AZ11657312 (salt free)   

GtoPdb Ligand ID: 7722

Compound class: Synthetic organic
Comment: The monohydrochloride is described in the article [2], which provides the IUPAC name, 2-(adamantan-1-yl)-N-[2-methyl-5-(9-oxa-3,7-diazabicyclo[3.3.1]non-3-ylcarbonyl)phenyl]acetamide monohydrochloride, for this compound. We represent the molecule here, without the hydrochloride. AZ11657312 is an antagonist of the purinergic receptor 2X, ligand-gated ion channel 7 (P2X7) which is implicated the molecular mechanisms underlying pain and inflammation, as its activation leads to the release of proinflammatory cytokines such as interleukin (IL)-1, tumor necrosis factor (TNF)-α, and IL-6 [3-4]. AZ11657312 has been investigated as an antiinflammatory treatment for conditions such as COPD, Crohn's disease and osteo- and rheumatoid arthritis.
This compound is now included in AstaZeneca's Open Innovation Pharmacology Toolbox.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 70.67
Molecular weight 437.27
XLogP 4.27
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES O=C(CC12CC3CC(C2)CC(C1)C3)Nc1cc(ccc1C)C(=O)N1CC2CNCC(C1)O2
Isomeric SMILES O=C(CC12CC3CC(C2)CC(C1)C3)Nc1cc(ccc1C)C(=O)N1CC2CNCC(C1)O2
InChI InChI=1S/C26H35N3O3/c1-16-2-3-20(25(31)29-14-21-12-27-13-22(15-29)32-21)7-23(16)28-24(30)11-26-8-17-4-18(9-26)6-19(5-17)10-26/h2-3,7,17-19,21-22,27H,4-6,8-15H2,1H3,(H,28,30)
InChI Key XYNNEMHCLNODBL-UHFFFAOYSA-N
Classification
Compound class Synthetic organic
IUPAC Name
2-(1-adamantyl)-N-[2-methyl-5-(9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carbonyl)phenyl]acetamide
Database Links
ChEMBL Ligand CHEMBL550637
GtoPdb PubChem SID 223366055
PubChem CID 11193842
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