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1.14.13.39: nitric-oxide synthase (NADPH)

This is an abbreviated version!
For detailed information about nitric-oxide synthase (NADPH), go to the full flat file.

Word Map on EC 1.14.13.39

Reaction

2 L-arginine + 2 NADPH + 2 H+ + 2 O2 = 2 Nomega-hydroxy-L-arginine + 2 NADP+ + 2 H2O

Synonyms

bacterial nitric oxide synthase, bacterial nitric-oxide synthase, bNOS, bsNOS, cb-NOS, cytokine inducible NOS, DNOS, e-NOS, EC-NOS, endothelial nitric oxide synthase, endothelial nitric-oxide synthase, endothelial NO synthase, endothelial NOS, endothelium-derived relaxation factor-forming enzyme, endothelium-derived relaxing factor synthase, eNOS, i-NOS, inducible nitric oxide synthase, inducible nitric-oxide synthase, inducible NO synthase, inducible NOS, iNOS, mitochondrial NO synthase, mitochondrial-specific nitric oxide synthase, mtNOS, n-NOS, NADPH diaphorase, NADPH-d, NADPH-diaphorase, NADPHd, neuronal nitric oxide synthase, neuronal nitric-oxide synthase, neuronal NO synthase, neuronal NOS, nicotinamide adenine dinucleotide phosphate-diaphorase, nitric oxid synthase, nitric oxide synthase, nitric oxide synthase-like protein, nitric oxide synthetase, nitric-oxide synthase, nNOS, nNOSalpha, NO synthase, NO synthase type I, NO synthase type II, NO synthase type III, NO-synthase, NOS, NOS I, NOS-2, NOS1, NOS2, NOS3, synthetase, nitric oxide

ECTree

     1 Oxidoreductases
         1.14 Acting on paired donors, with incorporation or reduction of molecular oxygen
             1.14.13 With NADH or NADPH as one donor, and incorporation of one atom of oxygen into the other donor
                1.14.13.39 nitric-oxide synthase (NADPH)

Inhibitors

Inhibitors on EC 1.14.13.39 - nitric-oxide synthase (NADPH)

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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(4S)-N-(4-amino-5-[aminoethyl]aminopentyl)-N''-nitroguanidine
-
1,5,6,7-tetrahydro-2H-azepin-2-imines
-
-
1-phenylimidazole
-
reversible inhibition of endothelial enzyme, competitive versus L-arginine and tetrahydrobiopterin, no inhibition of cytochrome c reduction
2',3'-dialdehyde of NADPH
-
at concentrations of 40times the apparent Km-value or after prolonged incubation, independent of Ca2+/calmodulin, L-arginine or tetrahydrobiopterin, NADPH prevents inhibition, the NADPH-diaphorase activity of the enzyme is less sensitive than the nitric oxide synthase activity
2-aminopyridine derivatives
highly selective inhibitors
-
3,4-dihydro-1-isoquinolinamines
-
-
3-bromo-7-nitroindazole
nNOS-specific inhibitor, complete inhibition at 0.01 mM
3-[cis-4'-[(6''-aminopyridin-2''-yl)methyl]pyrrolidin-3'-ylamino]propan-1-ol
-
4-(3-amino-propoxy)-1-benzopyran-2-one hydrochloric acid salt
4-(3-amino-propoxy)-6-chloro-1H-quinolin-2-one trifluoroacetic acid salt
IC50: 410 nM, pharmacokinetic profile
4-(3-dimethylamino-propoxy)-1-benzopyran-2-one hydrochloric acid salt
4-(3-dimethylamino-propoxy)-1H-quinolin-2-one
4-oxononenal
ONE, a highly bioreactive agent, able to inhibit eNOS activity and NO production. It can posttranslationally modify the enzyme in the placenta
-
5,6,7,8-tetrahydrobiopterin
-
quenches the uncoupled reactions and results in much less reactive oxygen species formation, whereas the presence of redox-incompetent 7,8-dihydrobiopterin demonstrates little quenching effect
6(R,S)-methyl-5-deazatetrahydropterin
-
-
6-([[(3R,5S)-5-[[(6-amino-4-methylpyridin-2-yl)methoxy]methyl]pyrrolidin-3-yl]oxy]methyl)-4-methylpyridin-2-amine
exhibits antimicrobial properties
6-chloro-4-(3-aminopropoxy)-1-benzopyran-2-one trifluoroacetic acid salt
6-chloro-4-(3-dimethylamino-propoxy)-1-benzopyran-2-one hydrochloric acid salt
6-chloro-4-(3-methylamino-propoxy)-1-benzopyran-2-one trifluoroacetic acid salt
6-n-propyl-2-thyouracil
0.1 mg 6-n-propyl-2-thyouracil decreases nNOS activity to 45% compared to control
6-[[(2S,3S)-2-amino-3-[(6-amino-4-methylpyridin-2-yl)methoxy]butoxy]methyl]-4-methylpyridin-2-amine
exhibits antimicrobial properties
7-nitroindazole
A-23187
high levels of A-23187 inhibit nNOS activity
agmatine
-
at lower concentration than the Ki value agmatine leads to time-, concentration-, NADPH- and calmodulin-dependent inhibition of the neuronal enzyme in presence of calmodulin; causes an increase in NADPH oxidase activity of the enzyme
aminoguanidine
AR-C102222
AR-C85016
AR-R17477
Calcineurin
-
-
-
Calmidazolium
carbon monoxide
carbon monoxide down-regulates iNOS activity by reducing its expression level or by inhibiting its activity by converting it to an inactive P420 form, the presence of dithiothreitol, L-Arg, or H4B partially inhibits the iNOSP450 to iNOSP420 conversion, whereas the presence of both L-Arg and 5,6,7,8-tetrahydro-L-biopterin completely prevents the transition
CO/O2
-
80%:20%, mixture
-
cyanide
Di-2-thienyliodonium
-
competitive, irreversible, complete, time and temperature dependent inhibition
dimethylarginine
-
-
diphenylene iodonium
ethylene glycol bis(beta-amino-ethylether)-N,N,N',N'-tetraacetic acid
Gly-methyl-L-arginine
-
inhibition of the isozymes in absence or presence of L-arginine
H2O2
-
alters heme group, decrease in activity
imidazole
inhibitor NS1
Iodoniumdiphenyl
-
competitive, irreversible, complete, time and temperature dependent inhibition
L-arginine
L-arginine methyl ester
-
L-Asn-methyl-L-arginine
-
inhibition of the isozymes in absence or presence of L-arginine
L-canavanine
L-N-methylarginine
NOS inhibitor, complete inhibition at 0.5 mM; NOS inhibitor, complete inhibition at 0.5 mM; NOS inhibitor, complete inhibition at 0.5 mM
L-N6-(1-iminoethyl)lysine dihydrochloride
-
5 mM, 78% inhibition
L-NG-monomethyl arginine
L-NMMA
-
L-NG-nitro-arginine-methylester
-
-
L-Nomega-nitroarginine-(4R)-amino-L-proline amide
-
L-Nomega-nitroarginine-2,4-L-diaminobutyramide
-
L-omega-monomethyl L-arginine
potent competitive eNOS inhibitor, complete inhibition at 10 mM
L-thiocitrulline
MeHg
methylmercury, impact of chronic MeHg intoxication on NADPH diaphorase (NADPH-d) activity and astrocyte mobilization in the visual cortex of the rat, overview. MeHg accumulates in the central nervous system (CNS) and preferentially accumulates in astrocytes, and it causes several neurotoxic effects, such as visual-field constriction, cerebellar ataxia and multimodal sensory disorders. MeHg-intoxicated animals display a significant decrease of NADPH-d neuropil reactivity across the visual cortex when compared to controls. The decreased neuropil reactivity to NADPH-d may also be related to MeHg-induced astrocytic dysfunction
-
methylisothiourea
-
0.01 mM, about 80% residual activity
N(G),N(G)-dimethyl-L-arginine
-
asymmetric dimethyl arginine
N(G)-nitroarginine methyl ester
-
N-(4-aminobutyl)-5-chloro-2-naphthalene sulfonamide
-
-
N-(6-Aminohexyl)-1-naphthalene sulfonamide
-
-
N-(6-aminohexyl)-5-chloro-1-naphthalene sulfonamide
-
calmodulin antagonist above 0.01 mM; i.e. W-7
N-iminoethyl-L-lysine
no isozyme specificity
N-iminoethyl-L-ornithine
no isozyme specificity
N-monomethyl-L-arginine
-
0.01 mM, about 55% residual activity
N-nitro-L-arginine methyl ester
N-omega-nitro-L-arginine
-
N-[(1,3-benzodioxol-5-yl)methyl]-1-[2-(1H-imidazol-1-yl)pyrimidin-4-yl]-4-(methoxycarbonyl)-piperazine-2-acetamide
inhibition of dimer formation in vivo and in vitro, efficiency is dependent on enzyme source
N1-[cis-4'-[(6''-amino-4''-methylpyridin-2''-yl)methyl]pyrrolidin-3'-yl]-N2-(4'-chlorobenzyl)ethane-1,2-diamine
-
N1-[cis-4'-[(6''-aminopyridin-2''-yl)methyl]pyrrolidin-3'-yl]ethane-1,2-diamine
-
N1-[trans-4'-[(6''-amino-4''-methylpyridin-2''-yl)methyl]pyrrolidin-3'-yl]-N2-(3'-chlorobenzyl)ethane-1,2-diamine
-
nanoshutter NS1
mixture of (2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-([2-(ethyl(4-[(E)-2-(4-nitrophenyl)ethenyl]phenyl)amino)ethyl]carbamoyl)-4-hydroxyoxolan-3-yl dihydrogen phosphate and (2R,3R,4R,5S)-2-(6-amino-9H-purin-9-yl)-5-([2-(ethyl(4-[(E)-2-(4-nitrophenyl)ethenyl]phenyl)amino)ethyl]carbamoyl)-4-hydroxyoxolan-3-yl dihydrogen phosphate. The NOS inhibitor targets the reductase domain of the enzyme
-
NG-methyl arginine
-
specific inhibition
NG-methyl-L-arginine
no isozyme specificity
Ng-monomethy-L-arginine
-
-
NG-Nitro-L-arginine
Ngamma,Ngamma-dimethyl-L-arginine
Ngamma-amino-L-arginine
-
-
Ngamma-hydroxy-Ngamma-methyl-L-arginine
-
preincubation at 37°C leads to irreversible inactivation, substrates protect
Ngamma-iminoethyl-L-ornithine
-
competitive inhibitor
Ngamma-monomethyl-L-arginine
Ngamma-nitro-L-arginine
Ngamma-nitro-L-arginine methyl ester
nitroblue tetrazolium
NO
-
feedback inhibition
Nomega-nitro-L-arginine methyl ester
Nomega-nitro-L-arginine methylester
-
NXN-188
-
a dual-action oral therapeutic being developed for the treatment of acute migraine. The pharmacological mechanism of action of NXN-188 involves inhibition of both the neuronal nitric oxide synthase enzyme isoform and affinity for serotonin receptors. Clinical studies and pharmacokinetics, detailed overview
PIN
-
human protein enzyme inhibitor, recombinantly expressed in Escherichia coli, the recombinant CREB-binding protein-bound inhibitor protein is purified by calmodulin affinity and inhibits the enzyme to a high extent at 0.001 mM
-
S-ethylisothiourea
tetrahydrobiopterin
-
inhibits peroxynitrite activation
thiocoumarin
Trifluoperazine
W7 hydrochloride
-
5 mM, 50% inhibition
additional information
-