Sphingosine

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

Names
Preferred IUPAC name (2S,3R,4E)-2-Aminooctadec-4-ene-1,3-diol
Identifiers
CAS Number	123-78-4 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16393 N
ChEMBL	ChEMBL67166 Y
ChemSpider	4444047 Y
ECHA InfoCard	100.004.230
IUPHAR/BPS	2452
PubChem CID	5280335
UNII	NGZ37HRE42 Y
CompTox Dashboard (EPA)	DTXSID90861763
InChI InChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3/b15-14+/t17-,18+/m0/s1 Y Key: WWUZIQQURGPMPG-KRWOKUGFSA-N Y InChI=1/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3/b15-14+/t17-,18+/m0/s1 Key: WWUZIQQURGPMPG-KRWOKUGFBW
SMILES CCCCCCCCCCCCC/C=C/[C@H]([C@H](CO)N)O
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 [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Functions

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.

Biosynthesis

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 and finally oxidized by FAD to ceramide. Sphingosine is then solely formed via degradation of sphingolipid in the lysosome.

Gallery

• 
  Sphingolipidoses
• 
  General structures of sphingolipids

See also

• Dimethylsphingosine
• Fingolimod

Literature

• Radin N (2003). "Killing tumours by ceramide-induced apoptosis: a critique of available drugs". Biochem J. 371 (Pt 2): 243–56. doi:10.1042/BJ20021878. PMC 1223313. PMID 12558497. article
• Carter, Herbert E.; Glick, Francis J.; Norris, William P.; Phillips, George E. (1947). "Biochemistry of the sphingolipides. III. Structure of sphingosine". J. Biol. Chem. 170 (1): 285–295. doi:10.1016/S0021-9258(17)34955-4.

External links

• Sphingosine at the U.S. National Library of Medicine Medical Subject Headings (MeSH)