Ligand 2,3-dimethoxy-5-methyl-1,4-benzoquinone

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Basic Ligand Information

Molecular Structure
Picture of 2,3-dimethoxy-5-methyl-1,4-benzoquinone (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C9H10O4
2,3-dimethoxy-5-methyl-1,4-benzoquinone
YNDYKPRNFWPPFU-GOSISDBHSA-N
Synonyms:
2,3-dimethoxy-5-methyl-2,5-cyclohexadiene-1,4-dione, 2,3-dimethoxy-5-methyl-p-benzoquinone, 2,3-dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione, 2,3-dimetoxy-5-methyl-1,4-benzoquinone, 5-methyl-2,3-dimethoxybenzene-1,4-diol, coenzyme Q0, conenzyme Q0, CoQ0, ubiquinone-0, ubiquinone 0, ubiquinone0

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
sn-glycerol 3-phosphate + coenzyme Q0 = dihydroxyacetone phosphate + reduced coenzyme Q0
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (58 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
D-glucose + 2,3-dimethoxy-5-methyl-1,4-benzoquinone = D-glucono-1,5-lactone + ?
show the reaction diagram
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(S)-malate + ubiquinone-0 = oxaloacetate + ubiquinol-0
show the reaction diagram
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2,3-dimethoxy-5-methyl-1,4-benzoquinone + reduced coenzyme F420 = 2,3-dimethoxy-5-methyl-1,4-benzoquinol + oxidized coenzyme F420
show the reaction diagram
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D-fructose + 2,3-dimethoxy-5-methyl-1,4-benzoquinone = 5-dehydro-D-fructose + 2,3-dimethoxy-5-methyl-1,4-benzoquinol
show the reaction diagram
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propylene + coenzyme Q0 + O2 = propylene oxide + reduced coenzyme Q0 + H2O
show the reaction diagram
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succinate + 2,3-dimethoxy-5-methyl-1,4-benzoquinone = fumarate + 2,3-dimethoxy-5-methyl-1,4-benzohydroquinone
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
nicotinamide riboside + reduced coenzyme Q0 = dihydronicotinamide riboside + coenzyme Q0
show the reaction diagram
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2 2,3-dimethoxy-5-methyl-1,4-benzoquinol + O2 + 4 H+[side 1] = 2 2,3-dimethoxy-5-methyl-1,4-benzoquinone + 2 H2O + 4 H+[side 2]
show the reaction diagram
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Enzyme Cofactor/Cosubstrate (5 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
triple cofactor requirement for FAD, quinone and phospholipid. Maximum activation rate when phosphatidylethanolamine is added to the enzyme before the quinone
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preferred electron acceptor
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little catalytic efficiency, N-terminally truncated protein
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0.2 mM quinone stimulates reaction with D-alanine and oxidized 2,6-dichloroindophenol 16fold
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Activator in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
reduction of 2,6-dichlorophenol indophenol by solubilized enzyme is activated significantly by addition of the quinones decylubiquinone, duroquinone, 2-methyl-1,4-naphthoquinone (vitamin K3), ubiquinone-0 and ubiquinone-1. Optimal activation is observed with ubiquinone-1
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Inhibitor in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
above 0.03 mM
-
formation of coenzyme Q0-dihydrolipoamide adducts in the E2 components of the alpha-ketoglutarate complex (i.e. dihydrolipoamide succinyltransferase) partially explains the cellular toxicity of coenzyme Q0
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Enzyme Kinetic Parameters

kcat Value (Turnover Number) (8 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
32
-
pH 8.0, 30C
143.6
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pH 6.5, recombinant enzyme
0.068
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pH 7.4, 25C

KM Value (12 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.125
-
-
0.0137
-
using N-benzyl dihydronicotinamide as cosubstrate, at 25C, in 50 mM Tris-HCl, pH 8.5
0.003
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value below
0.0044
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pH 7.4, 25C
0.0065
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in 10 mM bis-Tris-propane buffer (pH 7.2), at 25C

References & Links

Links to other databases for 2,3-dimethoxy-5-methyl-1,4-benzoquinone

ChEBI
PubChem
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PubChem