Ligand phenol

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Basic Ligand Information

Molecular Structure
Picture of phenol (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C6H6O
phenol
ISWSIDIOOBJBQZ-UHFFFAOYSA-N
Synonyms:
hydroxybenzene, monophenol, Phenoate, phenols

Show all pahtways known for Show all pathways known for phenol

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (16 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
phenol + O2 = ?
show the reaction diagram
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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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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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In Vivo Product in Enzyme-catalyzed Reactions (5 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
phenylacetate + H2O = phenol + acetate
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-
salicylate = phenol + CO2
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-
L-tyrosine + H2O = phenol + pyruvate + NH3
show the reaction diagram
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-

Substrate in Enzyme-catalyzed Reactions (82 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
phenol + ferricytochrome c = ?
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phenol + O2 = ?
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phenol + H2O2 = ? + H2O
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H2O2 + phenol = ?
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phenol + H2O2 = ?
show the reaction diagram
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phenol + O2 = ?
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phenol + NADPH + H+ + O2 = catechol + NADP+ + H2O
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phenol + NADH + O2 = catechol + hydroquinone + NAD+
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phenol + NADH + H+ + O2 = hydroquinone + ? + NAD+ + H2O
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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
show the reaction diagram
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S-adenosyl-L-methionine + phenol = S-adenosyl-L-homocysteine + anisole
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phenol + S-adenosyl-L-methionine = methoxybenzene + S-adenosyl-L-homocysteine
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acyl-CoA + phenol = ? + CoA
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phenol + palmitoyl-CoA = phenyl palmitate + CoA
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UDP-glucose + phenol = UDP + phenyl-beta-D-glucopyranoside
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UDPglucose + phenol = UDP + phenyl beta-D-glucoside
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UDP-alpha-D-glucose + phenol = UDP + phenyl beta-D-glucopyranoside
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UDP-glucose + phenol = UDP + phenyglucoside
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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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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
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3'-phosphoadenylylsulfate + phenol = adenosine 3',5'-bisphosphate + phenyl sulfate
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phenol/in + ATP + H2O = phenol/out + ADP + phosphate
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Phenol + CO2 = 4-Hydroxybenzoate
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O-acetyl-L-serine + phenol = S-phenyl-L-serine + acetate
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Product in Enzyme-catalyzed Reactions (116 results)

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

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 (40 results)

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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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) (20 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (20 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
38
-
pH 4.5, 55C
691.7
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native enzyme, at 30C
2137
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pH 8.0, temperature not specified in the publication
0.4
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pH 9.0, 37C, wild-type
48.6
-
at pH 8.0, at 25C
1.1
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pH 5.5, 30C

KM Value (44 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0427
-
pH 7.5, 40C
5.429
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pH 8.0, temperature not specified in the publication
0.05
-
pH 9.0, 37C, wild-type
123
-
pH 5.5, 30C
4.4
-
-

Ki Value (35 results)

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

References & Links

Links to other databases for phenol

ChEBI
PubChem
ChEBI
PubChem