Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:08:06 UTC
HMDB IDHMDB00223
Secondary Accession NumbersNone
Metabolite Identification
Common NameOxalacetic acid
DescriptionOxaloacetic 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
  1. 2-Ketosuccinate
  2. 2-Ketosuccinic acid
  3. 2-Oxobutanedioate
  4. 2-Oxobutanedioic acid
  5. 2-Oxosuccinate
  6. 2-Oxosuccinic acid
  7. a-Ketosuccinate
  8. a-Ketosuccinic acid
  9. alpha-Ketosuccinate
  10. alpha-Ketosuccinic acid
  11. Ketosuccinate
  12. Ketosuccinic acid
  13. OAA
  14. Oxalacetate
  15. Oxaloacetate
  16. Oxaloacetic acid
  17. Oxaloethanoate
  18. Oxaloethanoic acid
  19. Oxosuccinate
  20. Oxosuccinic acid
Chemical FormulaC4H4O5
Average Molecular Weight132.0716
Monoisotopic Molecular Weight132.005873238
IUPAC Name2-oxobutanedioic acid
Traditional IUPAC Nameoxaloacetic acid
CAS Registry Number328-42-7
SMILES
OC(=O)CC(=O)C(O)=O
InChI Identifier
InChI=1S/C4H4O5/c5-2(4(8)9)1-3(6)7/h1H2,(H,6,7)(H,8,9)
InChI KeyKHPXUQMNIQBQEV-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassOrganic Acids and Derivatives
ClassCarboxylic Acids and Derivatives
Sub ClassDicarboxylic Acids and Derivatives
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Alpha Keto-Acids and Derivatives
  • Beta Keto-Acids and Derivatives
  • Dicarboxylic acids(Lipidmaps)
  • Fatty Acids and Conjugates
  • Short-chain Keto Acids and Derivatives
  • oxo dicarboxylic acid(ChEBI)
Substituents
  • Carboxylic Acid
  • Ketone
Direct ParentDicarboxylic Acids and Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Alanine and aspartate metabolism
  • Component of Arginine and proline metabolism
  • Component of Cysteine metabolism
  • Component of Glutamate metabolism
  • Component of Glyoxylate and dicarboxylate metabolism
  • Component of Novobiocin biosynthesis
  • Component of Phenylalanine metabolism
  • Component of Phenylalanine, tyrosine and tryptophan biosynthesis
  • Component of Pyruvate metabolism
  • Component of Tyrosine metabolism
ApplicationNot Available
Cellular locations
  • Mitochondria
  • Peroxisome
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point161 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility134 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility57.1 g/LALOGPS
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 area91.67ChemAxon
rotatable bond count3ChemAxon
refractivity24.33ChemAxon
polarizability10.06ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Mitochondria
  • Peroxisome
Biofluid Locations
  • Cellular Cytoplasm
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Liver
Pathways
NameSMPDB LinkKEGG Link
Alanine MetabolismSMP00055map00250
Aspartate MetabolismSMP00067map00250
Citric Acid CycleSMP00057map00020
GluconeogenesisSMP00128map00010
Malate-Aspartate ShuttleSMP00129Not Available
Pyruvate MetabolismSMP00060map00620
Transfer of Acetyl Groups into MitochondriaSMP00466Not Available
Urea CycleSMP00059map00330
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
Cellular CytoplasmDetected and Quantified61 uMAdult (>18 years old)BothNormal
Cerebrospinal Fluid (CSF)Detected and Quantified7.3 (6.1-8.3) uMAdult (>18 years old)BothNormal
  • Geigy Scient...
Cerebrospinal Fluid (CSF)Detected and Quantified27 +/- 15 uMNot SpecifiedBothNormal
UrineDetected and Quantified2.2 (1.16-5.94) umol/mmol creatinineAdult (>18 years old)FemaleNormal
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)MaleCommentNormal
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)MaleCommentNormal
UrineDetected and Quantified2.27 (0.51-4.48) umol/mmol creatinineAdult (>18 years old)MaleNormal
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReference
Cellular CytoplasmDetected and Quantified2 uMAdult (>18 years old)BothAnoxia
Associated Disorders and Diseases
Disease References
Anoxia
  • 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
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB001479
KNApSAcK IDC00001197
Chemspider ID945
KEGG Compound IDC00036
BioCyc IDOXALACETIC_ACID
BiGG ID33604
Wikipedia LinkOxalacetic acid
NuGOwiki LinkHMDB00223
Metagene LinkHMDB00223
METLIN ID123
PubChem Compound970
PDB IDNot Available
ChEBI ID30744
References
Synthesis ReferenceHeidelberger, 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
General References
  1. 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
  2. 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
  3. 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
  4. el-Sharabasy MM: Observations on calcium oxalate stone formers. Br J Urol. 1992 Nov;70(5):474-7. Pubmed: 1361403
  5. 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
  6. 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
  7. 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
  8. 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
  9. 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
  10. 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
  11. 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
  12. 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
  13. 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
  14. 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

Enzymes

Gene Name:
ACLY
Uniprot ID:
P53396
Reactions
ADP + Phosphoric acid + Acetyl-CoA + Oxalacetic acid unknown Adenosine triphosphate + Citric acid + Coenzyme Adetails
Adenosine triphosphate + Citric acid + Coenzyme A unknown ADP + Phosphoric acid + Acetyl-CoA + Oxalacetic aciddetails
Gene Name:
PC
Uniprot ID:
P11498
Reactions
Adenosine triphosphate + Pyruvic acid + Carbonic acid unknown ADP + Phosphoric acid + Oxalacetic aciddetails
Gene Name:
CS
Uniprot ID:
O75390
Reactions
Acetyl-CoA + Water + Oxalacetic acid unknown Citric acid + Coenzyme Adetails
Citric acid + Coenzyme A unknown Acetyl-CoA + Water + Oxalacetic aciddetails
Gene Name:
DDO
Uniprot ID:
Q99489
Reactions
D-Aspartic acid + Water + Oxygen unknown Oxalacetic acid + Ammonia + Hydrogen peroxidedetails
Gene Name:
GOT1
Uniprot ID:
P17174
Reactions
L-Aspartic acid + Oxoglutaric acid unknown Oxalacetic acid + L-Glutamic aciddetails
Gene Name:
GOT2
Uniprot ID:
P00505
Reactions
L-Aspartic acid + Oxoglutaric acid unknown Oxalacetic acid + L-Glutamic aciddetails
Gene Name:
ME1
Uniprot ID:
P48163
Reactions
Oxalacetic acid unknown Pyruvic acid + CO(2)details
Gene Name:
MDH2
Uniprot ID:
P40926
Reactions
L-Malic acid + NAD unknown Oxalacetic acid + NADHdetails
L-Malic acid + NAD unknown Oxalacetic acid + NADH + Hydrogen Iondetails
Gene Name:
ME3
Uniprot ID:
Q16798
Reactions
Oxalacetic acid unknown Pyruvic acid + CO(2)details
Gene Name:
MDH1
Uniprot ID:
P40925
Reactions
L-Malic acid + NAD unknown Oxalacetic acid + NADHdetails
L-Malic acid + NAD unknown Oxalacetic acid + NADH + Hydrogen Iondetails
Gene Name:
ME2
Uniprot ID:
P23368
Reactions
Oxalacetic acid unknown Pyruvic acid + CO(2)details
Gene Name:
PCK2
Uniprot ID:
Q16822
Reactions
Guanosine triphosphate + Oxalacetic acid unknown Guanosine diphosphate + Phosphoenolpyruvic acid + CO(2)details
Guanosine triphosphate + Oxalacetic acid unknown Guanosine diphosphate + Phosphoenolpyruvic acid + Carbon dioxidedetails
Inosine triphosphate + Oxalacetic acid unknown IDP + Phosphoenolpyruvic acid + Carbon dioxidedetails
Gene Name:
PCK1
Uniprot ID:
P35558
Reactions
Guanosine triphosphate + Oxalacetic acid unknown Guanosine diphosphate + Phosphoenolpyruvic acid + CO(2)details
Guanosine triphosphate + Oxalacetic acid unknown Guanosine diphosphate + Phosphoenolpyruvic acid + Carbon dioxidedetails
Inosine triphosphate + Oxalacetic acid unknown IDP + Phosphoenolpyruvic acid + Carbon dioxidedetails
Gene Name:
IL4I1
Uniprot ID:
Q96RQ9
Reactions
L-Aspartic acid + Water + Oxygen unknown Oxalacetic acid + Ammonia + Hydrogen peroxidedetails
Gene Name:
ASPDH
Uniprot ID:
A6ND91
Reactions
L-Aspartic acid + Water + NAD(P)(+) unknown Oxalacetic acid + Ammonia + NAD(P)Hdetails
Gene Name:
GOT1L1
Uniprot ID:
Q8NHS2
Reactions
L-Aspartic acid + Oxoglutaric acid unknown Oxalacetic acid + L-Glutamic aciddetails
Gene Name:
NIT2
Uniprot ID:
Q9NQR4
Reactions
2-Oxosuccinamate + Water unknown Oxalacetic acid + Ammoniadetails