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Compound Detail

CHEMBL1812545

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Fc1ccc2c(/C=C/c3nnn[nH]3)c[nH]c2c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1812545
Phase Preclinical
Structure Type MOL
InChI Key JDBSZVDIUIRSDG-DAFODLJHSA-N
2
Targets
21
Activities
2
Assay Types
1
PK Parameters
20
Publications
0
Known Names

Molecular Properties

229.2
MW (Da)
1.99
ALogP
3
HBA
2
HBD
70.2
PSA (Ų)
0.71
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 C11H8FN5
MW 229.22
Aromatic Rings 3
Heavy Atoms 17
NP-Likeness -1.31

Activity Summary

IC50 17 meas. best 6.52
Ki 4 meas. best 5.26

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Tryptophan 2,3-dioxygenase
CHEMBL2140
 IC50 6.52 5.6071 300.0 14
Tryptophan 2,3-dioxygenase
CHEMBL1075307
 IC50 5.71 5.3933 1960.0 3
Tryptophan 2,3-dioxygenase
CHEMBL2140
 Ki 5.26 5.2225 5500.0 4

Pharmacokinetic Data

Parameter Value Units Species
T1/2 24.0 hr Not specified

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Tryptophan 2,3-dioxygenase IC50 = 300.0 nM 6.52 Inhibition of full length N-terminal/C-terminal his-tagged human TDO expressed i... 39106326
Tryptophan 2,3-dioxygenase IC50 = 398.0 nM 6.4 Inhibition of TDO (unknown origin) expressed in HEK293 cells using L-Trp as subs... 30321802
Tryptophan 2,3-dioxygenase IC50 = 620.0 nM 6.21 Inhibition of human TDO 26207924
Tryptophan 2,3-dioxygenase IC50 = 620.0 nM 6.21 Inhibition of human recombinant pEF6/V5-His-tagged TDO2 transfected in HEK293-EB... 31580660
Tryptophan 2,3-dioxygenase IC50 = 671.0 nM 6.17 Inhibition of TDO in human U87 MG cells using L-Trp as substrate after 8 hrs 30321802
Tryptophan 2,3-dioxygenase IC50 = 1240.0 nM 5.91 Inhibition of human TDO transfected in HEK293T cells using L-tryptophan as subst... 39276584
Tryptophan 2,3-dioxygenase IC50 = 1740.0 nM 5.76 Inhibition of human TDO2 expressed in mouse P815B cells assessed as kynurenine c... 34338527
Tryptophan 2,3-dioxygenase IC50 = 1960.0 nM 5.71 Inhibition of mouse TDO 26207924
Tryptophan 2,3-dioxygenase IC50 = 2000.0 nM 5.7 Inhibition of mouse TDO expressed in mouse P815B cells assessed as inhibition of... 21726069
Tryptophan 2,3-dioxygenase IC50 = 2000.0 nM 5.7 Inhibition of human TDO 35952399
Tryptophan 2,3-dioxygenase Ki = 5500.0 nM 5.26 Inhibition of TDO (unknown origin) 30773421
Tryptophan 2,3-dioxygenase Ki = 5600.0 nM 5.25 Inhibition of recombinant human TDO expressed in Escherichia coli using L-Trp as... 30321802
Tryptophan 2,3-dioxygenase Ki = 5600.0 nM 5.25 Competitive inhibition of human recombinant TDO expressed in Escherichia coli BL... 21726069
Tryptophan 2,3-dioxygenase IC50 = 6100.0 nM 5.21 Inhibition of recombinant human TDO2 expressed in Escherichia coli BL21 (DE3) as... 34338527
Tryptophan 2,3-dioxygenase Ki = 7470.0 nM 5.13 Uncompetitive inhibition of recombinant full length C-terminal His-tagged human ... 30321802
Tryptophan 2,3-dioxygenase IC50 = 7943.0 nM 5.1 TDO Coupled Biochemical Assays: In two separate assays, 2.5 μg/μl of human TDO p... -
Tryptophan 2,3-dioxygenase IC50 = 8070.0 nM 5.09 Inhibition of N-terminal His-tagged recombinant human TDO extracted from Escheri... 39276584
Tryptophan 2,3-dioxygenase IC50 = 11580.0 nM 4.94 Inhibition of recombinant human TDO expressed in Escherichia coli BL21 using L-T... 32247733
Tryptophan 2,3-dioxygenase IC50 = 17000.0 nM 4.77 Inhibition of mouse TDO in P815 clone 12 cells by HPLC analysis 22616902
Tryptophan 2,3-dioxygenase IC50 = 18700.0 nM 4.73 Inhibition of recombinant full length C-terminal His-tagged human TDO expressed ... 30321802

Literature References

PubMed DOI Target Context # Activities
30321802 10.1016/j.ejmech.2018.10.017 Tryptophan 2,3-dioxygenase 5
22616902 10.1021/jm300260v Indoleamine 2,3-dioxygenase 1 4
21726069 10.1021/jm2006782 NON-PROTEIN TARGET 2
22616902 10.1021/jm300260v Tryptophan 2,3-dioxygenase 2
34338527 10.1021/acs.jmedchem.1c00323 Indoleamine 2,3-dioxygenase 1 2
34338527 10.1021/acs.jmedchem.1c00323 No relevant target 2
26207924 10.1021/acs.jmedchem.5b00461 Tryptophan 2,3-dioxygenase 2
- 10.6019/CHEMBL4513161 Pseudomonas aeruginosa 2
34338527 10.1021/acs.jmedchem.1c00323 Tryptophan 2,3-dioxygenase 2
31580660 10.1021/acs.jmedchem.9b01079 Tryptophan 2,3-dioxygenase 2
39276584 10.1016/j.ejmech.2024.116852 Tryptophan 2,3-dioxygenase 2
21726069 10.1021/jm2006782 Unchecked 2
21726069 10.1021/jm2006782 No relevant target 2
21726069 10.1021/jm2006782 Tryptophan 2,3-dioxygenase 2
21726069 10.1021/jm2006782 D(1A) dopamine receptor 1
21726069 10.1021/jm2006782 D(2) dopamine receptor 1
21726069 10.1021/jm2006782 Melatonin receptor type 1A 1
21726069 10.1021/jm2006782 5-hydroxytryptamine receptor 1A 1
21726069 10.1021/jm2006782 Amine oxidase [flavin-containing] B 1
21726069 10.1021/jm2006782 Amine oxidase [flavin-containing] A 1

Data from ChEMBL 36 via Core Engine