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- Name help_outline 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine Identifier CHEBI:72999 (CAS: 63-89-8,2644-64-6) help_outline Charge 0 Formula C40H80NO8P InChIKeyhelp_outline KILNVBDSWZSGLL-KXQOOQHDSA-N SMILEShelp_outline CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC 2D coordinates Mol file for the small molecule Search links Involved in 23 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline 1-(1Z-octadecenyl)-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine Identifier CHEBI:78340 Charge 0 Formula C41H80NO7P InChIKeyhelp_outline XVYPOHCSLJZFED-QZEVRULJSA-N SMILEShelp_outline CCCCCCCCCCCCCCCC\C=C/OC[C@H](COP([O-])(=O)OCC[NH3+])OC(=O)CCCCCCC\C=C/CCCCCCCC 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 1-O-(1Z-octadecenoyl)-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-N-hexadecanoyl-ethanolamine Identifier CHEBI:138663 Charge -1 Formula C57H109NO8P InChIKeyhelp_outline UQKONGBTZFNBQX-SFVTZJANSA-M SMILEShelp_outline C(CCCCCCC/C=C\CCCCCCCC)(=O)O[C@@H](COP(=O)(OCCNC(CCCCCCCCCCCCCCC)=O)[O-])CO/C=C\CCCCCCCCCCCCCCCC 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 2-hexadecanoyl-sn-glycero-3-phosphocholine Identifier CHEBI:76078 Charge 0 Formula C24H50NO7P InChIKeyhelp_outline NEGQHKSYEYVFTD-HSZRJFAPSA-N SMILEShelp_outline CCCCCCCCCCCCCCCC(=O)O[C@H](CO)COP([O-])(=O)OCC[N+](C)(C)C 2D coordinates Mol file for the small molecule Search links Involved in 13 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
Cross-references
| RHEA:63592 | RHEA:63593 | RHEA:63594 | RHEA:63595 | |
|---|---|---|---|---|
| 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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Phosphatidylserine-stimulated production of N-acyl-phosphatidylethanolamines by Ca2+-dependent N-acyltransferase.
Hussain Z., Uyama T., Kawai K., Binte Mustafiz S.S., Tsuboi K., Araki N., Ueda N.
N-acyl-phosphatidylethanolamine (NAPE) is known to be a precursor for various bioactive N-acylethanolamines including the endocannabinoid anandamide. NAPE is produced in mammals through the transfer of an acyl chain from certain glycerophospholipids to phosphatidylethanolamine (PE) by Ca<sup>2+</s ... >> More
N-acyl-phosphatidylethanolamine (NAPE) is known to be a precursor for various bioactive N-acylethanolamines including the endocannabinoid anandamide. NAPE is produced in mammals through the transfer of an acyl chain from certain glycerophospholipids to phosphatidylethanolamine (PE) by Ca<sup>2+</sup>-dependent or -independent N-acyltransferases. The ε isoform of mouse cytosolic phospholipase A<sub>2</sub> (cPLA<sub>2</sub>ε) was recently identified as a Ca<sup>2+</sup>-dependent N-acyltransferase (Ca-NAT). In the present study, we first showed that two isoforms of human cPLA<sub>2</sub>ε function as Ca-NAT. We next purified both mouse recombinant cPLA<sub>2</sub>ε and its two human orthologues to examine their catalytic properties. The enzyme absolutely required Ca<sup>2+</sup> for its activity and the activity was enhanced by phosphatidylserine (PS). PS enhanced the activity 25-fold in the presence of 1 mM CaCl<sub>2</sub> and lowered the EC<sub>50</sub> value of Ca<sup>2+</sup> >8-fold. Using a PS probe, we showed that cPLA<sub>2</sub>ε largely co-localizes with PS in plasma membrane and organelles involved in the endocytic pathway, further supporting the interaction of cPLA<sub>2</sub>ε with PS in living cells. Finally, we found that the Ca<sup>2+</sup>-ionophore ionomycin increased [<sup>14</sup>C]NAPE levels >10-fold in [<sup>14</sup>C]ethanolamine-labeled cPLA<sub>2</sub>ε-expressing cells while phospholipase A/acyltransferase-1, acting as a Ca<sup>2+</sup>-independent N-acyltransferase, was insensitive to ionomycin for full activity. In conclusion, PS potently stimulated the Ca<sup>2+</sup>-dependent activity and human cPLA<sub>2</sub>ε isoforms also functioned as Ca-NAT. << Less
Biochim. Biophys. Acta 1863:493-502(2018) [PubMed] [EuropePMC]
This publication is cited by 1 other entry.