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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-07-23 05:43:58 UTC
HMDB IDHMDB0000223
Secondary Accession Numbers
  • HMDB00223
Metabolite Identification
Common NameOxalacetic acid
DescriptionOxalacetic acid, also known as keto-oxaloacetate or 2-oxobutanedioate, 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. Oxalacetic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Oxalacetic acid exists in all living species, ranging from bacteria to humans. Within humans, oxalacetic acid participates in a number of enzymatic reactions. In particular, acetyl-CoA and oxalacetic acid can be converted into citric acid; which is mediated by the enzyme citrate synthase, mitochondrial. In addition, oxalacetic acid can be biosynthesized from pyruvic acid through the action of the enzyme pyruvate carboxylase, mitochondrial. In humans, oxalacetic acid is involved in the metabolic disorder called the glutaminolysis and cancer pathway. Outside of the human body, oxalacetic acid has been detected, but not quantified in, several different foods, such as bilberries, babassu palms, lemon balms, other soy products, and peach (var.). This could make oxalacetic acid a potential biomarker for the consumption of these foods.
Structure
Data?1563860638
Synonyms
ValueSource
2-Oxobutanedioic acidChEBI
2-Oxosuccinic acidChEBI
3-Carboxy-3-oxopropanoic acidChEBI
Keto-succinic acidChEBI
Ketosuccinic acidChEBI
OAAChEBI
Oxobutanedioic acidChEBI
Oxosuccinic acidChEBI
Oxaloacetic acidKegg
Keto-oxaloacetateKegg
2-OxobutanedioateGenerator
2-OxosuccinateGenerator
3-Carboxy-3-oxopropanoateGenerator
Keto-succinateGenerator
KetosuccinateGenerator
OxobutanedioateGenerator
OxosuccinateGenerator
OxaloacetateGenerator
Keto-oxaloacetic acidGenerator
OxalacetateGenerator
2-KetosuccinateHMDB
2-Ketosuccinic acidHMDB
a-KetosuccinateHMDB
a-Ketosuccinic acidHMDB
alpha-KetosuccinateHMDB
alpha-Ketosuccinic acidHMDB
OxaloethanoateHMDB
Oxaloethanoic acidHMDB
Acid, oxaloaceticHMDB
Acid, oxalaceticHMDB
2 Ketosuccinic acidHMDB
2 oxo Butanedioic acidHMDB
2-oxo-Butanedioic acidHMDB
Chemical FormulaC4H4O5
Average Molecular Weight132.0716
Monoisotopic Molecular Weight132.005873238
IUPAC Name2-oxobutanedioic acid
Traditional Nameoxalacetate
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
Description 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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassShort-chain keto acids and derivatives
Direct ParentShort-chain keto acids and derivatives
Alternative Parents
Substituents
  • Beta-keto acid
  • Short-chain keto acid
  • Alpha-keto acid
  • Beta-hydroxy ketone
  • Dicarboxylic acid or derivatives
  • 1,3-dicarbonyl compound
  • Alpha-hydroxy ketone
  • Ketone
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carbonyl group
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

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 Area91.67 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity24.33 m³·mol⁻¹ChemAxon
Polarizability10.06 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00dr-4900000000-9d943d40beaca3c602a1JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)splash10-007a-9210000000-020f60717e2ea79d1ccdJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)splash10-000b-9540000000-a53f674cc98960834f88JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)splash10-001a-8940000000-40b790e06141d7180938JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-007a-9210000000-020f60717e2ea79d1ccdJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000b-9540000000-a53f674cc98960834f88JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001a-8940000000-40b790e06141d7180938JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-4930000000-7e995327b0b9c1af0914JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-9100000000-6718417e7196063f9544JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00ds-9520000000-5a082ec8843f6fbc3b15JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-000i-9000000000-0be675f3aa3e973393b7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-000f-9000000000-4fba97fcd7b0f2215f75JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0006-9000000000-9b1f4171aee6283a3cbdJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-014i-0900000000-7c598fd9c78acb94dacdJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-3900000000-6f4e965a3f513bf8db13JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9600000000-8ae7abf60057088e14dbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01bc-9100000000-5724c215c46a4f568140JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0019-8900000000-829898d0849b1fbf1c28JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9100000000-5a5ff8fb7cb52eebf0c8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-657d1384d478ddc33b6dJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-f371299a07d43c23ff1dJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Mitochondria
  • Peroxisome
Biospecimen Locations
  • Cellular Cytoplasm
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Locations
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cellular CytoplasmDetected and Quantified61 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified7.3 (6.1-8.3) uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Cerebrospinal Fluid (CSF)Detected and Quantified27 +/- 15 uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified2.2 (1.16-5.94) umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected but not Quantified Adult (>18 years old)Male
Normal
details
UrineDetected but not Quantified Adult (>18 years old)Male
Normal
details
UrineDetected and Quantified2.27 (0.51-4.48) umol/mmol creatinineAdult (>18 years old)MaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cellular CytoplasmDetected and Quantified2 uMAdult (>18 years old)BothAnoxia details
Associated Disorders and Diseases
Disease References
Anoxia
  1. 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
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001479
KNApSAcK IDC00001197
Chemspider ID945
KEGG Compound IDC00036
BioCyc IDOXALACETIC_ACID
BiGG ID33604
Wikipedia LinkOxaloacetic_acid
METLIN ID123
PubChem Compound970
PDB IDNot Available
ChEBI ID30744
Food Biomarker OntologyNot Available
VMH IDNot Available
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. 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 ]
  2. el-Sharabasy MM: Observations on calcium oxalate stone formers. Br J Urol. 1992 Nov;70(5):474-7. [PubMed:1361403 ]
  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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  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 ]

Only showing the first 10 proteins. There are 17 proteins in total.

Enzymes

General function:
Involved in ATP citrate synthase activity
Specific function:
ATP citrate-lyase is the primary enzyme responsible for the synthesis of cytosolic acetyl-CoA in many tissues. Has a central role in de novo lipid synthesis. In nervous tissue it may be involved in the biosynthesis of acetylcholine.
Gene Name:
ACLY
Uniprot ID:
P53396
Molecular weight:
120838.27
Reactions
ADP + Phosphate + Acetyl-CoA + Oxalacetic acid → Adenosine triphosphate + Citric acid + Coenzyme Adetails
Adenosine triphosphate + Citric acid + Coenzyme A → ADP + Phosphate + Acetyl-CoA + Oxalacetic aciddetails
General function:
Involved in catalytic activity
Specific function:
Pyruvate carboxylase catalyzes a 2-step reaction, involving the ATP-dependent carboxylation of the covalently attached biotin in the first step and the transfer of the carboxyl group to pyruvate in the second. Catalyzes in a tissue specific manner, the initial reactions of glucose (liver, kidney) and lipid (adipose tissue, liver, brain) synthesis from pyruvate.
Gene Name:
PC
Uniprot ID:
P11498
Molecular weight:
129632.565
Reactions
Adenosine triphosphate + Pyruvic acid + Hydrogen carbonate → ADP + Phosphate + Oxalacetic aciddetails
General function:
Involved in transferase activity, transferring acyl groups, acyl groups converted into alkyl on transfer
Specific function:
Not Available
Gene Name:
CS
Uniprot ID:
O75390
Molecular weight:
51712.025
Reactions
Acetyl-CoA + Water + Oxalacetic acid → Citric acid + Coenzyme Adetails
Citric acid + Coenzyme A → Acetyl-CoA + Water + Oxalacetic aciddetails
General function:
Involved in D-amino-acid oxidase activity
Specific function:
Selectively catalyzes the oxidative deamination of D-aspartate and its N-methylated derivative, N-methyl D-aspartate.
Gene Name:
DDO
Uniprot ID:
Q99489
Molecular weight:
40992.53
Reactions
D-Aspartic acid + Water + Oxygen → Oxalacetic acid + Ammonia + Hydrogen peroxidedetails
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Plays a key role in amino acid metabolism (By similarity).
Gene Name:
GOT1
Uniprot ID:
P17174
Molecular weight:
46247.14
Reactions
L-Aspartic acid + Oxoglutaric acid → Oxalacetic acid + L-Glutamic aciddetails
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). Plays a key role in amino acid metabolism. Important for metabolite exchange between mitochondria and cytosol. Facilitates cellular uptake of long-chain free fatty acids.
Gene Name:
GOT2
Uniprot ID:
P00505
Molecular weight:
47517.285
Reactions
L-Aspartic acid + Oxoglutaric acid → Oxalacetic acid + L-Glutamic aciddetails
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ME1
Uniprot ID:
P48163
Molecular weight:
64149.075
Reactions
Oxalacetic acid → Pyruvic acid + CO(2)details
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Not Available
Gene Name:
MDH2
Uniprot ID:
P40926
Molecular weight:
35502.935
Reactions
L-Malic acid + NAD → Oxalacetic acid + NADHdetails
L-Malic acid + NAD → Oxalacetic acid + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ME3
Uniprot ID:
Q16798
Molecular weight:
67067.875
Reactions
Oxalacetic acid → Pyruvic acid + CO(2)details
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Not Available
Gene Name:
MDH1
Uniprot ID:
P40925
Molecular weight:
38627.255
Reactions
L-Malic acid + NAD → Oxalacetic acid + NADHdetails
L-Malic acid + NAD → Oxalacetic acid + NADH + Hydrogen Iondetails

Only showing the first 10 proteins. There are 17 proteins in total.