Sphinganine

Sphinganine is a chemical compound of the sphingolipid class with molecular formula C₁₈H₃₉NO₂. Via the action of sphingosine kinase enzymes, it is converted to dihydrosphingosine 1-phosphate (sphinganine 1-phosphate), which has a variety of biological functions.^[1]

Sphinganine

Names
IUPAC name Sphinganine
Preferred IUPAC name Sphinganine
Systematic IUPAC name (2S,3R)-2-Aminooctadecane-1,3-diol
Other names Dihydrospingosine DL-erythro-Dihydrosphingosine 2-Amino-1,3-dihydroxyoctadecane [R-(R*,S*)]-2-aminooctadecane-1,3-diol
Identifiers
CAS Number	764-22-7
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16566
ChEMBL	ChEMBL448741
ChemSpider	82609
DrugBank	DB11924
ECHA InfoCard	100.011.014
EC Number	212-116-0
IUPHAR/BPS	2453
KEGG	C00836
PubChem CID	91486
UNII	YT0ZSD64HM
CompTox Dashboard (EPA)	DTXSID501016568
InChI InChI=1S/C18H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h17-18,20-21H,2-16,19H2,1H3/t17-,18+/m0/s1 Key: OTKJDMGTUTTYMP-ZWKOTPCHSA-N
SMILES C(CCCCCCCCCCCCCC)[C@H]([C@H](CO)N)O
Properties
Chemical formula	C18H39NO2
Molar mass	301.515 g·mol−1
Related compounds
Related sphingolipids	Sulfatide Ceramide Sphingosine Phytosphingosine Sphingosine-1-phosphate
Related compounds	Safingol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Sphinganine is one of many sphingoid bases (long-chain bases) besides sphingosine, which are backbones of sphingolipids.^[2] It is made by dehydrogenating 3-ketosphinganine, which is produced by condensation reaction of serine with palmitate. It is an intermediate in the biosynthesis of ceramide.^[3]

Sphinganine is a diastereomer of safingol.

See also

• Sphingomonadaceae
• Serine C-palmitoyltransferase