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Showing Compound Peonidin 3-[4-hydroxycinnamoyl-b-D-glucopyranoside] (FDB017306)

Record Information
Version1.0
Creation date2010-04-08 22:13:00 UTC
Update date2019-11-26 03:14:37 UTC
Primary IDFDB017306
Secondary Accession Numbers
  • FDB017309
  • FDB002753
Chemical Information
FooDB NamePeonidin 3-[4-hydroxycinnamoyl-b-D-glucopyranoside]
DescriptionPeonidin 3-[4-hydroxycinnamoyl-b-D-glucopyranoside], also known as 3,4',5,7-tetrahydroxy-3'-methoxyflavylium or peonidin cation, belongs to the class of organic compounds known as 3'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C3' atom of the flavonoid backbone. Thus, peonidin 3-[4-hydroxycinnamoyl-b-D-glucopyranoside] is considered to be a flavonoid lipid molecule. Peonidin 3-[4-hydroxycinnamoyl-b-D-glucopyranoside] is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Peonidin 3-[4-hydroxycinnamoyl-b-D-glucopyranoside] has been detected, but not quantified in, several different foods, such as common grapes, fruits, olives, rose hips, and sweet oranges. This could make peonidin 3-[4-hydroxycinnamoyl-b-D-glucopyranoside] a potential biomarker for the consumption of these foods.
CAS Number134-01-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.024 g/LALOGPS
logP1.9ALOGPS
logP3.08ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)6.01ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area103.29 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity88.6 m³·mol⁻¹ChemAxon
Polarizability30.14 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC16H13O6
IUPAC name3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-1lambda4-chromen-1-ylium
InChI IdentifierInChI=1S/C16H12O6/c1-21-15-4-8(2-3-11(15)18)16-13(20)7-10-12(19)5-9(17)6-14(10)22-16/h2-7H,1H3,(H3-,17,18,19,20)/p+1
InChI KeyXFDQJKDGGOEYPI-UHFFFAOYSA-O
Isomeric SMILESCOC1=C(O)C=CC(=C1)C1=[O+]C2=CC(O)=CC(O)=C2C=C1O
Average Molecular Weight301.2708
Monoisotopic Molecular Weight301.071213148
Classification
Description Belongs to the class of organic compounds known as 3'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C3' atom of the flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassO-methylated flavonoids
Direct Parent3'-O-methylated flavonoids
Alternative Parents
Substituents
  • 3p-methoxyflavonoid-skeleton
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Anthocyanidin
  • Benzopyran
  • Methoxyphenol
  • 1-benzopyran
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Polyol
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSPeonidin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fk9-0691000000-84b3d0e544b6a7a62296Spectrum
Predicted GC-MSPeonidin, TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00xr-1012090000-b83c67ee3325ce653d58Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT 21V, positivesplash10-0udi-0029000000-7965142f0e637a01a39d2020-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT 21V, positivesplash10-000i-0090000000-e5f1890c4c1ee032ffa82020-07-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-593a90502ef88db9b6ec2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udr-0097000000-089b2aa92da11eab883d2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-1970000000-dc287a8cd231867d44dc2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-1e7e6fcb1bde542bcd8a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0029000000-ea86521c274e006e6dd42016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-4950000000-5caf71b895882a8dcfbe2016-08-03View Spectrum
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 IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDCNL87-O:KXB29-C
EAFUS IDNot Available
Dr. Duke IDPEONIDIN-3-P-COUMAROYL-GLUCOSIDE
BIGG IDNot Available
KNApSAcK IDC00006861
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 IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
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.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).