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Compound Detail

CHEMBL1236

DESETHYLCHLOROQUINE
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CCNCCCC(C)Nc1ccnc2cc(Cl)ccc12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1236
Name DESETHYLCHLOROQUINE
Phase Preclinical
Structure Type MOL
InChI Key MCYUUUTUAAGOOT-UHFFFAOYSA-N
3
Targets
12
Activities
1
Assay Types
4
PK Parameters
12
Publications
0
Known Names

Molecular Properties

291.8
MW (Da)
4.08
ALogP
3
HBA
2
HBD
37.0
PSA (Ų)
0.75
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C16H22ClN3
MW 291.83
Aromatic Rings 2
Heavy Atoms 20
NP-Likeness -0.86

Activity Summary

IC50 12 meas. best 7.77

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
 IC50 7.77 6.974 17.0 10
Histidine-rich protein PFHRP-II
CHEMBL1923
 IC50 4.82 4.82 15000.0 1
Heme
CHEMBL4651321
 IC50 4.35 4.35 45000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 24396.99 ng.hr.mL-1 Homo sapiens
AUC 28745.25 ng.hr.mL-1 Homo sapiens
Ka 180000.0 M-1 -
T1/2 290.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum IC50 = 17.0 nM 7.77 In vitro inhibition of chloroquine-sensitive Plasmodium falciparum HB3 9046333
Plasmodium falciparum IC50 = 17.8 nM 7.75 Antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum 17967917
Plasmodium falciparum IC50 = 18.2 nM 7.74 Antimalarial activity after 72 hrs against chloroquine-sensitive Plasmodium falc... 17846138
Plasmodium falciparum IC50 = 19.0 nM 7.72 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum 3D7 as... -
Plasmodium falciparum IC50 = 37.4 nM 7.43 Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum 17967917
Plasmodium falciparum IC50 = 45.0 nM 7.35 Parasite growth in chloroquine-sensitive Plasmodium falciparum NF54 10579825
Plasmodium falciparum IC50 = 372.0 nM 6.43 Antimalarial activity after 72 hrs against chloroquine-resistant Plasmodium falc... 17846138
Plasmodium falciparum IC50 = 720.0 nM 6.14 Antimalarial activity against chloroquine-resistant Plasmodium falciparum K1 ass... -
Plasmodium falciparum IC50 = 1300.0 nM 5.89 Parasite growth in chloroquine-sensitive Plasmodium falciparum K1 10579825
Plasmodium falciparum IC50 = 3000.0 nM 5.52 Antimicrobial activity against Plasmodium falciparum 20185316
Histidine-rich protein PFHRP-II IC50 = 15000.0 nM 4.82 Inhibition of hematin polymerization 10579825
Heme IC50 = 45000.0 nM 4.35 Inhibition of heme polymerization in Plasmodium falciparum after 15 min by liqui... -

Literature References

PubMed DOI Target Context # Activities
17967917 10.1128/aac.00555-07 Homo sapiens 3
18955514 10.1128/aac.01111-08 ADMET 3
10579825 10.1021/jm9902180 Plasmodium falciparum 2
17846138 10.1128/aac.00669-07 Plasmodium falciparum 2
17967917 10.1128/aac.00555-07 Plasmodium falciparum 2
- 10.1007/s00044-007-9025-8 Plasmodium falciparum 2
9046333 10.1021/jm960370r Plasmodium falciparum 1
9046333 10.1021/jm960370r Molecular identity unknown 1
10579825 10.1021/jm9902180 ADMET 1
10579825 10.1021/jm9902180 Histidine-rich protein PFHRP-II 1
20185316 10.1016/j.bmc.2010.01.068 Plasmodium falciparum 1
- 10.1007/s00044-007-9025-8 Heme 1

Data from ChEMBL 36 via Core Engine