CYM 5541Selective S1P3 receptor allosteric agonist CAS# 945128-26-7 |
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Quality Control & MSDS
3D structure
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| Cas No. | 945128-26-7 | SDF | Download SDF |
| PubChem ID | 17253208 | Appearance | Powder |
| Formula | C19H28N2O2 | M.Wt | 316.44 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Synonyms | ML249 | ||
| Solubility | DMSO : 25 mg/mL (79.00 mM; Need ultrasonic) | ||
| Chemical Name | N,N-dicyclohexyl-5-cyclopropyl-1,2-oxazole-3-carboxamide | ||
| SMILES | C1CCC(CC1)N(C2CCCCC2)C(=O)C3=NOC(=C3)C4CC4 | ||
| Standard InChIKey | NDKGACIWVAOUQH-UHFFFAOYSA-N | ||
| Standard InChI | InChI=1S/C19H28N2O2/c22-19(17-13-18(23-20-17)14-11-12-14)21(15-7-3-1-4-8-15)16-9-5-2-6-10-16/h13-16H,1-12H2 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Selective sphingosine-1-phosphate receptor 3 (S1P3) allosteric agonist (EC50 = 72-132 nM). Occupies a different space within the ligand binding pocket of S1P3 than S1P. Displays no activity at S1P1, S1P2, S1P4 and S1P5 receptors at concentrations up to 10 μM. Shows no significant activities in a profiling panel of 55 GPCRs, ion channels and transporters. |
CYM 5541 Dilution Calculator
CYM 5541 Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 3.1602 mL | 15.8008 mL | 31.6016 mL | 63.2031 mL | 79.0039 mL |
| 5 mM | 0.632 mL | 3.1602 mL | 6.3203 mL | 12.6406 mL | 15.8008 mL |
| 10 mM | 0.316 mL | 1.5801 mL | 3.1602 mL | 6.3203 mL | 7.9004 mL |
| 50 mM | 0.0632 mL | 0.316 mL | 0.632 mL | 1.2641 mL | 1.5801 mL |
| 100 mM | 0.0316 mL | 0.158 mL | 0.316 mL | 0.632 mL | 0.79 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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CYM-5541 (ML249) is an selective and allosteric S1P3 receptor agonist with an EC50 between 72 and 132 nM.
In Vitro:CYM-5541 is a full agonist, able to reach the maximum level of ERK phosphorylation that is observed with S1P. CYM-5541 has an EC50 of between 72 and 132 nM and exhibits exquisite selectivity over other S1P receptor subtypes: S1P1 EC50>10 μM, S1P2 EC50>50 μM, S1P4 EC50>50 μM, and S1P5 EC50>25 μM. CYM-5541 also shows selectivity over a large panel of protein targets, with no significant activities, in the Ricerca profiling panel of 55 GPCRs, ion channels, and transporters. CYM-5541 allowed us to identify an allosteric site where F263 is a key gate-keeper residue for its affinity and efficacy. The novel allosteric hydrophobic pocket may account for the S1P3 selectivity of CYM-5541[1].
References:
[1]. Jo E, et al. Novel selective allosteric and bitopic ligands for the S1P(3) receptor. ACS Chem Biol. 2012 Dec 21;7(12):1975-83.
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Novel selective allosteric and bitopic ligands for the S1P(3) receptor.[Pubmed:22971058]
ACS Chem Biol. 2012 Dec 21;7(12):1975-83.
Sphingosine 1-phosphate (S1P) is a lysophospholipid signaling molecule that regulates important biological functions, including lymphocyte trafficking and vascular development, by activating G protein-coupled receptors for S1P, namely, S1P(1) through S1P(5). Here, we map the S1P(3) binding pocket with a novel allosteric agonist (CYM-5541), an orthosteric agonist (S1P), and a novel bitopic antagonist (SPM-242). With a combination of site-directed mutagenesis, ligand competition assay, and molecular modeling, we concluded that S1P and CYM-5541 occupy different chemical spaces in the ligand binding pocket of S1P(3). CYM-5541 allowed us to identify an allosteric site where Phe263 is a key gate-keeper residue for its affinity and efficacy. This ligand lacks a polar moiety, and the novel allosteric hydrophobic pocket permits S1P(3) selectivity of CYM-5541 within the highly similar S1P receptor family. However, a novel S1P(3)-selective antagonist, SPM-242, in the S1P(3) pocket occupies the ligand binding spaces of both S1P and CYM-5541, showing its bitopic mode of binding. Therefore, our coordinated approach with biochemical data and molecular modeling, based on our recently published S1P(1) crystal structure data in a highly conserved set of related receptors with a shared ligand, provides a strong basis for the successful optimization of orthosteric, allosteric, and bitopic modulators of S1P(3).
