]4O[C@H](COC(=O)\C=C\C5=CC=C(O)C(O)=C5)[C@@H](O)[C@H](O)[C@H]4O)C=C23)C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O
Average Molecular Weight1081.9509
Monoisotopic Molecular Weight1081.282506868
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
  • 7-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • Hydroxyflavonoid
  • Anthocyanidin
  • Phenolic glycoside
  • Hydroxycinnamic acid or derivatives
  • Cinnamic acid ester
  • Cinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Glycosyl compound
  • O-glycosyl compound
  • Disaccharide
  • Benzopyran
  • 1-benzopyran
  • Styrene
  • Catechol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fatty acid ester
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Fatty acyl
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Oxane
  • Benzenoid
  • Heteroaromatic compound
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Primary alcohol
  • Organooxygen compound
  • 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, Positivesplash10-001j-9100000000-eb3bb553eba46b448e742016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000t-9200000000-eb12d7a1923a246b76282016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dj-6910000001-b90cf2ec29bb6e5157432016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-9100000000-ef003192109f44cf84a72016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003s-9400000001-03bd6729082374d6cd242016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9200001000-afd68bc23085feb1a50c2016-08-04View 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 IDNot Available
BIGG IDNot Available
KNApSAcK IDC00014834
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
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— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.