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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-NVGHFZOBSA-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

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

Description

Threo-sphingosine, (+)-, also known as D-threo-sphingosine, is the less active form from all isomers of sphingosine, can inhibit protein kinase C in vitro.

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
An efficient synthesis of D-erythro- and D-threo-sphingosine from D-glucose: olefin cross-metathesis approach.
2005 Dec 22
Patents

Patents

CA2174431C
2

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Treatment of HL-60 ells with D-erythro-C2-ceramide (1-5 uM) for 2 days resulted in a dose-dependent inhibition of cell growth. Its enantiomer, L-erythro-C2-ceramide, was equally potent. The diastereomer, L-threo-C2ceramide, was more potent than D-erythro-C2-ceramide whereas D-threo-C2-ceramide (D-threo-sphingosine) was less potent. The IC50 for these compounds ranged be-ween 2.5 and 4.5 uM.
Substance Class Chemical
Created
by admin
on Sat Dec 16 01:26:17 GMT 2023
Edited
by admin
on Sat Dec 16 01:26:17 GMT 2023
Record UNII
4423HD881O
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
THREO-SPHINGOSINE, (+)-
Common Name English
4-OCTADECENE-1,3-DIOL, 2-AMINO-, (E)-D-THREO-
Common Name English
D-THREO-C18-SPHINGOSINE
Common Name English
THREO-C18-SPHINGOSINE
Common Name English
4-OCTADECENE-1,3-DIOL, 2-AMINO-, (2R,3R,4E)-
Systematic Name English
4-OCTADECENE-1,3-DIOL, 2-AMINO-, (R-(R*,R*-(E)))-
Common Name English
D-THREO-SPHINGOSINE
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID90975773
Created by admin on Sat Dec 16 01:26:17 GMT 2023 , Edited by admin on Sat Dec 16 01:26:17 GMT 2023
PRIMARY
CAS
6036-85-7
Created by admin on Sat Dec 16 01:26:17 GMT 2023 , Edited by admin on Sat Dec 16 01:26:17 GMT 2023
PRIMARY
FDA UNII
4423HD881O
Created by admin on Sat Dec 16 01:26:17 GMT 2023 , Edited by admin on Sat Dec 16 01:26:17 GMT 2023
PRIMARY
PUBCHEM
447699
Created by admin on Sat Dec 16 01:26:17 GMT 2023 , Edited by admin on Sat Dec 16 01:26:17 GMT 2023
PRIMARY
NIH
NCATS
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