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Compound Detail

CHEMBL312537

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Cc1ccc2c(c1)C(=O)c1nc3ccccc3c(=O)n1-2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL312537
Phase Preclinical
Structure Type MOL
InChI Key DSZRZFCUYHAAAE-UHFFFAOYSA-N
3
Targets
15
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

262.3
MW (Da)
2.24
ALogP
4
HBA
0
HBD
52.0
PSA (Ų)
0.49
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 C16H10N2O2
MW 262.27
Aromatic Rings 3
Heavy Atoms 20
NP-Likeness -0.13

Activity Summary

IC50 10 meas. best 6.74
Ki 5 meas. best 6.08

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Tryptophan 2,3-dioxygenase
CHEMBL2140
 IC50 6.74 6.3 184.0 3
Tryptophan 2,3-dioxygenase
CHEMBL2140
 Ki 6.08 6.08 834.0 1
Hep 3B2
CHEMBL4296437
 IC50 5.19 5.19 6500.0 1
Indoleamine 2,3-dioxygenase 2
CHEMBL3627587
 IC50 4.66 4.58 21800.0 4
Indoleamine 2,3-dioxygenase 2
CHEMBL3627587
 Ki 4.46 4.46 34600.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Tryptophan 2,3-dioxygenase IC50 = 184.0 nM 6.74 Inhibition of TDO in human U87 MG cells using L-Trp as substrate after 8 hrs 30321802
Tryptophan 2,3-dioxygenase IC50 = 215.0 nM 6.67 Inhibition of TDO (unknown origin) expressed in HEK293 cells using L-Trp as subs... 30321802
Tryptophan 2,3-dioxygenase Ki = 834.0 nM 6.08 Mixed type uncompetitive inhibition of recombinant full length C-terminal His-ta... 30321802
Tryptophan 2,3-dioxygenase IC50 = 3230.0 nM 5.49 Inhibition of recombinant full length C-terminal His-tagged human TDO expressed ... 30321802
Hep 3B2 IC50 = 6500.0 nM 5.19 Anticancer activity against human Hep3B cells measured after 48 hrs 38665827
Indoleamine 2,3-dioxygenase 2 IC50 = 21800.0 nM 4.66 Inhibition of recombinant human IDO2 expressed in human U87MG cells assessed as ... 27475108
Indoleamine 2,3-dioxygenase 2 IC50 = 21810.0 nM 4.66 Inhibition of IDO2 (unknown origin) expressed in human U87MG cells in presence o... -
Indoleamine 2,3-dioxygenase 2 IC50 = 32000.0 nM 4.5 Inhibition of recombinant human C-terminal His6-tagged IDO2 (14-420 residues) ex... 27475108
Indoleamine 2,3-dioxygenase 2 IC50 = 31950.0 nM 4.5 Inhibition of human IDO2 using L-tryptophan as substrate assessed as reduction i... -
Indoleamine 2,3-dioxygenase 2 Ki = 34600.0 nM 4.46 Non-competitive inhibition of recombinant human C-terminal His6-tagged IDO2 (14-... 27475108
Indoleamine 2,3-dioxygenase 2 Ki = 34630.0 nM 4.46 Noncompetitive inhibition of human IDO2 using L-tryptophan as substrate incubate... -

Literature References

PubMed DOI Target Context # Activities
24885014 10.1021/np500108r Unchecked 29
30321802 10.1016/j.ejmech.2018.10.017 Tryptophan 2,3-dioxygenase 4
27475108 10.1016/j.ejmech.2016.07.013 Indoleamine 2,3-dioxygenase 2 4
24099220 10.1021/jm401195n Indoleamine 2,3-dioxygenase 1 3
18824607 10.1128/aac.00903-08 ADMET 2
24885014 10.1021/np500108r Molecular identity unknown 2
38665827 10.1039/d3md00698k A498 1
12161121 10.1016/s0960-894x(02)00431-6 NCI/ADR-RES 1
38665827 10.1039/d3md00698k NCI/ADR-RES 1
38665827 10.1039/d3md00698k Hep 3B2 1
30321802 10.1016/j.ejmech.2018.10.017 Unchecked 1
28720329 10.1016/j.bmc.2017.07.003 Staphylococcus aureus 1
28720329 10.1016/j.bmc.2017.07.003 Malassezia furfur 1
18824607 10.1128/aac.00903-08 Toxoplasma gondii 1
12161121 10.1016/s0960-894x(02)00431-6 A498 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
12161121 10.1016/s0960-894x(02)00431-6 NCI-H522 1
12161121 10.1016/s0960-894x(02)00431-6 SW-620 1

Data from ChEMBL 36 via Core Engine