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Compound Detail

CHEMBL72165

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O=C1c2cc(Br)ccc2-n2c1nc1ccccc1c2=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL72165
Phase Preclinical
Structure Type MOL
InChI Key INPHXCCBDRGBRF-UHFFFAOYSA-N
14
Targets
30
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

327.1
MW (Da)
2.69
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

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C15H7BrN2O2
MW 327.14
Aromatic Rings 3
Heavy Atoms 20
NP-Likeness -0.16

Activity Summary

IC50 25 meas. best 7.28
Ki 5 meas. best 6.45

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Tryptophan 2,3-dioxygenase
CHEMBL2140
 IC50 7.28 6.86 53.0 3
Indoleamine 2,3-dioxygenase 1
CHEMBL4685
 IC50 7.27 6.5833 53.9 3
Tryptophan 2,3-dioxygenase
CHEMBL2140
 Ki 6.45 6.45 356.0 1
Indoleamine 2,3-dioxygenase 1
CHEMBL4685
 Ki 6.41 6.41 389.0 2
HL-60
CHEMBL383
 IC50 5.7 5.7 2000.0 1
Hep 3B2
CHEMBL4296437
 IC50 5.7 5.7 2000.0 1
Indoleamine 2,3-dioxygenase 2
CHEMBL3627587
 IC50 5.5 5.2875 3200.0 4
K562
CHEMBL385
 IC50 5.3 5.3 5000.0 1
Indoleamine 2,3-dioxygenase 2
CHEMBL3627587
 Ki 5.25 5.25 5600.0 2
MOLT-4
CHEMBL614177
 IC50 5.1 5.1 8000.0 1
T-24
CHEMBL614774
 IC50 4.82 4.425 15070.0 2
Bel-7402
CHEMBL614279
 IC50 4.57 4.57 27160.0 1
L02
CHEMBL4296457
 IC50 4.3 4.3 50110.0 2
MGC-803
CHEMBL3706566
 IC50 4.23 4.23 59060.0 1
SK-OV-3
CHEMBL614925
 IC50 4.05 4.05 89640.0 1
HepG2
CHEMBL395
 IC50 4.05 4.025 89640.0 2
A549
CHEMBL392
 IC50 4.05 4.05 89640.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Tryptophan 2,3-dioxygenase IC50 = 53.0 nM 7.28 Inhibition of TDO (unknown origin) expressed in HEK293 cells using L-Trp as subs... 30321802
Indoleamine 2,3-dioxygenase 1 IC50 = 53.9 nM 7.27 Inhibition of human IDO1 expressed in HEK293 cells assessed as kynurenine releas... 24099220
Tryptophan 2,3-dioxygenase IC50 = 54.0 nM 7.27 Inhibition of TDO in human U87 MG cells using L-Trp as substrate after 8 hrs 30321802
Tryptophan 2,3-dioxygenase Ki = 356.0 nM 6.45 Uncompetitive inhibition of recombinant full length C-terminal His-tagged human ... 30321802
Indoleamine 2,3-dioxygenase 1 Ki = 389.0 nM 6.41 Uncompetitive inhibition of IDO1 (unknown origin) using L-tryptophan as substrat... -
Indoleamine 2,3-dioxygenase 1 Ki = 389.0 nM 6.41 Uncompetitive inhibition of human recombinant IDO1 using L-tryptophan as substra... 24099220
Indoleamine 2,3-dioxygenase 1 IC50 = 574.0 nM 6.24 Uncompetitive inhibition of human recombinant IDO1 using L-tryptophan as substra... 24099220
Indoleamine 2,3-dioxygenase 1 IC50 = 574.0 nM 6.24 Inhibition of IDO1 (unknown origin) using L-tryptophan as substrate assessed as ... -
Tryptophan 2,3-dioxygenase IC50 = 937.0 nM 6.03 Inhibition of recombinant full length C-terminal His-tagged human TDO expressed ... 30321802
Hep 3B2 IC50 = 2000.0 nM 5.7 Antiproliferative activity against human Hep3B cells measured after 48 hrs by MT... 38665827
HL-60 IC50 = 2000.0 nM 5.7 Anticancer activity against human HL-60 cells measured after 48 hrs 38665827
Indoleamine 2,3-dioxygenase 2 IC50 = 3200.0 nM 5.5 Inhibition of recombinant human IDO2 expressed in human U87MG cells assessed as ... 27475108
Indoleamine 2,3-dioxygenase 2 IC50 = 3220.0 nM 5.49 Inhibition of IDO2 (unknown origin) expressed in human U87MG cells in presence o... -
K562 IC50 = 5000.0 nM 5.3 Anticancer activity against human K562 cells measured after 48 hrs 38665827
Indoleamine 2,3-dioxygenase 2 Ki = 5620.0 nM 5.25 Uncompetitive inhibition of human IDO2 using L-tryptophan as substrate incubated... -
Indoleamine 2,3-dioxygenase 2 Ki = 5600.0 nM 5.25 Uncompetitive inhibition of recombinant human C-terminal His6-tagged IDO2 (14-42... 27475108
MOLT-4 IC50 = 8000.0 nM 5.1 Anticancer activity against human MOLT-4 cells measured after 48 hrs 38665827
Indoleamine 2,3-dioxygenase 2 IC50 = 8260.0 nM 5.08 Inhibition of human IDO2 using L-tryptophan as substrate assessed as reduction i... -
Indoleamine 2,3-dioxygenase 2 IC50 = 8300.0 nM 5.08 Inhibition of recombinant human C-terminal His6-tagged IDO2 (14-420 residues) ex... 27475108
T-24 IC50 = 15070.0 nM 4.82 Antiproliferative activity against human T24 cells measured after 48 hrs by MTT ... 38665827

Literature References

PubMed DOI Target Context # Activities
27475108 10.1016/j.ejmech.2016.07.013 Indoleamine 2,3-dioxygenase 2 7
30321802 10.1016/j.ejmech.2018.10.017 Tryptophan 2,3-dioxygenase 4
24099220 10.1021/jm401195n Indoleamine 2,3-dioxygenase 1 3
23360475 10.1021/np3007167 Mycobacterium tuberculosis 3
23360475 10.1021/np3007167 Caco-2 3
23360475 10.1021/np3007167 No relevant target 3
18824607 10.1128/aac.00903-08 ADMET 2
38665827 10.1039/d3md00698k HepG2 2
38665827 10.1039/d3md00698k L02 2
38665827 10.1039/d3md00698k SK-OV-3 2
20373766 10.1021/jm901847f Escherichia coli 2
38665827 10.1039/d3md00698k T-24 2
18824607 10.1128/aac.00903-08 Toxoplasma gondii 1
23321561 10.1016/j.bmcl.2012.12.024 ADMET 1
23321561 10.1016/j.bmcl.2012.12.024 HFF 1
23321561 10.1016/j.bmcl.2012.12.024 Toxoplasma gondii 1
12161121 10.1016/s0960-894x(02)00431-6 DU-145 1
12161121 10.1016/s0960-894x(02)00431-6 SK-OV-3 1
12161121 10.1016/s0960-894x(02)00431-6 M14 1
38665827 10.1039/d3md00698k HeLa 1

Data from ChEMBL 36 via Core Engine