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Compound Detail

CHEMBL4633246

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Cc1c(Cc2ccc(C(F)(F)F)nc2)c[nH]c1C(=O)NC1CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4633246
Phase Preclinical
Structure Type MOL
InChI Key AFOVOYRODSYDMK-UHFFFAOYSA-N
4
Targets
17
Activities
2
Assay Types
30
PK Parameters
20
Publications
0
Known Names

Molecular Properties

323.3
MW (Da)
3.22
ALogP
2
HBA
2
HBD
57.8
PSA (Ų)
0.91
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C16H16F3N3O
MW 323.32
Aromatic Rings 2
Heavy Atoms 23
NP-Likeness -0.97

Activity Summary

EC50 10 meas. best 7.89
IC50 7 meas. best 7.85

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
 EC50 7.89 7.59 13.0 10
Unchecked
CHEMBL612545
 IC50 7.85 7.775 14.0 4
Dihydroorotate dehydrogenase (quinone), mitochondrial
CHEMBL3588732
 IC50 7.7 7.7 20.0 1
Cytochrome P450 3A4/3A5
CHEMBL2111472
 IC50 5.26 5.26 5500.0 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 1810.59 ng.hr.mL-1 Mus musculus
AUC 17976.59 ng.hr.mL-1 Mus musculus
AUC 14387.74 ng.hr.mL-1 Mus musculus
AUC 71130.4 ng.hr.mL-1 Mus musculus
AUC 56904.32 ng.hr.mL-1 Mus musculus
AUC 1648.93 ng.hr.mL-1 Rattus norvegicus
AUC 65957.28 ng.hr.mL-1 Rattus norvegicus
AUC 678.97 ng.hr.mL-1 Mus musculus
AUC 8632.64 ng.hr.mL-1 Mus musculus
CL 26.1 mL.min-1.kg-1 Mus musculus
CL 28600.0 mL.min-1.g-1 Rattus norvegicus
Cmax 4600.0 nM Mus musculus
Cmax 3700.0 nM Mus musculus
Cmax 8400.0 nM Mus musculus
Cmax 6700.0 nM Mus musculus
Cmax 42300.0 nM Mus musculus
Cmax 33800.0 nM Mus musculus
Cmax 1700.0 nM Rattus norvegicus
Cmax 27000.0 nM Rattus norvegicus
Cmax 600.0 nM Mus musculus
Cmax 7810.0 nM Mus musculus
F 100.0 % Mus musculus
F 100.0 % Mus musculus
F 91.0 % Rattus norvegicus
F 100.0 % Rattus norvegicus
T1/2 2.8 hr Mus musculus
T1/2 2.6 hr Mus musculus
T1/2 3.6 hr Mus musculus
T1/2 14.6 hr Rattus norvegicus
T1/2 3.9 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum EC50 = 13.0 nM 7.89 Antimalarial activity against Plasmodium falciparum R1BC1A harboring DHODH L531F... 32248693
Plasmodium falciparum EC50 = 14.0 nM 7.85 Antimalarial activity against Plasmodium falciparum 3D7 infected in human red bl... 32248693
Plasmodium falciparum EC50 = 14.0 nM 7.85 Antimalarial activity against drug-resistant Plasmodium falciparum 3D7 infected ... 33876936
Plasmodium falciparum EC50 = 14.0 nM 7.85 Antiplasmodial activity against Plasmodium falciparum 3D7 37357390
Unchecked IC50 = 14.0 nM 7.85 Inhibition of N-terminal His6-tagged Plasmodium vivax DHODH expressed in Escheri... 32248693
Unchecked IC50 = 14.0 nM 7.85 Inhibition of Plasmodium vivax DHODH expressed in Escherichia coli BL21-DE3 usin... 33876936
Plasmodium falciparum EC50 = 16.0 nM 7.8 Antimalarial activity against multidrug-resistant Plasmodium falciparum Dd2 meas... 32248693
Plasmodium falciparum EC50 = 16.0 nM 7.8 Antimalarial activity against Plasmodium falciparum 3D70087/N9 infected in po do... 32248693
Dihydroorotate dehydrogenase (quinone), mitochondrial IC50 = 20.0 nM 7.7 Inhibition of Plasmodium falciparum DHODH 37357390
Unchecked IC50 = 20.0 nM 7.7 Inhibition of N-terminal His6-tagged Plasmodium falciparum DHODH expressed in Es... 32248693
Unchecked IC50 = 20.0 nM 7.7 Inhibition of Plasmodium falciparum DHODH expressed in Escherichia coli BL21-DE3... 33876936
Plasmodium falciparum EC50 = 24.0 nM 7.62 Antimalarial activity against Plasmodium falciparum R10C1B harboring DHODH G181C... 32248693
Plasmodium falciparum EC50 = 78.0 nM 7.11 Antimalarial activity against Plasmodium falciparum R2B harboring DHODH R265G mu... 32248693
Plasmodium falciparum EC50 = 83.0 nM 7.08 Antimalarial activity against Plasmodium falciparum 1D3 measured after 72 hrs by... 32248693
Plasmodium falciparum EC50 = 89.0 nM 7.05 Antimalarial activity against Plasmodium falciparum R1AC1B harboring DHODH C276F... 32248693
Cytochrome P450 3A4/3A5 IC50 = 5500.0 nM 5.26 Inhibition of CYP3A4/5 in human liver microsomes using testosterone as substrate... 32248693
Cytochrome P450 3A4/3A5 IC50 = 5500.0 nM 5.26 Inhibition of CYP3A4/5 in human liver microsomes using midazolam as substrate pr... 32248693

Literature References

PubMed DOI Target Context # Activities
32248693 10.1021/acs.jmedchem.0c00311 ADMET 56
32248693 10.1021/acs.jmedchem.0c00311 Plasmodium falciparum 13
32248693 10.1021/acs.jmedchem.0c00311 Unchecked 10
32248693 10.1021/acs.jmedchem.0c00311 No relevant target 7
32248693 10.1021/acs.jmedchem.0c00311 Cytochrome P450 3A4/3A5 6
32248693 10.1021/acs.jmedchem.0c00311 Dihydroorotate dehydrogenase (quinone), mitochondrial 3
32248693 10.1021/acs.jmedchem.0c00311 Cytochrome P450 2D6 3
32248693 10.1021/acs.jmedchem.0c00311 Cytochrome P450 2C19 3
32248693 10.1021/acs.jmedchem.0c00311 Cytochrome P450 2C9 3
32248693 10.1021/acs.jmedchem.0c00311 Cytochrome P450 1A2 3
37357390 10.1021/acs.jmedchem.3c00206 Dihydroorotate dehydrogenase (quinone), mitochondrial 2
33876936 10.1021/acs.jmedchem.1c00173 Unchecked 2
32248693 10.1021/acs.jmedchem.0c00311 Albumin 2
32248693 10.1021/acs.jmedchem.0c00311 Potassium voltage-gated channel subfamily A member 5 1
32248693 10.1021/acs.jmedchem.0c00311 Voltage-dependent L-type calcium channel subunit alpha-1C 1
32248693 10.1021/acs.jmedchem.0c00311 Sodium channel protein type 5 subunit alpha 1
32248693 10.1021/acs.jmedchem.0c00311 Voltage-gated inwardly rectifying potassium channel KCNH2 1
32248693 10.1021/acs.jmedchem.0c00311 L1210 1
33876936 10.1021/acs.jmedchem.1c00173 Dihydroorotate dehydrogenase (quinone), mitochondrial 1
37357390 10.1021/acs.jmedchem.3c00206 Plasmodium falciparum 1

Data from ChEMBL 36 via Core Engine