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Compound Detail

CHEMBL5193821

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CCn1c(CO)nn(-c2nc(O[C@@H](C)C(F)(F)F)c(C(=O)Nc3c(C)cnc(OC)c3Cl)cc2F)c1=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL5193821
Phase Preclinical
Structure Type MOL
InChI Key FJYNLQXYLQBCRQ-JTQLQIEISA-N
6
Targets
10
Activities
2
Assay Types
23
PK Parameters
18
Publications
0
Known Names

Molecular Properties

548.9
MW (Da)
3.03
ALogP
10
HBA
2
HBD
133.4
PSA (Ų)
0.41
QED
1
Ro5 Violations
8
Rot. Bonds

Drug Information

Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H21ClF4N6O5
MW 548.88
Aromatic Rings 3
Heavy Atoms 37
NP-Likeness -1.11

Activity Summary

IC50 9 meas. best 9.52
Kd 1 meas. best 8.96

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Dihydroorotate dehydrogenase (quinone), mitochondrial
CHEMBL1966
 IC50 9.52 9.52 0.3 2
MOLM-13
CHEMBL3706572
 IC50 9.4 9.4 0.4 2
Unchecked
CHEMBL612545
 IC50 9.27 8.825 0.5 2
Dihydroorotate dehydrogenase (quinone), mitochondrial
CHEMBL1966
 Kd 8.96 8.96 1.1 1
THP-1
CHEMBL614245
 IC50 8.85 8.85 1.4 1
Dihydroorotate dehydrogenase (quinone), mitochondrial
CHEMBL2991
 IC50 8.0 8.0 10.0 1
Dihydroorotate dehydrogenase (quinone), mitochondrial
CHEMBL2383
 IC50 6.89 6.89 130.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 23807.0 ng.hr.mL-1 Rattus norvegicus
AUC 25046.0 ng.hr.mL-1 Mus musculus
CL 7700.0 mL.min-1.g-1 Homo sapiens
CL 5.5 mL.min-1.kg-1 Mus musculus
CL 6.2 mL.min-1.kg-1 Rattus norvegicus
CL 86.0 mL.min-1.kg-1 Canis lupus familiaris
CL 5.3 mL.min-1.kg-1 Macaca mulatta
CL 7.6 mL.min-1.kg-1 Rattus norvegicus
CL 7.3 mL.min-1.kg-1 Mus musculus
CL 7.7 mL.min-1.kg-1 Homo sapiens
Cmax 3995.41 nM Rattus norvegicus
Cmax 6941.41 nM Mus musculus
F 106.0 % Rattus norvegicus
F 110.0 % Mus musculus
Fu 0.063 - Homo sapiens
Fu 0.062 - Mus musculus
Fu 0.078 - Rattus norvegicus
Fu 0.042 - Canis lupus familiaris
T1/2 0.65 hr Homo sapiens
T1/2 4.0 hr Rattus norvegicus
T1/2 5.0 hr Mus musculus
Tmax 4.0 hr Rattus norvegicus
Tmax 1.0 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Dihydroorotate dehydrogenase (quinone), mitochondrial IC50 = 0.3 nM 9.52 Inhibition of His fused human DHODH expressed in Escherichia coli using DHO as s... 35925768
Dihydroorotate dehydrogenase (quinone), mitochondrial IC50 = 0.3 nM 9.52 Inhibition of human DHODH in MOLM-13 AML cells 38505861
MOLM-13 IC50 = 0.4 nM 9.4 Antiproliferative activity against human MOLM-13 cells incubated for 72 hrs by C... 35925768
MOLM-13 IC50 = 0.4 nM 9.4 Antiproliferative activity in human MOLM-13 AML cells assessed as reduction in c... 38505861
Unchecked IC50 = 0.54 nM 9.27 Inhibition of monkey DHODH 35925768
Dihydroorotate dehydrogenase (quinone), mitochondrial Kd = 1.1 nM 8.96 Binding affinity to His fused human DHODH expressed in Escherichia coli by surfa... 35925768
THP-1 IC50 = 1.4 nM 8.85 Antiproliferative activity against human THP-1 cells assessed as reduction in ce... 35925768
Unchecked IC50 = 4.2 nM 8.38 Inhibition of dog DHODH 35925768
Dihydroorotate dehydrogenase (quinone), mitochondrial IC50 = 10.0 nM 8.0 Inhibition of mouse DHODH 35925768
Dihydroorotate dehydrogenase (quinone), mitochondrial IC50 = 130.0 nM 6.89 Inhibition of rat DHODH 35925768

Literature References

PubMed DOI Target Context # Activities
35925768 10.1021/acs.jmedchem.2c00788 ADMET 31
35925768 10.1021/acs.jmedchem.2c00788 Dihydroorotate dehydrogenase (quinone), mitochondrial 5
35925768 10.1021/acs.jmedchem.2c00788 MOLM-13 4
35925768 10.1021/acs.jmedchem.2c00788 No relevant target 2
35925768 10.1021/acs.jmedchem.2c00788 Unchecked 2
38505861 10.1021/acsmedchemlett.3c00543 ADMET 2
38505861 10.1021/acsmedchemlett.3c00543 No relevant target 1
38505861 10.1021/acsmedchemlett.3c00543 ATP-dependent translocase ABCB1 1
38505861 10.1021/acsmedchemlett.3c00543 MOLM-13 1
38505861 10.1021/acsmedchemlett.3c00543 Dihydroorotate dehydrogenase (quinone), mitochondrial 1
35925768 10.1021/acs.jmedchem.2c00788 Cytochrome P450 3A4 1
35925768 10.1021/acs.jmedchem.2c00788 Cytochrome P450 2D6 1
35925768 10.1021/acs.jmedchem.2c00788 Cytochrome P450 2C19 1
35925768 10.1021/acs.jmedchem.2c00788 Cytochrome P450 2C9 1
35925768 10.1021/acs.jmedchem.2c00788 Cytochrome P450 2C8 1
35925768 10.1021/acs.jmedchem.2c00788 Cytochrome P450 1A2 1
35925768 10.1021/acs.jmedchem.2c00788 Voltage-gated inwardly rectifying potassium channel KCNH2 1
35925768 10.1021/acs.jmedchem.2c00788 THP-1 1

Data from ChEMBL 36 via Core Engine