S4257
鞘氨醇磷酸胆碱
≥98%, intracellular and extracellular signaling mediator, powder
别名:
(2S,3R,4E)-2-氨基-4-十八碳烯-3-羟基-1-磷酸胆碱, 2-[[[(2-氨基-3-羟基-4-十八碳烯基)氧基]羟基-亚膦酰基]氧基] -N,N,N-三甲基乙胺 内盐, D-赤式-鞘氨醇磷酸胆碱, Lyso SM (d18:1), 溶鞘磷脂
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关于此项目
经验公式（希尔记法）:
C23H49N2O5P
化学文摘社编号:
分子量:
464.62
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352211
MDL number:
Beilstein/REAXYS Number:
7342520
产品名称
鞘氨醇磷酸胆碱, ≥98%, powder
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
SMILES string
[H][C@](/C=C/CCCCCCCCCCCCC)(O)[C@@]([H])(N)COP([O-])(OCC[N+](C)(C)C)=O
InChI key
JLVSPVFPBBFMBE-HXSWCURESA-N
assay
≥98%
form
powder
color
light yellow
solubility
chloroform/methanol (2:1): complete 10 mg/ml, clear to slightly hazy, colorless to light yellow
storage temp.
−20°C
Quality Level
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相关类别
Application
目前已研究了鞘氨醇磷酸胆碱对小鼠小脑颗粒神经元和PC-12细胞的神经营养作用。
Biochem/physiol Actions
鞘氨醇磷酸胆碱(SPC)是一种介导细胞内和细胞外信号传导的生物活性脂质。它通过不依赖IP3的途径从细胞内储存物中调动Ca2+。它刺激CCL2生成，可能有助于动脉粥样硬化病情发展。SPC是内皮细胞分化基因受体3 (EDG3)的配体。
存储类别
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Naoko Konno et al.
Biochemical and biophysical research communications, 364(1), 163-168 (2007-10-16)
Sphingosylphosphorylcholine (SPC) is a choline-containing naturally occurring derivative of sphingolipid involved in various biological processes. Here we show that SPC displays neurotrophic effects in cerebellar granule neurons (CGNs) and in PC12 cells. When CGNs were cultured under non-depolarizing condition, they
H Okamoto et al.
Biochemical and biophysical research communications, 260(1), 203-208 (1999-06-25)
AGR16/H218/EDG5 and EDG1 are functional receptors for lysosphingolipids, whereas EDG2 and EGD4 are receptors for lysophosphatidic acid (LPA). The present study demonstrates that EDG3, the yet poorly defined member of the EDG family G protein-coupled receptors, shows identical agonist specificity
A Uehara et al.
FEBS letters, 460(3), 467-471 (1999-11-11)
The effects of the lysosphingolipid, sphingosylphosphorylcholine (SPC), on the cardiac ryanodine receptor (RyR) were examined. The open probability of cardiac RyR incorporated in lipid bilayers was decreased by cytoplasmic, but not lumenal side application of micromolar concentrations of SPC. Modification
D Meyer zu Heringdorf et al.
FEBS letters, 410(1), 34-38 (1997-06-23)
Sphingolipid breakdown products are now being recognized to play a dual role in cellular signalling, acting as intracellular as well as extracellular signalling molecules. Both types of action may even be found with one sphingolipid species. The recent demonstration of
Ha Young Lee et al.
Journal of immunology (Baltimore, Md. : 1950), 186(7), 4347-4353 (2011-03-04)
Sphingosylphosphorylcholine (SPC) is a component of high-density lipoprotein particles. We investigated the functional role of SPC in HUVECs. SPC stimulation induced production of the CCL2 chemokine in a PTX-sensitive G-protein-dependent manner. SPC treatment caused the activation of NF-κB and AP-1
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