D-ERYTHRO-SPHINGOSINE-1-PHOSPHATE Chemical Properties

Melting point:

179-189°C

Boiling point:

548.8±60.0 °C(Predicted)

Density 

1.094±0.06 g/cm3(Predicted)

RTECS 

RG2260500

storage temp. 

-20°C

solubility 

methanol: THF: water (6:3:1): >0.5 mg/mL

form 

waxy solid

pka

1.76±0.10(Predicted)

color 

yellow

Sensitive 

Light Sensitive

Stability:

Moisture, Temperature Sensitive; Hygroscopic

InChI

InChI=1S/C18H38NO5P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(20)17(19)16-24-25(21,22)23/h14-15,17-18,20H,2-13,16,19H2,1H3,(H2,21,22,23)/b15-14+/t17-,18+/m0/s1

InChIKey

DUYSYHSSBDVJSM-KRWOKUGFSA-N

SMILES

C(OP(O)(O)=O)[C@H](N)[C@H](O)/C=C/CCCCCCCCCCCCC

CAS DataBase Reference

26993-30-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

29225090

DEA Controlled Substances

CSCN: 1635
CAS SCH: IV
NARC: N

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

D-ERYTHRO-SPHINGOSINE-1-PHOSPHATE Usage And Synthesis

Description

Sphingosine-1-phosphate (S1P) is the product of phosphorylation of sphingosine by sphingosine kinase that is secreted from cells and acts as an agonist at S1P receptors. It increases intracellular calcium levels in TAg-Jurkat cells expressing S1P₁ and G_qi5, which allows for phospholipase C stimulation by G_i 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). Intra- and extracellular levels of S1P vary spatially allowing it to function as an autocrine or paracrine factor, respectively, and dysregulation of S1P levels are associated with various disease states, such as inflammation and autoimmunity. S1P has a wide variety of effects, including an involvement in cell growth, angiogenesis, immunity, and neuroprotection.

Chemical Properties

Off-White to Grey Powder

Uses

A ligand for EDG-1 and EDG-3 and activator of GPR3, GPR6, and GPR12.

Uses

A putative lipid second messenger; found to inhibit cellular mobility of melanoma cells at very low concentrations with no toxic effects thereby making it a possible agent for prevention of tumor cell metastasis and inflammatory processes. It mobilizes intracellular calcium stores, decreases cellular cAMP, activates phospholipase D and does not inhibitprotein kinase C.

Uses

D-erythro-Dihydrosphingosine-1-phosphate is a saturated analog of D-erythro-Sphingosine-1-phosphate a putative lipid second messenger; found to inhibit cellular mobility of melanoma cells at very low concentrations with no toxic effects thereby making it a possible agent for prevention of tumor cell metastasis and inflammatory processes.

Definition

ChEBI: A phosphosphingolipid that consists of sphingosine having a phospho group attached at position 1

General Description

Sphingosine-1-phosphate (S1P), a sphingolipid, is an important cellular metabolite and signaling lipid in animal cells. It has also been found in yeasts and plants. Sphingosine kinases (SPKs) catalyzes the synthesis of S1P from spingosine and regulates S1P levels. It is the end product of ceramide catabolism and is metabolized to phosphoethanolamine and hexadecenal by S1P lyase. S1P is produced in endothelial cells.

Biological Activity

Endogenous second messenger involved in the control of cell proliferation and motility, and Ca 2+ mobilization. Acts as an agonist at sphingosine-1-phosphate receptors, S1P 1-5 . Effectors regulated include p38 MAP kinase, PLC, adenylyl cyclase, myosin light chain phosphatase and focal adhesion kinase.

Biochem/physiol Actions

A lipid second messenger that binds to S1P1 and S1P3 receptors. Mobilizes intracellular Ca2+ stores and decreases cellular cAMP. Activates phospholipase D. S1P stimulates the migration of endothelial cells but inhibits the migration of other cell types. Induces angiogenesis.

storage

Store at +4°C

References

[1] SARAH SPIEGEL  Sheldon M. Sphingosine-1-phosphate: an enigmatic signalling lipid[J]. Nature Reviews Molecular Cell Biology, 2003, 4 5: 397-407. DOI:10.1038/nrm1103
[2] HUGH ROSEN. Sphingosine 1-phosphate receptor signaling.[J]. Annual review of biochemistry, 2009, 78: 743-768. DOI:10.1146/annurev.biochem.78.072407.103733
[3] MICHAEL MACEYKA. Sphingosine-1-phosphate signaling and its role in disease.[J]. Trends in Cell Biology, 2012, 22 1: 50-60. DOI:10.1016/j.tcb.2011.09.003

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