Record Information
Version1.0
Creation date2010-04-08 22:12:57 UTC
Update date2019-11-26 03:14:26 UTC
Primary IDFDB017209
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameMalvidin 3-(6-acetylglucoside)
DescriptionMalvidin 3-(6-acetylglucoside) 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-(6-acetylglucoside) is found, on average, in the highest concentration within a few different foods, such as lowbush blueberries (Vaccinium angustifolium), common grapes (Vitis vinifera), and summer grapes (Vitis aestivalis) and in a lower concentration in grape wine and highbush blueberries (Vaccinium corymbosum). Malvidin 3-(6-acetylglucoside) has also been detected, but not quantified in, several different foods, such as alcoholic beverages, canada blueberries (Vaccinium myrtilloides), fruits, and rubus (blackberry, raspberry). This could make malvidin 3-(6-acetylglucoside) a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Malvidin 3-(6-acetylglucoside).
CAS Number101072-66-6
Structure
Thumb
Synonyms
SynonymSource
Malvidin 3-(6''-acetyl-glucoside)HMDB
Malvidin 3-(6''-acetylglucoside)HMDB
Malvidin 3-(6-acetyl-glucoside)HMDB
Malvidin 3-(6-acetylglucoside)db_source
Predicted Properties
PropertyValueSource
Water Solubility0.28 g/LALOGPS
logP2.01ALOGPS
logP0.6ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)6.38ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area197.74 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity136.35 m³·mol⁻¹ChemAxon
Polarizability51.69 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC25H27O13
IUPAC name3-({6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl}oxy)-5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-1lambda4-chromen-1-ylium
InChI IdentifierInChI=1S/C25H26O13/c1-10(26)35-9-19-21(30)22(31)23(32)25(38-19)37-18-8-13-14(28)6-12(27)7-15(13)36-24(18)11-4-16(33-2)20(29)17(5-11)34-3/h4-8,19,21-23,25,30-32H,9H2,1-3H3,(H2-,27,28,29)/p+1
InChI KeyWGYWEDJQQFKGID-UHFFFAOYSA-O
Isomeric SMILESCOC1=CC(=CC(OC)=C1O)C1=[O+]C2=C(C=C1OC1OC(COC(C)=O)C(O)C(O)C1O)C(O)=CC(O)=C2
Average Molecular Weight535.4741
Monoisotopic Molecular Weight535.14516595
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
  • O-glycosyl compound
  • Glycosyl compound
  • Dimethoxybenzene
  • 1-benzopyran
  • Benzopyran
  • Methoxyphenol
  • M-dimethoxybenzene
  • Anisole
  • Phenol ether
  • Phenoxy compound
  • Methoxybenzene
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Oxane
  • Monosaccharide
  • Heteroaromatic compound
  • Carboxylic acid ester
  • Secondary alcohol
  • Polyol
  • Ether
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 56.08%; H 5.08%; O 38.84%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-MS
TypeDescriptionSplash KeyView
Predicted GC-MSMalvidin 3-(6-acetylglucoside), non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0aor-9411530000-fb312406a9ece120e4deSpectrum
Predicted GC-MSMalvidin 3-(6-acetylglucoside), 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-08fr-5410019000-c5e5e237324ed88efc3eSpectrum
Predicted GC-MSMalvidin 3-(6-acetylglucoside), TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMalvidin 3-(6-acetylglucoside), TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMalvidin 3-(6-acetylglucoside), TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMalvidin 3-(6-acetylglucoside), TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMalvidin 3-(6-acetylglucoside), TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMalvidin 3-(6-acetylglucoside), TMS_1_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMalvidin 3-(6-acetylglucoside), TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMalvidin 3-(6-acetylglucoside), TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMalvidin 3-(6-acetylglucoside), TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMalvidin 3-(6-acetylglucoside), TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMalvidin 3-(6-acetylglucoside), TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMalvidin 3-(6-acetylglucoside), TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMalvidin 3-(6-acetylglucoside), TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMalvidin 3-(6-acetylglucoside), TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMalvidin 3-(6-acetylglucoside), TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMalvidin 3-(6-acetylglucoside), TMS_2_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMalvidin 3-(6-acetylglucoside), TMS_2_12, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMalvidin 3-(6-acetylglucoside), TMS_2_13, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMalvidin 3-(6-acetylglucoside), TMS_2_14, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMalvidin 3-(6-acetylglucoside), TMS_2_15, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMalvidin 3-(6-acetylglucoside), TMS_3_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMalvidin 3-(6-acetylglucoside), TMS_3_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMalvidin 3-(6-acetylglucoside), TMS_3_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1000090000-e857ea85883f56032fb3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-2000090000-4d09d4f291a00897ddcbSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06tp-9402000000-c3927eefc5edeb0dab37Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a59-9110070000-73b868f29b034349ac19Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000010000-47d6e068a08c0d3f577cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-bb500531150240ef3866Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03ei-0006890000-220deb208bc8abd6f080Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-1109620000-d2176e4106a44b009337Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00lr-1109100000-49e5f233fccc2dd4fc7bSpectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID46
DrugBank IDNot Available
HMDB IDHMDB38008
CRC / DFC (Dictionary of Food Compounds) IDCNF63-A:KWN83-P
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00006901
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 IDNot Available
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.