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Compound Detail

CHEMBL1738786

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Cc1cc(Nc2ccc(C(F)(F)F)cc2)n2nc(C(C)(F)F)nc2n1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1738786
Phase Preclinical
Structure Type MOL
InChI Key CUCVTDOXQYMYKL-UHFFFAOYSA-N
8
Targets
20
Activities
3
Assay Types
30
PK Parameters
20
Publications
0
Known Names

Molecular Properties

357.3
MW (Da)
4.31
ALogP
5
HBA
1
HBD
55.1
PSA (Ų)
0.71
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C15H12F5N5
MW 357.29
Aromatic Rings 3
Heavy Atoms 25
NP-Likeness -1.93

Activity Summary

IC50 11 meas. best 8.44
EC50 8 meas. best 8.34
Kd 1 meas. best 7.57

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
 IC50 8.44 8.44 3.6 1
Plasmodium falciparum
CHEMBL364
 EC50 8.34 8.045 4.6 8
Dihydroorotate dehydrogenase
CHEMBL3486
 Kd 7.57 7.57 27.0 1
Dihydroorotate dehydrogenase
CHEMBL3486
 IC50 7.42 7.38 38.0 2
Dihydroorotate dehydrogenase (quinone), mitochondrial
CHEMBL3588732
 IC50 7.42 7.42 38.0 1
Unchecked
CHEMBL612545
 IC50 7.42 6.7067 38.0 3
Dihydroorotate dehydrogenase (quinone), mitochondrial
CHEMBL1966
 IC50 5.16 5.16 7000.0 1
Dihydroorotate dehydrogenase (quinone), mitochondrial
CHEMBL2383
 IC50 5.14 5.14 7200.0 1
Dihydroorotate dehydrogenase (quinone), mitochondrial
CHEMBL4523950
 IC50 4.68 4.68 21000.0 1
Dihydroorotate dehydrogenase (quinone), mitochondrial
CHEMBL2991
 IC50 4.62 4.62 24000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 238.21 ng.hr.mL-1 Mus musculus
AUC 3388.18 ng.hr.mL-1 Mus musculus
AUC 25053.17 ng.hr.mL-1 Mus musculus
AUC 88222.05 ng.hr.mL-1 Mus musculus
AUC 1387.36 ng.hr.mL-1 Rattus norvegicus
AUC 122025.25 ng.hr.mL-1 Rattus norvegicus
AUC 15013.33 ng.hr.mL-1 Mus musculus
AUC 16317.43 ng.hr.mL-1 Mus musculus
CL 10.1 mL.min-1.g-1 Mus musculus
CL 5.0 mL.min-1.g-1 Homo sapiens
CL 23.2 mL.min-1.kg-1 Rattus norvegicus
CL 12.6 mL.min-1.kg-1 Rattus norvegicus
Cmax 200.0 nM Mus musculus
Cmax 1850.0 nM Mus musculus
Cmax 9860.0 nM Mus musculus
Cmax 57000.0 nM Mus musculus
Cmax 900.0 nM Rattus norvegicus
Cmax 11400.0 nM Rattus norvegicus
Cmax 6300.0 nM Mus musculus
Cmax 6300.0 nM Mus musculus
F 97.0 % Rattus norvegicus
F 100.0 % Rattus norvegicus
T1/2 1.6 hr Mus musculus
T1/2 1.9 hr Mus musculus
T1/2 2.1 hr Mus musculus
T1/2 6.1 hr Rattus norvegicus
T1/2 3.8 hr Rattus norvegicus
T1/2 6.0 hr Rattus norvegicus
T1/2 17.0 hr Rattus norvegicus
Tmax 0.5 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum IC50 = 3.6 nM 8.44 Antimalarial activity against Plasmodium falciparum 3D7 infected in RBC after 72... 24801997
Plasmodium falciparum EC50 = 4.6 nM 8.34 Antimalarial activity against atovoquone-resistant Plasmodium falciparum TM90C2B... 21696174
Plasmodium falciparum EC50 = 6.2 nM 8.21 Antimalarial activity against Plasmodium falciparum 3D7 by [3H]hypoxanthine inco... 21696174
Plasmodium falciparum EC50 = 7.9 nM 8.1 Antimalarial activity against atovoquone-resistant Plasmodium falciparum TM90C2A... 21696174
Plasmodium falciparum EC50 = 7.9 nM 8.1 Antimalarial activity against drug-sensitive Plasmodium falciparum HB3 by [3H]hy... 21696174
Plasmodium falciparum EC50 = 10.0 nM 8.0 Antimalarial activity against Plasmodium falciparum 3D7 by [3H]hypoxanthine inco... 21696174
Plasmodium falciparum EC50 = 12.0 nM 7.92 Antimalarial activity against drug-sensitive Plasmodium falciparum D6 by [3H]hyp... 21696174
Plasmodium falciparum EC50 = 13.0 nM 7.89 Antimalarial activity against chloroquine-resistant Plasmodium falciparum Dd2 by... 21696174
Plasmodium falciparum EC50 = 16.0 nM 7.8 Antimalarial activity against chloroquine and pyrimethamine-resistant Plasmodium... 21696174
Dihydroorotate dehydrogenase Kd = 27.0 nM 7.57 Binding affinity to Plasmodium falciparum DHODH by isothermal titration calorime... 24801997
Dihydroorotate dehydrogenase (quinone), mitochondrial IC50 = 38.0 nM 7.42 Inhibiton Assay: For studying inhibition of Plasmodium or human DHODH enzyme, tw... -
Unchecked IC50 = 38.0 nM 7.42 Inhibition of Plasmodium falciparum DHODH 31557612
Dihydroorotate dehydrogenase IC50 = 38.0 nM 7.42 Inhibition of Plasmodium falciparum C-terminal hexa-His tagged DHODH expressed i... 21696174
Dihydroorotate dehydrogenase IC50 = 46.0 nM 7.34 Inhibition of N-terminal His6-tagged recombinant Plasmodium falciparum DHODH (am... 24801997
Unchecked IC50 = 84.0 nM 7.08 Inhibition of Plasmodium vivax C-terminal hexa-His tagged DHODH expressed in Esc... 21696174
Unchecked IC50 = 2400.0 nM 5.62 Inhibition of Plasmodium berghei C-terminal hexa-His tagged DHODH expressed in E... 21696174
Dihydroorotate dehydrogenase (quinone), mitochondrial IC50 = 7000.0 nM 5.16 Inhibition of human DHODH 31557612
Dihydroorotate dehydrogenase (quinone), mitochondrial IC50 = 7200.0 nM 5.14 Inhibition of rat DHODH (amino acid residues 30 to 396) expressed in Escherichia... 24801997
Dihydroorotate dehydrogenase (quinone), mitochondrial IC50 = 21000.0 nM 4.68 Inhibition of Schistosoma mansoni DHODH 31557612
Dihydroorotate dehydrogenase (quinone), mitochondrial IC50 = 24000.0 nM 4.62 Inhibition of mouse DHODH (amino acid residues 30 to 396) expressed in Escherich... 24801997

Literature References

PubMed DOI Target Context # Activities
21696174 10.1021/jm200592f Mus musculus 25
21696174 10.1021/jm200592f Rattus norvegicus 16
21696174 10.1021/jm200592f Plasmodium falciparum 10
24801997 10.1021/jm500481t Unchecked 5
24801997 10.1021/jm500481t Dihydroorotate dehydrogenase (quinone), mitochondrial 5
21696174 10.1021/jm200592f Plasma 4
21696174 10.1021/jm200592f Unchecked 3
31557612 10.1016/j.ejmech.2019.111681 Unchecked 2
31557612 10.1016/j.ejmech.2019.111681 Dihydroorotate dehydrogenase (quinone), mitochondrial 2
24801997 10.1021/jm500481t Dihydroorotate dehydrogenase 2
21696174 10.1021/jm200592f No relevant target 2
21696174 10.1021/jm200592f L1210 1
21696174 10.1021/jm200592f Dihydroorotate dehydrogenase 1
21696174 10.1021/jm200592f Nucleic Acid 1
24801997 10.1021/jm500481t Plasmodium falciparum 1
21696174 10.1021/jm200592f Dihydroorotate dehydrogenase (quinone), mitochondrial 1
24801997 10.1021/jm500481t No relevant target 1
21696174 10.1021/jm200592f Liver microsomes 1
21696174 10.1021/jm200592f Liver 1
21696174 10.1021/jm200592f HepG2 1

Data from ChEMBL 36 via Core Engine