Sphinganine

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 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 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.

References

↑ "Sphinganine". Lipid Maps Structure Database.
↑ Merrill, Alfred H. (2025-01-14). "Don't Be Surprised When These Surprise You: Some Infrequently Studied Sphingoid Bases, Metabolites, and Factors That Should Be Kept in Mind During Sphingolipidomic Studies". International Journal of Molecular Sciences. 26 (2): 650. doi:10.3390/ijms26020650. ISSN 1422-0067. PMC 11765627. PMID 39859363.
↑ Abed Rabbo, Muna; Khodour, Yara; Kaguni, Laurie S.; Stiban, Johnny (2021-05-03). "Sphingolipid lysosomal storage diseases: from bench to bedside". Lipids in Health and Disease. 20 (1): 44. doi:10.1186/s12944-021-01466-0. ISSN 1476-511X. PMC 8094529. PMID 33941173.

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Sphinganine

See also

References

Further reading