Sphingosine

Sphingosine
Skeletal formula of sphingosine
Space-filling model of the sphingosine molecule
Names
Preferred IUPAC name
(2S,3R,4E)-2-Aminooctadec-4-ene-1,3-diol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.230 Edit this at Wikidata
UNII
  • 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 checkY
    Key: WWUZIQQURGPMPG-KRWOKUGFSA-N checkY
  • 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
  • CCCCCCCCCCCCC/C=C/[C@H]([C@H](CO)N)O
Properties
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).
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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.

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.

Sphingosine has been investigated for its potential anticancer effects, as it can promote apoptosis and influence signaling pathways involved in cell growth and survival. Sphingosine has also served as a structural template for synthetic analogs, such as fingolimod (FTY720), which modulates sphingosine-1-phosphate receptor signaling through its phosphorylated metabolite.

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 sphinganine (dihydrosphingosine).

Sphingosine synthesis

Dehydrosphingosine is then reduced by NADPH to sphinganine, acylated to dihydroceramide, and finally oxidized by FAD to ceramide. Sphingosine is then solely formed via degradation of sphingolipid in the lysosome.

See also

Literature

References

  1. ↑ Jayashankar, Vaishali; Kubiniok, Peter; McCracken, Alison N; Gentry, Rebeca G; Eckenstein, Kazumi H; Sernissi, Lorenzo; Vece, Vito; Garsi, Jean-Baptiste; Valles, Sarah Y; Jung, Sunhee; Hoffman, Natalie C; Perrochon, Arielle S; Selwan, Elizabeth M; Finicle, Brendan T; Pitman, Mary (2025-06-30). "Sphingosine simultaneously inhibits nuclear import and activates PP2A by binding importins and PPP2R1A". The EMBO Journal. 44 (16): 4473–4498. doi:10.1038/s44318-025-00490-5. ISSN 1460-2075. PMC 12361511. PMID 40588551.