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Compound Detail

CHEMBL85251

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CCCCN1CCC(CCC(=O)c2cc(Cl)c(N)cc2OC)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL85251
Phase Preclinical
Structure Type MOL
InChI Key JBHLYIVFFLNISJ-UHFFFAOYSA-N
4
Targets
9
Activities
3
Assay Types
1
PK Parameters
20
Publications
0
Known Names

Molecular Properties

352.9
MW (Da)
4.41
ALogP
4
HBA
1
HBD
55.6
PSA (Ų)
0.56
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C19H29ClN2O2
MW 352.91
Aromatic Rings 1
Heavy Atoms 24
NP-Likeness -0.78

Activity Summary

EC50 4 meas. best 8.7
Ki 3 meas. best 8.41
IC50 2 meas. best 6.39

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 4
CHEMBL1875
 EC50 8.7 8.6 2.0 3
5-hydroxytryptamine receptor 4
CHEMBL5017
 Ki 8.41 8.22 3.9 2
5-hydroxytryptamine receptor 4
CHEMBL4317
 EC50 8.06 8.06 8.7 1
5-hydroxytryptamine receptor 4
CHEMBL1875
 Ki 8.03 8.03 9.3 1
Acetylcholinesterase
CHEMBL220
 IC50 6.39 6.39 403.0 2

Pharmacokinetic Data

Parameter Value Units Species
Fu 0.008 - Sepia officinalis

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 4 EC50 = 2.0 nM 8.7 Agonist activity at human 5HT4e receptor expressed in CHO cells assessed as cAMP... 26363507
5-hydroxytryptamine receptor 4 EC50 = 2.0 nM 8.7 Partial agonist activity at human 5HT4E receptor expressed in CHO cells assessed... 34251799
5-hydroxytryptamine receptor 4 Ki = 3.9 nM 8.41 Displacement of [3H]-GR113808 from 5-HT4R in Dunkin-Hartley guinea pig straitum ... 30288221
5-hydroxytryptamine receptor 4 EC50 = 3.981 nM 8.4 Agonist activity against 5-HT4 receptor in rat esophageal muscularis mucosae -
5-hydroxytryptamine receptor 4 EC50 = 8.7 nM 8.06 Agonist activity at 5-HT4 receptor in Sprague-Dawley rat oesophagus assessed as ... 26363507
5-hydroxytryptamine receptor 4 Ki = 9.3 nM 8.03 Displacement of [3H]GR113808 from 5-HT4R in guinea pig brain membranes incubated... 25793650
5-hydroxytryptamine receptor 4 Ki = 9.33 nM 8.03 Displacement of [3H]-GR113808 from recombinant human 5-HT4BR expressed in membra... 30447434
Acetylcholinesterase IC50 = 403.0 nM 6.39 Inhibition of human erythrocyte AChE pre-incubated for 5 mins before acetylthioc... 25793650
Acetylcholinesterase IC50 = 403.0 nM 6.39 Inhibition of human AChE using acetylthiocholine iodide as substrate preincubate... 30243151

Literature References

PubMed DOI Target Context # Activities
34251799 10.1021/acs.jmedchem.1c00703 5-hydroxytryptamine receptor 4 4
26363507 10.1016/j.ejmech.2015.08.051 5-hydroxytryptamine receptor 4 4
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
25793650 10.1021/acs.jmedchem.5b00115 5-hydroxytryptamine receptor 4 2
34251799 10.1021/acs.jmedchem.1c00703 Rattus norvegicus 2
29763304 10.1021/acs.jmedchem.8b00457 Rattus norvegicus 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.1016/S0960-894X(01)80413-3 5-hydroxytryptamine receptor 4 2
30447434 10.1016/j.ejmech.2018.10.064 5-hydroxytryptamine receptor 4 2
30447434 10.1016/j.ejmech.2018.10.064 Acetylcholinesterase 2
30398862 10.1021/acs.jmedchem.8b01281 No relevant target 1
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 1
31419776 10.1016/j.ejmech.2019.111596 5-hydroxytryptamine receptor 4 1
30447434 10.1016/j.ejmech.2018.10.064 Sigma non-opioid intracellular receptor 1 1
- 10.21203/rs.3.rs-23951/v1 SARS-CoV-2 1
30398862 10.1021/acs.jmedchem.8b01281 Unchecked 1
30243151 10.1016/j.ejmech.2018.09.031 Acetylcholinesterase 1
30288221 10.1039/C8MD00233A 5-hydroxytryptamine receptor 4 1
25793650 10.1021/acs.jmedchem.5b00115 Mus musculus 1
25793650 10.1021/acs.jmedchem.5b00115 Acetylcholinesterase 1

Data from ChEMBL 36 via Core Engine