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Compound Detail

CHEMBL432537

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O=C1c2cc([N+](=O)[O-])ccc2-n2c1nc1ccccc1c2=O

Basic Information

ChEMBL ID CHEMBL432537
Phase Preclinical
Structure Type MOL
InChI Key UFMQJYHLIUACCG-UHFFFAOYSA-N
12
Targets
29
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

293.2
MW (Da)
1.84
ALogP
6
HBA
0
HBD
95.1
PSA (Ų)
0.39
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C15H7N3O4
MW 293.24
Aromatic Rings 3
Heavy Atoms 22
NP-Likeness -0.53

Activity Summary

IC50 22 meas. best 10.74
Ki 5 meas. best 7.27
EC50 2 meas. best 7.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Indoleamine 2,3-dioxygenase 1
CHEMBL4685
IC50 10.74 7.594 0.0 5
Tryptophan 2,3-dioxygenase
CHEMBL2140
IC50 7.4 7.2033 40.0 3
Indoleamine 2,3-dioxygenase 1
CHEMBL4685
Ki 7.27 7.27 54.0 2
Plasmodium falciparum
CHEMBL364
EC50 7.0 6.915 100.5 2
Tryptophan 2,3-dioxygenase
CHEMBL2140
Ki 6.67 6.67 215.0 1
HeLa
CHEMBL399
IC50 6.47 6.47 340.0 1
Indoleamine 2,3-dioxygenase 2
CHEMBL3627587
IC50 6.35 5.986 446.0 5
B16-F10
CHEMBL612656
IC50 6.31 6.31 490.0 1
LX-2
CHEMBL5465457
IC50 6.08 6.08 830.0 1
Indoleamine 2,3-dioxygenase 2
CHEMBL3627587
Ki 6.01 6.01 970.0 2
Hep 3B2
CHEMBL4296437
IC50 5.85 5.85 1400.0 1
A549
CHEMBL392
IC50 5.16 5.16 6880.0 1
HepG2
CHEMBL395
IC50 5.1 5.1 7890.0 1
K562
CHEMBL385
IC50 5.09 5.09 8050.0 1
PC-3
CHEMBL390
IC50 4.93 4.93 11830.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Indoleamine 2,3-dioxygenase 1 IC50 = 0.018 nM 10.74 Inhibition of human IDO1 expressed in HEK293 cells assessed as kynurenine releas... 24099220
Tryptophan 2,3-dioxygenase IC50 = 40.0 nM 7.4 Inhibition of TDO in human U87 MG cells using L-Trp as substrate after 8 hrs 30321802
Indoleamine 2,3-dioxygenase 1 Ki = 54.0 nM 7.27 Uncompetitive inhibition of human recombinant IDO1 using L-tryptophan as substra... 24099220
Indoleamine 2,3-dioxygenase 1 Ki = 54.0 nM 7.27 Uncompetitive inhibition of IDO1 (unknown origin) using L-tryptophan as substrat... -
Tryptophan 2,3-dioxygenase IC50 = 61.0 nM 7.21 Inhibition of TDO (unknown origin) expressed in HEK293 cells using L-Trp as subs... 30321802
Tryptophan 2,3-dioxygenase IC50 = 101.0 nM 7.0 Inhibition of recombinant full length C-terminal His-tagged human TDO expressed ... 30321802
Plasmodium falciparum EC50 = 100.5 nM 7.0 NOVARTIS: Inhibition of Plasmodium falciparum W2 (drug-resistant) proliferation ... 18579783
Indoleamine 2,3-dioxygenase 1 IC50 = 103.0 nM 6.99 Uncompetitive inhibition of human recombinant IDO1 using L-tryptophan as substra... 24099220
Indoleamine 2,3-dioxygenase 1 IC50 = 103.0 nM 6.99 Inhibition of IDO1 (unknown origin) using L-tryptophan as substrate assessed as ... -
Indoleamine 2,3-dioxygenase 1 IC50 = 103.0 nM 6.99 Inhibition of human IDO1 using L-tryptophan as substrate assessed as reduction i... 37866714
Plasmodium falciparum EC50 = 148.5 nM 6.83 NOVARTIS: Inhibition of Plasmodium falciparum 3D7 (drug-susceptible) proliferati... 18579783
Tryptophan 2,3-dioxygenase Ki = 215.0 nM 6.67 Uncompetitive inhibition of recombinant full length C-terminal His-tagged human ... 30321802
HeLa IC50 = 340.0 nM 6.47 Antiproliferative activity against human HeLa cells 38665827
Indoleamine 2,3-dioxygenase 2 IC50 = 446.0 nM 6.35 Inhibition of IDO2 (unknown origin) expressed in human U87MG cells in presence o... -
Indoleamine 2,3-dioxygenase 2 IC50 = 450.0 nM 6.35 Inhibition of recombinant human IDO2 expressed in human U87MG cells assessed as ... 27475108
B16-F10 IC50 = 490.0 nM 6.31 Antiproliferative activity against mouse B16-F10 cells 38665827
Indoleamine 2,3-dioxygenase 1 IC50 = 550.0 nM 6.26 Indoleamine-2,3-Dioxygenase 1 Inhibitory Activity: Experimental method: IDO-1 ca... -
LX-2 IC50 = 830.0 nM 6.08 Antiproliferative activity against human LX-2 cells 38665827
Indoleamine 2,3-dioxygenase 2 Ki = 970.0 nM 6.01 Uncompetitive inhibition of recombinant human C-terminal His6-tagged IDO2 (14-42... 27475108
Indoleamine 2,3-dioxygenase 2 Ki = 970.0 nM 6.01 Uncompetitive inhibition of human IDO2 using L-tryptophan as substrate incubated... -

Literature References

Data from ChEMBL 36 via Core Engine