2-Amino-3-carboxymuconic semialdehyde

2-amino-3-carboxymuconic semialdehyde.svg Skeletal formula of 2-amino-3-carboxymuconic semialdehyde 2-Amino-3-carboxymuconic-semialdehyde-zwitterion-3D-balls.png Ball-and-stick model of the 2-amino-3-carboxymuconic semialdehyde molecule as a zwitterion (2Z)-2-Amino-3-[(1Z)-3-oxoprop-1-en-1-yl]but-2-enedioic acid correct CAS 16597-58-3 C04409 5280673 correct chemspider 4444266 correct EBI 994 correct chemspider 1S/C7H7NO5/c8-5(7(12)13)4(6(10)11)2-1-3-9/h1-3H,8H2,(H,10,11)(H,12,13)/b2-1-,5-4- correct chemspider KACPVQQHDVBVFC-OIFXTYEKSA-N C(=CC(=C(C(=O)O)N)C(=O)O)C=O 7 7 1 5 185.13 g/mol 1.527 g/mL 389 189 2-Amino-3-carboxymuconic semialdehydeUniProt https://www.uniprot.org/uniprotkb/Q8TDX5/entry 2022-11-22 www.uniprot.orgHuman Metabolome Database: Showing metabocard for 2-Amino-3-carboxymuconic acid semialdehyde (HMDB0001330) https://hmdb.ca/metabolites/HMDB0001330 2022-11-22 hmdb.ca is an intermediate in the metabolism of tryptophan in the kynurenine pathway. Quinolinic acid is a neurotoxin formed nonenzymatically from 2-amino-3-carboxymuconic semialdehyde in mammalian tissues. 2-Amino-3-carboxymuconic semialdehyde is enzymatically converted to picolinic acid via 2-aminomuconic semialdehyde. Biosynthesis The enzyme 3-hydroxyanthranilate 3,4-dioxygenase uses oxygen to cleave the aromatic ring of 3-hydroxyanthranilic acid, giving 2-amino-3-carboxymuconic semialdehyde.Decker R.H. Kang H.H. Leach Franklin R. Henderson L.M. Purification and Properties of 3-Hydroxyanthranilic Acid Oxidase Journal of Biological Chemistry 1961 236 11 3076–3082 10.1016/S0021-9258(19)76432-1 free 50% 3-Hydroxyanthranilic acid O2 Q2823201 2-amino-3-carboxymuconic semialdehyde Metabolism The kynurenine pathway of tryptophan catabolism leads to nicotinamide adenine dinucleotide and supplies the nicotinic acid component of that cofactor.Savitz J The kynurenine pathway: a finger in every pie. Molecular Psychiatry 25 January 2020 25 1 131–147 10.1038/s41380-019-0414-4 30980044 6790159 In this pathway, quinolinic acid is produced spontaneously from the intermediate semialdehyde as its amine cyclises with the aldehyde, losing a molecule of water:Schwarcz Robert Bruno John P. Muchowski Paul J. Wu Hui-Qiu Kynurenines in the mammalian brain: When physiology meets pathology Nature Reviews Neuroscience 2012 13 7 465–477 10.1038/nrn3257 22678511 3681811 45% Q2823201 2-amino-3-carboxymuconic semialdehyde 1.2 H2O quinolinic acid Alternatively, 2-amino-3-carboxymuconic semialdehyde can be acted on by the enzyme aminocarboxymuconate-semialdehyde decarboxylase to give 2-aminomuconic semialdehyde, an unstable open-chain precursor of picolinic acid.He Z. Spain J. 1999-08-01 Preparation of 2-aminomuconate from 2-aminophenol by coupled enzymatic dioxygenation and dehydrogenation reactions Journal of Industrial Microbiology & Biotechnology 23 2 138–142 10.1038/sj.jim.2900705 1476-5535 10510494 1091252 free Zeng Ting Liang Yanshan Chen Jinyao Cao Guodong Yang Zhu Zhao Xingchen Tian Jinglin Xin Xiong Lei Bo Cai Zongwei 2021-09-01 Urinary metabolic characterization with nephrotoxicity for residents under cadmium exposure Environment International en 154 106646 10.1016/j.envint.2021.106646 34049269 0160-4120 free 2021EnInt.15406646Z Davis Ian Yang Yu Wherritt Daniel Liu Aimin Reassignment of the human aldehyde dehydrogenase ALDH8A1 (ALDH12) to the kynurenine pathway in tryptophan catabolism Journal of Biological Chemistry 2018 293 25 9594–9603 10.1074/jbc.RA118.003320 free 29703752 6016481 70% Q2823201 2-Amino-3-carboxymuconic semialdehyde CO2 Enzymic 2-Aminomuconic semialdehyde H2O Spontaneous Picolinic acid References Category:Alpha-amino acids Category:Beta-amino acids Category:Conjugated aldehydes Category:Dicarboxylic acids Category:Enoic acids