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Showing Compound Cyanidin 3-(6'',6'''-dicaffeylsophoroside) 5-glucoside (FDB001580)

Record Information
Version1.0
Creation date2010-04-08 22:05:01 UTC
Update date2019-11-26 02:56:36 UTC
Primary IDFDB001580
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCyanidin 3-(6'',6'''-dicaffeylsophoroside) 5-glucoside
DescriptionCyanidin 3-(6'',6'''-dicaffeylsophoroside) 5-glucoside 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. Cyanidin 3-(6'',6'''-dicaffeylsophoroside) 5-glucoside is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Cyanidin 3-(6'',6'''-dicaffeylsophoroside) 5-glucoside can be found in sweet potato, which makes cyanidin 3-(6'',6'''-dicaffeylsophoroside) 5-glucoside a potential biomarker for the consumption of this food product.
CAS Number170717-21-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.25 g/LALOGPS
logP2.43ALOGPS
logP1.87ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)6.65ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count24ChemAxon
Hydrogen Donor Count16ChemAxon
Polar Surface Area444.8 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity267.87 m³·mol⁻¹ChemAxon
Polarizability103.86 ųChemAxon
Number of Rings8ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC51H53O27
IUPAC name2-(3,4-dihydroxyphenyl)-3-{[(2R,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-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium
InChI IdentifierInChI=1S/C51H52O27/c52-17-34-39(62)42(65)45(68)49(75-34)73-32-15-23(53)14-31-24(32)16-33(47(72-31)22-5-8-27(56)30(59)13-22)74-51-48(44(67)41(64)36(77-51)19-71-38(61)10-4-21-2-7-26(55)29(58)12-21)78-50-46(69)43(66)40(63)35(76-50)18-70-37(60)9-3-20-1-6-25(54)28(57)11-20/h1-16,34-36,39-46,48-52,62-69H,17-19H2,(H6-,53,54,55,56,57,58,59,60,61)/p+1/t34-,35-,36-,39-,40-,41-,42+,43+,44+,45-,46-,48-,49-,50+,51+/m1/s1
InChI KeyQROHSXUMSFREKB-GTGMSLJISA-O
Isomeric SMILESOC[C@H]1O[C@@H](OC2=C3C=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(O)=C(O)C=C5)[C@@H](O)[C@H](O)[C@H]4O)C(=[O+]C3=CC(O)=C2)C2=CC=C(O)C(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O
Average Molecular Weight1097.9503
Monoisotopic Molecular Weight1097.27742149
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
  • Anthocyanidin-3-o-glycoside
  • Anthocyanidin-5-o-glycoside
  • Anthocyanin
  • Flavonoid-3-o-glycoside
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Anthocyanidin
  • Phenolic glycoside
  • Hydroxycinnamic acid or derivatives
  • Cinnamic acid or derivatives
  • Cinnamic acid ester
  • Coumaric acid or derivatives
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Styrene
  • Catechol
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Fatty acid ester
  • Fatty acyl
  • Oxane
  • Monocyclic benzene moiety
  • Benzenoid
  • Dicarboxylic acid or derivatives
  • Heteroaromatic compound
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Polyol
  • Oxacycle
  • Acetal
  • Organoheterocyclic compound
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Primary alcohol
  • Organic oxygen 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, Positivesplash10-0002-9600000000-846e67de1265ac88626c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-5900000000-f6496a211dc6abd4b97d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dj-6900000002-3dbac041e6b5e219f6822016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9300000000-d8875717d288864f99332016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dj-7900000001-8a27a36cdef9482c0ad92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9200000000-a9384ab7bcd7fb53cdd82016-08-03View 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 IDNot Available
BIGG IDNot Available
KNApSAcK IDC00006849
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.