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- Name help_outline 1-(1Z-octadecenyl)-sn-glycero-3-phosphoethanolamine Identifier CHEBI:229972 Charge 0 Formula C23H48NO6P InChIKeyhelp_outline KACDZDULGKPXHT-HIVNOOBXSA-N SMILEShelp_outline P(OC[C@@H](CO/C=C\CCCCCCCCCCCCCCCC)O)(=O)(OCC[NH3+])[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 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine Identifier CHEBI:74965 Charge 0 Formula C46H84NO8P InChIKeyhelp_outline PSVRFUPOQYJOOZ-QNPWAGBNSA-N SMILEShelp_outline O=C(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)O[C@@H](COP(OCC[N+](C)(C)C)(=O)[O-])COC(=O)CCCCCCCCCCCCCCCCC 2D coordinates Mol file for the small molecule Search links Involved in 9 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline 1-(1Z-octadecenyl)-2-(5Z,8Z,11Z,14Z- eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine Identifier CHEBI:78342 Charge 0 Formula C43H78NO7P InChIKeyhelp_outline URPXXNCTXCOATD-FXMFQVEGSA-N SMILEShelp_outline CCCCCCCCCCCCCCCC\C=C/OC[C@H](COP([O-])(=O)OCC[NH3+])OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC 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 1-octadecanoyl-sn-glycero-3-phosphocholine Identifier CHEBI:73858 (CAS: 5655-17-4) help_outline Charge 0 Formula C26H54NO7P InChIKeyhelp_outline IHNKQIMGVNPMTC-RUZDIDTESA-N SMILEShelp_outline CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C 2D coordinates Mol file for the small molecule Search links Involved in 26 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:79431 | RHEA:79432 | RHEA:79433 | RHEA:79434 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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Related reactions help_outline
More general form(s) of this reaction
Publications
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TMEM164 is an acyltransferase that forms ferroptotic C20:4 ether phospholipids.
Reed A., Ware T., Li H., Fernando Bazan J., Cravatt B.F.
Ferroptosis is an iron-dependent form of cell death driven by oxidation of polyunsaturated fatty acid (PUFA) phospholipids. Large-scale genetic screens have uncovered a specialized role for PUFA ether phospholipids (ePLs) in promoting ferroptosis. Understanding of the enzymes involved in PUFA-ePL ... >> More
Ferroptosis is an iron-dependent form of cell death driven by oxidation of polyunsaturated fatty acid (PUFA) phospholipids. Large-scale genetic screens have uncovered a specialized role for PUFA ether phospholipids (ePLs) in promoting ferroptosis. Understanding of the enzymes involved in PUFA-ePL production, however, remains incomplete. Here we show, using a combination of pathway mining of genetic dependency maps, AlphaFold-guided structure predictions and targeted lipidomics, that the uncharacterized transmembrane protein TMEM164-the genetic ablation of which has been shown to protect cells from ferroptosis-is a cysteine active center enzyme that selectively transfers C20:4 acyl chains from phosphatidylcholine to lyso-ePLs to produce PUFA ePLs. Genetic deletion of TMEM164 across a set of ferroptosis-sensitive cancer cell lines caused selective reductions in C20:4 ePLs with minimal effects on C20:4 diacyl PLs, and this lipid profile produced a variable range of protection from ferroptosis, supportive of an important but contextualized role for C20:4 ePLs in this form of cell death. << Less