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Information on EC 1.6.5.10 - NADPH dehydrogenase (quinone)
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1.6.5.10 NADPH dehydrogenase (quinone)IUBMB Comments
A flavoprotein [1, 2]. The enzyme from Escherichia coli is specific for NADPH and is most active with quinone derivatives and ferricyanide as electron acceptors .
Menaquinone can act as acceptor. The enzyme from hog liver is inhibited by dicoumarol and folic acid derivatives but not by 2,4-dinitrophenol .
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Word Map
- 1.6.5.10
- neutrophil
- endothelial
- p47phox
- phagocyte
- apocynin
- dismutase
- artery
- gp91phox
- cardiovascular
- nicotinamide
- hypertension
- angiotensin
- catalase
- oxidases
- cardiac
- leukocyte
-
phorbol
- monocyte
- mapks
- sod
- aortic
- granulomatous
- diphenyleneiodonium
-
diphenylene
- pma
- iodonium
- rac1
- atherosclerosis
-
chemiluminescence
-
phagocytosis
- xanthine
-
polymorphonuclear
- myristate
- microglial
- myeloperoxidase
-
ii-induced
- dihydroethidium
-
endothelium-dependent
-
flavocytochrome
- zymosan
- peroxynitrite
-
phagosomes
-
tempol
- fmlp
-
ros-dependent
-
microbicidal
- nadph-oxidase
-
nitrotyrosine
- lucigenin
- medicine
-
fmlp-induced
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Synonyms
nadph oxidase, nadph quinone oxidoreductase 1, nadph quinone oxidoreductase, nadph-quinone oxidoreductase, ppazor, xac2229, pa1225, nadph dehydrogenase (quinone), nadph:(quinone-acceptor) oxidoreductase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
azoreductase
dehydrogenase, reduced nicotinamide adenine dinucleotide phosphate (quinone)
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EC 1.6.99.6
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formerly
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MdaB
NADPH oxidase
NADPH quinone reductase
NADPH:quinone oxidoreductase 1
NQO1
PpAzoR
XAC2229
additional information
bifunctional 3alpha-hydroxysteroid dehydrogenase and NADPH reductase (quinone)
NADPH oxidase
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-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
NADPH + H+ + a quinone = NADP+ + a quinol
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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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SYSTEMATIC NAME
IUBMB Comments
NADPH:(quinone-acceptor) oxidoreductase
A flavoprotein [1, 2]. The enzyme from Escherichia coli is specific for NADPH and is most active with quinone derivatives and ferricyanide as electron acceptors [3].
Menaquinone can act as acceptor. The enzyme from hog liver is inhibited by dicoumarol and folic acid derivatives but not by 2,4-dinitrophenol [1].
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CAS REGISTRY NUMBER
COMMENTARY
37256-37-4
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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
(R,S)-camphorquinone + NADPH + H+
(R,S)-camphorquinone + NADP+
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-
-
?
2,3-dimethoxy-5-methyl-1,4-benzoquinone + NADPH + H+
2,3-dimethoxy-5-methyl-1,4-benzoquinol + NADP+
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-
-
-
?
2,6-dimethoxy-1,4-benzoquinone + NADPH + H+
2,6-dimethoxy-1,4-benzoquinol + NADP+
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-
-
?
2-methyl-5-hydroxy-1,4-naphthoquinone + NADPH + H+
2-methyl-5-hydroxy-1,4-naphthoquinol + NADP+
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-
-
-
?
5-hydroxy-2-methyl-1,4-naphthoquinone + NADPH + H+
5-hydroxy-2-methyl-1,4-naphthoquinol + NADP+
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-
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?
benzoquinone + NADPH
benzohydroquinone + NADP+
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specific for NADPH
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-
?
dichlorophenolindophenol + NADPH + H+
? + NADP+
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about 15% of the activity with menadione
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-
?
menadione + NADPH + H+
? + NADP+
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two-electron transfer mechanism from NADPH to quinone
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-
?
NADH + Fe(CN)63-
NAD+ + Fe(CN)63-
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with NADH the actuvity is less than 10% of the activity with NADPH
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-
?
NADH + H+ + 1,4-naphthoquinone
NAD+ + 1,4-naphthoquinol
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with NADH the activity is about 15% of the activity with NADPH
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?
NADH + H+ + coenzyme Q0
NAD+ + reduced coenzyme Q0
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with NADH the activity is less than 10% of the activity with NADPH
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-
?
NADH + H+ + coenzyme Q1
NAD+ + reduced coenzyme Q1
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with NADH the activity is less than 10% of the activity with NADPH
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-
?
NADH + H+ + dichlorophenolindophenol
NAD+ + reduced dichlorophenolindophenol
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with NADH the actuvity is about 15% of the activity with NADPH
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-
?
NADH + menadione
NAD+ + ?
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with NADH the activity is less than 10% of the activity with NADPH
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-
?
NADPH + H+ + 1,4-benzoquinone
NADP+ + 1,4-benzohydroquinol
no activity with NADH
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-
?
NADPH + H+ + 2,3-dichloro-5,6-dicyano-1,4-benzoquinone
NADP+ + 2,3-dichloro-5,6-dicyano-1,4-benzoquinol
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-
-
?
NADPH + H+ + 2,5-dimethyl-4-benzoquinone
NADP+ + 2,5-dimethyl-4-benzoquinonl
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-
-
-
?
NADPH + H+ + 2-hydroxy-1,4-naphthoquinone
NADP+ + 2-hydroxy-1,4-naphthoquinol
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-
-
-
?
NADPH + H+ + dichlorophenolindophenol
NADP+ + reduced dichlorophenolindophenol
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-
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-
?
NADPH + H+ + methyl-p-benzoquinone
NADP+ + methyl-p-benzohydroquinone
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-
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?
NADPH + H+ + oxidized 2,6-dichlorophenolindophenol
NADP+ + reduced 2,6-dichlorophenolindophenol
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-
?
NADPH + H+ + phenyl-1,4-benzoquinone
NADP+ + phenyl-1,4-benzoquinol
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?
NADPH + H+ + quinone
NADP+ + ?
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TNF alpha and LPS induce Nqo1 mRNA expression
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-
?
oxidized 2,6-dichlorophenolindophenol + NADPH + H+
reduced 2,6-dichlorophenolindophenol + NAD(P)+
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very low activity with NADH
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?
oxidized dichlorophenolindophenol + NADPH + H+
reduced dicholorophenolindophenol + NADP+
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?
ubiquinone-0 + NADPH + H+
ubiquinol-0 + NADP+
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two-electron transfer mechanism from NADPH to quinone
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?
ubiquinone-1 + NADPH + H+
ubiquinol-1 + NADP+
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two-electron transfer mechanism from NADPH to quinone
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?
1,4-benzoquinone + NADPH + H+
1,4-benzoquinol + NADP+
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about 81% of the activity with menadione
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?
1,4-benzoquinone + NADPH + H+
1,4-benzoquinol + NADP+
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1,4-benzoquinone is oxidized almost stoichiometric amount of NADPH, suggesting that it is reduced to its hydroquinone with a two-electron reduction mechanism
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?
1,4-naphthoquinone + NADPH + H+
1,4-naphthoquinol + NADP+
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about 85% of the activity with menadione
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?
1,4-naphthoquinone + NADPH + H+
1,4-naphthoquinol + NADP+
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two-electron transfer mechanism from NADPH to quinone
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?
1,4-naphthoquinone + NADPH + H+
1,4-naphthoquinol + NADP+
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1,4-naphthoquinone participates in the redox cycling in their reduction by this enzyme as evidenced by excess NADPH oxidation over quinone reduction. CBR4 may reduce 1,4-naphthoquinone in the two-electron reduction mechanism, but produces reactive superoxide and semiquinones through their redox cycling
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?
1,4-naphthoquinone + NADPH + H+
1,4-naphthoquinol + NADP+
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specific for NADPH
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?
2 ferricyanide + NADPH
2 ferrocyanide + NADP+ + H+
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about 90% of the activity with menadione
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?
2-methyl-1,4-naphthoquinone + NADPH + H+
2-methyl-1,4-naphthoquinol + NADP+
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?
2-methyl-1,4-naphthoquinone + NADPH + H+
2-methyl-1,4-naphthoquinol + NADP+
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i.e. menadione, specific for NADPH
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?
5-hydroxy-1,4-naphthoquinone + NADPH + H+
5-hydroxy-1,4-naphthoquinol + NADP+
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5-hydroxy-1,4-naphthoquinone participates in the redox cycling in their reduction by this enzyme as evidenced by excess NADPH oxidation over quinone reduction
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?
5-hydroxy-1,4-naphthoquinone + NADPH + H+
5-hydroxy-1,4-naphthoquinol + NADP+
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?
9,10-phenanthrenequinone + NADPH + H+
9,10-phenanthrenequinol + NADP+
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9,10-phenanthrenequinone participates in the redox cycling in their reduction by this enzyme as evidenced by excess NADPH oxidation over quinone reduction. CBR4 may reduce 9,10-phenanthrenequinone in the two-electron reduction mechanism, but produces reactive superoxide and semiquinones through their redox cycling
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?
9,10-phenanthrenequinone + NADPH + H+
9,10-phenanthrenequinol + NADP+
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?
9,10-phenanthrenequinone + NADPH + H+
9,10-phenanthrenequinol + NADP+
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?
menadione + NADPH + H+
menadiol + NADP+
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reduction follows a two-electron-pathway
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?
methyl p-benzoquinone + NADPH + H+
methyl p-benzoquinol + NADP+
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?
methyl p-benzoquinone + NADPH + H+
methyl p-benzoquinol + NADP+
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?
NADPH + acceptor
NADP+ + reduced acceptor
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acceptor: ferric chloride
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?
NADPH + acceptor
NADP+ + reduced acceptor
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aceptor: 1,10-phenanthroline
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?
NADPH + acceptor
NADP+ + reduced acceptor
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2,3',6-trichlorophenolindophenol is reduced to leuco-2,3',6-trichlorophenolindophenol
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?
NADPH + H+ + 1,2-naphthoquinone-4-sulfonate
NADP+ + ?
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i.e. Lawsone
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?
NADPH + H+ + 1,2-naphthoquinone-4-sulfonate
NADP+ + ?
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i.e. Lawsone
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?
NADPH + H+ + a quinone
NADP+ + a quinol
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the catalytic cycle of ArsH consists of the acceptance of two electrons from NADPH to reduce the flavin cofactor (reductive half-reaction) and the transfer of these electrons to an acceptor (oxidative half-reaction)
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?
phenyl 1,4-benzoquinone + NADPH + H+
phenyl 1,4-benzoquinol + NADP+
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-
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?
phenyl 1,4-benzoquinone + NADPH + H+
phenyl 1,4-benzoquinol + NADP+
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?
additional information
?
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the enzyme plays an important role in managing oxidative stress and contributes to successful colonization of the host
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?
additional information
?
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the enzyme exhibits NADPH-dependent reductase activity for o- and p-quinones, but not for other aldehydes and ketones. In vitro quinone reduction by CBR4 generates superoxide through the redox cycling, and suggest that the enzyme may be involved in the induction of apoptosis by cytotoxic 9,10-phenanthrenequinone
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?
additional information
?
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PA1225 does not react with methyl red and does not possess azoreductase activity and displays a negligible NADPH:O2 oxidase activity
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additional information
?
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PA1225 does not react with methyl red and does not possess azoreductase activity and displays a negligible NADPH:O2 oxidase activity
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additional information
?
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the bifunctional enzyme also shows activity with azo dyes and NAD(P)H as cofactor, cf. EC 1.7.1.6
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?
additional information
?
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the bifunctional enzyme also shows activity with azo dyes and NAD(P)H as cofactor, cf. EC 1.7.1.6
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?
additional information
?
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enzyme displays bifunctional 3alpha-hydroxysteroid dehydrogenase and NADPH reductase (quinone) activities. Quinone reduction occurs via a mechanism that differs from 3-ketosteroid reduction. In this mechanism, the electron donor NADPH and acceptor o-quinone are bound in close proximity, which permits hydride transfer without formal protonation of the acceptor carbonyl by Tyr 55
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?
additional information
?
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trace activity with substrates acrolein, cinnamaldehyde, 3-buten-2-one, 3-penten-2-one, 3-nonen-2-one
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-
?
additional information
?
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NADH, deazariboflavin, and methylviologen can also act as electron donors
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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
NADPH + H+ + a quinone
NADP+ + a quinol
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the catalytic cycle of ArsH consists of the acceptance of two electrons from NADPH to reduce the flavin cofactor (reductive half-reaction) and the transfer of these electrons to an acceptor (oxidative half-reaction)
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?
additional information
?
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the enzyme plays an important role in managing oxidative stress and contributes to successful colonization of the host
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?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
cytochrome b558
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gp91phox and p22phox are integral membrane proteins that form a heterodimeric flavocytochrome b558, the catalytic core of the enzyme
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FAD
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enzyme displays flavin absorption spectrum with peaks at 376 and 456 nm and a shoulder at around 484 nm. Protein caontains FAD
FAD
enzyme utilizes FAD to transfer a hydride ion from NADPH to quinones
flavin
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flavoprotein, adsorption spectrum with a major peak at 456 nm
NADPH
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NADH could also be used as an electron donor to MdaB but with much lower efficiency, about 3% of those with NADPH
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(N-methyl-4'-pyridyl) porphyrin
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iron tetrakis, FeTMPyP, no inhibitory activity
1,4-Naphthoquinone
substrate inhibition at concentrations above 0.025 mM
Cibacron blue F3GA
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the 1,4-naphthoquinone activity of CBR4 is potently inhibited, competitive with respect to NADPH
coenzyme Q0
substrate inhibition at concentrations above 0.025 mM
diphenylene iodonium
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inhibition of the NADPH oxidase complex activity reduces the increase of superoxide production induced by palmitic acid
Procion red HE3B
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the 1,4-naphthoquinone activity of CBR4 is potently inhibited, competitive with respect to NADPH
tetramethyl-1,4-benzoquinone
substrate inhibition at concentrations above 0.025 mM
4-(2-aminoethyl)benzenesulfonylfluoride
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0.206 mM, 50% inhibition, noncompetitive vs. NADPH, competitive vs. p47-phox in the concentration range of 0.5-2.0 mM