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Compound Detail

CHEMBL4471895

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CN1CCN(c2ccc3nc4n(c(=O)c3c2)-c2ccccc2C4=O)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4471895
Phase Preclinical
Structure Type MOL
InChI Key XBHJNGFWXQBKPI-UHFFFAOYSA-N
3
Targets
9
Activities
2
Assay Types
0
PK Parameters
3
Publications
0
Known Names

Molecular Properties

346.4
MW (Da)
1.68
ALogP
6
HBA
0
HBD
58.4
PSA (Ų)
0.52
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C20H18N4O2
MW 346.39
Aromatic Rings 3
Heavy Atoms 26
NP-Likeness -0.56

Activity Summary

IC50 6 meas. best 6.33
Ki 3 meas. best 5.12

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Tryptophan 2,3-dioxygenase
CHEMBL2140
 IC50 6.33 5.75 470.0 2
Indoleamine 2,3-dioxygenase 1
CHEMBL4685
 IC50 5.53 5.315 2960.0 2
Indoleamine 2,3-dioxygenase 1
CHEMBL4685
 Ki 5.12 5.12 7570.0 1
Tryptophan 2,3-dioxygenase
CHEMBL2140
 Ki 4.75 4.75 17960.0 1
Indoleamine 2,3-dioxygenase 2
CHEMBL3627587
 IC50 4.31 4.195 48670.0 2
Indoleamine 2,3-dioxygenase 2
CHEMBL3627587
 Ki 4.31 4.31 48670.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Tryptophan 2,3-dioxygenase IC50 = 470.0 nM 6.33 Inhibition of human TDO transfected in HEK293 cells assessed as reduction in kyn... 31580660
Indoleamine 2,3-dioxygenase 1 IC50 = 2960.0 nM 5.53 Inhibition of IDO1 in IFN-gamma stimulated human HeLa cells assessed as reductio... 31580660
Tryptophan 2,3-dioxygenase IC50 = 6750.0 nM 5.17 Inhibition of recombinant human TDO expressed in Escherichia coli BL21 (DE3) ass... 31580660
Indoleamine 2,3-dioxygenase 1 Ki = 7570.0 nM 5.12 Uncompetitive inhibition of recombinant human IDO1 expressed in Escherichia coli... 31580660
Indoleamine 2,3-dioxygenase 1 IC50 = 8010.0 nM 5.1 Inhibition of recombinant human IDO1 expressed in Escherichia coli BL21 cells as... 31580660
Tryptophan 2,3-dioxygenase Ki = 17960.0 nM 4.75 Uncompetitive inhibition of recombinant human TDO expressed in Escherichia coli ... 31580660
Indoleamine 2,3-dioxygenase 2 IC50 = 48670.0 nM 4.31 Inhibition of human IDO2 transfected in human U87MG cells assessed as reduction ... 31580660
Indoleamine 2,3-dioxygenase 2 Ki = 48670.0 nM 4.31 Uncompetitive inhibition of C-terminal His6-tagged human IDO2 (14 to 420 residue... 31580660
Indoleamine 2,3-dioxygenase 2 IC50 = 82570.0 nM 4.08 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