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Preferred IUPAC name (2S,3R,4E)-2-Aminooctadec-4-ene-1,3-diol | |
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ECHA InfoCard | 100.004.230 |
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Properties | |
Chemical formula | C18H37NO2 |
Molar mass | 299.499 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is YN ?) Infobox references |
Sphingosine (2-amino-4-trans-octadecene-1,3-diol) is an 18-carbon amino alcohol with an unsaturated hydrocarbon chain, which forms a primary part of sphingolipids, a class of cell membrane lipids that include sphingomyelin, an important phospholipid.
Sphingosine can be phosphorylated in vivo via two kinases, sphingosine kinase type 1 and sphingosine kinase type 2. This leads to the formation of sphingosine-1-phosphate, a potent signaling lipid.
Sphingolipid metabolites, such as ceramides, sphingosine and sphingosine-1-phosphate, are lipid signaling molecules involved in diverse cellular processes.
Sphingosine is synthesized from palmitoyl CoA and serine in a condensation required to yield dihydrosphingosine.
Dehydrosphingosine is then reduced by NADPH to dihydrosphingosine (sphinganine), acylated to dihydroceramide finally oxidized by FAD to ceramide. Sphingosine is then solely formed via degradation of sphingolipid in the lysosome.
Glycoconjugates, lipids, and glycolipids: sphingolipids and glycosphingolipids, and metabolic intermediates | |||||||||||
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Ceramide | |||||||||||
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See also: Receptor/signaling modulators |
Authority control databases: National |
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