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Peonidin 3-glucoside (FDB017308)

Record Information
Version1.0
Creation date2010-04-08 22:13:01 UTC
Update date2019-11-26 03:14:38 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 exists in all eukaryotes, ranging from yeast to plants to humans. Peonidin-3-glucoside is found, on average, in the highest concentration within a few different foods, such as bilberries (Vaccinium myrtillus), lingonberries (Vaccinium vitis-idaea), and american cranberries (Vaccinium macrocarpon) and in a lower concentration in sweet cherries (Prunus avium), lowbush blueberries (Vaccinium angustifolium), and grape wine. Peonidin-3-glucoside has also been detected, but not quantified in, several different foods, such as rabbiteye blueberries (Vaccinium virgatum), wild rice (Zizania), oats (Avena sativa), oriental wheats (Triticum turanicum), and sorghums (Sorghum bicolor). This could make peonidin-3-glucoside a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on Peonidin-3-glucoside.
CAS Number68795-37-9
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
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
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,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
  • 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 Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Foods

Beverages:

Fruits and vegetables:

Physico-Chemical Properties
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSPeonidin 3-glucoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ab9-9203500000-46d99ce5e8628cbe9157Spectrum
Predicted GC-MSPeonidin 3-glucoside, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03di-2331029000-917c43b617d07d6f073bSpectrum
Predicted GC-MSPeonidin 3-glucoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPeonidin 3-glucoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0002-0090100000-0807279ecd58dbe38f4e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0039100000-cbeb7a2ec27315d1575a2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0100900000-c6004bf80dd72ad2bd7b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1300900000-cfe5d43e5a5ed6973d3f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ot-8911000000-c56dc49b6c675b18b7bd2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-2300900000-9e7364bc1ea3ed714e5a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-6700900000-759ae58a8bfcf0669b112016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0596-9300000000-c97a6a71b4c020768f6b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0019000000-484bf4d661bc90952ec82021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0039200000-2f06e38c2f05d59c8b3b2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0w2d-6195100000-e9b66b1890c40defd5412021-09-24View Spectrum
NMRNot Available
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.