Identification
YMDB IDYMDB01765
NamePeonidin
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPeonidin is an anthocyanin, which is a class of polyphenol. Anthocyanins are plant pigments found in many red berries including grape and grape skin. The cell wall of S. cerevisiae is permeable to anthocyanins and as a consequence the anthocyanins can be retained by yeast during wine-making; this adsorption can have an influence on wine color. Anthocyanins can react with yeast metabolites to form pyranoanthocyanins, which are more stable pigments formed during wine ageing and are of great importance for the color of aged wines. [PMID: 12822951] [PMID: 17303275]
Structure
Thumb
Synonyms
  • 3,4',5,7-Tetrahydroxy-3'-methoxyflavylium chloride
  • 3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-1-benzopyrylium chloride
  • Peonidin
CAS number134-01-0
WeightAverage: 301.2708
Monoisotopic: 301.071213148
InChI KeyXFDQJKDGGOEYPI-UHFFFAOYSA-O
InChIInChI=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
IUPAC Name3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-1λ⁴-chromen-1-ylium chloride
Traditional IUPAC Namepeonidin chloride
Chemical FormulaC16H13O6
SMILESCOC1=CC(=CC=C1O)C1=C(O)C=C2C(O)=CC(O)=CC2=[O+]1
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
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.024 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05gi-0974000000-00455f7cffd440fdee2aJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-00xr-1012090000-b83c67ee3325ce653d58JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0009000000-e93deeabbcfc80c1c4ecJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0009000000-e93deeabbcfc80c1c4ecJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0009000000-e93deeabbcfc80c1c4ecJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-2aed716a1d6f01124cbbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0009000000-2aed716a1d6f01124cbbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0009000000-2aed716a1d6f01124cbbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0029000000-6f7a0df69b6d344238deJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0089000000-5ec9215ab97dd96379a4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0un9-0190000000-19e0f032dd85566f8c1eJSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID75033
HMDB IDHMDB05797
Pubchem Compound ID441773
Kegg IDC08726
ChemSpider ID73580
FOODB IDFDB002753
Wikipedia IDPeonidin
BioCyc IDNot Available