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Structure Database (LMSD)

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Common Name

Sphinganine-phosphate

Systematic Name

Sphinganine-1-phosphate

Synonyms

Dihydrosphingosine phosphate

LM ID

LMSP01050002

Formula

C₁₈H₄₀NO₅P

Exact Mass

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381.264412

Sum Composition

SPBP 18:0;O2

Status

Curated

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Classification

Biological Context

Sphinganine-1-phosphate is an intermediate in the metabolism of glycosphingolipids and sphingolipids. It acts as an antagonist at the sphingosine-1-phosphate (S1P1/EDG-1) receptor (Ki = 15 nM).¹ Sphinganine-1-phosphate prevents liver and kidney damage following hepatic ischemia and reperfusion injury in mice at doses lower than 0.1 and 0.2 mg/kg when administered prior to or following reperfusion, respectively.² It has antifibrotic effects in scleroderma fibroblasts through normalization of PTEN protein levels, collagen and matrix metalloproteinase-1 (MMP-1) expression, and Smad3 phosphorylation.^3,4

This information has been provided by Cayman Chemical

References

1. Bu, S., Kapanadze, B., Hsu, T., et al. Opposite effects of dihydrosphingosine 1-phosphate and sphingosine 1-phosphate on transforming growth factor-β/Smad signaling are mediated through the PTEN/PPM1A-dependent pathway. The Journal of Biological Chemisty 283(28), 19593-19602 (2008).

2. Van Brocklyn, J.R., Lee, M.-J., Menzeleev, R., et al. Dual actions of sphingosine-1-phosphate: extracellular through the Gi-coupled receptor Edg-1 and intracellular to regulate proliferation and survival. J. Cell. Biol. 142(1), 229-240 (1998).

3. Bu, S., Asano, Y., Bujor, A., et al. Dihydrosphingosine 1-phosphate has a potent antifibrotic effect in scleroderma fibroblasts via normalization of phosphatase and tensin homolog levels. Arthrtis Rheum. 62(7), 2117-2126 (2010).

4. Park, S.W., Kim, M., Chen, S.W.C., et al. Sphinganine-1-phosphate attenuates both hepatic and renal injury induced by hepatic ischemia and reperfusion in mice. Shock 33(1), 31-42 (2010).