(S)-23 [PMID: 27933945]   Click here for help

GtoPdb Ligand ID: 9796

PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Compound (S)-23 is a γ-lactam sulfone type PLA2-G7 (Lp-PLA2) inhibitor [3]. It is less lipophilic than the clinically evaluated inhibitor, darapladib.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 0
Rotatable bonds 5
Topological polar surface area 95.85
Molecular weight 394.14
XLogP 2.41
No. Lipinski's rules broken 0
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Canonical SMILES N#Cc1cc(OCCN2CC(CC2=O)C2(C)CCS(=O)(=O)CC2)ccc1F
Isomeric SMILES N#Cc1cc(OCCN2C[C@@H](CC2=O)C2(C)CCS(=O)(=O)CC2)ccc1F
InChI InChI=1S/C19H23FN2O4S/c1-19(4-8-27(24,25)9-5-19)15-11-18(23)22(13-15)6-7-26-16-2-3-17(20)14(10-16)12-21/h2-3,10,15H,4-9,11,13H2,1H3/t15-/m1/s1
1. Staurenghi G, Ye L, Magee MH, Danis RP, Wurzelmann J, Adamson P, McLaughlin MM, Darapladib DME Study Group. (2015)
Darapladib, a lipoprotein-associated phospholipase A2 inhibitor, in diabetic macular edema: a 3-month placebo-controlled study.
Ophthalmology, 122 (5): 990-6. [PMID:25749297]
2. Tjoelker LW, Wilder C, Eberhardt C, Stafforini DM, Dietsch G, Schimpf B, Hooper S, Le Trong H, Cousens LS, Zimmerman GA et al.. (1995)
Anti-inflammatory properties of a platelet-activating factor acetylhydrolase.
Nature, 374 (6522): 549-53. [PMID:7700381]
3. Woolford AJ, Day PJ, Bénéton V, Berdini V, Coyle JE, Dudit Y, Grondin P, Huet P, Lee LY, Manas ES et al.. (2016)
Fragment-Based Approach to the Development of an Orally Bioavailable Lactam Inhibitor of Lipoprotein-Associated Phospholipase A2 (Lp-PLA2).
J Med Chem, 59 (23): 10738-10749. [PMID:27933945]