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.

See also

• Sphingomonadaceae
• Serine C-palmitoyltransferase

References

1. "Sphinganine". Lipid Maps Structure Database.
2. 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.
3. 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.

Further reading

• Qu, Linkai; Wang, Lei; Ji, Hao; Fang, Yimeng; Lei, Pengyu; Zhang, Xingxing; Jin, Libo; Sun, Da; Dong, Hao (2022-03-01). "Toxic Mechanism and Biological Detoxification of Fumonisins". Toxins. 14 (3): 182. doi: 10.3390/toxins14030182 . ISSN   2072-6651. PMC   8954241 . PMID   35324679.