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BRENDA support

Ligand phenol

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Basic Ligand Information

Molecular Structure
Picture of phenol (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
Molfile
C6H6O
phenol
ISWSIDIOOBJBQZ-UHFFFAOYSA-N
 Download
Synonyms:
4-hydroxybenzol, benzenol, hydroxybenzene, monophenol, phenols, phenoxy radical

Related pathways

Pathway Source
Pathways
BRENDA
phenol degradation, tyrosine metabolism
KEGG
Aminobenzoate degradation, Benzoate degradation, Chemical carcinogenesis - reactive oxygen species, Chlorocyclohexane and chlorobenzene degradation, Degradation of aromatic compounds more
MetaCyc
benzene degradation II (aerobic), benzene degradation IV (anaerobic), diphenyl ethers degradation, methanogenesis from methoxylated aromatic compounds, methoxylated aromatic compound degradation I more


Show all pahtways known for Show all BRENDA pathways known for phenol

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (19 results)

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EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
phenol + O2 = ?
show the reaction diagram
-
phenol + NADH + H+ + O2 = catechol + NAD+ + H2O
show the reaction diagram
-
monophenol + O2 = o-diphenol + H2O
show the reaction diagram
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beta-nicotinate D-ribonucleotide + phenol = nicotinate + phenyl 5-phospho-alpha-D-ribofuranoside
show the reaction diagram
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ATP + phenol + H2O = AMP + phenyl phosphate + phosphate
show the reaction diagram
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3'-phosphoadenylyl sulfate + phenol = adenosine 3',5'-bisphosphate + phenyl sulfate
show the reaction diagram
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4-nitrophenyl sulfate + phenol = 4-nitrophenol + phenyl sulfate
show the reaction diagram
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Phenol + CO2 = ?
show the reaction diagram
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phenol + pyruvate + NH3 = L-tyrosine + H2O
show the reaction diagram
-

In Vivo Product in Enzyme-catalyzed Reactions (8 results)

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EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
delphinidin 3-rutinoside-7-(6-(p-hydroxybenzoyl)-glucoside) + p-hydroxybenzoyl-glucose = delphinidin 3-rutinoside-7-(6-(4-(glucosyl)-oxybenzoyl)-glucoside) + 4-hydroxybenzol
show the reaction diagram
-
-
cadusafos + H2O = O,O-diethylphosphorodithioate + phenol
show the reaction diagram
-
-
salicylate = phenol + CO2
show the reaction diagram
-
-
L-tyrosine + H2O = phenol + pyruvate + NH3
show the reaction diagram
-
-

Substrate in Enzyme-catalyzed Reactions (97 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
phenol + ferricytochrome c = ?
show the reaction diagram
-
phenol + O2 = ?
show the reaction diagram
-
phenol + H2O2 + H+ = ?
show the reaction diagram
-
H2O2 + phenol = ?
show the reaction diagram
-
phenol + O2 = ?
show the reaction diagram
-
phenol + NADH + H+ + O2 = (1S,2R)-cyclohexa-3,5-diene-1,2,4-triol + (2S)-cyclohexa-3,5-diene-1,1,2-triol + NAD+
show the reaction diagram
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phenol + NADH + O2 = catechol + hydroquinone + NAD+
show the reaction diagram
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phenol + NADH + H+ + O2 = hydroquinone + ? + NAD+ + H2O
show the reaction diagram
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phenol + NADH + H+ + O2 = catechol + NAD+ + H2O
show the reaction diagram
-
phenol + NADH + H+ + O2 = catechol + NAD+ + H2O
show the reaction diagram
-
monophenol + O2 = catechol + H2O
show the reaction diagram
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S-adenosyl-L-methionine + phenol = S-adenosyl-L-homocysteine + anisole
show the reaction diagram
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phenol + S-adenosyl-L-methionine = methoxybenzene + S-adenosyl-L-homocysteine
show the reaction diagram
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acyl-CoA + phenol = ? + CoA
show the reaction diagram
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phenol + palmitoyl-CoA = phenyl palmitate + CoA
show the reaction diagram
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UDP-glucose + phenol = UDP + phenyl-beta-D-glucopyranoside
show the reaction diagram
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UDPglucose + phenol = UDP + phenyl beta-D-glucoside
show the reaction diagram
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UDP-alpha-D-glucose + phenol = UDP + phenyl beta-D-glucopyranoside
show the reaction diagram
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UDP-glucose + phenol = UDP + phenyglucoside
show the reaction diagram
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beta-nicotinate D-ribonucleotide + phenol = nicotinate + phenyl 5-phospho-alpha-D-ribofuranoside
show the reaction diagram
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O3-acetyl-L-serine + phenol = O-phenyl-L-serine + acetate
show the reaction diagram
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ATP + phenol + H2O = AMP + phenyl phosphate + phosphate
show the reaction diagram
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3'-phosphoadenylyl-sulfate + phenol = adenosine 3',5'-bisphosphate + phenyl sulfate
show the reaction diagram
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3'-phosphoadenylyl 5'-phosphosulfate + phenol = adenosine 3',5'-bisphosphate + phenyl sulfate
show the reaction diagram
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3'-phosphoadenylylsulfate + phenol = adenosine 3',5'-bisphosphate + phenyl sulfate
show the reaction diagram
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phenol + D-glucose + H2O = phenyl D-glucoside
show the reaction diagram
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Phenol + CO2 = 4-Hydroxybenzoate
show the reaction diagram
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phenol + CO2 = salicylate
show the reaction diagram
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O-acetyl-L-serine + phenol = S-phenyl-L-serine + acetate
show the reaction diagram
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phenol/in + ATP + H2O = phenol/out + ADP + phosphate
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (135 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
4-phenoxyphenol + H2O2 = phenol + 1,4-benzoquinone
show the reaction diagram
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benzene + H2O2 = phenol + H2O
show the reaction diagram
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phenetole + NADH + H+ + O2 = phenol + vinyloxybenzene + (S)-ethylphenyl sulfoxide + NAD+
show the reaction diagram
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phenetole + NADH + H+ + O2 = phenol + NAD+ + ?
show the reaction diagram
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phenylboronic acid + NADPH + O2 = phenol + BO3- + NADP+ + H2O
show the reaction diagram
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benzene + NADH + H+ + O2 = phenol + NAD+ + H2O
show the reaction diagram
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benzene + NADH + H+ + O2 = phenol + NAD+ + H2O
show the reaction diagram
-
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cyclohex-2-enone + 2,6-dichlorophenol indophenol = phenol + reduced 2,6-dichlorophenol indophenol
show the reaction diagram
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delphinidin 3-rutinoside-7-(6-(p-hydroxybenzoyl)-glucoside) + p-hydroxybenzoyl-glucose = delphinidin 3-rutinoside-7-(6-(4-(glucosyl)-oxybenzoyl)-glucoside) + 4-hydroxybenzol
show the reaction diagram
-
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O-phenyl-L-homoserine + L-cysteine = L-cystathionine + phenol
show the reaction diagram
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phenyl sulfate + an aryl alcohol = phenol + an aryl sulfate
show the reaction diagram
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phenyl acetate + H2O = phenol + acetate
show the reaction diagram
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phenyl acetate + H2O = phenol + acetate
show the reaction diagram
652394, -
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phenyl acetate + H2O = phenol + acetate
show the reaction diagram
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phenyl phosphate + H2O = phenol + phosphate
show the reaction diagram
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phenylphosphate + H2O = phenol + phosphate
show the reaction diagram
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phenyl methylphosphonate + H2O = phenol + methylphosphonate
show the reaction diagram
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diphenyl phosphate + H2O = phenyl phosphate + phenol
show the reaction diagram
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phenyl sulfate + H2O = phenol + sulfate
show the reaction diagram
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phenyl sulfate + H2O = phenol + sulfate
show the reaction diagram
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phenyl-alpha-D-glucopyranoside + H2O = D-glucose + phenol
show the reaction diagram
326246, -
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phenyl-beta-galactoside + H2O = phenol + beta-D-galactose
show the reaction diagram
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phenyl 6-phospho-alpha-D-glucoside + H2O = phenol + alpha-D-glucose 6-phosphate
show the reaction diagram
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phenyl-beta-D-glucoside = phenol + beta-D-glucose
show the reaction diagram
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phenyl-beta-D-glucoside + H2O = phenol + D-glucose
show the reaction diagram
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phenyl-alpha-D-mannopyranoside + H2O = alpha-D-mannopyranose + phenol
show the reaction diagram
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phenyl-alpha-N-acetylglucosaminide + H2O = N-acetylgalactosamine + phenol
show the reaction diagram
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phenyl-N-acetyl-alpha-D-glucosaminide + H2O = phenol + N-acetyl-alpha-D-glucosamine
show the reaction diagram
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phenyl alpha-L-fucopyranoside + H2O = phenol + L-fucose
show the reaction diagram
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phenyl-beta-D-galactopyranoside + H2O = phenol + beta-D-galactopyranose
show the reaction diagram
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phenyl-beta-D-glucopyranoside + H2O = phenol + D-glucose
show the reaction diagram
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phenyl beta-D-glucoside 6-phosphate + H2O = phenol + glucose 6-phosphate
show the reaction diagram
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Galbeta(1-3)GalNAcalpha(1-)OC6H5 + H2O = Galbeta(1-3)GalNAc + phenol
show the reaction diagram
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Nalpha-tosyl-L-Tyr benzyl ester + H2O = Nalpha-tosyl-L-Tyr + phenol
show the reaction diagram
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N-tert-butyloxycarbonyl-L-Glu-alpha-phenyl ester + H2O = butyloxycarbonyl-L-Glu + phenol
show the reaction diagram
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Nalpha-benzyloxycarbonyl-Lys-phenyl ester + H2O = Nalpha-benzyloxycarbonyl-Lys + phenol
show the reaction diagram
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N-tert-butyloxycarbonyl-Ala-Ph + L-Ala-p-nitroanilide = N-tert-butyloxycarbonyl-Ala-Ala-p-nitroanilide + phenol
show the reaction diagram
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benzyloxycarbonyl-Lys phenyl ester + H2O = benzyloxycarbonyl + phenol
show the reaction diagram
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p-nitrophenol + H2O = phenol + NH3
show the reaction diagram
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phenylcarbamate + H2O = CO2 + NH3 + phenol
show the reaction diagram
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phenyl acetate + H2O = phenol + acetate
show the reaction diagram
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salicylic acid = phenol + CO2
show the reaction diagram
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4-Hydroxybenzoate = Phenol + CO2
show the reaction diagram
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salicylate = phenol + CO2
show the reaction diagram
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phenol/in + ATP + H2O = phenol/out + ADP + phosphate
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (8 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
mutant Y140T, 88fold activation compared to the wild-type enzyme
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activity positively affected by the presence of 0.018% phenol, ranging from 0.006 to 0.123%
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significantly induces expression of CYP4F3A at both mRNA and protein levels in cultured and differentiated HL-60 cells, in the proerythroid cell line K-562, and ex vivo in human neutrophils
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low concentration, magnitude of activation depends on the nature of the acyl-CoA substrate
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the changes of enzyme activity in vivo are likely to be caused by adaption and compensation processes in the organisms of the molluscs exposed to toxicants
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activates reaction with Gly-Gly-ethyl ester and Gly-Gly-NH2, no effect on reaction with Gly-Phe-NH2
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Inhibitor in Enzyme-catalyzed Reactions (44 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
competitive inhibition
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noncompetitive
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competitive
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inhibition of catalase activity
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phenylalanine residues are vulnerable to modification by phenoxyl radicals. Radical coupling does not change the secondary structure or the active site of HRP isoform C
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0.2 mM, 98% inhibition; 0.2 mM, 98% inhibition
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competitive inhibition
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IC50 of 0.32 vol%
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high concentration, magnitude of inhibition depends on the nature of the acyl-CoA substrate
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5 mM, 45% inhibition
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strong inhibitor
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poor inhibitor of the reverse reaction
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in combination with Tris most potent inhibitor
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the gelatin-immobilized enzyme is not sensitive in contrast to the native enzyme
noncompetitive inhibition, Ki: 112 mM
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Ki: 4 mM
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3.89 mM, 50% inhibition
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3D Structure of Enzyme-Ligand-Complex (PDB) (154 results)

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EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (21 results)

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EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
38
-
pH 4.5, 55°C
691.7
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native enzyme, at 30°C
0.286
-
25°C, pH not specified in the publication
0.3
-
pH 7.5, 23°C
0.4
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pH 9.0, 37°C, wild-type
48.6
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at pH 8.0, at 25°C
1.1
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pH 5.5, 30°C
0.44
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recombinant enzyme, L-tyrosine formation is measured from phenol, pyruvate, and ammonium, pH 8.5, 20°C

KM Value (53 results)

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EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0427
-
pH 7.5, 40°C
0.00061
-
25°C, pH not specified in the publication
0.00171
-
pH 7.0, 35°C
0.253
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pH 7.5, 23°C
0.05
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pH 9.0, 37°C, wild-type
0.92
-
pH 5.5, 37°C
123
-
pH 5.5, 30°C

Ki Value (40 results)

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EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
11
-
pH 7.0, 45°C
0.7
-
-
21
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at pH 7.0 and 55°C
6
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at pH 7.0
21
-
-
0.14
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catalase activity, pH 8.5, 30°C
112
-
noncompetitive inhibition
2.1
-
25°C, pH 8.8

References & Links

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Links to other databases for phenol

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EXTERNAL LINKS
ChEBI
PubChem
UniChem