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Compound Detail

CHEMBL33051

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NC(=O)c1cc[n+](COC[n+]2ccccc2/C=N/O)cc1.[Cl-].[Cl-]
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL33051
Phase Preclinical
Structure Type MOL
InChI Key QELSIJXWEROXOE-UHFFFAOYSA-N
Parent Compound CHEMBL385181
Active Moiety CHEMBL385181
2
Targets
21
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

288.3
MW (Da)
-0.20
ALogP
4
HBA
2
HBD
92.7
PSA (Ų)
0.33
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C14H16Cl2N4O3
MW 359.21
Aromatic Rings 2
Heavy Atoms 21
NP-Likeness -0.48

Activity Summary

IC50 11 meas. best 4.27
Kd 7 meas. best 4.62
Ki 3 meas. best 4.6

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Acetylcholinesterase
CHEMBL3199
 Kd 4.62 4.62 24000.0 1
Acetylcholinesterase
CHEMBL220
 Ki 4.6 4.6 25000.0 1
Acetylcholinesterase
CHEMBL220
 Kd 4.3 4.17 50000.0 3
Acetylcholinesterase
CHEMBL220
 IC50 4.27 4.19 54000.0 4

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Acetylcholinesterase Kd = 24000.0 nM 4.62 Binding affinity to AChE in rat brain homogenate 21438612
Acetylcholinesterase Ki = 25000.0 nM 4.6 Reversible inhibition of recombinant human recombinant AChE using acetylthiochol... 30383374
Acetylcholinesterase Kd = 50000.0 nM 4.3 Binding affinity to VX-human AChE complex 23148598
Acetylcholinesterase IC50 = 54000.0 nM 4.27 Inhibition of human recombinant AChE by spectrophotometry based Ellman's assay 30125110
Acetylcholinesterase IC50 = 55000.0 nM 4.26 Inhibition of recombinant His-TEV-tagged human AChE expressed in CHO-K1 cells us... 35255209
Acetylcholinesterase IC50 = 66000.0 nM 4.18 Inhibition of human AChE 23984975
Acetylcholinesterase Kd = 70000.0 nM 4.16 Reactivation of VX-inhibited human recombinant AChE assessed as dissociation con... 30125110
Acetylcholinesterase IC50 = 89000.0 nM 4.05 Concentration required to inhibit 50% of acetylcholinesterase (AChE) in human er... 2913310
Acetylcholinesterase Kd = 90000.0 nM 4.05 Reactivation of NIMP-inhibited human recombinant AChE assessed as dissociation c... 30125110

Literature References

PubMed DOI Target Context # Activities
30383374 10.1021/acs.jmedchem.8b01398 Acetylcholinesterase 22
35526478 10.1016/j.ejmech.2022.114377 Cholinesterase 21
35526478 10.1016/j.ejmech.2022.114377 Acetylcholinesterase 19
30125110 10.1021/acs.jmedchem.8b00592 Acetylcholinesterase 13
35255209 10.1021/acs.jmedchem.1c01748 Acetylcholinesterase 13
2913310 10.1021/jm00122a034 Acetylcholinesterase 13
21215642 10.1016/j.bmc.2010.12.021 Acetylcholinesterase 9
23148598 10.1021/jm3015519 Acetylcholinesterase 9
3746817 10.1021/jm00159a021 Acetylcholinesterase 5
24571195 10.1021/jm401650z Cholinesterase 5
18676153 10.1016/j.bmc.2008.07.036 Acetylcholinesterase 4
2913310 10.1021/jm00122a034 Mus musculus 4
17383875 10.1016/j.bmcl.2007.03.025 Acetylcholinesterase 4
6492073 10.1021/jm00377a010 ADMET 4
14505667 10.1016/s0960-894x(03)00751-0 Acetylcholinesterase 4
2913311 10.1021/jm00122a035 Mus musculus 4
2016711 10.1021/jm00108a019 Mus musculus 4
16934462 10.1016/j.bmcl.2006.08.011 Acetylcholinesterase 4
17869525 10.1016/j.bmc.2007.08.056 Acetylcholinesterase 4
17924614 10.1021/jm070653r Acetylcholinesterase 4

Data from ChEMBL 36 via Core Engine