Cyanidin 3-O-(6-O-cis-p-coumaroyl-2-O-beta-D-xylopyranosyl)-beta-D-glucopyranoside 5-O-beta-D-glucopyranoside (CHEM026271)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 22:53:46 UTC
Update Date2016-11-09 01:18:14 UTC
Accession NumberCHEM026271
Identification
Common NameCyanidin 3-O-(6-O-cis-p-coumaroyl-2-O-beta-D-xylopyranosyl)-beta-D-glucopyranoside 5-O-beta-D-glucopyranoside
ClassSmall Molecule
DescriptionCyanidin 3-o-(6-o-trans-p-coumaroyl-2-o-beta-d-xylopyranosyl)-beta-d-glucopyranoside 5-o-beta-d-glucopyranoside is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Cyanidin 3-o-(6-o-trans-p-coumaroyl-2-o-beta-d-xylopyranosyl)-beta-d-glucopyranoside 5-o-beta-d-glucopyranoside can be found in black elderberry, which makes cyanidin 3-o-(6-o-trans-p-coumaroyl-2-o-beta-d-xylopyranosyl)-beta-d-glucopyranoside 5-o-beta-d-glucopyranoside a potential biomarker for the consumption of this food product.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Cyanidin 3-O-(6-O-cis-p-coumaroyl-2-O-b-D-xylopyranosyl)-b-D-glucopyranoside 5-O-b-D-glucopyranosideGenerator
Cyanidin 3-O-(6-O-cis-p-coumaroyl-2-O-β-D-xylopyranosyl)-β-D-glucopyranoside 5-O-β-D-glucopyranosideGenerator
Cyanidin 3-O-(6-O-trans-p-coumaroyl-2-O-b-D-xylopyranosyl)-b-D-glucopyranoside 5-O-b-D-glucopyranosideGenerator
Cyanidin 3-O-(6-O-trans-p-coumaroyl-2-O-β-D-xylopyranosyl)-β-D-glucopyranoside 5-O-β-D-glucopyranosideGenerator
Cyanidin 3-O-(6-O-trans-p-coumaroyl-2-O-b-D-xylopyranosyl)-b-D-glucopyranoside 5-O-b-D-glucopyranosideGenerator
Cyanidin 3-O-(6-O-trans-p-coumaroyl-2-O-β-D-xylopyranosyl)-β-D-glucopyranoside 5-O-β-D-glucopyranosideGenerator
Chemical FormulaC41H45O22
Average Molecular Mass889.783 g/mol
Monoisotopic Mass889.240 g/mol
CAS Registry NumberNot Available
IUPAC Name3-{[(2S,3R,4S,5S,6R)-3-{[(2S,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-7-hydroxy-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium
Traditional Name3-{[(2S,3R,4S,5S,6R)-3-{[(2S,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-7-hydroxy-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium
SMILESOC[C@H]1O[C@@H](O[C@H]2[C@H](OC3=CC4=C(C=C(O)C=C4O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[O+]=C3C3=CC(O)=C(O)C=C3)O[C@H](COC(=O)\C=C\C3=CC=C(O)C=C3)[C@@H](O)[C@@H]2O)[C@H](O)[C@H]1O
InChI IdentifierInChI=1S/C41H44O22/c42-13-26-30(49)33(52)36(55)39(60-26)58-24-11-19(45)10-23-20(24)12-25(37(57-23)17-4-7-21(46)22(47)9-17)59-41-38(63-40-35(54)31(50)27(14-43)61-40)34(53)32(51)28(62-41)15-56-29(48)8-3-16-1-5-18(44)6-2-16/h1-12,26-28,30-36,38-43,49-55H,13-15H2,(H3-,44,45,46,47,48)/p+1/t26-,27-,28-,30-,31+,32-,33+,34+,35-,36-,38-,39-,40+,41-/m1/s1
InChI KeyWBNFGIPSBMHEGF-OLWQACOESA-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
  • Anthocyanidin-5-o-glycoside
  • Anthocyanidin-3-o-glycoside
  • Anthocyanin
  • Flavonoid-3-o-glycoside
  • 3'-hydroxyflavonoid
  • Hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Anthocyanidin
  • Phenolic glycoside
  • Coumaric acid ester
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid or derivatives
  • Cinnamic acid or derivatives
  • Cinnamic acid ester
  • O-glycosyl compound
  • Disaccharide
  • Glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fatty acid ester
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Oxane
  • Fatty acyl
  • Heteroaromatic compound
  • Alpha,beta-unsaturated carboxylic ester
  • Tetrahydrofuran
  • Enoate ester
  • Secondary alcohol
  • Carboxylic acid ester
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Organic oxide
  • 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 Solubility0.53 g/LALOGPS
logP1.51ALOGPS
logP-0.31ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)6.65ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area357.81 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity216.4 m³·mol⁻¹ChemAxon
Polarizability87.4 ųChemAxon
Number of Rings7ChemAxon
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, Positivesplash10-0006-0300000090-e9e6db4d78a34eaf15e0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-1500000090-33ae959a6cf8ef0ecabbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03ed-6900000020-469f703aaf63e8f96d2fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000j-1600000090-0992a0310695e181e148Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000t-1900000010-f3a5f0d33e5e310fa7ecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fsm-5900000000-bc99215d01d3372b3d5fSpectrum
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 IDFDB007033
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 IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available