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S9666

Sigma-Aldrich

Sphingosine 1-phosphate

≥95% (TLC), powder, lipid second messenger

Synonym(s):

(2S,3R,4E)-2-Amino-4-octadecene-1,3-diol 1-phosphate, D-erythro-Sphingosine 1-phosphate

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About This Item

Empirical Formula (Hill Notation):
C18H38NO5P
CAS Number:
26993-30-6
Molecular Weight:
379.47
MDL number:
MFCD00270077
UNSPSC Code:
12352211
PubChem Substance ID:
24899853
NACRES:
NA.77

product name

Sphingosine 1-phosphate, ≥95%, powder

Quality Level

300

Assay

≥95%

form

powder

storage temp.

−20°C

SMILES string

CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)COP(O)(O)=O

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

InChI key

DUYSYHSSBDVJSM-KRWOKUGFSA-N

Gene Information

human ... S1PR1(1901) , S1PR2(9294) , S1PR3(1903) , S1PR4(8698) , S1PR5(53637)

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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.

Features and Benefits

This compound is featured on the Lysophospholipid Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Kaiqi Sun et al.
Nature communications, 7, 12086-12086 (2016-07-16)
Sphingosine-1-phosphate (S1P) is a bioactive signalling lipid highly enriched in mature erythrocytes, with unknown functions pertaining to erythrocyte physiology. Here by employing nonbiased high-throughput metabolomic profiling, we show that erythrocyte S1P levels rapidly increase in 21 healthy lowland volunteers at
Tsuyoshi Nishi et al.
Biochimica et biophysica acta, 1841(5), 759-765 (2013-08-08)
Sphingosine 1-phosphate (S1P) is a lipid mediator that plays important roles in diverse cellular functions such as cell proliferation, differentiation and migration. S1P is synthesized inside the cells and subsequently released to the extracellular space, where it binds to specific
Emmanuel E Egom et al.
Current opinion in lipidology, 24(4), 351-356 (2013-05-09)
The absolute level of HDL cholesterol (HDL-C) may not be the only criterion contributing to their antiatherothrombotic effects. This review focuses on evidence in support of the concept that HDL-bound sphingosine-1-phosphate (S1P) plays a role in different HDL atheroprotective properties
Gregory T Kunkel et al.
Nature reviews. Drug discovery, 12(9), 688-702 (2013-08-21)
The bioactive lipid sphingosine-1-phosphate (S1P) is involved in multiple cellular signalling systems and has a pivotal role in the control of immune cell trafficking. As such, S1P has been implicated in disorders such as cancer and inflammatory diseases. This Review
H Okamoto et al.
Molecular and cellular biology, 20(24), 9247-9261 (2000-11-30)
Sphingosine-1-phosphate (S1P) is a bioactive lysophospholipid that induces a variety of biological responses in diverse cell types. Many, if not all, of these responses are mediated by members of the EDG (endothelial differentiation gene) family G protein-coupled receptors EDG1, EDG3
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