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Compound Detail

CHEMBL286136

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COc1cc(N)c(Cl)cc1C(=O)OCCN1CCCCC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL286136
Phase Preclinical
Structure Type MOL
InChI Key RVFIAQAAZUEPPE-UHFFFAOYSA-N
6
Targets
27
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

312.8
MW (Da)
2.57
ALogP
5
HBA
1
HBD
64.8
PSA (Ų)
0.67
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C15H21ClN2O3
MW 312.80
Aromatic Rings 1
Heavy Atoms 21
NP-Likeness -1.09

Activity Summary

Ki 18 meas. best 9.0
EC50 7 meas. best 8.6
IC50 2 meas. best 8.62

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 4
CHEMBL1875
 Ki 9.0 8.3118 1.0 11
5-hydroxytryptamine receptor 4
CHEMBL4317
 Ki 8.97 8.97 1.1 3
5-hydroxytryptamine receptor 4
CHEMBL4317
 IC50 8.62 8.62 2.4 1
5-hydroxytryptamine receptor 4
CHEMBL1875
 EC50 8.6 7.8633 2.5 3
Cavia porcellus
CHEMBL369
 EC50 8.4 8.4 4.0 1
5-hydroxytryptamine receptor 4
CHEMBL5017
 EC50 8.4 8.4 4.0 3
5-hydroxytryptamine receptor 4
CHEMBL5017
 Ki 8.22 8.22 6.0 2
Serotonin 3 (5-HT3) receptor
CHEMBL2094116
 Ki 6.14 6.125 730.0 2
Plasmodium falciparum
CHEMBL364
 IC50 4.9 4.9 12589.2 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 4 Ki = 1.0 nM 9.0 Binding affinity towards cloned human 5-hydroxytryptamine 4E receptor expressed ... 12801225
5-hydroxytryptamine receptor 4 Ki = 1.07 nM 8.97 Binding affinity against 5-hydroxytryptamine 4 receptor using [3H]GR-113808 as r... -
5-hydroxytryptamine receptor 4 Ki = 1.07 nM 8.97 Binding affinity towards 5-hydroxytryptamine 4 receptor was determined in rat st... 9046352
5-hydroxytryptamine receptor 4 Ki = 1.07 nM 8.97 Binding affinity at 5-hydroxytryptamine 4 receptor in rat striatal membranes by ... 9171886
5-hydroxytryptamine receptor 4 IC50 = 2.4 nM 8.62 5-hydroxytryptamine 4 receptor agonist activity was determined by the relaxation... -
5-hydroxytryptamine receptor 4 EC50 = 2.5 nM 8.6 Agonist activity at human 5HT4e receptor expressed in CHO cells assessed as cAMP... 26363507
5-hydroxytryptamine receptor 4 Ki = 3.5 nM 8.46 Binding affinity to YFP fused 5HT4 receptor expressed in CHO cells 17676726
5-hydroxytryptamine receptor 4 Ki = 3.69 nM 8.43 Binding affinity was determined against cloned 5-hydroxytryptamine 4D receptor i... 11020291
Cavia porcellus EC50 = 4.0 nM 8.4 Agonist activity was assessed as the concentration which gave a 50% increase in ... 9171886
5-hydroxytryptamine receptor 4 EC50 = 4.0 nM 8.4 Agonist activity at 5-HT4 receptor in guinea pig ileum assessed as increase in r... 26363507
5-hydroxytryptamine receptor 4 EC50 = 4.0 nM 8.4 5-hydroxytryptamine 4 receptor agonist activity as increased response to electri... -
5-hydroxytryptamine receptor 4 EC50 = 4.0 nM 8.4 5-hydroxytryptamine 4 receptor agonist activity, concentration which gave 50% in... 9046352
5-hydroxytryptamine receptor 4 Ki = 5.0 nM 8.3 Binding affinity for 5-HT4 receptor using [3H]GR-113808 16190749
5-hydroxytryptamine receptor 4 Ki = 5.0 nM 8.3 Displacement of [3H]GR-113808 from human 5HT4e receptor expressed in C6 cells 17676726
5-hydroxytryptamine receptor 4 Ki = 5.0 nM 8.3 Displacement of [3H]GR-113808 from human 5HT4 isoform E receptor expressed in ra... 19334715
5-hydroxytryptamine receptor 4 Ki = 5.6 nM 8.25 Binding affinity was determined against cloned 5-hydroxytryptamine 4E receptor i... 11020291
5-hydroxytryptamine receptor 4 Ki = 5.7 nM 8.24 Binding affinity to Rluc fused 5HT4 receptor expressed in CHO cells 17676726
5-hydroxytryptamine receptor 4 Ki = 6.0 nM 8.22 Displacement of [3H]GR113808 from serotonin 5-HT4 receptor in Dunkin-Hartley gui... 30108781
5-hydroxytryptamine receptor 4 Ki = 6.0 nM 8.22 Displacement of [3H]-GR113808 from 5-HT4R in Dunkin-Hartley guinea pig straitum ... 30288221
5-hydroxytryptamine receptor 4 Ki = 7.98 nM 8.1 Binding affinity was determined against cloned 5-hydroxytryptamine 4C receptor i... 11020291

Literature References

PubMed DOI Target Context # Activities
11020291 10.1021/jm0009538 5-hydroxytryptamine receptor 4 5
- 10.1016/S0960-894X(01)80508-4 5-hydroxytryptamine receptor 4 5
17676726 10.1021/jm070552t 5-hydroxytryptamine receptor 4 5
9046352 10.1021/jm960320m 5-hydroxytryptamine receptor 4 4
26363507 10.1016/j.ejmech.2015.08.051 5-hydroxytryptamine receptor 4 4
19334715 10.1021/jm801327q 5-hydroxytryptamine receptor 4 4
30108781 10.1039/C6MD00458J 5-hydroxytryptamine receptor 4 3
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
16190749 10.1021/jm050234z 5-hydroxytryptamine receptor 4 2
9171886 10.1021/jm960853v Cavia porcellus 2
- 10.1016/S0960-894X(01)80413-3 5-hydroxytryptamine receptor 4 2
12801225 10.1021/jm0307887 5-hydroxytryptamine receptor 4 1
- 10.1016/S0960-894X(01)80508-4 Serotonin 3 (5-HT3) receptor 1
19734910 10.1038/nchembio.215 Plasmodium falciparum 1
9046352 10.1021/jm960320m Serotonin 3 (5-HT3) receptor 1
30288221 10.1039/C8MD00233A 5-hydroxytryptamine receptor 4 1
- 10.21203/rs.3.rs-23951/v1 SARS-CoV-2 1
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 1
9171886 10.1021/jm960853v 5-hydroxytryptamine receptor 4 1

Data from ChEMBL 36 via Core Engine