Ligand hydroquinone

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Basic Ligand Information

Molecular Structure
Picture of hydroquinone (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C6H6O2
hydroquinone
QIGBRXMKCJKVMJ-UHFFFAOYSA-N
Synonyms:
1,4-benzenediol, 1,4-benzohydroquinol, 1,4-benzohydroquinone, 1,4-benzoquinol, 1,4-dihydroxybenzene, 1,4-hydroquinone, 1,4-hydroxyquinone, 4-hydroxyphenol, benzene-1,4-diol, benzenediol, benzohydroquinone, benzoquinol, ELDOQUIN (TN), hydroquinol, p-benzenediol, p-benzohydroquinone, p-benzoquinol, p-hydroquinone, quinol, quinone (reduced), reduced 1,4-benzoquinone


Show all pahtways known for Show all BRENDA pathways known for hydroquinone

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (6 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
benzene-1,4-diol + O2 = (2Z,4E)-4-hydroxy-6-oxohexa-2,4-dienoate
show the reaction diagram
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methane + quinol + O2 = methanol + quinone + H2O
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nitrate + quinol = nitrite + quinone + H2O
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UDP-glucose + hydroquinone = UDP + hydroquinone-O-beta-D-glucopyranoside
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (16 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
(S)-malate + quinone = oxaloacetate + quinol
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cellobiose + 1,4-benzoquinone = cellobiono-1,5-lactone + reduced 1,4-benzoquinone
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4-hydroxybenzoate + NAD(P)H + H+ + O2 = hydroquinone + NAD(P)+ + H2O + CO2
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pyruvate + quinone + H2O = acetate + CO2 + quinol
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quinone + NAD(P)H = hydroquinone + NAD(P)+
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glutathione + 2-(glutathione-S-yl)-hydroquinone = glutathione disulfide + hydroquinone
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arbutin + H2O = 4-hydroxyphenol + beta-D-glucose
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Substrate in Enzyme-catalyzed Reactions (68 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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p-hydroquinone + O2 = ?
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1,4-benzohydroquinone + H2O2 = ? + H2O
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hydroquinone + H2O2 + H+ = ?
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hydroquinone + H2O2 = benzoquinone + H2O
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hydroquinone + H2O2 = ? + H2O
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hydroquinone + O2 = ?
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hydroquinone + NADP+ + O2 = ? + NADP+ + H2O
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quinol + O2 + NADPH = 1,2,4-trihydroxybenzene + NADP+ + H2O
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methane + quinol + O2 = methanol + quinone + H2O
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1,4-hydroxyquinone + acceptor + H2O = ?
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hydroquinone + O2 = ?
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hydroquinone + O2 = ?
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hydroquinone + O2 = ?
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fumarate + quinol = succinate + ubiquinone
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sucrose + hydroquinone = D-glucose + 4-hydroxyphenyl-beta-D-fructofuranoside
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UDP-glucose + hydroquinone = UDP + hydroquinone O-beta-D-glucoside
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UDPglucose + hydroquinone = UDP + 4-beta-D-glucopyranosyloxyphenol
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sucrose + hydroquinone = D-fructose + hydroquinone-O-alpha-D-glucopyranoside
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sucrose + hydroquinone = D-fructose + 4-hydroxyphenyl-alpha-D-glucopyranoside
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sucrose + hydroquinone = D-fructose + ?
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UDPglucose + hydroquinone = UDP + hydroquinone glucoside
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sucrose + hydroquinone = ?
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3'-phosphoadenylylsulfate + hydroquinone = adenosine 3',5'-bisphosphate + ?
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3'-phosphoadenylylsulfate + hydroquinone = adenosine 3',5'-bisphosphate + hydroquinone sulfate
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lactose + hydroquinone = hydroquinone galactoside + D-glucose
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hydroquinone + H2O = ?
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Product in Enzyme-catalyzed Reactions (139 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
1,4-benzoquinone + NADPH + H+ = 1,4-benzoquinol + NADP+
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formaldehyde + p-benzoquinone = formic acid + p-benzoquinol
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sn-glycerol 3-phosphate + quinone = glycerone phosphate + quinol
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(S)-malate + quinone = oxaloacetate + quinol
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D-glucose + 1,4-benzoquinone = D-glucono-1,5-lactone + 1,4-benzoquinol
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H2O + 1,4-benzoquinone + hv = O2 + 1,4-benzoquinol
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phenol + H2O2 = hydroquinone + catechol + H2O
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phenol + NADH + O2 = catechol + hydroquinone + NAD+
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4-hydroxybenzoate + NADH + H+ + O2 = hydroquinone + NAD+ + H2O + CO2
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phenol + NADH + H+ + O2 = hydroquinone + ? + NAD+ + H2O
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4-hydroxyphenoxyacetate + ? = hydroquinone + glycolate + ?
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benzene + NAD(P)H + O2 = cyclohexanol + phenol + hydroquinone + NAD(P)+ + H2O
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4-hydroxybenzoate + NAD(P)H + O2 = quinol + NAD(P)+ + H2O2 + CO2
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4-chlorphenol + O2 = hydroquinone + H2O + Cl-
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xanthine + p-benzoquinone + H2O = hypoxanthine + hydroquinone
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phenylacetyl-CoA + H2O + quinone = phenylglyoxylyl-CoA + quinol
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NADH + p-benzoquinone = NAD+ + p-benzoquinol
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pyruvate + quinone + H2O = acetate + CO2 + quinol
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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
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1,4-benzoquinone + NADH + H+ = 1,4-benzoquinol + NAD+
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benzoquinone + NADH = benzoquinol + NAD+
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NADPH + H+ + 1,4-benzoquinone = NADP+ + 1,4-benzoquinol
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nitrite + reduced hydroquinone = nitric oxide + H2O + hydroquinone
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1,4-benzoquinone + NADH = 1,4-benzoquinol + NAD+
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glutathione + 2-(glutathione-S-yl)-hydroquinone = glutathione disulfide + hydroquinone
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4-hydroxyphenyl acetate + H2O = 4-hydroxyphenol + acetate
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hydroquinone sulfate + H2O = hydroquinone + sulfate
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arbutin + H2O = D-glucose + benzene-1,4-diol
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arbutin = benzene-1,4-diol + beta-D-glucose
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esculin + H2O = D-glucose + 4-hydroxyphenol
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hydroquinone-beta-D-glucopyranoside + H2O = hydroquinone + D-glucose
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arbutin 6-phosphate + H2O = hydroquinone + D-glucose 6-phosphate
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Nalpha-(4-hydroxybenzoyl)-L-Asp + H2O = 1,4-dihydroxybenzene + CO2 + L-Asp
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2,5-dihydroxybenzoate = 4-hydroxyphenol + CO2
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2,5-Dihydroxybenzoate = Hydroquinone + CO2
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Enzyme Cofactor/Cosubstrate (3 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE

Activator in Enzyme-catalyzed Reactions (6 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
0.1 mM concentration 123% activation
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2 mM, slight activation, cellulase I
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physiological precursor of 1,4-benzoquinone, a topoisomerase II poison, enhances cleavage activity, inhibits ligation activity, at 0.25 mM, alters the enzyme's cleavage site specificity, 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
lower inhibitry potency, about 25% inhibition at 0.0025 mM
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98% inhibition at 1 mM
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4.7 mM, 50% inhibition
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tested at 1.0 mM and under N2, 31% inhibition
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shows noncompetitive inhibition in all conditions, it can bind to multiple enzyme forms or sites, even when either of the substrates (NADH or benzoquinone) is present at high concentrations
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5 mM, complete inhibition
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Glu274 is acting as an acidic backbone acceptor residue. Lys262, a basic amino acid from the active site of wheat Hydroquinone glucosyltransferase interacts with the hydroxyl group of hydroquinone and behaves as a side chain donor molecule. Asp264 is also observed as an interacting residue from the active site of hydroquinone glucosyltransferase. It binds to the hydroxyl group of hydroquinone inhibitor and donates hydrogen ion from its side chain group
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strongly inhibits in absence of 2-mercaptoethanol
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98% inhibition
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competitive
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irreversible inhibition
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11% residual activity at 1 mM
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noncompetitive inhibition, has minimal cytotoxicity against mammalian cells. Hydroquinone binds near the active center of alanine racemase
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3D Structure of Enzyme-Ligand-Complex (PDB) (3 results)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (22 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
31
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wild type enzyme, at pH 3.0 and 22°C
101.5
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pH 7.0, 25°C
1600
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25°C, pH 6.5

KM Value (43 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
6.3
-
wild type enzyme, at pH 3.0 and 22°C
60
-
-
53
-
-
647.5
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25°C, pH 6.5

Ki Value (7 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
14
-
-
0.0106
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at pH 7.5 and 20°C
0.212
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pH 11.0, 35°C, recombinant His-tagged enzyme

IC50 Value (10 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.0026
-
pH 7.4, 37°C
0.0026
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at pH 7.8 and 37°C
0.0185
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pH 11.0, 35°C, recombinant His-tagged enzyme

References & Links

Links to other databases for hydroquinone

ChEBI
PubChem
ChEBI
PubChem