A selective SIP1 receptor agonist
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CYM 5442

Item No. 16925

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-[[4-[5-(3,4-diethoxyphenyl)-1,2,4-oxadiazol-3-yl]-2,3-dihydro-1H-inden-1-yl]amino]-ethanol
CAS Number
1094042-01-9
Molecular Formula
C23H27N3O4
Formula Weight
409.5
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 0.25 mg/mlDMSO: 0.25 mg/ml
λmax
233, 282, 302 nm
SMILES
CCOC1=C(OCC)C=C(C2=NC(C3=CC=CC4=C3CCC4NCCO)=NO2)C=C1
InChi Code
InChI=1S/C23H27N3O4/c1-3-28-20-11-8-15(14-21(20)29-4-2)23-25-22(26-30-23)18-7-5-6-17-16(18)9-10-19(17)24-12-13-27/h5-8,11,14,19,24,27H,3-4,9-10,12-13H2,1-2H3
InChi Key
NUIKTBLZSPQGCP-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $54

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    5 mg

    $158

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    10 mg

    $252

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    25 mg

    $560

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    Product Description

    Sphingosine-1-phosphate (S1P) is an extracellular lipid mediator whose major effects are mediated through five distinct G protein-coupled receptors, S1P1/EDG-1, S1P2/EDG-5, S1P3/EDG-3, S1P4/EDG-6, and S1P5/EDG-8. S1P1 is important for vascular development and lymphocyte maturation, migration, and trafficking.1 CYM 5442 is a full agonist for S1P1 internalization, phosphorylation, and ubiquitination (EC50 = 1.35 nM).2 It is ineffective at S1P2, S1P3, S1P4, and S1P5 at concentrations up to 10 µM.2 CYM 5442 has been found to activate S1P1-mediated p42/p44 MAPK phosphorylation in CHO-K1 cells transfected with S1P1 with an EC50 value of 46 nM.2 At 50 nM, CYM 5442 can induce S1P1-dependent lymphopenia in mice, decreasing B and T cells by 65 and 85%, respectively.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Rosen, H., Stevens, R.C., Hanson, M., et al. Sphingosine-1-phosphate and its receptors: Structure, signaling, and influence. Annu. Rev. Biochem. 82, 637-662 (2013).

    2. Gonzalez-Cabrera, P.J., Jo, E., Sanna, M.G., et al. Full pharmacological efficacy of a novel S1P1 agonist that does not require S1P-like headgroup interactions. Mol. Pharmacol. 74(5), 1308-1318 (2008).