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Compound Detail

CHEMBL292314

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Nc1c2c(nc3cc(Cl)ccc13)CCCC2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL292314
Phase Preclinical
Structure Type MOL
InChI Key GQZMDBQRGRRPMS-UHFFFAOYSA-N

Known Names

6-Chlorotacrine HCl
14
Targets
48
Activities
3
Assay Types
0
PK Parameters
20
Publications
1
Known Names

Molecular Properties

232.7
MW (Da)
3.35
ALogP
2
HBA
1
HBD
38.9
PSA (Ų)
0.76
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C13H13ClN2
MW 232.71
Aromatic Rings 2
Heavy Atoms 16
NP-Likeness -0.97

Activity Summary

IC50 46 meas. best 8.74
EC50 1 meas. best 5.65
Ki 1 meas. best 4.1

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Acetylcholinesterase
CHEMBL220
 IC50 8.74 7.9768 1.8 19
Acetylcholinesterase
CHEMBL4078
 IC50 8.54 7.76 2.9 3
Butyrylcholinesterase
CHEMBL5077
 IC50 8.1 8.1 7.9 1
Cholinesterase
CHEMBL5763
 IC50 7.78 7.78 16.5 1
Acetylcholinesterase
CHEMBL3198
 IC50 7.7 7.7 19.8 1
Cholinesterase
CHEMBL1914
 IC50 6.94 6.0882 114.0 11
HT-22
CHEMBL614316
 EC50 5.65 5.65 2220.0 1
Muscarinic acetylcholine receptor M1
CHEMBL216
 IC50 5.21 5.21 6090.0 1
HepG2
CHEMBL395
 IC50 5.15 4.51 7130.0 4
Trypanosoma brucei brucei
CHEMBL612851
 IC50 4.9 4.835 12600.0 2
J774.1
CHEMBL4296442
 IC50 4.39 4.39 41000.0 1
Bifunctional epoxide hydrolase 2
CHEMBL2409
 IC50 4.31 4.31 49116.0 1
CHO-K1
CHEMBL614031
 IC50 4.15 4.15 71000.0 1
Trypanothione reductase
CHEMBL5131
 Ki 4.1 4.1 80000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Acetylcholinesterase IC50 = 1.8 nM 8.74 Inhibition of acetylcholinesterase (AChE) of human red blood cell (type XIII) by... -
Acetylcholinesterase IC50 = 1.82 nM 8.74 In vitro inhibitory activity against human erythrocyte acetylcholinesterase 15317459
Acetylcholinesterase IC50 = 2.87 nM 8.54 Inhibition of acetylcholinesterase (AChE) in electric eel (type V-S) by modified... -
Acetylcholinesterase IC50 = 5.9 nM 8.23 Inhibition of human recombinant AChE using acetylthiocholine iodide as substrate... 25016233
Acetylcholinesterase IC50 = 7.18 nM 8.14 Inhibition of human recombinant AChE after 5 mins by Ellman method 25259726
Butyrylcholinesterase IC50 = 7.93 nM 8.1 Inhibition of (BChE) Butyrylcholinesterase of horse serum -
Acetylcholinesterase IC50 = 9.0 nM 8.05 Inhibitory activity against human erythrocyte acetylcholinesterase 10821713
Acetylcholinesterase IC50 = 9.9 nM 8.0 Inhibition of AChE 20053484
Acetylcholinesterase IC50 = 10.0 nM 8.0 Inhibitory activity against human erythrocyte acetylcholinesterase 15317459
Acetylcholinesterase IC50 = 10.0 nM 8.0 Experimental pIC50 values for the inhibition of acetylcholinesterase 10821713
Acetylcholinesterase IC50 = 13.2 nM 7.88 Inhibition of human recombinant AChE using acetylthiocholine iodide as substrate... 22185619
Acetylcholinesterase IC50 = 13.6 nM 7.87 Inhibition of human erythrocyte AChE using acetylthiocholine chloride as substra... 25724825
Acetylcholinesterase IC50 = 14.5 nM 7.84 Inhibition of human recombinant AChE expressed in HEK293 cells using acetylthioc... 31351393
Acetylcholinesterase IC50 = 14.5 nM 7.84 Inhibition of recombinant human AChE expressed in HEK293 cells using acetylthioc... 32706255
Acetylcholinesterase IC50 = 14.5 nM 7.84 Inhibition of recombinant human AChE using acetylthiocholine iodide as substrate... 33829779
Acetylcholinesterase IC50 = 14.5 nM 7.84 Inhibition of recombinant human AChE using acetylthiocholine iodide as substrate... 35271276
Cholinesterase IC50 = 16.5 nM 7.78 Inhibition of equine serum BChE using acetylthiocholine chloride as substrate af... 25724825
Acetylcholinesterase IC50 = 17.6 nM 7.75 Inhibition of human erythrocyte AChE using acetylthiocholine iodide as substrate... 29533874
Acetylcholinesterase IC50 = 20.0 nM 7.7 Inhibition of human recombinant AChE using acetylthiocholine iodide as substrate... 30851693
Acetylcholinesterase IC50 = 19.8 nM 7.7 Inhibition of recombinant mouse AChE using acetylthiocholine iodide as substrate... 35271276

Literature References

PubMed DOI Target Context # Activities
32706255 10.1021/acs.jmedchem.0c00528 ADMET 4
28698054 10.1016/j.bmc.2017.06.051 Trypanosoma brucei brucei 2
25724825 10.1016/j.bmcl.2015.02.015 Acetylcholinesterase 2
10821713 10.1021/jm990971t Acetylcholinesterase 2
15317459 10.1021/jm049877p Acetylcholinesterase 2
32706255 10.1021/acs.jmedchem.0c00528 Cholinesterase 2
35271276 10.1021/acs.jmedchem.1c02150 Acetylcholinesterase 2
24602904 10.1016/j.bmcl.2014.02.006 HT-22 2
24602904 10.1016/j.bmcl.2014.02.006 NON-PROTEIN TARGET 2
- 10.1016/S0960-894X(00)80545-4 Acetylcholinesterase 2
32706255 10.1021/acs.jmedchem.0c00528 Beta-secretase 1 2
33984470 10.1016/j.bmcl.2021.128100 Nitric oxide synthase 1 2
35271276 10.1021/acs.jmedchem.1c02150 Bifunctional epoxide hydrolase 2 2
25016233 10.1016/j.ejmech.2014.07.021 Cholinesterase 1
25259726 10.1021/jm5010804 Acetylcholinesterase 1
25016233 10.1016/j.ejmech.2014.07.021 Microtubule-associated protein tau 1
25016233 10.1016/j.ejmech.2014.07.021 Acetylcholinesterase 1
35271276 10.1021/acs.jmedchem.1c02150 Cholinesterase 1
20053484 10.1016/j.ejmech.2009.12.038 Acetylcholinesterase 1
10639286 10.1021/jm990386s Trypanothione reductase 1

Data from ChEMBL 36 via Core Engine