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Compound Detail

CHEMBL218467

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CCOC(=O)C(=CNc1ccc2sc3ccccc3c2c1)C(=O)OCC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL218467
Phase Preclinical
Structure Type MOL
InChI Key CRRPBVYHMALQSC-UHFFFAOYSA-N
4
Targets
11
Activities
2
Assay Types
0
PK Parameters
6
Publications
0
Known Names

Molecular Properties

369.4
MW (Da)
4.48
ALogP
6
HBA
1
HBD
64.6
PSA (Ų)
0.30
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 C20H19NO4S
MW 369.44
Aromatic Rings 3
Heavy Atoms 26
NP-Likeness -1.18

Activity Summary

IC50 8 meas. best 6.8
Ki 3 meas. best 7.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Dihydroorotate dehydrogenase
CHEMBL3486
 Ki 7.7 7.7 20.0 1
Unchecked
CHEMBL612545
 Ki 7.7 7.7 20.0 1
Dihydroorotate dehydrogenase
CHEMBL3486
 IC50 6.8 6.8 160.0 1
Unchecked
CHEMBL612545
 IC50 6.8 6.8 160.0 1
Plasmodium falciparum
CHEMBL364
 IC50 5.75 5.75 1800.0 1
Dihydroorotate dehydrogenase (quinone), mitochondrial
CHEMBL1966
 Ki 5.44 5.44 3630.0 1
Dihydroorotate dehydrogenase (quinone), mitochondrial
CHEMBL1966
 IC50 4.53 4.525 29570.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Dihydroorotate dehydrogenase Ki = 20.0 nM 7.7 Inhibition of recombinant Plasmodium falciparum DHODH 17228860
Unchecked Ki = 20.0 nM 7.7 Inhibition of homologous location truncated N-terminal His-tagged Plasmodium fal... 28669445
Dihydroorotate dehydrogenase IC50 = 160.0 nM 6.8 Inhibition of recombinant Plasmodium falciparum DHODH 17228860
Unchecked IC50 = 160.0 nM 6.8 Inhibition of homologous location truncated N-terminal His-tagged Plasmodium fal... 28669445
Plasmodium falciparum IC50 = 1800.0 nM 5.75 Antimalarial activity against Plasmodium falciparum NF54 3D7 after 48 hrs 17228860
Dihydroorotate dehydrogenase (quinone), mitochondrial Ki = 3630.0 nM 5.44 Inhibition of human recombinant DHODH 17228860
Dihydroorotate dehydrogenase (quinone), mitochondrial IC50 = 29570.0 nM 4.53 Inhibition of human recombinant DHODH 17228860
Dihydroorotate dehydrogenase (quinone), mitochondrial IC50 = 30000.0 nM 4.52 Inhibition of homologous location truncated N-terminal His-tagged human DHODH ex... 28669445

Literature References

PubMed DOI Target Context # Activities
17228860 10.1021/jm060687j Dihydroorotate dehydrogenase (quinone), mitochondrial 5
17228860 10.1021/jm060687j Dihydroorotate dehydrogenase 3
28669445 10.1016/j.bmcl.2017.06.052 Unchecked 2
17228860 10.1021/jm060687j Unchecked 1
17228860 10.1021/jm060687j Plasmodium falciparum 1
28669445 10.1016/j.bmcl.2017.06.052 Dihydroorotate dehydrogenase (quinone), mitochondrial 1

Data from ChEMBL 36 via Core Engine