Ligand guaiacol

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Basic Ligand Information

Molecular Structure
Picture of guaiacol (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C7H8O2
guaiacol
UFPHFKCTOZIAFY-NTDVEAECSA-N
Synonyms:
2'-methylcatechol, 2-methoxybenzenol, 2-methoxyphenol, 2-methylcatechol, a guaiacol, guaiacolum, guajacol, methylcatechol, o-methoxyphenol, o-methyoxyphenol

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
guaiacol + O2 = ?
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (68 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
guaiacol + O2 = ?
show the reaction diagram
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guaiacol + H2O2 = tetraguaiacol + H2O
show the reaction diagram
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2 guaiacol + H2O2 = 3,3'-dimethoxy-4,4'-biphenylquinone + H2O
show the reaction diagram
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Br- + H2O2 + 2-methoxyphenol = 2-bromo-6-methoxyphenol + 4-bromo-6-methoxyphenol + H2O
show the reaction diagram
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o-methoxyphenol + H2O2 = ? + H2O
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2-methoxyphenol + NADH + H+ + O2 = (4S,5S)-4,5-dihydroxy-2-methoxycyclohex-2-enone + NAD+ 10
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o-methoxyphenol + NADH + H+ + O2 = 4-methoxyresorcinol + 3-methoxycatechol + NAD+ + H2O
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guaiacol + NADH + O2 = 2,3-dihydroxy-methoxybenzene + NAD+ + H2O
show the reaction diagram
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S-adenosyl-L-methionine + o-methoxyphenol = S-adenosyl-L-homocysteine + veratrole
show the reaction diagram
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S-adenosyl-L-methionine + guaiacol = ?
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S-adenosyl-L-methionine + guaiacol = S-adenosyl-L-homocysteine + ?
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guaiacol + S-adenosyl-L-methionine = 1,2-dimethoxybenzene + S-adenosyl-L-homocysteine
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UDPglucose + guaiacol = UDP + 2-methoxyphenyl beta-D-glucoside
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3'-phosphoadenylylsulfate + guaiacol = adenosine 3',5'-bisphosphate + ?
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Product in Enzyme-catalyzed Reactions (11 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
veratryl glycerol-beta-guaiacyl ether + H2O2 + H+ = veratryl aldehyde + guaiacol + H2O
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S-adenosyl-L-methionine + catechol = S-adenosyl-L-homocysteine + 2-methoxyphenol
show the reaction diagram
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glutathione + beta-(2-methoxyphenoxy)-gamma-hydroxypropiovanillone = beta-(S)-hydroxypropiovanillonyl-glutathione + guaiacol
show the reaction diagram
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guaiacol-alpha-D-glucoside + H2O = guaiacol + beta-D-glucose
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o-methoxyphenyl beta-D-xyloside = o-methoxyphenol + beta-D-xylose
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3-methoxy-4-hydroxybenzoate = 2-methoxyphenol + CO2
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2-methoxy-L-Tyr + H2O = 2-methoxyphenol + pyruvate + NH3
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Activator in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
presence of guaicol modestly increases turnover number
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about 120% activity at 1 mM
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Inhibitor in Enzyme-catalyzed Reactions (6 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
30% inhibition at 0.05 mM
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IC50: 0.175 mM, monoamine oxidase A; IC50: above 0.5 mM, monoamine oxidase B
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slight inhibition
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3D Structure of Enzyme-Ligand-Complex (PDB) (24 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (98 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.95
-
-
0.1
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pH 8.0, 35°C

KM Value (155 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.017
-
pH 8.0, 35°C

Ki Value (1 result)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.23
-
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IC50 Value (2 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE

References & Links

Links to other databases for guaiacol

ChEBI
PubChem
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PubChem