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About This Item
Empirical Formula (Hill Notation):
C19H39NO2
CAS Number:
Molecular Weight:
313.52
MDL number:
UNSPSC Code:
12352211
NACRES:
NA.25
assay
>99% (TLC)
form
powder
packaging
pkg of 1 × 5 mg (860478P-5mg)
manufacturer/tradename
Avanti Research™ - A Croda Brand
lipid type
sphingolipids
shipped in
dry ice
storage temp.
−20°C
SMILES string
CCCCCCCCCCCCC/C=C(C)\[C@@H](O)[C@@H](N)CO
InChI
1S/C19H39NO2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-17(2)19(22)18(20)16-21/h15,18-19,21-22H,3-14,16,20H2,1-2H3/b17-15-/t18-,19+/m0/s1
InChI key
LMJPKTKGCMCPGM-PIIWLPLESA-N
General description
cis-4-methylsphingosine (cis-4M-Sph) is a methyl-branched sphingosine analog.
Biochem/physiol Actions
cis-4-methylsphingosine (cis-4M-Sph) modulates sphingosine 1 phosphate (S1P) receptor through its metabolite cis-4-methylsphingosine-1-phosphate (cis-4M-S1P). This leads to S1P receptor internalization and desensitization. cis-4M-Sph shows an inhibitory effect on serine palmitoyltransferase activity.
Packaging
5 mL Amber Glass Screw Cap Vial (860478P-5mg)
Legal Information
Avanti Research is a trademark of Avanti Polar Lipids, LLC
Storage Class
11 - Combustible Solids
wgk
WGK 3
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G van Echten-Deckert et al.
The Journal of biological chemistry, 272(25), 15825-15833 (1997-06-20)
The effect of six different structurally modified sphingosine analogues on biosynthesis of sphingolipids was studied in primary cultured murine cerebellar neurons. Treatment of cells with cis-4-methylsphingosine at micromolar levels resulted in a markedly decreased sphingolipid biosynthesis, whereas the other compounds
Michael Ter Braak et al.
Biochemical pharmacology, 81(5), 617-625 (2010-12-18)
Sphingosine-1-phosphate (S1P) acts as high affinity agonist at specific G-protein-coupled receptors, S1P(1-5), that play important roles e.g. in the cardiovascular and immune systems. A S1P receptor modulating drug, FTY720 (fingolimod), has been effective in phase III clinical trials for multiple
Qun Li et al.
International journal of molecular medicine, 42(2), 1054-1063 (2018-05-12)
Stroke is the second most common cause of death worldwide, and thus, it imposes great financial burdens on both individuals and society. Mesenchymal stem cell (MSC) therapy is a promising approach for ischemic brain injury. However, MSC treatment potential is