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About This Item
Empirical Formula (Hill Notation):
C23H49N2O5P
CAS Number:
Molecular Weight:
464.62
MDL number:
UNSPSC Code:
12352211
NACRES:
NA.25
assay
>99% (TLC)
form
powder
packaging
pkg of 1 × 10 mg (860600P-10mg), pkg of 1 × 25 mg (860600P-25mg), pkg of 1 × 5 mg (860600P-5mg), pkg of 1 × 50 mg (860600P-50mg)
manufacturer/tradename
Avanti Research™ - A Croda Brand
lipid type
sphingolipids
shipped in
dry ice
storage temp.
−20°C
SMILES string
[H][C@](/C=C/CCCCCCCCCCCCC)(O)[C@@]([H])(N)COP([O-])(OCC[N+](C)(C)C)=O
InChI
1S/C23H49N2O5P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(26)22(24)21-30-31(27,28)29-20-19-25(2,3)4/h17-18,22-23,26H,5-16,19-21,24H2,1-4H3/b18-17+/t22-,23+/m0/s1
InChI key
JLVSPVFPBBFMBE-HXSWCURESA-N
General description
Lyso SM (d18:1), also known as sphingosylphosphorylcholine (SPC), is a bioactive lipid molecule. This lysophospholipid is present in normal blood plasma, ascites and various tissues.
Application
Lyso SM (d18:1) has been used:
- to study its effect on the skeletal muscle ryanodine receptor (RyR1), in the presence and absence of calmodulin through single channel recordings in planar lipid bilayers
- as an inhibitor of Ca2+ sensor calmodulin (CaM)
- as a standard in circular dichroism (CD) spectroscopy to determine lipid selectivity of the lipid-peptide interactions
Biochem/physiol Actions
Lyso SM (d18:1) or sphingosylphosphorylcholine (SPC) is a lipid mediator that exhibits second messenger functions. It regulates ryanodine receptors (RyRs) and releases Ca2+ from the sarco/endoplasmic reticulum. Lyso SM (d18:1) acts as an endogenous inhibitor of ubiquitous Ca2+ sensor calmodulin (CaM).
Packaging
5 mL Amber Glass Screw Cap Vial (860600P-50mg)
5 mL Amber Glass Screw Cap Vial (860600P-5mg)
5 mL Amber Glass Screw Cap Vial (860600P-10mg)
5 mL Amber Glass Screw Cap Vial (860600P-25mg)
Legal Information
Avanti Research is a trademark of Avanti Polar Lipids, LLC
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Dagmar Meyer zu Heringdorf et al.
Biochimica et biophysica acta, 1582(1-3), 178-189 (2002-06-19)
Compared to the lysophospholipid mediators, sphingosine-1-phosphate (S1P) and lysophosphatidic acid (LPA), little information is available regarding the molecular mechanisms of action, metabolism and physiological significance of the related sphingosylphosphorylcholine (SPC). S1P and LPA have recently been established as agonists at
Erika Kovacs et al.
Biochemical and biophysical research communications, 401(2), 281-286 (2010-09-21)
Sphingosylphosphorylcholine (SPC), a lipid mediator with putative second messenger functions, has been reported to regulate ryanodine receptors (RyRs), Ca2+ channels of the sarco/endoplasmic reticulum. RyRs are also regulated by the ubiquitous Ca2+ sensor calmodulin (CaM), and we have previously shown
Sphingosylphosphorylcholine and lysophosphatidylcholine are ligands for the G protein-coupled receptor GPR4.
The Journal of biological chemistry, 280(52), 43280-43280 (2006-02-25)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 860600P-10MG | 04061835318506 |
| 860600P-50MG | 04061835318520 |
| 860600P-5MG | 04061835318537 |