Cyanidin 3-O-(6''-malonyl-arabinoside) (CHEM022866)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 20:42:38 UTC
Update Date2016-11-09 01:17:35 UTC
Accession NumberCHEM022866
Identification
Common NameCyanidin 3-O-(6''-malonyl-arabinoside)
ClassSmall Molecule
DescriptionA polyphenol compound found in foods of plant origin (PhenolExplorer).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC23H21O13
Average Molecular Mass505.405 g/mol
Monoisotopic Mass505.098 g/mol
CAS Registry NumberNot Available
IUPAC Name3-{[(2R,3S,4S,5R)-5-{[(2-carboxyacetyl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1λ⁴-chromen-1-ylium
Traditional Name3-{[(2R,3S,4S,5R)-5-{[(2-carboxyacetyl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1λ⁴-chromen-1-ylium
SMILESO[C@@H]1[C@@H](COC(=O)CC(O)=O)O[C@H](OC2=CC3=C(O)C=C(O)C=C3[O+]=C2C2=CC=C(O)C(O)=C2)[C@H]1O
InChI IdentifierInChI=1S/C23H20O13/c24-10-4-13(26)11-6-16(22(34-15(11)5-10)9-1-2-12(25)14(27)3-9)35-23-21(32)20(31)17(36-23)8-33-19(30)7-18(28)29/h1-6,17,20-21,23,31-32H,7-8H2,(H4-,24,25,26,27,28,29)/p+1/t17-,20-,21+,23+/m1/s1
InChI KeyVXFDROQYRNLBSO-CPDIYIAASA-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
  • Hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Anthocyanidin
  • O-glycosyl compound
  • Glycosyl compound
  • 1-benzopyran
  • Pentose monosaccharide
  • Benzopyran
  • Catechol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Dicarboxylic acid or derivatives
  • 1,3-dicarbonyl compound
  • Monosaccharide
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Secondary alcohol
  • Carboxylic acid ester
  • 1,2-diol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organic oxide
  • Alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • 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 Solubility0.21 g/LALOGPS
logP2.04ALOGPS
logP1.35ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)3.31ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area216.58 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity125.79 m³·mol⁻¹ChemAxon
Polarizability47.39 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4r-9223400000-3cbbabdc5dbb1faa2ca3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-053r-9071607000-539add6aa762630cd291Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000090000-adfd5942a0353948eb4eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1000790000-e910c9c80cba0d6f69a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08fu-8920110000-c6738bb406393f40c44fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1000090000-b68e987e9bc925e5d610Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-9100270000-e0b2d66643da2687d250Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9600000000-6e6f0b3f4820390d0119Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090310000-24795e534cff505efb56Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0297600000-ee4baf862f2ec8f45173Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0079-4491000000-49e5ec215c33fba25a36Spectrum
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 IDHMDB0029243
FooDB IDFDB000062
Phenol Explorer ID82
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID30776745
ChEBI IDNot Available
PubChem Compound ID131750821
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Neveu V, Perez-Jimenez J, Vos F, Crespy V, du Chaffaut L, Mennen L, Knox C, Eisner R, Cruz J, Wishart D, Scalbert A: Phenol-Explorer: an online comprehensive database on polyphenol contents in foods. Database (Oxford). 2010;2010:bap024. doi: 10.1093/database/bap024. Epub 2010 Jan 8.