Ligand o-Cresol

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Basic Ligand Information

Molecular Structure
Picture of o-Cresol (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C7H8O
o-Cresol
QWVGKYWNOKOFNN-UHFFFAOYSA-N
Synonyms:
2-Cresol, 2-methyl-phenol, 2-methylphenol, hydroxytoluene, o-methylphenol
Pathway Source
Pathways
KEGG
Degradation of aromatic compounds, Microbial metabolism in diverse environments, Toluene degradation
MetaCyc
toluene degradation to 2-hydroxypentadienoate I (via o-cresol)

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (3 results)

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EC NUMBER
LITERATURE
REACTION DIAGRAM
PROVEN IN VIVO REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
2-methylphenol + O2 = ?
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show the reaction diagram
2-cresol + NADH + H+ + O2 = ?
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show the reaction diagram
2-methylphenol + NADH + H+ + O2 = 3-methylcatechol + NAD+ + H2O
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In Vivo Product in Enzyme-catalyzed Reactions (2 results)

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EC NUMBER
LITERATURE
REACTION DIAGRAM
PROVEN IN VIVO REACTION
ENZYME 3D STRUCTURE
-
show the reaction diagram
toluene + NADH + H+ + O2 = 2-methylphenol + NAD+ + H2O
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show the reaction diagram
3 toluene + 3 NADPH + 3 H+ + 3 O2 = 2-cresol + 3-cresol + 4-cresol + 3 NADP+ + 3 H2O
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Substrate in Enzyme-catalyzed Reactions (26 results)

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EC NUMBER
LITERATURE
REACTION DIAGRAM
REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
Br- + H2O2 + 2-methylphenol = 2-bromo-6-methylphenol + 4-bromo-6-methylphenol + H2O
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show the reaction diagram
o-cresol + H2O2 = ?
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show the reaction diagram
2-methylphenol + O2 = ?
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show the reaction diagram
o-cresol + NADH + O2 = methylhydroquinone + 3-methylcatechol + NAD+
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show the reaction diagram
o-cresol + NADH + H+ + O2 = methylhydroquinone + 2-hydroxybenzyl alcohol + nitrite + NAD+
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show the reaction diagram
o-cresol + NADH + H+ + O2 = 3-methylcatechol + NAD+ + H2O
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show the reaction diagram
2-methylphenol + NADH + H+ + O2 = 3-methylcatechol + NAD+ + H2O
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show the reaction diagram
2-methylphenol + NADH + O2 = 1,2-dihydroxy-3-methylbenzene + NAD+ + H2O
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show the reaction diagram
2-cresol + NADH + H+ + O2 = ?
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show the reaction diagram
2-methyl-phenol + O2 + NADPH = ?
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show the reaction diagram
S-adenosyl-L-methionine + o-methylphenol = S-adenosyl-L-homocysteine + o-methylanisole
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show the reaction diagram
3'-phosphoadenylylsulfate + 2-methylphenol = adenosine 3',5'-bisphosphate + 2-methylphenyl sulfate
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show the reaction diagram
3'-phosphoadenylylsulfate + o-cresol = adenosine 3',5'-bisphosphate + o-cresol sulfate
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show the reaction diagram
o-cresol + fumarate = (2-hydroxybenzyl)succinic acid
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Product in Enzyme-catalyzed Reactions (11 results)

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EC NUMBER
LITERATURE
REACTION DIAGRAM
REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
2-methylbenzoate + NADH + O2 = o-cresol + ? + NAD+ + CO2
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-
show the reaction diagram
toluene + NADH + H+ + O2 = 2-methylphenol + NAD+ + H2O
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show the reaction diagram
o-cresyl alpha-D-galactoside + H2O = o-cresol + D-galactose
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show the reaction diagram
o-methylphenyl beta-D-xyloside + H2O = o-methylphenol + beta-D-xylose
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show the reaction diagram
2-methyl-L-Tyr + H2O = 2-methylphenol + pyruvate + NH3
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Inhibitor in Enzyme-catalyzed Reactions (6 results)

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COMMENTARY
EC NUMBER
LITERATURE
ENZYME 3D STRUCTURE
24.7% inhibition at 0.1 mM
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butylated, 50% inhibition at 1 mM
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5 mM, 67% inhibition
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cleavage of Tyr
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2.93 mM, 50% inhibition
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3D Structure of Enzyme-Ligand-Complex (PDB) (1 result)

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EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (2 results)

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COMMENTARY
EC NUMBER
LITERATURE
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
25°C, recombinant enzyme
0.95
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at pH 7.5 and 30°C
0.000035
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KM Value (5 results)

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COMMENTARY
EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
LITERATURE
native enzyme, in 0.01 M phosphate buffer at pH 7.5 and 25°C
16.7
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pyromellitic dianhydride-modified enzyme, in 0.01 M phosphate buffer at pH 7.5 and 25°C
9.1
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pH 7.5, 23°C
0.0008
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25°C, recombinant enzyme
0.0031
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at pH 7.5 and 30°C
0.035
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Ki Value (1 result)

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COMMENTARY
EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
LITERATURE
25°C, pH 8.8
0.8
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IC50 Value (1 result)

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COMMENTARY
EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
LITERATURE
pH and temperature not specified in the publication
0.0231
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References & Links

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Links to other databases for o-Cresol

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ChEBI
PubChem
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PubChem