Record Information
Version1.0
Creation date2010-04-08 22:13:01 UTC
Update date2018-05-29 18:28:56 UTC
Primary IDFDB017308
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePeonidin 3-glucoside
DescriptionPeonidin 3-glucoside, also known as oxycoccicyanin, 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. Peonidin 3-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Peonidin 3-glucoside is found, on average, in the highest concentration within a few different foods, such as bilberries, lingonberries, and american cranberries and in a lower concentration in summer grapes, highbush blueberries, and grape wines. Peonidin 3-glucoside has also been detected, but not quantified in, several different foods, such as fruits, prunus (cherry, plum), wild rices, sorghums, and ryes. This could make peonidin 3-glucoside a potential biomarker for the consumption of these foods.
CAS Number68795-37-9
Structure
Thumb
Synonyms
SynonymSource
OxycoccicyaninChEBI
Peonidin 3-O-beta-D-glucosideChEBI
Peonidin 3-O-glucosideChEBI
Peonidin-3-glucosideChEBI
Peonidin 3-O-b-D-glucosideGenerator
Peonidin 3-O-β-D-glucosideGenerator
Peonidin 3-glucosideMeSH, HMDB
3'-O-Methylcyanidin 3-O-b-D-glucosideGenerator
3'-O-Methylcyanidin 3-O-β-D-glucosideGenerator
Peonidin-3-O-glucosideMeSH
Peonidin 3-O-beta-D-glucopyranosidebiospider
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
Polarizability45.05 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC22H23O11
IUPAC name5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-{[(2S,3R,4S,5S,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-OUUKCGNVSA-O
Isomeric SMILESCOC1=C(O)C=CC(=C1)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 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
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Anthocyanidin
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Dicarboxylic acid or derivatives
  • 1,3-dicarbonyl compound
  • Monosaccharide
  • Oxane
  • Heteroaromatic compound
  • Secondary alcohol
  • Carboxylic acid ester
  • Polyol
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organooxygen compound
  • Alcohol
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Foods

Beverages:

Fruits and vegetables:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
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
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ab9-9203500000-46d99ce5e8628cbe9157JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-03di-2331029000-917c43b617d07d6f073bJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0002-0090100000-0807279ecd58dbe38f4eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0039100000-cbeb7a2ec27315d1575aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0100900000-c6004bf80dd72ad2bd7bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1300900000-cfe5d43e5a5ed6973d3fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ot-8911000000-c56dc49b6c675b18b7bdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-2300900000-9e7364bc1ea3ed714e5aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-6700900000-759ae58a8bfcf0669b11JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0596-9300000000-c97a6a71b4c020768f6bJSpectraViewer
ChemSpider ID391786
ChEMBL IDCHEMBL1784263
KEGG Compound IDC12141
Pubchem Compound ID443654
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID743
DrugBank IDNot Available
HMDB IDHMDB13689
CRC / DFC (Dictionary of Food Compounds) IDCNL87-O:KXB34-A
EAFUS IDNot Available
Dr. Duke IDPEONIDIN-3-GLUCOSIDE|PEONIDIN-3-O-GLUCOSIDE|PAEONIDIN-3-GLUCOSIDE|PAEONIDIN-3-O-BETA-D-GLUCOSIDE|PAEONIDIN-3-O-GLUCOSIDE|PEONIDIN-3-O-BETA-D-GLUCOSIDE
BIGG IDNot Available
KNApSAcK IDC00006681
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 ID15
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
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.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.