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AB141748

D-erythro Sphingosine-1-phosphate, agonist of S1P receptors

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MW 379.5 Da, Purity >98%. Endogenous signaling sphingolipid and agonist of S1P receptors (EDG-GPCRs). Mobilises Ca2+ from intracellular stores via IP3 receptor independent pathways. Activates MAPK pathways. Regulates a variety of cellular responses and promotes angiogenesis.

View Alternative Names

AGR16, CD363, CHEDG 1, D1S3362, ECGF 1, EDG 1, EDG 3, EDG 5, EDG6, EDG8 S1P receptor, Endothelial Cell Differentiation Gene 5, Endothelial Differentiation Gene 8, Endothelial differentiation lysophosphatidic acid G protein coupled receptor 6, Endothelial differentiation G-protein coupled receptor 1, Endothelial differentiation G-protein coupled receptor 3, Endothelial differentiation G-protein coupled receptor 5, Endothelial differentiation G-protein coupled receptor 6, Endothelial differentiation G-protein-coupled receptor 8, Endothelial differentiation gene 3, Endothelial differentiation gene 6, Endothelial differentiation sphingolipid G protein coupled receptor 1, Endothelial differentiation sphingolipid G protein coupled receptor 3, Endothelial differentiation sphingolipid G protein coupled receptor 5, Endothelial differentiation sphingolipid G protein coupled receptor 8, FLJ37523, FLJ58121, FLJ93220, G protein coupled receptor endothelial differentiation gene 3, G protein coupled sphingolipid receptor, Gpcr13, H218, LPB 3, LPC 1, LPb2, Lysophospholipid receptor B2, Lysophospholipid receptor C1, MGC129298, MGC71696, OTTHUMP00000215691, Putative G protein coupled receptor, S1P receptor 1, S1P receptor 2, S1P receptor 3, S1P receptor 4, S1P receptor 5, S1P receptor Edg-1, S1P receptor Edg-3, S1P receptor Edg-5, S1P receptor Edg-6, S1P receptor Edg-8, S1P(1) receptor, S1P1, S1P2, S1P3, S1P4, S1P5, S1PR1_HUMAN, S1PR2_HUMAN, S1PR3_HUMAN, S1PR4_HUMAN, S1PR5_HUMAN, SLP4, SPPR 1, SPPR 2, Sphingosine 1-phosphate receptor 1, Sphingosine 1-phosphate receptor 2, Sphingosine 1-phosphate receptor 3, Sphingosine 1-phosphate receptor 4, Sphingosine 1-phosphate receptor 5, Sphingosine 1-phosphate receptor Edg-1, Sphingosine 1-phosphate receptor Edg-3, Sphingosine 1-phosphate receptor Edg-5, Sphingosine 1-phosphate receptor Edg-6, Sphingosine 1-phosphate receptor Edg-8, Sphingosine 1phosphate receptor type 1 S1P1, g protein-coupled receptor edg-1, sphingolipid g-protein-coupled receptor 1

1 Images
Chemical Structure - D-erythro Sphingosine-1-phosphate, agonist of S1P receptors (AB141748)
  • Chemical Structure

Lab

Chemical Structure - D-erythro Sphingosine-1-phosphate, agonist of S1P receptors (AB141748)

2D chemical structure image of ab141748, D-erythro Sphingosine-1-phosphate, agonist of S1P receptors

Key facts

CAS number

26993-30-6

Purity

>98%

Form

Solid

form

Molecular weight

379.5 Da

Molecular formula

C<sub>1</sub><sub>8</sub>H<sub>3</sub><sub>8</sub>NO<sub>5</sub>P

PubChem

5283560

Nature

Synthetic

Solubility

Sparingly soluble in 1:1 ethanol:water. Addition of small amounts of acetic acid may help dissolve this product.

Soluble in warm methanol.

Biochemical name

Sphingosine 1-phosphate

Biological description

Endogenous signaling sphingolipid and agonist of S1P receptors (EDG-GPCRs). Mobilises Ca2+ from intracellular stores via IP3 receptor independent pathways. Activates MAPK pathways. Regulates a variety of cellular responses and promotes angiogenesis.

Canonical smiles

CCCCCCCCCCCCCC=CC(C(COP(=O)(O)O)N)O

Isomeric smiles

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

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

IUPAC Name

[(E,2S,3R)-2-amino-3-hydroxyoctadec-4-enyl] dihydrogen phosphate

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Properties and storage information

Shipped at conditions
Ambient - Can Ship with Ice
Appropriate short-term storage conditions
-20°C
Appropriate long-term storage conditions
-20°C
Storage information
Store under desiccating conditions|The product can be stored for up to 12 months
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Supplementary information

This supplementary information is collated from multiple sources and compiled automatically.

S1P1/EDG1 EDG3/S1P3 S1PR2 EDG6/S1PR4 and EDG8 are members of the sphingosine-1-phosphate (S1P) receptor family alternatively known as the endothelin differential growth factor receptors (EDG receptors). These receptors are G-protein coupled receptors (GPCRs) involved in the regulation of various cellular processes. Mechanically they bind sphingosine-1-phosphate (S1P) a signaling lipid to mediate intracellular signaling cascades. The expression of these receptors spans multiple tissues including the cardiovascular and immune systems. Each member has a unique molecular mass typically ranging between 40 to 60 kDa.
Biological function summary

These receptors play a critical role in modulating immune cell trafficking vascular development and maintaining endothelial integrity. They often function as part of receptor complexes collaborating with other cell surface molecules to modulate downstream signaling pathways. Their activity helps control the movement of lymphocytes across endothelial barriers and influences the vascular tone impacting blood pressure regulation and immune responses.

Pathways

The S1P receptors are key components in the sphingolipid signaling pathway and the chemokine signaling pathway. Their interaction with S1P ties them to cascade events involving Rho family GTPases and other downstream signaling proteins like Akt and ERK. These interactions regulate cytoskeletal rearrangements and cell survival demonstrating their pivotal role in signaling networks that control cellular processes such as migration proliferation and apoptosis.

Dysregulation of S1P receptors correlates with conditions like multiple sclerosis and atherosclerosis. In multiple sclerosis altered S1P signaling affects lymphocyte egress from lymphoid tissues contributing to the pathogenesis of autoimmune attacks on the central nervous system. Similarly in atherosclerosis abnormal expression of these receptors can influence vascular inflammation and plaque development. S1P receptor modulators like fingolimod target these pathways by specifically interacting with associated proteins to treat the underlying disorders.
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Product protocols

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