compound 39 [PMID: 31742400]   Click here for help

GtoPdb Ligand ID: 10585

Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Compound 39 is a dual antagonist of the CC-chemokine receptors CCR2 and CCR5 [3]. It is one of the most potent lead molecules that were reported in this 2019 Journal of Medicinal Chemistry paper. Experiments measuring antagonism of CCL3-induced [35S]GTPγS binding indicates that 39 binds to an allosteric site of both target receptors, which is likely to be located on the intracellular face of the receptiors. The compound is described as an insurmountable antagonist.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 89.07
Molecular weight 351.07
XLogP 3.79
No. Lipinski's rules broken 0
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Canonical SMILES Nc1nn2c(n1)[nH]c(c(c2=O)Cc1cccc(c1Cl)Cl)C(C)C
Isomeric SMILES Nc1nn2c(n1)[nH]c(c(c2=O)Cc1cccc(c1Cl)Cl)C(C)C
InChI InChI=1S/C15H15Cl2N5O/c1-7(2)12-9(6-8-4-3-5-10(16)11(8)17)13(23)22-15(19-12)20-14(18)21-22/h3-5,7H,6H2,1-2H3,(H3,18,19,20,21)
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
CCR2 Hs Allosteric modulator Antagonist 8.8 pKi - 3
pKi 8.8 (Ki 1.6x10-9 M) [3]
Description: Binding affinity determined from a radioligand binding assay, measuring displacement of [3H]-CCR2-RA-[R] from U2OS cells stably expressing human CCR2.
CCR5 Hs Allosteric modulator Antagonist 7.1 pIC50 - 3
pIC50 7.1 (IC50 8.4x10-8 M) [3]
Description: Antagonist effect on CCL3-induced β-arrestin recruitment in U2OS cells stably expressing human CCR5.