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Compound Detail

CHEMBL475813

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Cc1cc(Nc2ccc3ccccc3c2)n2ncnc2n1

Basic Information

ChEMBL ID CHEMBL475813
Phase Preclinical
Structure Type MOL
InChI Key WPVMVODGPNYYEV-UHFFFAOYSA-N
4
Targets
18
Activities
2
Assay Types
3
PK Parameters
20
Publications
0
Known Names

Molecular Properties

275.3
MW (Da)
3.33
ALogP
5
HBA
1
HBD
55.1
PSA (Ų)
0.61
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 C16H13N5
MW 275.31
Aromatic Rings 4
Heavy Atoms 21
NP-Likeness -2.08

Activity Summary

IC50 11 meas. best 7.6
EC50 7 meas. best 7.24

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Dihydroorotate dehydrogenase
CHEMBL3486
IC50 7.6 7.392 25.0 5
Unchecked
CHEMBL612545
IC50 7.33 7.33 47.0 2
Plasmodium falciparum
CHEMBL364
EC50 7.24 6.9271 58.0 7
Plasmodium falciparum
CHEMBL364
IC50 7.1 6.955 79.0 2
Dihydroorotate dehydrogenase (quinone), mitochondrial
CHEMBL3588732
IC50 5.21 4.785 6100.0 2

Pharmacokinetic Data

Parameter Value Units Species
CL 96.0 mL.min-1.g-1 Homo sapiens
CL 96.0 mL.min-1.g-1 Homo sapiens
T1/2 0.3 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Dihydroorotate dehydrogenase IC50 = 25.0 nM 7.6 Inhibition of Plasmodium falciparum DHODH using dihydroorotate substrate by DCIP... 25580811
Dihydroorotate dehydrogenase IC50 = 31.0 nM 7.51 Inhibition of Plasmodium falciparum DHODH (Phe158 to Ser569) expressed in Escher... 24073986
Unchecked IC50 = 47.0 nM 7.33 Inhibition of Plasmodium falciparum DHODH expressed in Escherichia coli by DCIP ... 30703745
Unchecked IC50 = 47.0 nM 7.33 Inhibition of Plasmodium falciparum DHODH 31557612
Dihydroorotate dehydrogenase IC50 = 47.0 nM 7.33 Inhibition of Plasmodium falciparum DHODH -
Dihydroorotate dehydrogenase IC50 = 47.0 nM 7.33 Inhibition of Plasmodium falciparum DHODH assessed as reduction of 2,6-dichloroi... 18522386
Plasmodium falciparum EC50 = 58.0 nM 7.24 Antiplasmodial activity against Plasmodium falciparum D6 in erythrocytes as [3H]... 18522386
Dihydroorotate dehydrogenase IC50 = 65.0 nM 7.19 Inhibition of Plasmodium falciparum recombinant N-terminal His6-tagged DHODH (15... 30529545
Plasmodium falciparum EC50 = 66.0 nM 7.18 Antimalarial activity against Plasmodium falciparum 3D7 infected in human A posi... 21517059
Plasmodium falciparum IC50 = 79.0 nM 7.1 Antiplasmodial activity against Plasmodium falciparum 3D7 in erythrocytes as [3H... 18522386
Plasmodium falciparum EC50 = 100.0 nM 7.0 Antiplasmodial activity against Plasmodium falciparum HB3 in erythrocytes as [3H... 18522386
Plasmodium falciparum EC50 = 140.0 nM 6.85 Antiplasmodial activity against Plasmodium falciparum Dd2 in erythrocytes as [3H... 18522386
Plasmodium falciparum EC50 = 140.0 nM 6.85 Antiplasmodial activity against Plasmodium falciparum K1 in erythrocytes as [3H]... 18522386
Plasmodium falciparum IC50 = 156.2 nM 6.81 MMV: IC50 determined against P. falciparum Dd2-luc strain using a Malaria Sybr G... -
Plasmodium falciparum EC50 = 180.0 nM 6.75 Antiplasmodial activity against Plasmodium falciparum FCR3 in erythrocytes as [3... 18522386
Plasmodium falciparum EC50 = 242.0 nM 6.62 MMV: Inhibition of Plasmodium falciparum 3D7 (EC50). -
Dihydroorotate dehydrogenase (quinone), mitochondrial IC50 = 6100.0 nM 5.21 Inhibition of Plasmodium falciparum DHODH R265A mutant 18522386
Dihydroorotate dehydrogenase (quinone), mitochondrial IC50 = 44000.0 nM 4.36 Inhibition of Plasmodium falciparum DHODH F227A mutant 18522386

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3301486 Unchecked 8
- 10.6019/CHEMBL3301472 Human immunodeficiency virus 1 7
- 10.6019/CHEMBL3301472 NON-PROTEIN TARGET 6
18522386 10.1021/jm8001026 Plasmodium falciparum 6
22621375 10.1021/jm300157n Unchecked 5
20485427 10.1038/nature09107 Plasmodium falciparum 4
- 10.6019/CHEMBL3137381 Onchocerca lienalis 4
18522386 10.1021/jm8001026 Dihydroorotate dehydrogenase (quinone), mitochondrial 3
- 10.6019/CHEMBL3301546 Saccharomyces cerevisiae 3
- 10.6019/CHEMBL2363022 Schistosoma mansoni 3
30703745 10.1016/j.ejmech.2019.01.027 ADMET 3
19296651 10.1021/jm801343r Mus musculus 2
- 10.6019/CHEMBL3301451 Plasmodium falciparum 2
- 10.6019/CHEMBL3301458 Voltage-gated inwardly rectifying potassium channel KCNH2 2
21517059 10.1021/jm200265b No relevant target 2
- 10.6019/CHEMBL3433997 Solute carrier family 2, facilitated glucose transporter member 1 2
- 10.6019/CHEMBL3433997 Hexose transporter 1 2
18522386 10.1021/jm8001026 Dihydroorotate dehydrogenase 2
19296651 10.1021/jm801343r Liver microsomes 2
- 10.6019/CHEMBL3433997 Glucose transporter 2

Data from ChEMBL 36 via Core Engine