Ligand 1,4-benzoquinone

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Basic Ligand Information

Molecular Structure
Picture of 1,4-benzoquinone (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C6H4O2
1,4-benzoquinone
AZQWKYJCGOJGHM-UHFFFAOYSA-N
Synonyms:
4-benzoquinone, benzoquinone, cyclohexa-2,5-diene-1,4-dione, p-benzoquinone, p-quinone, quinone, semiquinone anion


Show all pahtways known for Show all BRENDA pathways known for 1,4-benzoquinone

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (16 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
(S)-malate + quinone = oxaloacetate + quinol
show the reaction diagram
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cellobiose + 1,4-benzoquinone = cellobiono-1,5-lactone + reduced 1,4-benzoquinone
show the reaction diagram
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pyruvate + quinone + H2O = acetate + CO2 + quinol
show the reaction diagram
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NADPH + H+ + 2 quinone = NADP+ + 2 semiquinone
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (5 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
4-nitrophenol + NADPH + H+ + O2 = 1,4-benzoquinone + nitrite + NADP+ + H2O
show the reaction diagram
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methane + quinol + O2 = methanol + quinone + H2O
show the reaction diagram
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nitrate + quinol = nitrite + quinone + H2O
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (158 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
p-quinone + NADPH = ?
show the reaction diagram
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1,4-benzoquinone + NADPH + H+ = 1,4-benzoquinol + NADP+
show the reaction diagram
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formaldehyde + p-benzoquinone = formic acid + p-benzoquinol
show the reaction diagram
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sn-glycerol 3-phosphate + quinone = glycerone phosphate + quinol
show the reaction diagram
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(S)-malate + quinone = oxaloacetate + quinol
show the reaction diagram
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D-glucose + 1,4-benzoquinone = D-glucono-1,5-lactone + 1,4-benzoquinol
show the reaction diagram
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H2O + 1,4-benzoquinone + hv = O2 + 1,4-benzoquinol
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quinone + Fe2+ + O2 = ?
show the reaction diagram
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phenylacetyl-CoA + H2O + quinone = phenylglyoxylyl-CoA + quinol
show the reaction diagram
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NADH + p-benzoquinone = NAD+ + p-benzoquinol
show the reaction diagram
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1,4-benzoquinone + NADP+ = ? + NADPH + H+
show the reaction diagram
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pyruvate + quinone + H2O = acetate + CO2 + quinol
show the reaction diagram
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CO + benzoquinone + H2O = CO2 + benzoquinol
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L-galactono-1,4-lactone + 1,4-benzoquinone = L-ascorbate + reduced 1,4-benzoquinone
show the reaction diagram
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1,4-benzoquinone + NADH + H+ = 1,4-benzoquinol + NAD+
show the reaction diagram
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benzoquinone + NADH = benzoquinol + NAD+
show the reaction diagram
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NADPH + H+ + 1,4-benzoquinone = NADP+ + 1,4-benzoquinol
show the reaction diagram
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1,4-benzoquinone + NADH = 1,4-benzoquinol + NAD+
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (24 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
hydroquinone + inosine + O2 = p-quinone + 9-riburonosylhypoxanthine + H2O
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2 hydroquinone + O2 = 2 quinone + 2 H2O
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4-fluorophenol + H2O2 = 1,4-benzoquinone + ?
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4-phenoxyphenol + H2O2 = phenol + 1,4-benzoquinone
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isoniazid + phenol + H2O2 = benzoquinone + ?
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hydroquinone + H2O2 = benzoquinone + H2O
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phenol + bromide = 4-benzoquinone + 2-chlorophenol
show the reaction diagram
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4-nitrophenol + O2 + NADPH + H+ = 4-benzoquinone + nitrite + H2O + NADP+
show the reaction diagram
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methane + quinol + O2 = methanol + quinone + H2O
show the reaction diagram
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glutathione + 2-(glutathione-S-yl)-1,4-benzoquinone = glutathione disulfide + 1,4-benzoquinone
show the reaction diagram
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Enzyme Cofactor/Cosubstrate (13 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
dependent on
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with a periplasmically oriented quinone binding site of the enzyme
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since phytoene desaturation responds to the redox state of quinones, which is adjusted by the respiratory redox pathway, the two reactions must be regarded as being mechanistically linked. Using redox titrations, it is shown that the optimal activity lies in the range of the midpoint potential of the plastoquinone/plastohydroquinone redox couple
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lysyl oxidase and 4 LOX-like proteins LOXL, LOXL2, LOXL3, and LOXL4 all contain conserved lysyl and tyrosyl residues that may contribute to quinone cofactor formation
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contains a quinone similar to but not identical with the prosthetic group of EC 1.1.99.8
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heme bD is distal to NarGH and constitutes part of the quinone binding and oxidation site (Q-site) through the axially coordinating His66 residue and one of the heme bD propionate groups. Bound quinone participates in hydrogen bonds with both the imidazole of His66 and the heme propionate; heme bD is distal to NarGH and constitutes part of the quinone binding and oxidation site (Q-site) through the axially coordinating His66 residue and one of the heme bD propionate groups. Bound quinone participates in hydrogen bonds with both the imidazole of His66 and the heme propionate; heme bD is distal to NarGH and constitutes part of the quinone binding and oxidation site (Q-site) through the axially coordinating His66 residue and one of the heme bD propionate groups. Bound quinone participates in hydrogen bonds with both the imidazole of His66 and the heme propionate
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Activator in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
stimulates conversion of prostaglandin G1 to H1
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a topoisomerase II poison in vivo and in vitro, enhances cleavage activity, inhibits ligation activity, at 0.025 mM, 1,4-hydroquinone has a higher inhibitory effect on ligation activity but a lower effect on cleavage activity compared to 1,4-benzoquinone
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Inhibitor in Enzyme-catalyzed Reactions (33 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
1.7 mM, complete inhibition
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competitive inhibition of the activity with 2,6-dichlorophenolindophenol or coenzyme Q1, non-competitive inhibition of reaction with phenazine methosulfate
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0.25 mM, 50% inhibition, competitive
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strong inhibitor
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0.01 mM concentration 100% inhibition
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inhibition of succinate dehydrogenase activity using phenazone methosulfate or 2,6-dichlorophenolindophenol as electron acceptor; inhibitory to the succinate dehydrogenase activity assay using phenazine methosulfate and 2,6-dichloroindophenol
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strong
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IC50: 0.4 mM
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1 mM, 84% inhibition
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irreversible inhibition
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3D Structure of Enzyme-Ligand-Complex (PDB) (2 results)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (76 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
15.5
-
-
108
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in the presence of L-galactono-1,4-lactone, in 50 mM sodium phosphate (pH 8.8), at 25°C
108
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KM Value (97 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.75
-
-
0.0088
-
pH 7.1, temperature not specified in the publication
0.05
-
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3.33
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pH 5.5, 35°C
0.83
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at 10 mM choline
0.0657
-
-
0.28
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wild type enzyme, in the presence of L-galactono-1,4-lactone, in 50 mM sodium phosphate (pH 8.8), at 25°C

Ki Value (3 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0009
-
wild-type, pH 6.7, 37°C
0.18
-
-
0.25
-
-

IC50 Value (5 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.0028
-
wild-type, pH 6.7, 37°C
0.4
-
IC50: 0.4 mM
0.0051
-
-
0.00017
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pH 7.4, 37°C
0.00017
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at pH 7.8 and 37°C

References & Links

Links to other databases for 1,4-benzoquinone

ChEBI
PubChem
ChEBI
PubChem