Human Metabolome Database Version 3.5

Showing metabocard for Oxalacetic acid (HMDB00223)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:08:06 -0700
HMDB ID HMDB00223
Secondary Accession Numbers None
Metabolite Identification
Common 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C4H4O5
Average Molecular Weight 132.0716
Monoisotopic Molecular Weight 132.005873238
IUPAC Name 2-oxobutanedioic acid
Traditional IUPAC Name oxaloacetic acid
CAS Registry Number 328-42-7
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 Key KHPXUQMNIQBQEV-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Organic Acids and Derivatives
Class Carboxylic Acids and Derivatives
Sub Class Dicarboxylic 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 Parent Dicarboxylic Acids and Derivatives
Ontology
Status Detected 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
Application Not Available
Cellular locations
  • Mitochondria
  • Peroxisome
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 161 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 134 mg/mL Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 57.1 g/L ALOGPS
LogP -0.68 ALOGPS
LogP -0.042 ChemAxon
LogS -0.36 ALOGPS
pKa (strongest acidic) 2.41 ChemAxon
pKa (strongest basic) -9.9 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 91.67 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 24.33 ChemAxon
Polarizability 10.06 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
Gas-MS Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies )
MS/MS Spectrum GC-MS
MS/MS Spectrum GC-MS
MS/MS Spectrum GC-MS
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Mitochondria
  • Peroxisome
Biofluid Locations
  • Cellular Cytoplasm
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Liver
Pathways
Name SMPDB Link KEGG Link
Alanine Metabolism SMP00055 map00250 Link_out
Malate-Aspartate Shuttle SMP00129 Not Available
Citric Acid Cycle SMP00057 map00020 Link_out
Gluconeogenesis SMP00128 map00010 Link_out
Aspartate Metabolism SMP00067 map00250 Link_out
Urea Cycle SMP00059 map00330 Link_out
Pyruvate Metabolism SMP00060 map00620 Link_out
Transfer of Acetyl Groups into Mitochondria SMP00466 Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Cellular Cytoplasm Detected and Quantified
61 uM Adult (>18 years old) Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
7.3 (6.1-8.3) uM Adult (>18 years old) Both Normal
  • Geigy Scient...
Cerebrospinal Fluid (CSF) Detected and Quantified
27 +/- 15 uM Not Specified Both Normal
Urine Detected and Quantified
2.2 (1.16-5.94) umol/mmol creatinine Adult (>18 years old) Female Normal
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Male Comment Normal
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Male Comment Normal
Urine Detected and Quantified
2.27 (0.51-4.48) umol/mmol creatinine Adult (>18 years old) Male Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Cellular Cytoplasm Detected and Quantified 2 uM Adult (>18 years old) Both Anoxia
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 Link_out
      Associated OMIM IDs None
      DrugBank ID Not Available
      DrugBank Metabolite ID Not Available
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB001479
      KNApSAcK ID C00001197 Link_out
      Chemspider ID 945 Link_out
      KEGG Compound ID C00036 Link_out
      BioCyc ID OXALACETIC_ACID Link_out
      BiGG ID 33604 Link_out
      Wikipedia Link Oxalacetic acid Link_out
      NuGOwiki Link HMDB00223 Link_out
      Metagene Link HMDB00223 Link_out
      METLIN ID 123 Link_out
      PubChem Compound 970 Link_out
      PDB ID Not Available
      ChEBI ID 30744 Link_out
      References
      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
      General References
      1. 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 Link_out
      2. el-Sharabasy MM: Observations on calcium oxalate stone formers. Br J Urol. 1992 Nov;70(5):474-7. Pubmed: 1361403 Link_out
      3. 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 Link_out
      4. 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 Link_out
      5. 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 Link_out
      6. 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 Link_out
      7. 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 Link_out
      8. 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 Link_out
      9. 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 Link_out
      10. 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 Link_out
      11. 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 Link_out
      12. 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 Link_out
      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 Link_out
      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 Link_out

      Enzymes
      Name: ATP-citrate synthase
      Reactions:
      ADP + Phosphoric acid + Acetyl-CoA + Oxalacetic acid unknown Adenosine triphosphate + Citric acid + Coenzyme A details
      Adenosine triphosphate + Citric acid + Coenzyme A unknown ADP + Phosphoric acid + Acetyl-CoA + Oxalacetic acid details
      Gene Name: ACLY
      Uniprot ID: P53396 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Pyruvate carboxylase, mitochondrial
      Reactions:
      Adenosine triphosphate + Pyruvic acid + Carbonic acid unknown ADP + Phosphoric acid + Oxalacetic acid details
      Gene Name: PC
      Uniprot ID: P11498 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Citrate synthase, mitochondrial
      Reactions:
      Acetyl-CoA + Water + Oxalacetic acid unknown Citric acid + Coenzyme A details
      Citric acid + Coenzyme A unknown Acetyl-CoA + Water + Oxalacetic acid details
      Gene Name: CS
      Uniprot ID: O75390 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: D-aspartate oxidase
      Reactions:
      D-Aspartic acid + Water + Oxygen unknown Oxalacetic acid + Ammonia + Hydrogen peroxide details
      Gene Name: DDO
      Uniprot ID: Q99489 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Aspartate aminotransferase, cytoplasmic
      Reactions:
      L-Aspartic acid + Oxoglutaric acid unknown Oxalacetic acid + L-Glutamic acid details
      Gene Name: GOT1
      Uniprot ID: P17174 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Aspartate aminotransferase, mitochondrial
      Reactions:
      L-Aspartic acid + Oxoglutaric acid unknown Oxalacetic acid + L-Glutamic acid details
      Gene Name: GOT2
      Uniprot ID: P00505 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: NADP-dependent malic enzyme
      Reactions:
      Oxalacetic acid unknown Pyruvic acid + CO(2) details
      Gene Name: ME1
      Uniprot ID: P48163 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Malate dehydrogenase, mitochondrial
      Reactions:
      L-Malic acid + NAD unknown Oxalacetic acid + NADH details
      L-Malic acid + NAD unknown Oxalacetic acid + NADH + Hydrogen Ion details
      Gene Name: MDH2
      Uniprot ID: P40926 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: NADP-dependent malic enzyme, mitochondrial
      Reactions:
      Oxalacetic acid unknown Pyruvic acid + CO(2) details
      Gene Name: ME3
      Uniprot ID: Q16798 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Malate dehydrogenase, cytoplasmic
      Reactions:
      L-Malic acid + NAD unknown Oxalacetic acid + NADH details
      L-Malic acid + NAD unknown Oxalacetic acid + NADH + Hydrogen Ion details
      Gene Name: MDH1
      Uniprot ID: P40925 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: NAD-dependent malic enzyme, mitochondrial
      Reactions:
      Oxalacetic acid unknown Pyruvic acid + CO(2) details
      Gene Name: ME2
      Uniprot ID: P23368 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Phosphoenolpyruvate carboxykinase [GTP], mitochondrial
      Reactions:
      Guanosine triphosphate + Oxalacetic acid unknown Guanosine diphosphate + Phosphoenolpyruvic acid + CO(2) details
      Guanosine triphosphate + Oxalacetic acid unknown Guanosine diphosphate + Phosphoenolpyruvic acid + Carbon dioxide details
      Inosine triphosphate + Oxalacetic acid unknown IDP + Phosphoenolpyruvic acid + Carbon dioxide details
      Gene Name: PCK2
      Uniprot ID: Q16822 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Phosphoenolpyruvate carboxykinase, cytosolic [GTP]
      Reactions:
      Guanosine triphosphate + Oxalacetic acid unknown Guanosine diphosphate + Phosphoenolpyruvic acid + CO(2) details
      Guanosine triphosphate + Oxalacetic acid unknown Guanosine diphosphate + Phosphoenolpyruvic acid + Carbon dioxide details
      Inosine triphosphate + Oxalacetic acid unknown IDP + Phosphoenolpyruvic acid + Carbon dioxide details
      Gene Name: PCK1
      Uniprot ID: P35558 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: L-amino-acid oxidase
      Reactions:
      L-Aspartic acid + Water + Oxygen unknown Oxalacetic acid + Ammonia + Hydrogen peroxide details
      Gene Name: IL4I1
      Uniprot ID: Q96RQ9 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Putative L-aspartate dehydrogenase
      Reactions:
      L-Aspartic acid + Water + NAD(P)(+) unknown Oxalacetic acid + Ammonia + NAD(P)H details
      Gene Name: ASPDH
      Uniprot ID: A6ND91 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Putative aspartate aminotransferase, cytoplasmic 2
      Reactions:
      L-Aspartic acid + Oxoglutaric acid unknown Oxalacetic acid + L-Glutamic acid details
      Gene Name: GOT1L1
      Uniprot ID: Q8NHS2 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Omega-amidase NIT2
      Reactions:
      2-Oxosuccinamate + Water unknown Oxalacetic acid + Ammonia details
      Gene Name: NIT2
      Uniprot ID: Q9NQR4 Link_out
      Protein Sequence: FASTA