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Compound Detail

CHEMBL600689

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CCOC(=O)c1[nH]c(C)c(Cc2ccc(OCC)cc2)c1C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL600689
Phase Preclinical
Structure Type MOL
InChI Key AHTZIFIBNCSFEG-UHFFFAOYSA-N
6
Targets
10
Activities
2
Assay Types
0
PK Parameters
12
Publications
0
Known Names

Molecular Properties

301.4
MW (Da)
3.80
ALogP
3
HBA
1
HBD
51.3
PSA (Ų)
0.83
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C18H23NO3
MW 301.39
Aromatic Rings 2
Heavy Atoms 22
NP-Likeness -0.89

Activity Summary

IC50 6 meas. best 7.4
EC50 4 meas. best 6.64

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Dihydroorotate dehydrogenase, mitochondrial, putative
CHEMBL3988602
 IC50 7.4 7.4 40.0 1
Unchecked
CHEMBL612545
 IC50 7.35 6.96 45.0 2
Dihydroorotate dehydrogenase (quinone), mitochondrial
CHEMBL3988598
 IC50 7.22 7.22 60.0 1
Dihydroorotate dehydrogenase
CHEMBL3486
 IC50 7.08 7.08 83.0 1
Plasmodium falciparum
CHEMBL364
 EC50 6.64 6.5725 230.0 4
Dihydroorotate dehydrogenase (quinone), mitochondrial
CHEMBL3588732
 IC50 6.57 6.57 270.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Dihydroorotate dehydrogenase, mitochondrial, putative IC50 = 40.0 nM 7.4 Enzymatic Assays: Type 2 DHODH activity was monitored with either the direct ass... -
Unchecked IC50 = 45.0 nM 7.35 Inhibition of N-terminal His6-tagged Plasmodium vivax DHODH expressed in Escheri... 32248693
Dihydroorotate dehydrogenase (quinone), mitochondrial IC50 = 60.0 nM 7.22 Enzymatic Assays: Type 2 DHODH activity was monitored with either the direct ass... -
Dihydroorotate dehydrogenase IC50 = 83.0 nM 7.08 Enzymatic Assays: Type 2 DHODH activity was monitored with either the direct ass... -
Plasmodium falciparum EC50 = 230.0 nM 6.64 Antimalarial activity against Plasmodium falciparum 3D7 infected in human red bl... 32248693
Plasmodium falciparum EC50 = 230.0 nM 6.64 Antiplasmodial activity against Plasmodium falciparum 3D7 37357390
Unchecked IC50 = 270.0 nM 6.57 Inhibition of N-terminal His6-tagged Plasmodium falciparum DHODH expressed in Es... 32248693
Dihydroorotate dehydrogenase (quinone), mitochondrial IC50 = 270.0 nM 6.57 Inhibition of Plasmodium falciparum DHODH 37357390
Plasmodium falciparum EC50 = 278.7 nM 6.55 NOVARTIS: Inhibition of Plasmodium falciparum 3D7 (drug-susceptible) proliferati... 18579783
Plasmodium falciparum EC50 = 347.0 nM 6.46 NOVARTIS: Inhibition of Plasmodium falciparum W2 (drug-resistant) proliferation ... 18579783

Literature References

PubMed DOI Target Context # Activities
18579783 10.1073/pnas.0802982105 Plasmodium falciparum 2
32248693 10.1021/acs.jmedchem.0c00311 Unchecked 2
32248693 10.1021/acs.jmedchem.0c00311 No relevant target 2
32248693 10.1021/acs.jmedchem.0c00311 ADMET 2
37357390 10.1021/acs.jmedchem.3c00206 Dihydroorotate dehydrogenase (quinone), mitochondrial 2
18579783 10.1073/pnas.0802982105 Unchecked 1
18579783 10.1073/pnas.0802982105 Huh-7 1
22096101 10.1126/science.1211936 Plasmodium yoelii 1
32248693 10.1021/acs.jmedchem.0c00311 Dihydroorotate dehydrogenase (quinone), mitochondrial 1
32248693 10.1021/acs.jmedchem.0c00311 Plasmodium falciparum 1
32248693 10.1021/acs.jmedchem.0c00311 Albumin 1
37357390 10.1021/acs.jmedchem.3c00206 Plasmodium falciparum 1

Data from ChEMBL 36 via Core Engine