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Literature summary extracted from

  • John, S.E.St.; Jensen, K.C.; Kang, S.; Chen, Y.; Calamini, B.; Mesecar, A.D.; Lipton, M.A.
    Design, synthesis, biological and structural evaluation of functionalized resveratrol analogues as inhibitors of quinone reductase 2 (2013), Bioorg. Med. Chem., 21, 6022-6037.
    View publication on PubMedView publication on EuropePMC

Cloned(Commentary)

EC Number Cloned (Comment) Organism
1.10.5.1 expression in Escherichia coli strain BL21(DE3) Homo sapiens

Crystallization (Commentary)

EC Number Crystallization (Comment) Organism
1.10.5.1 purified recombinant enzyme, hanging-drop, vapor-diffusion method, mixing of 0.001 ml of 4 mg/ml protein solution with 0.001 ml of reservoir solution containing 1.3-1.7 M ammonium sulfate, 0.1 M Bis-Tris buffer, pH 6.0-7.0, 0.1 M NaCl, 5 mM DTT, 0.012 mM FAD, and resveratrol, complexed with different inhibitors, X-ray diffraction structure determination and analysis at resolutions of 1.40-1.63 A Homo sapiens

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.10.5.1 (E)-3-(3,5-dihydroxyphenyl)-2-(4-hydroxyphenyl)acrylaldehyde
-
 Homo sapiens
1.10.5.1 (E)-3-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)prop-2-en-1-ol
-
 Homo sapiens
1.10.5.1 (Z)-3-(3,5-dihydroxyphenyl)-2-(4-hydroxyphenyl)-acrylamide
-
 Homo sapiens
1.10.5.1 (Z)-3-(3,5-dihydroxyphenyl)-2-(4-hydroxyphenyl)acrylonitrile
-
 Homo sapiens
1.10.5.1 (Z)-3-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)acrylaldehyde
-
 Homo sapiens
1.10.5.1 (Z)-3-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)acrylonitrile
-
 Homo sapiens
1.10.5.1 (Z)-5-(3-hydroxy-2-(4-hydroxyphenyl)prop-1-en-1-yl)benzene-1,3-diol
-
 Homo sapiens
1.10.5.1 1,1'-(1E)-but-1-ene-1,2-diylbis(3,5-dimethoxybenzene)
-
 Homo sapiens
1.10.5.1 1,2-dimethoxy-4-[(1E)-2-(4-methoxyphenyl)prop-1-en-1-yl]benzene
-
 Homo sapiens
1.10.5.1 1,2-dimethoxy-4-[(E)-2-(3-methoxyphenyl)ethenyl]benzene
-
 Homo sapiens
1.10.5.1 1,2-dimethoxy-4-{(1Z)-3,3,3-trifluoro-2-[3-(trifluoromethyl)phenyl]prop-1-en-1-yl}benzene
-
 Homo sapiens
1.10.5.1 1,3-dimethoxy-5-[(1E)-2-(4-methoxyphenyl)prop-1-en-1-yl]benzene
-
 Homo sapiens
1.10.5.1 1,3-dimethoxy-5-[(1Z)-3,3,3-trifluoro-1-(4-methoxyphenyl)prop-1-en-2-yl]benzene
-
 Homo sapiens
1.10.5.1 1,3-dimethoxy-5-[(E)-2-(4-methoxyphenyl)ethenyl]benzene
-
 Homo sapiens
1.10.5.1 1-[(E)-2-(4-fluorophenyl)ethenyl]-3,5-dimethoxybenzene
-
 Homo sapiens
1.10.5.1 2-[(E)-2-(3,4-dimethoxyphenyl)ethenyl]naphthalene
-
 Homo sapiens
1.10.5.1 2-[(E)-2-(3,5-dimethoxyphenyl)ethenyl]naphthalene
-
 Homo sapiens
1.10.5.1 4-[(1E)-1-(3,5-dimethoxyphenyl)prop-1-en-2-yl]-1,2-dimethoxybenzene
-
 Homo sapiens
1.10.5.1 4-[(E)-2-(3,4-dimethoxyphenyl)ethenyl]-N,N-dimethylaniline
-
 Homo sapiens
1.10.5.1 4-[(E)-2-(3,5-dimethoxyphenyl)ethenyl]-1,2-dimethoxybenzene
-
 Homo sapiens
1.10.5.1 4-[(E)-2-(3,5-dimethoxyphenyl)ethenyl]phenol
-
 Homo sapiens
1.10.5.1 4-[(E)-2-(3-fluorophenyl)ethenyl]benzene-1,2-diol
-
 Homo sapiens
1.10.5.1 4-[(E)-2-(4-hydroxyphenyl)ethenyl]benzene-1,2-diol
-
 Homo sapiens
1.10.5.1 4-[(E)-2-(4-methoxyphenyl)ethenyl]benzene-1,2-diol
-
 Homo sapiens
1.10.5.1 4-{(1E)-1-[4-(trifluoromethyl)phenyl]prop-1-en-2-yl}phenol
-
 Homo sapiens
1.10.5.1 4-{(E)-2-[3-(trifluoromethyl)phenyl]ethenyl}benzene-1,2-diol
-
 Homo sapiens
1.10.5.1 5-[(1E)-1-(4-hydroxyphenyl)prop-1-en-2-yl]benzene-1,3-diol
-
 Homo sapiens
1.10.5.1 5-[(1E)-2-(3,4-dimethoxyphenyl)prop-1-en-1-yl]benzene-1,3-diol
-
 Homo sapiens
1.10.5.1 5-[(1E)-2-(4-hydroxyphenyl)prop-1-en-1-yl]benzene-1,3-diol
-
 Homo sapiens
1.10.5.1 5-[(1E)-2-(4-methoxyphenyl)prop-1-en-1-yl]benzene-1,3-diol
-
 Homo sapiens
1.10.5.1 5-{(1E)-1-[4-(dimethylamino)phenyl]but-1-en-2-yl}benzene-1,3-diol
-
 Homo sapiens
1.10.5.1 additional information enzyme inhibitor design, synthesiis, and evaluation, inhibitory potencies of resveratrol analogues, overview. Inhibitor binding structure, modelling, overview Homo sapiens
1.10.5.1 N-(3,5-dihydroxyphenyl)-4-hydroxybenzamide
-
 Homo sapiens
1.10.5.1 resveratrol i.e. 3,5,4'-trihydroxylstilbene, resveratrol binds tightly to the oxidized, FAD-form of the enzyme, and it acts as a competitive inhibitor against N-methyldihydronicotinamide. The amount of resveratrol consumed from dietary sources may be sufficient for effective inhibition of QR2 Homo sapiens

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
1.10.5.1 additional information
-
 additional information steady-state kinetic, overview Homo sapiens

Organism

EC Number Organism UniProt Comment Textmining
1.10.5.1 Homo sapiens
-
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
1.10.5.1 recombinant enzyme from Escherichia coli strain BL21(DE3) Homo sapiens

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.10.5.1 N-methyldihydronicotinamide + 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide
-
 Homo sapiens N-methylnicotinamide + ?
-
 ?
1.10.5.1 N-methyldihydronicotinamide + menadione
-
 Homo sapiens N-methylnicotinamide + menadiol
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.10.5.1 QR2
-
 Homo sapiens
1.10.5.1 quinone reductase 2
-
 Homo sapiens

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
1.10.5.1 25
-
 assay at Homo sapiens

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
1.10.5.1 7.5
-
 assay at Homo sapiens

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
1.10.5.1 0.000088
-
 resveratrol versus N-methyldihydronicotinamide, pH and temperature not specified in the publication Homo sapiens

General Information

EC Number General Information Comment Organism
1.10.5.1 physiological function the enzyme functions in metabolic reduction and detoxification processes. Evidence exists linking QR2 to the metabolic activation of quinones, which can lead to cell toxicity. Inhibition of the enzymme by resveratrol may protect cells against reactive intermediates and eventually cancer Homo sapiens