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Compound Detail

CHEMBL1276265

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O=C1c2ccc(Cl)cc2-n2c1nc1ccccc1c2=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1276265
Phase Preclinical
Structure Type MOL
InChI Key KHONZILMMZKIQL-UHFFFAOYSA-N
3
Targets
16
Activities
2
Assay Types
0
PK Parameters
14
Publications
0
Known Names

Molecular Properties

282.7
MW (Da)
2.58
ALogP
4
HBA
0
HBD
52.0
PSA (Ų)
0.50
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C15H7ClN2O2
MW 282.69
Aromatic Rings 3
Heavy Atoms 20
NP-Likeness -0.24

Activity Summary

IC50 11 meas. best 6.74
Ki 5 meas. best 4.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Indoleamine 2,3-dioxygenase 1
CHEMBL4685
 IC50 6.74 5.435 183.0 4
Tryptophan 2,3-dioxygenase
CHEMBL2140
 IC50 6.13 6.075 733.0 2
Indoleamine 2,3-dioxygenase 2
CHEMBL3627587
 IC50 4.74 4.455 18370.0 4
Indoleamine 2,3-dioxygenase 2
CHEMBL3627587
 Ki 4.4 4.4 39460.0 2
Tryptophan 2,3-dioxygenase
CHEMBL2140
 Ki 4.37 4.37 42700.0 1
Indoleamine 2,3-dioxygenase 1
CHEMBL4685
 Ki 4.31 4.31 49370.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Indoleamine 2,3-dioxygenase 1 IC50 = 183.0 nM 6.74 Inhibition of human IDO1 expressed in HEK293 cells assessed as kynurenine releas... 24099220
Indoleamine 2,3-dioxygenase 1 IC50 = 183.0 nM 6.74 Inhibition of IDO1 in human U87MG cells in presence of L-tryptophan incubated fo... -
Tryptophan 2,3-dioxygenase IC50 = 733.0 nM 6.13 Inhibition of TDO (unknown origin) expressed in HEK293 cells using L-Trp as subs... 30321802
Tryptophan 2,3-dioxygenase IC50 = 957.0 nM 6.02 Inhibition of TDO in human U87 MG cells using L-Trp as substrate after 8 hrs 30321802
Indoleamine 2,3-dioxygenase 2 IC50 = 18400.0 nM 4.74 Inhibition of recombinant human IDO2 expressed in human U87MG cells assessed as ... 27475108
Indoleamine 2,3-dioxygenase 2 IC50 = 18370.0 nM 4.74 Inhibition of IDO2 (unknown origin) expressed in human U87MG cells in presence o... -
Indoleamine 2,3-dioxygenase 2 Ki = 39500.0 nM 4.4 Uncompetitive inhibition of recombinant human C-terminal His6-tagged IDO2 (14-42... 27475108
Indoleamine 2,3-dioxygenase 2 Ki = 39460.0 nM 4.4 Uncompetitive inhibition of human IDO2 using L-tryptophan as substrate incubated... -
Tryptophan 2,3-dioxygenase Ki = 42700.0 nM 4.37 Mixed type uncompetitive inhibition of recombinant full length C-terminal His-ta... 30321802
Indoleamine 2,3-dioxygenase 1 Ki = 49370.0 nM 4.31 Uncompetitive inhibition of human recombinant IDO1 using L-tryptophan as substra... 24099220
Indoleamine 2,3-dioxygenase 1 Ki = 49370.0 nM 4.31 Uncompetitive inhibition of IDO1 (unknown origin) using L-tryptophan as substrat... -
Indoleamine 2,3-dioxygenase 2 IC50 = 67900.0 nM 4.17 Inhibition of recombinant human C-terminal His6-tagged IDO2 (14-420 residues) ex... 27475108
Indoleamine 2,3-dioxygenase 2 IC50 = 67900.0 nM 4.17 Inhibition of human IDO2 using L-tryptophan as substrate assessed as reduction i... -
Indoleamine 2,3-dioxygenase 1 IC50 = 74370.0 nM 4.13 Uncompetitive inhibition of human recombinant IDO1 using L-tryptophan as substra... 24099220
Indoleamine 2,3-dioxygenase 1 IC50 = 74370.0 nM 4.13 Inhibition of IDO1 (unknown origin) using L-tryptophan as substrate assessed as ... -

Literature References

PubMed DOI Target Context # Activities
27475108 10.1016/j.ejmech.2016.07.013 Indoleamine 2,3-dioxygenase 2 5
23360475 10.1021/np3007167 No relevant target 4
23360475 10.1021/np3007167 Mycobacterium tuberculosis 4
30321802 10.1016/j.ejmech.2018.10.017 Tryptophan 2,3-dioxygenase 4
24099220 10.1021/jm401195n Indoleamine 2,3-dioxygenase 1 3
18824607 10.1128/aac.00903-08 ADMET 2
23360475 10.1021/np3007167 Caco-2 2
18824607 10.1128/aac.00903-08 Toxoplasma gondii 1
23360475 10.1021/np3007167 Liver microsomes 1
23360475 10.1021/np3007167 Plasma 1
23360475 10.1021/np3007167 Cytochrome P450 3A4 1
23360475 10.1021/np3007167 Cytochrome P450 2C19 1
23360475 10.1021/np3007167 Cytochrome P450 2C9 1
23360475 10.1021/np3007167 Vero 1

Data from ChEMBL 36 via Core Engine