AGU654   Click here for help

GtoPdb Ligand ID: 13646

Synonyms: AGU-654 | compound 44 [PMID: 39622054]
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: AGU654 is a small molecule inhibitor of the microsomal enzyme prostaglandin E2 synthase 1 (mPGES1; the primary producer of proinflammatory PGE2) [1]. It is proposed to reduce inflammation and inflammatory pain, via suppression of prostaglandin E2 synthesis.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 3
Rotatable bonds 10
Topological polar surface area 82.59
Molecular weight 580.91
XLogP 3.65
No. Lipinski's rules broken 1

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

SMILES / InChI / InChIKey
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Canonical SMILES C1=C(C=C(C(=C1)Cl)C(=O)NC2=CC=C(C=C2)C3=NC4=C(C=CC(=C4)C(F)(F)F)N3)CNC(=O)C5(CC5)C(F)(F)F
Isomeric SMILES ClC1=C(C(=O)NC2=CC=C(C=C2)C3=NC4=C(N3)C=CC(=C4)C(F)(F)F)C=C(C=C1)CNC(=O)C5(CC5)C(F)(F)F
InChI InChI=1S/C27H19ClF6N4O2/c28-19-7-1-14(13-35-24(40)25(9-10-25)27(32,33)34)11-18(19)23(39)36-17-5-2-15(3-6-17)22-37-20-8-4-16(26(29,30)31)12-21(20)38-22/h1-8,11-12H,9-10,13H2,(H,35,40)(H,36,39)(H,37,38)
InChI Key QLJJIKAYPMNUEM-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

References
1. Ergül AG, Jordan PM, Dahlke P, Bal NB, Olğaç A, Uludağ O, Werz O, Çalışkan B, Banoglu E. (2024)
Novel Benzimidazole Derivatives as Potent Inhibitors of Microsomal Prostaglandin E2 Synthase 1 for the Potential Treatment of Inflammation, Pain, and Fever.
J Med Chem, [Epub ahead of print]. [PMID:39622054]