Oxalacetic acid (ECMDB00223) (M2MDB000092)
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Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 10:24:07 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-06-03 15:53:24 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | Oxalacetic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | Oxaloacetic acid, also known as oxosuccinic acid or oxalacetic acid, is a four-carbon dicarboxylic acid appearing as an intermediate of the citric acid cycle. In vivo, oxaloacetate (the ionized form of oxaloacetic acid) is formed by the oxidation of L-malate, catalyzed by malate dehydrogenase, and reacts with Acetyl-CoA to form citrate, catalyzed by citrate synthase.(wikipedia) A class of ketodicarboxylic acids derived from oxalic acid. Oxaloacetic acid is an intermediate in the citric acid cycle and is converted to aspartic acidD by a transamination reaction. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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Chemical Formula: | C4H4O5 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Weight: | Average: 132.0716 Monoisotopic: 132.005873238 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | KHPXUQMNIQBQEV-UHFFFAOYSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI: | InChI=1S/C4H4O5/c5-2(4(8)9)1-3(6)7/h1H2,(H,6,7)(H,8,9) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS number: | 328-42-7 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name: | 2-oxobutanedioic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | oxalacetate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES: | OC(=O)CC(=O)C(O)=O | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Super Class | Organic acids and derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Class | Keto acids and derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Sub Class | Short-chain keto acids and derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Direct Parent | Short-chain keto acids and derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Alternative Parents | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Substituents |
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Molecular Framework | Aliphatic acyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Descriptors |
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Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
State: | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Charge: | -2 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Melting point: | 161 °C | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
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Predicted Properties |
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Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Reactions: | Citric acid <> Acetic acid + Oxalacetic acid Tartaric acid <> Water + Oxalacetic acid Water + Oxalacetic acid + Propionyl-CoA <> Methylcitric acid + Coenzyme A + Hydrogen ion + (2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate Acetyl-CoA + Water + Oxalacetic acid <> Citric acid + Coenzyme A + Hydrogen ion alpha-Ketoglutarate + L-Aspartic acid <> L-Glutamate + Oxalacetic acid Hydrogen ion + Oxalacetic acid > Carbon dioxide + Pyruvic acid L-Malic acid + Ubiquinone-8 > Oxalacetic acid + Ubiquinol-8 L-Malic acid + Menaquinone 8 > Menaquinol 8 + Oxalacetic acid L-Malic acid + NAD <> Hydrogen ion + NADH + Oxalacetic acid Adenosine triphosphate + Oxalacetic acid <> ADP + Carbon dioxide + Phosphoenolpyruvic acid Carbon dioxide + Water + Phosphoenolpyruvic acid <> Hydrogen ion + Oxalacetic acid + Phosphate + Hydrogen carbonate D-tartrate > Water + Oxalacetic acid Phosphate + Oxalacetic acid <> Water + Phosphoenolpyruvic acid + Carbon dioxide Citric acid + Coenzyme A <> Acetyl-CoA + Water + Oxalacetic acid L-Aspartic acid + Water + Oxygen <> Oxalacetic acid + Ammonia + Hydrogen peroxide Methylcitric acid + Coenzyme A <> Propionyl-CoA + Oxalacetic acid + Water L-Malic acid + FAD <> FADH2 + Oxalacetic acid Oxalacetic acid + L-Arogenate <> L-Aspartic acid + Prephenate Oxalacetic acid + Water + Propionyl-CoA <> Hydrogen ion + Methylcitric acid + Coenzyme A L-Aspartic acid + Oxoglutaric acid <> Oxalacetic acid + L-Glutamate Citric acid > Acetic acid + Oxalacetic acid D-tartrate Water + Oxalacetic acid L-Malic acid + a quinone > Oxalacetic acid + a quinol L-Malic acid + Oxygen <> Oxalacetic acid + Hydrogen peroxide Oxalacetic acid enol-oxaloacetate Phosphate + Oxalacetic acid <> Phosphoenolpyruvic acid + Hydrogen carbonate More...Oxalacetic acid + Adenosine triphosphate > Carbon dioxide + Phosphoenolpyruvic acid + ADP Pyridoxamine + Oxalacetic acid <> Pyridoxal + L-Aspartic acid L-Aspartic acid + Oxoglutaric acid > Oxalacetic acid + L-Glutamate Inorganic phosphate + Oxalacetic acid > Water + Phosphoenolpyruvic acid + Carbonic acid Acetyl-CoA + Water + Oxalacetic acid > Citric acid + CoA (3S)-Citryl-CoA > Acetyl-CoA + Oxalacetic acid L-Malic acid + NAD > Oxalacetic acid + NADH L-Malic acid + a quinone > Oxalacetic acid + reduced quinone Propionyl-CoA + Water + Oxalacetic acid > (2R,3S)-2-Hydroxybutane-1,2,3-tricarboxylate + CoA Tartaric acid > Oxalacetic acid + Water (3S)-Citryl-CoA <> Acetyl-CoA + Oxalacetic acid L-Malic acid + NAD + Oxalacetic acid <> Pyruvic acid + Carbon dioxide + NADH L-Malic acid + Quinone <> Oxalacetic acid + Hydroquinone L-Malic acid + NADP + Oxalacetic acid <> Pyruvic acid + Carbon dioxide + NADPH Acetyl-CoA + Water + Oxalacetic acid > Citric acid + Coenzyme A L-Malic acid + NAD + L-Malic acid <> Oxalacetic acid + NADH + Hydrogen ion Adenosine triphosphate + Pyruvic acid + Hydrogen carbonate > Adenosine diphosphate + Phosphate + Oxalacetic acid + ADP Oxalacetic acid + Water + Acetyl-CoA > Citric acid + Coenzyme A + Hydrogen ion L-Malic acid + NAD + L-Malic acid > Oxalacetic acid + NADH + Hydrogen ion L-Malic acid + Quinone + L-Malic acid > Oxalacetic acid + Hydroquinone L-Aspartic acid + Oxoglutaric acid + L-Aspartic acid > Oxalacetic acid + L-Glutamic acid + L-Glutamate L-Glutamic acid + Oxalacetic acid + L-Glutamate > L-Aspartic acid + Oxoglutaric acid + L-Aspartic acid L-Aspartic acid + Water + Oxygen + L-Aspartic acid > Oxalacetic acid + Ammonia + Hydrogen peroxide Oxalacetic acid + Adenosine triphosphate > Adenosine diphosphate + Carbon dioxide + Phosphoenolpyruvic acid + ADP Propionyl-CoA + Water + Oxalacetic acid + Propionyl-CoA > Coenzyme A + Hydrogen ion + 2-Methylcitric acid + Methylcitric acid Water + Oxalacetic acid + Propionyl-CoA <> Methylcitric acid + Coenzyme A + Hydrogen ion + (2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate Acetyl-CoA + Water + Oxalacetic acid <> Citric acid + Coenzyme A + Hydrogen ion L-Malic acid + FAD <> FADH2 + Oxalacetic acid L-Malic acid + Quinone <> Oxalacetic acid + Hydroquinone Carbon dioxide + Water + Phosphoenolpyruvic acid <> Hydrogen ion + Oxalacetic acid + Phosphate + Hydrogen carbonate Adenosine triphosphate + Oxalacetic acid <> ADP + Carbon dioxide + Phosphoenolpyruvic acid Acetyl-CoA + Water + Oxalacetic acid <> Citric acid + Coenzyme A + Hydrogen ion L-Malic acid + FAD <> FADH2 + Oxalacetic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMPDB Pathways: |
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KEGG Pathways: |
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EcoCyc Pathways: |
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Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References: |
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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 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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External Links: |
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Enzymes
- General function:
- Involved in transferase activity
- Specific function:
- L-aspartate + 2-oxoglutarate = oxaloacetate + L-glutamate
- Gene Name:
- aspC
- Uniprot ID:
- P00509
- Molecular weight:
- 43573
Reactions
L-aspartate + 2-oxoglutarate = oxaloacetate + L-glutamate. |
- General function:
- Involved in phosphoenolpyruvate carboxylase activity
- Specific function:
- Through the carboxylation of phosphoenolpyruvate (PEP) it forms oxaloacetate, a four-carbon dicarboxylic acid source for the tricarboxylic acid cycle
- Gene Name:
- ppc
- Uniprot ID:
- P00864
- Molecular weight:
- 99062
Reactions
Phosphate + oxaloacetate = H(2)O + phosphoenolpyruvate + HCO(3)(-). |
- General function:
- Involved in transferase activity
- Specific function:
- An aromatic amino acid + 2-oxoglutarate = an aromatic oxo acid + L-glutamate
- Gene Name:
- tyrB
- Uniprot ID:
- P04693
- Molecular weight:
- 43537
Reactions
An aromatic amino acid + 2-oxoglutarate = an aromatic oxo acid + L-glutamate. |
- General function:
- Involved in lyase activity
- Specific function:
- (R,R)-tartrate = oxaloacetate + H(2)O
- Gene Name:
- ttdA
- Uniprot ID:
- P05847
- Molecular weight:
- 32733
Reactions
(R,R)-tartrate = oxaloacetate + H(2)O. |
- General function:
- Involved in catalytic activity
- Specific function:
- 4-hydroxy-2-oxoglutarate = pyruvate + glyoxylate
- Gene Name:
- eda
- Uniprot ID:
- P0A955
- Molecular weight:
- 22284
Reactions
4-hydroxy-2-oxoglutarate = pyruvate + glyoxylate. |
2-dehydro-3-deoxy-D-gluconate 6-phosphate = pyruvate + D-glyceraldehyde 3-phosphate. |
- General function:
- Involved in carbon-carbon lyase activity
- Specific function:
- Represents a citryl-ACP lyase
- Gene Name:
- citE
- Uniprot ID:
- P0A9I1
- Molecular weight:
- 33109
Reactions
Citrate = acetate + oxaloacetate. |
(3S)-citryl-CoA = acetyl-CoA + oxaloacetate. |
- General function:
- Involved in transferase activity, transferring acyl groups, acyl groups converted into alkyl on transfer
- Specific function:
- Acetyl-CoA + H(2)O + oxaloacetate = citrate + CoA
- Gene Name:
- gltA
- Uniprot ID:
- P0ABH7
- Molecular weight:
- 48015
Reactions
Acetyl-CoA + H(2)O + oxaloacetate = citrate + CoA. |
- General function:
- Involved in hydro-lyase activity
- Specific function:
- (R,R)-tartrate = oxaloacetate + H(2)O
- Gene Name:
- ttdB
- Uniprot ID:
- P0AC35
- Molecular weight:
- 22679
Reactions
(R,R)-tartrate = oxaloacetate + H(2)O. |
- General function:
- Involved in electron carrier activity
- Specific function:
- Catalyzes the oxidation of L-aspartate to iminoaspartate
- Gene Name:
- nadB
- Uniprot ID:
- P10902
- Molecular weight:
- 60337
Reactions
L-aspartate + O(2) = iminosuccinate + H(2)O(2). |
- General function:
- Involved in lyase activity
- Specific function:
- It functions in the generation of fumarate for use as an anaerobic electron acceptor
- Gene Name:
- fumB
- Uniprot ID:
- P14407
- Molecular weight:
- 60105
Reactions
(S)-malate = fumarate + H(2)O. |
- General function:
- Involved in phosphoenolpyruvate carboxykinase (ATP) activity
- Specific function:
- ATP + oxaloacetate = ADP + phosphoenolpyruvate + CO(2)
- Gene Name:
- pckA
- Uniprot ID:
- P22259
- Molecular weight:
- 59643
Reactions
ATP + oxaloacetate = ADP + phosphoenolpyruvate + CO(2). |
- General function:
- Involved in transferase activity, transferring acyl groups, acyl groups converted into alkyl on transfer
- Specific function:
- Catalyzes the synthesis of 2-methylcitrate from propionyl-CoA and oxaloacetate. Also catalyzes the condensation of oxaloacetate with acetyl-CoA but with a lower specificity
- Gene Name:
- prpC
- Uniprot ID:
- P31660
- Molecular weight:
- 43102
Reactions
Propanoyl-CoA + H(2)O + oxaloacetate = (2R,3S)-2-hydroxybutane-1,2,3-tricarboxylate + CoA. |
- General function:
- Involved in malate dehydrogenase (quinone) activity
- Specific function:
- (S)-malate + a quinone = oxaloacetate + reduced quinone
- Gene Name:
- mqo
- Uniprot ID:
- P33940
- Molecular weight:
- 60229
Reactions
(S)-malate + a quinone = oxaloacetate + reduced quinone. |
- General function:
- Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
- Specific function:
- Catalyzes the reversible oxidation of malate to oxaloacetate
- Gene Name:
- mdh
- Uniprot ID:
- P61889
- Molecular weight:
- 32337
Reactions
(S)-malate + NAD(+) = oxaloacetate + NADH. |
- General function:
- Energy production and conversion
- Specific function:
- Covalent carrier of the coenzyme of citrate lyase
- Gene Name:
- citD
- Uniprot ID:
- P69330
- Molecular weight:
- 10689
- General function:
- Involved in citrate CoA-transferase activity
- Specific function:
- Represents a citrate:acetyl-ACP transferase
- Gene Name:
- citF
- Uniprot ID:
- P75726
- Molecular weight:
- 55172
Reactions
Citrate = acetate + oxaloacetate. |
Acetyl-CoA + citrate = acetate + (3S)-citryl-CoA. |
- General function:
- Involved in prosthetic group biosynthetic process
- Specific function:
- Transfers 2-(5''-triphosphoribosyl)-3'- dephosphocoenzyme-A on a serine residue to the apo-acyl carrier protein (gamma chain) of the citrate lyase to yield holo-acyl carrier protein
- Gene Name:
- citX
- Uniprot ID:
- P0A6G5
- Molecular weight:
- 20270
Reactions
2'-(5-triphosphoribosyl)-3'-dephospho-CoA + citrate lyase apo-[acyl-carrier-protein] = citrate lyase holo-[acyl-carrier-protein] + diphosphate. |