Record Information |
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Version | 4.0 |
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Status | Expected but not Quantified |
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Creation Date | 2006-05-22 14:17:34 UTC |
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Update Date | 2020-09-15 18:51:49 UTC |
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HMDB ID | HMDB0002052 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Maleylacetoacetic acid |
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Description | Maleylacetoacetic acid, also known as 4-maleylacetoacetate, belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain. Maleylacetoacetic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Maleylacetoacetic acid exists in all living organisms, ranging from bacteria to humans. Within humans, maleylacetoacetic acid participates in a number of enzymatic reactions. In particular, maleylacetoacetic acid can be converted into 4-fumarylacetoacetic acid through its interaction with the enzyme maleylacetoacetate isomerase. In addition, maleylacetoacetic acid can be biosynthesized from homogentisic acid; which is mediated by the enzyme homogentisate 1,2-dioxygenase. 4-Maleylacetoacetate (4-maleylacetoacetate) is an intermediate in the metabolism of tyrosine. In humans, maleylacetoacetic acid is involved in the metabolic disorder called tyrosinemia type I. Maleylacetoacetic acid is a potentially toxic compound. |
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Structure | |
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Synonyms | Value | Source |
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4-Maleylacetoacetate | ChEBI | 4-Maleylacetoacetic acid | Kegg | Maleylacetoacetate | Generator | (2Z)-4,6-Dioxo-2-octenedioic acid | HMDB | Maleylacetoacetic acid | HMDB |
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Chemical Formula | C8H8O6 |
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Average Molecular Weight | 200.1455 |
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Monoisotopic Molecular Weight | 200.032087988 |
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IUPAC Name | (2Z)-4,6-dioxooct-2-enedioic acid |
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Traditional Name | maleylacetoacetic acid |
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CAS Registry Number | 5698-52-2 |
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SMILES | OC(=O)CC(=O)CC(=O)\C=C/C(O)=O |
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InChI Identifier | InChI=1S/C8H8O6/c9-5(1-2-7(11)12)3-6(10)4-8(13)14/h1-2H,3-4H2,(H,11,12)(H,13,14)/b2-1- |
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InChI Key | GACSIVHAIFQKTC-UPHRSURJSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain. |
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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 | Medium-chain keto acids and derivatives |
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Direct Parent | Medium-chain keto acids and derivatives |
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Alternative Parents | |
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Substituents | - Medium-chain keto acid
- Beta-keto acid
- 1,3-diketone
- Beta-hydroxy ketone
- Dicarboxylic acid or derivatives
- Unsaturated fatty acid
- 1,3-dicarbonyl compound
- Fatty acyl
- Enone
- Acryloyl-group
- Alpha,beta-unsaturated ketone
- Ketone
- Carboxylic acid
- Carboxylic acid derivative
- Organooxygen compound
- Organic oxide
- Organic oxygen compound
- Carbonyl group
- 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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Disposition | Source: Biological location: |
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Process | Naturally occurring process: |
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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 | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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| Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0007-9300000000-7b2ae90eb353073cb652 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-05bu-7092000000-254fb0c9b4683fd48ef1 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0fsi-1920000000-f36f976fb4a0271e936b | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-6900000000-692cbcc9f99aac913e42 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00rj-9200000000-8e21be4180492b988f54 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4j-1900000000-ea634f49698a94be6311 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-5900000000-4d5261faac7c9dc29c36 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-9500000000-17b0a81ad882f626ac2a | Spectrum |
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General References | - Kvittingen EA, Halvorsen S, Jellum E: Deficient fumarylacetoacetate fumarylhydrolase activity in lymphocytes and fibroblasts from patients with hereditary tyrosinemia. Pediatr Res. 1983 Jul;17(7):541-4. [PubMed:6622096 ]
- Gray RG, Patrick AD, Preston FE, Whitfield MF: Acute hereditary tyrosinaemia type I: clinical, biochemical and haematological studies in twins. J Inherit Metab Dis. 1981;4(1):37-40. [PubMed:6785523 ]
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