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- Name help_outline N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-taurine Identifier CHEBI:132060 Charge -1 Formula C22H36NO4S InChIKeyhelp_outline YUNYSWCRLRYOPO-DOFZRALJSA-M SMILEShelp_outline C(CCC)C/C=C\C/C=C\C/C=C\C/C=C\CCCC(NCCS([O-])(=O)=O)=O 2D coordinates Mol file for the small molecule Search links Involved in 3 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline O2 Identifier CHEBI:15379 (CAS: 7782-44-7) help_outline Charge 0 Formula O2 InChIKeyhelp_outline MYMOFIZGZYHOMD-UHFFFAOYSA-N SMILEShelp_outline O=O 2D coordinates Mol file for the small molecule Search links Involved in 2,648 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline N-(12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoyl-taurine Identifier CHEBI:132061 Charge -1 Formula C22H36NO6S InChIKeyhelp_outline SSECKXODJGCASI-KUJNIBRASA-M SMILEShelp_outline C(=C/[C@H](C/C=C\CCCCC)OO)\C=C/C/C=C\CCCC(=O)NCCS([O-])(=O)=O 2D coordinates Mol file for the small molecule Search links Involved in 1 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:50160 | RHEA:50161 | RHEA:50162 | RHEA:50163 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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Publications
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Oxidative metabolism of a fatty acid amide hydrolase-regulated lipid, arachidonoyltaurine.
Turman M.V., Kingsley P.J., Rouzer C.A., Cravatt B.F., Marnett L.J.
A novel class of lipids, N-acyltaurines, was recently discovered in fatty acid amide hydrolase knockout mice. In some peripheral tissues, such as liver and kidney, N-acyltaurines with long, polyunsaturated acyl chains are most prevalent. Polyunsaturated fatty acids are converted to a variety of si ... >> More
A novel class of lipids, N-acyltaurines, was recently discovered in fatty acid amide hydrolase knockout mice. In some peripheral tissues, such as liver and kidney, N-acyltaurines with long, polyunsaturated acyl chains are most prevalent. Polyunsaturated fatty acids are converted to a variety of signaling molecules by cyclooxygenases (COXs) and lipoxygenases (LOXs). The ability of COXs and LOXs to oxygenate arachidonoyltaurine was evaluated to gain insight into the potential metabolic fate of N-acyltaurines. Although arachidonoyltaurine was a poor substrate for COXs, mammalian 12 S- and 15 S-LOXs oxygenated arachidonoyltaurine with similar or better efficiency than arachidonic acid. Products of arachidonoyltaurine oxygenation were characterized by liquid chromatography-tandem mass spectrometry (LC-MS/MS). The positional specificity of single oxygenation was retained for 15 S-LOXs. However, platelet-type 12 S-LOX produced 12- and 15-hydroxyeicosatetraenoyltaurines (HETE-Ts). Furthermore, LOXs generated dihydroxyeicosatetraenoyltaurines (diHETE-Ts). Metabolism of arachidonoyltaurine by murine resident peritoneal macrophages (RPMs) was also profiled. Arachidonoyltaurine was rapidly taken up and converted primarily to 12-HETE-T. Over prolonged incubations, RPMs also generated small amounts of diHETE-T. Oxidative metabolism of polyunsaturated N-acyltaurines may represent a pathway for the generation or termination of novel signaling molecules. << Less
Biochemistry 47:3917-3925(2008) [PubMed] [EuropePMC]
This publication is cited by 1 other entry.