2-Dehydro-D-gluconate (YMDB01582)

Identification
YMDB IDYMDB01582
Name2-Dehydro-D-gluconate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description2-Dehydro-D-gluconate, also known as 2-ketogluconate or 2-ketolactonic acid, belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group. 2-Dehydro-D-gluconate is an extremely weak basic (essentially neutral) compound (based on its pKa). 2-Dehydro-D-gluconate may be a unique S. cerevisiae (yeast) metabolite.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 2-Dehydro-D-gluconate 6-phosphate
  • 6-O-phosphono-D-fructosonic acid
  • 6-Phospho-2-dehydro-D-gluconate
  • 2-Ketogluconate
  • 2-Ketolactonate
  • 2-Ketogluconic acid
  • 2-Ketolactonic acid
  • 2-Dehydro-D-gluconic acid
CAS numberNot Available
WeightAverage: 193.1315
Monoisotopic: 193.034827642
InChI KeyVBUYCZFBVCCYFD-JJYYJPOSSA-M
InChIInChI=1S/C6H10O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-4,7-10H,1H2,(H,12,13)/p-1/t2-,3-,4+/m1/s1
IUPAC Name(3S,4R,5R)-3,4,5,6-tetrahydroxy-2-oxohexanoate
Traditional IUPAC Name2-dehydro-D-gluconate
Chemical FormulaC6H9O7
SMILESOC[C@@H](O)[C@@H](O)[C@H](O)C(=O)C([O-])=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentSugar acids and derivatives
Alternative Parents
Substituents
  • Hexose monosaccharide
  • Medium-chain keto acid
  • Beta-hydroxy acid
  • Sugar acid
  • Acyloin
  • Alpha-keto acid
  • Beta-hydroxy ketone
  • Hydroxy acid
  • Keto acid
  • Monosaccharide
  • Alpha-hydroxy ketone
  • Ketone
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Primary alcohol
  • Organic anion
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge-1
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility363 g/LALOGPS
logP-2ALOGPS
logP-2.5ChemAxon
logS0.24ALOGPS
pKa (Strongest Acidic)2.67ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area138.12 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity48.49 m³·mol⁻¹ChemAxon
Polarizability16.06 ųChemAxon
Number of Rings0ChemAxon
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 LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-2900000000-064d72b894a1f88dd80fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9700000000-b7e8741254e9c35fa16cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9100000000-4da7158dbe086d4551faJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-7900000000-7ee7af0d6eb26815c538JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ckl-9500000000-4c3f8fc5e9b8926e6615JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0btl-9100000000-80fca0fc269df4681d30JSpectraViewer
References
References:
  • Boer, V. M., Crutchfield, C. A., Bradley, P. H., Botstein, D., Rabinowitz, J. D. (2010). "Growth-limiting intracellular metabolites in yeast growing under diverse nutrient limitations." Mol Biol Cell 21:198-211.19889834
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID2229
HMDB IDNot Available
Pubchem Compound ID37
Kegg IDC01218
ChemSpider ID21864901
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available