Ligand catechol

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Basic Ligand Information

Molecular Structure
Picture of catechol (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C6H6O2
catechol
HOVAGTYPODGVJG-ZFYZTMLRSA-N
Synonyms:
1,2-dihydroxybenzene, 2,3-catechol, 2-hydroxyphenol, a catechol, benzene-1,2-diol, brenzcatechin, Dihydroxybenzene, o-benzenediol, o-dihydroxybenzene, pyrocatechol
Pathway Source
Pathways
BRENDA
phenol degradation
KEGG
Aminobenzoate degradation, Benzoate degradation, Chlorocyclohexane and chlorobenzene degradation, Degradation of aromatic compounds, Dioxin degradation more
MetaCyc
1,3-dichlorobenzene degradation, 1,4-dichlorobenzene degradation, 2,4-dichlorophenoxyacetate degradation, 2-chlorobenzoate degradation, 2-isopropylphenol degradation more


Show all pahtways known for Show all BRENDA pathways known for catechol

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (13 results)

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EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
4 catechol + O2 = 4 1,2-benzoquinone + 2 H2O
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catechol + O2 = ?
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S-adenosyl-L-methionine + a catechol = ?
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catechol + CO2 = 2,3-dihydroxybenzoate
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (20 results)

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EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
2-chlorobenzoate + NADH + O2 = catechol + chloride + NAD+ + CO2
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phenol + NADH + H+ + O2 = catechol + NAD+ + H2O
show the reaction diagram
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2-nitrophenol + NADPH + H+ + O2 = catechol + NADP+ + H2O + nitrite
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phenol + FADH2 + O2 = catechol + FAD + H2O
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trans-1,2-dihydrobenzene-1,2-diol + NAD(P)+ = catechol + NAD(P)H
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(-)-3,5-cyclohexadiene-1,2-diol-1-carboxylic acid + NAD+ = catechol + CO2 + NADH
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carboxylic acid diol + NAD+ = catechol + NADH
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2,3-Dihydroxybenzoate = Catechol + CO2
show the reaction diagram
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L-3-4 dihydroxyphenylalanine + H2O = catechol + pyruvate + NH3
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (123 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
catechol + O2 = dibenzo[1,4]dioxin-2,3-dione + H2O
show the reaction diagram
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catechol + O2 = o-benzoquinone + H2O2
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catechol + O2 = ?
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catechol + O2 = ?
show the reaction diagram
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pyrocatechol + H2O2 = 1,2-benzoquinone + H2O
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catechol + H2O2 = ?
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catechol + H2O2 = ?
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catechol + H2O2 = 2-benzoquinone + H2O
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catechol + H2O2 + H+ = ?
show the reaction diagram
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catechol + H2O2 = ? + H2O
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catechol + H2O2 = ? + H2O
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catechol + O2 = 2-hydroxy-6-oxohexa-2,4-dienoate
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catechol + O2 = 2-hydroxymuconic acid semialdehyde
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catechol + O2 = ?
show the reaction diagram
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catechol + O2 = ?
show the reaction diagram
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catechol + O2 = ?
show the reaction diagram
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catechol + O2 + NAD(P)H + H2O = ?
show the reaction diagram
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catechol + ? = ?
show the reaction diagram
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catechol + O2 = ?
show the reaction diagram
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catechol + O2 = ?
show the reaction diagram
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NADPH + H+ + catechol = NADP+ + ?
show the reaction diagram
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S-adenosyl-L-methionine + catechol = S-adenosyl-L-homocysteine + 2-methoxyphenol
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UDP-glucose + catechol = ?
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UDPglucose + catechol = UDP + 2-(beta-D-glucopyranosyloxy)phenol
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sucrose + catechol = D-fructose + catechol glucoside
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catechol + hesperidin = 2-hydroxyphenyl beta-D-rutinoside + hesperetin
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catechol + H2O = ?
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catechol + H2O = ?
show the reaction diagram
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catechol + CO2 = 2,3-dihydroxybenzoate
show the reaction diagram
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Catechol + CO2 = 3,4-Dihydroxybenzoate
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (78 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
benzene dihydrodiol + NADP+ = catechol + NADPH
show the reaction diagram
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phenol + H2O2 = hydroquinone + catechol + H2O
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phenol + NADH + O2 = catechol + hydroquinone + NAD+
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nitrobenzene + NADH + O2 = catechol + nitrite + NAD+
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phenol + NADH + H+ + O2 = catechol + NAD+ + H2O
show the reaction diagram
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phenol + NADH + H+ + O2 = catechol + NAD+ + H2O
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phenol + ? = catechol + ?
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monophenol + O2 = catechol + H2O
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benzene cis-dihydrodiol + NAD+ = catechol + NADH + H+
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2-hydroxyphenyl sulfate + H2O = 2-hydroxyphenol + sulfate
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2,3-Dihydroxybenzoate = Catechol + CO2
show the reaction diagram
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protocatechuic acid = catechol + CO2
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3,4-Dihydroxybenzoate = Catechol + CO2
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2,3-dihydroxybenzoate = 1,2-dihydroxybenzene + CO2
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (4 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
5 mM catechol results in a 5-8fold acceleration of the rate of oxidation of 2.5 mM L-Dopa
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6 mM, increase in expression of azoR mRNA relative to the expression at zero time before stress is applied, at 10 min 15.6, at 20 min 31.9
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Inhibitor in Enzyme-catalyzed Reactions (62 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
i.e. 1,2-butanediol, inactivation, enzyme regains activity after removal of alcohol
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75% inhibition at 1 mM
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45% inhibition at 1 mM
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0.019 mM, 50% inhibition, uncompetitive
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IC50: 0.062 mM
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0.2 mM, 93% inhibition; 0.2 mM, 93% inhibition
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competitive with respect to 2-oxoglutarate and ascorbate, noncompetitive with respect to Fe2+
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substrate inhibition
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0.1 mM and 1 mM, 64% and 98% inhibition of benzaldehyde oxidation, respectively
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tested at 1.0 mM, 14% inhibition
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50% inhibition of overall enzyme reaction at 7.4 mM, 50% inhibition of ketoacyl reduction reaction at 21 mM
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weak
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89% inhibition
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competitive
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irreversibly inactivates the enzyme with a complex radical-based autocatalytic multistep mechanism
competitive
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24% inhibition at 0.01 mM, 52% inhibition at 0.05 mM
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3D Structure of Enzyme-Ligand-Complex (PDB) (76 results)

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EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (112 results)

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EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
12
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at pH 7.0 and 55°C
12
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in 50 mM sodium phosphate, pH 7.0, 30°C
24
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wild type enzyme, at pH 3.0 and 22°C
13.3
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9.67
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pH 7.5, 25°C
0.141
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30°C, pH not specified in the publication
0.78
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pH 6.0, 40°C
2.68
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recombinant enzyme, L-DOPA formation is measured from dicatechol, pyruvate, and ammonium, pH 8.5, 20°C

KM Value (248 results)

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EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
19
-
at pH 7.0 and 55°C
19
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in 50 mM sodium phosphate, pH 7.0, 30°C
19
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wild type enzyme, at pH 3.0 and 22°C
0.72
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0.66
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0.012
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0.282
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40
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2
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isozyme I
19.4
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30°C, pH not specified in the publication
24.9
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pH 6.0, 40°C

Ki Value (16 results)

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EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
3.8
-
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0.0104
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pH and temperature not specified in the publication
0.025
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0.015
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12.5
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0.01
-
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IC50 Value (7 results)

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EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
1.2
-
-
0.056
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pH 7.0, 23°C
0.062
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IC50: 0.062 mM

References & Links

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Links to other databases for catechol

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ChEBI
PubChem
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PubChem