Information on EC 1.10.5.1 - ribosyldihydronicotinamide dehydrogenase (quinone)

Word Map on EC 1.10.5.1
Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
Specify your search results
Select one or more organisms in this record:
Show additional data
Do not include text mining results
Include (text mining) results (more...)
Include results (AMENDA + additional results, but less precise; more...)

The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.10.5.1
-
RECOMMENDED NAME
GeneOntology No.
ribosyldihydronicotinamide dehydrogenase (quinone)
-
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
1-(beta-D-ribofuranosyl)-1,4-dihydronicotinamide + a quinone = 1-(beta-D-ribofuranosyl)nicotinamide + a quinol
show the reaction diagram
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
-
-
redox reaction
-
-
reduction
-
-
SYSTEMATIC NAME
IUBMB Comments
1-(beta-D-ribofuranosyl)-1,4-dihydronicotinamide:quinone oxidoreductase
A flavoprotein. Unlike EC 1.6.5.2, NAD(P)H dehydrogenase (quinone), this quinone reductase cannot use NADH or NADPH; instead it uses N-ribosyl- and N-alkyldihydronicotinamides. Polycyclic aromatic hydrocarbons, such as benz[a]anthracene, and the estrogens 17beta-estradiol and diethylstilbestrol are potent inhibitors, but dicoumarol is only a very weak inhibitor [2]. This enzyme can catalyse both 2-electron and 4-electron reductions, but one-electron acceptors, such as potassium ferricyanide, cannot be reduced [3].
CAS REGISTRY NUMBER
COMMENTARY hide
667919-86-0
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
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
1-(beta-D-ribofuranosyl)-1,4-dihydronicotinamide + a quinone
1-(beta-D-ribofuranosyl)nicotinamide + a hydroquinone
show the reaction diagram
-
-
-
-
?
1-(beta-D-ribofuranosyl)-1,4-dihydronicotinamide + co-enzyme Q
1-(beta-D-ribofuranosyl)nicotinamide + reduced co-enzyme Q
show the reaction diagram
-
natural substrate nicotinamide riboside, NRH
-
-
?
1-(beta-D-ribofuranosyl)-1,4-dihydronicotinamide + menadione
1-(beta-D-ribofuranosyl)nicotinamide + menadiol
show the reaction diagram
1-(carbamoylmethyl)dihydronicotinamide + 3-hydroxy-1-methylindoline-5,6-dione
1-(carbamoylmethyl)nicotinamide + 3-hydroxy-1-methylindoline-5,6-diol
show the reaction diagram
-
3-hydroxy-1-methylindoline-5,6-dione i.e. adrenochrome
-
-
?
1-carbamoylmethyl-3-carbamoyl-1,4-dihydropyrimidine + menadione
1-carbamoylmethyl-3-carbamoylpyrimidine + menadiol
show the reaction diagram
-
-
-
-
?
17beta-17-hydroxyestr-1(10)-ene-3,4-dione + N-benzyldihydronicotinamide
17beta-estra-1(10),2,4-triene-3,4,17-triol + N-benzylnicotinamide
show the reaction diagram
-
ping-pong mechanism, NQO2 is faster in reducing estrogen quinones than its homologue NQO1
-
-
?
2,6-dichloroindophenol + dihydronicotinamide riboside
? + nicotinamide riboside
show the reaction diagram
-
-
-
-
?
5-(aziridin-1-yl)-2,4-dinitrobenzamide + dihydronicotinamide riboside
? + nicotinamide riboside
show the reaction diagram
-
-
-
-
?
5-(aziridin-1-yl)-2,4-dinitrobenzamide + menadiol
? + reduced menadiol
show the reaction diagram
-
-
-
-
?
benzo(a)pyrene-3,6-quinone + dihydronicotinamide riboside
? + nicotinamide riboside
show the reaction diagram
-
-
-
-
?
dihydrobenzylnicotinamide + menadione
?
show the reaction diagram
-
-
-
-
?
dihydronicotinamide riboside + 2,6-dichlorophenolindophenol
nicotinamide riboside + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
-
-
-
-
?
dihydronicotinamide riboside + 3-(4,5-dimethylthiazaol-2-yl)-2,5-diphenyltetrazolium
nicotinamide riboside + ?
show the reaction diagram
-
-
-
-
?
dihydronicotinamide riboside + CB 1954
nicotinamide riboside + ?
show the reaction diagram
-
-
-
-
?
dihydronicotinamide riboside + menadione
ribosyl nicotinamide + menadiol
show the reaction diagram
-
-
-
-
?
dihydronicotinamide riboside + menadione/3-(4,5-dimethylthiazaol-2-yl)-2,5-diphenyltetrazolium
nicotinamide riboside + ?
show the reaction diagram
-
-
-
-
?
dihydronicotinamide riboside + methyl red
nicotinamide riboside + ?
show the reaction diagram
-
-
-
-
?
estrone-3,4-quinone + N-benzyldihydronicotinamide
estrone-3,4-quinol + N-benzylnicotinamide
show the reaction diagram
-
ping-pong mechanism, NQO2 is faster in reducing estrogen quinones than its homologue NQO1
-
-
?
menadione + 1-(2-hydroxyethyl)dihydronicotinamide
?
show the reaction diagram
-
-
-
?
menadione + dihydrobenzylnicotinamide
?
show the reaction diagram
menadione + dihydronicotinamide riboside
menadiol + nicotinamide riboside
show the reaction diagram
-
-
-
-
?
mitomycin C + dihydronicotinamide riboside
? + nicotinamide riboside
show the reaction diagram
-
-
-
-
?
N -benzyldihydronicotinamide + a quinone
N-benzylnicotinamide + a hydroquinone
show the reaction diagram
-
synthetic substrate
-
-
?
N-benzyldihydronicotinamide + 2,6-dichlorophenolindophenol
N-benzylnicotamide + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
-
-
-
-
?
N-benzyldihydronicotinamide + 2,6-dichlorophenolindophenol
N-benzylnicotinamide + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
-
-
-
-
?
N-benzyldihydronicotinamide + coenzyme Q0
?
show the reaction diagram
-
-
-
-
?
N-benzyldihydronicotinamide + coenzyme Q0
N-benzylnicotinamide + ?
show the reaction diagram
-
-
-
-
?
N-benzyldihydronicotinamide + coenzyme Q1
N-benzylnicotinamide + ?
show the reaction diagram
-
-
-
-
?
N-benzyldihydronicotinamide + menadione
?
show the reaction diagram
N-benzyldihydronicotinamide + menadione
N-benzylnicotamide + menadiol
show the reaction diagram
-
-
-
-
?
N-benzyldihydronicotinamide + menadione
N-benzylnicotinamide + menadiol
show the reaction diagram
-
-
-
-
?
N-benzyldihydronicotinamide + oxidized coenzyme Q0
N-benzylnicotinamide + reduced coenzyme Q20
show the reaction diagram
-
-
-
-
?
N-benzyldihydronicotinamide + oxidized coenzyme Q1
N-benzylnicointamide + reduced coenzyme Q1
show the reaction diagram
-
-
-
-
?
N-benzyldihydronicotinamide + oxidized coenzyme Q2
N-benzylnicotinamide + reduced coenzyme Q2
show the reaction diagram
-
-
-
-
?
N-benzylnicotinamide + menadiol
?
show the reaction diagram
-
-
-
-
?
N-methyldihydronicotinamide + 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide
N-methylnicotinamide + ?
show the reaction diagram
-
-
-
-
?
N-methyldihydronicotinamide + 3-hydroxy-1-methylindoline-5,6-dione
N-methylnicotinamide + 3-hydroxy-1-methylindoline-5,6-diol
show the reaction diagram
-
3-hydroxy-1-methylindoline-5,6-dione i.e. adrenochrome. When NADH is used as the electron donor, quinone reductase 2 possesses no activity for the reduction of adrenochrome
-
-
?
N-methyldihydronicotinamide + menadione
?
show the reaction diagram
N-methyldihydronicotinamide + menadione
N-methylnicotinamide + menadiol
show the reaction diagram
-
-
-
-
?
N-ribosylnicotinamide + menadiol
?
show the reaction diagram
-
N-ribosylnicotinamide is a poor substrate
-
-
?
nicotinamide riboside + menadiol
dihydronicotinamide riboside + menadione
show the reaction diagram
-
-
-
-
?
nicotinamide riboside + reduced 2,6-dichlorophenolindophenol
dihydronicotinamide riboside + 2,6-dichlorophenolindophenol
show the reaction diagram
-
-
-
-
?
nicotinamide riboside + reduced coenzyme Q0
dihydronicotinamide riboside + coenzyme Q0
show the reaction diagram
-
-
-
-
?
nicotinamide riboside + reduced coenzyme Q1
dihydronicotinamide riboside + coenzyme Q1
show the reaction diagram
-
-
-
-
?
nicotinamide riboside + reduced coenzyme Q2
dihydronicotinamide riboside + coenzyme Q2
show the reaction diagram
-
-
-
-
?
reduced N-methyldihydronicotinamide + menadione
? + menadiol
show the reaction diagram
-
-
-
-
?
reduced N1-(benzyl)-nicotinamide + menadione
N1-(benzyl)-nicotinamide + menadiol
show the reaction diagram
-
-
-
-
?
reduced N1-(methyl)-nicotinamide + menadione
N1-(methyl)-nicotinamide + reduced menadiol
show the reaction diagram
-
-
-
-
?
reduced N1-(n-propyl)-nicotinamide + menadione
N1-(n-propyl)-nicotinamide + menadiol
show the reaction diagram
-
-
-
-
?
tetrahydrofolate + menadiol
?
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
1-(beta-D-ribofuranosyl)-1,4-dihydronicotinamide + a quinone
1-(beta-D-ribofuranosyl)nicotinamide + a hydroquinone
show the reaction diagram
-
-
-
-
?
1-(beta-D-ribofuranosyl)-1,4-dihydronicotinamide + co-enzyme Q
1-(beta-D-ribofuranosyl)nicotinamide + reduced co-enzyme Q
show the reaction diagram
-
natural substrate nicotinamide riboside, NRH
-
-
?
1-(beta-D-ribofuranosyl)-1,4-dihydronicotinamide + menadione
1-(beta-D-ribofuranosyl)nicotinamide + menadiol
show the reaction diagram
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
FMN
-
the enzyme contains FAD as the sole bound flavin. The prosthetic group can be removed by treatment with acid in ammonium sulfate, and the resolved enzyme may be reactivated by FAD or by higher concentrations FMN
nicotinamide riboside
additional information
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Zn2+
-
-
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(E)-3-(3,5-dihydroxyphenyl)-2-(4-hydroxyphenyl)acrylaldehyde
-
-
(E)-3-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)prop-2-en-1-ol
-
-
(Z)-3-(3,5-dihydroxyphenyl)-2-(4-hydroxyphenyl)-acrylamide
-
-
(Z)-3-(3,5-dihydroxyphenyl)-2-(4-hydroxyphenyl)acrylonitrile
-
-
(Z)-3-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)acrylaldehyde
-
-
(Z)-3-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)acrylonitrile
-
-
(Z)-5-(3-hydroxy-2-(4-hydroxyphenyl)prop-1-en-1-yl)benzene-1,3-diol
-
-
1,1'-(1E)-but-1-ene-1,2-diylbis(3,5-dimethoxybenzene)
-
-
1,2-dimethoxy-4-[(1E)-2-(4-methoxyphenyl)prop-1-en-1-yl]benzene
-
-
1,2-dimethoxy-4-[(E)-2-(3-methoxyphenyl)ethenyl]benzene
-
-
1,2-dimethoxy-4-{(1Z)-3,3,3-trifluoro-2-[3-(trifluoromethyl)phenyl]prop-1-en-1-yl}benzene
-
-
1,3-dimethoxy-5-[(1E)-2-(4-methoxyphenyl)prop-1-en-1-yl]benzene
-
-
1,3-dimethoxy-5-[(1Z)-3,3,3-trifluoro-1-(4-methoxyphenyl)prop-1-en-2-yl]benzene
-
-
1,3-dimethoxy-5-[(E)-2-(4-methoxyphenyl)ethenyl]benzene
-
-
1,4-dimethylphenanthrene
-
0.00001 mM, 15% inhibition of the reaction with N1-(n-propyl)-nicotinamide
1,4-dimethylquinolin-2(1H)-one
-
-
1-[(E)-2-(4-fluorophenyl)ethenyl]-3,5-dimethoxybenzene
-
-
12-methylbenz[a]anthracene
-
0.00001 mM, 51% inhibition of the reaction with N1-(n-propyl)-nicotinamide
2-(2-methoxy-6H-pyrido[2',3':4,5]pyrrolo[2,1-a]isoindol-11-yl)ethylamine
-
IC50: 0.00087 mM
2-hydroxyestradiol
-
0.01 mM, 17% inhibition
2-iodo-5-methoxycarbonylamino-N-acetyltryptamine
-
-
2-iodo-melatonin
-
IC50: 0.016 mM
2-iodomelatonin
2-[(E)-2-(3,4-dimethoxyphenyl)ethenyl]naphthalene
-
-
2-[(E)-2-(3,5-dimethoxyphenyl)ethenyl]naphthalene
-
-
3-{[4-(dihydroxyamino)phenoxy]methyl}-5-methoxy-1,2-dimethyl-1H-indole-4,7-dione
-
-
4',5,7-trihydroxyflavone
-
0.01 mM, 61% inhibition
4-hydroxyestradiol
-
0.01 mM, 18% inhibition
4-hydroxyestrone
-
0.01 mM, 22% inhibition
4-[(1E)-1-(3,5-dimethoxyphenyl)prop-1-en-2-yl]-1,2-dimethoxybenzene
-
-
4-[(E)-2-(3,4-dimethoxyphenyl)ethenyl]-N,N-dimethylaniline
-
-
4-[(E)-2-(3,5-dimethoxyphenyl)ethenyl]-1,2-dimethoxybenzene
-
-
4-[(E)-2-(3,5-dimethoxyphenyl)ethenyl]phenol
-
-
4-[(E)-2-(3-fluorophenyl)ethenyl]benzene-1,2-diol
-
-
4-[(E)-2-(4-hydroxyphenyl)ethenyl]benzene-1,2-diol
-
-
4-[(E)-2-(4-methoxyphenyl)ethenyl]benzene-1,2-diol
-
-
4-{(1E)-1-[4-(trifluoromethyl)phenyl]prop-1-en-2-yl}phenol
-
-
4-{(E)-2-[3-(trifluoromethyl)phenyl]ethenyl}benzene-1,2-diol
-
-
5,6,8-trimethoxy-1,4-dimethylquinolin-2(1H)-one
-
-
5,6,8-trimethoxy-4-methylquinolin-2(1H)-one
-
-
5,8-dimethoxy-1,4-dimethylquinolin-2(1H)-one
-
-
5,8-dimethoxy-4-methylquinolin-2(1H)-one
-
-
5-(2-(dimethylamino)ethylamino)-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
-
-
-
5-(2-(dimethylamino)ethylamino)-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one N-oxide
-
-
-
5-(2-(dimethylamino)ethylamino)-8-bromo-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
-
-
-
5-(2-(dimethylamino)ethylamino)-8-bromo-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one N-oxide
-
-
-
5-(2-(dimethylamino)ethylamino)-8-fluoro-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
-
-
-
5-(2-(dimethylamino)ethylamino)-8-methoxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
-
-
5-(2-(dimethylamino)ethylamino)-8-methoxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one N-oxide
-
-
-
5-(3-hydroxypropylamino)-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
-
-
-
5-(3-hydroxypropylamino)-8-bromo-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
-
-
-
5-(3-hydroxypropylamino)-8-methoxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
-
-
-
5-(4-methoxyphenylamino)-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
-
-
-
5-(isopentylamino)-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
-
-
-
5-(phenethylamino)-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
-
-
-
5-amino-1,2-dimethyl-3-[(2,4,6-trifluorophenoxy)methyl]-1H-indole-4,7-dione
-
-
5-hydroxyflavone
-
IC50: 340 nM
5-hydroxytryptamine
-
-
5-methoxy-carbonylamino-N-acetyltryptamine
-
IC50: 0.295 mM
5-methoxycarbonylamino-N-acetyltryptamine
5-[(1E)-1-(4-hydroxyphenyl)prop-1-en-2-yl]benzene-1,3-diol
-
-
5-[(1E)-2-(3,4-dimethoxyphenyl)prop-1-en-1-yl]benzene-1,3-diol
-
-
5-[(1E)-2-(4-hydroxyphenyl)prop-1-en-1-yl]benzene-1,3-diol
-
-
5-[(1E)-2-(4-methoxyphenyl)prop-1-en-1-yl]benzene-1,3-diol
-
-
5-[(4-aminobutyl)amino]-1,2-dimethyl-3-[(2,4,6-trifluorophenoxy)methyl]-1H-indole-4,7-dione
-
-
5-[(4-aminobutyl)amino]-1,2-dimethyl-3-[(4-nitrophenoxy)methyl]-1H-indole-4,7-dione
-
-
5-[(8-aminooctyl)amino]-1,2-dimethyl-3-[(2,4,6-trifluorophenoxy)methyl]-1H-indole-4,7-dione
-
-
5-[butyl(methyl)amino]-1,2-dimethyl-3-[(2,4,6-trifluorophenoxy)methyl]-1H-indole-4,7-dione
-
-
5-[[4-(diethylamino)butyl]amino]-10-methoxy-6H-imidazo[4,5,1-de]acridin-6-one
-
-
5-[[4-(diethylamino)butyl]amino]-6H-imidazo[4,5,1-de]acridin-6-one
-
-
5-[[4-(diethylamino)butyl]amino]-7,10-dimethoxy-6H-imidazo[4,5,1-de]acridin-6-one
-
-
5-[[4-(diethylamino)butyl]amino]-7-hydroxy-10-methoxy-6H-imidazo[4,5,1-de]acridin-6-one
-
-
5-[[4-(diethylamino)butyl]amino]-7-hydroxy-8,9-dimethoxy-6H-imidazo[4,5,1-de]acridin-6-one
-
most potent inhibitor of NQO2
5-[[4-(diethylamino)butyl]amino]-8-hydroxy-1-methyl-6H-imidazo[4,5,1-de]acridin-6-one
-
-
5-[[4-(diethylamino)butyl]amino]-8-hydroxy-6H-imidazo[4,5,1-de]acridin-6-one
-
-
5-[[4-(diethylamino)butyl]amino]-8-methoxy-1-methyl-6H-imidazo[4,5,1-de]acridin-6-one
-
-
5-[[4-(diethylamino)butyl]amino]-8-methoxy-6H-imidazo[4,5,1-de]acridin-6-one
-
-
5-[[4-(diethylamino)butyl]amino]-9-hydroxy-6H-imidazo[4,5,1-de]acridin-6-one
-
-
5-[[4-(dimethylamino)butyl]amino]-1-ethyl-6H-imidazo[4,5,1-de]acridin-6-one
-
-
5-[[4-(dimethylamino)butyl]amino]-1-methyl-6H-imidazo[4,5,1-de]acridin-6-one
-
-
5-[[4-(dimethylamino)butyl]amino]-6H-imidazo[4,5,1-de]acridin-6-one
-
-
5-[[4-(dimethylamino)butyl]amino]-8-hydroxy-1-methyl-6H-imidazo[4,5,1-de]acridin-6-one
-
-
5-[[4-(dimethylamino)butyl]amino]-8-hydroxy-6H-imidazo[4,5,1-de]acridin-6-one
-
-
5-[[6-(diethylamino)hexyl]amino]-8-hydroxy-6H-imidazo[4,5,1-de]acridin-6-one
-
-
5-[[6-(dimethylamino)hexyl]amino]-6H-imidazo[4,5,1-de]acridin-6-one
-
-
5-{(1E)-1-[4-(dimethylamino)phenyl]but-1-en-2-yl}benzene-1,3-diol
-
-
5-{[2-(dimethylamino)ethyl]amino}-1,2-dimethyl-3-(phenoxymethyl)-1H-indole-4,7-dione
-
-
5-{[2-(dimethylamino)ethyl]amino}-1,2-dimethyl-3-[(2,4,6-trifluorophenoxy)methyl]-1H-indole-4,7-dione
-
-
5-{[2-(dimethylamino)ethyl]amino}-1-methyl-2-phenyl-3-[(2,4,6-trifluorophenoxy)methyl]-1H-indole-4,7-dione
-
-
5-{[2-(dimethylamino)ethyl]amino}-1-methyl-3-[(2,4,6-trifluorophenoxy)methyl]-1H-indole-4,7-dione
-
-
5-{[3-(dimethylamino)propyl]amino}-1,2-dimethyl-3-[(2,4,6-trifluorophenoxy)methyl]-1H-indole-4,7-dione
-
-
6,7,8-trimethoxy-1,4-dimethylquinolin-2(1H)-one
-
-
6,7,8-trimethoxy-4-methylquinolin-2(1H)-one
-
-
6,8-dimethoxy-1,4-dimethylquinolin-2(1H)-one
-
-
6,8-dimethoxy-4-methylquinolin-2(1H)-one
-
-
6,9-dimethyl-[1,3]dioxolo[4,5-h]quinolin-8(9H)-one
-
-
6-methoxy-9-methyl-[1,3]dioxolo[4,5-h]quinolin-8(9H)-one
-
-
6-methyl-[1,3]dioxolo[4,5-h]quinolin-8(9H)-one
-
-
7,12-dimethylbenz[a]anthracene
-
0.00001 mM, 51% inhibition of the reaction with N1-(n-propyl)-nicotinamide
7,8-dihydroxyflavone
-
0.01 mM, 7% inhibition
7,8-dimethoxy-1,4-dimethylquinolin-2(1H)-one
-
-
7,8-dimethoxy-4-methylquinolin-2(1H)-one
-
-
7-methylbenz[a]anthracene
-
0.00001 mM, 66% inhibition of the reaction with N1-(n-propyl)-nicotinamide
8-bromo-5-[(3-methylbutyl)amino]-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
-
-
8-methoxy-1,4-dimethylquinolin-2(1H)-one
-
-
8-methoxy-4-methylquinolin-2(1H)-one
-
-
8-methoxy-5-(phenethylamino)-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
-
-
-
9,10-dimethylanthracene
-
0.00001 mM, 25% inhibition of the reaction with N1-(n-propyl)-nicotinamide
9-methylanthracene
-
0.00001 mM, 26% inhibition of the reaction with N1-(n-propyl)-nicotinamide
alpha-naphthoflavone
-
0.01 mM, 75% inhibition
apigenin
-
IC50: 430 nM
benzo(a)pyrene
benzo[a]pyrene
-
0.0001 mM, 75% inhibition
benz[a]anthracene
-
0.00001 mM, 40% inhibition of the reaction with N1-(n-propyl)-nicotinamide
beta-naphthoflavone
-
0.01 mM, 76% inhibition
Chloroquine
chrysin
-
0.01 mM, complete inhibition
chrysin-dimethylether
-
IC50: 0.0013 mM
chrysoeriol
dabigatran
-
; specific binding to the enzyme, protein interaction analysis, overview
dabigatran ethyl ester
-
-
dicoumarol
estradiol
-
0.01 mM, 13% inhibition
ethyl 3-(2-((4-(N-(4-(tert-butoxycarbonylamino)butyl)-carbamimidoyl)phenylamino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido)propanoate
-
-
ethyl N-[(2-{[(4-carbamimidoylphenyl)amino]methyl}-1H-benzimidazol-5-yl)carbonyl]-N-pyridin-2-yl-b-alaninate
-
-
flavone
-
0.01 mM, 14% inhibition
galangin
-
0.01 mM, complete inhibition
genistein
-
-
imatinib
isorhamnetin
-
IC50: 860 nM
kaempferol
-
IC50: 380 nM
luteolin
-
IC50: 780 nM
mefloquine
-
-
melagatran
-
-
Melatonin
methyl 2-((S)-1-cyclohexyl-2-((R)-2-(4-(4-(4-nitrophenylsulfonamido)butylcarbamoyl)benzylcarbamoyl)-azetidin-1-yl)-2-oxoethylamino)acetate
-
-
methyl N-{(1R)-1-cyclohexyl-2-oxo-2-[(2S)-2-{[4-({4-[(N-{17-oxo-21-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]-4,8,12-trioxa-16-azahenicos-1-yl}-N2-{4-[3-(trifluoromethyl)-3H-diaziren-3-yl]benzoyl}-L-alpha-asparaginyl)amino]butyl}carbamoyl)benzyl]carbamoyl}azetidin-1-yl]ethyl}glycinate
-
-
methyl-1-(2-acetamidoethyl)-7-naphthylcarbamate
-
IC50: 0.015 mM
morin
-
0.01 mM, 95% inhibition
N-(3,5-dihydroxyphenyl)-4-hydroxybenzamide
-
-
N-acetyl-5-hydroxytryptamine
-
-
N-acetylserotonin
N-[2-(2-iodo-5-methoxy-1-methyl-4-nitroindol-3-yl)ethyl]acetamide
-
inhibits enzymatic mechanism of the enzyme through the MT3 binding site, IC50: 0.0003 mM
N-[2-(2-methoxy-6H-dipyrido[2,3-a:3,2-e]pyrrolizin-11-yl)ethyl]-2-furamide
-
IC50: 14 nM
N-[2-(2-methoxy-6H-pyrido[2',3':4,5]pyrrolo[2,1-a]isoindol-11-yl)ethyl]2-furamide
-
IC50: 0.0002 mM
N-[2-(5-methoxy-4-nitro-1H-indol-3-yl)ethyl]acetamide
-
IC50: 0.0015 mM
N-[2-(5-methoxy-7-nitro-1H-indol-3-yl)ethyl]acetamide
-
IC50: 0.044 mM
N-[2-(7-methylaminosulfonyl-1-naphthyl)ethyl]acetamide
-
IC50: 0.038 mM
N-[2-(8-methoxy-3,4-dihydro-2H-pyrido[2',3':4,5]pyrrolo[2,1-b][1,3]oxazin-10-yl)ethyl]-2-furamide
-
IC50: 0.005 mM
N-{(1R)-1-cyclohexyl-2-oxo-2-[(2S)-2-{[4-({4-[(N-{17-oxo-21-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]-4,8,12-trioxa-16-azahenicos-1-yl}-N2-{4-[3-(trifluoromethyl)-3H-diaziren-3-yl]benzoyl}-L-alpha-asparaginyl)amino]butyl}carbamoyl)benzyl]carbamoyl}azetidin-1-yl]ethyl}glycine
-
-
N-{[1-methyl-2-({[4-(N-{3-[(N-{17-oxo-21-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]-4,8,12-trioxa-16-azahenicos-1-yl}-N2-{4-[3-(trifluoromethyl)-3H-diaziren-3-yl]benzoyl}-L-alpha-asparaginyl)amino]propyl}carbamimidoyl)phenyl]amino}methyl)-1H-benzimidazol-5-yl]carbonyl}-N-pyridin-2-yl-beta-alanine
-
-
N1-[2-(2-methoxy-6H-pyrido[2',3':4,5]pyrrolo[2,1-a]isoindol-11-yl)ethyl]-acetamide
-
IC50: 0.0019 mM
N4-[2-(4-{4-[(4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}phenyl)carbamoyl]benzyl}piperazin-1-yl)ethyl]-N1-{17-oxo-21-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]-4,8,12-trioxa-16-azahenicos-1-yl}-N2-{4-[3-(trifluoromethyl)-3H-diaziren-3-yl]benzoyl}-L-aspartamide
-
-
N4-[3-({N-[(2-{[(4-carbamimidoylphenyl)amino]methyl}-1-methyl-1H-benzimidazol-5-yl)carbonyl]-N-phenyl-b-alanyl}amino)propyl]-N1-{17-oxo-21-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]-4,8,12-trioxa-16-azahenicos-1-yl}-N2-{4-[3-(trifluoromethyl)-3H-diaziren-3-yl]benzoyl}-L-aspartamide
-
-
N4-[4-({N-[(1R)-2-{(2R)-2-[(4-carbamimidoylbenzyl)carbamoyl]cyclobutyl}-1-cyclohexylprop-2-en-1-yl]glycyl}amino)butyl]-N1-{17-oxo-21-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]-4,8,12-trioxa-16-azahenicos-1-yl}-N2-{4-[3-(trifluoromethyl)-3H-diaziren-3-yl]benzoyl}-L-aspartamide
-
-
NSC106080
-
i.e. bis(2-hydroxyphenyl)methanone phenylhydrazone
-
NSC115890
-
i.e. 1,3-naphthalenediol
-
NSC180969
-
i.e. 7,8-dimethoxy-4-(3,4,5-trimethoxyphenyl)-1,2-dihydro-3H-benzo[e]isoindol-3-one
-
NSC187208
-
i.e. N4-(7-chloro-4-quinolinyl)-N1,N1-diethyl-1,4-pentanediamine, chloroquine
-
NSC204996
-
i.e. 7,8-dimethoxy-4-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1H-benzo[e]isoindole
-
NSC238146
-
i.e. N4-(6-((6-amino-2-methyl-4-quinolinyl)amino)hexyl)-2-methyl-4,6-quinolinediamine acetate
-
NSC27296
-
i.e. N4-(6-methoxy-8-quinolinyl)-1,4-pentanediamine, primaquine
-
NSC300853
-
i.e. 3-amino-9-ethyl-2-((4-(hydroxy(oxido)amino)phenyl)diazenyl)-9H-carbazole
-
NSC306843
-
i.e. 1-methyl-4(1H)-quinolinone (1-methyl-4(1H)-quinolinylidene)hydrazone
-
NSC332172
-
i.e. 2-(4-methoxyphenyl)-3-(3,4,5-trimethoxyphenyl)acrylonitrile
-
NSC356819
-
i.e. 4-((2-hydroxy-5-(phenyldiazenyl)phenyl)diazenyl)benzenecarboximidamide
-
NSC356820
-
i.e. 4-((2-hydroxy-5-(2-phenylvinyl)phenyl)diazenyl)benzenecarboximidamide
-
NSC359466
-
i.e. 4-((4-(amino(imino)methyl)phenyl)diazenyl)-3-hydroxy-N-phenyl-2-naphthamide
-
NSC381864
-
i.e. 5-(2-(3,5-dimethoxyphenyl)vinyl)-2-methoxyphenol
-
NSC621351
-
i.e. 2-(2-fluorophenyl)-4-(2-naphthyl)-2,3-dihydro-1,5-benzothiazepine
-
NSC623234
-
i.e. 3-chloro-3-(3,4-dimethoxyphenyl)-2-(3,4,5-trimethoxyphenyl)acrylaldehyde
-
NSC637991
-
-
NSC637992
-
-
NSC637993
-
-
NSC637994
-
-
NSC640353
-
i.e. 1-(2-(3,5-diphenyl-1H-pyrazol-1-yl)-4-methyl-1,3-thiazol-5-yl)-4-methyl-5-phenyl-2,4-pentadien-1-one
-
NSC640556
-
i.e. 1-(2-(3,5-diphenyl-1H-pyrazol-1-yl)-4-methyl-1,3-thiazol-5-yl)-3-(4-(hydroxy(oxido)amino)phenyl)-2-propen-1-one
-
NSC640558
-
i.e 1-(2-(3,5-diphenyl-1H-pyrazol-1-yl)-4-methyl-1,3-thiazol-5-yl)-3-phenyl-2-propen-1-one
-
NSC640559
-
i.e. 1-(2-(3,5-diphenyl-1H-pyrazol-1-yl)-4-methyl-1,3-thiazol-5-yl)-3-(3-(hydroxy(oxido)amino)phenyl)-2-propen-1-one
-
NSC640566
-
i.e. 3-(4-chlorophenyl)-1-(2-(3,5-diphenyl-1H-pyrazol-1-yl)-4-methyl-1,3-thiazol-5-yl)-2-propen-1-one
-
NSC640583
-
i.e. 1-(2-(3,5-diphenyl-1H-pyrazol-1-yl)-4-methyl-1,3-thiazol-5-yl)-3-(4-methylphenyl)-2-propen-1-one
-
NSC640584
-
i.e. 3-(3,4-dichlorophenyl)-1-(2-(3,5-diphenyl-1H-pyrazol-1-yl)-4-methyl-1,3-thiazol-5-yl)-2-propen-1-one
-
NSC645808
-
-
NSC645809
-
-
NSC645811
-
-
NSC645812
-
-
NSC645831
-
-
NSC645833
-
-
NSC645834
-
-
NSC645835
-
-
NSC645836
-
-
NSC648420
-
i.e. 1,2,3-trimethoxyphenanthro[2,3-d][1,3]dioxol-6-yl acetate
-
NSC648422
-
i.e. 5-(1-methyl-2-(3,4,5-trimethoxyphenyl)vinyl)-1,3-benzodioxole
-
NSC649091
-
i.e. 2-((diethylamino)methyl)-4-((10-methyl-10H-indolo[3,2-b]quinolin-11-yl)amino)phenol hydrochloride
-
NSC65069
-
i.e. [1,1'-biphenyl]-2,3',4,5',6-pentol
-
NSC660838
-
-
-
NSC660839
-
-
NSC660840
-
-
NSC660841
NSC66167
-
i.e. [1,1'-biphenyl]-2,2',4,4'-tetrol
-
NSC665126
-
i.e. 1-(2-(4-(hydroxy(oxido)amino)phenyl)vinyl)-3-phenylbenzo[f]quinoline
-
NSC669977
-
i.e. 6-imino-1-methyl-3-phenyl-2,6-dihydro-5(1H)-quinolinone hydrazone
-
NSC676468
-
i.e. N-(3-([1,10-biphenyl]-4-ylimino)-1-propenyl)[1,10-biphenyl]-4-amine
-
NSC677939
-
i.e. 14H-diindolo[2,3-a:3,2-h]quinolizine
-
NSC693571
-
i.e. trifluoromethanesulfonic acid compound with N,N-dimethyl-4-((1-methyl-2-phenyl-4H-1lambda5-pyrazolo[1,5-a]indol-4-ylidene)methyl)aniline
-
NSC720622
-
i.e. trifluoromethanesulfonic acid compound with N,N-dimethyl-4-((1-methyl-6-nitro-2-phenylpyrazolo[1,5-a]indol-1-ium-4-ylidene)methyl)aniline
-
NSC77833
-
i.e. 1-(2-(1H-indol-3-yl)vinyl)isoquinoline
-
NSC78017
-
i.e. 2,6-dimethyl-3H-pyrrolo[3,2-f]quinoline
-
NSC78021
-
i.e. 4,7-dimethyl-7H-pyrido[2,3-c]carbazole
-
NSC86715
-
i.e. 5-methyl-1-phenyl-6H-pyrido[4,3-b]carbazole
-
NSC97374
-
i.e. 1-ethyl-2-((1-ethyl-2(1H)-quinolinylidene)methyl)-1lambda5-quinoline
-
NSC99495
-
i.e. 3-benzo[a]anthracen-12-ylthiophene
-
NSC99528
-
i.e. 2-benzo[a]anthracen-12-yl-1-benzothiophene
-
primaquine
quercetin
quercetin-3-O-beta-glucopyranosyl
-
IC50: 0.0015 mM
Quinacrine
-
-
Quinine
-
-
resveratrol
S26553
S26695
S28128
-
IC50: 0.00091 mM
S29434
serotonin
-
-
tert-butyl 4-(4-(4-nitrophenylsulfonamido)butylcarbamoyl)-benzylcarbamate
-
-
tert-butyl(S)-1-cyclohexyl -2-((R)-2-(4-(4-(4-nitrophenylsulfonamido)butylcarbamoyl)benzylcarbamoyl)-azetidin-1-yl)-2-oxoethylcarbamate
-
-
-
additional information
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00075
17beta-17-hydroxyestr-1(10)-ene-3,4-dione
-
-
0.007 - 0.019
2,6-dichlorophenolindophenol
0.012
3-(4,5-dimethylthiazaol-2-yl)-2,5-diphenyltetrazolium
-
-
0.061
5-(aziridin-1-yl)-2,4-dinitrobenzamide
-
at 25C in pH 8.5 buffer (50 mM Tris, 140 mM NaCl, and 0.1% Tween 20) with 0.1 mM menadione as co-substrate
0.26
CB 1954
-
-
0.0137
coenzyme Q0
-
using N-benzyl dihydronicotinamide as cosubstrate, at 25C, in 50 mM Tris-HCl, pH 8.5
0.0517
coenzyme Q1
-
using N-benzyl dihydronicotinamide as cosubstrate, at 25C, in 50 mM Tris-HCl, pH 8.5
0.0387
coenzyme Q2
-
using N-benzyl dihydronicotinamide as cosubstrate, at 25C, in 50 mM Tris-HCl, pH 8.5
0.02 - 0.0608
dihydrobenzylnicotinamide
0.028
dihydronicotinamide riboside
-
-
0.000033
estradiol-3,4-quinone
-
-
0.0016 - 0.0252
menadione
0.0023
menadione/3-(4,5-dimethylthiazaol-2-yl)-2,5-diphenyltetrazolium
-
-
0.0047
Methyl red
-
-
0.0113 - 0.0602
N-benzyl dihydronicotinamide
0.02
N-benzyldihydronicotinamide
-
-
0.252
NADH
-
-
0.023
reduced N1-(n-propyl)-nicotinamide
-
pH 7.6
2
tetrahydrofolate
-
-
additional information
additional information
-
steady-state kinetic, overview
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
46.67 - 91.8
2,6-dichlorophenolindophenol
11
3-(4,5-dimethylthiazaol-2-yl)-2,5-diphenyltetrazolium
Homo sapiens
-
-
6
5-(aziridin-1-yl)-2,4-dinitrobenzamide
43.33
dihydronicotinamide riboside
Homo sapiens
-
-
38.33
menadione/3-(4,5-dimethylthiazaol-2-yl)-2,5-diphenyltetrazolium
Homo sapiens
-
-
3.83
Methyl red
Homo sapiens
-
-
2.6
NADH
Homo sapiens
-
-
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.012 - 0.033
2-iodo-5-methoxycarbonylamino-N-acetyltryptamine
0.004 - 0.05
2-iodo-melatonin
0.0012 - 0.029
2-iodomelatonin
0.0435 - 0.376
5-methoxycarbonylamino-N-acetyltryptamine
0.00061
Chloroquine
-
-
0.07
dabigatran
-
pH and temperature not specified in the publication
0.0009
dabigatran ethyl ester
-
pH and temperature not specified in the publication
0.566 - 0.62
dicoumarol
0.017
mefloquine
-
-
0.0072 - 0.246
Melatonin
0.092 - 0.204
N-acetylserotonin
0.00008 - 0.00031
N-[2-(2-iodo-5-methoxy-1-methyl-4-nitroindol-3-yl)ethyl]acetamide
0.00003 - 0.00004
N-[2-(2-methoxy-6H-dipyrido[2,3-a:3,2-e]pyrrolizin-11-yl)ethyl]-2-furamide
0.00104
primaquine
-
-
0.000021
quercetin
-
-
0.00051
Quinacrine
-
-
0.252
Quinine
-
-
0.00005 - 0.000088
resveratrol
0.0028 - 0.0414
S26553
0.00018 - 0.0009
S28128
2.933
serotonin
-
-
additional information
additional information
-
Michaelis-Menten inhibition kinetics
-
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0182
1,4-dimethylquinolin-2(1H)-one
Homo sapiens
-
23C
0.00087
2-(2-methoxy-6H-pyrido[2',3':4,5]pyrrolo[2,1-a]isoindol-11-yl)ethylamine
Homo sapiens
-
IC50: 0.00087 mM
0.016
2-iodo-melatonin
Homo sapiens
-
IC50: 0.016 mM
0.0011
2-iodomelatonin
Homo sapiens
-
pH 8, 25C
0.0108
5,6,8-trimethoxy-1,4-dimethylquinolin-2(1H)-one
Homo sapiens
-
23C
0.006
5,6,8-trimethoxy-4-methylquinolin-2(1H)-one
Homo sapiens
-
23C
0.0041
5,8-dimethoxy-1,4-dimethylquinolin-2(1H)-one
Homo sapiens
-
23C
0.0108
5,8-dimethoxy-4-methylquinolin-2(1H)-one
Homo sapiens
-
23C
0.001833
5-(2-(dimethylamino)ethylamino)-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.000167
5-(2-(dimethylamino)ethylamino)-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one N-oxide
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.001483
5-(2-(dimethylamino)ethylamino)-8-bromo-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.000117
5-(2-(dimethylamino)ethylamino)-8-bromo-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one N-oxide
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.000783
5-(2-(dimethylamino)ethylamino)-8-fluoro-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.001333
5-(2-(dimethylamino)ethylamino)-8-methoxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
0.000098
5-(2-(dimethylamino)ethylamino)-8-methoxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one N-oxide
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.000483
5-(3-hydroxypropylamino)-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.000987
5-(3-hydroxypropylamino)-8-bromo-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.000517
5-(3-hydroxypropylamino)-8-methoxy-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.000098
5-(4-methoxyphenylamino)-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.000427
5-(isopentylamino)-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.000567
5-(phenethylamino)-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.00034
5-hydroxyflavone
Homo sapiens
-
IC50: 340 nM
0.0539
5-hydroxytryptamine
Homo sapiens
-
pH 8, 25C
0.295
5-methoxy-carbonylamino-N-acetyltryptamine
Homo sapiens
-
IC50: 0.295 mM
0.000099
5-[[4-(diethylamino)butyl]amino]-10-methoxy-6H-imidazo[4,5,1-de]acridin-6-one
Homo sapiens
-
pH and temperature not specified in the publication
0.000427
5-[[4-(diethylamino)butyl]amino]-6H-imidazo[4,5,1-de]acridin-6-one
Homo sapiens
-
pH and temperature not specified in the publication
0.000017
5-[[4-(diethylamino)butyl]amino]-7,10-dimethoxy-6H-imidazo[4,5,1-de]acridin-6-one
Homo sapiens
-
pH and temperature not specified in the publication
0.000031
5-[[4-(diethylamino)butyl]amino]-7-hydroxy-10-methoxy-6H-imidazo[4,5,1-de]acridin-6-one
Homo sapiens
-
pH and temperature not specified in the publication
0.000006
5-[[4-(diethylamino)butyl]amino]-7-hydroxy-8,9-dimethoxy-6H-imidazo[4,5,1-de]acridin-6-one
Homo sapiens
-
pH and temperature not specified in the publication
0.000016
5-[[4-(diethylamino)butyl]amino]-8-hydroxy-1-methyl-6H-imidazo[4,5,1-de]acridin-6-one
Homo sapiens
-
pH and temperature not specified in the publication
0.000148
5-[[4-(diethylamino)butyl]amino]-8-hydroxy-6H-imidazo[4,5,1-de]acridin-6-one
Homo sapiens
-
pH and temperature not specified in the publication
0.000009
5-[[4-(diethylamino)butyl]amino]-8-methoxy-1-methyl-6H-imidazo[4,5,1-de]acridin-6-one
Homo sapiens
-
pH and temperature not specified in the publication
0.001
5-[[4-(diethylamino)butyl]amino]-8-methoxy-6H-imidazo[4,5,1-de]acridin-6-one
Homo sapiens
-
pH and temperature not specified in the publication
0.000953
5-[[4-(diethylamino)butyl]amino]-9-hydroxy-6H-imidazo[4,5,1-de]acridin-6-one
Homo sapiens
-
pH and temperature not specified in the publication
0.000693
5-[[4-(dimethylamino)butyl]amino]-1-ethyl-6H-imidazo[4,5,1-de]acridin-6-one
Homo sapiens
-
pH and temperature not specified in the publication
0.000323
5-[[4-(dimethylamino)butyl]amino]-1-methyl-6H-imidazo[4,5,1-de]acridin-6-one
Homo sapiens
-
pH and temperature not specified in the publication
0.00083
5-[[4-(dimethylamino)butyl]amino]-6H-imidazo[4,5,1-de]acridin-6-one
Homo sapiens
-
pH and temperature not specified in the publication
0.00005
5-[[4-(dimethylamino)butyl]amino]-8-hydroxy-1-methyl-6H-imidazo[4,5,1-de]acridin-6-one
Homo sapiens
-
pH and temperature not specified in the publication
0.000296
5-[[4-(dimethylamino)butyl]amino]-8-hydroxy-6H-imidazo[4,5,1-de]acridin-6-one
Homo sapiens
-
pH and temperature not specified in the publication
0.000597
5-[[6-(diethylamino)hexyl]amino]-8-hydroxy-6H-imidazo[4,5,1-de]acridin-6-one
Homo sapiens
-
pH and temperature not specified in the publication
0.000172
5-[[6-(dimethylamino)hexyl]amino]-6H-imidazo[4,5,1-de]acridin-6-one
Homo sapiens
-
pH and temperature not specified in the publication
0.007
6,7,8-trimethoxy-1,4-dimethylquinolin-2(1H)-one
Homo sapiens
-
23C
0.01
6,7,8-trimethoxy-4-methylquinolin-2(1H)-one
Homo sapiens
-
23C
0.0019
6,8-dimethoxy-1,4-dimethylquinolin-2(1H)-one
Homo sapiens
-
23C
0.0088
6,8-dimethoxy-4-methylquinolin-2(1H)-one
Homo sapiens
-
23C
0.0062
6,9-dimethyl-[1,3]dioxolo[4,5-h]quinolin-8(9H)-one
Homo sapiens
-
23C
0.0541
6-methoxy-9-methyl-[1,3]dioxolo[4,5-h]quinolin-8(9H)-one
Homo sapiens
-
23C
0.0108
6-methyl-[1,3]dioxolo[4,5-h]quinolin-8(9H)-one
Homo sapiens
-
23C
0.0093
7,8-dimethoxy-1,4-dimethylquinolin-2(1H)-one
Homo sapiens
-
23C
0.0293
7,8-dimethoxy-4-methylquinolin-2(1H)-one
Homo sapiens
-
23C
0.000767
8-bromo-5-[(3-methylbutyl)amino]-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
0.0058
8-methoxy-1,4-dimethylquinolin-2(1H)-one
Homo sapiens
-
23C
0.0241
8-methoxy-4-methylquinolin-2(1H)-one
Homo sapiens
-
23C
0.00035
8-methoxy-5-(phenethylamino)-6H-[1,2,3]triazolo[4,5,1-de]acridin-6-one
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.00043
apigenin
Homo sapiens
-
IC50: 430 nM
0.0013
chrysin-dimethylether
Homo sapiens
-
IC50: 0.0013 mM
0.000016 - 0.00082
chrysoeriol
0.06
dabigatran
Homo sapiens
-
pH and temperature not specified in the publication
0.0008
dabigatran ethyl ester
Homo sapiens
-
pH and temperature not specified in the publication
0.59
dicoumarol
Homo sapiens
-
IC50: 0.59 mM
0.00086
isorhamnetin
Homo sapiens
-
IC50: 860 nM
0.00038
kaempferol
Homo sapiens
-
IC50: 380 nM
0.00078
luteolin
Homo sapiens
-
IC50: 780 nM
0.0028 - 0.13
Melatonin
0.015
methyl-1-(2-acetamidoethyl)-7-naphthylcarbamate
Homo sapiens
-
IC50: 0.015 mM
0.0099
N-acetyl-5-hydroxytryptamine
Homo sapiens
-
pH 8, 25C
0.099
N-acetylserotonin
Homo sapiens
-
IC50: 0.099 mM
0.0003
N-[2-(2-iodo-5-methoxy-1-methyl-4-nitroindol-3-yl)ethyl]acetamide
Homo sapiens
-
inhibits enzymatic mechanism of the enzyme through the MT3 binding site, IC50: 0.0003 mM
0.000014
N-[2-(2-methoxy-6H-dipyrido[2,3-a:3,2-e]pyrrolizin-11-yl)ethyl]-2-furamide
Homo sapiens
-
IC50: 14 nM
0.0002
N-[2-(2-methoxy-6H-pyrido[2',3':4,5]pyrrolo[2,1-a]isoindol-11-yl)ethyl]2-furamide
Homo sapiens
-
IC50: 0.0002 mM
0.0015
N-[2-(5-methoxy-4-nitro-1H-indol-3-yl)ethyl]acetamide
Homo sapiens
-
IC50: 0.0015 mM
0.044
N-[2-(5-methoxy-7-nitro-1H-indol-3-yl)ethyl]acetamide
Homo sapiens
-
IC50: 0.044 mM
0.038
N-[2-(7-methylaminosulfonyl-1-naphthyl)ethyl]acetamide
Homo sapiens
-
IC50: 0.038 mM
0.005
N-[2-(8-methoxy-3,4-dihydro-2H-pyrido[2',3':4,5]pyrrolo[2,1-b][1,3]oxazin-10-yl)ethyl]-2-furamide
Homo sapiens
-
IC50: 0.005 mM
0.0019
N1-[2-(2-methoxy-6H-pyrido[2',3':4,5]pyrrolo[2,1-a]isoindol-11-yl)ethyl]-acetamide
Homo sapiens
-
IC50: 0.0019 mM
0.0039
NSC106080
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.0033
NSC115890
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.002
NSC180969
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.0015
NSC187208
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.0027
NSC204996
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.0019
NSC238146
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.0075
NSC27296
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.005
NSC300853
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.0062
NSC306843
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.02
NSC332172
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.0018
NSC356819
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.0014
NSC356820
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.006
NSC359466
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.015
NSC381864
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.022
NSC623234
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.00005
NSC637991
Homo sapiens
-
pH and temperature not specified in the publication
0.000016
NSC637992
Homo sapiens
-
pH and temperature not specified in the publication
0.000009
NSC637993
Homo sapiens
-
pH and temperature not specified in the publication
0.000597
NSC637994
Homo sapiens
-
pH and temperature not specified in the publication
0.0038
NSC640353
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.006
NSC640556
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.0058
NSC640558
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.0065
NSC640559
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.0053
NSC640566
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.0032
NSC640583
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.0049
NSC640584
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.000296
NSC645808
Homo sapiens
-
pH and temperature not specified in the publication
0.000148
NSC645809
Homo sapiens
-
pH and temperature not specified in the publication
0.000953
NSC645811
Homo sapiens
-
pH and temperature not specified in the publication
0.001
NSC645812
Homo sapiens
-
pH and temperature not specified in the publication
0.000427
NSC645831
Homo sapiens
-
pH and temperature not specified in the publication
0.00083
NSC645833
Homo sapiens
-
pH and temperature not specified in the publication
0.000323
NSC645834
Homo sapiens
-
pH and temperature not specified in the publication
0.000693
NSC645835
Homo sapiens
-
pH and temperature not specified in the publication
0.000172
NSC645836
Homo sapiens
-
pH and temperature not specified in the publication
0.0035
NSC649091
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.000099
NSC660838
Homo sapiens
-
pH and temperature not specified in the publication
-
0.000017
NSC660839
Homo sapiens
-
pH and temperature not specified in the publication
0.000031
NSC660840
Homo sapiens
-
pH and temperature not specified in the publication
0.000006
NSC660841
Homo sapiens
-
pH and temperature not specified in the publication
0.0058
NSC66167
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.0096
NSC665126
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.002
NSC669977
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.0097
NSC676468
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.0029
NSC677939
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.0017
NSC693571
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.005
NSC720622
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.0018
NSC77833
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.0021
NSC78017
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.0055
NSC78021
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.0021
NSC86715
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.0027
NSC97374
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.0051
NSC99495
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.006
NSC99528
Homo sapiens
-
in 50 mM phosphate buffer at pH 7.4, at 37C
-
0.0014
quercetin
Homo sapiens
-
IC50: 0.0014 mM
0.0015
quercetin-3-O-beta-glucopyranosyl
Homo sapiens
-
IC50: 0.0015 mM
0.000129 - 0.07
resveratrol
0.0012 - 0.0151
S26695
0.00091
S28128
Homo sapiens
-
IC50: 0.00091 mM
0.0000007 - 0.000079
S29434
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
-
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.5
-
assay at
8.5
-
assay at
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30
-
assay at
37
-
assay at
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
no significant difference in expression in normal and malignant biliary tissue. Activity of NQO2 is significatly lower than in hepatocellular tissue
Manually annotated by BRENDA team
-
-
Manually annotated by BRENDA team
-
the high NQO2 activity of intraperitoneal ovarian metastases relative to other tissues indicates a potential for tretazicar therapy in the treatment of this disease
Manually annotated by BRENDA team
-
minimal expression
Manually annotated by BRENDA team
-
suppression of vascular smooth muscle cell proliferation mediated by resveratrol correlates with vascular smooth muscle cell downregulation
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
PDB
SCOP
CATH
ORGANISM
UNIPROT
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
40000
-
gel filtration
50000
-
gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
-
x * 24600, SDS-PAGE
homodimer
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
2.1 A resolution
crystal structure of the enzyme in complex with resveratrol. Crystals of the native QR2 and QR2-resveratrol complex all belong to the P2(1)2(1)2(1) space group
-
purified NQO2 in complex with primaquine and chloroquine, hanging drop vapor diffusion method, against reservoirs containing 0.1 M HEPES, pH 7.5, and 1.3-2.0 M (NH4)2SO4, crystals of NQO2-CQ are soaked in 0.001 ml of reducing-soak solution consisting of 0.1 M HEPES, pH 7.5, 2.0 M (NH4)2SO4, 10 mM 1-(3-sulfonatopropyl)-3-carbamoyl-1,4-dihydropyrimidine and 1 mM chloroquine, X-ray diffraction structure determination and analysis at 1.2-1.4 A resolution
-
purified recombinant enzyme, hanging-drop, vapor-diffusion method, mixing of 0.001 ml of 4 mg/ml protein solution with 0.001 ml of reservoir solution containing 1.3-1.7 M ammonium sulfate, 0.1 M Bis-Tris buffer, pH 6.0-7.0, 0.1 M NaCl, 5 mM DTT, 0.012 mM FAD, and resveratrol, complexed with different inhibitors, X-ray diffraction structure determination and analysis at resolutions of 1.40-1.63 A
-
the crystal structure of melatonin and 2-iodomelatonin in complex with quinone reductase 2 provide a detailed description of the enzyme active site that can now be utilized in the design of new and potent inhibitors of the enzyme, hanging-drop vapour-diffusion method
-
X-ray crystal structure of NQO2 bound to imatinib to 1.75 A resolution. The X-ray structure provides an explanation for the binding specificity of NQO2 for imatinib and nilotinib, as well as for the effects of mutation of the reported phosphorylation sites on NQO2
-
X-ray crystallography studies of QR2 in complex with 6-methoxy-9-methyl-[1,3]dioxolo[4,5-h]quinolin-8(9H)-one
-
crystal structure of quinone reductase 2 in complexes with dopamine and adrenochrome
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
DEAE Sepharose, Superdex 75 column chromatography and Mono-Q column chromatography
-
Ni-NTA column chromatography
-
recombinant enzyme from Escherichia coli strain BL21(DE3)
-
recombinant His-tagged OR2 from Spodoptera frugiperda Sf9 cells by nickel affinity chromatography
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
CHO-K1 cells transiently expressing the mutated form of hQR2
-
expressed in Chinese hamster ovary cells and Escherichia coli
-
expressed in Escherichia coli
-
expressed in Hep-G2 cells
-
expressed in Sf9 insect cells
-
expression in CHO cells
-
expression in Escherichia coli strain BL21(DE3)
-
expression of His-tagged OR2 in Spodoptera frugiperda Sf9 cells
-
expression of recombinant QR2 in Spodoptera frugiperda Sf9 cells using the baculovirus transfection method
-
overexpression in Escherichia coli
-
the His-tagged enzyme is expressed in the Sf9 Spodoptera frugiperda ovarian cell line ATCC CRL-1711
-
the mouse NQO2 cDNA is subcloned into the pMT2 eukaryotic expression vector which, upon transfection in monkey kidney COS1 cells, produce a significant increase in NQO2 activity. Deletion of 54 amino acids from the N-terminus of the mouse NQO2 protein results in the loss of NQO2 expression and activity in transfected COS1 cells
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
C222F
-
mutation, which is distant from the determined binding site of the ligand, increases the affinity of [125I]-iodo-5-methoxycarbonylamino-N-acetyltryptamine for the enzyme
F126Y
-
substitution of the hydrophobic residue by tyrosines at the active site significantly increases enzymatic activity and decreases the affinity of a structural analog of melatonin, 2-[125I]-iodo-5-methoxycarbonylamino-N-acetyltryptamine
F131M
-
mutant enzyme is more active than wild-type enzyme
F178Y
-
substitution of the hydrophobic residue by tyrosines at the active site significantly increases enzymatic activity and decreases the affinity of a structural analog of melatonin, 2-[125I]-iodo-5-methoxycarbonylamino-N-acetyltryptamine
H11F
-
mutation of residue in FAD binding site, the enzymatic activity is unchanged
H173Y
-
mutation of residues implicated in zinc chelating (His173 or His177) has no effect on radioligand binding
H177R
-
mutation of residues implicated in zinc chelating (His173 or His177) has no effect on radioligand binding
I128Y
-
substitution of the hydrophobic residue by tyrosines at the active site significantly increases enzymatic activity and decreases the affinity of a structural analog of melatonin, 2-[125I]-iodo-5-methoxycarbonylamino-N-acetyltryptamine
N161A
-
mutation, which is distant from the determined binding site of the ligand, increases the affinity of [125I]-iodo-5-methoxycarbonylamino-N-acetyltryptamine for the enzyme
N161H
-
results in the total loss of the enzymatic activity towards activation of 5-(aziridin-1-yl)-2,4-dinitrobenzamide, whereas the rates of reduction towards menadione are not altered
N18Q
-
mutation of residue in FAD binding site, the enzymatic activity is diminished
additional information
-
construction of a chimeric enzyme of the human NQO2 with 43 amino acids from the carboxyl terminus of human DT-diaphorase. HNQO2-hDT43 still uses dihydronicotinamide riboside as an electron donor. The chimeric enzyme is inhibited by quercetin but not dicoumarol
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
medicine
Show AA Sequence (159 entries)
Please use the Sequence Search for a certain query.