X-165   Click here for help

GtoPdb Ligand ID: 11115

Synonyms: compound 1 [PMID: 32584034] | X165
PDB Ligand
Compound class: Synthetic organic
Comment: X-165 is a potent, selective, and bioavailable small molecule inhibitor of the LPA synthetic phosphodiesterase, autotaxin [1]. Autotaxin inhibitors are investigated for their anti-fibrotic potential, and X-165 was developed for potential to treat idiopathic pulmonary fibrosis (IPF). Analysis of autotaxin/X-165 complex crystals revealed that this compound binds to a site on the enzyme that is distinct from the binding site of exisiting inhibitors. Its binding pose shares some similarity with that of ziritaxestat (GLPG1690), but retains crucial differences.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 118.71
Molecular weight 588.21
XLogP 3.75
No. Lipinski's rules broken 0
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Canonical SMILES CC([C@H](C(=O)N1CCC2(CC1)N(c1ccc3c(c1)cn[nH]3)C(=O)N(C2=O)C)NC(=O)c1cc(ccc1F)C(F)(F)F)C
Isomeric SMILES CC([C@H](C(=O)N1CCC2(CC1)N(c1ccc3c(c1)cn[nH]3)C(=O)N(C2=O)C)NC(=O)c1cc(ccc1F)C(F)(F)F)C
InChI InChI=1S/C28H28F4N6O4/c1-15(2)22(34-23(39)19-13-17(28(30,31)32)4-6-20(19)29)24(40)37-10-8-27(9-11-37)25(41)36(3)26(42)38(27)18-5-7-21-16(12-18)14-33-35-21/h4-7,12-15,22H,8-11H2,1-3H3,(H,33,35)(H,34,39)/t22-/m1/s1
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
Synonyms Click here for help
compound 1 [PMID: 32584034] | X165
Database Links Click here for help
BindingDB Ligand 369940
GtoPdb PubChem SID 434122175
PubChem CID 118417573
Search Google for chemical match using the InChIKey CDSKRHGFXHZEQL-JOCHJYFZSA-N
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