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Compound Detail

CHEMBL4165815

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Cc1cc(Oc2ccccc2)c(C)cc1NC(=O)c1c(O)nn2ccccc12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4165815
Phase Preclinical
Structure Type MOL
InChI Key MAABWDSRAWCVBC-UHFFFAOYSA-N
5
Targets
10
Activities
2
Assay Types
0
PK Parameters
10
Publications
0
Known Names

Molecular Properties

373.4
MW (Da)
4.70
ALogP
5
HBA
2
HBD
75.9
PSA (Ų)
0.54
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C22H19N3O3
MW 373.41
Aromatic Rings 4
Heavy Atoms 28
NP-Likeness -1.37

Activity Summary

IC50 6 meas. best 7.37
EC50 4 meas. best 6.24

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Dihydroorotate dehydrogenase (quinone), mitochondrial
CHEMBL1966
 IC50 7.37 7.335 43.0 2
THP-1
CHEMBL614245
 EC50 6.24 6.055 579.0 2
U-937
CHEMBL612794
 EC50 6.12 5.89 755.0 2
PBMC
CHEMBL613107
 IC50 6.08 5.105 840.0 2
Jurkat
CHEMBL397
 IC50 5.83 5.045 1470.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Dihydroorotate dehydrogenase (quinone), mitochondrial IC50 = 43.0 nM 7.37 Inhibition of recombinant N-terminal GST-tagged human DHODH (31 to 395 residues)... 29939742
Dihydroorotate dehydrogenase (quinone), mitochondrial IC50 = 50.0 nM 7.3 Inhibition of human N-terminal GST-fusion tagged DHODH (31 to 395 residues) expr... 36162075
THP-1 EC50 = 579.0 nM 6.24 Induction of cell differentiation in human THP-1 cells measured for 2 days by fl... 36162075
U-937 EC50 = 755.0 nM 6.12 Induction of cell differentiation in human U-937 cells measured for 2 days by fl... 36162075
PBMC IC50 = 840.0 nM 6.08 Immunosuppressive activity against human PBMC assessed as inhibition of PHA-stim... 29939742
THP-1 EC50 = 1344.0 nM 5.87 Induction of apoptosis in human THP-1 cells measured after 3 days by Annexin-V-F... 36162075
Jurkat IC50 = 1470.0 nM 5.83 Antiproliferative activity against human Jurkat T cells assessed as DNA content ... 29939742
U-937 EC50 = 2168.0 nM 5.66 Induction of apoptosis in human U-937 cells measured after 3 days by Annexin-V-F... 36162075
Jurkat IC50 = 55130.0 nM 4.26 Antiproliferative activity against human Jurkat T cells assessed as DNA content ... 29939742
PBMC IC50 = 74690.0 nM 4.13 Immunosuppressive activity against human PBMC assessed as inhibition of PHA-stim... 29939742

Literature References

PubMed DOI Target Context # Activities
36162075 10.1021/acs.jmedchem.2c00496 THP-1 4
29939742 10.1021/acs.jmedchem.8b00373 Jurkat 3
29939742 10.1021/acs.jmedchem.8b00373 No relevant target 3
29939742 10.1021/acs.jmedchem.8b00373 PBMC 2
36162075 10.1021/acs.jmedchem.2c00496 U-937 2
29939742 10.1021/acs.jmedchem.8b00373 Dihydroorotate dehydrogenase (quinone), mitochondrial 1
36162075 10.1021/acs.jmedchem.2c00496 Dihydroorotate dehydrogenase (quinone), mitochondrial 1
36162075 10.1021/acs.jmedchem.2c00496 No relevant target 1
36162075 10.1021/acs.jmedchem.2c00496 Jurkat 1
36162075 10.1021/acs.jmedchem.2c00496 MV4-11 1

Data from ChEMBL 36 via Core Engine