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Compound Detail

CHEMBL464538

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C=CC[N+](C)(C)c1ccc(CCC(=O)CCc2ccc([N+](C)(C)CC=C)cc2)cc1.[Br-].[Br-]
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL464538
Phase Preclinical
Structure Type MOL
InChI Key WKDURMTZOWGWTD-UHFFFAOYSA-L
Parent Compound CHEMBL140020
Active Moiety CHEMBL140020
5
Targets
38
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

406.6
MW (Da)
5.33
ALogP
1
HBA
0
HBD
17.1
PSA (Ų)
0.34
QED
1
Ro5 Violations
12
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C27H38Br2N2O
MW 566.42
Aromatic Rings 2
Heavy Atoms 30
NP-Likeness 0.52

Activity Summary

IC50 28 meas. best 10.1
Ki 10 meas. best 8.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
 IC50 10.1 7.996 0.1 15
Acetylcholinesterase
CHEMBL220
 Ki 8.0 7.5 10.0 8
Acetylcholinesterase
CHEMBL4078
 IC50 8.0 7.6 10.0 2
Acetylcholinesterase
CHEMBL220
 IC50 7.75 7.566 18.0 5
Cholinesterase
CHEMBL1914
 Ki 7.3 7.3 50.0 1
Acetylcholinesterase
CHEMBL4768
 Ki 7.24 7.24 57.1 1
Cholinesterase
CHEMBL1914
 IC50 4.32 4.32 48000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum IC50 = 0.08 nM 10.1 Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR gr... 19734910
Plasmodium falciparum IC50 = 0.09 nM 10.05 Antiplasmodial activity against Plasmodium falciparum 3D7 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 0.22 nM 9.66 Antiplasmodial activity against Plasmodium falciparum GB4 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 0.28 nM 9.55 Antiplasmodial activity against Plasmodium falciparum D10 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 0.28 nM 9.55 Antiplasmodial activity against Plasmodium falciparum HB3 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 0.47 nM 9.33 Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 1.86 nM 8.73 Antiplasmodial activity against Plasmodium falciparum Dd2 after 72 hrs by SYBR g... 19734910
Acetylcholinesterase Ki = 10.0 nM 8.0 Dissociation constant for enzyme-inhibitor complex of human recombinant AChE by ... 21236521
Acetylcholinesterase Ki = 10.0 nM 8.0 Inhibition of human recombinant AChE assessed as dissociation constant for enzym... 21144749
Acetylcholinesterase Ki = 10.0 nM 8.0 Inhibition of human AChE 18479118
Acetylcholinesterase Ki = 10.0 nM 8.0 Inhibition of human erythrocytes recombinant AChE assessed as dissociation const... 21397501
Acetylcholinesterase IC50 = 10.0 nM 8.0 Inhibition of electric eel AChE by Ellman's method 9287420
Acetylcholinesterase IC50 = 18.0 nM 7.75 Anticholinesterase activity against human erythrocyte AChE 16570913
Acetylcholinesterase IC50 = 30.0 nM 7.52 Inhibition of human erythrocyte recombinant AChE by modified Ellman's method 21397501
Acetylcholinesterase IC50 = 30.0 nM 7.52 Inhibition of human recombinant AChE after 5 mins by Ellman's method 24220173
Acetylcholinesterase IC50 = 30.0 nM 7.52 Inhibition of human recombinant AChE by Lineweaver-Burk plot analysis 21236521
Acetylcholinesterase IC50 = 30.0 nM 7.52 Inhibition of human recombinant AChE 21144749
Acetylcholinesterase Ki = 50.0 nM 7.3 Non competitive inhibition of human recombinant AChE using ATChCl as substrate b... 24220173
Acetylcholinesterase Ki = 50.0 nM 7.3 Inhibition of human erythrocytes recombinant AChE assessed as dissociation const... 21397501
Acetylcholinesterase Ki = 50.0 nM 7.3 Dissociation constant for enzyme-inhibitor-substrate complex of human recombinan... 21236521

Literature References

PubMed DOI Target Context # Activities
19734910 10.1038/nchembio.215 Plasmodium falciparum 14
24738476 10.1021/jm5000613 Acetylcholinesterase 4
24220173 10.1016/j.bmcl.2013.10.043 Acetylcholinesterase 3
21397501 10.1016/j.bmcl.2011.02.047 Acetylcholinesterase 3
21236521 10.1016/j.ejmech.2010.12.011 Acetylcholinesterase 3
19856923 10.1021/jm900628z Acetylcholinesterase 3
18479118 10.1021/jm701253t Acetylcholinesterase 2
21144749 10.1016/j.bmcl.2010.11.051 Acetylcholinesterase 2
21144749 10.1016/j.bmcl.2010.11.051 Cholinesterase 2
18817366 10.1021/jm800564y Acetylcholinesterase 1
18817366 10.1021/jm800564y Unchecked 1
18817366 10.1021/jm800564y Cholinesterase 1
20575555 10.1021/jm901902w Acetylcholinesterase 1
17417631 10.1038/nchembio873 Unchecked 1
21144749 10.1016/j.bmcl.2010.11.051 Cholinesterases; ACHE & BCHE 1
9287420 10.1021/np9701236 Acetylcholinesterase 1
24738476 10.1021/jm5000613 Unchecked 1
21236521 10.1016/j.ejmech.2010.12.011 Cholinesterases; ACHE & BCHE 1
16570913 10.1021/jm050578p Cholinesterases; ACHE & BCHE 1
16570913 10.1021/jm050578p Cholinesterase 1

Data from ChEMBL 36 via Core Engine