Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C18H37NO2 |
| Molecular Weight | 299.4919 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCCCCCCCCCC\C=C\[C@H](O)[C@H](N)CO
InChI
InChIKey=WWUZIQQURGPMPG-MCXRAWCPSA-N
InChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3/b15-14+/t17-,18+/m1/s1
L-erythro-Sphingosine (also known as erythro-Sphingosine, (+)) – is an inactive isomer from the four possible stereoisomers of sphingosine. This isomer can induce dephosphorylation of pRb protein with EC50 = 5 μM. -erythro-Sphingosine is a weak substrate of ceramidase and has shown competitive inhibition properties.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Sphingosine and FTY720 are potent inhibitors of the transient receptor potential melastatin 7 (TRPM7) channels. | 2013-03 |
|
| Pharmacologic manipulation of sphingosine kinase in retinal endothelial cells: implications for angiogenic ocular diseases. | 2006-11 |
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| Activation of the melastatin-related cation channel TRPM3 by D-erythro-sphingosine [corrected]. | 2005-03 |
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| ACTH regulates steroidogenic gene expression and cortisol biosynthesis in the human adrenal cortex via sphingolipid metabolism. | 2004-11 |
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| Modulation by sphingosine of phosphorylation of substrate proteins by protein kinase C in nuclei from cow mammary gland. | 2004-10 |
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| Role of human sphingosine-1-phosphate phosphatase 1 in the regulation of intra- and extracellular sphingosine-1-phosphate levels and cell viability. | 2003-09-05 |
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| Sphingosine in apoptosis signaling. | 2002-12-30 |
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| Ursodeoxycholic acid enhances glucocorticoid-induced tyrosine aminotransferase-gene expression in cultured rat hepatocytes. | 1997-11-26 |
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| A novel mechanism of action of corticotropin releasing factor in rat Leydig cells. | 1990-02-05 |
|
| A further comparison of insulin- and phorbol ester-stimulated glucose transport in adipocytes. | 1989-08 |
Sample Use Guides
The role of the natural D-erythro-sphingosine in regulation of cell growth and pRb dephosphorylation was evaluated using chemically synthesized pure isomers of sphingosine. Of the four possible stereoisomers of sphingosine, D-erythro-sphingosine was most active in inducing dephosphorylation of pRb protein with an EC50% of 0.6 microM whereas its enantiomer L-erythro-sphingosine (erythro-sphingosine, (+)-) was 8-fold less potent with an EC50% of 5 microM. The dose responses for inhibition of cell growth were nearly identical to the EC50% for pRb dephosphorylation with D-erythro-sphingosine causing 50% inhibition at 0.6 microM whereas L-erythro-sphingosine was 5-6-fold less potent.
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5496506
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SUBSTANCE RECORD
