MRE-269   Click here for help

GtoPdb Ligand ID: 5852

Synonyms: ACT 333679 | ACT-333679 | MRE 269
Compound class: Synthetic organic
Comment: MRE-269 is the active metabolite of the approved drug selexipag. MRE-269 behaves as a partial agonist in cAMP assays [3].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 1
Rotatable bonds 11
Topological polar surface area 75.55
Molecular weight 419.22
XLogP 5.3
No. Lipinski's rules broken 2
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Canonical SMILES OC(=O)COCCCCN(c1cnc(c(n1)c1ccccc1)c1ccccc1)C(C)C
Isomeric SMILES OC(=O)COCCCCN(c1cnc(c(n1)c1ccccc1)c1ccccc1)C(C)C
InChI InChI=1S/C25H29N3O3/c1-19(2)28(15-9-10-16-31-18-23(29)30)22-17-26-24(20-11-5-3-6-12-20)25(27-22)21-13-7-4-8-14-21/h3-8,11-14,17,19H,9-10,15-16,18H2,1-2H3,(H,29,30)
1. Asaki T, Hamamoto T, Sugiyama Y, Kuwano K, Kuwabara K. (2007)
Structure-activity studies on diphenylpyrazine derivatives: a novel class of prostacyclin receptor agonists.
Bioorg Med Chem, 15 (21): 6692-704. [PMID:17764960]
2. Benyahia C, Boukais K, Gomez I, Silverstein A, Clapp L, Fabre A, Danel C, Leséche G, Longrois D, Norel X. (2013)
A comparative study of PGI2 mimetics used clinically on the vasorelaxation of human pulmonary arteries and veins, role of the DP-receptor.
Prostaglandins Other Lipid Mediat, 107: 48-55. [PMID:23850788]
3. Gatfield J, Menyhart K, Wanner D, Gnerre C, Monnier L, Morrison K, Hess P, Iglarz M, Clozel M, Nayler O. (2017)
Selexipag Active Metabolite ACT-333679 Displays Strong Anticontractile and Antiremodeling Effects but Low β-Arrestin Recruitment and Desensitization Potential.
J Pharmacol Exp Ther, 362 (1): 186-199. [PMID:28476928]
4. Kuwano K, Hashino A, Asaki T, Hamamoto T, Yamada T, Okubo K, Kuwabara K. (2007)
2-[4-[(5,6-diphenylpyrazin-2-yl)(isopropyl)amino]butoxy]-N-(methylsulfonyl)acetamide (NS-304), an orally available and long-acting prostacyclin receptor agonist prodrug.
J Pharmacol Exp Ther, 322 (3): 1181-8. [PMID:17545310]