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Compound Detail

CHEMBL75274

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c1ccc2c(NCCCCCCCCNc3c4c(nc5ccccc35)CCCC4)c3c(nc2c1)CCCC3
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL75274
Phase Preclinical
Structure Type MOL
InChI Key ZIDVXYDWJIVBSC-UHFFFAOYSA-N
12
Targets
17
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

506.7
MW (Da)
8.41
ALogP
4
HBA
2
HBD
49.8
PSA (Ų)
0.20
QED
2
Ro5 Violations
11
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C34H42N4
MW 506.74
Aromatic Rings 4
Heavy Atoms 38
NP-Likeness -0.41

Activity Summary

IC50 15 meas. best 9.18
Ki 2 meas. best 8.72

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Acetylcholinesterase
CHEMBL3199
 IC50 9.18 8.6967 0.7 3
Acetylcholinesterase
CHEMBL220
 IC50 8.8 8.8 1.6 1
Acetylcholinesterase
CHEMBL4768
 Ki 8.72 8.72 1.9 1
Butyrylcholinesterase
CHEMBL5077
 Ki 8.7 8.7 2.0 1
Cholinesterase
CHEMBL1914
 IC50 7.28 7.28 53.0 1
Butyrylcholinesterase
CHEMBL3403
 IC50 6.98 6.725 105.0 2
Plasmodium falciparum
CHEMBL364
 IC50 6.96 6.74 110.0 2
Trypanosoma brucei brucei
CHEMBL612851
 IC50 6.4 6.29 400.0 2
J774.1
CHEMBL4296442
 IC50 5.72 5.72 1900.0 1
ADMET
CHEMBL612558
 IC50 5.72 5.72 1900.0 1
Rhodesain
CHEMBL4188
 IC50 4.77 4.77 16900.0 1
Unchecked
CHEMBL612545
 IC50 4.77 4.77 17100.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Acetylcholinesterase IC50 = 0.66 nM 9.18 Inhibition of rat brain Acetylcholinesterase using acetylthiocholine as substrat... 30744931
Acetylcholinesterase IC50 = 1.6 nM 8.8 Concentration that causes 50% inhibition of Acetylcholinesterase (AChE) using ra... 12014965
Acetylcholinesterase IC50 = 1.6 nM 8.8 Inhibition of AChE 20053484
Acetylcholinesterase Ki = 1.9 nM 8.72 Dissociation constant for inhibition of fetal bovine serum Acetylcholinesterase 15771436
Butyrylcholinesterase Ki = 2.0 nM 8.7 Dissociation constant for inhibition of equine Butyrylcholinesterase (BuChE) 15771436
Acetylcholinesterase IC50 = 7.8 nM 8.11 Inhibition of rat brain AChE 16942022
Cholinesterase IC50 = 53.0 nM 7.28 Concentration that causes 50% inhibition of Butyrylcholinesterase (BChE) using h... 12014965
Butyrylcholinesterase IC50 = 105.0 nM 6.98 Inhibition of rat serum BuChE 16942022
Plasmodium falciparum IC50 = 110.0 nM 6.96 Antimalarial activity against chloroquine-sensitive ring-stage Plasmodium falcip... 27316542
Plasmodium falciparum IC50 = 300.0 nM 6.52 Antimalarial activity against chloroquine-resistant Plasmodium falciparum Dd2 as... 27316542
Butyrylcholinesterase IC50 = 340.0 nM 6.47 Inhibition of rat serum butyrylcholinesterase using butyrylthiocholine as substr... 30744931
Trypanosoma brucei brucei IC50 = 400.0 nM 6.4 Antitrypanosomal activity against Trypanosoma brucei brucei TC221 after 48 hrs b... 28698054
Trypanosoma brucei brucei IC50 = 660.0 nM 6.18 Antitrypanosomal activity against Trypanosoma brucei brucei TC221 after 72 hrs b... 28698054
ADMET IC50 = 1900.0 nM 5.72 Cytotoxicity against mouse J774.1 cells after 24 hrs by AlamarBlue based cytotox... 27316542
J774.1 IC50 = 1900.0 nM 5.72 Cytotoxicity against mouse J774.1 cells after 24 hrs by alamar blue assay 28698054
Unchecked IC50 = 17100.0 nM 4.77 Reversible inhibition of recombinant Plasmodium falciparum falcipain 2 assessed ... 27316542
Rhodesain IC50 = 16900.0 nM 4.77 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 Rhodesain 3
28698054 10.1016/j.bmc.2017.06.051 Trypanosoma brucei brucei 2
27842893 10.1016/j.ejmech.2016.10.064 ScN2a 2
27316542 10.1016/j.bmc.2016.06.003 Plasmodium falciparum 2
20053484 10.1016/j.ejmech.2009.12.038 Acetylcholinesterase 1
30744931 10.1016/j.bmc.2019.01.025 Butyrylcholinesterase 1
28698054 10.1016/j.bmc.2017.06.051 Unchecked 1
28698054 10.1016/j.bmc.2017.06.051 J774.1 1
27316542 10.1016/j.bmc.2016.06.003 ADMET 1
12014965 10.1021/jm010308g Acetylcholinesterase 1
17158047 10.1016/j.bmcl.2006.11.022 Acetylcholinesterase 1
16942022 10.1021/jm060164b Acetylcholinesterase 1
16942022 10.1021/jm060164b Acetylcholinesterase and butyrylcholinesterase (AChE and BChE) 1
16942022 10.1021/jm060164b Butyrylcholinesterase 1
15771436 10.1021/jm049510k Unchecked 1
15771436 10.1021/jm049510k Butyrylcholinesterase 1
15771436 10.1021/jm049510k Acetylcholinesterase 1
12014965 10.1021/jm010308g Unchecked 1

Data from ChEMBL 36 via Core Engine