Record Information
Version1.0
Creation date2010-04-08 22:13:01 UTC
Update date2019-11-26 03:14:38 UTC
Primary IDFDB017314
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePetunidin 3-arabinoside
DescriptionPetunidin 3-arabinoside belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. Petunidin 3-arabinoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Petunidin 3-arabinoside is found, on average, in the highest concentration in a few different foods, such as bilberries, highbush blueberries, and lowbush blueberries and in a lower concentration in . Petunidin 3-arabinoside has also been detected, but not quantified in, several different foods, such as fruits, sweet cherries, red raspberries, black chokeberries, and strawberries. This could make petunidin 3-arabinoside a potential biomarker for the consumption of these foods.
CAS Number28500-03-0
Structure
Thumb
Synonyms
SynonymSource
Petunidin 3-arabinosidedb_source
Predicted Properties
PropertyValueSource
Water Solubility0.27 g/LALOGPS
logP1.2ALOGPS
logP1.09ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)7.35ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area162.21 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity114.78 m³·mol⁻¹ChemAxon
Polarizability42.47 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC21H21O10
IUPAC name2-(3,4-dihydroxy-5-methoxyphenyl)-7-hydroxy-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]-1λ⁴-chromen-1-ylium
InChI IdentifierInChI=1S/C21H20O10/c1-28-15-6-10(4-12(23)17(15)25)20-16(5-9-2-3-11(22)7-14(9)30-20)31-21-19(27)18(26)13(24)8-29-21/h2-7,13,18-19,21,24,26-27H,8H2,1H3,(H2-,22,23,25)/p+1
InChI KeyMVBYJYWJFIOZIW-UHFFFAOYSA-O
Isomeric SMILESCOC1=CC(=CC(O)=C1O)C1=C(OC2OCC(O)C(O)C2O)C=C2C=CC(O)=CC2=[O+]1
Average Molecular Weight433.3854
Monoisotopic Molecular Weight433.113471892
Classification
Description Belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid-3-O-glycosides
Alternative Parents
Substituents
  • Flavonoid-3-o-glycoside
  • 3p-methoxyflavonoid-skeleton
  • 3'-hydroxyflavonoid
  • Hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • Anthocyanidin
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • Methoxyphenol
  • 1-benzopyran
  • Anisole
  • Phenoxy compound
  • Catechol
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Oxane
  • Monosaccharide
  • Monocyclic benzene moiety
  • Benzenoid
  • Heteroaromatic compound
  • Secondary alcohol
  • Organoheterocyclic compound
  • Acetal
  • Oxacycle
  • Ether
  • Polyol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Organooxygen 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 stateNot Available
Physical DescriptionNot Available
Mass CompositionC 58.20%; H 4.88%; O 36.92%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-arabinoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0pb9-9107500000-3f53a69ba31a9a645561Spectrum
Predicted GC-MSPetunidin 3-arabinoside, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-2610129000-64fd8d887fb84c61cc21Spectrum
Predicted GC-MSPetunidin 3-arabinoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPetunidin 3-arabinoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0100900000-ba1121d4aac43a413fc4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0400900000-af50065756fb09fb941bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00yi-9712000000-849f4b8150b3ba5db3a5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1200900000-c1afc02632505176d91cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-4600900000-18939e2dd9c9294dea80Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-9af1e6c668f6c0047b67Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0005900000-d605a7e035cf3d700b20Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0159100000-5f303f95a3b1bcdaff6fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0300-2591000000-a55808c1b3f7956c2944Spectrum
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 ID35
DrugBank IDNot Available
HMDB IDHMDB38094
CRC / DFC (Dictionary of Food Compounds) IDCNL92-M:KXB50-C
EAFUS IDNot Available
Dr. Duke IDPETUNIDIN-3-O-ARABINOSIDE|PETUNIDIN-3-O-ALPHA-L-ARABINOSIDE
BIGG IDNot Available
KNApSAcK IDC00006720
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 ID35
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).