Cyanidin 3-O-alpha-L-arabinoside (CHEM026371)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 22:57:02 UTC
Update Date2016-11-09 01:18:15 UTC
Accession NumberCHEM026371
Identification
Common NameCyanidin 3-O-alpha-L-arabinoside
ClassSmall Molecule
DescriptionCyanidin 3-o-alpha-l-arabinoside is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Cyanidin 3-o-alpha-l-arabinoside can be found in cocoa bean and highbush blueberry, which makes cyanidin 3-o-alpha-l-arabinoside a potential biomarker for the consumption of these food products.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Cyanidin 3-O-a-L-arabinosideGenerator
Cyanidin 3-O-α-L-arabinosideGenerator
Chemical FormulaC20H19O10
Average Molecular Mass419.359 g/mol
Monoisotopic Mass419.098 g/mol
CAS Registry NumberNot Available
IUPAC Name3-{[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1λ⁴-chromen-1-ylium
Traditional Name3-{[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1λ⁴-chromen-1-ylium
SMILESOC[C@@H]1O[C@@H](OC2=CC3=C(C=C(O)C=C3O)[O+]=C2C2=CC(O)=C(O)C=C2)[C@H](O)[C@H]1O
InChI IdentifierInChI=1S/C20H18O10/c21-7-16-17(26)18(27)20(30-16)29-15-6-10-12(24)4-9(22)5-14(10)28-19(15)8-1-2-11(23)13(25)3-8/h1-6,16-18,20-21,26-27H,7H2,(H3-,22,23,24,25)/p+1/t16-,17-,18+,20+/m0/s1
InChI KeySBBFXSBQYRSIPP-PNYFIKQUSA-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
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • Hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • Anthocyanidin
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • Pentose monosaccharide
  • 1-benzopyran
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Monosaccharide
  • Benzenoid
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Secondary alcohol
  • Oxacycle
  • Acetal
  • Organoheterocyclic compound
  • Organooxygen compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • 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 Solubility0.41 g/LALOGPS
logP1.45ALOGPS
logP1.06ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)6.39ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area173.21 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity110.3 m³·mol⁻¹ChemAxon
Polarizability40.52 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0100900000-3041b66e8d6681bd3472Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-1503900000-bc4d12f32cf1fbcf3849Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-015a-9811000000-07dbd49948dfe40c532dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-1100900000-d33ab909b74980c6c8b9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-2700900000-08d40f3ce0497d9ba4f2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f7o-8910000000-f8bf46d87b7b44cfdeb2Spectrum
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 IDHMDB0303036
FooDB IDFDB007413
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID30780105
ChEBI IDNot Available
PubChem Compound ID157010022
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available