Reaction participants Show >> << Hide
- Name help_outline 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine Identifier CHEBI:74986 Charge 0 Formula C41H78NO8P InChIKeyhelp_outline MWRBNPKJOOWZPW-NYVOMTAGSA-N SMILEShelp_outline O(C(=O)CCCCCCC/C=C\CCCCCCCC)[C@H](COC(=O)CCCCCCC/C=C\CCCCCCCC)COP(=O)([O-])OCC[NH3+] 2D coordinates Mol file for the small molecule Search links Involved in 17 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline an N-acylsphing-4-enine Identifier CHEBI:52639 Charge 0 Formula C19H36NO3R SMILEShelp_outline CCCCCCCCCCCCC\C=C\[C@@H](O)[C@H](CO)NC([*])=O 2D coordinates Mol file for the small molecule Search links Involved in 136 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline an N-acylsphing-4-enine 1-phosphoethanolamine Identifier CHEBI:73203 Charge 0 Formula C21H42N2O6PR SMILEShelp_outline CCCCCCCCCCCCC\C=C\[C@@H](O)[C@H](COP([O-])(=O)OCC[NH3+])NC([*])=O 2D coordinates Mol file for the small molecule Search links Involved in 4 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline 1,2-di-(9Z-octadecenoyl)-sn-glycerol Identifier CHEBI:52333 (CAS: 24529-88-2) help_outline Charge 0 Formula C39H72O5 InChIKeyhelp_outline AFSHUZFNMVJNKX-LLWMBOQKSA-N SMILEShelp_outline CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](CO)OC(=O)CCCCCCC\C=C/CCCCCCCC 2D coordinates Mol file for the small molecule Search links Involved in 28 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:81999 | RHEA:82000 | RHEA:82001 | RHEA:82002 | |
|---|---|---|---|---|
| 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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All members in the sphingomyelin synthase gene family have ceramide phosphoethanolamine synthase activity.
Ding T., Kabir I., Li Y., Lou C., Yazdanyar A., Xu J., Dong J., Zhou H., Park T., Boutjdir M., Li Z., Jiang X.C.
Sphingomyelin synthase-related protein (SMSr) synthesizes the sphingomyelin analog ceramide phosphoethanolamine (CPE) in cells. Previous cell studies indicated that SMSr is involved in ceramide homeostasis and is crucial for cell function. To further examine SMSr function in vivo, we generated Sms ... >> More
Sphingomyelin synthase-related protein (SMSr) synthesizes the sphingomyelin analog ceramide phosphoethanolamine (CPE) in cells. Previous cell studies indicated that SMSr is involved in ceramide homeostasis and is crucial for cell function. To further examine SMSr function in vivo, we generated Smsr KO mice that were fertile and had no obvious phenotypic alterations. Quantitative MS analyses of plasma, liver, and macrophages from the KO mice revealed only marginal changes in CPE and ceramide as well as other sphingolipid levels. Because SMS2 also has CPE synthase activity, we prepared Smsr/Sms2 double KO mice. We found that CPE levels were not significantly changed in macrophages, suggesting that CPE levels are not exclusively dependent on SMSr and SMS2 activities. We then measured CPE levels in Sms1 KO mice and found that Sms1 deficiency also reduced plasma CPE levels. Importantly, we found that expression of Sms1 or Sms2 in SF9 insect cells significantly increased not only SM but also CPE formation, indicating that SMS1 also has CPE synthase activity. Moreover, we measured CPE synthase Km and Vmax for SMS1, SMS2, and SMSr using different NBD ceramides. Our study reveals that all mouse SMS family members (SMSr, SMS1, and SMS2) have CPE synthase activity. However, neither CPE nor SMSr appears to be a critical regulator of ceramide levels in vivo. << Less