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Information on EC 1.6.99.1 - NADPH dehydrogenase
for references in articles please use BRENDA:EC1.6.99.1
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EC Tree 1 Oxidoreductases
1.6 Acting on NADH or NADPH
1.6.99 With unknown physiological acceptors
1.6.99.1 NADPH dehydrogenase
IUBMB Comments
A flavoprotein (FMN in yeast, FAD in plants).
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota, Archaea
- 1.6.99.1
- endothelial
-
l-name
- artery
- l-arginine
- nerve
- ng-nitro-l-arginine
-
vasodilation
- vessel
- nnos
- lipopolysaccharide
- hypertension
- cardiovascular
- acetylcholine
- agonist
- cerebral
- nitrite
- cyclase
- nitroprusside
-
endothelium-dependent
- coronary
-
contractile
- aorta
- cgmp
-
tone
-
histochemistry
- ischemia
-
cyclooxygenase
- dimethylarginine
- ng-monomethyl-l-arginine
-
guanylate
- nomega-nitro-l-arginine
- indomethacin
- nmda
- ganglion
-
innervation
-
vasoactive
-
guanylyl
- peroxynitrite
-
vasoconstriction
- aminoguanidine
- phenylephrine
-
vasorelaxation
-
endothelium-derived
- myenteric
-
cholinergic
- n-methyl-d-aspartate
- tetrahydrobiopterin
-
erectile
- bh4
-
precontracted
- analysis
- synthesis
showSynonyms
nitric oxide synthase, nadph-diaphorase, nadph-d, nadph diaphorase, nicotinamide adenine dinucleotide phosphate diaphorase, nadph dehydrogenase, 2-cyclohexen-1-one, estrogen-binding protein, nadph-dehydrogenase, nadp-d, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
2-cyclohexen-1-one
dehydrogenase, reduced nicotinamide adenine dinucleotide phosphate
-
-
-
-
diaphorase
-
-
-
-
dihydronicotinamide adenine dinucleotide phosphate dehydrogenase
-
-
-
-
EBP
-
-
-
-
Estrogen-binding protein
-
-
-
-
NADPH diaphorase
NADPH-d
NADPH-dehydrogenase
-
-
-
-
NADPH-dependent cyclohexenone reductase
NADPH-dependent diaphorase
-
-
-
-
NADPH-diaphorase
NADPH-methemoglobin reductase
-
-
-
-
NADPH2-dehydrogenase
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-
-
-
NCR
nitric oxide synthase
old yellow enzyme
Old yellow enzyme homolog
-
-
-
-
OYE
reduced nicotinamide adenine dinucleotide phosphate dehydrogenase
-
-
-
-
TPNH dehydrogenase
-
-
-
-
TPNH-diaphorase
-
-
-
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triphosphopyridine diaphorase
-
-
-
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triphosphopyridine nucleotide diaphorase
-
-
-
-
YqjM
NADPH diaphorase
-
-
-
-
NADPH-diaphorase
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-
-
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old yellow enzyme
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-
-
-
OYE
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
NADPH + H+ + acceptor = NADP+ + reduced acceptor
reaction mechanism involving a conserved triad of Glu193-His284-Arg249, overview
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NADPH + H+ + acceptor = NADP+ + reduced acceptor
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-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
-
-
-
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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).
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CAS REGISTRY NUMBER
COMMENTARY
9001-68-7
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(E)-ethyl 2-methyl-4-oxopent-2-enoate + NADP+
ethyl (2R)-2-methyl-4-oxopentanoate + NADPH + H+
-
Substrates: -
Products: -
Products: -
?
ketoisophorone + NADPH + H+
(6R)-levodione + NADP+
Candida macedoniensis
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Substrates: i.e. 2,6,6-trimethyl-2-cyclohexen-1,4-dione
Products: i.e.2,6,6-trimethylcycolhexane-1,4-dione
Products: i.e.2,6,6-trimethylcycolhexane-1,4-dione
?
methyl 2-phenylacrylate + NADP+
methyl (2R)-2-methyl-3-phenylpropanoate + NADPH + H+
-
Substrates: -
Products: -
Products: -
?
NADH + H+ + acceptor
NAD+ + reduced acceptor
-
Substrates: no activity with beta-NADH
Products: -
Products: -
?
NADPH + H+ + 2,4,6-trinitrotoluene
NADP+ + ?
-
Substrates: -
Products: -
Products: -
?
NADPH + H+ + 2-cyclohexen-1-one
NADP+ + ?
-
Substrates: the substrate results in a very rapid and strong reduction of SYE4
Products: -
Products: -
?
NADPH + H+ + cyclohex-2-enone
NADP+ + ?
-
Substrates: -
Products: -
Products: -
?
NADPH + H+ + N-ethylmaleimide
NADP+ + ?
-
Substrates: -
Products: -
Products: -
?
NADPH + H+ + NEM
NADP+ + ?
-
Substrates: the substrate results in a very rapid and strong reduction of SYE4
Products: -
Products: -
?
NADPH + H+ + oxidized nitroblue tetrazolium hydrochloride
NADP+ + reduced nitroblue tetrazolium hydrochloride
-
Substrates: -
Products: -
Products: -
r
NADPH + H+ + prostaglandin H2
NADP+ + prostaglandin F2alpha
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Substrates: via FMN cofactor, stereoselective reaction mechanism
Products: -
Products: -
?
NADPH + H+ + trans-hex-2-enal
NADP+ + ?
-
Substrates: -
Products: -
Products: -
?
(1-nitroprop-1-en-2-yl)benzene + NADP+
?
-
Substrates: -
Products: -
Products: -
?
(1-nitroprop-1-en-2-yl)benzene + NADP+
[(2S)-1-nitropropan-2-yl]benzene + NADPH + H+
-
Substrates: -
Products: -
Products: -
?
(1-nitroprop-1-en-2-yl)benzene + NADP+
[(2S)-1-nitropropan-2-yl]benzene + NADPH + H+
-
Substrates: -
Products: -
Products: -
?
(E)-(2-nitroprop-1-en-1-yl)benzene + NADP+
?
-
Substrates: -
Products: -
Products: -
?
(E)-(2-nitroprop-1-en-1-yl)benzene + NADP+
[(3S)-3-nitrobutyl]benzene + NADPH + H+
-
Substrates: -
Products: -
Products: -
?
(E)-(2-nitroprop-1-en-1-yl)benzene + NADP+
[(3S)-3-nitrobutyl]benzene + NADPH + H+
-
Substrates: -
Products: -
Products: -
?
(E)-ethyl 2-methyl-4-oxopent-2-enoate + NADP+
?
-
Substrates: -
Products: -
Products: -
?
(E)-ethyl 2-methyl-4-oxopent-2-enoate + NADP+
?
-
Substrates: -
Products: -
Products: -
?
2-cyclohexen-1-one + NADPH + H+
cyclohexanone + NADP+
-
Substrates: -
Products: -
Products: -
?
2-cyclohexen-1-one + NADPH + H+
cyclohexanone + NADP+
-
Substrates: -
Products: -
Products: -
?
NADPH + acceptor
NADP+ + reduced acceptor
-
Substrates: acceptor: nitroblue tetrazolium hydrochloride
Products: -
Products: -
?
NADPH + acceptor
NADP+ + reduced acceptor
-
Substrates: the enzyme is transiently activated by pheromone
Products: -
Products: -
?
NADPH + acceptor
NADP+ + reduced acceptor
-
Substrates: -
Products: -
Products: -
?
NADPH + acceptor
NADP+ + reduced acceptor
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Substrates: diaphorase activity of neuron somata shows no activity with alpha-NADPH
Products: -
Products: -
?
NADPH + acceptor
NADP+ + reduced acceptor
-
Substrates: acceptor: nitroblue tetrazolium hydrochloride
Products: -
Products: -
?
NADPH + acceptor
NADP+ + reduced acceptor
-
Substrates: intracerebral hemorrhage in the internal capsule may induce NADPH-diaphorase activity
Products: -
Products: -
?
NADPH + acceptor
NADP+ + reduced acceptor
-
Substrates: -
Products: -
Products: -
?
NADPH + acceptor
NADP+ + reduced acceptor
-
Substrates: acceptor: 2-cyclohexenone
Products: -
Products: -
?
NADPH + acceptor
NADP+ + reduced acceptor
-
Substrates: both alpha-NADPH and beta-NADPH are capable of reducing the enzyme. alpha-NADPH is more effective
Products: -
Products: -
?
NADPH + acceptor
NADP+ + reduced acceptor
-
Substrates: physiological role as electron transfer component
Products: -
Products: -
?
NADPH + acceptor
NADP+ + reduced acceptor
-
Substrates: acceptor: nitroblue tetrazolium hydrochloride
Products: -
Products: -
?
NADPH + acceptor
NADP+ + reduced acceptor
-
Substrates: nitroblue tetrazolium is reduced to formazan
Products: -
Products: -
?
NADPH + H+ + acceptor
NADP+ + reduced acceptor
-
Substrates: the one-electron transfer from OYE proceeds more smoothly than the two-electron transfer from OYE. The physiological electron acceptors may be cytochrome b5 or a b5-like protein
Products: -
Products: -
?
NADPH + H+ + acceptor
NADP+ + reduced acceptor
-
Substrates: -
Products: -
Products: -
?
NADPH + H+ + acrolein
NADP+ + propionaldehyde
-
Substrates: OYE2 protects against acrolin toxicity, the product propionaldehyde is not toxic. OYE2 is required for basal level of tolerance
Products: -
Products: -
?
NADPH + H+ + acrolein
NADP+ + propionaldehyde
-
Substrates: OYE3 protects against acrolin toxicity, the product propionaldehyde is not toxic. OYE3 expression is particularly induced following acrolein stress
Products: -
Products: -
?
NADPH + H+ + acrolein
NADP+ + propionaldehyde
-
Substrates: the substrate results in a very rapid and strong reduction of SYE4
Products: -
Products: -
?
NADPH + H+ + nitroglycerin
NADP+ + ?
-
Substrates: the substrate results in a very rapid and strong reduction of SYE4
Products: -
Products: -
?
additional information
?
-
-
Substrates: involved in detoxification and oxidative stress response
Products: -
Products: -
?
additional information
?
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Substrates: OYE3 interferes with Bax- and H2O2-induced lipid peroxidation and cell death in Saccharomyces cerevisiae
Products: -
Products: -
?
additional information
?
-
Substrates: the photoinduced electron transfer is compared in the structurally homologous enzymes 12-oxophytodienoate reductase 1 (OPR1) and Old Yellow Enzyme 1 (OYE1). The inside of a protein active site is a complex/heterogeneous dielectric network where genetically programmed heterogeneity near the site of biological electron transfer can significantly affect the presence and lifetime of various intermediate states
Products: -
Products: -
-
additional information
?
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Substrates: analysis of binding mode of beta-lapachone, a trypanocidal agent, and other naphthoquinones by molecular docking and dynamics: their binding to TcOYE is stabilized mainly by interactions with the isoalloxazine ring from FMN and residues from the active-site pocket
Products: -
Products: -
?
additional information
?
-
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Substrates: old yellow enzyme is an NADPH oxidoreductase capable of reducing a variety of compounds, it catalyzes one- or two-electron reduction
Products: -
Products: -
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
NADPH + H+ + 2-cyclohexen-1-one
NADP+ + ?
-
Substrates: the substrate results in a very rapid and strong reduction of SYE4
Products: -
Products: -
?
NADPH + H+ + NEM
NADP+ + ?
-
Substrates: the substrate results in a very rapid and strong reduction of SYE4
Products: -
Products: -
?
NADPH + H+ + nitroglycerin
NADP+ + ?
-
Substrates: the substrate results in a very rapid and strong reduction of SYE4
Products: -
Products: -
?
NADPH + H+ + prostaglandin H2
NADP+ + prostaglandin F2alpha
-
Substrates: via FMN cofactor, stereoselective reaction mechanism
Products: -
Products: -
?
2-cyclohexen-1-one + NADPH + H+
cyclohexanone + NADP+
-
Substrates: -
Products: -
Products: -
?
2-cyclohexen-1-one + NADPH + H+
cyclohexanone + NADP+
-
Substrates: -
Products: -
Products: -
?
NADPH + acceptor
NADP+ + reduced acceptor
-
Substrates: the enzyme is transiently activated by pheromone
Products: -
Products: -
?
NADPH + acceptor
NADP+ + reduced acceptor
-
Substrates: intracerebral hemorrhage in the internal capsule may induce NADPH-diaphorase activity
Products: -
Products: -
?
NADPH + acceptor
NADP+ + reduced acceptor
-
Substrates: physiological role as electron transfer component
Products: -
Products: -
?
NADPH + H+ + acceptor
NADP+ + reduced acceptor
-
Substrates: the one-electron transfer from OYE proceeds more smoothly than the two-electron transfer from OYE. The physiological electron acceptors may be cytochrome b5 or a b5-like protein
Products: -
Products: -
?
NADPH + H+ + acceptor
NADP+ + reduced acceptor
-
Substrates: -
Products: -
Products: -
?
NADPH + H+ + acrolein
NADP+ + propionaldehyde
-
Substrates: OYE2 protects against acrolin toxicity, the product propionaldehyde is not toxic. OYE2 is required for basal level of tolerance
Products: -
Products: -
?
NADPH + H+ + acrolein
NADP+ + propionaldehyde
-
Substrates: OYE3 protects against acrolin toxicity, the product propionaldehyde is not toxic. OYE3 expression is particularly induced following acrolein stress
Products: -
Products: -
?
NADPH + H+ + acrolein
NADP+ + propionaldehyde
-
Substrates: the substrate results in a very rapid and strong reduction of SYE4
Products: -
Products: -
?
additional information
?
-
-
Substrates: involved in detoxification and oxidative stress response
Products: -
Products: -
?
additional information
?
-
-
Substrates: OYE3 interferes with Bax- and H2O2-induced lipid peroxidation and cell death in Saccharomyces cerevisiae
Products: -
Products: -
?
additional information
?
-
Substrates: analysis of binding mode of beta-lapachone, a trypanocidal agent, and other naphthoquinones by molecular docking and dynamics: their binding to TcOYE is stabilized mainly by interactions with the isoalloxazine ring from FMN and residues from the active-site pocket
Products: -
Products: -
?
additional information
?
-
-
Substrates: old yellow enzyme is an NADPH oxidoreductase capable of reducing a variety of compounds, it catalyzes one- or two-electron reduction
Products: -
Products: -
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
FMN
-
binds to the enzyme at the carboxy-terminal end of the barrel in anextended conformation
FMN
prosthetic group, detailed binding mode, overview. TcOYE displays a canonical (alpha/bet)8-barrel fold with a FMN prosthetic group located at the large active-site cavity
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
-
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
LITERATURE
IMAGE
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
additional information
-
half-reaction kinetics of tagged and untagged enzyme
-