5-Carboxypyranocyanidin 3-O-beta-glucopyranoside (CHEM023911)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:22:01 UTC
Update Date2016-11-09 01:17:48 UTC
Accession NumberCHEM023911
Identification
Common Name5-Carboxypyranocyanidin 3-O-beta-glucopyranoside
ClassSmall Molecule
Description5-carboxypyranocyanidin 3-o-beta-glucopyranoside is a member of the class of compounds known as anthocyanidin-3-o-glycosides. Anthocyanidin-3-o-glycosides are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C3-position. 5-carboxypyranocyanidin 3-o-beta-glucopyranoside is practically insoluble (in water) and a moderately acidic compound (based on its pKa). 5-carboxypyranocyanidin 3-o-beta-glucopyranoside can be found in garden onion, which makes 5-carboxypyranocyanidin 3-o-beta-glucopyranoside a potential biomarker for the consumption of this food product.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
5-Carboxypyranocyanidin 3-O-b-glucopyranosideGenerator
5-Carboxypyranocyanidin 3-O-β-glucopyranosideGenerator
Chemical FormulaC24H21O13
Average Molecular Mass517.416 g/mol
Monoisotopic Mass517.098 g/mol
CAS Registry Number566942-52-7
IUPAC Name7-carboxy-3-(3,4-dihydroxyphenyl)-11-hydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2λ⁴,8-dioxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),2,4,6,9,11-hexaen-2-ylium
Traditional Name7-carboxy-3-(3,4-dihydroxyphenyl)-11-hydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2λ⁴,8-dioxatricyclo[7.3.1.0⁵,¹³]trideca-1(13),2,4,6,9,11-hexaen-2-ylium
SMILESOC[C@H]1O[C@@H](OC2=C3C=C(OC4=CC(O)=CC([O+]=C2C2=CC(O)=C(O)C=C2)=C34)C(O)=O)[C@H](O)[C@@H](O)[C@@H]1O
InChI IdentifierInChI=1S/C24H20O13/c25-7-16-18(29)19(30)20(31)24(36-16)37-22-10-6-15(23(32)33)34-13-4-9(26)5-14(17(10)13)35-21(22)8-1-2-11(27)12(28)3-8/h1-6,16,18-20,24-25,29-31H,7H2,(H3-,26,27,28,32,33)/p+1/t16-,18-,19+,20-,24+/m1/s1
InChI KeyDTHNDBFHAFORNZ-KXJGTOPRSA-O
Chemical Taxonomy
Description belongs to the class of organic compounds known as anthocyanidin-3-o-glycosides. These are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C3-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentAnthocyanidin-3-O-glycosides
Alternative Parents
Substituents
  • Anthocyanidin-3-o-glycoside
  • Flavonoid-3-o-glycoside
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Anthocyanidin
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Monosaccharide
  • Benzenoid
  • Oxane
  • Heteroaromatic compound
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Acetal
  • Primary alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Organic oxygen compound
  • 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 Solubility0.47 g/LALOGPS
logP1.62ALOGPS
logP0.61ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)2.19ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area219.74 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity131.45 m³·mol⁻¹ChemAxon
Polarizability48.39 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0100090000-af732782630120bee19bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gb9-1200090000-1cdd3274fd5aa78c14d1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dm-7901210000-b81a630bb6701eb88b50Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2300090000-a0287c03f565878c72f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-6800090000-5b8302bbba187e1d3bf5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9500000000-838e34fab41fb364dd61Spectrum
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 IDHMDB0301949
FooDB IDFDB001662
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID30780078
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