Information on EC 1.6.99.1 - NADPH dehydrogenase

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The expected taxonomic range for this enzyme is: Bacteria, Eukaryota

EC NUMBER
COMMENTARY hide
1.6.99.1
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RECOMMENDED NAME
GeneOntology No.
NADPH dehydrogenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
NADPH + H+ + acceptor = NADP+ + reduced acceptor
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
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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-
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SYSTEMATIC NAME
IUBMB Comments
NADPH:acceptor oxidoreductase
A flavoprotein (FMN in yeast, FAD in plants).
CAS REGISTRY NUMBER
COMMENTARY hide
9001-68-7
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
diaphorase activity of neutrophil NADPH oxidase
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-
Manually annotated by BRENDA team
Candida macedoniensis
expression in Escherichia coli
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-
Manually annotated by BRENDA team
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-
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Manually annotated by BRENDA team
diaphorase activity of nitric oxide synthase
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Manually annotated by BRENDA team
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-
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Manually annotated by BRENDA team
diaphorase activity of nitric oxide synthase
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-
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
Wistar
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-
Manually annotated by BRENDA team
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-
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Manually annotated by BRENDA team
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-
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Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
the enzyme is clinically relevant due to its role in the action mechanism of some trypanocidal drugs used in the treatment of Chagas' disease by producing reactive oxygen species
additional information
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
ketoisophorone + NADPH + H+
(6R)-levodione + NADP+
show the reaction diagram
Candida macedoniensis
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i.e. 2,6,6-trimethyl-2-cyclohexen-1,4-dione
i.e.2,6,6-trimethylcycolhexane-1,4-dione
-
?
NADH + acceptor
NADH + reduced acceptor
show the reaction diagram
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no activity with beta-NADH
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-
-
NADPH + acceptor
NADP+ + reduced acceptor
show the reaction diagram
NADPH + H+ + 2,4,6-trinitrotoluene
NADP+ + ?
show the reaction diagram
-
-
-
-
?
NADPH + H+ + 2-cyclohexen-1-one
NADP+ + ?
show the reaction diagram
-
the substrate results in a very rapid and strong reduction of SYE4
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-
?
NADPH + H+ + 4-hydroxybenzaldehyde
NADP+ + ?
show the reaction diagram
-
-
-
-
?
NADPH + H+ + acceptor
NADP+ + reduced acceptor
show the reaction diagram
NADPH + H+ + acrolein
NADP+ + propionaldehyde
show the reaction diagram
NADPH + H+ + cyclohex-2-enone
NADP+ + ?
show the reaction diagram
-
-
-
-
?
NADPH + H+ + N-ethylmaleimide
NADP+ + ?
show the reaction diagram
-
-
-
-
?
NADPH + H+ + NEM
NADP+ + ?
show the reaction diagram
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the substrate results in a very rapid and strong reduction of SYE4
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-
?
NADPH + H+ + nitroglycerin
NADP+ + ?
show the reaction diagram
NADPH + H+ + prostaglandin H2
NADP+ + prostaglandin F2alpha
show the reaction diagram
-
via FMN cofactor, stereoselective reaction mechanism
-
-
?
NADPH + H+ + trans-hex-2-enal
NADP+ + ?
show the reaction diagram
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-
-
-
?
additional information
?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
NADPH + acceptor
NADP+ + reduced acceptor
show the reaction diagram
NADPH + H+ + 2-cyclohexen-1-one
NADP+ + ?
show the reaction diagram
-
the substrate results in a very rapid and strong reduction of SYE4
-
-
?
NADPH + H+ + acceptor
NADP+ + reduced acceptor
show the reaction diagram
NADPH + H+ + acrolein
NADP+ + propionaldehyde
show the reaction diagram
NADPH + H+ + NEM
NADP+ + ?
show the reaction diagram
-
the substrate results in a very rapid and strong reduction of SYE4
-
-
?
NADPH + H+ + nitroglycerin
NADP+ + ?
show the reaction diagram
-
the substrate results in a very rapid and strong reduction of SYE4
-
-
?
NADPH + H+ + prostaglandin H2
NADP+ + prostaglandin F2alpha
show the reaction diagram
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via FMN cofactor, stereoselective reaction mechanism
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-
?
additional information
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADH
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no activity with beta-NADH
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Ca2+
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2 mM CaCl2, 48% stimulates. The effect is reversed by 1 mM EGTA or EDTA
Cu2+
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Cu2+ treatment causes an increase in NADPH-diaphorase activity
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(9R,13R)-12-oxophytodienoate
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alpha-NADPH
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diaphorase activity of neuron somata
L-N5-(1-iminoethyl)Orn
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1 mM 63% inhibition
monomethyl-L-Arg acetate
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1 mM, 14% inhibition
NG-nitro-L-Arg
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3 mM, 53% inhibition
Ngamma-monomethyl-L-Arg
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1 mM, 14% inhibition
Ngamma-nitro-L-arginine
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-
additional information
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the traditional chinese medicine Nao Yi An, a complex derived from materials of animal and plant origin, can selectively inhibit the induction and thus, potentially play a neuroprotective role
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.123 - 0.705
2,4,6-trinitrotoluene
0.0547
2-cyclohexen-1-one
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pH 7.3
0.109
acrolein
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pH 7.3
0.186 - 0.293
cyclohex-2-enone
0.001
N-ethylmaleimide
0.0011
NADPH
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0.0016
NEM
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pH 7.3
0.0073
nitroblue tetrazolium hydrochloride
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0.0264 - 0.109
nitroglycerin
1.853 - 2.602
trans-hex-2-enal
additional information
additional information
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.53 - 3.19
2,4,6-trinitrotoluene
4.75
2-cyclohexen-1-one
Shewanella oneidensis
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pH 7.3
0.41 - 11.66
acrolein
1.2 - 4.38
cyclohex-2-enone
0.75 - 8.07
N-ethylmaleimide
0.052 - 9.54
NEM
0.03 - 6.84
nitroglycerin
1.17 - 4.68
trans-hex-2-enal
additional information
additional information
Bacillus subtilis
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half-reaction kinetics of tagged and untagged enzyme
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.057
(9R,13R)-12-oxophytodienoate
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pH 7.0, 25C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7
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assay at
7.4
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assay at
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
25
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assay at
37
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assay at
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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in a subpopulation of olfactory receptor neurones and in mechano-, thermo- and hygroreceptors on the antenna and in non-neuronal cells
Manually annotated by BRENDA team
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retina
Manually annotated by BRENDA team
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of piglet, crypt cells, glandular epithelium in the deeper submucosa has a very strong activity, villous epithelial cells show the most intense activity in the mucosa
Manually annotated by BRENDA team
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myofiber and sarcolemma of sceletal muscle
Manually annotated by BRENDA team
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parallel to the circular and to the longitudinal muscle
Manually annotated by BRENDA team
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localized in discrete populations of neuronal somata and in olfactory glomeruli. NADPH-diaphorase activity is due to nitric oxide synthase, the glomerular NADPH-diaphorase activity is not due to nitric oxide synthase
Manually annotated by BRENDA team
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from embryo
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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in neonatal animals, small, moderately stained NADPH-d-positive cells are identified in the vertical arm and in the elbowv of the rostral migratory stream. In adult and aging rats a few labeled cells could be also detected in the RMS horizontal arm. The number of NADPH-d-positive cells increases with advancing age
Manually annotated by BRENDA team
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cyclic changes dependent on the estrous cycle. Changes observed mostly in the luminal epithelium and some endometrial glands. Localization and correlation between NADPH-diaphorase and nitric oxide synthase isoforms
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
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Manually annotated by BRENDA team
PDB
SCOP
CATH
ORGANISM
UNIPROT
Bacillus subtilis (strain 168)
Bacillus subtilis (strain 168)
Bacillus subtilis (strain 168)
Bacillus subtilis (strain 168)
Geobacillus kaustophilus (strain HTA426)
Geobacillus kaustophilus (strain HTA426)
Scheffersomyces stipitis (strain ATCC 58785 / CBS 6054 / NBRC 10063 / NRRL Y-11545)
Scheffersomyces stipitis (strain ATCC 58785 / CBS 6054 / NBRC 10063 / NRRL Y-11545)
Shewanella oneidensis (strain MR-1)
Shewanella oneidensis (strain MR-1)
Shewanella oneidensis (strain MR-1)
Shewanella oneidensis (strain MR-1)
Thermoanaerobacter pseudethanolicus (strain ATCC 33223 / 39E)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
37400
-
4 * 37400, SDS-PAGE, native protein, 4 * 62900, SDS-PAGE, GST-tagged protein, in 3:1 dimer/tetramer equilibrium
38300
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2 * 38300, SDs-PAGE, His-tagged protein, 2 * 62900, SDS-PAGE, GST-tagged protein, in 3:1 dimer/tetramer equilibrium
42400
Candida macedoniensis
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x * 45890, deduced from gene sequence, x * 42400, SDS-PAGE
44889
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x * 44889, calculation from nucleotide sequence
45890
Candida macedoniensis
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x * 45890, deduced from gene sequence, x * 42400, SDS-PAGE
62900
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2 * 38300, SDs-PAGE, His-tagged protein, 2 * 62900, SDS-PAGE, GST-tagged protein, in 3:1 dimer/tetramer equilibrium; 4 * 37400, SDS-PAGE, native protein, 4 * 62900, SDS-PAGE, GST-tagged protein, in 3:1 dimer/tetramer equilibrium
76500
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gel filtration, His-tagged protein
114400
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gel filtration, GST-tagged protein
147000
235000
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gel filtration
247500
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gel filtration, GST-tagged protein
374000
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4 * 374000, SDS-PAGE, recombinant protein
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
TcOYE behaves as a globular monomer in solution
tetramer
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
purified enzyme, hanging drop vapor diffusion method, mixing of 0.002 ml of protein solution containing 14 mg/mL in 25 mM Tris-HCl, pH 8.0, containing 100 mM NaCl, and 1 mM 2-mercaptoethanol, with 0002 ml of 28% w/v PEG 1500, and 0.3 M ammonium fluoride, equilibration against 0.5 ml of reservoir solution, 19C, 10 days, crystalline forms I and II, X-ray diffraction structure determination and analysis at 1.27 A and 2.0 A resolution, respectively
purified recombinant enzyme in a ternary complex with inhibitor 12-oxophytodienoate and FMN, X-ray diffraction structure determination and analysis at 2.05 A resolution
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
N-terminal glutathione-S-transferase fusion and a C-terminal His-tagged form expressed in Escherichia coli
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recombinant glutathione-S-transferase-tagged enzyme
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recombinant N-terminally His6-tagged enzyme from Escherichia coli strain BL21(DE3) by affinity chromatography
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
expression of N-terminally His6-tagged enzyme in Escherichia coli strain BL21(DE3)
overexpression of the enzyme in Escherichia coli
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
the enzyme is induced under Cu2+-stress
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Y196F
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slowing by nearly 6 orders of magnitude of its oxidative half-reaction with 2-cyclohexenone
additional information
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enzyme deletion strain, shows overly elaborate actin cytoskeleton probably reflecting stabilization of actin filaments, and is sensitive to oxidative stress. Phenotype is suppressed by mutation of either conserved cysteine of the pair C285-C374 of actin
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
analysis
synthesis
Candida macedoniensis
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production of (6R)-levodione in Escherichia coli expressing the enzyme plus glucose dehydrogenase with a molar yield of 95%
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