Vitisin A (YMDB01805)

Identification
YMDB IDYMDB01805
NameVitisin A
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionVitisin A belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. Vitisin A is an extremely weak basic (essentially neutral) compound (based on its pKa). Vitisin A may be a unique S. cerevisiae (yeast) metabolite.
Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
CAS number184362-09-2
WeightAverage: 561.4683
Monoisotopic: 561.124430508
InChI KeyDYYPRYJWENTOEN-DMRYIZGCSA-O
InChIInChI=1S/C26H24O14/c1-35-14-3-9(4-15(36-2)19(14)30)23-24(40-26-22(33)21(32)20(31)16(8-28)39-26)17-11(7-27)25(34)38-13-6-10(29)5-12(37-23)18(13)17/h3-7,16,20-22,26,28-33H,8H2,1-2H3/p+1/t16-,20-,21+,22-,26+/m1/s1
IUPAC Name6-formyl-11-hydroxy-3-(4-hydroxy-3,5-dimethoxyphenyl)-7-oxo-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,8-dioxatricyclo[7.3.1.0⁵,¹³]trideca-1(12),3,5,9(13),10-pentaen-2-ium
Traditional IUPAC Namevitisin A (pyranoanthocyanin)
Chemical FormulaC26H25O14
SMILES[H][O+]1C2=CC(O)=CC3=C2C(C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)=C1C1=CC(OC)=C(O)C(OC)=C1)=C(C=O)C(=O)O3
Chemical Taxonomy
Description belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid-3-O-glycosides
Alternative Parents
Substituents
  • Flavonoid-3-o-glycoside
  • 3p-methoxyflavonoid-skeleton
  • 4'-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Hexose monosaccharide
  • Coumarin
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • M-dimethoxybenzene
  • Dimethoxybenzene
  • Methoxyphenol
  • 1-benzopyran
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Pyranone
  • Alkyl aryl ether
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyran
  • Monocyclic benzene moiety
  • Monosaccharide
  • Benzenoid
  • Oxane
  • Heteroaromatic compound
  • Lactone
  • Secondary alcohol
  • Oxacycle
  • Ether
  • Acetal
  • Polyol
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Charge1
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.34 g/LALOGPS
logP1.66ALOGPS
logP-1.6ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)7.03ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area215.26 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity145.25 m³·mol⁻¹ChemAxon
Polarizability53.13 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
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 LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0100090000-da932d915ef34fe11e6cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1300090000-8d9b414708f8b12d7d9cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ow-7900010000-fbf34997ed7525f6e35cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1300090000-d4fb99a16ca30db7731aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-4600090000-5792278c1652761820c9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9400000000-6f677fab19df4c214df5JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound ID10325504
Kegg IDNot Available
ChemSpider IDNot Available
FOODB IDNot Available
Wikipedia IDVitisin A
BioCyc IDNot Available