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Enzyme Nomenclature
Information on EC 1.14.13.29 - 4-nitrophenol 2-monooxygenase
Word Map on EC 1.14.13.29
- 1.14.13.29
- hepatic
- cyp2e1
-
ethoxyresorufin
- n-demethylase
- cyp1a2
- aniline
-
prod
-
pentoxyresorufin
-
n-nitrosodimethylamine
-
o-dealkylase
-
diallyl
-
cyp2e1-mediated
- 4-nitrocatechol
-
o-deethylation
- chlorzoxazone
- benzphetamine
- 4-methylpyrazole
-
cyp2e1-dependent
-
2e1-dependent
-
o-depentylase
-
benzyloxyresorufin
- medicine
-
ethoxycoumarin
-
acetone-induced
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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
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EC NUMBER 
COMMENTARY 
1.14.13.29
-
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RECOMMENDED NAME
GeneOntology No.
4-nitrophenol 2-monooxygenase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
4-nitrophenol + NADH + H+ + O2 = 4-nitrocatechol + NAD+ + H2O
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
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-
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redox reaction
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-
-
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reduction
-
-
-
-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
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SYSTEMATIC NAME
IUBMB Comments
4-nitrophenol,NADH:oxygen oxidoreductase (2-hydroxylating)
A flavoprotein (FAD).
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CAS REGISTRY NUMBER
COMMENTARY
91116-87-9
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
male Swiss Webster mice infected by malaria pathogen Plasmodium berghei ANKA
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p-nitrophenol hydroxylase component A; strain DS001 isolated from soil, MTCC 4830
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-
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
metabolism
NphA1 oxidizes 4-nitrophenol into 4-nitrocatechol in the presence of FAD, NADH and NphA2 (reduces FAD in the presence of NADH)
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
3-nitrophenol + NADH + H+ + O2
4-nitrocatechol + NAD+ + H2O
1 mM NADH, 5 M FAD, 1 mM DTT, NphA1 (approximately 0.5 mg of purified protein), and NphA2 (approximately 0.1 mg of purified protein) in 1 ml of 50 mM Tris-HCl buffer, pH 8.0, slow degradation of substrate
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-
?
4-chlorophenol + NADH + H+ + O2
4-chlorocatechol + NAD+ + H2O
1 mM NADH, 5 M FAD, 1 mM DTT, NphA1 (approximately 0.5 mg of purified protein), and NphA2 (approximately 0.1 mg of purified protein) in 1 ml of 50 mM Tris-HCl buffer, pH 8.0
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-
?
4-nitrocatechol + NADH + H+ + O2
4-nitrobenzene-1,2,3-triol + NAD+ + H2O
1 mM NADH, 5 M FAD, 1 mM DTT, NphA1 (approximately 0.5 mg of purified protein), and NphA2 (approximately 0.1 mg of purified protein) in 1 ml of 50 mM Tris-HCl buffer, pH 8.0, very slow degradation of substrate, no unambiguous identification of products by HPLC due to overlaps
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-
?
p-nitrophenol + NADPH + H+ + O2
p-nitrocatechol + NADP+ + H2O
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200 microM substrate, 0.4 mg microsomal protein, 1 mM NADPH
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-
?
phenol + NADH + H+ + O2
catechol + NAD+ + H2O
1 mM NADH, 5 M FAD, 1 mM DTT, NphA1 (approximately 0.5 mg of purified protein), and NphA2 (approximately 0.1 mg of purified protein) in 1 ml of 50 mM Tris-HCl buffer, pH 8.0
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-
?
4-nitrophenol + NADH + H+ + O2
4-nitrocatechol + NAD+ + H2O
in the presence of FAD and histidin-tagged NphA2
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-
?
4-nitrophenol + NADH + H+ + O2
4-nitrocatechol + NAD+ + H2O
1 mM NADH, 5 M FAD, 1 mM DTT, NphA1 (approximately 0.5 mg of purified protein), and NphA2 (approximately 0.1 mg of purified protein) in 1 ml of 50 mM Tris-HCl buffer, pH 8.0
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-
?
4-nitrophenol + NADH + H+ + O2
4-nitrocatechol + NAD+ + H2O
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catalyzed by p-nitrophenol hydroxylase component A
GC-MS product identification
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?
4-nitrophenol + NADH + O2
4-nitrocatechol + NAD+ + H2O
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NADPH: 50% of the activity with NADH
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?
additional information
?
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no substrates: 2-nitrophenol, 2,4-dinitrophenol
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additional information
?
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no degradation of 2-nitrophenol, 2-hydroxyphenylacetate, 3-hydroxyphenylacetate, 4-hydroxyphenylacetate
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
p-nitrophenol + NADPH + H+ + O2
p-nitrocatechol + NADP+ + H2O
-
200 microM substrate, 0.4 mg microsomal protein, 1 mM NADPH
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-
?
4-nitrophenol + NADH + H+ + O2
4-nitrocatechol + NAD+ + H2O
Q8RQQ0
in the presence of FAD and histidin-tagged NphA2
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-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
FAD
inhibition at concentrations higher than 10 microM FAD, complete inhibition at concentrations higher than 50 microM FAD
sesamin
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mechanism-based inhibition with decrease in the IC50 value when 5 min pre-incubation step is included
sesamin
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mechanism-based inhibition with decrease in the IC50 value when 5 min pre-incubation step is included
additional information
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inhibition at high ionic strength of all common buffers and salts e.g. phosphate, Tris, KCl, (NH4)2SO4, 60% inhibition above 300 mM, crude enzyme extract
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additional information
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no inhibitory effects of testosterone (4, 8, 17, 34 pmol/ml), 17beta-estradiol (18, 3.6, 36, 72 pmol/ml), estrone (1.9, 3.7, 9, 18 pmol/ml), androstenone (55, 180, 3760, 7520 pmol/ml)
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
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chronic abuse aspartame leads to 1.5fold increased enyzme activity in cerebrum and 25-fold in cerebellum, pattern of induction of CYP immunoreactive proteins, specific induction in the brain, not in hepatocytes, overview
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additional information
only inducer of nphA1 expression is 4-nitrophenol, no induction of nphA1 gene expression (in the presence of regulator NphR) by phenol, 2-nitrophenol, 3-nitrophenol, 2-hydroxyphenylacetate, 3-hydroxyphenylacetate, 4-hydroxyphenylacetate, 4-nitrocatechol
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.127
4-nitrophenol
Oryctolagus cuniculus
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reconstituted system of purified isozyme 3a, dilaroylglyceryl-3-phosphorylcholine and NADPH-cytochrome P-450 reductase at pH 7.6
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
11.2
cell extract, 0.3 mM 4-nitrophenol as substrate, 1 mM NADH, 5 M FAD, 1 mM DTT, NphA1 (approximately 0.5 mg of purified protein), and NphA2 (approximately 0.1 mg of purified protein) in 1 ml of 50 mM Tris-HCl buffer (pH 7.5), 22°C
24.5
HiTrap Q-Sepharose purified enzyme, 0.3 mM 4-nitrophenol as substrate, 1 mM NADH, 5 M FAD, 1 mM DTT, NphA1 (approximately 0.5 mg of purified protein), and NphA2 (approximately 0.1 mg of purified protein) in 1 ml of 50 mM Tris-HCl buffer (pH 7.5), 22°C
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6.8
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
additional information
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strain DS001 utilizes methyl parathion, p-nitrophenol, 4-nitrocatechol, and 1,2,4-benzenetriol as sole carbon and energy sources but cannot grow using hydroquinone as a source of carbon
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
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ORGANIC SOLVENT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Glycerol
more than 80% activity can be kept at least for a week in the presence of 20% glycerol at -20°C
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
0-4°C, 30% loss of activity after 7 days, 70% loss of activity after 14 days, crude enzyme extract
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
cells centrifuged, washed with TD buffer (50 mM Tris-HCl, 1 mM dithiothreitol (DTT), pH 7.6), centrifuged, bacterial pellet resuspended in same buffer, sonicated, centrifuged, supernatant used as cell extract or further purified with ion-exchange chromatography with a HiTrap Q-Sepharose column, active fractions are desalted with PD-10 desalting column, concentrated with Vivaspin concentrator
liver is homogenized, centrifuged, supernatant mixed with 8 mM calcium chloride, microsomes separated by centrifugation, pellet resuspended in 50 mM Tris-HCl with 0.1 mM ethylendiaminetetraacetic acid and 20% glycerol, pH 7.4
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
DNA and amino acid sequence determination and analysis, phylogenetic analysis
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PCR-amplification, shuttle vector pK4 is used to construct pKPN plasmids containing enzyme gene and reporter gene, hosts are Rhodococcus sp. PN1 and Rhodococcus rhodochrous ATCC 12674 (electroporation), Escherichia coli JM109 is host for propagation and purification of recombinant plasmids
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
medicine
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malaria decreases the activity of p-nitrophenol-hydroxylase in liver microsomes by 33%, mRNA levels are lowered compared to uninfected mice
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LINKS TO OTHER DATABASES (specific for EC-Number 1.14.13.29)
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