Record Information
Version1.0
Creation date2010-04-08 22:05:29 UTC
Update date2020-02-24 19:10:36 UTC
Primary IDFDB002714
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameMalvidin 3-glucoside
DescriptionMalvidin 3-glucoside, also known as enin, 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. Thus, malvidin 3-glucoside is considered to be a flavonoid. Malvidin 3-glucoside is found, on average, in the highest concentration within a few different foods, such as bilberries (Vaccinium myrtillus), common grapes (Vitis vinifera), and lowbush blueberries (Vaccinium angustifolium) and in a lower concentration in grape wine, summer grapes (Vitis aestivalis), and common beans (Phaseolus vulgaris). Malvidin 3-glucoside has also been detected, but not quantified in, several different foods, such as strawberries (Fragaria X ananassa), bulgur, breakfast cereal, quinoas (Chenopodium quinoa), and corns (Zea mays). This could make malvidin 3-glucoside a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Malvidin 3-glucoside.
CAS Number7228-78-6
Structure
Thumb
Synonyms
SynonymSource
EninChEBI
Malvidin 3-O-glucosideChEBI
Malvidin-3-glucosideChEBI
EnosideHMDB
LigulinHMDB
Malvidin 3-O-beta-D-glucopyranosideHMDB
OeninHMDB
(3'-O-Methyl-(3)H)malvidin-3-glucosideMeSH, HMDB
Malvidin 3-O-b-D-glucosideGenerator
Malvidin 3-O-β-D-glucosideGenerator
Malvidin 3-glucosidedb_source
Predicted Properties
PropertyValueSource
Water Solubility0.37 g/LALOGPS
logP1.3ALOGPS
logP0.17ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)6.38ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area191.67 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity127.2 m³·mol⁻¹ChemAxon
Polarizability48.11 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC23H25O12
IUPAC name5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1lambda4-chromen-1-ylium
InChI IdentifierInChI=1S/C23H24O12/c1-31-14-3-9(4-15(32-2)18(14)27)22-16(7-11-12(26)5-10(25)6-13(11)33-22)34-23-21(30)20(29)19(28)17(8-24)35-23/h3-7,17,19-21,23-24,28-30H,8H2,1-2H3,(H2-,25,26,27)/p+1/t17-,19-,20+,21-,23-/m1/s1
InChI KeyPXUQTDZNOHRWLI-OXUVVOBNSA-O
Isomeric SMILESCOC1=CC(=CC(OC)=C1O)C1=[O+]C2=CC(O)=CC(O)=C2C=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
Average Molecular Weight493.4374
Monoisotopic Molecular Weight493.134601264
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
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • Methoxyphenol
  • M-dimethoxybenzene
  • 1-benzopyran
  • Dimethoxybenzene
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Methoxybenzene
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Oxane
  • Monosaccharide
  • Monocyclic benzene moiety
  • Benzenoid
  • Heteroaromatic compound
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Acetal
  • Polyol
  • Ether
  • Alcohol
  • Primary alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Foods

Beverages:

Fruits and vegetables:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 55.98%; H 5.11%; O 38.91%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -421 (0.1% HCl aq.)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSMalvidin 3-glucoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05fr-9201700000-0ec30e0735e5e1b81e53Spectrum
Predicted GC-MSMalvidin 3-glucoside, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05fr-9300028000-6ce1f0efa7ecad1c1395Spectrum
Predicted GC-MSMalvidin 3-glucoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-01t9-0039200000-77ef9771ee1d763a34e0Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0009100000-bbda7893855eb8d30b35Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT 34V, positivesplash10-001i-0009000000-570f6715d3a0cce22a54Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT 34V, positivesplash10-001i-0009000000-d83659bb1f771c8f19e4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0100900000-033710abfed082d2d370Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-1300900000-e69b0ff159f559310723Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-8902100000-743f1ed57444e7ba81c8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-2300900000-395bbc23a2b9330368ceSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-6700900000-535b30c2ac9d26860dd4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0596-9300000000-0d5daf968ba28401b21cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0009000000-cfefa087ac0a3dacce87Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0009100000-8140eb995136f11dd05eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000x-4029100000-7ae2183f72df310ed37cSpectrum
NMRNot Available
ChemSpider ID391785
ChEMBL IDCHEMBL403236
KEGG Compound IDC12140
Pubchem Compound ID443652
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID36
DrugBank IDNot Available
HMDB IDHMDB30777
CRC / DFC (Dictionary of Food Compounds) IDCNF63-A:CNF65-C
EAFUS IDNot Available
Dr. Duke IDOENIN|MALVIDIN-3-O-BETA-D-GLUCOSIDE|MALVIDIN-3-O-BETA-GLUCOSIDE|MALVIDIN-3-GLUCOSIDE|MALVIDIN-3-O-GLUCOSIDE
BIGG IDNot Available
KNApSAcK IDC00006735
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 ID36
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— 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.
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).