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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
Structure of THREO-SPHINGOSINE, (-)-

SMILES

CCCCCCCCCCCCC\C=C\[C@H](O)[C@@H](N)CO

InChI

InChIKey=WWUZIQQURGPMPG-DNWQSSKHSA-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-/m0/s1

HIDE SMILES / InChI
Threo-sphingosine, (-)- is a stereoisomer of naturally occurring D-erythro-sphingosine. It is a Protein kinase C inhibitor. Threo-sphingosine, (-)- is partly active in induction of apoptosis and inhibition of MAPK activity in different kinds of solid tumor cell lines. It can be phosphorylated by cells, but the resulting L-Threo-sphingosine 1-phosphate does not bind and activate sphingosine 1-phosphate receptors, excluding their role in Threo-sphingosine, (-)-induced growth inhibition. Cell culture experiments with Diffuse large B cell lymphoma cell lines that were incubated with Threo-sphingosine, (-)- manifested significant inhibition of cell growth, while incubation of cells with similar concentrations of sphingosine 1-phosphate was ineffective. These results suggest that Threo-sphingosine, (-)- accumulation could be an alternative treatment option for Diffuse large B cell lymphoma.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Divergent synthesis of D-erythro-sphingosine, L-threo-sphingosine, and their regioisomers.
2003-03-21
Selectivity of sphingosine-induced apoptosis. Lack of activity of DL-erythyro-dihydrosphingosine.
1998-05-29
Chemoenzymatic Synthesis of All Four Stereoisomers of Sphingosine from Chlorobenzene: Glycosphingolipid Precursors(1)(a).
1998-02-06
Role of ceramide in mitogenesis induced by exogenous sphingoid bases.
1994-03-04
D-erythro-sphingosine lowers 3-hydroxy-3-methylglutaryl coenzyme A reductase activity in Chinese hamster ovary cells.
1993-01-15
A series of fluorescent N-acylsphingosines: synthesis, physical properties, and studies in cultured cells.
1988-06-14
Chemical properties and stereoisomerism of heterogeneous long chain bases in lysosphingolipids by positive ion fast atom bombardment mass spectrometry and carbon-13 NMR spectroscopy.
1986-08
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Threo-sphingosine, (-)- at 1 uM, 5 uM, 10 uM, and 15 uM concentrations had no effect on the levels of HMG-CoA reductase activity in CHO-K1 cells.
Name Type Language
3-L-4-SPHINGENINE
Preferred Name English
THREO-SPHINGOSINE, (-)-
Common Name English
4-OCTADECENE-1,3-DIOL, 2-AMINO-, (2S,3S,4E)-
Systematic Name English
L-THREO-SPHINGOSINE
Common Name English
4-OCTADECENE-1,3-DIOL, 2-AMINO-, (E)-L-THREO-
Common Name English
L-THREO-C18-SPHINGOSINE
Common Name English
4-OCTADECENE-1,3-DIOL, 2-AMINO-, (S-(R*,R*-(E)))-
Common Name English
(2S,3S)-SPHINGOSINE
Systematic Name English
Code System Code Type Description
CAS
25695-95-8
Created by admin on Mon Mar 31 20:54:07 GMT 2025 , Edited by admin on Mon Mar 31 20:54:07 GMT 2025
PRIMARY
PUBCHEM
11130338
Created by admin on Mon Mar 31 20:54:07 GMT 2025 , Edited by admin on Mon Mar 31 20:54:07 GMT 2025
PRIMARY
FDA UNII
AQ8E26TZ1N
Created by admin on Mon Mar 31 20:54:07 GMT 2025 , Edited by admin on Mon Mar 31 20:54:07 GMT 2025
PRIMARY