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Literature summary for 1.13.11.11 extracted from

  • Kozlova, A.; Thabault, L.; Liberelle, M.; Klaessens, S.; Prevost, J.R.C.; Mathieu, C.; Pilotte, L.; Stroobant, V.; Van den Eynde, B.; Frederick, R.
    Rational design of original fused-cycle selective inhibitors of tryptophan 2,3-dioxygenase (2021), J. Med. Chem., 64, 10967-10980 .
    View publication on PubMed

Inhibitors

Inhibitors Comment Organism Structure
1-(cyclopropylmethyl)-5-(1H-indol-3-yl)-1H-benzotriazole
-
Homo sapiens
1-(cyclopropylmethyl)-6-(1H-indol-3-yl)-1H-benzotriazole
-
Homo sapiens
2-[5-(1H-indol-3-yl)-1H-benzotriazol-1-yl]-N,N-dimethylethan-1-amine
-
Homo sapiens
2-[5-(1H-indol-3-yl)-1H-benzotriazol-1-yl]acetamide
-
Homo sapiens
2-[6-(1H-indol-3-yl)-1H-benzotriazol-1-yl]-N,N-dimethylethan-1-amine
-
Homo sapiens
2-[6-(1H-indol-3-yl)-1H-benzotriazol-1-yl]acetamide
-
Homo sapiens
3-[5-(1H-indol-3-yl)-1H-benzotriazol-1-yl]propane-1,2-diol
-
Homo sapiens
3-[6-(1H-indol-3-yl)-1H-benzotriazol-1-yl]propane-1,2-diol
-
Homo sapiens
5-(1H-indol-3-yl)-1-(2,2,2-trifluoroethyl)-1H-benzotriazole
-
Homo sapiens
5-(1H-indol-3-yl)-1-methyl-1H-benzotriazol-4-amine
-
Homo sapiens
5-(1H-indol-3-yl)-1-methyl-1H-benzotriazole
-
Homo sapiens
5-(1H-indol-3-yl)-1-[(oxolan-2-yl)methyl]-1H-benzotriazole
-
Homo sapiens
5-(1H-indol-3-yl)-1-[(oxolan-3-yl)methyl]-1H-benzotriazole
-
Homo sapiens
5-(1H-indol-3-yl)-1-[(piperidin-4-yl)methyl]-1H-benzotriazole
-
Homo sapiens
5-(1H-indol-3-yl)-1-[2-(morpholin-4-yl)ethyl]-1H-benzotriazole
-
Homo sapiens
5-(1H-indol-3-yl)-1-[2-(piperazin-1-yl)ethyl]-1H-benzotriazole
-
Homo sapiens
5-(1H-indol-3-yl)-1-[2-(pyrrolidin-3-yl)ethyl]-1H-benzotriazole
-
Homo sapiens
5-(1H-indol-3-yl)-2-methyl-2H-benzotriazol-4-amine
-
Homo sapiens
5-(1H-indol-3-yl)-2-methyl-2H-benzotriazole
-
Homo sapiens
5-(6-fluoro-1H-indol-3-yl)-1-methyl-1H-benzotriazole
-
Homo sapiens
5-(6-fluoro-1H-indol-3-yl)-1-[2-(piperazin-1-yl)ethyl]-1H-benzotriazole
-
Homo sapiens
6-(1H-indol-3-yl)-1-(2,2,2-trifluoroethyl)-1H-benzotriazole
-
Homo sapiens
6-(1H-indol-3-yl)-1-methyl-1H-benzotriazol-7-amine
-
Homo sapiens
6-(1H-indol-3-yl)-1-methyl-1H-[1,2,3]triazolo[4,5-b]pyridine
-
Homo sapiens
6-(1H-indol-3-yl)-1-methyl-7-nitro-1H-benzotriazole
-
Homo sapiens
6-(1H-indol-3-yl)-1-[(oxolan-2-yl)methyl]-1H-benzotriazole
-
Homo sapiens
6-(1H-indol-3-yl)-1-[(oxolan-3-yl)methyl]-1H-benzotriazole
-
Homo sapiens
6-(1H-indol-3-yl)-1-[(piperidin-4-yl)methyl]-1H-benzotriazole
-
Homo sapiens
6-(1H-indol-3-yl)-1-[(pyrrolidin-3-yl)methyl]-1H-benzotriazole
-
Homo sapiens
6-(1H-indol-3-yl)-1-[2-(morpholin-4-yl)ethyl]-1H-benzotriazole
-
Homo sapiens
6-(1H-indol-3-yl)-1-[2-(piperazin-1-yl)ethyl]-1H-benzotriazole
-
Homo sapiens
6-(1H-indol-3-yl)-1H-benzotriazole
-
Homo sapiens
6-(1H-indol-3-yl)-2-methyl-2H-[1,2,3]triazolo[4,5-b]pyridine
-
Homo sapiens
6-(1H-indol-3-yl)-3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridine
-
Homo sapiens
6-(1H-indol-3-yl)isoquinoline
-
Homo sapiens
6-(1H-indol-3-yl)quinazoline
-
Homo sapiens
6-fluoro-3-[(E)-2-(1H-tetrazol-5-yl)ethenyl]-1H-indole
-
Homo sapiens
6-fluoro-3-[(E)-2-(pyridin-3-yl)ethenyl]-1H-indole
-
Homo sapiens
7-(1H-indol-3-yl)-3,4-dihydroquinazolin-2(1H)-one
-
Homo sapiens
7-(1H-indol-3-yl)isoquinoline
-
Homo sapiens
7-(1H-indol-3-yl)quinazoline
-
Homo sapiens
[5-(1H-indol-3-yl)-1H-benzotriazol-1-yl]acetic acid
-
Homo sapiens
[6-(1H-indol-3-yl)-1H-benzotriazol-1-yl]acetic acid
-
Homo sapiens

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
L-tryptophan + O2 Homo sapiens
-
N-formyl-L-kynurenine
-
?

Organism

Organism UniProt Comment Textmining
Homo sapiens P48775
-
-

Source Tissue

Source Tissue Comment Organism Textmining
liver
-
Homo sapiens
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
L-tryptophan + O2
-
Homo sapiens N-formyl-L-kynurenine
-
?

Synonyms

Synonyms Comment Organism
TDO2
-
Homo sapiens

Cofactor

Cofactor Comment Organism Structure
heme heme-containing enzyme Homo sapiens

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.00068
-
37°C, pH 6.28 Homo sapiens 2-[6-(1H-indol-3-yl)-1H-benzotriazol-1-yl]acetamide
0.0011
-
37°C, pH 6.14 Homo sapiens 5-(6-fluoro-1H-indol-3-yl)-1-methyl-1H-benzotriazole
0.00132
-
37°C, pH 6.22 Homo sapiens 6-(1H-indol-3-yl)-1-methyl-7-nitro-1H-benzotriazole
0.00162
-
37°C, pH 6.27 Homo sapiens 2-[5-(1H-indol-3-yl)-1H-benzotriazol-1-yl]acetamide
0.0019
-
37°C, pH 6.24 Homo sapiens 6-(1H-indol-3-yl)-1-(2,2,2-trifluoroethyl)-1H-benzotriazole
0.002 0.0034 37°C, pH 6.11 Homo sapiens 6-(1H-indol-3-yl)-1H-benzotriazole
0.00385
-
37°C, pH 6.16 Homo sapiens 5-(1H-indol-3-yl)-2-methyl-2H-benzotriazol-4-amine
0.00387
-
37°C, pH 6.13 Homo sapiens 5-(1H-indol-3-yl)-1-methyl-1H-benzotriazole
0.0039
-
37°C, pH 6.26 Homo sapiens 1-(cyclopropylmethyl)-6-(1H-indol-3-yl)-1H-benzotriazole
0.00393
-
37°C, pH 6.18 Homo sapiens 6-(1H-indol-3-yl)-1-methyl-1H-benzotriazol-7-amine
0.004
-
37°C, pH 6.12 Homo sapiens 5-(1H-indol-3-yl)-2-methyl-2H-benzotriazole
0.0049 0.0066 37°C, pH 6.7 Homo sapiens 6-(1H-indol-3-yl)isoquinoline
0.00501
-
37°C, pH 6.17 Homo sapiens 5-(1H-indol-3-yl)-1-methyl-1H-benzotriazol-4-amine
0.0052
-
37°C, pH 6.45 Homo sapiens 6-(1H-indol-3-yl)-1-[2-(piperazin-1-yl)ethyl]-1H-benzotriazole
0.0056 0.0071 37°C, pH 6.6 Homo sapiens 7-(1H-indol-3-yl)isoquinoline
0.00602
-
37°C, pH 6.15 Homo sapiens 6-(1H-indol-3-yl)-1H-benzotriazole
0.0061 0.0087 37°C, pH 6.5 Homo sapiens 6-fluoro-3-[(E)-2-(1H-tetrazol-5-yl)ethenyl]-1H-indole
0.00783
-
37°C, pH 6.20 Homo sapiens 6-(1H-indol-3-yl)-3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridine
0.00908
-
37°C, pH 6.21 Homo sapiens 6-(1H-indol-3-yl)-1-methyl-1H-[1,2,3]triazolo[4,5-b]pyridine
0.0127 0.0229 37°C, pH 6.10 Homo sapiens 7-(1H-indol-3-yl)-3,4-dihydroquinazolin-2(1H)-one
0.0128 0.0169 37°C, pH 6.8 Homo sapiens 6-(1H-indol-3-yl)quinazoline
0.01306
-
37°C, pH 6.19 Homo sapiens 6-(1H-indol-3-yl)-2-methyl-2H-[1,2,3]triazolo[4,5-b]pyridine
0.0135
-
37°C, pH 6.25 Homo sapiens 1-(cyclopropylmethyl)-5-(1H-indol-3-yl)-1H-benzotriazole
0.015
-
37°C, pH 6.23 Homo sapiens 5-(1H-indol-3-yl)-1-(2,2,2-trifluoroethyl)-1H-benzotriazole
0.017
-
37°C, pH 6.46 Homo sapiens 3-[5-(1H-indol-3-yl)-1H-benzotriazol-1-yl]propane-1,2-diol
0.01773
-
37°C, pH 6.39 Homo sapiens 5-(1H-indol-3-yl)-1-[(piperidin-4-yl)methyl]-1H-benzotriazole
0.0211
-
37°C, pH 6.36 Homo sapiens 6-(1H-indol-3-yl)-1-[(oxolan-2-yl)methyl]-1H-benzotriazole
0.0212 0.0326 37°C, pH 6.9 Homo sapiens 7-(1H-indol-3-yl)quinazoline
0.0219
-
37°C, pH 6.34 Homo sapiens 6-(1H-indol-3-yl)-1-[(oxolan-3-yl)methyl]-1H-benzotriazole
0.0246
-
37°C, pH 6.32 Homo sapiens 2-[6-(1H-indol-3-yl)-1H-benzotriazol-1-yl]-N,N-dimethylethan-1-amine
0.0249
-
37°C, pH 6.43 Homo sapiens 5-(1H-indol-3-yl)-1-[2-(piperazin-1-yl)ethyl]-1H-benzotriazole
0.0252
-
37°C, pH 6.47 Homo sapiens 3-[6-(1H-indol-3-yl)-1H-benzotriazol-1-yl]propane-1,2-diol
0.02551
-
37°C, pH 6.40 Homo sapiens 6-(1H-indol-3-yl)-1-[(piperidin-4-yl)methyl]-1H-benzotriazole
0.0261
-
37°C, pH 6.41 Homo sapiens 5-(1H-indol-3-yl)-1-[2-(pyrrolidin-3-yl)ethyl]-1H-benzotriazole
0.0369
-
37°C, pH 6.31 Homo sapiens 2-[5-(1H-indol-3-yl)-1H-benzotriazol-1-yl]-N,N-dimethylethan-1-amine
0.0369
-
37°C, pH 6.35 Homo sapiens 5-(1H-indol-3-yl)-1-[(oxolan-2-yl)methyl]-1H-benzotriazole
0.0441
-
37°C, pH 6.33 Homo sapiens 5-(1H-indol-3-yl)-1-[(oxolan-3-yl)methyl]-1H-benzotriazole
0.045
-
37°C, pH 6.44 Homo sapiens 5-(6-fluoro-1H-indol-3-yl)-1-[2-(piperazin-1-yl)ethyl]-1H-benzotriazole
0.04565
-
37°C, pH 6.42 Homo sapiens 6-(1H-indol-3-yl)-1-[(pyrrolidin-3-yl)methyl]-1H-benzotriazole
0.0526
-
37°C, pH 6.38 Homo sapiens 6-(1H-indol-3-yl)-1-[2-(morpholin-4-yl)ethyl]-1H-benzotriazole
0.1045
-
37°C, pH 6.30 Homo sapiens [6-(1H-indol-3-yl)-1H-benzotriazol-1-yl]acetic acid
0.1186
-
37°C, pH 6.37 Homo sapiens 5-(1H-indol-3-yl)-1-[2-(morpholin-4-yl)ethyl]-1H-benzotriazole
0.1738
-
37°C, pH 6.29 Homo sapiens [5-(1H-indol-3-yl)-1H-benzotriazol-1-yl]acetic acid

General Information

General Information Comment Organism
physiological function the enzyme is responsible for L-tryptophan (L-Trp) homeostasis. Expression of TDO2 in cancer cells results in the inhibition of immune-mediated tumor rejection due to an enhancement of L-Trp catabolism via the kynurenine pathway Homo sapiens