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Compound Detail

CHEMBL600928

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CCOC(=O)C1=C(C)N/C(=C/c2cc(C)n(-c3ccccc3C(F)(F)F)c2C)C1=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL600928
Phase Preclinical
Structure Type MOL
InChI Key LGOJAESSCLSLCP-GZTJUZNOSA-N
2
Targets
8
Activities
1
Assay Types
14
PK Parameters
15
Publications
0
Known Names

Molecular Properties

418.4
MW (Da)
4.46
ALogP
5
HBA
1
HBD
60.3
PSA (Ų)
0.45
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C22H21F3N2O3
MW 418.42
Aromatic Rings 2
Heavy Atoms 30
NP-Likeness -1.30

Activity Summary

EC50 8 meas. best 8.66

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
 EC50 8.66 7.6214 2.2 7
L6
CHEMBL614793
 EC50 4.82 4.82 15000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 73.0 mL.min-1.kg-1 Rattus norvegicus
CL 50.0 mL.min-1.g-1 Mus musculus
Cmax 3300.0 nM Rattus norvegicus
Cmax 110.0 nM Rattus norvegicus
F 45.7 % Rattus norvegicus
F 6.0 % Rattus norvegicus
T1/2 9.1 hr Rattus norvegicus
T1/2 12.0 hr Rattus norvegicus
T1/2 7.9 hr Rattus norvegicus
T1/2 0.5833 hr Mus musculus
T1/2 0.7333 hr Rattus norvegicus
T1/2 0.9667 hr Homo sapiens
Tmax 0.25 hr Rattus norvegicus
Tmax 3.333 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum EC50 = 2.2 nM 8.66 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum D6 23517371
Plasmodium falciparum EC50 = 8.4 nM 8.08 Antimalarial activity against chloroquine-resistant Plasmodium falciparum W2 23517371
Plasmodium falciparum EC50 = 8.6 nM 8.07 Antimalarial activity against multidrug-resistant and atovaquone-sensitive Plasm... 23517371
Plasmodium falciparum EC50 = 9.0 nM 8.05 Antimalarial activity against erythrocytic stage of chloroquine and pyrimethamin... 23517371
Plasmodium falciparum EC50 = 11.0 nM 7.96 Antimalarial activity against atovaquone-resistant Plasmodium falciparum TM90C2B 23517371
Plasmodium falciparum EC50 = 471.0 nM 6.33 NOVARTIS: Inhibition of Plasmodium falciparum 3D7 (drug-susceptible) proliferati... 18579783
Plasmodium falciparum EC50 = 628.0 nM 6.2 NOVARTIS: Inhibition of Plasmodium falciparum W2 (drug-resistant) proliferation ... 18579783
L6 EC50 = 15000.0 nM 4.82 Cytotoxicity against rat L6 cells after 72 hrs by Alamar blue assay 23517371

Literature References

PubMed DOI Target Context # Activities
23517371 10.1021/jm400009c Rattus norvegicus 13
23517371 10.1021/jm400009c Plasmodium berghei 9
23517371 10.1021/jm400009c Liver microsomes 8
23517371 10.1021/jm400009c ADMET 7
23517371 10.1021/jm400009c Plasmodium falciparum 5
23517371 10.1021/jm400009c No relevant target 4
23517371 10.1021/jm400009c Liver 3
18579783 10.1073/pnas.0802982105 Plasmodium falciparum 2
23517371 10.1021/jm400009c Plasma 2
18579783 10.1073/pnas.0802982105 Unchecked 1
18579783 10.1073/pnas.0802982105 Huh-7 1
22096101 10.1126/science.1211936 Plasmodium yoelii 1
23517371 10.1021/jm400009c Blood 1
23517371 10.1021/jm400009c Albumin 1
23517371 10.1021/jm400009c L6 1

Data from ChEMBL 36 via Core Engine