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Literature summary for 1.1.1.184 extracted from

  • Hartmanova, T.; Tambor, V.; Len?o, J.; Staab-Weijnitz, C.A.; Maser, E.; Wsol, V.
    S-nitrosoglutathione covalently modifies cysteine residues of human carbonyl reductase 1 and affects its activity (2013), Chem. Biol. Interact., 202, 136-145.
    View publication on PubMed

Inhibitors

Inhibitors Comment Organism Structure
S-nitrosoglutathione treatment leads concentration-dependent S-glutathionylation of cysteines at positions 122, 150, 226, 227. Residues C226/C227 form a disulfide bond. Treatment results in a 2–5fold decrease in kcat with menadione, 4-benzoylpyridine, 2,3-hexanedione, daunorubicinand 1,4-naphthoquinone, with concomitant increase in kcat for substrates containing a 1,2-diketo group in a ring structure. Except for 9,10-phenanthrenequinone, all changes in kcat are at least in part compensated for by a similar change in Km, overall yielding no drastic changes in catalytic efficiency Homo sapiens

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.0008
-
isatin wild-type, pH 7.4, 37°C Homo sapiens
0.0073
-
1,4-Naphthoquinone wild-type, pH 7.4, 25°C Homo sapiens
0.0073
-
1,4-Naphthoquinone wild-type, pH 7.4, 37°C Homo sapiens
0.008
-
isatin wild-type, pH 7.4, 25°C Homo sapiens
0.014
-
menadione after treatment with S-nitrosoglutathione, pH 7.4, 25°C Homo sapiens
0.014
-
menadione enzyme modified by S-nitrosoglutathione, pH 7.4, 37°C Homo sapiens
0.016
-
4-benzoylpyridine after treatment with S-nitrosoglutathione, pH 7.4, 25°C Homo sapiens
0.016
-
4-benzoylpyridine enzyme modified by S-nitrosoglutathione, pH 7.4, 37°C Homo sapiens
0.017
-
isatin after treatment with S-nitrosoglutathione, pH 7.4, 25°C Homo sapiens
0.017
-
isatin enzyme modified by S-nitrosoglutathione, pH 7.4, 37°C Homo sapiens
0.018
-
menadione wild-type, pH 7.4, 25°C Homo sapiens
0.018
-
menadione wild-type, pH 7.4, 37°C Homo sapiens
0.018
-
9,10-phenanthrenequinone after treatment with S-nitrosoglutathione, pH 7.4, 25°C Homo sapiens
0.018
-
9,10-phenanthrenequinone enzyme modified by S-nitrosoglutathione, pH 7.4, 37°C Homo sapiens
0.032
-
9,10-phenanthrenequinone wild-type, pH 7.4, 25°C Homo sapiens
0.032
-
9,10-phenanthrenequinone wild-type, pH 7.4, 37°C Homo sapiens
0.032
-
1,4-Naphthoquinone after treatment with S-nitrosoglutathione, pH 7.4, 25°C Homo sapiens
0.032
-
1,4-Naphthoquinone enzyme modified by S-nitrosoglutathione, pH 7.4, 37°C Homo sapiens
0.034
-
oracin enzyme modified by S-nitrosoglutathione, pH 7.4, 37°C Homo sapiens
0.043
-
daunorubicin enzyme modified by S-nitrosoglutathione, pH 7.4, 37°C Homo sapiens
0.06
-
2,3-Hexanedione after treatment with S-nitrosoglutathione, pH 7.4, 25°C Homo sapiens
0.06
-
2,3-Hexanedione enzyme modified by S-nitrosoglutathione, pH 7.4, 37°C Homo sapiens
0.067
-
daunorubicin wild-type, pH 7.4, 37°C Homo sapiens
0.07
-
1,2-naphthoquinone wild-type, pH 7.4, 25°C Homo sapiens
0.07
-
1,2-naphthoquinone wild-type, pH 7.4, 37°C Homo sapiens
0.096
-
oracin wild-type, pH 7.4, 37°C Homo sapiens
0.117
-
1,2-naphthoquinone after treatment with S-nitrosoglutathione, pH 7.4, 25°C Homo sapiens
0.117
-
1,2-naphthoquinone enzyme modified by S-nitrosoglutathione, pH 7.4, 37°C Homo sapiens
0.159
-
2,3-Hexanedione wild-type, pH 7.4, 25°C Homo sapiens
0.159
-
2,3-Hexanedione wild-type, pH 7.4, 37°C Homo sapiens
0.25
-
4-benzoylpyridine wild-type, pH 7.4, 25°C Homo sapiens
0.25
-
4-benzoylpyridine wild-type, pH 7.4, 37°C Homo sapiens
5.85
-
4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone enzyme modified by S-nitrosoglutathione, pH 7.4, 37°C Homo sapiens
7.84
-
4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone wild-type, pH 7.4, 37°C Homo sapiens

Organism

Organism UniProt Comment Textmining
Homo sapiens P16152
-
-

Posttranslational Modification

Posttranslational Modification Comment Organism
additional information in presence of S-nitrosoglutathione, S-glutathionylation of cysteines at positions 122, 150, 226, 227 occurs. GSNO treatment of CBR1 results in a 2–5-fold decrease in kcat with menadione, 4-benzoylpyridine, 2,3-hexanedione, daunorubicin and 1,4-naphthoquinone and an increased kcat for substrates containing a 1,2-diketo group in a ring structure such as 1,2-naphthoquinone, 9,10-phenanthrenequinone, isatin Homo sapiens
additional information presence of a disulfide bond between neighboring residues Cys226 and Cys227 Homo sapiens

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1,2-naphthoquinone + NADPH + H+
-
Homo sapiens ? + NADP+
-
?
1,4-naphthoquinone + NADPH + H+
-
Homo sapiens ? + NADP+
-
?
2,3-hexanedione + NADPH + H+
-
Homo sapiens ? + NADP+
-
?
4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone + NADPH + H+
-
Homo sapiens 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol + NADP+
-
?
4-benzoylpyridine + NADPH + H+
-
Homo sapiens (S)-phenyl(pyridin-4-yl)methanol + NADP+
-
?
4-benzoylpyridine + NADPH + H+
-
Homo sapiens ? + NADP+
-
?
9,10-phenanthrenequinone + NADPH + H+
-
Homo sapiens ? + NADP+
-
?
daunorubicin + NADPH + H+
-
Homo sapiens daunorubicinol + NADP+
-
?
isatin + NADPH + H+
-
Homo sapiens 3-hydroxy-2-oxoindole + NADP+
-
?
isatin + NADPH + H+
-
Homo sapiens ? + NADP+
-
?
menadione + NADPH + H+
-
Homo sapiens ? + NADP+
-
?
oracin + NADPH + H+
-
Homo sapiens 11-dihydrooracin + NADP+
-
?

Synonyms

Synonyms Comment Organism
CBR1
-
Homo sapiens
SDR21C1
-
Homo sapiens

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.17
-
isatin wild-type, pH 7.4, 25°C Homo sapiens
0.17
-
isatin wild-type, pH 7.4, 37°C Homo sapiens
0.25
-
1,4-Naphthoquinone after treatment with S-nitrosoglutathione, pH 7.4, 25°C Homo sapiens
0.25
-
4-benzoylpyridine enzyme modified by S-nitrosoglutathione, pH 7.4, 37°C Homo sapiens
0.28
-
menadione after treatment with S-nitrosoglutathione, pH 7.4, 25°C Homo sapiens
0.28
-
1,4-Naphthoquinone enzyme modified by S-nitrosoglutathione, pH 7.4, 37°C Homo sapiens
0.3
-
4-benzoylpyridine after treatment with S-nitrosoglutathione, pH 7.4, 25°C Homo sapiens
0.3
-
isatin enzyme modified by S-nitrosoglutathione, pH 7.4, 37°C Homo sapiens
0.32
-
2,3-Hexanedione after treatment with S-nitrosoglutathione, pH 7.4, 25°C Homo sapiens
0.32
-
menadione enzyme modified by S-nitrosoglutathione, pH 7.4, 37°C Homo sapiens
0.38
-
oracin enzyme modified by S-nitrosoglutathione, pH 7.4, 37°C Homo sapiens
0.48
-
daunorubicin enzyme modified by S-nitrosoglutathione, pH 7.4, 37°C Homo sapiens
0.55
-
1,4-Naphthoquinone wild-type, pH 7.4, 25°C Homo sapiens
0.55
-
1,4-Naphthoquinone wild-type, pH 7.4, 37°C Homo sapiens
0.68
-
menadione wild-type, pH 7.4, 25°C Homo sapiens
0.68
-
menadione wild-type, pH 7.4, 37°C Homo sapiens
1
-
4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone enzyme modified by S-nitrosoglutathione, pH 7.4, 37°C Homo sapiens
1.2
-
4-benzoylpyridine wild-type, pH 7.4, 25°C Homo sapiens
1.2
-
4-benzoylpyridine wild-type, pH 7.4, 37°C Homo sapiens
1.27
-
daunorubicin wild-type, pH 7.4, 37°C Homo sapiens
1.52
-
2,3-Hexanedione enzyme modified by S-nitrosoglutathione, pH 7.4, 37°C Homo sapiens
1.67
-
oracin wild-type, pH 7.4, 37°C Homo sapiens
2.02
-
4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone wild-type, pH 7.4, 37°C Homo sapiens
3.47
-
1,2-naphthoquinone wild-type, pH 7.4, 25°C Homo sapiens
3.47
-
1,2-naphthoquinone wild-type, pH 7.4, 37°C Homo sapiens
3.57
-
9,10-phenanthrenequinone wild-type, pH 7.4, 25°C Homo sapiens
3.57
-
9,10-phenanthrenequinone wild-type, pH 7.4, 37°C Homo sapiens
5.13
-
2,3-Hexanedione wild-type, pH 7.4, 25°C Homo sapiens
5.13
-
2,3-Hexanedione wild-type, pH 7.4, 37°C Homo sapiens
6.7
-
9,10-phenanthrenequinone after treatment with S-nitrosoglutathione, pH 7.4, 25°C Homo sapiens
6.7
-
1,2-naphthoquinone after treatment with S-nitrosoglutathione, pH 7.4, 25°C Homo sapiens
6.7
-
1,2-naphthoquinone enzyme modified by S-nitrosoglutathione, pH 7.4, 37°C Homo sapiens
9.77
-
isatin after treatment with S-nitrosoglutathione, pH 7.4, 25°C Homo sapiens
9.77
-
9,10-phenanthrenequinone enzyme modified by S-nitrosoglutathione, pH 7.4, 37°C Homo sapiens

kcat/KM [mM/s]

kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
0.17
-
4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone enzyme modified by S-nitrosoglutathione, pH 7.4, 37°C Homo sapiens
0.25
-
4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone wild-type, pH 7.4, 37°C Homo sapiens
4.8
-
4-benzoylpyridine wild-type, pH 7.4, 25°C Homo sapiens
4.8
-
4-benzoylpyridine wild-type, pH 7.4, 37°C Homo sapiens
8.7
-
1,4-Naphthoquinone after treatment with S-nitrosoglutathione, pH 7.4, 25°C Homo sapiens
8.7
-
1,4-Naphthoquinone enzyme modified by S-nitrosoglutathione, pH 7.4, 37°C Homo sapiens
11.2
-
daunorubicin enzyme modified by S-nitrosoglutathione, pH 7.4, 37°C Homo sapiens
11.3
-
oracin enzyme modified by S-nitrosoglutathione, pH 7.4, 37°C Homo sapiens
12.2
-
oracin wild-type, pH 7.4, 37°C Homo sapiens
15.7
-
4-benzoylpyridine after treatment with S-nitrosoglutathione, pH 7.4, 25°C Homo sapiens
15.7
-
4-benzoylpyridine enzyme modified by S-nitrosoglutathione, pH 7.4, 37°C Homo sapiens
18.3
-
daunorubicin wild-type, pH 7.4, 37°C Homo sapiens
18.3
-
isatin after treatment with S-nitrosoglutathione, pH 7.4, 25°C Homo sapiens
18.3
-
isatin enzyme modified by S-nitrosoglutathione, pH 7.4, 37°C Homo sapiens
21.7
-
isatin wild-type, pH 7.4, 25°C Homo sapiens
21.7
-
isatin wild-type, pH 7.4, 37°C Homo sapiens
21.7
-
menadione after treatment with S-nitrosoglutathione, pH 7.4, 25°C Homo sapiens
21.7
-
menadione enzyme modified by S-nitrosoglutathione, pH 7.4, 37°C Homo sapiens
25
-
2,3-Hexanedione after treatment with S-nitrosoglutathione, pH 7.4, 25°C Homo sapiens
25
-
2,3-Hexanedione enzyme modified by S-nitrosoglutathione, pH 7.4, 37°C Homo sapiens
31.6
-
2,3-Hexanedione wild-type, pH 7.4, 25°C Homo sapiens
31.7
-
2,3-Hexanedione wild-type, pH 7.4, 37°C Homo sapiens
38.3
-
menadione wild-type, pH 7.4, 25°C Homo sapiens
38.3
-
menadione wild-type, pH 7.4, 37°C Homo sapiens
50
-
1,2-naphthoquinone wild-type, pH 7.4, 25°C Homo sapiens
50
-
1,2-naphthoquinone wild-type, pH 7.4, 37°C Homo sapiens
56.7
-
1,2-naphthoquinone after treatment with S-nitrosoglutathione, pH 7.4, 25°C Homo sapiens
56.7
-
1,2-naphthoquinone enzyme modified by S-nitrosoglutathione, pH 7.4, 37°C Homo sapiens
73.3
-
1,4-Naphthoquinone wild-type, pH 7.4, 25°C Homo sapiens
73.3
-
1,4-Naphthoquinone wild-type, pH 7.4, 37°C Homo sapiens
113
-
9,10-phenanthrenequinone wild-type, pH 7.4, 25°C Homo sapiens
113
-
9,10-phenanthrenequinone wild-type, pH 7.4, 37°C Homo sapiens
533
-
9,10-phenanthrenequinone after treatment with S-nitrosoglutathione, pH 7.4, 25°C Homo sapiens
533
-
9,10-phenanthrenequinone enzyme modified by S-nitrosoglutathione, pH 7.4, 37°C Homo sapiens