Record Information
Version1.0
Creation date2010-04-08 22:13:01 UTC
Update date2019-11-26 03:14:37 UTC
Primary IDFDB017307
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePeonidin 3-galactoside
DescriptionPeonidin 3-galactoside is a member of the class of compounds known as anthocyanidin-3-o-glycosides. Anthocyanidin-3-o-glycosides are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C3-position. Peonidin 3-galactoside is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Peonidin 3-galactoside can be found in a number of food items such as mango, red raspberry, rubus (blackberry, raspberry), and bilberry, which makes peonidin 3-galactoside a potential biomarker for the consumption of these food products.
CAS Number28148-89-2
Structure
Thumb
Synonyms
SynonymSource
3,4',5,7-Tetrahydroxy-3'-methoxyflavylium(1+); 3-O-D-Galactopyranosidedb_source
Peonidin 3-O-galactosidemanual
Predicted Properties
PropertyValueSource
Water Solubility0.42 g/LALOGPS
logP1.18ALOGPS
logP0.42ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)6.4ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area182.44 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity120.74 m³·mol⁻¹ChemAxon
Polarizability45.08 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC22H23O11
IUPAC name5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1lambda4-chromen-1-ylium
InChI IdentifierInChI=1S/C22H22O11/c1-30-15-4-9(2-3-12(15)25)21-16(7-11-13(26)5-10(24)6-14(11)31-21)32-22-20(29)19(28)18(27)17(8-23)33-22/h2-7,17-20,22-23,27-29H,8H2,1H3,(H2-,24,25,26)/p+1/t17-,18+,19+,20-,22-/m1/s1
InChI KeyZZWPMFROUHHAKY-VRRLNDPFSA-O
Isomeric SMILES[H][C@]1(CO)O[C@@]([H])(OC2=CC3=C(C=C(O)C=C3O)[O+]=C2C2=CC(OC)=C(O)C=C2)[C@]([H])(O)[C@@]([H])(O)[C@@]1([H])O
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
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • Anthocyanidin
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Methoxyphenol
  • 1-benzopyran
  • Benzopyran
  • Methoxybenzene
  • Phenoxy compound
  • Phenol ether
  • Anisole
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Monosaccharide
  • Oxane
  • Heteroaromatic compound
  • Secondary alcohol
  • Polyol
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Acetal
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Organooxygen compound
  • Primary alcohol
  • 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-c6004bf80dd72ad2bd7bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1300900000-cfe5d43e5a5ed6973d3fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ot-8911000000-c56dc49b6c675b18b7bdSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-2300900000-9e7364bc1ea3ed714e5aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-6700900000-759ae58a8bfcf0669b11Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0596-9300000000-c97a6a71b4c020768f6bSpectrum
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 ID34
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDCNL87-O:KXB33-Z
EAFUS IDNot Available
Dr. Duke IDPEONIDIN-3-GALACTOSIDE|PAEONIDIN-3-O-GALACTOSIDE|PEONIDIN-3-O-GALACTOSIDE
BIGG IDNot Available
KNApSAcK IDC00006680
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 ID34
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).