Galapagos MAPKAPK5 inhibitor D   

GtoPdb Ligand ID: 9848

Synonyms: compound 183 [WO2007138072A2]
Compound class: Synthetic organic
Comment: This compound was developed by Galapagos as a MAPKAPK5 inhibitor, in the search for a novel anti-inflammatory mechanism that would be applicable to the treatment of rheumatoid arthritis (RA). The discovery pathway is detailed in the pdf entitled 'Discovery of inhibitors of MAPKAPK5, a novel target for rheumatoid arthritis', which is available online here. The chemical structure is claimed in Galapagos patent WO2007138072A2, as compound 183 [2]. This compound (compound D) is likely to be a relation of the Galapagos clinical candidate GLPG0259, which failed in Phase 2 clinical trial in patients with methotrexate-refractory RA [3].
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 8
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 117.82
Molecular weight 460.23
XLogP 2.22
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES NC(=O)c1occ(c1)c1cnc(c2n1ncn2)Nc1ccc(cc1)N1CCN(CC1)C(C)(C)C
Isomeric SMILES NC(=O)c1occ(c1)c1cnc(c2n1ncn2)Nc1ccc(cc1)N1CCN(CC1)C(C)(C)C
InChI InChI=1S/C24H28N8O2/c1-24(2,3)31-10-8-30(9-11-31)18-6-4-17(5-7-18)29-22-23-27-15-28-32(23)19(13-26-22)16-12-20(21(25)33)34-14-16/h4-7,12-15H,8-11H2,1-3H3,(H2,25,33)(H,26,29)
InChI Key DLGZLIXYVSQGOX-UHFFFAOYSA-N
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Molecular structure representations generated using Open Babel