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Information on EC 1.6.5.6 - p-benzoquinone reductase (NADPH)
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1.6.5.6 p-benzoquinone reductase (NADPH)IUBMB Comments
Involved in the 4-nitrophenol degradation pathway in bacteria.
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Word Map
- 1.6.5.6
- reductases
- ketone
-
nadph-dependent
- menadione
-
enantioselectivity
-
aldo-keto
-
enantiomeric
-
1.1.1.184
- parapsilosis
- 4-chloro-3-oxobutanoate
- quercitrin
- 4-benzoylpyridine
-
s-4-chloro-3-hydroxybutanoate
- 9,10-phenanthrenequinone
-
bioreduction
-
space-time
-
dihydrodiol
-
prochiral
-
anti-prelog
-
coenzyme-binding
- acetohexamide
- acetophenone
- dicoumarol
- salmonicolor
-
sporobolomyces
- doxorubicinol
- sepiapterin
- stipitis
- 2-hydroxyacetophenone
- l-xylulose
- environmental protection
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Synonyms
carbonyl reductase, mnpa2, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
carbonyl reductase
-
-
-
-
MnpA2
PnpB
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
NADPH + H+ + p-benzoquinone = NADP+ + hydroquinone
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
-
-
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SYSTEMATIC NAME
IUBMB Comments
NADPH:p-benzoquinone oxidoreductase
Involved in the 4-nitrophenol degradation pathway in bacteria.
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CAS REGISTRY NUMBER
COMMENTARY
9032-20-6
-
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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
acenaphthenequinone + NADPH
NADP+ + acenaphthylene-1,2-diol
-
reduced velocity
-
ir
dihydro-4-methyl-4-propyl-2,3-furanedione + NADPH
NADP+ + 4-methyl-4-propyl-4,5-dihydrofuran-2,3-diol
-
-
-
ir
dihydro-5-(2-butyl)-4-methyl-4-ethyl-2,3-furanedione + NADPH
NADP+ + 5-sec-butyl-4-ethyl-4-methyl-4,5-dihydrofuran-2,3-diol
-
reduced velocity
-
ir
dihydro-5-(2-pentyl)-4,4-dimethyl-2,3-furanedione + NADPH
NADP+ + 4,4-dimethyl-5-(1-methylbutyl)-4,5-dihydrofuran-2,3-diol
-
-
-
ir
dihydro-5-(2-pentyl)-4-methyl-4-propyl-2,3-furanedione + NADPH
NADP+ + 4-methyl-5-(1-methylbutyl)-4-propyl-4,5-dihydrofuran-2,3-diol
-
reduced velocity
-
ir
dihydro-5-(3-pentyl)-4,4-dimethyl-2,3-furanedione + NADPH
NADP+ + 5-(1-ethylpropyl)-4,4-dimethyl-4,5-dihydrofuran-2,3-diol
-
-
-
ir
dihydro-5-isopropyl-4,4-dimethyl-2,3-furanedione + NADPH
NADP+ + 5-isopropyl-4,4-dimethyl-4,5-dihydrofuran-2,3-diol
-
-
-
ir
NADPH + H+ + chloro-1,4-benzoquinone
NADP+ + chlorohydroquinone
-
-
-
-
?
NADPH + H+ + methyl-1,4-benzoquinone
NADP+ + methylhydroquinone
-
-
-
-
?
additional information
?
-
-
strain WBC-3 can completely degrade both 4-nitrophenol and 4-nictrocatechol when 4-nitrophenol is used as the inducer
-
-
?
alpha-naphthoquinone + NADPH
NADP+ + naphthalene-1,4-diol
-
-
-
ir
beta-naphthoquinone + NADPH
NADP+ + naphthalene-1,2-diol
-
-
-
ir
methyl-4-benzoquinone + NADPH + H+
NADP+ + methyl hydroquinone
-
-
-
?
p-toluquinone + NADPH + H+
NADP+ + 2-methylbenzene-1,4-diol
-
-
-
-
ir
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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
additional information
?
-
-
strain WBC-3 can completely degrade both 4-nitrophenol and 4-nictrocatechol when 4-nitrophenol is used as the inducer
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
FMN
enzyme is flavin mononucleotide-dependent, FMN is preferred to FAD
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
Alzheimer Disease
Increased brain protein levels of carbonyl reductase and alcohol dehydrogenase in Down syndrome and Alzheimer's disease.
Asthma
Vasoactive Intestinal Peptide Knockout (VIP KO) mouse model of sulfite-sensitive asthma: up-regulation of novel lung carbonyl reductase.
Breast Neoplasms
Carbonyl reductase and NADPH cytochrome P450 reductase activities in human tumoral versus normal tissues.
Breast Neoplasms
Reduction of doxorubicin and oracin and induction of carbonyl reductase in human breast carcinoma MCF-7 cells.
Breast Neoplasms
[Assessment of the concentrations of carbonylated proteins and carbonyl reductase enzyme in mexican women with breast cancer: A pilot study].
Carcinogenesis
Candidate gene and mechanism investigations in congenital obstructive nephropathy based on bioinformatics analysis.
Carcinoma
Increased resistance of tumor cells to daunorubicin after transfection of cDNAs coding for anthracycline inactivating enzymes.
Carcinoma
Suppression of carbonyl reductase expression enhances malignant behaviour in uterine cervical squamous cell carcinoma: Carbonyl reductase predicts prognosis and lymph node metastasis.
Carcinoma
Tumor-related protein, the squamous cell carcinoma antigen binds to the intracellular protein carbonyl reductase.
Carcinoma, Hepatocellular
Decreased expression of the human carbonyl reductase 2 gene HCR2 in hepatocellular carcinoma.
Carcinoma, Hepatocellular
Decreased expression of the peroxisomal bifunctional enzyme and carbonyl reductase in human hepatocellular carcinomas.
Carcinoma, Ovarian Epithelial
Carbonyl reductase as a significant predictor of survival and lymph node metastasis in epithelial ovarian cancer.
Carcinoma, Squamous Cell
Suppression of carbonyl reductase expression enhances malignant behaviour in uterine cervical squamous cell carcinoma: Carbonyl reductase predicts prognosis and lymph node metastasis.
Carcinoma, Squamous Cell
Tumor-related protein, the squamous cell carcinoma antigen binds to the intracellular protein carbonyl reductase.
Cardiomyopathies
Anthracycline-Related Cardiomyopathy After Childhood Cancer: Role of Polymorphisms in Carbonyl Reductase Genes--A report From the Children's Oncology Group.
Cardiotoxicity
Flavonoids as protectors against doxorubicin cardiotoxicity: role of iron chelation, antioxidant activity and inhibition of carbonyl reductase.
Cardiotoxicity
Human carbonyl reductase overexpression in the heart advances the development of doxorubicin-induced cardiotoxicity in transgenic mice.
Cardiotoxicity
Modeling the metabolism of idarubicin to idarubicinol in rat heart: effect of rutin and phenobarbital.
Cardiotoxicity
Protection from doxorubicin-induced cardiac toxicity in mice with a null allele of carbonyl reductase 1.
Cardiotoxicity
Single-nucleotide polymorphisms in aldo-keto and carbonyl reductase genes are not associated with acute cardiotoxicity after daunorubicin chemotherapy.
Down Syndrome
Human carbonyl reductase (CBR) localized to band 21q22.1 by high-resolution fluorescence in situ hybridization displays gene dosage effects in trisomy 21 cells.
Down Syndrome
Increased brain protein levels of carbonyl reductase and alcohol dehydrogenase in Down syndrome and Alzheimer's disease.
Fatty Liver
A novel NAD(P)H-dependent carbonyl reductase specifically expressed in the thyroidectomized chicken fatty liver: catalytic properties and crystal structure.
Fatty Liver
Expression, purification, crystallization and preliminary X-ray analysis of NAD(P)H-dependent carbonyl reductase specifically expressed in thyroidectomized chicken fatty liver.
glucose-6-phosphate dehydrogenase (nadp+) deficiency
Glucose-6-phosphate dehydrogenase deficiency severely restricts the biotransformation of daunorubicin in human erythrocytes.
Glucosephosphate Dehydrogenase Deficiency
Glucose-6-phosphate dehydrogenase deficiency severely restricts the biotransformation of daunorubicin in human erythrocytes.
Kidney Failure, Chronic
Downregulation of Hepatic Carbonyl Reductase Type 1 in End-Stage Renal Disease.
Leukemia
Protection against daunorubicin cytotoxicity by expression of a cloned human carbonyl reductase cDNA in K562 leukemia cells.
Lung Neoplasms
Carbonyl reductase expression and its clinical significance in non-small-cell lung cancer.
Lymphatic Metastasis
Carbonyl reductase as a significant predictor of survival and lymph node metastasis in epithelial ovarian cancer.
Lymphatic Metastasis
Suppression of carbonyl reductase expression enhances malignant behaviour in uterine cervical squamous cell carcinoma: Carbonyl reductase predicts prognosis and lymph node metastasis.
Neoplasm Metastasis
Carbonyl reductase as a significant predictor of survival and lymph node metastasis in epithelial ovarian cancer.
Neoplasm Metastasis
Suppression of carbonyl reductase expression enhances malignant behaviour in uterine cervical squamous cell carcinoma: Carbonyl reductase predicts prognosis and lymph node metastasis.
Neoplasm Metastasis
Towards a lung adenocarcinoma proteome map: studies with SP-C/c-raf transgenic mice.
Neoplasms
Anthracycline-Related Cardiomyopathy After Childhood Cancer: Role of Polymorphisms in Carbonyl Reductase Genes--A report From the Children's Oncology Group.
Neoplasms
Carbonyl reductase and NADPH cytochrome P450 reductase activities in human tumoral versus normal tissues.
Neoplasms
Carbonyl reductase inactivation may contribute to mouse lung tumor promotion by electrophilic metabolites of butylated hydroxytoluene: protein alkylation in vivo and in vitro.
Neoplasms
CBR1 and CBR3 pharmacogenetics and their influence on doxorubicin disposition in Asian breast cancer patients.
Neoplasms
Chemopreventive agents modulate the protein expression profile of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone plus benzo[a]pyrene-induced lung tumors in A/J mice.
Neoplasms
Clofibric acid, a peroxisome proliferator-activated receptor alpha ligand, inhibits growth of human ovarian cancer.
Neoplasms
Malignant ovarian tumors with induced expression of carbonyl reductase show spontaneous regression.
Neoplasms
Protection against daunorubicin cytotoxicity by expression of a cloned human carbonyl reductase cDNA in K562 leukemia cells.
Neoplasms
Temporal and spatial patterns of ovarian gene transcription following an ovulatory dose of gonadotropin in the rat.
Neoplasms
The role of cytochromes p450 and aldo-keto reductases in prognosis of breast carcinoma patients.
Neoplasms
Towards a lung adenocarcinoma proteome map: studies with SP-C/c-raf transgenic mice.
Ovarian Neoplasms
Malignant ovarian tumors with induced expression of carbonyl reductase show spontaneous regression.
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0149
p-benzoquinone
-
pH 7.4, temperature not specified in the publication
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7.2
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
metabolism
-
the enzyme is involved in the initial steps of 4-nitrophenol catabolism via hydroquinone
physiological function
physiological function
PnpB enhances the p-nitrophenol degradation by p-nitrophenol 4-monooxygenase
physiological function
-
enzyme is able to enhance 4-nitrophenol 4-monooxygenase PnpA activity in vitro in the conversion of 2-chloro-4-nitrophenol to chloro-1,4-benzoquinone
physiological function
-
methyl-1,4-benzoquinone and methylhydroquinone are the intermediates before ring cleavage during 3-methyl-4-nitrophenol degradation, with a nearly stoichiometric formation of methyl-1,4-benzoquinone and methylhydroquinone from 3-methyl-4-nitrophenol
physiological function
strain TSN1 degrades 3-methyl-4-nitrophenol via methyl-4-benzoquinone, methyl hydroquinone, and 2-hydroxy-5-methyl-1,4-benzoquinone in combination with 4-nitrophenol monooxygenase and the 4-benzoquinone reductase MnpA1 and MnpA2 and meta-cleaving dioxygenase gene and amonooxygenase MnpC and MnpB
physiological function
Pseudomonas putida TSN1
-
strain TSN1 degrades 3-methyl-4-nitrophenol via methyl-4-benzoquinone, methyl hydroquinone, and 2-hydroxy-5-methyl-1,4-benzoquinone in combination with 4-nitrophenol monooxygenase and the 4-benzoquinone reductase MnpA1 and MnpA2 and meta-cleaving dioxygenase gene and amonooxygenase MnpC and MnpB
-
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). A0A2S5BCV3_9BASI
1192
0
124910
TrEMBL
other Location (Reliability: 1)
A0A2K4X821_PSEVC
184
0
19779
TrEMBL
-
A0A644V598_9ZZZZ
168
0
17770
TrEMBL
other Location (Reliability: 4)
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
dimer
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pH STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6 - 7
-
91% of control activity at pH 9, 79% of control activity at pH 12, no activity at pH 4.0
288624
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TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
environmental protection
-
the strain WBC3, also possessing 4-nitrophenyl 4-monooxygenase activity through PnpA, has a potential in bioremediation of the environment polluted by both 4-nitrocatechol and 4-nitrophenol
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Kolesnikov, P.A.; Zore, S.V.; Pshenova, K.V.; Petrochenko, E.I.; Pletnikova, N.K.; Makovkina, L.E.; Mutuskin, A.A.
Localization of NADH2(NADPH2): p-benzoquinone oxidoreductases in cell fractions of pea leaves
Fiziol. Rast. (Moscow)
20
170-174
1973
Pisum sativum
-
brenda
Shimizu, S.; Hattori, S.; Hata, H.; Yamada, H.
A novel fungal enzyme, NADPH-dependent carbonyl reductase, showing high specificity to conjugated polyketones
Eur. J. Biochem.
174
37-44
1988
Mucor ambiguus, Mucor ambiguus AKU 3006
brenda
Requejo, R.; Tena, M.
Proteome analysis of maize roots reveals that oxidative stress is a main contributing factor to plant arsenic toxicity
Phytochemistry
66
1519-1528
2005
Zea mays
brenda
Zhang, J.J.; Liu, H.; Xiao, Y.; Zhang, X.E.; Zhou, N.Y.
Identification and characterization of catabolic para-nitrophenol 4-monooxygenase and para-benzoquinone reductase from Pseudomonas sp. strain WBC-3
J. Bacteriol.
191
2703-2710
2009
Pseudomonas sp. WBC-3 (C1I202)
brenda
Wei, M.; Zhang, J.J.; Liu, H.; Zhou, N.Y.
para-Nitrophenol 4-monooxygenase and hydroxyquinol 1,2-dioxygenase catalyze sequential transformation of 4-nitrocatechol in Pseudomonas sp. strain WBC-3
Biodegradation
21
915-921
2010
Pseudomonas sp.
brenda
Min, J.; Zhang, J.J.; Zhou, N.Y.
The gene cluster for para-nitrophenol catabolism is responsible for 2-chloro-4-nitrophenol degradation in Burkholderia sp. strain SJ98
Appl. Environ. Microbiol.
80
6212-6222
2014
Burkholderia sp. SJ98
brenda