compound 9 [Kumar et al., 2019]   Click here for help

GtoPdb Ligand ID: 10448

Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Compound 9 is an example of a new chemotype (with a cyclic enaminone structural scaffold) for selective COX2 inhibitors (COXIBs) [1]. It is hoped that this new chemotype will be devoid of the side effects related to the sulfonamide/sulfonate group common in existing COXIB drugs, and thus lead the way to overcoming the adverse cardiovascular effects that have led to the withdrawl of some existing COXIBs from use in the clinic (rofecoxib and valdecoxib).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 0
Rotatable bonds 3
Topological polar surface area 37.38
Molecular weight 263.07
XLogP 2.17
No. Lipinski's rules broken 0
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Canonical SMILES CC(=O)N(c1ccc(cc1)Cl)C1=CC(=O)CCC1
Isomeric SMILES CC(=O)N(c1ccc(cc1)Cl)C1=CC(=O)CCC1
InChI InChI=1S/C14H14ClNO2/c1-10(17)16(12-7-5-11(15)6-8-12)13-3-2-4-14(18)9-13/h5-9H,2-4H2,1H3
Bioactivity Comments
Compound 9 is ~110-fold selective for COX2 compared to COX1 in vitro [1].
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
COX-2 Primary target of this compound Hs Inhibitor Inhibition 6.4 pIC50 - 1
pIC50 6.4 (IC50 3.67x10-7 M) [1]
Description: Inhibition of recombinant hCOX2 in vitro.
COX-1 Oa Inhibitor Inhibition 4.4 pIC50 - 1
pIC50 4.4 (IC50 3.992x10-5 M) [1]
Description: Inhibition of ovine COX1 using a proprietary COX inhibitor screening assay kit (Cayman chemical company).