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Compound Detail

CHEMBL41275

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Cc1ccc(-c2ccc3c(c2)C=C(C(=O)Nc2ccc(C[N+](C)(C)C4CCOCC4)cc2)CCC3)cc1.[Cl-]
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL41275
Phase Preclinical
Structure Type MOL
InChI Key VDALIBWXVQVFGZ-UHFFFAOYSA-N
Parent Compound CHEMBL1178786
Active Moiety CHEMBL1178786
10
Targets
62
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

495.7
MW (Da)
6.78
ALogP
2
HBA
1
HBD
38.3
PSA (Ų)
0.38
QED
1
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C33H39ClN2O2
MW 531.14
Aromatic Rings 3
Heavy Atoms 37
NP-Likeness -0.46

Activity Summary

IC50 44 meas. best 10.52
Ki 15 meas. best 8.7
EC50 3 meas. best 8.92

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
C-C chemokine receptor type 2
CHEMBL4015
 IC50 10.52 8.2244 0.0 16
C-C chemokine receptor type 5
CHEMBL274
 IC50 8.92 8.7283 1.2 12
Unchecked
CHEMBL612545
 EC50 8.92 8.92 1.2 1
C-C chemokine receptor type 7
CHEMBL4594
 IC50 8.85 8.85 1.4 1
CHO
CHEMBL613853
 IC50 8.85 8.85 1.4 1
C-C chemokine receptor type 2
CHEMBL4015
 Ki 8.7 7.5913 2.0 15
Human immunodeficiency virus 1
CHEMBL378
 EC50 8.43 8.43 3.7 1
C-C chemokine receptor type 5
CHEMBL274
 EC50 8.15 8.15 7.0 1
Human immunodeficiency virus 1
CHEMBL378
 IC50 7.85 7.2057 14.0 7
Unchecked
CHEMBL612545
 IC50 7.72 7.72 19.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.69 4.69 20400.0 1
C-C chemokine receptor type 2
CHEMBL5412
 IC50 4.64 4.64 23000.0 1
C-X-C chemokine receptor type 3
CHEMBL4441
 IC50 4.5 4.5 31300.0 2
PC-3
CHEMBL390
 IC50 4.42 4.42 37850.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
C-C chemokine receptor type 2 IC50 = 0.03 nM 10.52 Displacement of [125I]MCP1 from CCR2/CXCR4 expressed in CHOK1 cells 17715128
C-C chemokine receptor type 2 IC50 = 0.08 nM 10.1 Displacement of [125I]SDF1alpha from CCR2/CXCR4 expressed in CHOK1 cells 17715128
C-C chemokine receptor type 2 IC50 = 0.25 nM 9.6 Displacement of [125I]MCP1 from CCR2 expressed in CHOK1 cells 17715128
C-C chemokine receptor type 2 IC50 = 0.95 nM 9.02 Antagonist activity against human CCR2B expressed in Chem-1 cells assessed as in... 25766632
C-C chemokine receptor type 2 IC50 = 0.95 nM 9.02 Antagonist activity at human CCR2b expressed in human Chem1 cells assessed as in... 28463783
Unchecked EC50 = 1.2 nM 8.92 Inhibitory effects on HIV-1 (Ba-L) replication was evaluated in MAGI-CCR5 cells 10821717
C-C chemokine receptor type 5 IC50 = 1.2 nM 8.92 Inhibition of chemotactic protein to CCR5 11931608
C-C chemokine receptor type 5 IC50 = 1.4 nM 8.85 Compound was evaluated for the antagonist activity against C-C chemokine recepto... 10969972
C-C chemokine receptor type 7 IC50 = 1.4 nM 8.85 Inhibition of CCR7 (unknown origin) 31930920
C-C chemokine receptor type 5 IC50 = 1.4 nM 8.85 Displacement of [125I]RANTES from human CCR5 expressed in CHO cells after 40 min... 28463783
C-C chemokine receptor type 5 IC50 = 1.4 nM 8.85 Binding affinity to CCR5 22931505
C-C chemokine receptor type 5 IC50 = 1.4 nM 8.85 Inhibition of CCL5 binding to CCR5 expressed in CHO cells 21820898
C-C chemokine receptor type 5 IC50 = 1.4 nM 8.85 Inhibition of CCR5 19237282
C-C chemokine receptor type 5 IC50 = 1.4 nM 8.85 Inhibition of membrane fusion between HIV1 JR-FL Env-expressing COS7 cells and M... 16539392
C-C chemokine receptor type 5 IC50 = 1.4 nM 8.85 Displacement of [125I]RANTES from CCR5 expressed in CHO cells 16539392
CHO IC50 = 1.4 nM 8.85 Inhibition of [125I]RANTES association with CCR5 expressed in CHO cells at 100 n... 11931608
C-C chemokine receptor type 5 IC50 = 1.4 nM 8.85 Inhibitory effect on Chemokine binding to C-C chemokine receptor type 5 using [1... 10821717
C-C chemokine receptor type 2 Ki = 2.0 nM 8.7 Displacement of [125I]-CCL2 from human CCR2 expressed in U2OS cells incubated fo... 25766632
C-C chemokine receptor type 5 IC50 = 2.0 nM 8.7 Displacement of [3H]TAK-779 from CCR5 (unknown origin) after 120 mins by scintil... 28463783
C-C chemokine receptor type 2 Ki = 2.63 nM 8.58 Binding affinity of compound (10 uM) towards H121F receptor variant (mutant CCR2... 12954060

Literature References

PubMed DOI Target Context # Activities
12954060 10.1021/jm030862l C-C chemokine receptor type 2 15
17715128 10.1074/jbc.m705302200 C-C chemokine receptor type 2 11
19949052 10.1128/aac.00891-09 Human immunodeficiency virus 1 5
28463783 10.1016/j.ejmech.2017.04.046 C-C chemokine receptor type 5 3
21658961 10.1016/j.bmc.2011.05.022 Human immunodeficiency virus 1 3
25766632 10.1016/j.bmc.2015.02.019 C-C chemokine receptor type 2 3
28463783 10.1016/j.ejmech.2017.04.046 C-C chemokine receptor type 2 3
17954689 10.1128/aac.00737-07 Envelope glycoprotein gp160 2
21256008 10.1016/j.bmcl.2010.12.109 Human immunodeficiency virus 1 2
28165741 10.1021/acs.jmedchem.6b01309 C-C chemokine receptor type 2 2
21820898 10.1016/j.bmcl.2011.07.058 C-C chemokine receptor type 5 2
28165741 10.1021/acs.jmedchem.6b01309 C-X-C chemokine receptor type 3 2
31742400 10.1021/acs.jmedchem.9b00742 C-C chemokine receptor type 5 2
16539392 10.1021/jm0509703 C-C chemokine receptor type 5 2
17116673 10.1128/aac.01079-06 Human immunodeficiency virus 1 2
11931608 10.1021/jm010468s C-C chemokine receptor type 2 1
10969972 10.1016/s0960-894x(00)00347-4 C-C chemokine receptor type 2 1
10821717 10.1021/jm9906264 Unchecked 1
10821717 10.1021/jm9906264 C-C chemokine receptor type 4 1
10821717 10.1021/jm9906264 C-C chemokine receptor type 2 1

Data from ChEMBL 36 via Core Engine