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- Name help_outline N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-alanine Identifier CHEBI:132071 Charge -1 Formula C23H36NO3 InChIKeyhelp_outline ZECSOKFEQQDUCP-GDYZQIPQSA-M SMILEShelp_outline C(CCC)C/C=C\C/C=C\C/C=C\C/C=C\CCCC(N[C@H](C([O-])=O)C)=O 2D coordinates Mol file for the small molecule Search links Involved in 2 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-alanine Identifier CHEBI:132074 Charge -1 Formula C23H36NO5 InChIKeyhelp_outline HEDNIHSKHKFUON-RTYQQCFVSA-M SMILEShelp_outline C(=C/[C@H](C/C=C\CCCCC)OO)\C=C/C/C=C\CCCC(=O)N[C@H](C([O-])=O)C 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:50172 | RHEA:50173 | RHEA:50174 | RHEA:50175 | |
|---|---|---|---|---|
| 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 lipoamino acids and vanilloids by lipoxygenases and cyclooxygenases.
Prusakiewicz J.J., Turman M.V., Vila A., Ball H.L., Al-Mestarihi A.H., Di Marzo V., Marnett L.J.
The lipoamino acids and endovanilloids have multiple roles in nociception, pain, and inflammation, yet their biological reactivity has not been fully characterized. Cyclooxygenases (COXs) and lipoxygenases (LOs) oxygenate polyunsaturated fatty acids to generate signaling molecules. The ability of ... >> More
The lipoamino acids and endovanilloids have multiple roles in nociception, pain, and inflammation, yet their biological reactivity has not been fully characterized. Cyclooxygenases (COXs) and lipoxygenases (LOs) oxygenate polyunsaturated fatty acids to generate signaling molecules. The ability of COXs and LOs to oxygenate arachidonyl-derived lipoamino acids and vanilloids was investigated. COX-1 and COX-2 were able to minimally metabolize many of these species. However, the lipoamino acids were efficiently oxygenated by 12S- and 15S-LOs. The kinetics and products of oxygenation by LOs were characterized. Whereas 15S-LOs retained positional specificity of oxygenation with these novel substrates, platelet-type 12S-LO acted as a 12/15-LO. Fatty acid oxygenases may play an important role in the metabolic inactivation of lipoamino acids or vanilloids or may convert them to bioactive derivatives. << Less
Arch. Biochem. Biophys. 464:260-268(2007) [PubMed] [EuropePMC]
This publication is cited by 6 other entries.