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Compound Detail

CHEMBL432713

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O=C(/C=C/c1ccc(Cl)c(Cl)c1)NCCCCCN1CCC(c2c[nH]c3ccc(O)cc23)CC1

Basic Information

ChEMBL ID CHEMBL432713
Phase Preclinical
Structure Type MOL
InChI Key QBRLVMQBZIFWTB-WEVVVXLNSA-N
13
Targets
33
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

500.5
MW (Da)
6.36
ALogP
3
HBA
3
HBD
68.4
PSA (Ų)
0.24
QED
2
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C27H31Cl2N3O2
MW 500.47
Aromatic Rings 3
Heavy Atoms 34
NP-Likeness -0.57

Activity Summary

Ki 32 meas. best 8.5
IC50 1 meas. best 7.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 1F
CHEMBL1805
Ki 8.5 8.5 3.2 1
5-hydroxytryptamine receptor 1E
CHEMBL2182
Ki 8.2 8.2 6.3 1
D(3) dopamine receptor
CHEMBL234
Ki 8.1 8.1 7.9 1
5-hydroxytryptamine receptor 1B
CHEMBL1898
Ki 7.9 7.9 12.6 1
D(2) dopamine receptor
CHEMBL217
Ki 7.8 7.8 15.8 1
C-C chemokine receptor type 2
CHEMBL4015
Ki 7.78 6.827 16.6 20
5-hydroxytryptamine receptor 2A
CHEMBL224
Ki 7.7 7.7 19.9 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
Ki 7.6 7.6 25.1 1
5-hydroxytryptamine receptor 7
CHEMBL3155
Ki 7.2 7.2 63.1 1
5-hydroxytryptamine receptor 2C
CHEMBL225
Ki 7.1 7.1 79.4 1
5-hydroxytryptamine receptor 6
CHEMBL3371
Ki 7.1 7.1 79.4 1
5-hydroxytryptamine receptor 1A
CHEMBL214
Ki 7.0 7.0 100.0 1
C-C chemokine receptor type 2
CHEMBL4015
IC50 7.0 7.0 100.0 1
C-C chemokine receptor type 5
CHEMBL274
Ki 5.37 5.37 4260.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 1F Ki = 3.162 nM 8.5 Binding affinity for 5-hydroxytryptamine 1F receptor was determined 11514164
5-hydroxytryptamine receptor 1E Ki = 6.31 nM 8.2 Binding affinity for 5-hydroxytryptamine 1E receptor was determined 11514164
D(3) dopamine receptor Ki = 7.943 nM 8.1 Binding affinity for Dopamine receptor D3 was determined 11514164
5-hydroxytryptamine receptor 1B Ki = 12.59 nM 7.9 Binding affinity for 5-hydroxytryptamine 1B receptor was determined 11514164
D(2) dopamine receptor Ki = 15.85 nM 7.8 Binding affinity for Dopamine receptor D2 was determined 11514164
C-C chemokine receptor type 2 Ki = 16.6 nM 7.78 Binding affinity of compound (10 uM) towards Y49F receptor variant (mutant CCR2 ... 12954060
5-hydroxytryptamine receptor 2A Ki = 19.95 nM 7.7 Binding affinity for 5-hydroxytryptamine 2A receptor was determined 11514164
5-hydroxytryptamine receptor 2B Ki = 25.12 nM 7.6 Binding affinity for 5-hydroxytryptamine 2B receptor was determined 11514164
C-C chemokine receptor type 2 Ki = 50.12 nM 7.3 Antagonist activity at human CCR2 receptor 18226895
C-C chemokine receptor type 2 Ki = 50.0 nM 7.3 Antagonist activity at human CCR2 receptor 18226895
C-C chemokine receptor type 2 Ki = 50.0 nM 7.3 Displacement of [125I]MCP1 from human CCR2 expressed in CHO cells 16698264
C-C chemokine receptor type 2 Ki = 50.0 nM 7.3 Antagonist activity against C-C chemokine receptor type 2 10969972
C-C chemokine receptor type 2 Ki = 50.12 nM 7.3 Binding displacement of [125I]MCP-1 (0.14 nM) was measured on CHO cell membranes... 12954060
C-C chemokine receptor type 2 Ki = 50.0 nM 7.3 Inhibition of [125I]MCP-1 binding to the cloned C-C chemokine receptor type 2B e... 11514164
C-C chemokine receptor type 2 Ki = 50.12 nM 7.3 Inhibition of [125I]MCP-1 binding to the cloned C-C chemokine receptor type 2B e... 11514164
C-C chemokine receptor type 2 Ki = 50.0 nM 7.3 Binding affinity at C-C chemokine receptor type 2 was determined 12954060
5-hydroxytryptamine receptor 7 Ki = 63.1 nM 7.2 Binding affinity for 5-hydroxytryptamine 7 receptor was determined 11514164
5-hydroxytryptamine receptor 2C Ki = 79.43 nM 7.1 Binding affinity for 5-hydroxytryptamine 2C receptor was determined 11514164
5-hydroxytryptamine receptor 6 Ki = 79.43 nM 7.1 Binding affinity for 5-hydroxytryptamine 6 receptor was determined 11514164
C-C chemokine receptor type 2 Ki = 100.0 nM 7.0 Binding affinity to CCR2 (unknown origin) assessed as inhibition constant 28165741

Literature References

PubMed DOI Target Context # Activities
12954060 10.1021/jm030862l C-C chemokine receptor type 2 15
20485427 10.1038/nature09107 Plasmodium falciparum 4
28165741 10.1021/acs.jmedchem.6b01309 C-C chemokine receptor type 2 2
18226895 10.1016/j.bmcl.2007.12.072 C-C chemokine receptor type 2 2
10969972 10.1016/s0960-894x(00)00347-4 Homo sapiens 2
11514164 10.1016/s0960-894x(01)00397-3 C-C chemokine receptor type 2 2
11514164 10.1016/s0960-894x(01)00397-3 D(2) dopamine receptor 1
16698264 10.1016/j.bmcl.2006.04.045 C-C chemokine receptor type 2 1
16698264 10.1016/j.bmcl.2006.04.045 Monocyte 1
10969972 10.1016/s0960-894x(00)00347-4 C-C chemokine receptor type 5 1
10969972 10.1016/s0960-894x(00)00347-4 C-C chemokine receptor type 2 1
11514164 10.1016/s0960-894x(01)00397-3 D(3) dopamine receptor 1
11514164 10.1016/s0960-894x(01)00397-3 5-hydroxytryptamine receptor 7 1
11514164 10.1016/s0960-894x(01)00397-3 5-hydroxytryptamine receptor 6 1
11514164 10.1016/s0960-894x(01)00397-3 5-hydroxytryptamine receptor 2C 1
11514164 10.1016/s0960-894x(01)00397-3 5-hydroxytryptamine receptor 2B 1
11514164 10.1016/s0960-894x(01)00397-3 5-hydroxytryptamine receptor 2A 1
11514164 10.1016/s0960-894x(01)00397-3 5-hydroxytryptamine receptor 1F 1
11514164 10.1016/s0960-894x(01)00397-3 5-hydroxytryptamine receptor 1E 1
11514164 10.1016/s0960-894x(01)00397-3 5-hydroxytryptamine receptor 1B 1

Data from ChEMBL 36 via Core Engine