ABX-1431   Click here for help

GtoPdb Ligand ID: 10062

Synonyms: ABX1431 | compound 28 [PMID: 30067909] | compound 9aq [WO2013103973A1] | example 82 [WO2013103973A1]
Compound class: Synthetic organic
Comment: ABX-1431 is a potent, orally available, and selective covalent (irreversible) inhibitor of monoacylglycerol lipase (MGLL) [2]. It is one of the chemical structures that are claimed in patent WO2013103973A1 [1]. MGLL inhibition increases the level of the endogenous cannabinoid receptor agonist 2-arachidonoylglycerol (2-AG) and CB1 receptor signalling in the central nervous system, and reduces arachidonic acid and eicosanoid levels to better regulate neurotransmission. Modulation of these neurotransmitter molecules induces antinociceptive, anxiolytic, and antineuroinflammatory effects, but is devoid of the psychoactive effects that would be produced by direct cannabinoid receptor activation. Target engagement by ABX-1431 in the brain has been confirmed in a PET occupancy study [1].
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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 9
Topological polar surface area 36.02
Molecular weight 507.16
XLogP 6.02
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES O=C(N1CCN(CC1)Cc1ccc(cc1N1CCCC1)C(F)(F)F)OC(C(F)(F)F)C(F)(F)F
Isomeric SMILES O=C(N1CCN(CC1)Cc1ccc(cc1N1CCCC1)C(F)(F)F)OC(C(F)(F)F)C(F)(F)F
InChI InChI=1S/C20H22F9N3O2/c21-18(22,23)14-4-3-13(15(11-14)31-5-1-2-6-31)12-30-7-9-32(10-8-30)17(33)34-16(19(24,25)26)20(27,28)29/h3-4,11,16H,1-2,5-10,12H2
InChI Key SQZJGTOZFRNWCX-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
1,1,1,3,3,3-hexafluoropropan-2-yl 4-[[2-pyrrolidin-1-yl-4-(trifluoromethyl)phenyl]methyl]piperazine-1-carboxylate
Synonyms Click here for help
ABX1431 | compound 28 [PMID: 30067909] | compound 9aq [WO2013103973A1] | example 82 [WO2013103973A1]
Database Links Click here for help
BindingDB Ligand 180052
ChEMBL Ligand CHEMBL3945728
GtoPdb PubChem SID 375973250
PubChem CID 71657619
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