GLPG0974   Click here for help

GtoPdb Ligand ID: 8417

Synonyms: compound 99 [PMID 25380412]
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: GLPG0974 was a lead clinical development candidate. It acts as an antagonist of the free fatty acid receptor 2 (FFA2) [3]. FFA2 is a GPCR involved in the mediation of inflammatory responses.
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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 10
Topological polar surface area 106.16
Molecular weight 484.12
XLogP 4.17
No. Lipinski's rules broken 0
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Canonical SMILES OC(=O)CCCN(C(=O)C1(C)CCN1C(=O)c1csc2c1cccc2)Cc1cccc(c1)Cl
Isomeric SMILES OC(=O)CCCN(C(=O)[C@@]1(C)CCN1C(=O)c1csc2c1cccc2)Cc1cccc(c1)Cl
InChI InChI=1S/C25H25ClN2O4S/c1-25(11-13-28(25)23(31)20-16-33-21-9-3-2-8-19(20)21)24(32)27(12-5-10-22(29)30)15-17-6-4-7-18(26)14-17/h2-4,6-9,14,16H,5,10-13,15H2,1H3,(H,29,30)/t25-/m1/s1
1. Cerep. 
ExpresSProfile - P1.
Accessed on 08/06/2015. Modified on 08/06/2015.,
2. Namour F, Galien R, Van Kaem T, Van der Aa A, Vanhoutte F, Beetens J, Van't Klooster G. (2016)
Safety, pharmacokinetics and pharmacodynamics of GLPG0974, a potent and selective FFA2 antagonist, in healthy male subjects.
Br J Clin Pharmacol, 82 (1): 139-48. [PMID:26852904]
3. Pizzonero M, Dupont S, Babel M, Beaumont S, Bienvenu N, Blanqué R, Cherel L, Christophe T, Crescenzi B, De Lemos E et al.. (2014)
Discovery and optimization of an azetidine chemical series as a free fatty acid receptor 2 (FFA2) antagonist: from hit to clinic.
J Med Chem, 57 (23): 10044-57. [PMID:25380412]