Record Information
Version 1.0
Update Date 1/22/2018 12:54:53 PM
Metabolite IDPAMDB000092
Identification
Name: Oxalacetic acid
Description:Oxaloacetic acid, also known as oxosuccinic acid or oxalacetic acid, is a four-carbon dicarboxylic acid appearing as an intermediate of the citric acid cycle. In vivo, oxaloacetate (the ionized form of oxaloacetic acid) is formed by the oxidation of L-malate, catalyzed by malate dehydrogenase, and reacts with Acetyl-CoA to form citrate, catalyzed by citrate synthase.(wikipedia) A class of ketodicarboxylic acids derived from oxalic acid. Oxaloacetic acid is an intermediate in the citric acid cycle and is converted to aspartic acidD by a transamination reaction.
Structure
Thumb
Synonyms:
  • 2-Ketosuccinate
  • 2-Ketosuccinic acid
  • 2-Oxobutanedioate
  • 2-Oxobutanedioic acid
  • 2-Oxosuccinate
  • 2-Oxosuccinic acid
  • A-Ketosuccinate
  • A-Ketosuccinic acid
  • Alpha-Ketosuccinate
  • Alpha-Ketosuccinic acid
  • Keto-oxaloacetate
  • Keto-oxaloacetic acid
  • Ketosuccinate
  • Ketosuccinic acid
  • OAA
  • Oxalacetate
  • Oxalacetic acid
  • Oxaloacetate
  • Oxaloacetic acid
  • Oxaloethanoate
  • Oxaloethanoic acid
  • Oxosuccinate
  • Oxosuccinic acid
  • α-Ketosuccinate
  • α-Ketosuccinic acid
Chemical Formula: C4H4O5
Average Molecular Weight: 132.0716
Monoisotopic Molecular Weight: 132.005873238
InChI Key: KHPXUQMNIQBQEV-UHFFFAOYSA-N
InChI:InChI=1S/C4H4O5/c5-2(4(8)9)1-3(6)7/h1H2,(H,6,7)(H,8,9)
CAS number: 328-42-7
IUPAC Name:2-oxobutanedioic acid
Traditional IUPAC Name: oxalacetate
SMILES:OC(=O)CC(=O)C(O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.
Kingdom Organic compounds
Super ClassOrganic acids and derivatives
Class Keto acids and derivatives
Sub ClassShort-chain keto acids and derivatives
Direct Parent Short-chain keto acids and derivatives
Alternative Parents
Substituents
  • Short-chain keto acid
  • Beta-keto acid
  • 1,3-dicarbonyl compound
  • Dicarboxylic acid or derivatives
  • Beta-hydroxy ketone
  • Alpha-keto acid
  • Alpha-hydroxy ketone
  • Ketone
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-2
Melting point: 161 °C
Experimental Properties:
PropertyValueSource
Water Solubility:134 mg/mL [HMP experimental]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility57.1 mg/mLALOGPS
logP-0.68ALOGPS
logP-0.042ChemAxon
logS-0.36ALOGPS
pKa (Strongest Acidic)2.41ChemAxon
pKa (Strongest Basic)-9.9ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area91.67 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity24.33 m3·mol-1ChemAxon
Polarizability10.06 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-00dr-4900000000-9d943d40beaca3c602a1View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)splash10-007a-9210000000-020f60717e2ea79d1ccdView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)splash10-000b-9540000000-a53f674cc98960834f88View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)splash10-001a-8940000000-40b790e06141d7180938View in MoNA
GC-MSGC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-000i-9000000000-0be675f3aa3e973393b7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-000f-9000000000-4fba97fcd7b0f2215f75View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0006-9000000000-9b1f4171aee6283a3cbdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-3900000000-6f4e965a3f513bf8db13View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9600000000-8ae7abf60057088e14dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01bc-9100000000-5724c215c46a4f568140View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0019-8900000000-829898d0849b1fbf1c28View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9100000000-5a5ff8fb7cb52eebf0c8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-657d1384d478ddc33b6dView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-f371299a07d43c23ff1dView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Allen RH, Stabler SP, Savage DG, Lindenbaum J: Elevation of 2-methylcitric acid I and II levels in serum, urine, and cerebrospinal fluid of patients with cobalamin deficiency. Metabolism. 1993 Aug;42(8):978-88. Pubmed: 8345822
  • Dworzak E, Grunicke H, Berger H, Jarosch E, Haas H, Hopfel I: [Pyruvate dehydrogenase deficiency in a child with persistent lactic acidosis] J Clin Chem Clin Biochem. 1985 Jun;23(6):323-9. Pubmed: 3926941
  • Efimov AS, Gulyi MF, Shcherbak AV, Dzvonkevich ND: [Levels of Krebs cycle metabolites in the blood and urine of patients with diabetes mellitus] Probl Endokrinol (Mosk). 1983 Mar-Apr;29(2):10-4. Pubmed: 6856592
  • el-Sharabasy MM: Observations on calcium oxalate stone formers. Br J Urol. 1992 Nov;70(5):474-7. Pubmed: 1361403
  • Esenmo E, Chandramouli V, Schumann WC, Kumaran K, Wahren J, Landau BR: Use of 14CO2 in estimating rates of hepatic gluconeogenesis. Am J Physiol. 1992 Jul;263(1 Pt 1):E36-41. Pubmed: 1322046
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Koike K, Koike M: Fluorescent analysis of alpha-keto acids in serum and urine by high-performance liquid chromatography. Anal Biochem. 1984 Sep;141(2):481-7. Pubmed: 6437276
  • Olubuyide IO, Festing MF, Chapman C, Higginson J, Whicher JT: Discriminant analysis of biochemical parameters in liver disease. Trop Gastroenterol. 1997 Jan-Mar;18(1):15-9. Pubmed: 9197166
  • Peng, L., Arauzo-Bravo, M. J., Shimizu, K. (2004). "Metabolic flux analysis for a ppc mutant Escherichia coli based on 13C-labelling experiments together with enzyme activity assays and intracellular metabolite measurements." FEMS Microbiol Lett 235:17-23. Pubmed: 15158257
  • Petrarulo M, Facchini P, Cerelli E, Marangella M, Linari F: Citrate in urine determined with a new citrate lyase method. Clin Chem. 1995 Oct;41(10):1518-21. Pubmed: 7586527
  • Rabinovich PD, Miliushkin PV: [Content of biological oxidation metabolites in the blood and urine of peptic ulcer patients] Vopr Med Khim. 1979 Nov-Dec;25(6):755-8. Pubmed: 516538
  • Schauenstein E, Kronberger L, Schaur RJ, Fink E, Georgiopulos E: [Malate and oxaloacetate levels in whole blood of patients with and without malignant tumor diseases] Wien Klin Wochenschr. 1973 Jun 29;85(26):478-82. Pubmed: 4717666
  • Sperl W, Maurer H, Dworschak E, Hopfel I, Hammerer I: [Lactic acid acidosis with mitochondrial myopathy due to a pyruvate dehydrogenase deficiency] Padiatr Padol. 1985;20(1):55-67. Pubmed: 3919358
  • Sweatman BC, Farrant RD, Holmes E, Ghauri FY, Nicholson JK, Lindon JC: 600 MHz 1H-NMR spectroscopy of human cerebrospinal fluid: effects of sample manipulation and assignment of resonances. J Pharm Biomed Anal. 1993 Aug;11(8):651-64. Pubmed: 8257730
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
  • Wong LT, Davidson AG, Applegarth DA, Dimmick JE, Norman MG, Toone JR, Pirie G, Wong J: Biochemical and histologic pathology in an infant with cross-reacting material (negative) pyruvate carboxylase deficiency. Pediatr Res. 1986 Mar;20(3):274-9. Pubmed: 3085060
  • Zupke C, Sinskey AJ, Stephanopoulos G: Intracellular flux analysis applied to the effect of dissolved oxygen on hybridomas. Appl Microbiol Biotechnol. 1995 Dec;44(1-2):27-36. Pubmed: 8579834
Synthesis Reference: Heidelberger, Charles; Hurlbert, Robert B. The synthesis of oxalacetic acid-I-C14 and orotic acid-6-C14. Journal of the American Chemical Society (1950), 72 4704-6.
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID16452
HMDB IDHMDB00223
Pubchem Compound ID970
Kegg IDC00036
ChemSpider ID945
WikipediaOxalacetic acid
BioCyc IDOXALACETIC_ACID
EcoCyc IDOXALACETIC_ACID
Ligand ExpoOAA