Record Information
Version1.0
Creation date2010-04-08 22:13:00 UTC
Update date2019-11-26 03:14:37 UTC
Primary IDFDB017304
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePeonidin 3-arabinoside
Description3-Caffeoylpelargonidin 5-glucoside belongs to the class of organic compounds known as anthocyanidin-5-o-glycosides. These are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C5-position. 3-Caffeoylpelargonidin 5-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). 3-Caffeoylpelargonidin 5-glucoside has been detected, but not quantified in, root vegetables. This could make 3-caffeoylpelargonidin 5-glucoside a potential biomarker for the consumption of these foods.
CAS Number27214-74-0
Structure
Thumb
Synonyms
SynonymSource
Peonidin 3-O-arabinosideHMDB
Peonidin 3-arabinosidedb_source
Predicted Properties
PropertyValueSource
Water Solubility0.23 g/LALOGPS
logP1.62ALOGPS
logP1.09ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)6.4ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area162.21 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity114.78 m³·mol⁻¹ChemAxon
Polarizability42.34 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC21H21O10
IUPAC name3-{[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-1λ⁴-chromen-1-ylium
InChI IdentifierInChI=1S/C21H20O10/c1-28-15-4-9(2-3-12(15)24)20-16(30-21-19(27)18(26)17(8-22)31-21)7-11-13(25)5-10(23)6-14(11)29-20/h2-7,17-19,21-22,26-27H,8H2,1H3,(H2-,23,24,25)/p+1/t17-,18-,19+,21+/m1/s1
InChI KeyKGHFAKPGOXLHAB-BNDYYXHWSA-O
Isomeric SMILESCOC1=C(O)C=CC(=C1)C1=[O+]C2=C(C=C1O[C@H]1O[C@H](CO)[C@@H](O)[C@@H]1O)C(O)=CC(O)=C2
Average Molecular Weight433.3854
Monoisotopic Molecular Weight433.113471892
Classification
Description Belongs to the class of organic compounds known as anthocyanidin-5-o-glycosides. These are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C5-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentAnthocyanidin-5-O-glycosides
Alternative Parents
Substituents
  • Anthocyanidin-5-o-glycoside
  • Hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Anthocyanidin
  • Phenolic glycoside
  • Hexose monosaccharide
  • Hydroxycinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Cinnamic acid or derivatives
  • Cinnamic acid ester
  • O-glycosyl compound
  • Glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • Styrene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fatty acid ester
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Oxane
  • Benzenoid
  • Fatty acyl
  • Monocyclic benzene moiety
  • Monosaccharide
  • Heteroaromatic compound
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Secondary alcohol
  • Polyol
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Oxacycle
  • Acetal
  • Monocarboxylic acid or derivatives
  • Primary alcohol
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • 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-MSPeonidin 3-arabinoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ab9-9102300000-893dde17023067d7a924Spectrum
Predicted GC-MSPeonidin 3-arabinoside, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-053r-9100027000-6ff397fa9999eacbdb11Spectrum
Predicted GC-MSPeonidin 3-arabinoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPeonidin 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-f3eb131d2bbd24ae4ce6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-1300900000-bc416f1b2eeb1a9b0e07Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-015a-9611000000-e3e993b63fa8c97a9653Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1100900000-ede83ba8a94714f2ada1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1700900000-9045a35634f1fc338ecaSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f7o-8910000000-3d8cf540c38faf3e62f1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009700000-d52b8455e145570f8e89Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-1109600000-104e6038ba10b6f1331cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ug0-3094100000-7d46315b734928619c62Spectrum
NMRNot Available
ChemSpider ID30777234
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID55
DrugBank IDNot Available
HMDB IDHMDB38089
CRC / DFC (Dictionary of Food Compounds) IDCNL87-O:KXB26-Z
EAFUS IDNot Available
Dr. Duke IDPEONIDIN-3-ARABINOSIDE|PEONIDIN-3-O-ALPHA-L-ARABINOSIDE|PEONIDIN-3-O-ARABINOSIDE
BIGG IDNot Available
KNApSAcK IDC00006679
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 ID55
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).