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Compound Detail

CHEMBL252504

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CCN(CC)CCNc1c2ccccc2[n+](C)c2c1[nH]c1ccccc12.[Cl-]
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL252504
Phase Preclinical
Structure Type MOL
InChI Key ACFBMJRLCXKTKH-UHFFFAOYSA-N
Parent Compound CHEMBL1182602
Active Moiety CHEMBL1182602
7
Targets
12
Activities
1
Assay Types
2
PK Parameters
15
Publications
0
Known Names

Molecular Properties

347.5
MW (Da)
4.05
ALogP
2
HBA
2
HBD
34.9
PSA (Ų)
0.52
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 C22H27ClN4
MW 382.94
Aromatic Rings 4
Heavy Atoms 26
NP-Likeness -0.23

Activity Summary

IC50 12 meas. best 7.16

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
 IC50 7.16 7.074 70.0 5
HUVEC
CHEMBL613979
 IC50 6.17 6.17 674.0 1
Trypanosoma brucei brucei
CHEMBL612851
 IC50 6.05 6.05 900.0 1
Vero
CHEMBL391
 IC50 5.55 5.55 2800.0 2
Rhodesain
CHEMBL4188
 IC50 4.96 4.96 11000.0 1
Unchecked
CHEMBL612545
 IC50 4.64 4.64 23000.0 1
Cathepsin B-like cysteine protease
CHEMBL5832
 IC50 4.02 4.02 95000.0 1

Pharmacokinetic Data

Parameter Value Units Species
Ka 0.41 10'6/M -
Ka 1.14 10'6/M -

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum IC50 = 70.0 nM 7.16 Antiplasmodial activity against chloroquine-sensitive, mefloquine-resistant ring... 21207937
Plasmodium falciparum IC50 = 72.0 nM 7.14 Antiplasmodial activity against chloroquine and pyrimethamine-resistant ring sta... 21207937
Plasmodium falciparum IC50 = 82.0 nM 7.09 Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum W2 18207399
Plasmodium falciparum IC50 = 82.0 nM 7.09 Antiplasmodial activity against chloroquine-resistant ring stage Plasmodium falc... 21207937
Plasmodium falciparum IC50 = 130.0 nM 6.89 Antiplasmodial activity against chloroquine-sensitive ring stage Plasmodium falc... 21207937
HUVEC IC50 = 674.0 nM 6.17 Cytotoxicity against HUVEC cells 18207399
Trypanosoma brucei brucei IC50 = 900.0 nM 6.05 Antitrypanosomal activity against Trypanosoma brucei brucei 22926067
Vero IC50 = 2800.0 nM 5.55 Cytotoxicity against african green monkey Vero cells after 48 hrs by MTT assay 20952194
Vero IC50 = 2800.0 nM 5.55 Cytotoxicity against african green monkey Vero cells after 48 hrs by MTT assay 21207937
Rhodesain IC50 = 11000.0 nM 4.96 Inhibition of Trypanosoma brucei rhodesiense rhodesain 22926067
Unchecked IC50 = 23000.0 nM 4.64 Inhibition of Trypanosoma cruzi cruzaine 22926067
Cathepsin B-like cysteine protease IC50 = 95000.0 nM 4.02 Inhibition of Trypanosoma brucei CatB 22926067

Literature References

PubMed DOI Target Context # Activities
21207937 10.1021/jm101383f Plasmodium falciparum 5
21207937 10.1021/jm101383f Unchecked 3
22926067 10.1016/j.bmcl.2012.07.104 Unchecked 2
18207399 10.1016/j.bmcl.2008.01.015 Plasmodium falciparum 1
18207399 10.1016/j.bmcl.2008.01.015 HUVEC 1
18207399 10.1016/j.bmcl.2008.01.015 Unchecked 1
20952194 10.1016/j.bmcl.2010.09.110 Vero 1
20952194 10.1016/j.bmcl.2010.09.110 No relevant target 1
21207937 10.1021/jm101383f Vero 1
21207937 10.1021/jm101383f Heme 1
21207937 10.1021/jm101383f Nucleic Acid 1
22926067 10.1016/j.bmcl.2012.07.104 Rhodesain 1
22926067 10.1016/j.bmcl.2012.07.104 Cathepsin B-like cysteine protease 1
22926067 10.1016/j.bmcl.2012.07.104 Trypanosoma brucei brucei 1
22926067 10.1016/j.bmcl.2012.07.104 Vero 1

Data from ChEMBL 36 via Core Engine