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 Edit this at Wikidata
EC Number	212-116-0
IUPHAR/BPS	2453
KEGG	C00836
PubChem CID	91486
UNII	YT0ZSD64HM
CompTox Dashboard (EPA)	DTXSID501016568 Edit this at Wikidata
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

Chemical compound

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

[edit ]

^ "Sphinganine". Lipid Maps Structure Database.
^ Merrill, Alfred H. (2025年01月14日). "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年05月03日). "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.

Sphinganine

See also

References

Further reading