BMS-202   Click here for help

GtoPdb Ligand ID: 9607

Synonyms: compound 1c [PMID: 28613862] | PD1-PDL1 inhibitor 2
PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: BMS-202 is a small molecule that disrupts the PD-1/PD-L1 immune checkpoint interaction. It is the most potent of the (2-methyl-3-biphenylyl)methanol derivatives described in [2]. NMR analysis suggests that BMS-202 promotes the formation of dimeric PD-L1 in solution. The X-ray crystal structure of the complex is deposited in the PDB, with accession 5J89 [3].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 11
Topological polar surface area 72.48
Molecular weight 419.22
XLogP 5.16
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES COc1nc(OCc2cccc(c2C)c2ccccc2)ccc1CNCCNC(=O)C
Isomeric SMILES COc1nc(OCc2cccc(c2C)c2ccccc2)ccc1CNCCNC(=O)C
InChI InChI=1S/C25H29N3O3/c1-18-22(10-7-11-23(18)20-8-5-4-6-9-20)17-31-24-13-12-21(25(28-24)30-3)16-26-14-15-27-19(2)29/h4-13,26H,14-17H2,1-3H3,(H,27,29)
InChI Key JEDPSOYOYVELLZ-UHFFFAOYSA-N
References
1. Banister SD, Stuart J, Kevin RC, Edington A, Longworth M, Wilkinson SM, Beinat C, Buchanan AS, Hibbs DE, Glass M et al.. (2015)
Effects of bioisosteric fluorine in synthetic cannabinoid designer drugs JWH-018, AM-2201, UR-144, XLR-11, PB-22, 5F-PB-22, APICA, and STS-135.
ACS Chem Neurosci, 6 (8): 1445-58. [PMID:25921407]
2. Guzik K, Zak KM, Grudnik P, Magiera K, Musielak B, Törner R, Skalniak L, Dömling A, Dubin G, Holak TA. (2017)
Small-Molecule Inhibitors of the Programmed Cell Death-1/Programmed Death-Ligand 1 (PD-1/PD-L1) Interaction via Transiently Induced Protein States and Dimerization of PD-L1.
J. Med. Chem., 60 (13): 5857-5867. [PMID:28613862]
3. Zak KM, Grudnik P, Guzik K, Zieba BJ, Musielak B, Dömling A, Dubin G, Holak TA. (2016)
Structural basis for small molecule targeting of the programmed death ligand 1 (PD-L1).
Oncotarget, 7 (21): 30323-35. [PMID:27083005]