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(R)-2,10,11-trihydroxy-N-n-propylaporphine
(R)-2,10,11-trihydroxyaporphine
(R)-2,11-dihydroxy-10-methoxy-aporphine
(R)-N-chloroethylnorapomorphine
(R)-N-hydroxyethylnorapomorphine
(R)-N-n-propylnorapomorphine
(S)-2,10,11-trihydroxyaporphine
(S)-N-n-propylnorapomorphine
1-methyl-4-(3',4'-dihydroxyphenyl)-1,2,3,6-tetrahydropyridine
1-methyl-4-(3'-methoxy-4'-hydroxyphenyl)-1,2,3,6-tetrahydropyridine
1-methyl-4-(4'-chlorophenyl)-1,2,3,6-tetrahydropyridine
1-methyl-4-(4'-hydroxyphenyl)-1,2,3,6-tetrahydropyridine
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
2,4-diamino-7,8-dihydropteroylglutamic acid
-
-
2,4-diaminopteroic acid
-
-
2,4-diaminopteroylglutamic acid
-
-
2,6-dichlorophenolindophenol
3',4'-deoxynorlaudanosolinecarboxylic acid
-
noncompetitive vs. quinoid 2-amino-6,7-dimethyl-4-hydroxydihydropteridine and NADH
3(4-hydroxyphenyl)pyruvate
3-iodotyrosine
-
weak inhibition
3-O-methyldopamine
-
0.06 mM, 50% inhibition
3-O-Methylepinephrine
-
0.18 mM, 50% inhibition
4-(3',4'-dihydroxyphenyl)-1,2,3,6-tetrahydropyridine
4-(3'-methoxy-4'-hydroxyphenyl)-1,2,3,6-tetrahydropyridine
4-(4'-chlorophenyl)-1,2,3,6-tetrahydropyridine
4-(4'-hydroxyphenyl)-1,2,3,6-tetrahydropyridine
4-O-Methyldopamine
-
0.069 mM, 50% inhibition
4-phenyl-1,2,3,6-tetrahydropyridine
4-[(1R)-2-amino-1-hydroxyethyl]benzene-1,2-diol
5,5'-dithiobis(2-nitrobenzoate)
5-Hydroxydopamine
-
0.042 mM, 50% inhibition
6-Hydroxydopamine
-
0.029 mM, 50% inhibition
alpha-Methyltyrosine
-
1.1 mM, 50% inhibition
aminochrome
-
oxidation product of adrenaline, competitive vs. NADH
CdCl2
-
0.1 mM, complete inactivation
cis-Diaminodichloroplatinum
-
-
CoCl2
-
0.01 mM, 30% inhibition
dopachrome
-
0.6 mM, 50% inhibition
epinephrine
-
0.13 mM, 50% inhibition
H2O2
regulatory function in vivo, above 0.03 mM, oxidation of Met146 and Met151 leads to inactivation of the enzyme due to disruption of the NADH-binding site
higenamine
-
noncompetitive vs. quinoid 2-amino-6,7-dimethyl-4-hydroxydihydropteridine and NADH
higenamine-1-carboxylic acid
-
noncompetitive vs. quinoid 2-amino-6,7-dimethyl-4-hydroxydihydropteridine
K2PtCl4
-
0.208 mM, half-life of inactivation: 3.1 min, NADH and 2 mM dithiothreitol completely protect
L-beta-3,4-dihydroxyphenylalanine
L-thyroxine
-
mixed-type inhibition
MgCl2
-
0.1 mM, complete inactivation
MnCl2
-
0.1 mM, complete inactivation
N-Methyldopamine
-
0.027 mM, 50% inhibition
NAD+
-
competitive vs. NADH
NADP+
-
competitive vs. NADPH
norepinephrine
-
0.2 mM, 50% inhibition
o-hydroxyphenylacetic acid
octopamine
-
0.19 mM, 50% inhibition
quinonoid 2,4-diamino-7,8-dihydropteroylglutamic acid
-
-
quinonoid 6,6,8-trimethyl-7,8-dihydro(6H)pterin
-
0.2 mM, 50% inhibition
quiononoid 2,4-diamino-7,8-dihydropteroylglutamic acid
-
-
salsolinol
-
noncompetitive vs. quinoid 2-amino-6,7-dimethyl-4-hydroxydihydropteridine
tetrahydrobiopterin
-
above 0.05 mM, substrate inhibition
trans-Diaminodichloroplatinum
-
-
trans-Pt(NH3)Cl2
-
1 mM, 96% inactivation after 2 h
[4-hydroxyphenyl]acetic acid
-
-
(R)-2,10,11-trihydroxy-N-n-propylaporphine
-
0.0017 mM, 50% inhibition
(R)-2,10,11-trihydroxy-N-n-propylaporphine
-
0.0016 mM, 50% inhibition
(R)-2,10,11-trihydroxyaporphine
-
0.0016 mM, 50% inhibition
(R)-2,10,11-trihydroxyaporphine
-
0.0007 mM, 50% inhibition
(R)-2,11-dihydroxy-10-methoxy-aporphine
-
0.013 mM, 50% inhibition
(R)-2,11-dihydroxy-10-methoxy-aporphine
-
0.016 mM, 50% inhibition
(R)-apocodeine
-
0.079 mM, 50% inhibition
(R)-apocodeine
-
0.087 mM, 50% inhibition
(R)-apomorphine
-
0.002 mM, 50% inhibition
(R)-apomorphine
-
0.0012 mM, 50% inhibition
(R)-N-chloroethylnorapomorphine
-
0.0029 mM, 50% inhibition
(R)-N-chloroethylnorapomorphine
-
0.0029 mM, 50% inhibition
(R)-N-hydroxyethylnorapomorphine
-
0.001 mM, 50% inhibition
(R)-N-hydroxyethylnorapomorphine
-
0.0013 mM, 50% inhibition
(R)-N-n-propylaporphine
-
-
(R)-N-n-propylaporphine
-
-
(R)-N-n-propylnorapomorphine
-
0.0018 mM, 50% inhibition
(R)-N-n-propylnorapomorphine
-
0.0017 mM, 50% inhibition
(R)-norapomorphine
-
0.0028 mM, 50% inhibition
(R)-norapomorphine
-
0.0014 mM, 50% inhibition
(S)-2,10,11-trihydroxyaporphine
-
0.0015 mM, 50% inhibition
(S)-2,10,11-trihydroxyaporphine
-
0.0014 mM, 50% inhibition
(S)-bulbocapnine
-
0.148 mM, 50% inhibition
(S)-bulbocapnine
-
0.151 mM, 50% inhibition
(S)-N-n-propylnorapomorphine
-
0.0022 mM, 50% inhibition
(S)-N-n-propylnorapomorphine
-
0.0018 mM, 50% inhibition
1-methyl-4-(3',4'-dihydroxyphenyl)-1,2,3,6-tetrahydropyridine
-
0.0034 mM, 50% inhibition
1-methyl-4-(3',4'-dihydroxyphenyl)-1,2,3,6-tetrahydropyridine
-
-
1-methyl-4-(3'-methoxy-4'-hydroxyphenyl)-1,2,3,6-tetrahydropyridine
-
0.0093 mM, 50% inhibition
1-methyl-4-(3'-methoxy-4'-hydroxyphenyl)-1,2,3,6-tetrahydropyridine
-
-
1-methyl-4-(4'-chlorophenyl)-1,2,3,6-tetrahydropyridine
-
0.27 mM, 50% inhibition
1-methyl-4-(4'-chlorophenyl)-1,2,3,6-tetrahydropyridine
-
-
1-methyl-4-(4'-hydroxyphenyl)-1,2,3,6-tetrahydropyridine
-
0.003 mM, 50% inhibition
1-methyl-4-(4'-hydroxyphenyl)-1,2,3,6-tetrahydropyridine
-
-
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
-
0.3 mM, 50% inhibition
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
-
-
2,6-dichlorophenolindophenol
-
0.0001 mM, 50% inhibition
2,6-dichlorophenolindophenol
-
inhibition of NADPH-specific enzyme
3(4-hydroxyphenyl)pyruvate
-
0.0033 mM, 50% inhibition
3(4-hydroxyphenyl)pyruvate
-
0.0044 mM, 50% inhibition
3-phenylpyruvic acid
-
4.7 mM, 50% inhibition
3-phenylpyruvic acid
-
5.9 mM, 50% inhibition
4-(3',4'-dihydroxyphenyl)-1,2,3,6-tetrahydropyridine
-
0.0036 mM, 50% inhibition
4-(3',4'-dihydroxyphenyl)-1,2,3,6-tetrahydropyridine
-
-
4-(3'-methoxy-4'-hydroxyphenyl)-1,2,3,6-tetrahydropyridine
-
0.0072 mM, 50% inhibition
4-(3'-methoxy-4'-hydroxyphenyl)-1,2,3,6-tetrahydropyridine
-
-
4-(4'-chlorophenyl)-1,2,3,6-tetrahydropyridine
-
0.34 mM, 50% inhibition
4-(4'-chlorophenyl)-1,2,3,6-tetrahydropyridine
-
-
4-(4'-hydroxyphenyl)-1,2,3,6-tetrahydropyridine
-
0.0059 mM, 50% inhibition
4-(4'-hydroxyphenyl)-1,2,3,6-tetrahydropyridine
-
-
4-hydroxyphenyllactate
-
0.058 mM, 50% inhibition
4-hydroxyphenyllactate
-
0.071 mM, 50% inhibition
4-phenyl-1,2,3,6-tetrahydropyridine
-
12 mM, 50% inhibition
4-phenyl-1,2,3,6-tetrahydropyridine
-
-
4-[(1R)-2-amino-1-hydroxyethyl]benzene-1,2-diol
-
no inhibition below 0.2 mM
4-[(1R)-2-amino-1-hydroxyethyl]benzene-1,2-diol
-
-
5,5'-dithiobis(2-nitrobenzoate)
-
0.1 mM, 60% inhibition
5,5'-dithiobis(2-nitrobenzoate)
-
0.57 mM, 98% inhibition
5,5'-dithiobis(2-nitrobenzoate)
-
no inactivation in the presence of NADH
aminopterin
-
0.025 mM, 50% inhibition of NADH-specific enzyme, 1 mM, 50% inhibition of NADPH-specific enzyme
aminopterin
-
1 mM, 50% inhibition, NADPH-specific enzyme
aminopterin
-
no inhibition up to 0.1 mM
aminopterin
-
0.025 mM, 50% inhibition of NADH-specific enzyme, 1 mM, 50% inhibition of NADPH-specific enzyme
aminopterin
-
1 mM, 50% inhibition
aminopterin
the DHFR inhibitor aminopterin inhibits tetrahydrobiopterin recycling. Aminopterin has no effect alone but slightly reduced L-citrulline formation and cGMP accumulation in the presence of dihydrobiopterin
aminopterin
-
competitive vs. 2-amino-4-hydroxy-6,7-dimethyl-quinonoid-dihydropteridine
aminopterin
the DHFR inhibitor aminopterin inhibits tetrahydrobiopterin recycling. Aminopterin has no effect alone but slightly reduced L-citrulline formation and cGMP accumulation in the presence of dihydrobiopterin
dopamine
-
no inhibition below 0.2 mM
dopamine
-
noncompetitive vs. quinonoid 2-amino-6,7-dimethyl-4-hydroxydihydropteridine
dopamine
-
0.1 mM, 50% inhibition
HgCl2
-
0.0001 mM, 60% inhibition
HgCl2
-
0.002 mM, 50% inhibition, enzyme from brain
L-beta-3,4-dihydroxyphenylalanine
-
0.23 mM, 50% inhibition
L-beta-3,4-dihydroxyphenylalanine
-
0.02 mM, 50% inhibition
L-beta-3,4-dihydroxyphenylalanine
-
0.8 mM, 50% inhibition after 3 h, 80% inhibition after 16 h due to oxidation of L-DOPA to dopachrome which inhibits the enzyme
L-beta-3,4-dihydroxyphenylalanine
-
trivial name L-DOPA, 0.34 mM, 50% inhibition
L-tyrosine
-
noncompetitive vs. NADPH
L-tyrosine
-
0.44 mM, 50% inhibition
L-tyrosine
-
0.61 mM, 50% inhibition
m-tyramine
-
0.036 mM, 50% inhibition
m-tyramine
-
0.044 mM, 50% inhibition
methopterin
-
0.038 mM, 50% inhibition of NADH-specific enzyme
methopterin
-
0.7 mM, 50% inhibition of NADPH-specific enzyme
methopterin
-
0.038 mM, 50% inhibition of NADH-specific enzyme; 0.7 mM, 50% inhibition of NADPH-specific enzyme
methopterin
-
1 mM, 10% inhibition
methotrexate
-
no inhibition up to 0.1 mM
methotrexate
-
competitive vs. quinoid 6-methyl-7,8-dihydropterin
N-ethylmaleimide
-
1 mM, 76% inhibition
N-ethylmaleimide
-
5 mM, complete inhibition of reduced enzyme
o-hydroxyphenylacetic acid
-
6.9 mM, 50% inhibition
o-hydroxyphenylacetic acid
-
8.1 mM, 50% inhibition
p-chloromercuribenzoate
-
0.01 mM, 70% inhibition
p-chloromercuribenzoate
-
0.2 mM, 50% inhibition, enzyme from brain
p-chloromercuribenzoate
-
0.4 mM, 50% inhibition
p-chloromercuribenzoate
-
complete inactivation at inhibitor/enzyme ratios greater than 6/1, NADH protects
phenylacetic acid
-
6.6 mM, 50% inhibition
phenylacetic acid
-
6.9 mM, 50% inhibition
phenylpyruvate
-
-
tyramine
-
0.04 mM, 50% inhibition
tyramine
-
0.046 mM, 50% inhibition
additional information
-
enzyme from adrenal medulla, not inhibited by aminopterin and methotrexate
-
additional information
-
quinone products of L-DOPA oxidation are responsible for the time-dependent inactivation of the enzyme
-
additional information
-
not inhibited by EDTA, o-phenanthroline, and 2,2'-bipyridyl
-