KML29   Click here for help

GtoPdb Ligand ID: 9482

Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: KML29 is a highly selective and potent monoacylglycerol lipase (MAGL) inhibitor. MAGL is the primary catabolic enzyme of the endogenous endocannabinoid 2-arachidonoylglycerol (2-AG). Selective MAGL inhibitors can be used as probes to investigate the consequences of elevating circulating levels of 2-AG levels in vivo.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 8
Topological polar surface area 86.69
Molecular weight 549.12
XLogP 5.56
No. Lipinski's rules broken 1
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Canonical SMILES O=C(N1CCC(CC1)C(c1ccc2c(c1)OCO2)(c1ccc2c(c1)OCO2)O)OC(C(F)(F)F)C(F)(F)F
Isomeric SMILES O=C(N1CCC(CC1)C(c1ccc2c(c1)OCO2)(c1ccc2c(c1)OCO2)O)OC(C(F)(F)F)C(F)(F)F
InChI InChI=1S/C24H21F6NO7/c25-23(26,27)20(24(28,29)30)38-21(32)31-7-5-13(6-8-31)22(33,14-1-3-16-18(9-14)36-11-34-16)15-2-4-17-19(10-15)37-12-35-17/h1-4,9-10,13,20,33H,5-8,11-12H2
1. Chang JW, Niphakis MJ, Lum KM, Cognetta 3rd AB, Wang C, Matthews ML, Niessen S, Buczynski MW, Parsons LH, Cravatt BF. (2012)
Highly selective inhibitors of monoacylglycerol lipase bearing a reactive group that is bioisosteric with endocannabinoid substrates.
Chem Biol, 19 (5): 579-88. [PMID:22542104]
2. Ignatowska-Jankowska BM, Ghosh S, Crowe MS, Kinsey SG, Niphakis MJ, Abdullah RA, Tao Q, O' Neal ST, Walentiny DM, Wiley JL et al.. (2014)
In vivo characterization of the highly selective monoacylglycerol lipase inhibitor KML29: antinociceptive activity without cannabimimetic side effects.
Br J Pharmacol, 171 (6): 1392-407. [PMID:23848221]