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Record Information
Version1.0
Creation Date2016-09-30 22:26:59 UTC
Update Date2020-06-04 19:53:36 UTC
BMDB IDBMDB0000223
Secondary Accession Numbers
  • BMDB00223
Metabolite Identification
Common NameOxalacetic acid
DescriptionOxalacetic acid, also known as oxaloacetate or 2-oxosuccinate, 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 exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Oxalacetic acid exists in all living species, ranging from bacteria to humans.
Structure
Thumb
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 NameNot Available
Traditional NameNot Available
CAS Registry Number328-42-7
SMILESNot Available
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
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • 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 PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
  • Peroxisome
Biospecimen Locations
  • Liver
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
MilkDetected and Quantified7 - 24 uMNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000223
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB031075
KNApSAcK IDC00001197
Chemspider ID945
KEGG Compound IDC00036
BioCyc IDOXALACETIC_ACID
BiGG ID33604
Wikipedia LinkOxaloacetic_acid
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. Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9. [PubMed:22098372 ]
  2. Antunes-Fernandes EC, van Gastelen S, Dijkstra J, Hettinga KA, Vervoort J: Milk metabolome relates enteric methane emission to milk synthesis and energy metabolism pathways. J Dairy Sci. 2016 Aug;99(8):6251-6262. doi: 10.3168/jds.2015-10248. Epub 2016 May 26. [PubMed:27236769 ]

Enzymes

General function:
Energy production and conversion
Specific function:
Catalyzes the cleavage of citrate into oxaloacetate and acetyl-CoA, the latter serving as common substrate for de novo cholesterol and fatty acid synthesis.
Gene Name:
ACLY
Uniprot ID:
Q32PF2
Molecular weight:
119789.0
Reactions
Coenzyme A + Citric acid + Adenosine triphosphate → Oxalacetic acid + ADP + Acetyl-CoAdetails
General function:
Energy production and conversion
Specific function:
Not Available
Gene Name:
CS
Uniprot ID:
Q29RK1
Molecular weight:
51773.0
Reactions
Acetyl-CoA + Water + Oxalacetic acid → Citric acid + Coenzyme Adetails
General function:
Amino acid transport and metabolism
Specific function:
Biosynthesis of L-glutamate from L-aspartate or L-cysteine. Important regulator of levels of glutamate, the major excitatory neurotransmitter of the vertebrate central nervous system. Acts as a scavenger of glutamate in brain neuroprotection. The aspartate aminotransferase activity is involved in hepatic glucose synthesis during development and in adipocyte glyceroneogenesis. Using L-cysteine as substrate, regulates levels of mercaptopyruvate, an important source of hydrogen sulfide. Mercaptopyruvate is converted into H(2)S via the action of 3-mercaptopyruvate sulfurtransferase (3MST). Hydrogen sulfide is an important synaptic modulator and neuroprotectant in the brain (By similarity).
Gene Name:
GOT1
Uniprot ID:
P33097
Molecular weight:
46399.0
Reactions
Oxoglutaric acid + L-Aspartic acid → Oxalacetic acid + L-Glutamic aciddetails
General function:
Amino acid transport and metabolism
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 (By similarity).
Gene Name:
GOT2
Uniprot ID:
P12344
Molecular weight:
47514.0
Reactions
L-Aspartic acid + Oxoglutaric acid → Oxalacetic acid + L-Glutamic aciddetails
General function:
Amino acid transport and metabolism
Specific function:
Not Available
Gene Name:
GOT1L1
Uniprot ID:
Q2T9S8
Molecular weight:
45918.0
General function:
Involved in ATP binding
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 (By similarity).
Gene Name:
PC
Uniprot ID:
Q29RK2
Molecular weight:
129698.0
Reactions
Adenosine triphosphate + Pyruvic acid + Hydrogen carbonate → ADP + Hydrogen phosphate + Oxalacetic aciddetails
General function:
Energy production and conversion
Specific function:
Not Available
Gene Name:
MDH2
Uniprot ID:
Q32LG3
Molecular weight:
35668.0
General function:
Energy production and conversion
Specific function:
Regulates cataplerosis and anaplerosis, the processes that control the levels of metabolic intermediates in the citric acid cycle. At low glucose levels, it catalyzes the cataplerotic conversion of oxaloacetate (OAA) to phosphoenolpyruvate (PEP), the rate-limiting step in the metabolic pathway that produces glucose from lactate and other precursors derived from the citric acid cycle. At high glucose levels, it catalyzes the anaplerotic conversion of phosphoenolpyruvate to oxaloacetate.
Gene Name:
PCK1
Uniprot ID:
Q8HYZ4
Molecular weight:
69353.0
Reactions
Guanosine triphosphate + Oxalacetic acid → Guanosine diphosphate + Phosphoenolpyruvic acid + Carbon dioxidedetails
General function:
Amino acid transport and metabolism
Specific function:
Not Available
Gene Name:
DDO
Uniprot ID:
P31228
Molecular weight:
37660.0
Reactions
D-Aspartic acid + Water + Oxygen → Oxalacetic acid + Ammonia + Hydrogen peroxidedetails
General function:
Energy production and conversion
Specific function:
Not Available
Gene Name:
MDH2
Uniprot ID:
Q58DR9
Molecular weight:
30024.0
General function:
Energy production and conversion
Specific function:
Not Available
Gene Name:
MDH1
Uniprot ID:
Q3T145
Molecular weight:
36438.0
Reactions
Oxalacetic acid + Hydrogen + NADPH → NAD + L-Malic aciddetails
General function:
Energy production and conversion
Specific function:
Not Available
Gene Name:
MDH2
Uniprot ID:
Q0QF29
Molecular weight:
29951.0
General function:
Not Available
Specific function:
Not Available
Gene Name:
IL4I1
Uniprot ID:
F1N191
Molecular weight:
64479.0
Reactions
L-Aspartic acid + Water + Oxygen → Oxalacetic acid + Ammonia + Hydrogen peroxidedetails