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Compound Detail

CHEMBL492529

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Cc1cc(Nc2ccc(C(F)(F)F)cc2)n2ncnc2n1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL492529
Phase Preclinical
Structure Type MOL
InChI Key LRHHXKBKRNNFRV-UHFFFAOYSA-N

Known Names

DSM-74
4
Targets
8
Activities
3
Assay Types
9
PK Parameters
16
Publications
1
Known Names

Molecular Properties

293.2
MW (Da)
3.20
ALogP
5
HBA
1
HBD
55.1
PSA (Ų)
0.79
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C13H10F3N5
MW 293.25
Aromatic Rings 3
Heavy Atoms 21
NP-Likeness -2.42

Activity Summary

IC50 6 meas. best 6.58
EC50 1 meas. best 6.47
Kd 1 meas. best 6.77

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Dihydroorotate dehydrogenase
CHEMBL3486
 Kd 6.77 6.77 170.0 1
Plasmodium falciparum
CHEMBL364
 IC50 6.58 6.58 260.0 1
Dihydroorotate dehydrogenase
CHEMBL3486
 IC50 6.57 6.56 270.0 2
Unchecked
CHEMBL612545
 IC50 6.55 6.55 280.0 2
Plasmodium falciparum
CHEMBL364
 EC50 6.47 6.47 340.0 1
Plasmodium berghei
CHEMBL612653
 IC50 6.42 6.42 380.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 13146.4 ng.hr.mL-1 Mus musculus
AUC 57462.34 ng.hr.mL-1 Mus musculus
CL 7.5 mL.min-1.g-1 Homo sapiens
CL 8.0 mL.min-1.g-1 Homo sapiens
Cmax 7900.0 nM Mus musculus
Cmax 27600.0 nM Mus musculus
T1/2 3.833 hr Homo sapiens
T1/2 1.8 hr Mus musculus
T1/2 3.0 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Dihydroorotate dehydrogenase Kd = 170.0 nM 6.77 Binding affinity to Plasmodium falciparum DHODH by isothermal titration calorime... 24801997
Plasmodium falciparum IC50 = 260.0 nM 6.58 Antimalarial activity against Plasmodium falciparum 3D7 infected in RBC after 72... 24801997
Dihydroorotate dehydrogenase IC50 = 270.0 nM 6.57 Inhibition of N-terminal His6-tagged recombinant Plasmodium falciparum DHODH (am... 24801997
Dihydroorotate dehydrogenase IC50 = 280.0 nM 6.55 Inhibition of Plasmodium falciparum DHODH 19296651
Unchecked IC50 = 280.0 nM 6.55 Inhibition of Plasmodium falciparum DHODH expressed in Escherichia coli using L-... 27721149
Unchecked IC50 = 280.0 nM 6.55 Inhibition of Plasmodium falciparum DHODH 31557612
Plasmodium falciparum EC50 = 340.0 nM 6.47 Antiplasmodial activity against Plasmodium falciparum 3D7 by [3H]hypoxanthine up... 19296651
Plasmodium berghei IC50 = 380.0 nM 6.42 Inhibition of Plasmodium berghei ANKA DHODH 19296651

Literature References

PubMed DOI Target Context # Activities
19296651 10.1021/jm801343r Mus musculus 13
24801997 10.1021/jm500481t Dihydroorotate dehydrogenase (quinone), mitochondrial 4
19296651 10.1021/jm801343r Plasmodium berghei 3
19296651 10.1021/jm801343r Liver microsomes 2
21517059 10.1021/jm200265b No relevant target 2
24801997 10.1021/jm500481t Dihydroorotate dehydrogenase 2
19296651 10.1021/jm801343r Dihydroorotate dehydrogenase (quinone), mitochondrial 1
19296651 10.1021/jm801343r Plasmodium falciparum 1
19296651 10.1021/jm801343r Dihydroorotate dehydrogenase 1
21517059 10.1021/jm200265b Liver microsomes 1
21517059 10.1021/jm200265b Plasma 1
24801997 10.1021/jm500481t Plasmodium falciparum 1
24801997 10.1021/jm500481t No relevant target 1
24801997 10.1021/jm500481t Unchecked 1
27721149 10.1016/j.ejmech.2016.09.085 Unchecked 1
31557612 10.1016/j.ejmech.2019.111681 Unchecked 1

Data from ChEMBL 36 via Core Engine