Cyanidin 3-(6''-caffeyl-6'''-ferulylsophoroside) 5-glucoside (CHEM023840)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:19:27 UTC
Update Date2016-11-09 01:17:47 UTC
Accession NumberCHEM023840
Identification
Common NameCyanidin 3-(6''-caffeyl-6'''-ferulylsophoroside) 5-glucoside
ClassSmall Molecule
DescriptionCyanidin 3-(6''-caffeyl-6'''-ferulylsophoroside) 5-glucoside is a member of the class of compounds known as flavonoid 3-o-p-coumaroyl glycosides. Flavonoid 3-o-p-coumaroyl glycosides 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''-caffeyl-6'''-ferulylsophoroside) 5-glucoside is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Cyanidin 3-(6''-caffeyl-6'''-ferulylsophoroside) 5-glucoside can be found in radish and sweet potato, which makes cyanidin 3-(6''-caffeyl-6'''-ferulylsophoroside) 5-glucoside a potential biomarker for the consumption of these food products.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC52H55O27
Average Molecular Mass1111.977 g/mol
Monoisotopic Mass1111.293 g/mol
CAS Registry Number145815-06-1
IUPAC Name2-(3,4-dihydroxyphenyl)-3-{[(2R,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-({[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}oxan-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
Traditional Name2-(3,4-dihydroxyphenyl)-3-{[(2R,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-({[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}oxan-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
SMILESCOC1=C(O)C=CC(\C=C\C(=O)OC[C@H]2O[C@@H](O[C@H]3[C@@H](OC4=CC5=C(O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)C=C(O)C=C5[O+]=C4C4=CC=C(O)C(O)=C4)O[C@H](COC(=O)\C=C\C4=CC(O)=C(O)C=C4)[C@@H](O)[C@@H]3O)[C@H](O)[C@@H](O)[C@@H]2O)=C1
InChI IdentifierInChI=1S/C52H54O27/c1-70-33-13-22(3-8-28(33)57)5-11-39(61)71-19-36-41(63)44(66)47(69)51(77-36)79-49-45(67)42(64)37(20-72-38(60)10-4-21-2-7-26(55)29(58)12-21)78-52(49)75-34-17-25-31(73-48(34)23-6-9-27(56)30(59)14-23)15-24(54)16-32(25)74-50-46(68)43(65)40(62)35(18-53)76-50/h2-17,35-37,40-47,49-53,62-69H,18-20H2,1H3,(H5-,54,55,56,57,58,59,60,61)/p+1/t35-,36-,37-,40-,41-,42-,43+,44+,45+,46-,47-,49-,50-,51+,52+/m1/s1
InChI KeyCSWCMIODPBATKN-PPJFJRRFSA-O
Chemical Taxonomy
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
  • Hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Anthocyanidin
  • Phenolic glycoside
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid or derivatives
  • Cinnamic acid or derivatives
  • Cinnamic acid ester
  • Glycosyl compound
  • Disaccharide
  • O-glycosyl compound
  • Methoxyphenol
  • 1-benzopyran
  • Benzopyran
  • Methoxybenzene
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Catechol
  • Styrene
  • Fatty acid ester
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Oxane
  • Fatty acyl
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Ether
  • Polyol
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Carbonyl group
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Alcohol
  • Primary alcohol
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.19 g/LALOGPS
logP2.53ALOGPS
logP1.9ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)6.65ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count24ChemAxon
Hydrogen Donor Count15ChemAxon
Polar Surface Area433.8 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity272.36 m³·mol⁻¹ChemAxon
Polarizability105.74 ųChemAxon
Number of Rings8ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-99ff803b1da8d154683bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03fr-1900000000-a242992982340cc06d9fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-4900000000-47e302f24da9577a2924Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1900000000-fa583dd1ad047d1c7fa9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03fr-2900000000-793596618d087b614cefSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9200000000-572b0530d2040524aa42Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDFDB001581
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID101401134
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available