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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

Molecular Formula C18H37NO2
Molecular Weight 299.4919
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 1
Optical Activity UNSPECIFIED

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
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 Aug
D-erythro-sphingosine lowers 3-hydroxy-3-methylglutaryl coenzyme A reductase activity in Chinese hamster ovary cells.
1993 Jan 15
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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 01:34:35 GMT 2023
Edited
by admin
on Sat Dec 16 01:34:35 GMT 2023
Record UNII
AQ8E26TZ1N
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
THREO-SPHINGOSINE, (-)-
Common Name English
4-OCTADECENE-1,3-DIOL, 2-AMINO-, (2S,3S,4E)-
Systematic Name English
L-THREO-SPHINGOSINE
Common Name English
3-L-4-SPHINGENINE
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 Sat Dec 16 01:34:35 GMT 2023 , Edited by admin on Sat Dec 16 01:34:35 GMT 2023
PRIMARY
PUBCHEM
11130338
Created by admin on Sat Dec 16 01:34:35 GMT 2023 , Edited by admin on Sat Dec 16 01:34:35 GMT 2023
PRIMARY
FDA UNII
AQ8E26TZ1N
Created by admin on Sat Dec 16 01:34:35 GMT 2023 , Edited by admin on Sat Dec 16 01:34:35 GMT 2023
PRIMARY