Information on EC 1.6.3.1 - NAD(P)H oxidase (H2O2-forming)

Word Map on EC 1.6.3.1
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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria, Archaea

EC NUMBER
COMMENTARY hide
1.6.3.1
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RECOMMENDED NAME
GeneOntology No.
NAD(P)H oxidase (H2O2-forming)
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
NAD(P)H + H+ + O2 = NAD(P)+ + H2O2
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
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redox reaction
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reduction
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SYSTEMATIC NAME
IUBMB Comments
NAD(P)H:oxygen oxidoreductase (H2O2-forming)
Requires FAD, heme and calcium. When calcium is present, this transmembrane glycoprotein generates H2O2 by transfering electrons from intracellular NAD(P)H to extracellular molecular oxygen. The electron bridge within the enzyme contains one molecule of FAD and probably two heme groups. This flavoprotein is expressed at the apical membrane of thyrocytes, and provides H2O2 for the thyroid peroxidase-catalysed biosynthesis of thyroid hormones.
CAS REGISTRY NUMBER
COMMENTARY hide
9032-22-8
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
high sequence similarities to mammalian proteins
UniProt
Manually annotated by BRENDA team
Duox, dual specificity enzyme NADPH oxidase/peroxidase
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-
Manually annotated by BRENDA team
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-
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Manually annotated by BRENDA team
isoform NADPH oxidase 5
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
rice pathogen, which undergoes an oxidative blast of its own during plant infection
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Manually annotated by BRENDA team
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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
gene nox1
UniProt
Manually annotated by BRENDA team
gene nox1
UniProt
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
metabolism
physiological function
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
NAD(P)H + H+ + O2
NAD(P)+ + H2O2
show the reaction diagram
NADH + H+ + O2
NAD+ + H2O2
show the reaction diagram
NADPH + H+ + O2
?
show the reaction diagram
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the protein shows NADH-ubiquinone-1 oxidoreductase activity (EC 1.6.5.3), NADPH oxidase (EC 1.6.3.1) and NADPH-ubiquinone-1 oxidoreductase (EC 1.6.5.2) activities
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-
?
NADPH + H+ + O2
NADP+ + H2O2
show the reaction diagram
NADPH + O2
NADP+ + O2-
show the reaction diagram
additional information
?
-
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
NAD(P)H + H+ + O2
NAD(P)+ + H2O2
show the reaction diagram
NADH + H+ + O2
NAD+ + H2O2
show the reaction diagram
NADPH + H+ + O2
NADP+ + H2O2
show the reaction diagram
NADPH + O2
NADP+ + O2-
show the reaction diagram
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
ADP
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bound to NAD(P)H-binding domain
FMN
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can replace for FAD
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Ba2+
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very low activity
Fe2+
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heme iron
Ni2+
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treatment of root with Ni2+ results in significant increase in level of membrane lipid peroxidation, content of H2O2, the production rate of superoxide radicals and the activity of the PM NADPH oxidase. Effects of Ni2+ are inhibitied by treratment with enzyme inhibitors diphenylene idonium, imidazole and pyridine
Sr2+
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can replace for Ca2+
additional information
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(-)-epicatechin
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serves as prodrug for conversion into apocynin-like NAD(P)H oxidase inhibitors
(-)-epicatechin glucuronide
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acts both as a superoxide anion scavenger,and inhibitory to NAD(P)H oxidase, with apocynin-like mode of NADPH oxidase inhibition
(-)-epigallocatechin gallate
(-)-epigallocatechin-3-O-(3-O-methyl)-gallate
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inhibition of intracellular reactive oxygen species generation
(1R)-1-[(2R,2'R,5R,5'R)-5'-[(1R)-1-hydroxyundec-3-yn-1-yl]octahydro-2,2'-bifuran-5-yl]dodec-4-yn-1-ol
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(1R)-1-[(2R,2'R,5R,5'R)-5'-[(1R)-1-hydroxyundecyl]octahydro-2,2'-bifuran-5-yl]dodecan-1-ol
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(1R,1'R)-1,1'-((2R,2'R,5R,5'R)-octahydro-2,2'-bifuran-5,5'-diyl)-bis-(6-(4-n-butylphenoxy)hex-3-yn-1-ol)
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(1R,1'R)-1,1'-((2R,2'R,5R,5'R)-octahydro-2,2'-bifuran-5,5'-diyl)-bis-(6-(4-n-butylphenoxy)hexan-1-ol)
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(2Z)-2-(5-hydroxy-4,6-dimethyl-2-oxo-1,2-dihydro-3H-indol-3-ylidene)-N,N-di(prop-2-en-1-yl)hydrazinecarbothioamide
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complete inhibition at 0.01 mM
(3Z)-3-(3,4-dihydroxybenzylidene)-5-nitro-1,3-dihydro-2H-indol-2-one
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complete inhibition at 0.01 mM
(3Z)-3-[4-hydroxy-3,5-di(propan-2-yl)benzylidene]-1,3-dihydro-2H-indol-2-one
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complete inhibition at 0.01 mM
(5'Z)-5'-[(4-heptyl-5-methyl-1H-pyrrol-2-yl)methylidene]-4'-methoxy-1H,5'H-2,2'-bipyrrole
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i.e. PG-L-1, prodigosin analogue, a red pigment isolated from marine bacterial strain. Significant inhibition of superoxide anion production by phorbol 12-myristate 13-acetate stimulated RAW 264.7 cells. (5'Z)-5'-[(4-heptyl-5-methyl-1H-pyrrol-2-yl)methylidene]-4'-methoxy-1H,5'H-2,2'-bipyrrole strongly inhibits the association of subunits p47phox and Rac in the plasma membrane
1-(2-chlorobenzyl)-4-methyl-5-[3-(2-oxopyrrolidin-1-yl)propyl]-2-phenyl-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
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1-(4-fluorobenzyl)-5-[2-(1H-indol-3-yl)ethyl]-4-methyl-2-phenyl-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
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1-acetyl-2-(2-chlorophenyl)-4-methyl-5-(pyridin-3-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
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1-acetyl-4-methyl-2-(2-methylphenyl)-5-(pyridin-3-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
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1-acetyl-4-methyl-2-phenyl-5-(pyridin-3-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
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1-[(3-methoxyphenyl)acetyl]-4-methyl-2-phenyl-5-(pyridin-3-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
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15-cis-(4-propyl-cyclohexyl)-16,17,18,19,20-pentanor-9-deoxy-9alpha,6-nitrilo-prostaglandin F1 methyl ester
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0.021 mM, 50% inhibition of the enzyme in neutrophils possible due to scavenging of O2-, inhibition of SDS-induced activation in cell free extracts, 0.22 mM, 50% inhibition
2,3,8,9-tetrahydroxy-5-(2-hydroxy-5-nitrobenzyl)phenanthridin-6(5H)-one
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complete inhibition at 0.01 mM
2,3,8,9-tetrahydroxy-5-(3-nitrobenzyl)phenanthridin-6(5H)-one
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complete inhibition at 0.01 mM
2,3,8,9-tetrahydroxy-5-(4-nitrobenzyl)phenanthridin-6(5H)-one
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93% inhibition at 0.01 mM
2,3,8,9-tetrahydroxy-5-[2-(phenylsulfonyl)benzyl]phenanthridin-6(5H)-one
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95% inhibition at 0.01 mM
2,4,5-trimethyl-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
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2,4-dimethyl-3-methylidene-5-(pyridin-2-ylmethyl)-1,2,3,5-tetrahydro-6H-pyrazolo[4,3-c]pyridin-6-one
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2-(1,3-benzothiazol-2-yl)-1-(2-chlorobenzyl)-4-methyl-5-(morpholin-4-yl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
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2-(1,3-benzothiazol-2-yl)-4-ethyl-5-(2-methoxyethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
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2-(1,3-benzothiazol-2-yl)-4-methyl-1-(pyridin-2-ylmethyl)-5-(tetrahydrofuran-2-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
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2-(1,3-benzothiazol-2-yl)-4-methyl-5-(morpholin-4-yl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
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2-(1,3-benzothiazol-2-yl)-5-[2-(1H-imidazol-4-yl)ethyl]-4-methyl-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
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2-(1,3-benzothiazol-2-yl)-5-[2-(1H-indol-3-yl)ethyl]-4-methyl-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
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2-(2,5-dichlorobenzyl)-4-methyl-3-methylidene-5-(pyridin-2-ylmethyl)-1,2,3,5-tetrahydro-6H-pyrazolo[4,3-c]pyridin-6-one
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2-(2-chloro-4-fluorobenzyl)-4-methyl-3-methylidene-5-(pyridin-2-ylmethyl)-1,2,3,5-tetrahydro-6H-pyrazolo[4,3-c]pyridin-6-one
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2-(2-chloro-4-fluorophenyl)-4,5-dimethyl-1H-pyrazolo[4,3-c]-pyridine-3,6(2H,5H)-dione
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2-(2-chloro-4-fluorophenyl)-4-methyl-5-(pyridin-2-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
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2-(2-chloro-4-fluorophenyl)-5-(2-pyridin-2-ylethyl)-4-(pyrrolidin-1-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
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2-(2-chlorophenyl)-4,5-dimethyl-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
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2-(2-chlorophenyl)-4-(2-fluorophenyl)-5-methyl-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
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2-(2-chlorophenyl)-4-([methyl(phenyl)amino]methyl)-5-[2-(pyridin-2-yl)ethyl]-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
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2-(2-chlorophenyl)-4-methyl-5-(3-phenylprop-2-yn-1-yl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
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2-(2-chlorophenyl)-4-methyl-5-(4-[(4-methylpiperazin-1-yl)methyl]benzyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
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2-(2-chlorophenyl)-4-methyl-5-(pyridin-2-ylmethyl)-1H-pyrazolo-[4,3-c]pyridine-3,6(2H,5H)-dione
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2-(2-chlorophenyl)-4-methyl-5-[(6-morpholin-4-ylpyridin-2-yl)-methyl]-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
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2-(2-chlorophenyl)-4-methyl-5-[4-(4-methylpiperazin-1-yl)-4-oxobutyl]-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
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-
2-(2-chlorophenyl)-4-[(4-fluorophenoxy)methyl]-5-methyl-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
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2-(2-chlorophenyl)-4-[[4-(3-methoxyphenyl)piperazin-1-yl]-methyl]-5-methyl-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
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2-(2-chlorophenyl)-4-[[methyl(phenyl)amino]methyl]-5-(pyridin-4-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
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2-(2-chlorophenyl)-5-(3-ethoxypropyl)-4-methyl-1-(pyridin-2-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
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2-(2-chlorophenyl)-5-(3-hydroxypropyl)-4-methyl-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
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-
2-(2-chlorophenyl)-5-(cyclohexylmethyl)-4-methyl-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
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-
2-(2-chlorophenyl)-5-[(1-methyl-1H-pyrazol-3-yl)methyl]-4-[[methyl(pyridin-3-ylmethyl)amino]methyl]-1H-pyrazolo[4,3-c]-pyridine-3,6(2H,5H)-dione
-
-
2-(2-chlorophenyl)-5-[2-(dimethylamino)ethyl]-4-methyl-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
-
2-(2-fluorophenyl)-4,5-dimethyl-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
-
2-(2-methoxyethyl)-4-methyl-3-methylidene-5-(pyridin-2-ylmethyl)-1,2,3,5-tetrahydro-6H-pyrazolo[4,3-c]pyridin-6-one
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-
2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-6-methoxy-4H-chromen-4-one
-
complete inhibition at 0.01 mM
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one
-
complete inhibition at 0.01 mM
2-(3,4-dihydroxyphenyl)-5-hydroxy-3,7-dimethoxy-4H-chromen-4-one
-
88% inhibition at 0.01 mM
2-(3-chlorophenyl)-4,5-dimethyl-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
-
2-(4-chlorobenzyl)-4-methyl-3-methylidene-5-(pyridin-2-ylmethyl)-1,2,3,5-tetrahydro-6H-pyrazolo[4,3-c]pyridin-6-one
-
-
2-(4H-3,1-benzothiazin-2-yl)-1-benzyl-4-methyl-5-(tetrahydrofuran-2-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
-
2-(7-chloroquinolin-4-yl)-4-methyl-3-methylidene-5-(pyridin-2-ylmethyl)-1,2,3,5-tetrahydro-6H-pyrazolo[4,3-c]pyridin-6-one
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2-benzyl-4-methyl-3-methylidene-5-(pyridin-2-ylmethyl)-1,2,3,5-tetrahydro-6H-pyrazolo[4,3-c]pyridin-6-one
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-
2-bromohexadecanal
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irreversible
2-hydroxy-5-[(2-hydroxybenzyl)amino]benzoic acid
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89% inhibition at 0.01 mM
2-iodohexadecanal
-
irreversible
2-iodoicosanal
-
weak inhibition
2-iodooctanal
-
irreversible
2-[(2,3,8,9-tetrahydroxy-6-oxophenanthridin-5(6H)-yl)methyl]benzonitrile
-
97% inhibition at 0.01 mM
2-[(2E)-2-(3,4-dihydroxybenzylidene)hydrazinyl]-N-(3-nitrophenyl)-2-oxoacetamide
-
96% inhibition at 0.01 mM
2-[2-(4-chlorophenoxy)ethyl]-4-methyl-3-methylidene-5-(pyridin-2-ylmethyl)-1,2,3,5-tetrahydro-6H-pyrazolo[4,3-c]pyridin-6-one
-
-
2-[4-(benzyloxy)phenyl]-4,5-dimethyl-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
-
3'-(or 4'-)methylluteolin
-
-
3'-O-methyl epicatechin
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3,5,7-trihydroxy-2-(4-hydroxy-3-methylphenyl)-4H-chromen-4-one
-
94% inhibition at 0.01 mM
3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
-
complete inhibition at 0.01 mM
3-(3,4-dihydroxycyclohexa-2,4-dien-1-yl)-2,7-dihydroxy-4H-chromen-4-one
-
86% inhibition at 0.01 mM
3-(3-chlorophenyl)-N-[2-(piperazin-1-yl)phenyl]-1,4,6,7-tetrahydro-5H-pyrazolo[4,3-c]pyridine-5-carboxamide
-
Shionigi compound
3-(3-chlorophenyl)-N-[4-(piperidin-4-yl)phenyl]pyrazolo[1,5-a]pyrimidine-5-carboxamide
-
-
3-(4,5-dimethyl-3,6-dioxo-1,3,5,6-tetrahydro-2H-pyrazolo[4,3-c]pyridin-2-yl)benzonitrile
-
-
4'-O-methyl epicatechin
-
-
4,5-dimethyl-2-(4-phenyl-1,3-thiazol-2-yl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
-
4,5-dimethyl-2-(5-[(4-methylpiperazin-1-yl)sulfonyl]pyridin-2-yl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
-
4-(2-amino-ethyl)-benzolsulphonyl-fluoride
-
4-(2-aminoethyl)-benzenesulfonyl fluoride
-
-
4-(2-aminoethyl)benzenesulfonyl fluoride
-
significantly reduces reactive oxygen species production, NADPH oxidase activity, and all the apoptotic events, and cell death induced by both 5 mM KCl and staurosporin
4-methyl-2-(2-methylphenyl)-5-(pyridine-2-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
-
4-methyl-2-phenyl-5-(2-phenylethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
-
4-methyl-2-phenyl-5-(pyridin-3-ylmethyl)-1H-pyrazolo[4,3-c]-pyridine-3,6(2H,5H)-dione
-
-
-
4-methyl-3-methylidene-2-(2-phenylethyl)-5-(pyridin-2-ylmethyl)-1,2,3,5-tetrahydro-6H-pyrazolo[4,3-c]pyridin-6-one
-
-
4-methyl-3-methylidene-2-[2-(morpholin-4-yl)ethyl]-5-(pyridin-2-ylmethyl)-1,2,3,5-tetrahydro-6H-pyrazolo[4,3-c]pyridin-6-one
-
-
4-methyl-5-(3-phenoxybenzyl)-2-([1,2,4]triazolo[4,3-b]pyridazin-6-yl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
-
4-[(4-fluorophenoxy)methyl]-5-(2-methoxyethyl)-2-(2-morpholin-4-ylethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
-
4-[(benzyloxy)methyl]-2-(2-chlorophenyl)-5-(pyrazin-2-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
-
4-[[(2-chlorobenzyl)oxy]methyl]-2-(2-chlorophenyl)-5-methyl-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
-
4-[[2-(1,3-benzothiazol-2-yl)-4-methyl-3,6-dioxo-1,2,3,6-tetrahydro-5H-pyrazolo[4,3-c]pyridin-5-yl]methyl]benzoic acid
-
-
4-[[2-(2-chlorophenyl)-4-methyl-3,6-dioxo-1,2,3,6-tetrahydro-5H-pyrazolo[4,3-c]pyridin-5-yl]methyl]benzenesulfonamide
-
-
4-[[benzyl(methyl)amino]methyl]-2-(2-chloro-4-fluorophenyl)-5-(3-methoxypropyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
-
5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
-
complete inhibition at 0.01 mM
5-(1,3-benzodioxol-5-ylmethyl)-4-methyl-2-phenyl-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
-
5-(E)-6,9-deoxa-6,9alpha-methylene-15-cyclopentyl-16,17,18,19,20-pentanor-prostaglandin I2
-
inhibition of sodiumdodecylsulfate-induced activation in cell free extracts, 0.17 mM, 50% inhibition
5-(furan-2-ylmethyl)-4-methyl-2-phenyl-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
-
5-benzyl-2-(4-fluorophenyl)-4-methyl-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
-
5-cyclopropyl-2-[1-(2-fluoro-benzyl)-1H-pyrazolo[3,4-b]pyridine-3-yl]pyrimidin-4-ylamine
-
i.e. BAY 41-2272, inhibits the induction of the expression of subunits p22phox and gp91phox by 11alpha,9alpha-epoxymethanoprostaglandin F 2alpha. Enhances nitric oxide-induced relaxations in a concentration-dependent manner
5-[(2,5-dihydroxybenzyl)amino]-2-hydroxybenzoic acid
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82% inhibition at 0.01 mM
abruquinone C
-
-
-
alpha-chymotrypsin
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desensitization of activity to Ca2+
-
aminoethylbenzenesulfonylfluoride
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treatment blocks the induction of reactive oxygen species production by the dopaminergic toxin MPP+. Co-treatment with inhibitors aminoethylbenzenesulfonylfluoride, apocynin, or diphenylene iodinium significantly suppresses MPP*-induced cell death and attenuates MPP*-induced increases in caspase-3 enzymatic activity
angiotensin
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angiotensin-(1-7) decreases the elevated levels of renal NADPH oxidase activity and attenuates the activation of subunit NOX-4 gene expression in the diabetic hypertensive kidney. Angiotensin-(1-7) treatment increases sodium excretion but does not affect mean arterial pressure in diabetic hypertensive rats. The significant increase in urinary protein in the diabetic compared to control hypertensive rat is reduced by angiotensin-(1-7). Angiotensin-(1-7) treatment also attenuates the diabetes-induced increase in renal vascular responsiveness to endothelin-1, norepinephrine, and angiotensin II in hypertensive rats, but significantly increases the vasodilation of the renal artery of hypertensive and diabetic hypertensive rats to the vasodilator agonists
apocynin
ATDITGPIILQTYRA
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a peptide inhibitor derived from human p47phox
AYRRNSVRFL
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inhibits NADPH oxidase activation
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AYRRNSVRFVRFLN
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a peptide inhibitor derived from human p47phox
betaPix
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guanine nucleotide exchange factor, overexpression of the central PH domain of betaPix results in inhibition of superoxide anion generation in response to EGF
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betulinic acid
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attenuates the expression of NAD(P)H oxidase subunits Nox4 and p22phox, thereby reducing oxidative stress and improving endothelial nitric oxide synthase function. Treated cells show in increased production of bioactive nitric oxide
bilirubin
Cd2+
-
-
Cdc42
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a small monomeric GTPase, competitive inhibitor of Nox2, might also be a competitive inhibitor of Nox1
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CERLVRFWRSQQKVV
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a peptide inhibitor derived from human gp91phox/NOX2
CoA
NADH-dependent oxidase activities is strongly inhibited by addition of free CoA, whereas NADPH dependent activity is not; NADH-dependent oxidase activities is strongly inhibited by addition of free CoA, whereas NADPH dependent activity is not; NADH-dependent oxidase activities is strongly inhibited by addition of free CoA, whereas NADPH dependent activity is not; NADH-dependent oxidase activities is strongly inhibited by addition of free CoA, whereas NADPH dependent activity is not
COMT-methylated procyanidin B2
-
-
-
CSTRVRRQLDRNLTFHK
-
a peptide inhibitor derived from human gp91phox/NOX2
dihydrokaempferol
-
-
dihydrotamarixetin
-
-
diosmetin
-
-
diphenylene iodinium
diphenylene iodinium chloride
diphenylene iodonium
diphenyleneiodonium
diphenyliodonium
-
-
dodecanal
-
reversible
DTNB
-
-
EGTA
-
almost complete inhibition at 0.5 mM
endothelin-1
-
inhibits NADPH oxidase activity, superoxide generation, and cell proliferation in human abdominal aortic endothelial cells via the ETB1-Pyk2-Rac1-Nox1 pathway. Endothelin-1 significantly attenuates NADPH oxidase activity and cell proliferation, which can be abolished by silencing of the Nox1 gene. RNA interference silencing of ETB1 receptors significantly increases NADPH oxidase activity, and blocks the inhibitory effect of endothelin-1 on NADPH oxidase activity. Endothelin-1 also attenuates angiotensin II-induced activation of NADPH oxidase and cell proliferation
Epicatechin gallate
-
-
epigallocatechin
-
-
epigallocatechin gallate
-
-
FAVHHDEEDVITG
-
a peptide inhibitor derived from human gp91phox/NOX2
FAVHHDEEKDVITG
-
-
-
ferulic acid
-
-
FIRHIALLGFEKRFV
-
a peptide inhibitor derived from human p47phox
FLRGSSACCSTRVRRQL
fulvene-5
-
GK-136901
-
inhibition of NOX1 and NOX4
gliotoxin
-
-
gomisin C
-
-
-
gp91ds
-
fusion peptide that inhibits assembly of NADPH oxidase by mimicking the gp91phox docking site for the cytoplasmic p47phox subunit. gp91ds prevents NADPH oxidase activity, cytokine release, and neurotoxicity induced by HIV regulatory protein Tat in primary microglia
-
gp91ds-tat
Hemin
-
hemin treatment increases hemin oxidase-1 expression and activity in aorta and kidney of apolipoprotein E–deficient mice and significantly reduces both NADPH oxidase activity and superoxide generation in situ
hesperetin
-
-
hexadecanal
-
reversible
honokiol
IRNAHSIHQRSRKRL
-
a peptide inhibitor derived from human p47phox
ISNSESGPRGVHFIFNKENF
-
a peptide inhibitor derived from human gp91phox/NOX2
isorhamnetin
-
-
isorhamnetin glucuronide
-
-
KTIELQMKKKGFKM
-
a peptide inhibitor derived from human gp91phox/NOX2
LKLKKIYFYWLCRDTHAF
-
a peptide inhibitor derived from human gp91phox/NOX2
LKSVWYKYCN
-
a peptide inhibitor derived from human gp91phox/NOX2
LKSVWYKYCNN
-
a peptide inhibitor derived from human gp91phox/NOX2
lucensomycin
-
0.02 mM, 50% inhibition
magnolol
-
-
methimazol
-
partial
methyl 2-hydroxy-5-[(2-hydroxybenzyl)amino]benzoate
-
91% inhibition at 0.01 mM
ML171
-
inhibition NOX1
Mn2+
-
-
N'1,N'2-bis[(E)-(2,3-dihydroxyphenyl)methylidene]ethanedihydrazide
-
complete inhibition at 0.01 mM
N'1,N'2-bis[(E)-(3,4-dihydroxyphenyl)methylidene]ethanedihydrazide
-
complete inhibition at 0.01 mM
N-(1-cyclohexylethyl)-4-phenylphthalazin-1-amine
-
-
N-(3-aminophenyl)-N'-[1-(4-hydroxy-3-methoxyphenyl)ethyl]ethanediamide
-
complete inhibition at 0.01 mM
N-ethylmaleimide
N-[(3Z)-3-(4-hydroxy-3-methoxybenzylidene)-2-oxo-2,3-dihydro-1H-indol-5-yl]acetamide
-
complete inhibition at 0.01 mM
N-[1-(3,4-dihydroxyphenyl)ethyl]-N'-(3-nitrophenyl)ethanediamide
-
complete inhibition at 0.01 mM
N-[2-(2-chlorophenyl)-4-methyl-3,6-dioxo-1,2,3,6-tetrahydro-5H-pyrazolo[4,3-c]pyridin-5-yl]-2-(4-fluorophenoxy)acetamide
-
-
N-[2-(4-hydroxy-phenyl)-ethyl]-2-(2, 5-dimethoxy-phenyl)-3-(3-methoxy-4-hydroxy-phenyl)-acrylamide
N-[3-(4,5-dimethyl-3,6-dioxo-1,3,5,6-tetrahydro-2H-pyrazolo[4,3-c]pyridin-2-yl)phenyl]acetamide
-
-
N4-(3-aminophenyl)[1]benzothieno[3,2-d]pyrimidine-4,8-diamine
-
98% inhibition at 0.01 mM
N4-(4-aminophenyl)[1]benzothieno[3,2-d]pyrimidine-4,8-diamine
-
complete inhibition at 0.01 mM
naringenin
-
-
neopterin
nitroglycerin
-
in rats treated with nitroglycerin for three days, superoxide production is increased in all aortic layers, while expression of isoforms nox1, nox2 and nox4 is significantly decreased. In vascular smooth muscle cells exposed to nitroglycerin for 6-24 h, NAD(P)H oxidase activity is increased, in spite of nox1 downregulation
norathyriol
-
-
-
Nox2ds-tat
-
inhibition of NAOX1 and NOX2
-
O-methyl-epicatechin
-
inhibits endothelial NAD(P)H oxidase activity and prevents superoxide anion formation
-
p-chloromercuribenzoate
-
-
p-hydroxymercuribenzoate
-
-
perhexilline
-
-
-
pg91ds-tat
-
-
-
phallacidin
-
pretreatment of human pulmonary artery endothelial cells before induction of hyperoxia attenuates hyperoxia-induced cortical actin thickening and reactive oxygen species production
Phenylarsine oxide
Plumbagin
-
inhibition of NOX4
procyanidin B2
-
acts both as a superoxide anion scavenger, and inhibitory to NAD(P)H oxidase, with apocynin-like mode of NADPH oxidase inhibition
prodigiosin
-
-
propylthiouracil
-
partial
prostaglandin E1
-
inhibition of sodiumdodecylsulfate-induced activation in cell free extracts, 0.044 mM, 50% inhibition
PTKISRCPPHLLDFFK
-
a peptide inhibitor derived from human p47phox
QRRRQARPGPQSPG
-
a peptide inhibitor derived from human p47phox
quercetin 3-O-alpha-D-glucopyranoside
-
complete inhibition at 0.01 mM
quercetin glucuronide
-
-
RFVPSQHYVYMFLVK
-
a peptide inhibitor derived from human p47phox
RGVHFIF
rosiglitazone
rosuvastatin
-
rosuvastatin reduces systolic blood pressure in spontaneously hypertensive rats but does not change plasma lipid levels. Rosuvastatin treatment in spontaneously hypertensive rats significantly decreases reactive oxygen species levels, NAD(P)H activity in retinal ganglion cells, and increases retinal plasmalogen content in spontaneously hypertensive rats, but does not modify the electroretinogram response
RRNSVRFLQQRRRQA
-
a peptide inhibitor derived from human p47phox
RRSSIRNAHSIHQRSRKRLS
-
a peptide inhibitor derived from human p47phox
RSRKRLSQDAYRRNSVRF
-
RSRKRLSQDAYRRNSVRFLQQR
-
a peptide inhibitor derived from human p47phox
S17834
-
-
-
sepiapterin
-
induction of oxidative stress, p22phox mRNA, endothelial nitric oxide synthase mRNA, and protein by glucose are lowered by concurrent incubation with sepiapterin
sinomenine
-
morphinan analog, inhibits NAD(P)H oxidase cytosolic subunit p47phox translocation to the cell membrane and thus reduces lipopolysaccharide-induced extracellular reactive oxygen species production. Protects neuron-glial cell cultures at both micro- and sub-picomolar concentrations against dopaminergic neuron death, but not protection is seen at nanomolar concentrations
SNSESGPRGVHFIFNKEN
-
-
-
Sodium deoxycholate
-
no activity at 5 mg/ml
SRKRLSQDAYRRNS
-
a peptide inhibitor derived from human p47phox
STRVRRQLDRNLTF
-
a peptide inhibitor derived from human gp91phox/NOX2
sulfosuccinimidyl-3-(4-hydroxyphenyl) propionate
-
-
tamarixetin
-
-
taxol
-
induces concentration-dependent neuronal death with apoptotoic features. Neuronal death is significantly attenuated by anti-apoptotic rugs and by antioxidants such as trolox, ascorbic acid, and tempol. Exposure to taxol increases the expression of NAD(P)H oxidase subunits p45phox and gp91phox and induces translocation of p47phox protein to the membrane in cortical cultures
telmisartan
-
0.01 mM telmisartan decreases NAD(P)H oxidase activity by 32% in MIN-6 cells
tetramethylpyrazine
-
inhibits the induction of NAD(P)H oxidase activity by angiotensin II and the concomitant increase of intracellular reactive oxygen species levels and ERK phosphorylation
tridecanal
-
reversible
Triton X-100
-
no activity at 2 mg/ml
VAS2870
VAS3947
VWYYRVYDIPPKFFYTRKLL
-
a peptide inhibitor derived from human gp91phox/NOX2
WWFCQMKAKRGWIPA
-
a peptide inhibitor derived from human p47phox
Zn2+
-
-
additional information
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(+)-(S)-2-(6-methoxynaphthalen-2-yl)propanoic acid
11alpha,9alpha-epoxymethanoprostaglandin F 2alpha
-
induces the expression of subunits p22phox and gp91phox
2,4,6-trinitrophenyl-bovine serum albumin
-
induces reactive oxygen species generation, which occurrs immediately. 2,4,6-Trinitrophenyl-bovine serum albumin but not TG causes extracellular release of superoxide anion/hydrogen peroxide, which is blocked by diphenyleneiodonium, apocynin, and wortmannin. When used together, 2,4,6-trinitrophenyl-bovine serum albumin and thapsigargin evoke the release of leukotriene C4, tumor necrosis factor-alpha, and interleukin-13 as well as reactive oxygen species generation synergistically
-
2,6-dichlorophenolindophenol
-
-
2-(2-(2,6-dichlorophenylamino)-phenyl)acetic acid
4-(4-methylsulfonylphenyl)-3-phenyl-5H-furan-2-one
4-[5-(4-methylphenyl)-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide
5-cyclopropyl-2-[1-(2-fluoro-benzyl)-1H-pyrazolo[3,4-b] pyridin-3-yl]-pyrimidin-4-ylamine
-
i.e. BAY 41-2272. THP-1 cells treated with BAY 41-2272 for 48 h significantly increase the superoxide anion release. BAY 41-2272 increases subunit gp91phox gene expression and causes a significant increase in cGMP and cAMP levels
8-bromo-cAMP
-
can replace for thyrotropin
A23127
-
a calcium ionophore
-
A23187
-
calcium ionophore. HaCaT keratinocytes overexpressing calcium- and arachidonic acid binding proteins S100A8/S100A9 showed enhanced, transient reactive oxygen species generation in response to A23187, as well as nuclear factor kappaB activation and increase in interleukin-8 mRNA levels
angiotensin II
apigenin
-
apigenin reduces cell viability, and induces apoptotic cell death in a dose-dependent manner. In addition, it evokes a dose-related elevation of intracellular reactive oxygen species level. Treatment with various inhibitors of the NADPH oxidase significantly blunts both the generation of reactive oxygen species and induction of apoptosis induced by apigenin
arachidonic acid
-
maximal enzyme activity in the presence of 0.25-0.35 mM, inhibition above
ATP
-
2fold activation
betaPix
-
a Rac1 guanine nucleotide exchange factor, appears to be constitutively bound to Nox1 and essential for its activity
-
bovine serum albumin
-
time-dependent increases in NAD(P)H oxidase activity with bovine serum albumin stimulation that is inhibited in a concentration-dependent manner with the HMG-CoA reductase inhibitor rosuvastatin, or with Rac1 inhibitor NSC23766. Following albumin stimulation, Rac1 translocates to plasma membrane for NAD(P)H oxidase activation
-
calyculin
isoform RbohD is directly phosphorylated in vivo. Phophorylation is enhanced in presence of protein phosphatase inhibitor calyculin. Calyculin itself induces reactive oxygen species production and dramatically enhances the ionomycin-induced reactive oxygen species production of isoform RbohD
cytochalasin D
-
enhancement of basal and hyperoxia-induced reactive oxygen species formation
cytochrome c
-
-
doxorubicin
-
induction of superoxide production by doxorubicin is much higher in hearts of wild-type mice than in subunit gp91phox knock-out mice
formyl-Met-Leu-Phe
forskolin
glucose
-
oxidative stress and expression of the NADPH oxidase subunit, p22phox, are both increased, superoxide dismutase 1 and 3 expression lowered and endothelial nitric oxide synthase significantly elevated in microvessel endothelial cells treated with 40mM glucose for 72 h compared to low glucose medium. Oxidative stress, p22phox mRNA, endothelial nitric oxide synthase mRNA, and protein are lowered by concurrent incubation with sepiapterin
GTP-gammaS
-
optimal concentration approx. 0.015 mM
H2O2
-
Nox5 can be upregulated and activated by minute concentrations of hydrogen peroxide
heat shock protein 90
-
binding of heat shock protein 90 to the C-terminus of Nox5 appears to stabilize the protein and enhance expression and activity
-
HIV regulatory protein Tat
-
NADPH oxidase mediates Tat-induced superoxide release in microglia and macrophages
-
Interleukin-1beta
-
stimulates Nox1
-
ionomycin
isoobtusilactone A
-
isoobtusilactone A elicits a concentration-dependent growth impediment with IC50 value of 37.5 microM. Treated cells also display transient increase of reactive oxygen species during the earlier stage of the experiment, followed by the disruption of mitochondrial transmembrane potential. The presence of a reactive oxygen species scavenger N-acetyl-L-cysteine and the inhibitor of NADPH oxidase diphenyleneiodonium chloride block reactive oxygen species production and the subsequent apoptotic cell death
latrunculin A
-
enhancement of basal and hyperoxia-induced reactive oxygen species formation
lipopolysaccharide
-
exposure tolipopolysaccharide leads to the demise of motor neurons in a dose- and time-dependent manner, whereas interneurons are impaired relatively mildly. NADPH oxidase is activated upon lipopolysaccharide challenge, and inhibitor apocynin prevents inflammation-mediated toxicity to motor neurons
menadione
-
-
N-formyl-L-methionyl-L-leucyl-L-phenylalanine
NaCl
-
salt stress results in activiation of plasma membrane NAD(P)H oxidase. NaCl-induced increase in total Ca2+ is partially abolished by the addition of NAD(P)H oxidase inhibitor diphenyleneiodinium
nitroglycerin
-
in vascular smooth muscle cells exposed to nitroglycerin for 6-24 h, NAD(P)H oxidase activity is increased, in spite of isoform nox1 downregulation
NOXA1
-
NOXO1
-
p67phox
-
activation domain of p67phox triggers FAD reduction by Nox2. P40phox appears to increase oxidase activity in cooperation with p47phox not by inducing translocation to the membrane, but by retaining the oxidase at the phagosome
-
paraquat
-
paraquat-induced reactive oxygen species production including superoxide anions in BV-2 cells is accompanied by translocation of the p67phox cytosolic subunit of NADPH oxidase to the membrane. Paraquat-induced reactive oxygen species production is inhibited by NADPH oxidase inhibitors, apocynin and diphenylene iodonium. Apocynin and diphenylene iodonium also rescue cells from paraquat-induced toxicity. The inhibitors for protein kinase C delta or extracellular signal-regulated kinases ERK1/2 can partially attenuate paraquat-induced reactive oxygen species production and cell death
peptide C5a
-
-
-
phorbol 12-myristate 13-acetate
phorbol myristate acetate
-
-
phosphate
phosphatidylinositol 3-phosphate
-
subunit p40phox phosphatidylinositol 3-phosphate binding PX domain has phosphatidylinositol 3-phosphate-dependent and -independent functions. Translocation of subunit p67phox requires the PX domain but not 3-phosphoinositide binding. Activation of the oxidase by p40phox, however, requires both phosphatidylinositol 3-phosphate binding and an Src homology 3 domain competent to bind to poly-Pro ligands
platelet-derived growth factor
-
increases H2O2 production in NIH-3T3 fibroblasts through NADPH oxidase activation mediated by Gi-protein coupled receptors and c-Src kinase
-
Poldip2
-
reactive oxygen species production is enhanced by the multifunctional Poldip2, which also interacts with p22phox, presumably at the beginning of the cytosolic C-terminus, upstream of the region dispensable for Nox4 activity
-
Protein kinase C
-
-
-
Rac guanine nucleotide exchange factors
-
activate in conjunction with ATP and nucleoside diphosphate kinase
-
Rac1
-
in addition to cytosolic organizers and activators, Nox1 also requires Rac1 for activity. Rac1 interacts directly with the C-terminus of Nox1, even in the absence of Noxa1. Nox1 is stimulated by constitutively active Rac1 and inhibited by Rac1 knockdown. Rac1 provides a crucial mechanism for activation by agonists, particularly in cells that exclusively express Nox1/Noxo1/Noxal. Rac1 does not activate Nox4 in transfected cells. Rac1 may participate in Nox5 activation
-
salbutamol
-
salbutamol treatment enhances superoxide anion production in asthma patients through nitric oxide-mediated mechanisms. It exerts beneficial antioxidant effects through activation of catalase and attenuation of lipid peroxidation
sodiumdodecylsulfate
-
-
sphingosine 1-phosphate
-
increases H2O2 production in NIH-3T3 fibroblasts through NADPH oxidase activation mediated by Gi-protein coupled receptors and c-Src kinase
thapsigargin
-
evokes a robust burst of intracellular reactive oxygen specie, which occurrs with a significant lag tim. When used together, 2,4,6-trinitrophenyl-bovine serum albumin and thapsigargin evoke the release of leukotriene C4, tumor necrosis factor-alpha, and interleukin-13 as well as reactive oxygen species generation synergistically
thrombin
-
thyrotropin
-
TNF-alpha
-
transforming growth factor-beta
-
up-regulates isoform nox4 and increases the levels of Rac1 protein, a known regulator of both isoforms Nox1 and Nox2, in a transforming growth factor-beta receptor I-dependent manner and mediates activation of the nuclear factor-kappaB pathway. The inhibitors diphenyleneiodonium and apocynin, and SB431542, an inhibitor of the transforming growth factor-beta receptor I, block up-regulation of epidermal growth factor receptor ligands and Akt activation
-
Trp-Lys-Tyr-Met-Val-Met
-
activates
tumor necrosis factor
-
treatment of fibroblasts induces the formation of a signaling complex containing TNF-R1-associated death domain protein TRADD, receptor interacting protein RIP1, NAD(P)H oxidase Nox1, and the small GTPase Rac1. Formation of this complex plays a key role in tumor necrosis factor-induced necrotic cell death
-
tumor necrosis factor-alpha
-
treatment of monocytic cells and isolated monocytes results in up-regulation of the NAD(P)H oxidase gene, neutrophil cytosolic factor 2. Treated cells have increased levels of mRNA and up-regulated expression of NADPH oxidase subunits p47phox, p67phox, and gp91phox, as well as increased oxidase activity. Pharmacological inhibitors of NF-kappaB activation block tumor necrosis factor-induced up-regulation, which correlates with a reduction in expression of the corresponding oxidase proteins and decreased superoxide anion production
-
Urea
-
increase of activity by 250% in presence of 1 M urea with no apparent perturbation in enzyme structure. Presence of urea prohibits the closing of the active site thus allowing the substrate to bind
additional information
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.1 - 0.413
NADH
0.01 - 0.1
NADPH
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
4.4
NADH
Sulfolobus solfataricus
-
pH 5.5, 65°C
2.8
NADPH
Helicobacter pylori
-
at 25°C, pH not specified in the publication
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
10.7
NADH
Sulfolobus solfataricus
-
pH 5.5, 65°C
8
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0000301
(1R)-1-[(2R,2'R,5R,5'R)-5'-[(1R)-1-hydroxyundec-3-yn-1-yl]octahydro-2,2'-bifuran-5-yl]dodec-4-yn-1-ol
-
-
0.0000123
(1R)-1-[(2R,2'R,5R,5'R)-5'-[(1R)-1-hydroxyundecyl]octahydro-2,2'-bifuran-5-yl]dodecan-1-ol
-
-
0.0000388
(1R,1'R)-1,1'-((2R,2'R,5R,5'R)-octahydro-2,2'-bifuran-5,5'-diyl)-bis-(6-(4-n-butylphenoxy)hex-3-yn-1-ol)
-
-
0.0000196
(1R,1'R)-1,1'-((2R,2'R,5R,5'R)-octahydro-2,2'-bifuran-5,5'-diyl)-bis-(6-(4-n-butylphenoxy)hexan-1-ol)
-
-
0.03
1-(2-chlorobenzyl)-4-methyl-5-[3-(2-oxopyrrolidin-1-yl)propyl]-2-phenyl-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
Ki above 0.03 mM, 0.1 M phosphate buffer, pH 7.4, 37°C
0.03
1-(4-fluorobenzyl)-5-[2-(1H-indol-3-yl)ethyl]-4-methyl-2-phenyl-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
Ki above 0.03 mM, 0.1 M phosphate buffer, pH 7.4, 37°C
0.00024
1-acetyl-2-(2-chlorophenyl)-4-methyl-5-(pyridin-3-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.000398
1-acetyl-4-methyl-2-(2-methylphenyl)-5-(pyridin-3-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.000409
1-acetyl-4-methyl-2-phenyl-5-(pyridin-3-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.000285
1-[(3-methoxyphenyl)acetyl]-4-methyl-2-phenyl-5-(pyridin-3-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.002175
2,4,5-trimethyl-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.000387
2,4-dimethyl-3-methylidene-5-(pyridin-2-ylmethyl)-1,2,3,5-tetrahydro-6H-pyrazolo[4,3-c]pyridin-6-one
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.03
2-(1,3-benzothiazol-2-yl)-1-(2-chlorobenzyl)-4-methyl-5-(morpholin-4-yl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
Ki above 0.03 mM, 0.1 M phosphate buffer, pH 7.4, 37°C
0.03
2-(1,3-benzothiazol-2-yl)-4-methyl-1-(pyridin-2-ylmethyl)-5-(tetrahydrofuran-2-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
Ki above 0.03 mM, 0.1 M phosphate buffer, pH 7.4, 37°C
0.001208
2-(1,3-benzothiazol-2-yl)-4-methyl-5-(morpholin-4-yl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.004729
2-(1,3-benzothiazol-2-yl)-5-[2-(1H-imidazol-4-yl)ethyl]-4-methyl-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.001845
2-(1,3-benzothiazol-2-yl)-5-[2-(1H-indol-3-yl)ethyl]-4-methyl-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.000218
2-(2,5-dichlorobenzyl)-4-methyl-3-methylidene-5-(pyridin-2-ylmethyl)-1,2,3,5-tetrahydro-6H-pyrazolo[4,3-c]pyridin-6-one
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.000342
2-(2-chloro-4-fluorobenzyl)-4-methyl-3-methylidene-5-(pyridin-2-ylmethyl)-1,2,3,5-tetrahydro-6H-pyrazolo[4,3-c]pyridin-6-one
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.000213
2-(2-chloro-4-fluorophenyl)-4,5-dimethyl-1H-pyrazolo[4,3-c]-pyridine-3,6(2H,5H)-dione
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.000235
2-(2-chloro-4-fluorophenyl)-4-methyl-5-(pyridin-2-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.000114
2-(2-chloro-4-fluorophenyl)-5-(2-pyridin-2-ylethyl)-4-(pyrrolidin-1-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.000215
2-(2-chlorophenyl)-4,5-dimethyl-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
0.1 M phosphate buffer, pH 7.4, 37°C
-
0.000128
2-(2-chlorophenyl)-4-(2-fluorophenyl)-5-methyl-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.000172
2-(2-chlorophenyl)-4-([methyl(phenyl)amino]methyl)-5-[2-(pyridin-2-yl)ethyl]-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.000158
2-(2-chlorophenyl)-4-methyl-5-(3-phenylprop-2-yn-1-yl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.000515
2-(2-chlorophenyl)-4-methyl-5-(4-[(4-methylpiperazin-1-yl)methyl]benzyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.000165
2-(2-chlorophenyl)-4-methyl-5-(pyridin-2-ylmethyl)-1H-pyrazolo-[4,3-c]pyridine-3,6(2H,5H)-dione
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.000236
2-(2-chlorophenyl)-4-methyl-5-[(6-morpholin-4-ylpyridin-2-yl)-methyl]-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.000428
2-(2-chlorophenyl)-4-methyl-5-[4-(4-methylpiperazin-1-yl)-4-oxobutyl]-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.000114
2-(2-chlorophenyl)-4-[(4-fluorophenoxy)methyl]-5-methyl-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.000065
2-(2-chlorophenyl)-4-[[4-(3-methoxyphenyl)piperazin-1-yl]-methyl]-5-methyl-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.000151
2-(2-chlorophenyl)-4-[[methyl(phenyl)amino]methyl]-5-(pyridin-4-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.03
2-(2-chlorophenyl)-5-(3-ethoxypropyl)-4-methyl-1-(pyridin-2-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
Ki above 0.03 mM, 0.1 M phosphate buffer, pH 7.4, 37°C
0.000565
2-(2-chlorophenyl)-5-(3-hydroxypropyl)-4-methyl-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.00052
2-(2-chlorophenyl)-5-(cyclohexylmethyl)-4-methyl-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.000047
2-(2-chlorophenyl)-5-[(1-methyl-1H-pyrazol-3-yl)methyl]-4-[[methyl(pyridin-3-ylmethyl)amino]methyl]-1H-pyrazolo[4,3-c]-pyridine-3,6(2H,5H)-dione
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.000235
2-(2-chlorophenyl)-5-[2-(dimethylamino)ethyl]-4-methyl-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.000308
2-(2-fluorophenyl)-4,5-dimethyl-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.000313
2-(2-methoxyethyl)-4-methyl-3-methylidene-5-(pyridin-2-ylmethyl)-1,2,3,5-tetrahydro-6H-pyrazolo[4,3-c]pyridin-6-one
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.00034
2-(3-chlorophenyl)-4,5-dimethyl-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.000259
2-(4-chlorobenzyl)-4-methyl-3-methylidene-5-(pyridin-2-ylmethyl)-1,2,3,5-tetrahydro-6H-pyrazolo[4,3-c]pyridin-6-one
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.03
2-(4H-3,1-benzothiazin-2-yl)-1-benzyl-4-methyl-5-(tetrahydrofuran-2-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
Ki above 0.03 mM, 0.1 M phosphate buffer, pH 7.4, 37°C
0.000458
2-(7-chloroquinolin-4-yl)-4-methyl-3-methylidene-5-(pyridin-2-ylmethyl)-1,2,3,5-tetrahydro-6H-pyrazolo[4,3-c]pyridin-6-one
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.000463
2-benzyl-4-methyl-3-methylidene-5-(pyridin-2-ylmethyl)-1,2,3,5-tetrahydro-6H-pyrazolo[4,3-c]pyridin-6-one
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.000326
2-[2-(4-chlorophenoxy)ethyl]-4-methyl-3-methylidene-5-(pyridin-2-ylmethyl)-1,2,3,5-tetrahydro-6H-pyrazolo[4,3-c]pyridin-6-one
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.00306
2-[4-(benzyloxy)phenyl]-4,5-dimethyl-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.000293
3-(4,5-dimethyl-3,6-dioxo-1,3,5,6-tetrahydro-2H-pyrazolo[4,3-c]pyridin-2-yl)benzonitrile
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.001947
4,5-dimethyl-2-(4-phenyl-1,3-thiazol-2-yl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.001418
4,5-dimethyl-2-(5-[(4-methylpiperazin-1-yl)sulfonyl]pyridin-2-yl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.000173
4-methyl-2-(2-methylphenyl)-5-(pyridine-2-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.005232
4-methyl-2-phenyl-5-(2-phenylethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.000373
4-methyl-2-phenyl-5-(pyridin-3-ylmethyl)-1H-pyrazolo[4,3-c]-pyridine-3,6(2H,5H)-dione
-
0.1 M phosphate buffer, pH 7.4, 37°C
-
0.000334
4-methyl-3-methylidene-2-(2-phenylethyl)-5-(pyridin-2-ylmethyl)-1,2,3,5-tetrahydro-6H-pyrazolo[4,3-c]pyridin-6-one
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.000445
4-methyl-3-methylidene-2-[2-(morpholin-4-yl)ethyl]-5-(pyridin-2-ylmethyl)-1,2,3,5-tetrahydro-6H-pyrazolo[4,3-c]pyridin-6-one
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.03
4-methyl-5-(3-phenoxybenzyl)-2-([1,2,4]triazolo[4,3-b]pyridazin-6-yl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
Ki above 0.03 mM, 0.1 M phosphate buffer, pH 7.4, 37°C
0.000153
4-[(4-fluorophenoxy)methyl]-5-(2-methoxyethyl)-2-(2-morpholin-4-ylethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.000095
4-[(benzyloxy)methyl]-2-(2-chlorophenyl)-5-(pyrazin-2-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.000082
4-[[(2-chlorobenzyl)oxy]methyl]-2-(2-chlorophenyl)-5-methyl-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.004222
4-[[2-(1,3-benzothiazol-2-yl)-4-methyl-3,6-dioxo-1,2,3,6-tetrahydro-5H-pyrazolo[4,3-c]pyridin-5-yl]methyl]benzoic acid
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.000259
4-[[2-(2-chlorophenyl)-4-methyl-3,6-dioxo-1,2,3,6-tetrahydro-5H-pyrazolo[4,3-c]pyridin-5-yl]methyl]benzenesulfonamide
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.000165
4-[[benzyl(methyl)amino]methyl]-2-(2-chloro-4-fluorophenyl)-5-(3-methoxypropyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.00544
5-(1,3-benzodioxol-5-ylmethyl)-4-methyl-2-phenyl-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.00949
5-(furan-2-ylmethyl)-4-methyl-2-phenyl-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.000878
5-benzyl-2-(4-fluorophenyl)-4-methyl-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.031
methimazol
-
-
0.000218
N-[2-(2-chlorophenyl)-4-methyl-3,6-dioxo-1,2,3,6-tetrahydro-5H-pyrazolo[4,3-c]pyridin-5-yl]-2-(4-fluorophenoxy)acetamide
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.000328
N-[3-(4,5-dimethyl-3,6-dioxo-1,3,5,6-tetrahydro-2H-pyrazolo[4,3-c]pyridin-2-yl)phenyl]acetamide
-
0.1 M phosphate buffer, pH 7.4, 37°C
0.0002
p-chloromercuribenzoate
-
-
0.003
Phenylarsine oxide
-
3 nmol/mg protein
0.026
propylthiouracil
-
-
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0049
(-)-epicatechin glucuronide
Homo sapiens
-
25°C, pH 7.4, cell lysate
0.001
(2Z)-2-(5-hydroxy-4,6-dimethyl-2-oxo-1,2-dihydro-3H-indol-3-ylidene)-N,N-di(prop-2-en-1-yl)hydrazinecarbothioamide
Homo sapiens
-
pH and temperature not specified in the publication
0.00113
(3Z)-3-(3,4-dihydroxybenzylidene)-5-nitro-1,3-dihydro-2H-indol-2-one
Homo sapiens
-
pH and temperature not specified in the publication