Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB110103
Identification
Name: oxaloacetate
Description:A C4-dicarboxylate resuting from deprotonation of both carboxy groups of oxaloacetic acid.
Structure
Thumb
Synonyms:
  • keto-oxaloacetate
  • oxaloacetic acid
  • oxalacetic acid
  • oxalacetate
Chemical Formula: C4H2O5
Average Molecular Weight: 130.06
Monoisotopic Molecular Weight: 132.0058732389
InChI Key: KHPXUQMNIQBQEV-UHFFFAOYSA-L
InChI: InChI=1S/C4H4O5/c5-2(4(8)9)1-3(6)7/h1H2,(H,6,7)(H,8,9)/p-2
CAS number: 328-42-7
IUPAC Name:2-oxobutanedioate
Traditional IUPAC Name: oxalacetate
SMILES:C(C([O-])=O)C(=O)C([O-])=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Organic acids and derivatives
Sub ClassKeto acids and derivatives
Direct Parent Short-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 Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-2
Melting point: 161 °C
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity24.33 m3·mol-1ChemAxon
Polarizability10.06 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
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
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 Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Wolfenden R, Lewis CA, Yuan Y (2011)Kinetic challenges facing oxalate, malonate, acetoacetate, and oxaloacetate decarboxylases. Journal of the American Chemical Society 133, Pubmed: 21434608
  • Kinoshita H, Nagasaki J, Yoshikawa N, Yamamoto A, Takito S, Kawasaki M, Sugiyama T, Miyake H, Weber AP, Taniguchi M (2011)The chloroplastic 2-oxoglutarate/malate transporter has dual function as the malate valve and in carbon/nitrogen metabolism. The Plant journal : for cell and molecular biology 65, Pubmed: 21175886
  • Tomasiak TM, Archuleta TL, Andréll J, Luna-Chávez C, Davis TA, Sarwar M, Ham AJ, McDonald WH, Yankovskaya V, Stern HA, Johnston JN, Maklashina E, Cecchini G, Iverson TM (2011)Geometric restraint drives on- and off-pathway catalysis by the Escherichia coli menaquinol:fumarate reductase. The Journal of biological chemistry 286, Pubmed: 21098488
  • Williams DS, Cash A, Hamadani L, Diemer T (2009)Oxaloacetate supplementation increases lifespan in Caenorhabditis elegans through an AMPK/FOXO-dependent pathway. Aging cell 8, Pubmed: 19793063
  • Luque-Almagro VM, Merchán F, Blasco R, Igeńo MI, Martínez-Luque M, Moreno-Vivián C, Castillo F, Roldán MD (2011)Cyanide degradation by Pseudomonas pseudoalcaligenes CECT5344 involves a malate:quinone oxidoreductase and an associated cyanide-insensitive electron transfer chain. Microbiology (Reading, England) 157, Pubmed: 21178163
  • Carvalho AS, Torres LB, Persike DS, Fernandes MJ, Amado D, Naffah-Mazzacoratti Mda G, Cavalheiro EA, da Silva AV (2011)Neuroprotective effect of pyruvate and oxaloacetate during pilocarpine induced status epilepticus in rats. Neurochemistry international 58, Pubmed: 21185899
  • Wang Y, Blatt MR (2011)Anion channel sensitivity to cytosolic organic acids implicates a central role for oxaloacetate in integrating ion flux with metabolism in stomatal guard cells. The Biochemical journal 439, Pubmed: 21745184
  • Stipanovic RD, Wheeler MH, Puckhaber LS, Liu J, Bell AA, Williams HJ (2011)Nuclear magnetic resonance (NMR) studies on the biosynthesis of fusaric acid from Fusarium oxysporum f. sp. vasinfectum. Journal of agricultural and food chemistry 59, Pubmed: 21495723
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
External Links:
ResourceLink
CAS328-42-7
ChEBI16452
ChemSpider144251
HMDBHMDB00223
IAF126033604
KEGGC00036
MetaboLightsMTBLC16452
PubChem164550