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Compound Detail

CHEMBL355606

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Fc1ccc2c(/C=C/c3cccnc3)c[nH]c2c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL355606
Phase Preclinical
Structure Type MOL
InChI Key YBSDQTBCNYWBMX-ONEGZZNKSA-N
5
Targets
22
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

238.3
MW (Da)
3.87
ALogP
1
HBA
1
HBD
28.7
PSA (Ų)
0.72
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C15H11FN2
MW 238.26
Aromatic Rings 3
Heavy Atoms 18
NP-Likeness -0.81

Activity Summary

IC50 17 meas. best 7.3
Ki 5 meas. best 7.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Tryptophan 2,3-dioxygenase
CHEMBL2140
 Ki 7.52 6.79 30.0 2
Tryptophan 2,3-dioxygenase
CHEMBL2686
 Ki 7.52 7.52 30.0 1
Tryptophan 2,3-dioxygenase
CHEMBL2686
 IC50 7.3 7.3 50.0 1
Indoleamine 2,3-dioxygenase 1
CHEMBL4685
 Ki 7.29 7.29 51.0 1
Tryptophan 2,3-dioxygenase
CHEMBL2140
 IC50 6.96 6.3017 110.0 12
Unchecked
CHEMBL612545
 Ki 6.06 6.06 880.0 1
Tryptophan 2,3-dioxygenase
CHEMBL1075307
 IC50 6.0 5.92 1000.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Tryptophan 2,3-dioxygenase Ki = 30.0 nM 7.52 Inhibition of liver TDO 22626654
Tryptophan 2,3-dioxygenase Ki = 30.0 nM 7.52 Compound was tested for inhibition of Tryptophan dioxygenase (TDO) from rat live... -
Tryptophan 2,3-dioxygenase IC50 = 50.0 nM 7.3 Inhibition of TDO2 in rat liver homogenate assessed as reduction in N-formylkynu... 33901770
Indoleamine 2,3-dioxygenase 1 Ki = 51.0 nM 7.29 Binding affinity to IDO (unknown origin) assessed as inhibition constant 36917881
Tryptophan 2,3-dioxygenase IC50 = 110.0 nM 6.96 Inhibition of recombinant human TDO2 expressed in Escherichia coli BL21 (DE3) as... 33901770
Tryptophan 2,3-dioxygenase IC50 = 280.0 nM 6.55 Inhibition of human TDO 26207924
Tryptophan 2,3-dioxygenase IC50 = 280.0 nM 6.55 Inhibition of human recombinant pEF6/V5-His-tagged TDO2 transfected in HEK293-EB... 31580660
Tryptophan 2,3-dioxygenase IC50 = 280.0 nM 6.55 Inhibition of human TDO2 expressed in mouse P815B cells assessed as kynurenine c... 34338527
Tryptophan 2,3-dioxygenase IC50 = 310.0 nM 6.51 Inhibition of recombinant human TDO2 expressed in Escherichia coli BL21 (DE3) as... 33901770
Tryptophan 2,3-dioxygenase IC50 = 350.0 nM 6.46 Inhibition of TDO (unknown origin) assessed as reduction in N-formylkynurenine f... 35938398
Tryptophan 2,3-dioxygenase IC50 = 376.5 nM 6.42 Inhibition of recombinant human TDO using L-Trp as substrate after 75 mins by UV... 30103191
Tryptophan 2,3-dioxygenase IC50 = 410.0 nM 6.39 Inhibition of TDO (unknown origin) using L-Trp as substrate incubated for 75 min... 36370550
Tryptophan 2,3-dioxygenase IC50 = 492.0 nM 6.31 Inhibition of TDO (unknown origin) 36917881
Unchecked Ki = 880.0 nM 6.06 Inhibition of recombinant human TDO 34338527
Tryptophan 2,3-dioxygenase Ki = 880.0 nM 6.06 Competitive inhibition of human recombinant TDO expressed in Escherichia coli BL... 21726069
Tryptophan 2,3-dioxygenase IC50 = 937.0 nM 6.03 Inhibition of TDO (unknown origin) using L-tryptophan as substrate incubated for... 32247733
Tryptophan 2,3-dioxygenase IC50 = 1000.0 nM 6.0 Inhibition of mouse TDO expressed in mouse P815B cells assessed as inhibition of... 21726069
Tryptophan 2,3-dioxygenase IC50 = 1300.0 nM 5.89 Inhibition of human purified TDO assessed as formation of kynurenine from N-form... 22626654
Tryptophan 2,3-dioxygenase IC50 = 1460.0 nM 5.84 Inhibition of mouse TDO 26207924
Tryptophan 2,3-dioxygenase IC50 = 10000.0 nM 5.0 TDO Coupled Biochemical Assays: In two separate assays, 2.5 μg/μl of human TDO p... -

Literature References

PubMed DOI Target Context # Activities
33901770 10.1016/j.bmc.2021.116160 Tryptophan 2,3-dioxygenase 3
31580660 10.1021/acs.jmedchem.9b01079 Tryptophan 2,3-dioxygenase 2
34338527 10.1021/acs.jmedchem.1c00323 Indoleamine 2,3-dioxygenase 1 2
33901770 10.1016/j.bmc.2021.116160 Indoleamine 2,3-dioxygenase 1 2
- 10.6019/CHEMBL4513161 Pseudomonas aeruginosa 2
30103191 10.1016/j.ejmech.2018.08.013 Tryptophan 2,3-dioxygenase 2
26207924 10.1021/acs.jmedchem.5b00461 Tryptophan 2,3-dioxygenase 2
22626654 10.1016/j.ejmech.2012.04.033 Tryptophan 2,3-dioxygenase 2
21726069 10.1021/jm2006782 No relevant target 2
35938398 10.1021/acs.jmedchem.2c00677 Tryptophan 2,3-dioxygenase 2
21726069 10.1021/jm2006782 Tryptophan 2,3-dioxygenase 2
26207924 10.1021/acs.jmedchem.5b00461 Indoleamine 2,3-dioxygenase 1 1
30103191 10.1016/j.ejmech.2018.08.013 Unchecked 1
- 10.1016/0960-894X(96)00124-2 Tryptophan 2,3-dioxygenase 1
- 10.6019/CHEMBL4513161 Candida albicans 1
- 10.6019/CHEMBL4513161 Cryptococcus neoformans 1
- 10.6019/CHEMBL4513161 Escherichia coli 1
36370550 10.1016/j.ejmech.2022.114860 Tryptophan 2,3-dioxygenase 1
21726069 10.1021/jm2006782 Plasma 1
- 10.6019/CHEMBL4513161 Staphylococcus aureus 1

Data from ChEMBL 36 via Core Engine