2-Oxaloglutaric acid (YMDB00705)

Identification
YMDB IDYMDB00705
Name2-Oxaloglutaric acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description2-Oxaloglutaric acid, also known as oxaloglutarate, belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. 2-Oxaloglutaric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 2-Oxaloglutaric acid exists in both E. coli (prokaryote) and yeast (eukaryote).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • Oxaloglutarate
  • Oxaloglutaric acid
  • 2-Oxaloglutarate
CAS numberNot Available
WeightAverage: 204.1342
Monoisotopic: 204.02700261
InChI KeyPYOHERBGXSPHQI-UHFFFAOYSA-N
InChIInChI=1S/C7H8O7/c8-4(9)2-1-3(6(11)12)5(10)7(13)14/h3H,1-2H2,(H,8,9)(H,11,12)(H,13,14)
IUPAC Name1-oxobutane-1,2,4-tricarboxylic acid
Traditional IUPAC Nameoxaloglutarate
Chemical FormulaC7H8O7
SMILESOC(=O)CCC(C(O)=O)C(=O)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassTricarboxylic acids and derivatives
Direct ParentTricarboxylic acids and derivatives
Alternative Parents
Substituents
  • Tricarboxylic acid or derivatives
  • Beta-keto acid
  • 1,3-dicarbonyl compound
  • Keto acid
  • Beta-hydroxy ketone
  • Alpha-keto acid
  • Alpha-hydroxy ketone
  • Ketone
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility9.44 g/LALOGPS
logP-0.6ALOGPS
logP0.07ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)2.5ChemAxon
pKa (Strongest Basic)-9.9ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area128.97 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity39.78 m³·mol⁻¹ChemAxon
Polarizability16.91 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • mitochondrion
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG Pathways
Lysine biosynthesisec00300 Map00300
SMPDB ReactionsNot Available
KEGG Reactions
NAD + Homoisocitric acid ↔ NADH + 2-Oxaloglutaric acid + hydron
2-Oxaloglutaric acid + hydron ↔ Carbon dioxide + Oxoadipic acid
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0c03-6900000000-d86c317933f5bd781679JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4u-0910000000-efba0005b7c6e412f344JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08g3-2900000000-ab173b2f9284d0cb1bafJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dr-7900000000-35ed96e108165b56f426JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pb9-0930000000-550e5c2f1729955561e2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0cdi-1900000000-01ebded92601f1a204f6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0229-9600000000-ef3f2ef215789bcc63c9JSpectraViewer
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Zabriskie, T. M., Jackson, M. D. (2000). "Lysine biosynthesis and metabolism in fungi." Nat Prod Rep 17:85-97.10714900
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID7814
HMDB IDNot Available
Pubchem Compound ID440718
Kegg IDC05533
ChemSpider ID389591
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Homoisocitrate dehydrogenase, mitochondrial
General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the NAD(+)-dependent conversion of homoisocitrate to alpha-ketoadipate
Gene Name:
LYS12
Uniprot ID:
P40495
Molecular weight:
40068.60156
Reactions
(1R,2S)-1-hydroxybutane-1,2,4-tricarboxylate + NAD(+) → 2-oxoadipate + CO(2) + NADH.