Showing metabocard for Peonidin (BMDB0005797)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:18:39 UTC
Update Date2020-04-22 15:16:21 UTC
BMDB IDBMDB0005797
Secondary Accession Numbers
  • BMDB05797
Metabolite Identification
Common NamePeonidin
Description3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-1λ⁴-chromen-1-ylium, also known as 3,4',5,7-tetrahydroxy-3'-methoxyflavylium chloride or peonidin, 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. 3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-1λ⁴-chromen-1-ylium is an extremely weak basic (essentially neutral) compound (based on its pKa). 3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-1λ⁴-chromen-1-ylium exists in all eukaryotes, ranging from yeast to humans.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3,4',5,7-Tetrahydroxy-3'-methoxyflavylium chlorideChEBI
3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-1-benzopyrylium chlorideChEBI
PeonidinChEBI
Chemical FormulaC16H13ClO6
Average Molecular Weight336.724
Monoisotopic Molecular Weight336.040065855
IUPAC Name3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-1λ⁴-chromen-1-ylium chloride
Traditional Namepeonidin chloride
CAS Registry Number134-01-0
SMILES
[Cl-].COC1=C(O)C=CC(=C1)C1=[O+]C2=CC(O)=CC(O)=C2C=C1O
InChI Identifier
InChI=1S/C16H12O6.ClH/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);1H
InChI KeyOGBSHLKSHNAPEW-UHFFFAOYSA-N
Chemical Taxonomy
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-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Organic salt
  • Organic chloride salt
  • Organic oxygen compound
  • Organooxygen compound
  • Organic zwitterion
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.61ALOGPS
logP3.08ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)6.01ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area103.29 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity88.6 m³·mol⁻¹ChemAxon
Polarizability30.15 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05gi-0974000000-00455f7cffd440fdee2aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-00xr-1012090000-b83c67ee3325ce653d58View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0009000000-e93deeabbcfc80c1c4ecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0009000000-e93deeabbcfc80c1c4ecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0009000000-e93deeabbcfc80c1c4ecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-2aed716a1d6f01124cbbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0009000000-2aed716a1d6f01124cbbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0009000000-2aed716a1d6f01124cbbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0029000000-6f7a0df69b6d344238deView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0089000000-5ec9215ab97dd96379a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0un9-0190000000-19e0f032dd85566f8c1eView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0125117
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB002753
KNApSAcK IDNot Available
Chemspider ID144246
KEGG Compound IDC08726
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPeonidin
METLIN IDNot Available
PubChem Compound164544
PDB IDNot Available
ChEBI ID75033
References
Synthesis ReferenceLu, Ting Sen; Saito, Norio; Yokoi, Masato; Shigihara, Atsushi; Honda, Toshio. An acylated peonidin glycoside in the violet-blue flowers of Pharbitis nil. Phytochemistry (1991), 30(7), 2387-90.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available