BMS-1166   

GtoPdb Ligand ID: 9608

Synonyms: compound 2c [PMID: 28613862] | Example 1166 [WO2015160641A2]
Compound class: Synthetic organic
Comment: BMS-1166 is a small molecule that disrupts the PD-1/PD-L1 immune checkpoint interaction. It is the most potent of the [3-(2,3-Dihydro-1,4-benzodioxin-6-yl)-2-methylphenyl]methanol derivatives described in [2], and it is claimed as Example 1166 in Bristol-Myers Squibb's patent WO2015160641A2 [1]. NMR analysis suggests that BMS-1166 promotes the formation of dimeric PD-L1 in solution.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 2
Rotatable bonds 10
Topological polar surface area 121.48
Molecular weight 640.2
XLogP 6.06
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES N#Cc1cccc(c1)COc1cc(OCc2cccc(c2C)c2ccc3c(c2)OCCO3)c(cc1CN1CC(CC1C(=O)O)O)Cl
Isomeric SMILES N#Cc1cccc(c1)COc1cc(OCc2cccc(c2C)c2ccc3c(c2)OCCO3)c(cc1CN1C[C@@H](C[C@@H]1C(=O)O)O)Cl
InChI InChI=1S/C36H33ClN2O7/c1-22-26(6-3-7-29(22)25-8-9-32-35(14-25)44-11-10-43-32)21-46-34-16-33(45-20-24-5-2-4-23(12-24)17-38)27(13-30(34)37)18-39-19-28(40)15-31(39)36(41)42/h2-9,12-14,16,28,31,40H,10-11,15,18-21H2,1H3,(H,41,42)/t28-,31-/m1/s1
InChI Key QBXVXKRWOVBUDB-GRKNLSHJSA-N
Classification
Compound class Synthetic organic
IUPAC Name
(2R,4R)-1-[[5-chloro-2-[(3-cyanophenyl)methoxy]-4-[[3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-methylphenyl]methoxy]phenyl]methyl]-4-hydroxypyrrolidine-2-carboxylic acid
Synonyms
compound 2c [PMID: 28613862] | Example 1166 [WO2015160641A2]
Database Links
GtoPdb PubChem SID 340590238
PubChem CID 118434635
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