compound 10 [PMID: 31411465]   Click here for help

GtoPdb Ligand ID: 10488

Synonyms: example 8 (cis racemate) [WO2017060855A1]
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Compound 10 is small molecule that binds to KEAP1 and prevents its interaction with the Nrf2 transcription factor [2]. It acts as a functional activator of Nrf2-mediated gene transcription. The chemical structure was originally claimed in a Glaxosmithkline/Astex Therapeutics patent [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 9
Topological polar surface area 74.91
Molecular weight 463.28
XLogP 5.72
No. Lipinski's rules broken 1
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Canonical SMILES CCCCC1CCCN1C(=O)C1CCCC(C1)c1cccc(c1)n1ncc(c1C1CC1)C(=O)O
Isomeric SMILES CCCCC1CCCN1C(=O)[C@@H]1CCC[C@@H](C1)c1cccc(c1)n1ncc(c1C1CC1)C(=O)O
InChI InChI=1S/C28H37N3O3/c1-2-3-10-23-12-6-15-30(23)27(32)22-9-4-7-20(16-22)21-8-5-11-24(17-21)31-26(19-13-14-19)25(18-29-31)28(33)34/h5,8,11,17-20,22-23H,2-4,6-7,9-10,12-16H2,1H3,(H,33,34)/t20-,22+,23?/m0/s1
1. Callahan JF, Kerns JK, Li T, Mccleland BW, Nie H, Pero JE, Davies TG, Heightman TD, Griffiths-Jones CM, Howard S et al.. (2017)
Arylcyclohexyl pyrazoles as nrf2 regulators.
Patent number: WO2017060855A1. Assignee: Glaxosmithkline Intellectual Property Development Limited, Astex Therapeutics Limited. Priority date: 06/10/2015. Publication date: 13/04/2017.
2. Tran KT, Pallesen JS, Solbak SMØ, Narayanan D, Baig A, Zang J, Aguayo-Orozco A, Carmona RMC, Garcia AD, Bach A. (2019)
A Comparative Assessment Study of Known Small-Molecule Keap1-Nrf2 Protein-Protein Interaction Inhibitors: Chemical Synthesis, Binding Properties, and Cellular Activity.
J Med Chem, 62 (17): 8028-8052. [PMID:31411465]