Delphinidin (YMDB01664)

Identification
YMDB IDYMDB01664
NameDelphinidin
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionDelphinidin 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
MOLSDFPDBSMILESInChI
Synonyms
  • 3,3',4',5,5',7-Hexahydroxy-2-phenylbenzopyrylium chloride
  • 3,3',4',5,5',7-Hexahydroxyflavylium chloride
  • 3,5,7-Trihydroxy-2-(3,4,5-trihydroxyphenyl)benzopyrylium chloride
  • Delfinidol chloride
  • Delphinidin
  • Delphinidine
  • Delphinidol
  • Delfinidol
  • Ephdine
CAS number528-53-0
WeightAverage: 303.2436
Monoisotopic: 303.050477706
InChI KeyJKHRCGUTYDNCLE-UHFFFAOYSA-O
InChIInChI=1S/C15H10O7/c16-7-3-9(17)8-5-12(20)15(22-13(8)4-7)6-1-10(18)14(21)11(19)2-6/h1-5H,(H5-,16,17,18,19,20,21)/p+1
IUPAC Name3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium chloride
Traditional IUPAC Namedelphinidin chloride
Chemical FormulaC15H11O7
SMILESOC1=CC(O)=C2C=C(O)C(=[O+]C2=C1)C1=CC(O)=C(O)C(O)=C1
Chemical Taxonomy
Description belongs to the class of organic compounds known as 7-hydroxyflavonoids. These are flavonoids that bear one hydroxyl group at the C-7 position of the flavonoid skeleton.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassHydroxyflavonoids
Direct Parent7-hydroxyflavonoids
Alternative Parents
Substituents
  • 3'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Anthocyanidin
  • Benzopyran
  • 1-benzopyran
  • Resorcinol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Phenoxide
  • Monocyclic benzene moiety
  • Benzenoid
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Organic oxide
  • Organooxygen compound
  • Hydrochloride
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic zwitterion
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateLiquid
Charge0
Melting point>350 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.071 g/LALOGPS
logP2.07ALOGPS
logP2.77ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)5.98ChemAxon
pKa (Strongest Basic)-5.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area134.52 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity86.09 m³·mol⁻¹ChemAxon
Polarizability29.04 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, Positivesplash10-05g0-0953000000-f1e05db277a035a88796JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-002b-2023095000-1abfbd97905ef56e5c90JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0009000000-9e7f8a6aeadfcb1e8777JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002r-0189000000-d7b571c1552a0fc9910eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0v4i-8940000000-1cd702cb5aa5fd0a3386JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-3705d9b5195a60ce42f0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0129000000-07a84d244d24957a2c59JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06fr-1893000000-ec65d8de6af5dc5d0d3fJSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID28436
HMDB IDHMDB03074
Pubchem Compound ID68245
Kegg IDC05908
ChemSpider ID24808102
FOODB IDFDB002613
Wikipedia IDDelphinidin
BioCyc IDNot Available