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Compound Detail

CHEMBL424707

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c1ccc2c(NCCCCCCCCCNc3c4c(nc5ccccc35)CCCC4)c3c(nc2c1)CCCC3
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL424707
Phase Preclinical
Structure Type MOL
InChI Key XCTLFKXGBMSLLN-UHFFFAOYSA-N
9
Targets
14
Activities
2
Assay Types
0
PK Parameters
14
Publications
0
Known Names

Molecular Properties

520.8
MW (Da)
8.80
ALogP
4
HBA
2
HBD
49.8
PSA (Ų)
0.18
QED
2
Ro5 Violations
12
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C35H44N4
MW 520.77
Aromatic Rings 4
Heavy Atoms 39
NP-Likeness -0.40

Activity Summary

IC50 12 meas. best 9.11
Ki 2 meas. best 6.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Acetylcholinesterase
CHEMBL3199
 IC50 9.11 8.31 0.8 2
Plasmodium falciparum
CHEMBL364
 IC50 7.3 7.06 50.0 2
Trypanosoma brucei brucei
CHEMBL612851
 IC50 6.89 6.845 130.0 2
Butyrylcholinesterase
CHEMBL3403
 IC50 6.81 6.765 155.0 2
Trypanothione reductase
CHEMBL5131
 Ki 6.4 6.4 400.0 1
Unchecked
CHEMBL612545
 Ki 6.4 6.4 400.0 1
J774.1
CHEMBL4296442
 IC50 5.75 5.75 1800.0 1
ADMET
CHEMBL612558
 IC50 5.75 5.75 1800.0 1
Unchecked
CHEMBL612545
 IC50 4.94 4.94 11500.0 1
Rhodesain
CHEMBL4188
 IC50 4.71 4.71 19400.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Acetylcholinesterase IC50 = 0.77 nM 9.11 Inhibition of rat brain Acetylcholinesterase using acetylthiocholine as substrat... 30744931
Acetylcholinesterase IC50 = 31.0 nM 7.51 Inhibition of rat brain AChE 16942022
Plasmodium falciparum IC50 = 50.0 nM 7.3 Antimalarial activity against chloroquine-sensitive ring-stage Plasmodium falcip... 27316542
Trypanosoma brucei brucei IC50 = 130.0 nM 6.89 Antitrypanosomal activity against Trypanosoma brucei brucei TC221 after 48 hrs b... 28698054
Plasmodium falciparum IC50 = 150.0 nM 6.82 Antimalarial activity against chloroquine-resistant Plasmodium falciparum Dd2 as... 27316542
Butyrylcholinesterase IC50 = 155.0 nM 6.81 Inhibition of rat serum BuChE 16942022
Trypanosoma brucei brucei IC50 = 160.0 nM 6.8 Antitrypanosomal activity against Trypanosoma brucei brucei TC221 after 72 hrs b... 28698054
Butyrylcholinesterase IC50 = 190.0 nM 6.72 Inhibition of rat serum butyrylcholinesterase using butyrylthiocholine as substr... 30744931
Trypanothione reductase Ki = 400.0 nM 6.4 Competitive inhibition of Trypanosoma cruzi trypanothione reductase using varyin... 28698054
Unchecked Ki = 400.0 nM 6.4 Inhibition of Trypanosoma brucei trypanothione reductase using varying levels of... 28698054
ADMET IC50 = 1800.0 nM 5.75 Cytotoxicity against mouse J774.1 cells after 24 hrs by AlamarBlue based cytotox... 27316542
J774.1 IC50 = 1800.0 nM 5.75 Cytotoxicity against mouse J774.1 cells after 24 hrs by alamar blue assay 28698054
Unchecked IC50 = 11500.0 nM 4.94 Reversible inhibition of recombinant Plasmodium falciparum falcipain 2 assessed ... 27316542
Rhodesain IC50 = 19400.0 nM 4.71 Inhibition of Trypanosoma brucei rhodesiense rhodesain using Cbz-Phe-Arg-AMC as ... 28698054

Literature References

PubMed DOI Target Context # Activities
28698054 10.1016/j.bmc.2017.06.051 Trypanothione reductase 6
27316542 10.1016/j.bmc.2016.06.003 Unchecked 4
28698054 10.1016/j.bmc.2017.06.051 Unchecked 4
28698054 10.1016/j.bmc.2017.06.051 Rhodesain 3
27316542 10.1016/j.bmc.2016.06.003 Plasmodium falciparum 2
28698054 10.1016/j.bmc.2017.06.051 Trypanosoma brucei brucei 2
16942022 10.1021/jm060164b Acetylcholinesterase and butyrylcholinesterase (AChE and BChE) 1
16942022 10.1021/jm060164b Butyrylcholinesterase 1
16942022 10.1021/jm060164b Acetylcholinesterase 1
27316542 10.1016/j.bmc.2016.06.003 ADMET 1
28698054 10.1016/j.bmc.2017.06.051 J774.1 1
28698054 10.1016/j.bmc.2017.06.051 Leishmania infantum 1
30744931 10.1016/j.bmc.2019.01.025 Acetylcholinesterase 1
30744931 10.1016/j.bmc.2019.01.025 Butyrylcholinesterase 1

Data from ChEMBL 36 via Core Engine