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Compound Detail

CHEMBL4161733

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C[C@@H](C(=O)Nc1ccc(Cl)cc1)[C@H]1CC[C@@H](c2ccnc3ccc(F)cc32)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4161733
Phase Preclinical
Structure Type MOL
InChI Key KRTIYQIPSAGSBP-ZACQAIPSSA-N
7
Targets
29
Activities
3
Assay Types
12
PK Parameters
20
Publications
0
Known Names

Molecular Properties

410.9
MW (Da)
6.58
ALogP
2
HBA
1
HBD
42.0
PSA (Ų)
0.53
QED
1
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C24H24ClFN2O
MW 410.92
Aromatic Rings 3
Heavy Atoms 29
NP-Likeness -1.14

Activity Summary

IC50 27 meas. best 9.3
EC50 1 meas. best 8.7
Kd 1 meas. best 6.33

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Indoleamine 2,3-dioxygenase 1
CHEMBL4685
 IC50 9.3 8.3788 0.5 16
Unchecked
CHEMBL612545
 EC50 8.7 8.7 2.0 1
Indoleamine 2,3-dioxygenase 1
CHEMBL1075294
 IC50 8.3 8.3 5.0 2
Indoleamine 2,3-dioxygenase 1
CHEMBL4685
 Kd 6.33 6.33 470.0 1
Cytochrome P450 2C9
CHEMBL3397
 IC50 6.14 6.14 730.0 1
Cytochrome P450 2C8
CHEMBL3721
 IC50 5.7 5.7 2000.0 1
Tryptophan 2,3-dioxygenase
CHEMBL2140
 IC50 5.41 5.41 3900.0 1
Cytochrome P450 3A4
CHEMBL340
 IC50 5.29 5.29 5100.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 3821.56 ng.hr.mL-1 Mus musculus
AUC 3821.56 ng.hr.mL-1 Mus musculus
AUC 14341.11 ng.hr.mL-1 Mus musculus
AUC 14341.11 ng.hr.mL-1 Mus musculus
AUC 7396.56 ng.hr.mL-1 Mus musculus
CL 385.7 mL.min-1.g-1 Mus musculus
CL 21.3 mL.min-1.g-1 Homo sapiens
Cmax 2000.0 nM Mus musculus
Cmax 2000.0 nM Mus musculus
T1/2 2.55 hr Homo sapiens
T1/2 2.5 hr Mus musculus
T1/2 2.5 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Indoleamine 2,3-dioxygenase 1 IC50 = 0.5 nM 9.3 Inhibition of IDO1 (unknown origin) by cell-based assay 31580660
Indoleamine 2,3-dioxygenase 1 IC50 = 0.5 nM 9.3 Inhibition of IDO1 in human HeLa cells preincubated for 1 hr followed by IFN-gam... 33215494
Indoleamine 2,3-dioxygenase 1 IC50 = 0.5 nM 9.3 Inhibition of IDO1 in IFN-gamma stimulated human HeLa cells in presence of heme ... 34752953
Indoleamine 2,3-dioxygenase 1 IC50 = 1.7 nM 8.77 Inhibition of human IDO1 assessed as reduction in kynurenine production 29220788
Indoleamine 2,3-dioxygenase 1 IC50 = 1.7 nM 8.77 Inhibition of human IDO1 34110158
Indoleamine 2,3-dioxygenase 1 IC50 = 1.7 nM 8.77 Inhibition of human IDO1 using L-tryptophan as substrate assessed as reduction i... 37866714
Indoleamine 2,3-dioxygenase 1 IC50 = 2.0 nM 8.7 Inhibition of IDO1 in IFNgamma-stimulated human HeLa cells preincubated for 2 hr... 33603977
Indoleamine 2,3-dioxygenase 1 IC50 = 2.0 nM 8.7 Inhibition of IDO1 in recombinant IFN-gamma induced human HeLa cells incubated f... 33738077
Unchecked EC50 = 2.0 nM 8.7 Induction of proliferation of human T eff cells by T cell/DC mixed lymphocyte re... 33738077
Indoleamine 2,3-dioxygenase 1 IC50 = 2.8 nM 8.55 Inhibition of IDO1 in IFN-gamma stimulated human HeLa cells using L-tryptophan a... 32832022
Indoleamine 2,3-dioxygenase 1 IC50 = 3.4 nM 8.47 Inhibition of IDO1 in human SKOV3 assessed as reduction in kynurenine production 29220788
Indoleamine 2,3-dioxygenase 1 IC50 = 4.2 nM 8.38 Inhibition of IDO1 in human SKOV3 cells 33333163
Indoleamine 2,3-dioxygenase 1 IC50 = 4.2 nM 8.38 Inhibition of IDO1 in human SKOV3 cells 33316404
Indoleamine 2,3-dioxygenase 1 IC50 = 5.0 nM 8.3 Inhibition of IDO1 in IFNgamma-stimulated mouse M109 cells preincubated for 2 hr... 33603977
Indoleamine 2,3-dioxygenase 1 IC50 = 5.0 nM 8.3 Inhibition of IDO1 in recombinant IFN-gamma induced mouse M109 cells incubated f... 33738077
Indoleamine 2,3-dioxygenase 1 IC50 = 9.0 nM 8.05 Inhibition of IDO1 in IFNgamma/LPS-stimulated human whole blood preincubated for... 33603977
Indoleamine 2,3-dioxygenase 1 IC50 = 47.0 nM 7.33 Inhibition of IDO1 in human whole blood 33316404
Indoleamine 2,3-dioxygenase 1 IC50 = 47.0 nM 7.33 Inhibition of IDO1 in human whole blood 33333163
Indoleamine 2,3-dioxygenase 1 Kd = 470.0 nM 6.33 Binding affinity to IDO1 (unknown origin) assessed as dissociation constant by b... 36410047
Cytochrome P450 2C9 IC50 = 730.0 nM 6.14 Inhibition of CYP2C9 (unknown origin) 33333163

Literature References

PubMed DOI Target Context # Activities
33333163 10.1016/j.bmcl.2020.127744 ADMET 7
36410047 10.1021/acs.jmedchem.2c00771 Protein cereblon/Indoleamine 2,3-dioxygenase 1 7
33316404 10.1016/j.bmcl.2020.127738 ADMET 5
33738077 10.1021/acsmedchemlett.1c00014 ADMET 4
33603977 10.1021/acsmedchemlett.0c00668 Indoleamine 2,3-dioxygenase 1 4
33603977 10.1021/acsmedchemlett.0c00668 ADMET 3
33333163 10.1016/j.bmcl.2020.127744 Indoleamine 2,3-dioxygenase 1 3
33316404 10.1016/j.bmcl.2020.127738 Indoleamine 2,3-dioxygenase 1 3
34267885 10.1021/acsmedchemlett.1c00236 ADMET 3
33341650 10.1016/j.ejmech.2020.113071 Indoleamine 2,3-dioxygenase 1 2
33738077 10.1021/acsmedchemlett.1c00014 Indoleamine 2,3-dioxygenase 1 2
33738077 10.1021/acsmedchemlett.1c00014 Unchecked 2
29220788 10.1016/j.ejmech.2017.11.088 Indoleamine 2,3-dioxygenase 1 2
36410047 10.1021/acs.jmedchem.2c00771 Indoleamine 2,3-dioxygenase 1 2
31580660 10.1021/acs.jmedchem.9b01079 Indoleamine 2,3-dioxygenase 1 2
32055299 10.1039/C9MD00208A Homo sapiens 2
33333163 10.1016/j.bmcl.2020.127744 Cytochrome P450 2C8 1
33333163 10.1016/j.bmcl.2020.127744 Cytochrome P450 2C9 1
32247733 10.1016/j.bmcl.2020.127159 Indoleamine 2,3-dioxygenase 1 1
32055299 10.1039/C9MD00208A Indoleamine 2,3-dioxygenase 1 1

Data from ChEMBL 36 via Core Engine