Sphingosine-1-phosphate

Modify Date: 2024-01-08 13:15:24

Sphingosine-1-phosphate Structure
Sphingosine-1-phosphate structure
Common Name Sphingosine-1-phosphate
CAS Number 26993-30-6 Molecular Weight 379.472
Density 1.1±0.1 g/cm3 Boiling Point 548.8±60.0 °C at 760 mmHg
Molecular Formula C18H38NO5P Melting Point 190ºC
MSDS Chinese USA Flash Point 285.7±32.9 °C

 Use of Sphingosine-1-phosphate


Sphingosine-1-phosphate (S1P) is an agonist of S1P1-5 receptors and a ligand of GPR3, GPR6 and GPR12. Sphingosine-1-phosphate is an intracellular second messenger and mobilizes Ca2+ as an extracellular ligand for G protein-coupled receptors[1]. Sphingosine-1-phosphate is an important lipid mediator generated from Sphingomyelin (HY-113498) or other membrane phospholipids[2].

 Names

Name sphingosine 1-phosphate
Synonym More Synonyms

 Sphingosine-1-phosphate Biological Activity

Description Sphingosine-1-phosphate (S1P) is an agonist of S1P1-5 receptors and a ligand of GPR3, GPR6 and GPR12. Sphingosine-1-phosphate is an intracellular second messenger and mobilizes Ca2+ as an extracellular ligand for G protein-coupled receptors[1]. Sphingosine-1-phosphate is an important lipid mediator generated from Sphingomyelin (HY-113498) or other membrane phospholipids[2].
Related Catalog
Target

Human Endogenous Metabolite

In Vitro S1P (1 μM) induces a significant Ca2+ releases in HEK293 cells under serum starvation conditions (1% FCS)[1]. In a functional Ca2+ assay, Suramin (HY-B0879) alone does not exert any effect on intracellular Ca2+ release via gpr3, gpr6 or gpr12. In contrast, S1P (1 μM) induces Ca2+ release of gpr3, gpr6 and gpr12 in the presence of Suramin (HY-B0879) various concentrations in transfected HEK293 cells[2]. In a functional Ca2+ assay,S1P (3-3000 nM) in the presence Suramin (300 μM), exhibits nanomolar EC50 values for gpr3 (EC50=29 nM), gpr6 (EC50=15 nM) and gpr12 (EC50=24 nM), rat gpr3 (EC50=68 nM),respectively in HEK293 cells[2]. S1P increases intracellular calcium levels in TAg-Jurkat cells expressing S1P1 and Gqi5, which allows for phospholipase C stimulation by Gi proteins, when used at a concentration of 200 nM, as well as in TAg-Jurkat cells expressing S1P2 and S1P3 receptors (EC50s = 8 and 11 nM, respectively)[3].
References

[1]. Teresa Sanchez, et al. Structural and Functional Characteristics of S1P Receptors. J Cell Biochem. 2004 Aug 1;92(5):913-22.

[2]. Kirsten Uhlenbrock, et al. Sphingosine 1-phosphate Is a Ligand of the Human gpr3, gpr6 and gpr12 Family of Constitutively Active G Protein-Coupled Receptors. Cell Signal. 2002 Nov;14(11):941-53.

[3]. S An, et al. Transduction of Intracellular Calcium Signals Through G Protein-Mediated Activation of Phospholipase C by Recombinant Sphingosine 1-phosphate Receptors. Mol Pharmacol. 1999 May;55(5):787-94

 Chemical & Physical Properties

Density 1.1±0.1 g/cm3
Boiling Point 548.8±60.0 °C at 760 mmHg
Melting Point 190ºC
Molecular Formula C18H38NO5P
Molecular Weight 379.472
Flash Point 285.7±32.9 °C
Exact Mass 379.248749
PSA 122.82000
LogP 5.46
Vapour Pressure 0.0±3.3 mmHg at 25°C
Index of Refraction 1.501
Storage condition −20°C
Stability Moisture, Temperature Sensitive; Hygroscopic
Water Solubility methanol: THF: water (6:3:1): >0.5 mg/mL

 Safety Information

Personal Protective Equipment dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes Xi
Risk Phrases 36/37/38
Safety Phrases S26-S36
RIDADR NONH for all modes of transport
WGK Germany 3
HS Code 2922509090

 Synthetic Route

 Customs

HS Code 2922509090
Summary 2922509090. other amino-alcohol-phenols, amino-acid-phenols and other amino-compounds with oxygen function. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

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 Synonyms

(4E)-2-Amino-3-hydroxy-4-octadecen-1-yldihydrogen-phosphat
(2S,3R,4E)-2-Amino-4-octadecene-1,3-diol 1-phosphate D-erythro-Sphingosine 1-phosphate
[(E,2S,3R)-2-amino-3-hydroxyoctadec-4-enyl] dihydrogen phosphate
Sphing-4-enine 1-phosphate
4-Octadecene-1,3-diol, 2-amino-, 1-(dihydrogen phosphate), (4E)-
C18-Sphingosine 1-phosphate
D-erythro-sphingosine-1-phosphate
Sphingosine 1-phosphate
Dihydrogène phosphate de (4E)-2-amino-3-hydroxy-4-octadécèn-1-yle
MFCD00274457
S1P
Sphingosine 1-phosphic acid
(2S,3R,4E)-2-Amino-4-octadecene-1,3-diol 1-phosphate,D-erythro-Sphingosine 1-phosphate
D-erythro-Sphingosine 1-phosphate
Somatostatin 1-28
(4E)-2-amino-3-hydroxyoctadec-4-en-1-yl dihydrogen phosphate
(4E)-2-Amino-3-hydroxy-4-octadecen-1-yl dihydrogen phosphate
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