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Compound Detail

CHEMBL4588805

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O=C1c2cc(F)ccc2-n2c1nc1ccc(CN3CCOCC3)cc1c2=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4588805
Phase Preclinical
Structure Type MOL
InChI Key QAUBWRHYUIABRL-UHFFFAOYSA-N
3
Targets
9
Activities
2
Assay Types
0
PK Parameters
3
Publications
0
Known Names

Molecular Properties

365.4
MW (Da)
1.90
ALogP
6
HBA
0
HBD
64.4
PSA (Ų)
0.54
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C20H16FN3O3
MW 365.36
Aromatic Rings 3
Heavy Atoms 27
NP-Likeness -1.02

Activity Summary

IC50 6 meas. best 7.7
Ki 3 meas. best 6.47

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Indoleamine 2,3-dioxygenase 1
CHEMBL4685
 IC50 7.7 7.05 20.0 2
Tryptophan 2,3-dioxygenase
CHEMBL2140
 IC50 7.16 6.61 70.0 2
Tryptophan 2,3-dioxygenase
CHEMBL2140
 Ki 6.47 6.47 340.0 1
Indoleamine 2,3-dioxygenase 1
CHEMBL4685
 Ki 6.33 6.33 470.0 1
Indoleamine 2,3-dioxygenase 2
CHEMBL3627587
 IC50 4.78 4.59 16540.0 2
Indoleamine 2,3-dioxygenase 2
CHEMBL3627587
 Ki 4.76 4.76 17540.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Indoleamine 2,3-dioxygenase 1 IC50 = 20.0 nM 7.7 Inhibition of IDO1 in IFN-gamma stimulated human HeLa cells assessed as reductio... 31580660
Tryptophan 2,3-dioxygenase IC50 = 70.0 nM 7.16 Inhibition of human TDO transfected in HEK293 cells assessed as reduction in kyn... 31580660
Tryptophan 2,3-dioxygenase Ki = 340.0 nM 6.47 Uncompetitive inhibition of recombinant human TDO expressed in Escherichia coli ... 31580660
Indoleamine 2,3-dioxygenase 1 IC50 = 400.0 nM 6.4 Inhibition of recombinant human IDO1 expressed in Escherichia coli BL21 cells as... 31580660
Indoleamine 2,3-dioxygenase 1 Ki = 470.0 nM 6.33 Uncompetitive inhibition of recombinant human IDO1 expressed in Escherichia coli... 31580660
Tryptophan 2,3-dioxygenase IC50 = 870.0 nM 6.06 Inhibition of recombinant human TDO expressed in Escherichia coli BL21 (DE3) ass... 31580660
Indoleamine 2,3-dioxygenase 2 IC50 = 16540.0 nM 4.78 Inhibition of human IDO2 transfected in human U87MG cells assessed as reduction ... 31580660
Indoleamine 2,3-dioxygenase 2 Ki = 17540.0 nM 4.76 Uncompetitive inhibition of C-terminal His6-tagged human IDO2 (14 to 420 residue... 31580660
Indoleamine 2,3-dioxygenase 2 IC50 = 39550.0 nM 4.4 Inhibition of C-terminal His6-tagged human IDO2 (14 to 420 residues) expressed i... 31580660

Literature References

PubMed DOI Target Context # Activities
31580660 10.1021/acs.jmedchem.9b01079 Indoleamine 2,3-dioxygenase 1 3
31580660 10.1021/acs.jmedchem.9b01079 Indoleamine 2,3-dioxygenase 2 3
31580660 10.1021/acs.jmedchem.9b01079 Tryptophan 2,3-dioxygenase 3

Data from ChEMBL 36 via Core Engine