Record Information
Version1.0
Creation date2010-04-08 22:12:57 UTC
Update date2019-11-26 03:14:27 UTC
Primary IDFDB017210
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameMalvidin 3-arabinoside
DescriptionMalvidin 3-arabinoside 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. Malvidin 3-arabinoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Malvidin 3-arabinoside is found, on average, in the highest concentration within a few different foods, such as highbush blueberries, bilberries, and lowbush blueberries. Malvidin 3-arabinoside has also been detected, but not quantified in, several different foods, such as strawberries, rabbiteye blueberries, red raspberries, sweet cherries, and rubus (blackberry, raspberry). This could make malvidin 3-arabinoside a potential biomarker for the consumption of these foods.
CAS Number28500-04-1
Structure
Thumb
Synonyms
SynonymSource
Malvidin 3-O-arabinosidemanual
Predicted Properties
PropertyValueSource
Water Solubility0.23 g/LALOGPS
logP1.71ALOGPS
logP0.84ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)6.38ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area171.44 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity121.24 m³·mol⁻¹ChemAxon
Polarizability45.19 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC22H23O11
IUPAC name3-{[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-1λ⁴-chromen-1-ylium
InChI IdentifierInChI=1S/C22H22O11/c1-29-14-3-9(4-15(30-2)18(14)26)21-16(32-22-20(28)19(27)17(8-23)33-22)7-11-12(25)5-10(24)6-13(11)31-21/h3-7,17,19-20,22-23,27-28H,8H2,1-2H3,(H2-,24,25,26)/p+1/t17-,19-,20+,22+/m1/s1
InChI KeyWNKBGLOGIZOFFU-PBVWOCPUSA-O
Isomeric SMILESCOC1=CC(=CC(OC)=C1O)C1=[O+]C2=C(C=C1O[C@H]1O[C@H](CO)[C@@H](O)[C@@H]1O)C(O)=CC(O)=C2
Average Molecular Weight463.4114
Monoisotopic Molecular Weight463.124036578
Classification
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
  • 3p-methoxyflavonoid-skeleton
  • Hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Anthocyanidin
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • Methoxyphenol
  • Pentose monosaccharide
  • 1-benzopyran
  • M-dimethoxybenzene
  • Dimethoxybenzene
  • Anisole
  • Phenol ether
  • Phenoxy compound
  • Methoxybenzene
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monosaccharide
  • Benzenoid
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Acetal
  • Ether
  • Alcohol
  • Organic oxygen compound
  • Primary alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 57.02%; H 5.00%; O 37.98%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0100900000-e48342e5c0bac076c15eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1300900000-e46b220de8efe1725b16Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-015a-9602000000-5da6fe45cec48869eb6bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1100900000-2845f6a7a2a86c49b9d1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03e9-2600900000-a4d1269bef86cb49b60aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f7p-7901000000-7d0acaa607a6361b9c02Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID25079994
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID37
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDCNF63-A:KWN84-Q
EAFUS IDNot Available
Dr. Duke IDMALVIDIN-3-O-ARABINOSIDE|MALVIDIN-3-O-ALPHA-L-ARABINOSIDE
BIGG IDNot Available
KNApSAcK IDC00006733
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite ID37
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).