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Petunidin 3-glucoside (FDB017317)

Record Information
Version1.0
Creation date2010-04-08 22:13:01 UTC
Update date2019-11-26 03:14:39 UTC
Primary IDFDB017317
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePetunidin 3-glucoside
DescriptionPetunidin 3-glucoside 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. Thus, petunidin 3-glucoside is considered to be a flavonoid. Petunidin 3-glucoside is found, on average, in the highest concentration within a few different foods, such as bilberries (Vaccinium myrtillus), red wine, and lowbush blueberries (Vaccinium angustifolium) and in a lower concentration in common beans (Phaseolus vulgaris), common grapes (Vitis vinifera), and grape wine. Petunidin 3-glucoside has also been detected, but not quantified in, several different foods, such as rubus (blackberry, raspberry), amaranths (Amaranthus), mangos (Mangifera indica), teffs (Eragrostis tef), and american cranberries (Vaccinium macrocarpon). This could make petunidin 3-glucoside a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Petunidin 3-glucoside.
CAS Number6988-81-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.56 g/LALOGPS
logP1.04ALOGPS
logP0.13ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)6.39ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area202.67 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity122.72 m³·mol⁻¹ChemAxon
Polarizability46.02 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC22H23O12
IUPAC name2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1lambda4-chromen-1-ylium
InChI IdentifierInChI=1S/C22H22O12/c1-31-14-3-8(2-12(26)17(14)27)21-15(6-10-11(25)4-9(24)5-13(10)32-21)33-22-20(30)19(29)18(28)16(7-23)34-22/h2-6,16,18-20,22-23,28-30H,7H2,1H3,(H3-,24,25,26,27)/p+1/t16-,18-,19+,20-,22-/m1/s1
InChI KeyCCQDWIRWKWIUKK-QKYBYQKWSA-O
Isomeric SMILESCOC1=C(O)C(O)=CC(=C1)C1=[O+]C2=C(C=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C(O)=CC(O)=C2
Average Molecular Weight479.4108
Monoisotopic Molecular Weight479.1189512
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
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Anthocyanidin
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • 1-benzopyran
  • Benzopyran
  • Methoxyphenol
  • Catechol
  • Phenoxy compound
  • Methoxybenzene
  • Phenol ether
  • Anisole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Oxane
  • Benzenoid
  • Monosaccharide
  • Heteroaromatic compound
  • Secondary alcohol
  • Polyol
  • Acetal
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Alcohol
  • Primary alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Foods

Beverages:

Fruits and vegetables:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 55.12%; H 4.84%; O 40.05%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-MSPetunidin 3-glucoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0c00-9202600000-bb4dcb814381854b440eSpectrum
Predicted GC-MSPetunidin 3-glucoside, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-056r-5200009000-2e410453c726e39598f9Spectrum
Predicted GC-MSPetunidin 3-glucoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-02di-0179400000-8c080d5270ed5c16fe1d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0019100000-5a17dc990408af3c64fe2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-014i-0009000000-dae68e5430cb57fe90512021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0100900000-4e230c9c75d1eceddb032016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-1300900000-e28496a489aceb0b03122016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ot-7902000000-fe3ed6f122197848b0512016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2300900000-95c33029acb7b38c997b2016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-7700900000-0cb37887a196ba53e45b2016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0596-9300000000-e40e5b54f384481a079a2016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0009100000-bb6ace18d3e8492948d72021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0009300000-2f45b8c4cc2e84e428ec2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0wmj-2759200000-4b3d72708e7d59317a962021-09-22View Spectrum
NMRNot Available
ChemSpider ID391784
ChEMBL IDCHEMBL1784264
KEGG Compound IDC12139
Pubchem Compound ID443651
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID33
DrugBank IDNot Available
HMDB IDHMDB38097
CRC / DFC (Dictionary of Food Compounds) IDCNL92-M:KXB55-H
EAFUS IDNot Available
Dr. Duke IDPETUNIDIN-3-O-GLUCOSIDE|PETUNIDIN-3-O-BETA-D-GLUCOSIDE|PETUNIDIN-3-O-BETA-GLUCOSIDE|PETUNIDIN-3-GLUCOSIDE
BIGG IDNot Available
KNApSAcK IDC00006722
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 ID33
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.
— 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).