| 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
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
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.
SUBSTANCE RECORD
