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Escherichia coli K-12 substr. MG1655 Compound: oxaloacetate

Synonyms: keto-oxaloacetate, oxaloacetic acid, oxalacetic acid, oxalacetate

Chemical Formula: C4H2O5

Molecular Weight: 130.06 Daltons

Monoisotopic Molecular Weight: 132.0058732389 Daltons

oxaloacetate compound structure

SMILES: C(C([O-])=O)C(=O)C([O-])=O

InChI: InChI=1S/C4H4O5/c5-2(4(8)9)1-3(6)7/h1H2,(H,6,7)(H,8,9)/p-2


Unification Links: CAS:328-42-7, ChEBI:16452, ChemSpider:144251, HMDB:HMDB00223, IAF1260:33604, KEGG:C00036, MetaboLights:MTBLC16452, PubChem:164550

Tautomers: enol-oxaloacetate

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): -189.6

Reactions known to consume the compound:

2-methylcitrate cycle I :
oxaloacetate + propanoyl-CoA + H2O → (2S,3S)-2-methylcitrate + coenzyme A + H+

gluconeogenesis I :
oxaloacetate + ATP → CO2 + phosphoenolpyruvate + ADP

glyoxylate cycle , mixed acid fermentation , TCA cycle I (prokaryotic) :
oxaloacetate + acetyl-CoA + H2O → citrate + coenzyme A + H+

Not in pathways:
oxaloacetate + H+ → pyruvate + CO2

Reactions known to produce the compound:

citrate degradation :
a citryl-[holo citrate lyase acyl-carrier protein] → oxaloacetate + an acetyl-[holo citrate lyase acyl-carrier protein] + H+

TCA cycle I (prokaryotic) :
(S)-malate + an electron-transfer quinone[inner membrane]oxaloacetate + an electron-transfer quinol[inner membrane]

Not in pathways:
citrate → acetate + oxaloacetate

Reactions known to both consume and produce the compound:

gluconeogenesis I , glyoxylate cycle , TCA cycle I (prokaryotic) :
(S)-malate + NAD+oxaloacetate + NADH + H+

L-aspartate biosynthesis , L-glutamate degradation II :
L-aspartate + 2-oxoglutarate ↔ oxaloacetate + L-glutamate

mixed acid fermentation :
(S)-malate + NAD+oxaloacetate + NADH + H+
oxaloacetate + phosphate ↔ phosphoenolpyruvate + hydrogen carbonate

Not in pathways:
L-tartrate ↔ oxaloacetate + H2O
pyridoxamine + oxaloacetate ↔ pyridoxal + L-aspartate

In Reactions of unknown directionality:

Not in pathways:
D-tartrate = oxaloacetate + H2O
oxaloacetate = enol-oxaloacetate

In Redox half-reactions:
oxaloacetate[in] + 2 H+[in] + 2 e-[membrane] → (S)-malate[in]

Enzymes activated by oxaloacetate, sorted by the type of activation, are:

Activator (Mechanism unknown) of: isocitrate dehydrogenase phosphatase [Nimmo84]

Enzymes inhibited by oxaloacetate, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: isocitrate dehydrogenase [Comment 1] Inhibitor (Allosteric) of: malate dehydrogenase [Sanwal69, Sanwal69a, Bologna07], citrate synthase Inhibitor (Mechanism unknown) of: 2-oxoglutarate decarboxylase [Frank07], phosphoenolpyruvate synthetase [Chulavatnatol73], citrate lyase [Helmward89], isocitrate dehydrogenase kinase [Nimmo84], malate dehydrogenase, NAD-requiring [Yamaguchi73, Comment 2], glutamine synthetase adenylyltransferase [Ebner70, Comment 3], fumarate reductase [Iverson99]

This compound has been characterized as an alternative substrate of the following enzymes: malate dehydrogenase, NAD-requiring, 2-keto-4-hydroxyglutarate aldolase, D-lactate dehydrogenase, tyrosine aminotransferase, malate dehydrogenase, phenylalanine aminotransferase


Bologna07: Bologna FP, Andreo CS, Drincovich MF (2007). "Escherichia coli malic enzymes: two isoforms with substantial differences in kinetic properties, metabolic regulation, and structure." J Bacteriol 189(16);5937-46. PMID: 17557829

Chulavatnatol73: Chulavatnatol M, Atkinson DE (1973). "Phosphoenolpyruvate synthetase from Escherichia coli. Effects of adenylate energy charge and modifier concentrations." J Biol Chem 248(8);2712-5. PMID: 4572511

Ebner70: Ebner E, Wolf D, Gancedo C, Elsasser S, Holzer H (1970). "ATP: glutamine synthetase adenylyltransferase from Escherichia coli B. Purification and properties." Eur J Biochem 1970;14(3);535-44. PMID: 4920894

Frank07: Frank RA, Price AJ, Northrop FD, Perham RN, Luisi BF (2007). "Crystal structure of the E1 component of the Escherichia coli 2-oxoglutarate dehydrogenase multienzyme complex." J Mol Biol 368(3);639-51. PMID: 17367808

Helmward89: Helmward Z "Handbook of Enzyme Inhibitors. 2nd, revised and enlarged edition." Weinheim, Federal Republic of Germany ; New York, NY, USA , 1989.

Iverson99: Iverson TM, Luna-Chavez C, Cecchini G, Rees DC (1999). "Structure of the Escherichia coli fumarate reductase respiratory complex." Science 1999;284(5422);1961-6. PMID: 10373108

Nimmo84: Nimmo GA, Nimmo HG (1984). "The regulatory properties of isocitrate dehydrogenase kinase and isocitrate dehydrogenase phosphatase from Escherichia coli ML308 and the roles of these activities in the control of isocitrate dehydrogenase." Eur J Biochem 1984;141(2);409-14. PMID: 6329757

Nimmo86: Nimmo HG (1986). "Kinetic mechanism of Escherichia coli isocitrate dehydrogenase and its inhibition by glyoxylate and oxaloacetate." Biochem J 1986;234(2);317-23. PMID: 3521584

Sanwal69: Sanwal BD, Smando R (1969). "Malic enzyme of Escherichia coli. Diversity of the effectors controlling enzyme activity." J Biol Chem 1969;244(7);1817-23. PMID: 4388614

Sanwal69a: Sanwal BD, Smando R (1969). "Malic enzyme of Escherichia coli. Possible mechanism for allosteric effects." J Biol Chem 1969;244(7);1824-30. PMID: 4388615

Yamaguchi73: Yamaguchi M, Tokushige M, Katsuki H (1973). "Studies on regulatory functions of malic enzymes. II. Purification and molecular properties of nicotinamide adenine dinucleotide-linked malic enzyme from Eschericha coli." J Biochem (Tokyo) 1973;73(1);169-80. PMID: 4144085

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Please cite the following article in publications resulting from the use of EcoCyc: Nucleic Acids Research 41:D605-12 2013
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