compound 4f [PMID: 34328319]   Click here for help

GtoPdb Ligand ID: 11733

PDB Ligand
Compound class: Synthetic organic
Comment: Compound 4f is a potent and reversible monoacylglycerol lipase (MAGL) inhibitor [1]. In the brain, MAGL is the primary enzyme that degrades the endocannabinoid 2-arachidonoylglycerol (2-AG) to arachidonic acid (AA) and glycerol. Inhibition of MAGL (to increase 2-AG and reduce AA) is being investigated for therapeutic potential in a range of neuroinflammatory type diseases. Compound 4f is useful because it is reversible, it can cross the blood-brain barrier, and it induces the expected pharmacodynamic effects in in vivo models.
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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 5
Topological polar surface area 67.87
Molecular weight 364.12
XLogP 1.75
No. Lipinski's rules broken 0
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Canonical SMILES O=C1OC[C@@]2(N1)C[C@@H](C2)C(=O)N1CC(C1)OCc1ccc(c(c1)Cl)C
Isomeric SMILES Cc1c(Cl)cc(COC2CN(C2)C(=O)[C@H]2C[C@@]3(C2)COC(=O)N3)cc1
InChI InChI=1S/C18H21ClN2O4/c1-11-2-3-12(4-15(11)19)9-24-14-7-21(8-14)16(22)13-5-18(6-13)10-25-17(23)20-18/h2-4,13-14H,5-10H2,1H3,(H,20,23)/t13-,18+
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
Database Links Click here for help
GtoPdb PubChem SID 458923768
PubChem CID 130475870
Search Google for chemical match using the InChIKey AKBHYCHPWZPGAH-QGGXVJLZSA-N
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UniChem Connectivity Search for chemical match using the InChIKey AKBHYCHPWZPGAH-QGGXVJLZSA-N