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- Name help_outline 2-[(15R)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoyl]-sn-glycero-3-phosphocholine Identifier CHEBI:137583 Charge 0 Formula C28H50NO8P InChIKeyhelp_outline UGWAFZVUHJCWOQ-FWJSUUQISA-N SMILEShelp_outline O=C(O[C@H](CO)COP(=O)([O-])OCC[N+](C)(C)C)CCC/C=C\C/C=C\C/C=C\C=C\[C@@H](CCCCC)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 H2O Identifier CHEBI:15377 (Beilstein: 3587155; 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 6,048 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline (15R)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoate Identifier CHEBI:78837 Charge -1 Formula C20H31O3 InChIKeyhelp_outline JSFATNQSLKRBCI-UDQWCNDOSA-M SMILEShelp_outline CCCCC[C@@H](O)\C=C\C=C/C\C=C/C\C=C/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 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 9,176 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline sn-glycerol 3-phosphocholine Identifier CHEBI:16870 (Beilstein: 6062450; CAS: 28319-77-9) help_outline Charge 0 Formula C8H20NO6P InChIKeyhelp_outline SUHOQUVVVLNYQR-MRVPVSSYSA-N SMILEShelp_outline C[N+](C)(C)CCOP([O-])(=O)OC[C@H](O)CO 2D coordinates Mol file for the small molecule Search links Involved in 42 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:53696 | RHEA:53697 | RHEA:53698 | RHEA:53699 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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Publications
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Cyclooxygenase-2 Mediated Oxidation of 2-Arachidonoyl-Lysophospholipids Identifies Unknown Lipid Signaling Pathways.
Liu X., Moon S.H., Jenkins C.M., Sims H.F., Gross R.W.
Eicosanoid lipids play important roles in cellular signaling as second messengers in inflammation, immune response, vascular tone, and the CNS. Biosynthesis of eicosanoid lipids proceeds via hydrolysis of esterified arachidonic acid from phospholipids followed by oxidation of the released arachido ... >> More
Eicosanoid lipids play important roles in cellular signaling as second messengers in inflammation, immune response, vascular tone, and the CNS. Biosynthesis of eicosanoid lipids proceeds via hydrolysis of esterified arachidonic acid from phospholipids followed by oxidation of the released arachidonic acid by a variety of enzymes including cyclooxygenases (COX). Herein, we demonstrate the remarkable ability of COX-2, but not COX-1, to directly oxidize 2-arachidonoyl-lysolipids, resulting in the generation of previously unknown classes of eicosanoid-lysolipids, and provide evidence that intracellular lipases can release eicosanoids from their eicosanoid-lysolipid precursors. Importantly, genetic ablation of a phospholipase, iPLA<sub>2</sub>γ, significantly reduced the amounts of these eicosanoid-lysolipids in murine hepatic tissue and fibroblasts. Furthermore, calcium stimulation of wild-type murine lung fibroblasts produced robust increases in these eicosanoid-lysolipids, which were markedly attenuated in iPLA<sub>2</sub>γ<sup>-/-</sup> fibroblasts. Collectively, these results identify an iPLA<sub>2</sub>γ-initiated pathway generating new classes of lipid metabolites with potential signaling functions resulting from the direct COX-2 catalyzed oxidation of 2-arachidonoyl-lysolipids. << Less
Cell Chem. Biol. 23:1217-1227(2016) [PubMed] [EuropePMC]
This publication is cited by 14 other entries.