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Compound Detail

CHEMBL598685

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CC(C)NCC(O)Cn1c2ccc(Cl)cc2c2cc(Cl)ccc21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL598685
Phase Preclinical
Structure Type MOL
InChI Key KOZMMZGWHLFBOI-UHFFFAOYSA-N
4
Targets
9
Activities
3
Assay Types
0
PK Parameters
17
Publications
0
Known Names

Molecular Properties

351.3
MW (Da)
4.46
ALogP
3
HBA
2
HBD
37.2
PSA (Ų)
0.71
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C18H20Cl2N2O
MW 351.28
Aromatic Rings 3
Heavy Atoms 23
NP-Likeness -0.79

Activity Summary

IC50 5 meas. best 7.16
EC50 2 meas. best 7.41
Kd 2 meas. best 8.15

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
HSP90
CHEMBL1795086
 Kd 8.15 8.15 7.0 1
Plasmodium falciparum
CHEMBL364
 EC50 7.41 7.075 38.9 2
Plasmodium falciparum
CHEMBL364
 IC50 7.16 6.6 70.0 3
L6
CHEMBL614793
 IC50 5.58 5.58 2613.0 1
Plasmodium yoelii
CHEMBL612889
 IC50 5.53 5.53 2973.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
HSP90 Kd = 7.0 nM 8.15 Binding affinity to Plasmodium falciparum HSP90 nucleotide binding domain by SPR... 29754074
Plasmodium falciparum EC50 = 38.9 nM 7.41 NOVARTIS: Inhibition of Plasmodium falciparum W2 (drug-resistant) proliferation ... 18579783
Plasmodium falciparum IC50 = 70.0 nM 7.16 Antimalarial activity against Plasmodium falciparum NF54 infected in human eryth... 27312008
Plasmodium falciparum EC50 = 183.2 nM 6.74 NOVARTIS: Inhibition of Plasmodium falciparum 3D7 (drug-susceptible) proliferati... 18579783
Plasmodium falciparum IC50 = 480.0 nM 6.32 Antimalarial activity against Plasmodium falciparum 3D7 infected in human erythr... 27312008
Plasmodium falciparum IC50 = 480.0 nM 6.32 Antimalarial activity against Plasmodium falciparum K1 infected in human erythro... 27312008
L6 IC50 = 2613.0 nM 5.58 Cytotoxicity against rat L6 cells after 72 hrs by alamar blue assay 27312008
Plasmodium yoelii IC50 = 2973.0 nM 5.53 NOVARTIS: Antimalarial liver stage activity measured as reduction in Plasmodium ... 22096101

Literature References

PubMed DOI Target Context # Activities
20485428 10.1038/nature09099 Plasmodium falciparum 9
27312008 10.1021/acs.jmedchem.6b00591 Plasmodium falciparum 3
22096101 10.1126/science.1211936 Plasmodium yoelii 3
18579783 10.1073/pnas.0802982105 Plasmodium falciparum 2
29754074 10.1016/j.ejmech.2018.04.038 Unchecked 2
29754074 10.1016/j.ejmech.2018.04.038 HSP90 2
20485428 10.1038/nature09099 Leishmania major 1
27312008 10.1021/acs.jmedchem.6b00591 L6 1
27312008 10.1021/acs.jmedchem.6b00591 HSP90 1
20485428 10.1038/nature09099 Raji 1
20485428 10.1038/nature09099 BJ 1
18579783 10.1073/pnas.0802982105 Unchecked 1
20485428 10.1038/nature09099 HEK293 1
20485428 10.1038/nature09099 HepG2 1
20485428 10.1038/nature09099 Trypanosoma brucei 1
20485428 10.1038/nature09099 Toxoplasma gondii 1
18579783 10.1073/pnas.0802982105 Huh-7 1

Data from ChEMBL 36 via Core Engine