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- Name help_outline leukotriene E4 Identifier CHEBI:57462 Charge -1 Formula C23H36NO5S InChIKeyhelp_outline OTZRAYGBFWZKMX-FRFVZSDQSA-M SMILEShelp_outline CCCCC\C=C/C\C=C/C=C/C=C/[C@@H](SC[C@H]([NH3+])C([O-])=O)[C@@H](O)CCCC([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 NADPH Identifier CHEBI:57783 (Beilstein: 10411862) help_outline Charge -4 Formula C21H26N7O17P3 InChIKeyhelp_outline ACFIXJIJDZMPPO-NNYOXOHSSA-J SMILEShelp_outline NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OC[C@H]2O[C@H]([C@H](OP([O-])([O-])=O)[C@@H]2O)n2cnc3c(N)ncnc23)[C@@H](O)[C@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 1,288 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 2,727 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline H+ Identifier CHEBI:15378 Charge 1 Formula H InChIKeyhelp_outline GPRLSGONYQIRFK-UHFFFAOYSA-N SMILEShelp_outline [H+] 2D coordinates Mol file for the small molecule Search links Involved in 9,521 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline 20-hydroxy-leukotriene E4 Identifier CHEBI:58584 Charge -1 Formula C23H36NO6S InChIKeyhelp_outline BJRMBXPQAMDCMG-CMJQBAFXSA-M SMILEShelp_outline [NH3+][C@@H](CS[C@H](\C=C\C=C\C=C/C\C=C/CCCCCO)[C@@H](O)CCCC([O-])=O)C([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
- Name help_outline NADP+ Identifier CHEBI:58349 Charge -3 Formula C21H25N7O17P3 InChIKeyhelp_outline XJLXINKUBYWONI-NNYOXOHSSA-K SMILEShelp_outline NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OC[C@H]2O[C@H]([C@H](OP([O-])([O-])=O)[C@@H]2O)n2cnc3c(N)ncnc23)[C@@H](O)[C@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 1,294 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline H2O Identifier CHEBI:15377 (CAS: 7732-18-5) help_outline Charge 0 Formula H2O InChIKeyhelp_outline XLYOFNOQVPJJNP-UHFFFAOYSA-N SMILEShelp_outline [H]O[H] 2D coordinates Mol file for the small molecule Search links Involved in 6,264 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:24120 | RHEA:24121 | RHEA:24122 | RHEA:24123 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
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Publications
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Omega-oxidation of cysteine-containing leukotrienes by rat-liver microsomes. Isolation and characterization of omega-hydroxy and omega-carboxy metabolites of leukotriene E4 and N-acetylleukotriene E4.
Orning L.
Leukotriene E4 was metabolized to two polar products by rat liver microsomes. These products were characterized by physico-chemical and chemical techniques. The chemical structures, (5S, 6R)-5,20-dihydroxy-6S-cysteinyl-7,9-trans-11,14-cis-icosatetraenoic acid (omega-hydroxy-leukotriene E4) and (5S ... >> More
Leukotriene E4 was metabolized to two polar products by rat liver microsomes. These products were characterized by physico-chemical and chemical techniques. The chemical structures, (5S, 6R)-5,20-dihydroxy-6S-cysteinyl-7,9-trans-11,14-cis-icosatetraenoic acid (omega-hydroxy-leukotriene E4) and (5S, 6R)-5-hydroxy-6S-cysteinyl-7,9-trans-11,14-cis-icosatetraen-1,20-d ioic acid (omega-carboxy-leukotriene E4) suggested that leukotriene E4 was transformed by an omega-hydroxylase and omega-hydroxyleukotriene E dehydrogenase in sequence. N-Acetyl-leukotriene E4 was also transformed by these enzymes, but at a rate six times lower than leukotriene E4. The products formed from N-acetylleukotriene E4 were characterized as being N-acetyl-omega-hydroxy-leukotriene E4 and N-acetyl-omega-carboxy-leukotriene E4. Other substrates were 11-trans-leukotriene E4 and N-acetyl-11-trans-leukotriene E4. In contrast, leukotrienes C4 and D4 were not converted into omega-oxidized metabolites. The leukotriene E omega-hydroxylase reaction required NADPH and molecular oxygen as cofactors, and was most rapidly catalyzed by liver microsomes. Liver cytosol, fortified with NAD+, converted omega-hydroxyleukotriene E4 and N-acetyl-omega-hydroxy-leukotriene E4 into omega-carboxy metabolites. Microsomes contained at least 18 times less omega-hydroxy-leukotriene E dehydrogenase activity than did cytosol. Liver microsomes supplemented with acetyl-coenzyme A converted omega-hydroxy and omega-carboxy-leukotriene E4 into the corresponding N-acetyl derivatives. The novel enzyme, leukotriene E omega-hydroxylase, which is described here is distinct from a previously described leukotriene B omega-hydroxylase based on substrate competition and kinetic data. << Less