PF-06650833   

GtoPdb Ligand ID: 9667

Synonyms: compound 40 [PMID: 28498658] | PF06650833
Compound class: Synthetic organic
Comment: PF-06650833 is a small molecule, reversible, potent and selective IRAK4 inhibitor identified as a clinical lead [1]. Its pharmacokinetic profile suggests it will be orally bioavailable. Structurally it is an analogue of PF-06426779.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 103.54
Molecular weight 361.14
XLogP 2
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CCC1C(COc2nccc3c2cc(OC)c(c3)C(=O)N)NC(=O)C1F
Isomeric SMILES CC[C@H]1[C@@H](COc2nccc3c2cc(OC)c(c3)C(=O)N)NC(=O)[C@H]1F
InChI InChI=1S/C18H20FN3O4/c1-3-10-13(22-17(24)15(10)19)8-26-18-11-7-14(25-2)12(16(20)23)6-9(11)4-5-21-18/h4-7,10,13,15H,3,8H2,1-2H3,(H2,20,23)(H,22,24)/t10-,13+,15-/m0/s1
InChI Key JKDGKIBAOAFRPJ-ZBINZKHDSA-N
References
1. Lee KL, Ambler CM, Anderson DR, Boscoe BP, Bree AG, Brodfuehrer JI, Chang JS, Choi C, Chung S, Curran KJ et al.. (2017)
Discovery of Clinical Candidate 1-{[(2S,3S,4S)-3-Ethyl-4-fluoro-5-oxopyrrolidin-2-yl]methoxy}-7-methoxyisoquinoline-6-carboxamide (PF-06650833), a Potent, Selective Inhibitor of Interleukin-1 Receptor Associated Kinase 4 (IRAK4), by Fragment-Based Drug Design.
J. Med. Chem., 60 (13): 5521-5542. [PMID:28498658]