| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 22:26:59 UTC |
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| Update Date | 2020-06-04 19:53:36 UTC |
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| BMDB ID | BMDB0000223 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Oxalacetic acid |
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| Description | Oxalacetic 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. |
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| Structure | |
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| Synonyms | | Value | Source |
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| 2-Oxobutanedioic acid | ChEBI | | 2-Oxosuccinic acid | ChEBI | | 3-Carboxy-3-oxopropanoic acid | ChEBI | | Keto-succinic acid | ChEBI | | Ketosuccinic acid | ChEBI | | OAA | ChEBI | | Oxobutanedioic acid | ChEBI | | Oxosuccinic acid | ChEBI | | Oxaloacetic acid | Kegg | | Keto-oxaloacetate | Kegg | | 2-Oxobutanedioate | Generator | | 2-Oxosuccinate | Generator | | 3-Carboxy-3-oxopropanoate | Generator | | Keto-succinate | Generator | | Ketosuccinate | Generator | | Oxobutanedioate | Generator | | Oxosuccinate | Generator | | Oxaloacetate | Generator | | Keto-oxaloacetic acid | Generator | | Oxalacetate | Generator | | 2-Ketosuccinate | HMDB | | 2-Ketosuccinic acid | HMDB | | a-Ketosuccinate | HMDB | | a-Ketosuccinic acid | HMDB | | alpha-Ketosuccinate | HMDB | | alpha-Ketosuccinic acid | HMDB | | Oxaloethanoate | HMDB | | Oxaloethanoic acid | HMDB | | Acid, oxaloacetic | HMDB | | Acid, oxalacetic | HMDB | | 2 Ketosuccinic acid | HMDB | | 2 oxo Butanedioic acid | HMDB | | 2-oxo-Butanedioic acid | HMDB |
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| Chemical Formula | C4H4O5 |
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| Average Molecular Weight | 132.0716 |
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| Monoisotopic Molecular Weight | 132.005873238 |
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| IUPAC Name | 2-oxobutanedioic acid |
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| Traditional Name | oxalacetate |
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| CAS Registry Number | 328-42-7 |
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| SMILES | OC(=O)CC(=O)C(O)=O |
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| InChI Identifier | InChI=1S/C4H4O5/c5-2(4(8)9)1-3(6)7/h1H2,(H,6,7)(H,8,9) |
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| InChI Key | KHPXUQMNIQBQEV-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Organic acids and derivatives |
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| Class | Keto acids and derivatives |
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| Sub Class | Short-chain keto acids and derivatives |
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| Direct Parent | Short-chain keto acids and derivatives |
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| Alternative Parents | |
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| 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
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Status | Detected and Quantified |
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| Origin | |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | - Cytoplasm
- Mitochondria
- Peroxisome
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | 161 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 134 mg/mL | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | |
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| Biological Properties |
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| Cellular Locations | - Cytoplasm
- Mitochondria
- Peroxisome
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| Biospecimen Locations | |
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| Pathways | |
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| Normal Concentrations |
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| Liver | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 7 - 24 uM | Not Specified | Not Specified | Normal | | details |
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| Abnormal Concentrations |
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| Not Available |
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| External Links |
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| HMDB ID | HMDB0000223 |
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| DrugBank ID | Not Available |
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| Phenol Explorer Compound ID | Not Available |
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| FooDB ID | FDB031075 |
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| KNApSAcK ID | C00001197 |
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| Chemspider ID | 945 |
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| KEGG Compound ID | C00036 |
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| BioCyc ID | OXALACETIC_ACID |
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| BiGG ID | 33604 |
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| Wikipedia Link | Oxaloacetic_acid |
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| METLIN ID | 123 |
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| PubChem Compound | 970 |
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| PDB ID | Not Available |
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| ChEBI ID | 30744 |
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| 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. |
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| Material Safety Data Sheet (MSDS) | Not Available |
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| General References | - 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 ]
- 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 ]
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