5-LOX inhibitor 2m [PMID: 30199704]   Click here for help

GtoPdb Ligand ID: 10079

Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Compound 2m is reported as a competitive inhibitor of the 5-lipoxygenase (5-LOX) enzyme. It was developed for anti-inflammatory potential [4]. 2m was the most active inhibtor identified from the thiazole series in this pharmacophore modeling study. The thiazole series of compounds was designed with the aim of reducing the hepatotoxicity that is associated with N-hydroxyurea class 5-LOX inhibitors [3] such as zileuton, atreleuton (ABT-761; PubChem CID 3086671) [1] and MLN-977 (PubChem CID 9905233) [2]. 2m is devoid of radical scavenging activity.
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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 7
Topological polar surface area 70.67
Molecular weight 462.14
XLogP 7.29
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES COc1ccc(cc1)c1nc(sc1C(=O)c1ccccc1)N(c1ccccc1)c1ccccc1
Isomeric SMILES COc1ccc(cc1)c1nc(sc1C(=O)c1ccccc1)N(c1ccccc1)c1ccccc1
InChI InChI=1S/C29H22N2O2S/c1-33-25-19-17-21(18-20-25)26-28(27(32)22-11-5-2-6-12-22)34-29(30-26)31(23-13-7-3-8-14-23)24-15-9-4-10-16-24/h2-20H,1H3
InChI Key GCBYJNQEZBSRJO-UHFFFAOYSA-N
Immunopharmacology Comments
Human 5-LOX is a key enzyme that is targeted for asthma and inflammation using inhibitor compounds. The first 5-LOX inhibitor to reach the clinic was zileuton.