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Compound Detail

CHEMBL351231

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C[C@@H]1CCCN1CCc1cc2cc(-c3ccc(C#N)cc3)ccc2o1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL351231
Phase Preclinical
Structure Type MOL
InChI Key KFHYZKCRXNRKRC-MRXNPFEDSA-N
3
Targets
42
Activities
4
Assay Types
30
PK Parameters
20
Publications
0
Known Names

Molecular Properties

330.4
MW (Da)
5.00
ALogP
3
HBA
0
HBD
40.2
PSA (Ų)
0.68
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C22H22N2O
MW 330.43
Aromatic Rings 3
Heavy Atoms 25
NP-Likeness -0.80

Activity Summary

Ki 35 meas. best 9.4
EC50 4 meas. best 8.89
IC50 2 meas. best 9.2
Kd 1 meas. best 7.89

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histamine H3 receptor
CHEMBL264
 Ki 9.4 9.1011 0.4 19
Histamine H3 receptor
CHEMBL4124
 Ki 9.35 8.6273 0.5 15
Histamine H3 receptor
CHEMBL264
 IC50 9.2 9.2 0.6 1
Histamine H3 receptor
CHEMBL264
 EC50 8.89 8.89 1.3 2
Histamine H3 receptor
CHEMBL264
 Kd 7.89 7.89 12.9 1
Histamine H3 receptor
CHEMBL4124
 EC50 7.76 7.76 17.4 2
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 Ki 6.4 6.4 400.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 5.8 5.8 1600.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 666.8 ng.hr.mL-1 Rattus norvegicus
AUC 426.2 ng.hr.mL-1 Rattus norvegicus
AUC 673.0 ng.hr.mL-1 Rattus norvegicus
AUC 349.0 ng.hr.mL-1 Rattus norvegicus
CL 25.0 mL.min-1.kg-1 Rattus norvegicus
CL 13.0 mL.min-1.kg-1 Canis lupus familiaris
CL 5.0 mL.min-1.kg-1 Cercopithecidae
CL 24.17 mL.min-1.kg-1 Rattus norvegicus
CL 25.0 mL.min-1.kg-1 Rattus norvegicus
CL 25.0 mL.min-1.kg-1 Rattus norvegicus
CL 39.0 mL.min-1.kg-1 Rattus norvegicus
Cmax 119.84 nM Rattus norvegicus
Cmax 87.76 nM Rattus norvegicus
F 53.0 % Rattus norvegicus
F 53.0 % Canis lupus familiaris
F 53.0 % Cercopithecidae
F 61.8 % Rattus norvegicus
F 53.0 % Rattus norvegicus
F 53.0 % Rattus norvegicus
F 18.0 % Rattus norvegicus
F 52.0 % Rattus norvegicus
F 74.0 % Canis lupus familiaris
F 89.0 % Macaca mulatta
T1/2 5.3 hr Rattus norvegicus
T1/2 8.3 hr Canis lupus familiaris
T1/2 29.2 hr Cercopithecidae
T1/2 5.7 hr Rattus norvegicus
T1/2 6.7 hr Rattus norvegicus
T1/2 5.3 hr Rattus norvegicus
T1/2 5.3 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histamine H3 receptor Ki = 0.4 nM 9.4 Binding affinity to histamine H3 receptor 19456097
Histamine H3 receptor Ki = 0.45 nM 9.35 Binding potency was determined by displacement of [3H]N-alpha-methyl histamine f... 14741270
Histamine H3 receptor Ki = 0.4467 nM 9.35 Displacement of [3H]N-alpha methyl histamine from human cloned histamine H3 rece... 19588934
Histamine H3 receptor Ki = 0.45 nM 9.35 Displacement of [3H]N-alpha-methylhistamine from human cloned histamine H3 recep... 17169555
Histamine H3 receptor Ki = 0.45 nM 9.35 Displacement of [3H]-N-alpha methyl histamine from human H3 receptor expressed i... 17918921
Histamine H3 receptor Ki = 0.4467 nM 9.35 Displacement of [3H]-N-alpha methyl histamine from human H3 receptor expressed i... 17918921
Histamine H3 receptor Ki = 0.45 nM 9.35 In vitro binding affinity for human histamine H3 receptor using [3H]N-alpha-meth... 16190774
Histamine H3 receptor Ki = 0.4467 nM 9.35 In vitro binding affinity was determined as displacement of [3H]N-R-methylhistam... 15634000
Histamine H3 receptor Ki = 0.45 nM 9.35 In vitro binding affinity was determined as displacement of [3H]N-R-methylhistam... 15634000
Histamine H3 receptor Ki = 0.4467 nM 9.35 Binding potency was determined by displacement of [3H]N-alpha-methyl histamine f... 14741270
Histamine H3 receptor Ki = 0.45 nM 9.35 Displacement of [3H]N-alpha-methylhistamine from human cloned histamine H3 recep... 20457525
Histamine H3 receptor Ki = 0.45 nM 9.35 Displacement of [3H]N-alpha-methylhistamine from human histamine H3 receptor exp... 19577344
Histamine H3 receptor Ki = 0.45 nM 9.35 Displacement of [125I]Iodoproxyfan from human recombinant histamine H3 receptor ... 21802950
Histamine H3 receptor Ki = 0.45 nM 9.35 Binding affinity to rat cortical histamine H3 receptor 21062081
Histamine H3 receptor Ki = 0.45 nM 9.35 Displacement of [3H]N-alpha methyl histamine from human cloned histamine H3 rece... 19588934
Histamine H3 receptor IC50 = 0.63 nM 9.2 Antagonist activity at human cloned histamine H3 receptor expressed in CHO-K1 ce... 18841880
Histamine H3 receptor Ki = 1.23 nM 8.91 In vitro binding affinity for rat histamine H3 receptor using [3H]N-alpha-methyl... 16190774
Histamine H3 receptor EC50 = 1.29 nM 8.89 Agonist activity at human histamine H3 receptor expressed in HEK239 cells assess... 17918921
Histamine H3 receptor EC50 = 1.288 nM 8.89 Agonist activity at human histamine H3 receptor expressed in HEK239 cells assess... 17918921
Histamine H3 receptor Ki = 1.35 nM 8.87 In vitro binding affinity was determined as displacement of [3H]N-R-methylhistam... 15634000

Literature References

PubMed DOI Target Context # Activities
17918921 10.1021/jm0705051 Histamine H3 receptor 14
15634000 10.1021/jm040118g ADMET 13
17169555 10.1016/j.bmcl.2006.11.073 Rattus norvegicus 8
16190774 10.1021/jm0504398 ADMET 7
15634000 10.1021/jm040118g Histamine H3 receptor 5
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
19588934 10.1021/jm900480x Histamine H3 receptor 4
17918921 10.1021/jm0705051 Rattus norvegicus 4
17918921 10.1021/jm0705051 Plasma 4
14741270 10.1016/j.bmcl.2003.11.032 Histamine H3 receptor 4
15634000 10.1021/jm040118g Rattus norvegicus 3
21634396 10.1021/jm200401v Rattus norvegicus 3
15634000 10.1021/jm040118g Cytochrome P450 2C9 2
15634000 10.1021/jm040118g Cytochrome P450 2C19 2
15634000 10.1021/jm040118g Cytochrome P450 2D6 2
15634000 10.1021/jm040118g Cytochrome P450 2A6 2
16190774 10.1021/jm0504398 Histamine H3 receptor 2
15634000 10.1021/jm040118g Cytochrome P450 1A2 2
17918921 10.1021/jm0705051 Nucleic Acid 2
17169555 10.1016/j.bmcl.2006.11.073 Histamine H3 receptor 2

Data from ChEMBL 36 via Core Engine