1.14.13.7: phenol 2-monooxygenase (NADPH)
This is an abbreviated version!
For detailed information about phenol 2-monooxygenase (NADPH), go to the full flat file.
Word Map on EC 1.14.13.7
-
1.14.13.7
-
catechols
-
phenol-degrading
-
hydroxylases
-
2,3-dioxygenase
-
trichosporon
-
cutaneum
-
meta-cleavage
-
diiron
-
cresol
-
comamonas
-
2-hydroxymuconic
-
testosteroni
-
haldane
-
coke
-
radioresistens
-
carboxylate-bridged
-
meta-pathway
-
ortho-cleavage
-
methylococcus
-
cis,cis-muconate
-
coking
-
environmental protection
-
industry
-
synthesis
-
degradation
- 1.14.13.7
- catechols
-
phenol-degrading
- hydroxylases
-
2,3-dioxygenase
- trichosporon
- cutaneum
-
meta-cleavage
-
diiron
- cresol
- comamonas
-
2-hydroxymuconic
- testosteroni
-
haldane
-
coke
- radioresistens
-
carboxylate-bridged
-
meta-pathway
-
ortho-cleavage
-
methylococcus
- cis,cis-muconate
-
coking
- environmental protection
- industry
- synthesis
- degradation
Reaction
Synonyms
DmpLNO, flavin containing monooxygenase, LmPH, Mph, MphN, multi-component phenol hydroxylase, multicomponent PH, multicomponent phenol hydroxylase, multicomponent phenol hydroxylase alpha subunit, NCgl2588, oxygenase, phenol 2-mono-, PHE, phenol hydroxylase, phenol o-hydroxylase, PHH, phhY, PHIND, PHO, PHR, single-component PH, SPH
ECTree
Advanced search results
Substrates Products
Substrates Products on EC 1.14.13.7 - phenol 2-monooxygenase (NADPH)
Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
REACTION DIAGRAM
1,3-dihydroxybenzene + NADPH + H+ + O2
? + NADP+ + H2O
-
50.12% activity compared to phenol
-
-
?
2 2-cresol + NADPH + O2
3-methylcatechol + 4-methylcatechol + NADP+ + H2O
-
-
-
-
?
2 2-xylene + 2 NADPH + 2 H+ + 2 O2
2,3-dimethylphenol + 3,4-dimethylphenol + 2 NADP+ + 2 H2O
2 ethynylbenzene + NADPH + 3 O2
2-ethynylphenol + 2-hydroxy-6-oxo-octa-2,4-dien-7-ynoic acid + NADP+ + H2O
2,3,5,6-tetrafluorophenol + O2 + NADPH
3,4,6-trifluoro-2-benzoquinone + NADP+ + F-
-
-
-
?
2-hydroxybenzoic acid + NADPH + H+ + O2
? + NADP+ + H2O
-
15.97% activity compared to phenol
-
-
?
2-naphthol + NADPH + H+ + O2
? + NADP+ + H2O
-
9.75% activity compared to phenol
-
-
?
3-aminophenol + NADPH + H+ + O2
3-aminocatechol + NADP+ + H2O
-
-
-
-
?
3-cresol + NADPH + O2
3-methylcatechol + 4-methylcatechol + NADP+ + H2O
-
-
-
-
?
3-hydroxybenzaldehyde + NADPH + H+ + O2
? + NADP+ + H2O
-
-
-
-
?
3-hydroxybenzoic acid + NADPH + H+ + O2
? + NADP+ + H2O
-
18.53% activity compared to phenol
-
-
?
3-nitrophenol + NADPH + H+ + O2
?
-
about 45% of the activity with phenol
-
-
?
4-bromophenol + NADPH + H+ + O2
4-bromocatechol + NADP+ + H2O
-
-
-
-
?
4-chlorophenol + NADPH + H+ + O2
4-chlorocatechol + NADP+ + H2O
-
-
-
-
?
4-chlorophenol + NADPH + H+ + O2
? + NADP+ + H2O
-
28.6% activity compared to phenol
-
-
?
4-cresol + NADPH + O2
4-methylcatechol + NADP+ + H2O
-
best substrate
-
-
?
4-fluorophenol + NADH + H+ + O2
1,2-dihydroxy-4-fluorobenzene + NAD+ + H2O
-
-
-
-
?
4-fluorophenol + O2 + NADPH
?
-
-
-
-
?
4-hydroxybenzaldehyde + NADPH + H+ + O2
? + NADP+ + H2O
-
-
-
-
?
4-hydroxybenzoic acid + NADPH + H+ + O2
? + NADP+ + H2O
-
14.88% activity compared to phenol
-
-
?
4-hydroxyphenol + NADPH + H+ + O2
?
-
about 120% of the activity with phenol
-
-
?
4-methylphenol + NADH + H+ + O2
1,2-dihydroxy-4-methylbenzene + NAD+ + H2O
-
-
-
-
?
4-nitrophenol + NADPH + H+ + O2
4-nitrocatechol + NADP+ + H2O
-
-
-
-
?
4-nitrophenol + NADPH + H+ + O2
?
-
about 50% of the activity with phenol
-
-
?
dibenzofuran + NADPH + H+ + O2
1,2-dihydroxydibenzofuran + NADP+ + H2O
-
-
-
-
?
hydroquinone + NADPH + H+ + O2
? + NADP+ + H2O
-
48.25% activity compared to phenol
-
-
?
m-chlorophenol + NADPH + O2
4-chloro-benzene-1,2-diol + NADP+ + H2O
-
18% of the activity with phenol
-
-
?
m-cresol + NADPH + H+ + O2
3-methylcatechol + 4-methylcatechol + NADP+
-
-
95% 3-methylcatechol, 5% 4-methylcatechol
-
?
o-chlorophenol + NADPH + O2
3-chloro-benzene-1,2-diol + NADP+ + H2O
-
20% of the activity with phenol
-
-
?
o-cresol + NADPH + O2
3-methylcatechol + NADP+ + H2O
-
37% of the activity with phenol, measured as substrate-dependent oxygen uptake rate by derivatives of Pseudomonas aeruginosa PAO1c carrying the enzyme genes after induction with phenol
-
-
?
p-cresol + NADPH + O2
4-methylcatechol + NADP+ + H2O
-
114% of the activity with phenol
-
-
?
toluene + NADPH + H+ + O2
o-cresol + m-cresol + p-cresol + NADP+
-
-
48% o-cresol, 11% m-cresol, 41% p-cresol
-
?
2,3-dimethylphenol + 3,4-dimethylphenol + 2 NADP+ + 2 H2O
-
-
-
-
?
2 2-xylene + 2 NADPH + 2 H+ + 2 O2
2,3-dimethylphenol + 3,4-dimethylphenol + 2 NADP+ + 2 H2O
-
-
-
-
?
2-ethynylphenol + 2-hydroxy-6-oxo-octa-2,4-dien-7-ynoic acid + NADP+ + H2O
-
-
product identification by GC-MS
-
?
2 ethynylbenzene + NADPH + 3 O2
2-ethynylphenol + 2-hydroxy-6-oxo-octa-2,4-dien-7-ynoic acid + NADP+ + H2O
-
substrate only for phenol-grown cells
-
-
?
2 ethynylbenzene + NADPH + 3 O2
2-ethynylphenol + 2-hydroxy-6-oxo-octa-2,4-dien-7-ynoic acid + NADP+ + H2O
-
-
product identification by GC-MS
-
?
2 ethynylbenzene + NADPH + 3 O2
2-ethynylphenol + 2-hydroxy-6-oxo-octa-2,4-dien-7-ynoic acid + NADP+ + H2O
-
substrate only for phenol-grown cells
-
-
?
2,4-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + H+ + O2
2,4-dichlorocatechol + NADP+ + H2O
Auxenochlorella pyrenoidosa NCIM 2738
-
-
-
-
?
2-aminocatechol + NADP+ + H2O
-
-
-
-
?
2-aminophenol + NADPH + H+ + O2
2-aminocatechol + NADP+ + H2O
Auxenochlorella pyrenoidosa NCIM 2738
-
-
-
-
?
2-chlorocatechol + NADP+ + H2O
-
-
-
-
?
2-chlorophenol + NADPH + H+ + O2
2-chlorocatechol + NADP+ + H2O
Auxenochlorella pyrenoidosa NCIM 2738
-
-
-
-
?
3-ethyl-benzene-1,2-diol + NADP+ + H2O
-
18% of the activity with phenol
-
-
?
2-ethylphenol + NADPH + O2
3-ethyl-benzene-1,2-diol + NADP+ + H2O
-
18% of the activity with phenol
-
-
?
?
-
about 70% of the activity with phenol
-
-
?
2-hydroxyphenol + NADPH + H+ + O2
?
-
about 70% of the activity with phenol
-
-
?
?
-
about 80% of the activity with phenol
-
-
?
2-nitrophenol + NADPH + H+ + O2
?
-
about 80% of the activity with phenol
-
-
?
2-cresol + 3-cresol + 4-cresol + 3 NADP+ + 3 H2O
-
-
-
-
?
3 toluene + 3 NADPH + 3 H+ + 3 O2
2-cresol + 3-cresol + 4-cresol + 3 NADP+ + 3 H2O
-
-
-
-
?
3 toluene + 3 NADPH + 3 H+ + 3 O2
2-cresol + 3-cresol + 4-cresol + 3 NADP+ + 3 H2O
-
-
-
-
?
3 toluene + 3 NADPH + 3 H+ + 3 O2
2-cresol + 3-cresol + 4-cresol + 3 NADP+ + 3 H2O
-
regioselectivity, overview
-
-
?
3 toluene + 3 NADPH + 3 H+ + 3 O2
2-cresol + 3-cresol + 4-cresol + 3 NADP+ + 3 H2O
-
regioselectivity, overview
-
-
?
3 toluene + 3 NADPH + 3 H+ + 3 O2
2-cresol + 3-cresol + 4-cresol + 3 NADP+ + 3 H2O
-
-
-
-
?
1,2-dihydroxy-3,4-dimethylbenzene + NAD+ + H2O
-
85% of the activity with phenol
-
-
?
3,4-dimethylphenol + NADH + H+ + O2
1,2-dihydroxy-3,4-dimethylbenzene + NAD+ + H2O
-
85% of the activity with phenol
-
-
?
?
-
72% of the activity with phenol
-
-
?
3,4-dimethylphenol + NADPH + O2
?
-
72% of the activity with phenol
-
-
?
4-chlorocatechol + NAD+ + H2O
-
15% of the activity with phenol
-
-
?
3-chlorophenol + NADH + H+ + O2
4-chlorocatechol + NAD+ + H2O
-
15% of the activity with phenol
-
-
?
3-fluorophenol + O2 + NADPH
?
-
below pH 6.5 3-fluorophenol is preferentially hydroxylated at the C6 ortho position, at increasing pH the C2 ortho-hydroxylation becomes more predominant
-
-
?
?
-
about 60% of the activity with phenol
-
-
?
3-hydroxyphenol + NADPH + H+ + O2
?
-
about 60% of the activity with phenol
-
-
?
1,2-dihydroxy-4-methylbenzene + NAD+ + H2O
-
-
-
-
?
4-chlorophenol + NADH + H+ + O2
1,2-dihydroxy-4-methylbenzene + NAD+ + H2O
-
-
-
-
?
4-chlorocatechol + NAD+ + H2O
-
27% of the activity with phenol
-
-
?
4-chlorophenol + NADH + H+ + O2
4-chlorocatechol + NAD+ + H2O
-
-
-
?
4-propylcatechol + NAD+ + H2O
-
low activity
-
-
?
4-propylphenol + NADH + H+ + O2
4-propylcatechol + NAD+ + H2O
-
low activity
-
-
?
4-methylcatechol + NAD+ + H2O
-
60% of the activity with phenol
-
-
?
3-methylcatechol + NAD+ + H2O
-
60% of the activity with phenol
-
-
?
4-methylcatechol + NAD+ + H2O
-
60% of the activity with phenol
-
-
?
phenol + NAD(P)H + H+ + O2
catechol + NAD(P)+ + H2O
can tolerate the phenol concentration up to 6 mM, degrades phenol through catechol ortho fission pathway
-
-
?
phenol + NAD(P)H + H+ + O2
catechol + NAD(P)+ + H2O
can tolerate the phenol concentration up to 6 mM, degrades phenol through catechol ortho fission pathway
-
-
?
phenol + NAD(P)H + H+ + O2
catechol + NAD(P)+ + H2O
-
-
-
?
phenol + NAD(P)H + H+ + O2
catechol + NAD(P)+ + H2O
can tolerate the phenol concentration up to 1 mM, harbors the both ortho and meta fission pathways simultaneously
-
-
?
phenol + NAD(P)H + H+ + O2
catechol + NAD(P)+ + H2O
can tolerate the phenol concentration up to 6 mM, harbors the both ortho and meta fission pathways simultaneously
-
-
?
phenol + NAD(P)H + H+ + O2
catechol + NAD(P)+ + H2O
can tolerate the phenol concentration up to 6 mM, degrades phenol through catechol ortho fission pathway
-
-
?
phenol + NAD(P)H + H+ + O2
catechol + NAD(P)+ + H2O
can tolerate the phenol concentration up to 6 mM, degrades phenol through catechol ortho fission pathway
-
-
?
phenol + NAD(P)H + H+ + O2
catechol + NAD(P)+ + H2O
A5YUW2, A5YUW3, A5YUW6, A5YUY2, A5YUY5, A5YUY6, A5YUY7, A5YUZ3, A5YUZ5, A5YUZ6, A5YUZ7, A5YUZ8, A5YUZ9, A5YV00, A5YV01, A5YV02, A5YV03, A5YV04, A5YV05, A5YV06, A5YV08, A5YV10, A5YV11, A5YV12, A5YV13, A5YV14, A5YV15, A5YV16, A5YV18, A5YV19, A5YV20
phenol degradation in the activated sludge depends on the combined activity of a number of redundant species
-
-
?
phenol + NADH + H+ + O2
catechol + NAD+ + H2O
-
activity is reduced by 84% when NADPH is replaced by NADH
-
-
?
phenol + NADH + H+ + O2
catechol + NAD+ + H2O
-
coupling between phenol hydroxylase and toluene/o-xylene monooxygenase optimizes the use of nonhydroxylated aromatic molecules by the draining effect of phenol hydroxylase on the products of oxidation catalyzed by toluene/o-xylene monooxygenase, thus avoiding phenol accumulation
-
-
?
phenol + NADH + H+ + O2
catechol + NAD+ + H2O
-
coupling between phenol hydroxylase and toluene/o-xylene monooxygenase optimizes the use of nonhydroxylated aromatic molecules by the draining effect of phenol hydroxylase on the products of oxidation catalyzed by toluene/o-xylene monooxygenase, thus avoiding phenol accumulation
-
-
?
phenol + NADPH + H+ + O2
catechol + NADP+ + H2O
-
100% activity
-
-
?
phenol + NADPH + H+ + O2
catechol + NADP+ + H2O
-
-
-
-
?
phenol + NADPH + H+ + O2
catechol + NADP+ + H2O
-
the enzyme catalyzes the conversion of phenols to their 2-diol derivatives
-
-
?
phenol + NADPH + H+ + O2
catechol + NADP+ + H2O
-
monitoring the production of catechol in a continuous coupled assay with recombinant catechol 2,3-dioxygenase from Pseudomonas sp. OX1
-
-
?
phenol + NADPH + H+ + O2
catechol + NADP+ + H2O
-
monitoring the production of catechol in a continuous coupled assay with recombinant catechol 2,3-dioxygenase from Pseudomonas sp. OX1
-
-
?
catechol + NADP+ + H2O
-
cytochrome c, 2,6-dichlorophenolindophenol, potassium ferricyanide and nitro blue tetrazolium can act as electron acceptors in vitro
-
-
?
phenol + NADPH + O2
catechol + NADP+ + H2O
-
high phenol degradation activity in vivo in strain TL3, catabolic pathway overview
-
-
?
phenol + NADPH + O2
catechol + NADP+ + H2O
-
high phenol degradation activity in vivo in strain TL3, catabolic pathway overview
-
-
?
phenol + NADPH + O2
catechol + NADP+ + H2O
-
initial step in phenol-degrading pathway
-
-
?
phenol + NADPH + O2
catechol + NADP+ + H2O
-
initial step in phenol-degrading pathway
-
-
?
phenol + NADPH + O2
catechol + NADP+ + H2O
-
-
-
-
?
phenol + NADPH + O2
catechol + NADP+ + H2O
-
reaction mechanism
-
-
?
?
assay at 28°C, pH 6.8-7.0, concentration of phenol diversify from 25 mg/l to 800 mg/l
-
-
?
phenol + O2
?
utilize phenol as sole carbon and energy source, concentration of phenol diversify from 25 mg/l to 1000 mg/l, assay at 28°C, pH 6.8-7.0
-
-
?
phenol + O2
?
utilize phenol as sole carbon and energy source, concentration of phenol diversify from 25 mg/l to 1000 mg/l, assay at 28°C, pH 6.8-7.0
-
-
?
phenol + O2
?
-
assay at 28°C, pH 6.8-7.0, concentration of phenol diversify from 25 mg/l to 800 mg/l
-
-
?
quinol + O2 + NADPH
1,2,4-trihydroxybenzene + NADP+ + H2O
-
-
-
-
?
?
-
-
no PHO activity with p-hydroxybenzoic acid, m-hydroxybenzoic acid, 2,3-dinitrophenol, 3,4-dichlorophenol, 2,4,5-trichlorophenol, 2,2'-dihydroxybiphenyl and L-Tyr
-
-
?
additional information
?
-
-
no PHO activity with p-hydroxybenzoic acid, m-hydroxybenzoic acid, 2,3-dinitrophenol, 3,4-dichlorophenol, 2,4,5-trichlorophenol, 2,2'-dihydroxybiphenyl and L-Tyr
-
-
?
additional information
?
-
-
the enzyme has broad substrate specificity against isomeric diphenols, isomeric methylphenols, halogen-substituted phenols, amino-substituted phenols, nitrophenols, hydroxybenzaldehyde and hydroxylbenzoic acid
-
-
-
additional information
?
-
-
the enzyme has broad substrate specificity against isomeric diphenols, isomeric methylphenols, halogen-substituted phenols, amino-substituted phenols, nitrophenols, hydroxybenzaldehyde and hydroxylbenzoic acid
-
-
?
additional information
?
-
Auxenochlorella pyrenoidosa NCIM 2738
-
the enzyme has broad substrate specificity against isomeric diphenols, isomeric methylphenols, halogen-substituted phenols, amino-substituted phenols, nitrophenols, hydroxybenzaldehyde and hydroxylbenzoic acid
-
-
-
additional information
?
-
-
not: 2,4-, 2,5- and 2,6-dimethylphenols
-
-
?
additional information
?
-
-
broad specificity, reaction results in the formation of the corresponding o-diols
-
-
?
additional information
?
-
-
overview of possible reaction products of fluorinated phenols
-
-
?
additional information
?
-
-
first enzyme of phenol biodegradation
-
-
?
additional information
?
-
-
the enzyme hydroxylates phenol and several different toxic phenol derivatives, e.g. cresols, nitrophenols and hydroxyphenols, substrate specificity, overview
-
-
?
additional information
?
-
-
the enzyme hydroxylates phenol and several different toxic phenol derivatives, e.g. cresols, nitrophenols and hydroxyphenols, substrate specificity, overview
-
-
?
additional information
?
-
-
the enzyme is a hydrocarbon-oxidizing multicomponent monooxygenase, important for activity is formation of a complex between the hydroxylase and a regulatory protein component
-
-
?
additional information
?
-
-
the enzyme is a multicomponent phenol hydroxylase, production of dyes from indole derivatives by recombinant enzymes expressed in Escherichia coli, substrate specificities of the enzyme from strain KL28 and KL33, the products formed by the enzyme from the two strain are different, detailed overview
-
-
?
additional information
?
-
-
only complete enzyme systems containing all three or four protein components are capable of oxidizing phenol. The electron-transfer components exert regulatory effects on substrate oxidation processes taking place at the hydroxylase actives sites, most likely through allostery. The regulatory proteins facilitate the electron-transfer step in the hydrocarbon oxidation cycle in the absence of phenol. Under these conditions, electron consumption is coupled to H2O2 formation in a hydroxylase-dependent manner
-
-
?
additional information
?
-
-
only complete enzyme systems containing all three or four protein components are capable of oxidizing phenol. The electron-transfer components exert regulatory effects on substrate oxidation processes taking place at the hydroxylase actives sites, most likely through allostery. The regulatory proteins facilitate the electron-transfer step in the hydrocarbon oxidation cycle in the absence of phenol. Under these conditions, electron consumption is coupled to H2O2 formation in a hydroxylase-dependent manner
-
-
?
additional information
?
-
-
the enzyme is a hydrocarbon-oxidizing multicomponent monooxygenase, important for activity is formation of a complex between the hydroxylase and a regulatory protein component
-
-
?
additional information
?
-
-
the enzyme hydroxylates benzenes to catechols via the intermediate production of phenols
-
-
?
additional information
?
-
-
the enzyme hydroxylates benzenes to catechols via the intermediate production of phenols
-
-
?