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Identification
YMDB IDYMDB00059
Name2-hydroxyglutaric acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description2-Hydroxyglutarate belongs to the class of organic compounds known as short-chain hydroxy acids and derivatives. These are hydroxy acids with an alkyl chain the contains less than 6 carbon atoms. 2-Hydroxyglutarate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 2-Hydroxyglutarate exists in all living species, ranging from bacteria to humans. 2-Hydroxyglutarate is a potentially toxic compound.
Structure
Thumb
Synonyms
  • (R)-2-hydroxy-Pentanedioate
  • (R)-2-hydroxy-Pentanedioic acid
  • (R)-2-Hydroxyglutarate
  • (R)-2-Hydroxyglutaric acid
  • (R)-2-hydroxypentanedioic acid
  • (R)-a-Hydroxyglutarate
  • (R)-a-Hydroxyglutaric acid
  • (R)-alpha-Hydroxyglutarate
  • (R)-alpha-Hydroxyglutaric acid
  • (R)-Hydroxyglutarate
  • 2-hydroxy-D-Glutarate
  • 2-hydroxy-D-Glutaric acid
  • 2-hydroxy-delta-Glutarate
  • 2-hydroxy-delta-Glutaric acid
  • D-2-Hydroxyglutarate
  • D-2-Hydroxyglutaric acid
  • D-a-Hydroxyglutarate
  • D-a-Hydroxyglutaric acid
  • delta-2-Hydroxyglutarate
  • delta-2-Hydroxyglutaric acid
  • delta-alpha-Hydroxyglutarate
  • delta-alpha-Hydroxyglutaric acid
  • R-2-HYDROXYGLUTARATE
  • alpha-Hydroxyglutaric acid
  • alpha-Hydroxyglutarate
  • a-Hydroxyglutarate
  • a-Hydroxyglutaric acid
  • Α-hydroxyglutarate
  • Α-hydroxyglutaric acid
  • 2-Hydroxyglutaric acid
  • alpha-Hydroxyglutarate, (D)-isomer
  • alpha-Hydroxyglutarate, (DL)-isomer
  • alpha-Hydroxyglutarate, (L)-isomer
  • alpha-Hydroxyglutarate, disodium salt
  • (±)-2-hydroxyglutaric acid
  • 2,3-Dideoxypentaric acid
  • 2-Hydroxypentanedioic acid
  • DL-2-Hydroxyglutaric acid
  • 2-Hydroxyglutarate
CAS number2889-31-8
WeightAverage: 148.114
Monoisotopic: 148.037173366
InChI KeyHWXBTNAVRSUOJR-UHFFFAOYSA-N
InChIInChI=1S/C5H8O5/c6-3(5(9)10)1-2-4(7)8/h3,6H,1-2H2,(H,7,8)(H,9,10)
IUPAC Name2-hydroxypentanedioic acid
Traditional IUPAC Name2-hydroxyglutaric acid
Chemical FormulaC5H8O5
SMILES[H]OC(=O)C([H])([H])C([H])([H])C([H])(O[H])C(=O)O[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as short-chain hydroxy acids and derivatives. These are hydroxy acids with an alkyl chain the contains less than 6 carbon atoms.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassShort-chain hydroxy acids and derivatives
Direct ParentShort-chain hydroxy acids and derivatives
Alternative Parents
Substituents
  • Short-chain hydroxy acid
  • Fatty acid
  • Monosaccharide
  • Dicarboxylic acid or derivatives
  • Alpha-hydroxy acid
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point>300 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility157 g/LALOGPS
logP-1ALOGPS
logP-0.82ChemAxon
logS0.03ALOGPS
pKa (Strongest Acidic)3.28ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity29.63 m³·mol⁻¹ChemAxon
Polarizability12.97 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 GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uel-9300000000-fbe125fbbc3b5bc0783bJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00gv-8191000000-f6fdffd87ffe1acf65b4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-2900000000-4a286f23e047b386c273JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0lz0-9600000000-6b6214d1086f381022a0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-9100000000-02ce88ad8bf7c4b7f22aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002b-2900000000-6750865d94d1d2564b29JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zi9-8900000000-8cdd78454ba0d2069b3eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9100000000-1ef9312d29d127c85bf8JSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Albers, E., Gustafsson, L., Niklasson, C., Liden, G. (1998). "Distribution of 14C-labelled carbon from glucose and glutamate during anaerobic growth of Saccharomyces cerevisiae." Microbiology 144 ( Pt 6):1683-1690.9639938
  • Castrillo, J. I., Zeef, L. A., Hoyle, D. C., Zhang, N., Hayes, A., Gardner, D. C., Cornell, M. J., Petty, J., Hakes, L., Wardleworth, L., Rash, B., Brown, M., Dunn, W. B., Broadhurst, D., O'Donoghue, K., Hester, S. S., Dunkley, T. P., Hart, S. R., Swainston, N., Li, P., Gaskell, S. J., Paton, N. W., Lilley, K. S., Kell, D. B., Oliver, S. G. (2007). "Growth control of the eukaryote cell: a systems biology study in yeast." J Biol 6:4.17439666
Synthesis Reference:Kobayashi, Hidehiko; Yamaguchi, Koretaka; Yamashita, Takeshi. a-Hydroxyglutaric acid from glutamic acid. Jpn. Tokkyo Koho (1968), 3 pp.
External Links:
ResourceLink
CHEBI ID32796
HMDB IDHMDB00606
Pubchem Compound ID43
Kegg IDC01087
ChemSpider ID42
FOODB IDNot Available
WikipediaAlpha-Hydroxyglutaric_acid
BioCyc IDNot Available

Enzymes

General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
3-phospho-D-glycerate + NAD(+) = 3- phosphonooxypyruvate + NADH
Gene Name:
SER33
Uniprot ID:
P40510
Molecular weight:
51187.80078
Reactions
3-phospho-D-glycerate + NAD(+) → 3-phosphonooxypyruvate + NADH.
2-hydroxyglutarate + NAD(+) → 2-oxoglutarate + NADH.
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
3-phospho-D-glycerate + NAD(+) = 3- phosphonooxypyruvate + NADH
Gene Name:
SER3
Uniprot ID:
P40054
Molecular weight:
51192.80078
Reactions
3-phospho-D-glycerate + NAD(+) → 3-phosphonooxypyruvate + NADH.
2-hydroxyglutarate + NAD(+) → 2-oxoglutarate + NADH.