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Showing Compound Malvidin 3-galactoside (FDB017212)

Record Information
Version1.0
Creation date2010-04-08 22:12:57 UTC
Update date2019-11-26 03:14:27 UTC
Primary IDFDB017212
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameMalvidin 3-galactoside
DescriptionIsolated from many plant subspecies inc. Vaccinium myrtillus (bilberry) and Vaccinium corymbosum (blueberry) Malvidin (Mv) is an anthocyanidin. As a primary plant pigment, its glycosides are highly abundant in nature. It is primarily responsible for the color of red wine, Vitis vinifera being one of its sources. It is also one of the anthocyanidins responsible for the blue pigment found in the Primula polyanthus plant.; Malvidin is an anthocyanin. Anthocyanins are pigments that give color red to red grape (Vitis vinifera) varieties, and blood oranges (Citrus sinensis (L.) Osbeck). (PMID: 15563216, 17425943); Anthocyanins have potentially chemopreventive activity, apart from its antioxidant activity. (PMID: 16080535); Numerous classes of grape anthocyanins are transferred to the wine and confer taste and color to the beverage. (PMID: 15954164); Anthocyanins are water soluble pigments belonging to the flavonoids compound family involved in nature in a wide range of functions such as flowers, fruits, and seeds pigmentation to attract pollinators, to disperse seeds, to protect against UV light damage, and in plant defense to protect against pathogen attack. Because anthocyanins impart much of the color and flavor of fruits and vegetables, they are usually components of the human diet and are not only considered exclusively as food products but also as therapeutic agents; in fact, anthocyanins have been suggested to protect against oxidative stress, coronary heart diseases, certain cancers, and other age-related diseases. At least part of these presumed health-promoting features can be attributed to the antioxidant properties of these compounds whose chemical structure appears ideal for free radical scavenging. (PMID: 16277406)
CAS Number30113-37-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Malvidin 3-O-beta-D-galactopyranosideHMDB
PrimulinHMDB
UliginosinHMDB
Malvidin 3-galactoside, chloride, (D)-isomerMeSH
Malvidin 3-galactosideMeSH
Predicted Properties
PropertyValueSource
Water Solubility0.46 g/LALOGPS
logP0.59ALOGPS
logP0.17ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)6.38ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area191.67 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity127.2 m³·mol⁻¹ChemAxon
Polarizability47.62 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-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-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
InChI KeyPXUQTDZNOHRWLI-UHFFFAOYSA-O
Isomeric SMILESCOC1=CC(=CC(OC)=C1O)C1=C(OC2OC(CO)C(O)C(O)C2O)C=C2C(O)=CC(O)=CC2=[O+]1
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 DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 55.98%; H 5.11%; O 38.91%DFC
Melting Point>300 oC
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-galactoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05fr-9201700000-5f224aacce0b77a00286Spectrum
Predicted GC-MSMalvidin 3-galactoside, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05fr-9300028000-6ce1f0efa7ecad1c1395Spectrum
Predicted GC-MSMalvidin 3-galactoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMalvidin 3-galactoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0100900000-033710abfed082d2d3702016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-1300900000-e69b0ff159f5593107232016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-8902100000-743f1ed57444e7ba81c82016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-2300900000-395bbc23a2b9330368ce2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-6700900000-535b30c2ac9d26860dd42016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0596-9300000000-0d5daf968ba28401b21c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001l-0005900000-76424194529c1604a3b82021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-1009500000-103645b5940ac4228fb62021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02ai-3039200000-e1c3b9411cfeaed0326d2021-09-25View Spectrum
NMRNot Available
ChemSpider ID2806159
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID3568969
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID54
DrugBank IDNot Available
HMDB IDHMDB38010
CRC / DFC (Dictionary of Food Compounds) IDCNF63-A:KWN87-T
EAFUS IDNot Available
Dr. Duke IDPRIMULIN|MALVIDIN-3-O-GALACTOSIDE
BIGG IDNot Available
KNApSAcK IDC00006734
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 ID54
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.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— 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.