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Information on EC 1.14.13.29 - 4-nitrophenol 2-monooxygenase
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1.14.13.29 4-nitrophenol 2-monooxygenaseIUBMB Comments
A flavoprotein (FAD).
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Word Map
- 1.14.13.29
- cyp2e1
- n-demethylase
-
ethoxyresorufin
- cyp1a2
- aniline
-
pentoxyresorufin
-
prod
-
o-dealkylase
-
diallyl
- n-nitrosodimethylamine
- chlorzoxazone
- aminopyrine
-
o-depentylase
- 4-methylpyrazole
-
cyp2e1-dependent
- benzphetamine
-
benzyloxyresorufin
-
cyp2e1-mediated
-
acetone-induced
-
cyp-dependent
-
o-deethylation
-
2e1-dependent
- 7-ethoxyresorufin-o-deethylase
-
ethoxycoumarin
- medicine
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Synonyms
cyp 2e1, p-nitrophenol hydroxylase, cytochrome p-450 2e1, 4-nitrophenol hydroxylase, npha1, p-nitrophenol-hydroxylase, cytochrome p-450 isozyme 3a, 4-nph, pnpa1, pnp monooxygenase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
4-nitrophenol 4-monooxygenase/4-nitrocatechol 2-monooxygenase
4-nitrophenol hydroxylase
4-nitrophenol-2-hydroxylase
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CYP 2E1
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CYP2E1
cytochrome P-450 2E1
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cytochrome P-450 isozyme 3a
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oxygenase, 4-nitrophenol 2-mono-
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PNP 2-monooxygenase
PNP monooxygenase
PnpA1
PNPH
PPH
two-component 4-nitrophenol hydroxylase
NphA1 (oxidase component) and NphA2 (flavin reductase component)
two-component PNP monooxygenase
4-nitrophenol 4-monooxygenase/4-nitrocatechol 2-monooxygenase
UniProt
4-nitrophenol 4-monooxygenase/4-nitrocatechol 2-monooxygenase
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UniProt
4-nitrophenol 4-monooxygenase/4-nitrocatechol 2-monooxygenase
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UniProt
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4-nitrophenol hydroxylase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
4-nitrophenol + NADH + H+ + O2 = 4-nitrocatechol + NAD+ + H2O
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4-nitrophenol + NADH + H+ + O2 = 4-nitrocatechol + NAD+ + H2O
proposed catalytic mechanism of PNP 2-monooxygenase, PnpA1, overview
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4-nitrophenol + NADH + H+ + O2 = 4-nitrocatechol + NAD+ + H2O
proposed catalytic mechanism of PNP 2-monooxygenase, PnpA1, overview
Rhodococcus opacus JCM 13270
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4-nitrophenol + NADH + H+ + O2 = 4-nitrocatechol + NAD+ + H2O
proposed catalytic mechanism of PNP 2-monooxygenase, PnpA1, overview
Rhodococcus opacus RKJ300
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
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redox reaction
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reduction
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PATHWAY SOURCE
PATHWAYS
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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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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 + NADPH + H+ + O2
4-nitrobenzene-1,2,3-triol + NADP+ + H2O
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-
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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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?
2-chloro-4-nitrophenol + NADH + H+ + O2
2-chloro-4-nitrocatechol + NAD+ + H2O
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-
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?
2-chloro-4-nitrophenol + NADH + H+ + O2
2-chloro-4-nitrocatechol + NAD+ + H2O
Rhodococcus opacus JCM 13270
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?
2-chloro-4-nitrophenol + NADH + H+ + O2
2-chloro-4-nitrocatechol + NAD+ + H2O
Rhodococcus opacus RKJ300
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?
2-chloro-4-nitrophenol + NADPH + O2
1,2,4-trihydroxybenzene + ?
Rhodococcus opacus JCM 13270
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?
4-nitrocatechol + NADH + H+ + O2
4-nitrobenzene-1,2,3-triol + NAD+ + H2O
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?
4-nitrocatechol + NADH + H+ + O2
4-nitrobenzene-1,2,3-triol + NAD+ + H2O
Rhodococcus opacus JCM 13270
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?
4-nitrocatechol + NADH + H+ + O2
4-nitrobenzene-1,2,3-triol + NAD+ + H2O
Rhodococcus opacus RKJ300
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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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?
4-nitrophenol + NAD(P)H + H+ + O2
4-nitrocatechol + NAD(P)+ + H2O
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?
4-nitrophenol + NAD(P)H + H+ + O2
4-nitrocatechol + NAD(P)+ + H2O
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?
4-nitrophenol + NAD(P)H + H+ + O2
4-nitrocatechol + NAD(P)+ + H2O
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?
4-nitrophenol + NAD(P)H + H+ + O2
4-nitrocatechol + NAD(P)+ + H2O
Rhodococcus opacus RKJ300
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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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PnpA1 is the oxygenase component of the two-component PNP 2-monooxygenase from Gram-positive Rhodococcus imtechensis strain RKJ300. It also catalyzes the hydroxylation of 4-nitrocatechol (4NC) and 2-chloro-4-nitrophenol (2C4NP)
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additional information
?
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Rhodococcus opacus JCM 13270
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PnpA1 is the oxygenase component of the two-component PNP 2-monooxygenase from Gram-positive Rhodococcus imtechensis strain RKJ300. It also catalyzes the hydroxylation of 4-nitrocatechol (4NC) and 2-chloro-4-nitrophenol (2C4NP)
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additional information
?
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Rhodococcus opacus RKJ300
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PnpA1 is the oxygenase component of the two-component PNP 2-monooxygenase from Gram-positive Rhodococcus imtechensis strain RKJ300. It also catalyzes the hydroxylation of 4-nitrocatechol (4NC) and 2-chloro-4-nitrophenol (2C4NP)
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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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?
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NATURAL SUBSTRATE
NATURAL 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
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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?
4-nitrophenol + NAD(P)H + H+ + O2
4-nitrocatechol + NAD(P)+ + H2O
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?
4-nitrophenol + NAD(P)H + H+ + O2
4-nitrocatechol + NAD(P)+ + H2O
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?
4-nitrophenol + NAD(P)H + H+ + O2
4-nitrocatechol + NAD(P)+ + H2O
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-
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?
4-nitrophenol + NAD(P)H + H+ + O2
4-nitrocatechol + NAD(P)+ + H2O
Rhodococcus opacus RKJ300
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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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-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
FAD
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FAD binding site structure of PnpA1, molecular docking of FAD, overview
FAD
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the si-side of FAD is exposed to solvent, and the re-side faces the substrate-binding site. The loop from positions 449 to 454, loop 187-201, helices alpha13, alpha14, and loop 154-175 are responsible for coordinating FAD. The former three interact with the isoalloxazine ring of FAD, while the latter two interact with the AMP group
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INHIBITOR
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 enzyme 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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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
Adenocarcinoma
Expression of cytochrome P-450 2E1 messenger ribonucleic acid in adenocarcinoma at ureterosigmoidostomy site after bladder exstrophy.
Avitaminosis
Activity of xenobiotic-metabolizing enzymes in the liver of rats with multi-vitamin deficiency.
Bladder Exstrophy
Expression of cytochrome P-450 2E1 messenger ribonucleic acid in adenocarcinoma at ureterosigmoidostomy site after bladder exstrophy.
Brain Edema
[Expression of CYP2E1 in different brain regions during the formation of toxic cerebral edema induced by 1, 2-DCE in mice and its effect on cerebral edema formation].
Carcinogenesis
The effect of rosmarinic acid on 1,2-dimethylhydrazine induced colon carcinogenesis.
Carcinoma, Hepatocellular
Characterization of cytochrome P450 2E1 induction in a rat hepatoma FGC-4 cell model by ethanol.
Carcinoma, Hepatocellular
Expression of Cytochromes P-450 2E1, 3A4 and 1A1/1A2 in Growing and Confluent Human HepG2 Hepatoma Cells-Effect of Ethanol.
Carcinoma, Hepatocellular
Post-translational inhibition of cytochrome P-450 2E1 expression by chlomethiazole in Fao hepatoma cells.
Carcinoma, Hepatocellular
Role of ethanol-inducible cytochrome P-450 2E1 in the development of hepatocellular carcinoma by the chemical carcinogen, N-nitrosodimethylamine.
Carcinoma, Hepatocellular
Selective fast degradation of cytochrome P-450 2E1 in serum-deprived hepatoma cells by a mechanism sensitive to inhibitors of vesicular transport.
Cardiomyopathy, Dilated
New Molecular Mechanism Underlying Myc-Mediated Cytochrome P450 2E1 Upregulation in Apoptosis and Energy Metabolism in the Myocardium.
Cardiomyopathy, Hypertrophic
New Molecular Mechanism Underlying Myc-Mediated Cytochrome P450 2E1 Upregulation in Apoptosis and Energy Metabolism in the Myocardium.
Chemical and Drug Induced Liver Injury
Cytochrome P450 2E1 genotype and the susceptibility to antituberculosis drug-induced hepatitis.
Colonic Neoplasms
Colorectal cancer risk in relation to genetic polymorphism of cytochrome P450 1A1, 2E1, and glutathione-S-transferase M1 enzymes.
Colorectal Neoplasms
Association between allelic polymorphisms of metabolizing enzymes (CYP 1A1, CYP 1A2, CYP 2E1, mEH) and occurrence of colorectal cancer in Hungary.
Colorectal Neoplasms
Colorectal cancer risk in relation to genetic polymorphism of cytochrome P450 1A1, 2E1, and glutathione-S-transferase M1 enzymes.
Endotoxemia
Microsomal Ethanol-Oxidizing System: Success Over 50 Years and an Encouraging Future.
Fatty Liver
Detection of carcinogenic etheno-DNA adducts in children and adolescents with non-alcoholic steatohepatitis (NASH).
Heart Diseases
New Molecular Mechanism Underlying Myc-Mediated Cytochrome P450 2E1 Upregulation in Apoptosis and Energy Metabolism in the Myocardium.
Hepatitis
Minimal effect of cytokine-independent hepatitis induced by anti-Fas antibodies on hepatic cytochrome P450 gene expression in mice.
Liver Diseases
Hepatic Lipid Peroxidation and Cytochrome P-450 2E1 in Pediatric Nonalcoholic Fatty Liver Disease and Its Subtypes.
Liver Diseases, Alcoholic
Lipopolysaccharide-induced liver injury in rats treated with the CYP2E1 inducer pyrazole.
Liver Diseases, Alcoholic
Role of cytochrome P-450 2E1 in ethanol-, carbon tetrachloride- and iron-dependent microsomal lipid peroxidation.
Lung Injury
Selective inhibition and induction of CYP activity discriminates between the isoforms responsible for the activation of butylated hydroxytoluene and naphthalene in mouse lung.
Malnutrition
Effects of chronic ethanol on growth hormone secretion and hepatic cytochrome P450 isozymes of the rat.
Myocardial Ischemia
New Molecular Mechanism Underlying Myc-Mediated Cytochrome P450 2E1 Upregulation in Apoptosis and Energy Metabolism in the Myocardium.
Neoplasms
Dissimilar characteristics of N-methyl-N-nitrosourea-initiated foci and tumors promoted by dichloroacetic acid or trichloroacetic acid in the liver of female B6C3F1 mice.
Neoplasms
Interaction between cytochrome P-450 2E1 polymorphisms and environmental factors with risk of esophageal and stomach cancers in Chinese.
Neoplasms
The effect of rosmarinic acid on 1,2-dimethylhydrazine induced colon carcinogenesis.
Neoplasms
Zonated expression of cytokines in rat liver: effect of chronic ethanol and the cytochrome P450 2E1 inhibitor, chlormethiazole.
Non-alcoholic Fatty Liver Disease
Analysis of hepatic genes involved in the metabolism of fatty acids and iron in nonalcoholic fatty liver disease.
Non-alcoholic Fatty Liver Disease
Hepatic Lipid Peroxidation and Cytochrome P-450 2E1 in Pediatric Nonalcoholic Fatty Liver Disease and Its Subtypes.
Parkinson Disease
Cytochrome P450 and Parkinson's disease: protective role of neuronal CYP 2E1 from MPTP toxicity.
Starvation
[Effect of starvation and acetone on the enzyme systems of biotransformation and toxicity of xenobiotics--CYP2E1 substrates in rats]
Stomach Neoplasms
Interaction between cytochrome P-450 2E1 polymorphisms and environmental factors with risk of esophageal and stomach cancers in Chinese.
Stomach Neoplasms
Polymorphisms in NEIL-2, APE-1, CYP2E1 and MDM2 Genes are Independent Predictors of Gastric Cancer Risk in a Northern Jiangsu Population (China).
Stomach Neoplasms
[Meta-analysis on association between genetic polymorphisms of cytochrome P450 2E1 and susceptibility to Chinese gastric cancer].
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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
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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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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
male Swiss Webster mice infected by malaria pathogen Plasmodium berghei ANKA
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brenda
p-nitrophenol hydroxylase component A; isolated from soil, MTCC 4830
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brenda