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4-Maleylacetoacetic acid
4-Maleylacetoacetate (4-maleylacetoacetatic acid) is an intermediate in the metabolism of tyrosine. It is converted to fumarylacetoacetic acid by the enzyme 4-maleylacetoacetate cis-trans-isomerase.
| Column 1 | Column 2 |
|---|---|
| Preferred IUPAC name | |
| (2Z)-4,6-Dioxooct-2-enedioic acid | |
| Other names | |
| 4-Maleylacetoacetate | |
| CAS Number | .mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}5698-52-2 Y |
| 3D model (JSmol) | Interactive image |
| ChEBI | CHEBI:47904 Y |
| ChEMBL | ChEMBL1743220 Y |
| ChemSpider | 4444078 Y |
| KEGG | C01036 Y |
| PubChem CID | 5280393 |
| UNII | 5ET93TW8TE Y |
| CompTox Dashboard (EPA) | DTXSID201299688 |
| InChI | |
| 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- YKey: GACSIVHAIFQKTC-UPHRSURJSA-N Y | |
| SMILES | |
| O=C(/C=C\C(=O)O)CC(=O)CC(=O)O | |
| Chemical formula | C8H8O6 |
| Molar mass | 200.146 g·mol−1 |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Infobox references | |
4-Maleylacetoacetate (4-maleylacetoacetatic acid) is an intermediate in the metabolism of tyrosine. It is converted to fumarylacetoacetic acid by the enzyme 4-maleylacetoacetate cis-trans-isomerase.
The amino acid tyrosine is metabolised in a series of reactions, one of which is catalysed by homogentisate 1,2-dioxygenase. This converts the intermediate homogentisic acid into 4-maleylacetoacetic acid.
The enzyme maleylacetoacetate isomerase converts 4-maleylacetoacetic acid to its geometric isomer, fumarylacetoacetic acid.
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