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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:29:08 UTC
Update Date2019-01-11 19:37:37 UTC
HMDB IDHMDB0029243
Secondary Accession Numbers
  • HMDB29243
Metabolite Identification
Common NameCyanidin 3-O-(6''-malonyl-arabinoside)
DescriptionCyanidin 3-O-(6''-malonyl-arabinoside) is a polyphenol compound found in foods of plant origin (PMID: 20428313 )
Structure
Data?1547235457
SynonymsNot Available
Chemical FormulaC23H21O13
Average Molecular Weight505.405
Monoisotopic Molecular Weight505.098215758
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
CAS Registry NumberNot Available
SMILES
O[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 Identifier
InChI=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
DescriptionThis compound 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
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • Anthocyanidin
  • O-glycosyl compound
  • Glycosyl compound
  • 1-benzopyran
  • Benzopyran
  • Resorcinol
  • 1,2-diphenol
  • Phenol
  • Benzenoid
  • 1,3-dicarbonyl compound
  • Monosaccharide
  • Dicarboxylic acid or derivatives
  • Saccharide
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Oxolane
  • Secondary alcohol
  • Carboxylic acid ester
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid
  • Carboxylic acid derivative
  • Acetal
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4r-9223400000-3cbbabdc5dbb1faa2ca3View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-053r-9071607000-539add6aa762630cd291View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000090000-adfd5942a0353948eb4eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1000790000-e910c9c80cba0d6f69a6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08fu-8920110000-c6738bb406393f40c44fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1000090000-b68e987e9bc925e5d610View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-9100270000-e0b2d66643da2687d250View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9600000000-6e6f0b3f4820390d0119View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID82
FoodDB IDFDB000062
KNApSAcK IDNot Available
Chemspider ID30776745
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not 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. [PubMed:20428313 ]