Sphingosine

Sphingosine

Names
IUPAC name (2S,3R)-2-aminooctadec-4-ene-1,3-diol
Identifiers
CAS Number	123-78-4 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:16393 N
ChemSpider	4444047 Y
ECHA InfoCard	100.004.230
IUPHAR/BPS	2452
PubChem CID	5280335
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	299.50 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Sphingosine (2-amino-4-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 dehydrosphingosine.

Dehydrosphingosine is then reduced by NADPH to dihydrosphingosine (sphinganine), and finally oxidized by FAD to sphingosine.