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- Name help_outline 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine Identifier CHEBI:73007 Charge 0 Formula C39H76NO8P InChIKeyhelp_outline FHQVHHIBKUMWTI-OTMQOFQLSA-N SMILEShelp_outline [H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[NH3+])OC(=O)CCCCCCC\C=C/CCCCCCCC 2D coordinates Mol file for the small molecule Search links Involved in 10 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 141 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-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycerol Identifier CHEBI:75466 (CAS: 3123-73-7) help_outline Charge 0 Formula C37H70O5 InChIKeyhelp_outline YEJYLHKQOBOSCP-OZKTZCCCSA-N SMILEShelp_outline CCCCCCCCCCCCCCCC(=O)OC[C@H](CO)OC(=O)CCCCCCC\C=C/CCCCCCCC 2D coordinates Mol file for the small molecule Search links Involved in 10 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:41456 | RHEA:41457 | RHEA:41458 | RHEA:41459 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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Publications
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Sphingomyelin synthase SMS2 displays dual activity as ceramide phosphoethanolamine synthase.
Ternes P., Brouwers J.F., van den Dikkenberg J., Holthuis J.C.
Sphingolipids are vital components of eukaryotic membranes involved in the regulation of cell growth, death, intracellular trafficking, and the barrier function of the plasma membrane (PM). While sphingomyelin (SM) is the major sphingolipid in mammals, previous studies indicate that mammalian cell ... >> More
Sphingolipids are vital components of eukaryotic membranes involved in the regulation of cell growth, death, intracellular trafficking, and the barrier function of the plasma membrane (PM). While sphingomyelin (SM) is the major sphingolipid in mammals, previous studies indicate that mammalian cells also produce the SM analog ceramide phosphoethanolamine (CPE). Little is known about the biological role of CPE or the enzyme(s) responsible for CPE biosynthesis. SM production is mediated by the SM synthases SMS1 in the Golgi and SMS2 at the PM, while a closely related enzyme, SMSr, has an unknown biochemical function. We now demonstrate that SMS family members display striking differences in substrate specificity, with SMS1 and SMSr being monofunctional enzymes with SM and CPE synthase activity, respectively, and SMS2 acting as a bifunctional enzyme with both SM and CPE synthase activity. In agreement with the PM residency of SMS2, we show that both SM and CPE synthase activities are enhanced at the surface of SMS2-overexpressing HeLa cells. Our findings reveal an unexpected diversity in substrate specificity among SMS family members that should enable the design of specific inhibitors to target the biological role of each enzyme individually. << Less
J. Lipid Res. 50:2270-2277(2009) [PubMed] [EuropePMC]
This publication is cited by 11 other entries.