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Compound Detail

CHEMBL185951

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CN1CCN(C(=O)c2nc3ccc(Cl)cc3[nH]2)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL185951
Phase Preclinical
Structure Type MOL
InChI Key MOIWSUQWIOVGRH-UHFFFAOYSA-N
2
Targets
17
Activities
4
Assay Types
12
PK Parameters
18
Publications
0
Known Names

Molecular Properties

278.7
MW (Da)
1.60
ALogP
3
HBA
1
HBD
52.2
PSA (Ų)
0.86
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C13H15ClN4O
MW 278.74
Aromatic Rings 2
Heavy Atoms 19
NP-Likeness -1.74

Activity Summary

Ki 13 meas. best 7.7
IC50 2 meas. best 6.86
EC50 1 meas. best 5.5
Kd 1 meas. best 7.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histamine H4 receptor
CHEMBL3759
 Kd 7.7 7.7 19.9 1
Histamine H4 receptor
CHEMBL3759
 Ki 7.7 7.455 20.0 10
Histamine H4 receptor
CHEMBL3759
 IC50 6.86 6.57 138.0 2
Histamine H3 receptor
CHEMBL264
 EC50 5.5 5.5 3162.3 1
Histamine H3 receptor
CHEMBL264
 Ki 5.4 4.9833 3981.1 3

Pharmacokinetic Data

Parameter Value Units Species
AUC 2.1 uM.h/L Rattus norvegicus
CL 700000.0 mL.min-1.g-1 Rattus norvegicus
Cmax 1800.0 nM Rattus norvegicus
F 27.0 % Rattus norvegicus
T1/2 1.667 hr Homo sapiens
T1/2 1.667 hr Homo sapiens
T1/2 0.2 hr Rattus norvegicus
T1/2 1.467 hr Rattus norvegicus
T1/2 1.0 hr Rattus norvegicus
T1/2 0.4267 hr Homo sapiens
T1/2 0.7 hr Rattus norvegicus
Vd 23.0 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histamine H4 receptor Kd = 19.95 nM 7.7 Antagonistic activity at human histamine H4 receptor in SK-N-MC cells by inhibit... 16366610
Histamine H4 receptor Ki = 20.0 nM 7.7 Displacement of [3H]histamine from human recombinant histamine H4 receptor expre... 24495018
Histamine H4 receptor Ki = 26.0 nM 7.58 Displacement of [3H]histamine from recombinant human histamine H4 receptor in SK... 16366610
Histamine H4 receptor Ki = 26.0 nM 7.58 Displacement of [3H]histamine from human histamine H4 receptor 21458260
Histamine H4 receptor Ki = 26.0 nM 7.58 Displacement of [3H]histamine from human H4 receptor expressed in HEK cell membr... 22153663
Histamine H4 receptor Ki = 27.0 nM 7.57 Binding affinity to histamine H4 receptor (unknown origin) assessed as inhibitio... 36731273
Histamine H4 receptor Ki = 39.6 nM 7.4 Antagonist activity at human histamine H4 receptor by functional assay 21955944
Histamine H4 receptor Ki = 39.6 nM 7.4 Antagonist activity at human histamine H4 receptor expressed in HEK293 cells ass... 22189138
Histamine H4 receptor Ki = 47.7 nM 7.32 Displacement of [3H]histamine from human recombinant histamine H4 receptor expre... 22189138
Histamine H4 receptor Ki = 47.7 nM 7.32 Displacement of [3H]histamine from human histamine H4 receptor expressed in CHO ... 21955944
Histamine H4 receptor Ki = 79.43 nM 7.1 Binding affinity towards human histamine H4 receptor was determined by [3H]Na-me... 15454206
Histamine H4 receptor IC50 = 138.0 nM 6.86 Inhibition of mouse bone-marrow mast cell chemotaxis mediated by histamine H4 re... 16366610
Histamine H4 receptor IC50 = 530.0 nM 6.28 Inhibition of human eosinophil chemotaxis mediated by histamine H4 receptor 16366610
Histamine H3 receptor EC50 = 3162.28 nM 5.5 Effective concentration required against human histamine H3 receptor was determi... 15454206
Histamine H3 receptor Ki = 3981.07 nM 5.4 Binding affinity towards human histamine H3 receptor was determined by [3H]Na-me... 15454206
Histamine H3 receptor Ki = 14053.0 nM 4.85 Binding affinity to histamine H3 receptor 16366610
Histamine H3 receptor Ki = 20000.0 nM 4.7 Binding affinity to human histamine H3 receptor 22189138

Literature References

PubMed DOI Target Context # Activities
16366610 10.1021/jm0502081 Rattus norvegicus 5
16366610 10.1021/jm0502081 Histamine H4 receptor 4
15454206 10.1016/j.bmcl.2004.08.035 Histamine H3 receptor 3
22189138 10.1016/j.bmcl.2011.11.098 Rattus norvegicus 3
22153663 10.1016/j.bmcl.2011.10.104 Histamine H4 receptor 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
22189138 10.1016/j.bmcl.2011.11.098 Liver microsomes 2
22189138 10.1016/j.bmcl.2011.11.098 Histamine H4 receptor 2
21955944 10.1016/j.bmcl.2011.07.114 Histamine H4 receptor 2
16366610 10.1021/jm0502081 Liver microsomes 2
15454206 10.1016/j.bmcl.2004.08.035 Histamine H4 receptor 1
21458260 10.1016/j.bmcl.2011.03.017 Histamine H4 receptor 1
22189138 10.1016/j.bmcl.2011.11.098 Histamine H3 receptor 1
16366610 10.1021/jm0502081 Histamine H3 receptor 1
16366610 10.1021/jm0502081 Homo sapiens 1
24495018 10.1021/jm401727m Histamine H4 receptor 1
33333448 10.1016/j.bmc.2020.115924 Histamine H4 receptor 1
36731273 10.1016/j.ejmech.2023.115151 Histamine H4 receptor 1

Data from ChEMBL 36 via Core Engine