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Literature summary for 1.14.13.9 extracted from

  • Phillips, R.S.; Anderson, A.D.; Gentry, H.G.; Guener, O.F.; Bowen, J.P.
    Substrate and inhibitor specificity of kynurenine monooxygenase from Cytophaga hutchinsonii (2017), Bioorg. Med. Chem. Lett., 27, 1705-1708 .
    View publication on PubMed

Application

Application Comment Organism
medicine the enzyme is a potential drug target for treatment of neurodegenerative disorders such as Huntington's and Alzheimer's diseases Cytophaga hutchinsonii
pharmacology the enzyme is a potential drug target for treatment of neurodegenerative disorders such as Huntington's and Alzheimer's diseases Cytophaga hutchinsonii

Inhibitors

Inhibitors Comment Organism Structure
3,4-dichlorohippuric acid
-
Cytophaga hutchinsonii
3,4-dimethoxyhippuric acid
-
Cytophaga hutchinsonii
3,5-dibromo-L-kynurenine potent competitive inhibitor Cytophaga hutchinsonii
3-chloro-DL-kynurenine
-
Cytophaga hutchinsonii
3-methyl-DL-kynurenine
-
Cytophaga hutchinsonii
5-bromo-3-chloro-DL-kynurenine
-
Cytophaga hutchinsonii
5-bromo-3-methyl-DL-kynurenine
-
Cytophaga hutchinsonii
additional information kynurenines substituted with a halogen at the 5-position are excellent substrates, with values of kcat and kcat/Km comparable to or higher than kynurenine. Kynurenines substituted in the 3-position are competitive inhibitors, with KI values lower than the Km for kynurenine. Bromination also enhances inhibition. A pharmacophore model of kynurenine monooxygenase is developed, and predicted that 3,4-dichlorohippuric acid would be an inhibitor Cytophaga hutchinsonii

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.002
-
5-chloro-L-kynurenine pH and temperature not specified in the publication Cytophaga hutchinsonii
0.0045
-
5-bromo-L-kynurenine pH and temperature not specified in the publication Cytophaga hutchinsonii
0.067
-
L-kynurenine pH and temperature not specified in the publication Cytophaga hutchinsonii

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
L-kynurenine + NADPH + H+ + O2 Cytophaga hutchinsonii
-
3-hydroxy-L-kynurenine + NADP+ + H2O
-
?

Organism

Organism UniProt Comment Textmining
Cytophaga hutchinsonii Q11PP7
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
5-bromo-L-kynurenine + NADPH + H+ + O2
-
Cytophaga hutchinsonii 5-bromo-3-hydroxy-L-kynurenine + NADP+ + H2O
-
?
5-chloro-L-kynurenine + NADPH + H+ + O2
-
Cytophaga hutchinsonii 5-chloro-3-hydroxy-L-kynurenine + NADP+ + H2O
-
?
L-kynurenine + NADPH + H+ + O2
-
Cytophaga hutchinsonii 3-hydroxy-L-kynurenine + NADP+ + H2O
-
?

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.6
-
5-bromo-L-kynurenine pH and temperature not specified in the publication Cytophaga hutchinsonii
0.8
-
5-chloro-L-kynurenine pH and temperature not specified in the publication Cytophaga hutchinsonii
2
-
L-kynurenine pH and temperature not specified in the publication Cytophaga hutchinsonii

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.0015
-
3,5-dibromo-L-kynurenine pH and temperature not specified in the publication Cytophaga hutchinsonii
0.0086
-
3-methyl-DL-kynurenine pH and temperature not specified in the publication Cytophaga hutchinsonii
0.0102
-
5-bromo-3-methyl-DL-kynurenine pH and temperature not specified in the publication Cytophaga hutchinsonii
0.011
-
5-bromo-3-chloro-DL-kynurenine pH and temperature not specified in the publication Cytophaga hutchinsonii
0.0138
-
3-chloro-DL-kynurenine pH and temperature not specified in the publication Cytophaga hutchinsonii
0.034
-
3,4-dichlorohippuric acid pH and temperature not specified in the publication Cytophaga hutchinsonii
1
-
3,4-dimethoxyhippuric acid pH and temperature not specified in the publication Cytophaga hutchinsonii

General Information

General Information Comment Organism
drug target the enzyme is a potential drug target for treatment of neurodegenerative disorders such as Huntington's and Alzheimer's diseases Cytophaga hutchinsonii

kcat/KM [mM/s]

kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
29.9
-
L-kynurenine pH and temperature not specified in the publication Cytophaga hutchinsonii
133.3
-
5-bromo-L-kynurenine pH and temperature not specified in the publication Cytophaga hutchinsonii
400
-
5-chloro-L-kynurenine pH and temperature not specified in the publication Cytophaga hutchinsonii