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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 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
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 Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)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-MS (Non-derivatized)splash10-007a-9210000000-020f60717e2ea79d1ccdView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000b-9540000000-a53f674cc98960834f88View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001a-8940000000-40b790e06141d7180938View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-4930000000-7e995327b0b9c1af0914View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-9100000000-6718417e7196063f9544View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00ds-9520000000-5a082ec8843f6fbc3b15View in MoNA
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
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-014i-0900000000-7c598fd9c78acb94dacdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 3V, positivesplash10-014i-4900000000-e7803730ae7986a1b9fbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 4V, positivesplash10-014r-5900000000-8e478338a7c0e65e62baView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 5V, positivesplash10-014r-7900000000-f681763317e1ae86e691View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 7V, positivesplash10-00kr-9600000000-aa8adf9a96041dddbbddView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 10V, positivesplash10-000i-9200000000-e62c47ca2bc492900178View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 15V, positivesplash10-000i-9000000000-5485ddd84a64ea0ca0b9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 17V, positivesplash10-000i-9000000000-79521cb04a2b23e39c1eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 20V, positivesplash10-000m-9000000000-601c8d2ec63f8b01a61eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 23V, positivesplash10-000e-9000000000-13d369c58d8930958d92View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 25V, positivesplash10-0005-9000000000-df8387ef907fb71342ebView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 27V, positivesplash10-0005-9000000000-908644b5d7041346f582View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 30V, positivesplash10-0005-9000000000-ecca787a800164d0296fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 33V, positivesplash10-0005-9000000000-180a7c51b1f93cb8fff2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 35V, positivesplash10-0005-9000000000-709c49f609f5a711a288View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 40V, positivesplash10-0005-9000000000-aa103ab9beb03bd6eb22View 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 AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
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