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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 | Not Available |
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Traditional Name | Not Available |
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CAS Registry Number | 328-42-7 |
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SMILES | Not Available |
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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 | Not Available |
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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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