Information on EC 1.13.11.52 - indoleamine 2,3-dioxygenase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.13.11.52
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RECOMMENDED NAME
GeneOntology No.
indoleamine 2,3-dioxygenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
D-tryptophan + O2 = N-formyl-D-kynurenine
show the reaction diagram
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L-tryptophan + O2 = N-formyl-L-kynurenine
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
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redox reaction
reduction
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
3-hydroxy-4-methyl-anthranilate biosynthesis I
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3-hydroxy-4-methyl-anthranilate biosynthesis II
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L-tryptophan degradation I (via anthranilate)
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L-tryptophan degradation to 2-amino-3-carboxymuconate semialdehyde
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L-tryptophan degradation XI (mammalian, via kynurenine)
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tryptophan metabolism
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Tryptophan metabolism
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Metabolic pathways
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SYSTEMATIC NAME
IUBMB Comments
D-tryptophan:oxygen 2,3-oxidoreductase (decyclizing)
A protohemoprotein. Requires ascorbic acid and methylene blue for activity. This enzyme has broader substrate specificity than EC 1.13.11.11, tryptophan 2,3-dioxygenase [1]. It is induced in response to pathological conditions and host-defense mechanisms and its distribution in mammals is not confined to the liver [2]. While the enzyme is more active with D-tryptophan than L-tryptophan, its only known function to date is in the metabolism of L-tryptophan [2,6]. Superoxide radicals can replace O2 as oxygen donor [4,7].
CAS REGISTRY NUMBER
COMMENTARY hide
9014-51-1
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Uniprot
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
strain ATCC 19213
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
Frog
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
MIP-I; no activity by IDO-like Mb
UniProt
Manually annotated by BRENDA team
recombinantly expressed in Escherichia coli as a N-terminally His6-tagged protein
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Manually annotated by BRENDA team
recombinantly expressed in Escherichia coli as a N-terminally His6-tagged protein
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Manually annotated by BRENDA team
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SwissProt
Manually annotated by BRENDA team
DBA/2J
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
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
1-benzofuran-DL-tryptophan + O2
?
show the reaction diagram
-
1 mM, 22% activity relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min
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-
?
1-benzothiophene-DL-tryptophan + O2
?
show the reaction diagram
-
1 mM, 19% activity relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min
-
-
?
1-methyl-D-tryptophan + O2
1-methyl-N-formyl-D-kynurenine
show the reaction diagram
-
-
-
-
?
1-methyl-DL-tryptophan + O2
?
show the reaction diagram
-
1 mM, 7% activity relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min
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-
?
1-methyl-L-tryptophan + O2
1-methyl-N-formyl-L-kynurenine
show the reaction diagram
-
-
-
-
?
1-methyl-L-tryptophan + O2
?
show the reaction diagram
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-
-
-
?
1H-indole + H2O + O2
2,3-dihydro-1H-indole-2,3-diol
show the reaction diagram
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-
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2-bromo-L-tryptophan + O2
?
show the reaction diagram
-
1 mM, 21% activity relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min
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-
?
2-chloro-L-tryptophan + O2
?
show the reaction diagram
-
1 mM, 33% activity relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min
-
-
?
2-hydroxy-L-tryptophan + O2
?
show the reaction diagram
-
1 mM, 4% activity relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min
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-
?
3-indoleethanol + O2-
?
show the reaction diagram
-
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-
?
3-N-aminoethyl-tryptophan + O2
?
show the reaction diagram
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1 mM, 32% activity relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min
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-
?
4-methyl-DL-tryptophan + O2
?
show the reaction diagram
-
1 mM, 33% activity relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min
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-
?
5-benzyloxy-DL-tryptophan + O2
?
show the reaction diagram
-
1 mM, 1% activity relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min
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?
5-bromo-DL-tryptophan + O2
?
show the reaction diagram
-
1 mM, 36% activity relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min
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?
5-fluoro-DL-tryptophan + O2
5-fluoro-N-formyl-DL-kynurenine
show the reaction diagram
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?
5-fluoro-DL-tryptophan + O2
?
show the reaction diagram
5-fluoro-L-tryptophan + O2
5-fluoro-N-formyl-L-kynurenine
show the reaction diagram
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?
5-fluoro-tryptophan + O2
4-(2-amino-5-fluorophenyl)-2-(formylamino)-4-oxobutanoic acid
show the reaction diagram
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?
5-fluoro-tryptophan + O2
?
show the reaction diagram
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?
5-fluorotryptophan + O2
?
show the reaction diagram
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?
5-hydroxy-L-tryptophan + O2
(2S)-4-(2-amino-5-hydroxyphenyl)-2-(formylamino)-4-oxobutanoic acid
show the reaction diagram
5-hydroxy-L-tryptophan + O2
5-hydroxy-N-formyl-L-kynurenine
show the reaction diagram
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?
5-hydroxy-L-tryptophan + O2
?
show the reaction diagram
5-hydroxy-L-tryptophan + O2
N-formyl-5-hydroxy-L-kynurenine
show the reaction diagram
5-hydroxy-tryptophan + O2
4-(2-amino-5-hydroxyphenyl)-2-(formylamino)-4-oxobutanoic acid
show the reaction diagram
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?
5-hydroxytryptamine + O2
?
show the reaction diagram
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?
5-hydroxytryptophan + O2
?
show the reaction diagram
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?
5-hydroxytryptophan + O2-
N-formyl-5-hydroxykynurenine
show the reaction diagram
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?
5-methoxy-D,L-tryptophan + O2
?
show the reaction diagram
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1 mM, 70% activity relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min
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?
5-methoxy-DL-tryptophan + O2
5-methoxy-N-formyl-DL-kynurenine
show the reaction diagram
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?
5-methoxy-L-tryptophan + O2
5-methoxy-N-formyl-L-kynurenine
show the reaction diagram
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?
5-methyl-D,L-tryptophan + O2
?
show the reaction diagram
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1 mM, 123% activity relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min
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?
5-methyl-DL-tryptophan + O2
5-methyl-N-formyl-DL-kynurenine
show the reaction diagram
5-methyl-DL-tryptophan + O2
?
show the reaction diagram
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?
5-methyl-tryptophan + O2
4-(2-amino-5-methylphenyl)-2-(formylamino)-4-oxobutanoic acid
show the reaction diagram
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?
5-methyltryptophan + O2
?
show the reaction diagram
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?
6-fluoro-DL-tryptophan + O2
?
show the reaction diagram
6-fluorotryptophan + O2
?
show the reaction diagram
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?
6-methyl-DL-tryptophan + O2
6-methyl-N-formyl-DL-kynurenine
show the reaction diagram
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?
6-methyl-DL-tryptophan + O2
?
show the reaction diagram
6-nitro-L-tryptophan + O2
?
show the reaction diagram
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1 mM, 2% activity relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min
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?
7-methyl-DL-tryptophan + O2
?
show the reaction diagram
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1 mM, 18% activity relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min
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-
?
alpha-methyl-DL-tryptophan + O2
?
show the reaction diagram
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1 mM, 35% activity relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min
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?
alpha-methyl-DL-tryptophan + O2-
?
show the reaction diagram
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-
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?
alpha-N-methyl-L-tryptophan + O2
?
show the reaction diagram
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1 mM, 21% activity relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min
-
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?
beta-methyl-DL-tryptophan + O2
?
show the reaction diagram
-
1 mM, 32% activity relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min
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?
beta-[3-benzo(b)thienyl]-L-alanine + O2
?
show the reaction diagram
-
-
-
-
?
D-5-hydroxytryptophan + O2
?
show the reaction diagram
D-Trp + O2
D-formylkynurenine
show the reaction diagram
D-Trp + O2
N-formyl-D-kynurenine
show the reaction diagram
D-tryptophan + O2
?
show the reaction diagram
-
-
-
-
?
D-tryptophan + O2
D-kynurenine
show the reaction diagram
-
-
-
-
?
D-tryptophan + O2
N-formyl-D-kynurenine
show the reaction diagram
D-tryptophan + O2-
N-formyl-D-kynurenine
show the reaction diagram
DL-5-fluoro-methyltryptophan + O2
?
show the reaction diagram
DL-5-methyltryptophan + O2
?
show the reaction diagram
DL-6-fluorotryptophan + O2
?
show the reaction diagram
DL-6-methyltryptophan
?
show the reaction diagram
DL-alpha-methyltryptophan + O2
alpha-methyl-N-formyl-DL-kynurenine
show the reaction diagram
-
9.0% of the activity with L-Trp
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?
indole + O2
?
show the reaction diagram
indole + O2-
?
show the reaction diagram
-
-
-
-
?
indole-3-propionic acid + O2
?
show the reaction diagram
-
altered kinetics for IPA (very long lag phase) as being consistent with a role for the ammonium group in stabilizing the ferric superoxide complex (via the radical pathway). The rate-limiting steps are different from the other substrates examined so that Compound II does not accumulate, but product formation is still possible, product formation ananlysis by LC-MS
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?
kynurenine
?
show the reaction diagram
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?
L-5-hydroxytryptophan + O2
?
show the reaction diagram
L-Trp + O2
L-formylkynurenine
show the reaction diagram
L-Trp + O2
N-formyl-L-kynurenine
show the reaction diagram
-
-
-
?
L-tryptophan + O2
L-kynurenine
show the reaction diagram
-
-
-
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?
L-tryptophan + O2
N-formyl-L-kynurenine
show the reaction diagram
L-tryptophan + O2
N-formylkynurenine
show the reaction diagram
L-tryptophan + O2-
N-formyl-L-kynurenine
show the reaction diagram
L-tryptophan ethyl ester + O2
?
show the reaction diagram
-
1 mM, 14% activity relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min
-
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?
L-tryptophan methyl ester + O2
?
show the reaction diagram
-
1 mM, 15% activity relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min
-
-
?
N-acetyl-L-tryptophan + O2
?
show the reaction diagram
-
1 mM, 3% activity relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min
-
-
?
serotonin + O2
?
show the reaction diagram
serotonin + O2-
?
show the reaction diagram
-
-
-
-
?
Trp + O2
formylkynurenine
show the reaction diagram
-
-
-
-
?
tryptamine + O2
?
show the reaction diagram
tryptamine + O2-
?
show the reaction diagram
-
-
-
-
?
tryptophan + O2
N-formylkynurenine
show the reaction diagram
-
if the cellular environment protects indoleamine 2,3-dioxygenase from oxidation to the ferric form, no additional electron donor might by required for indolamine 2,3-dioxygenase activity in intact tissues
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?
additional information
?
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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
5-hydroxy-L-tryptophan + O2
N-formyl-5-hydroxy-L-kynurenine
show the reaction diagram
D-tryptophan + O2
N-formyl-D-kynurenine
show the reaction diagram
L-Trp + O2
L-formylkynurenine
show the reaction diagram
L-tryptophan + O2
N-formyl-L-kynurenine
show the reaction diagram
L-tryptophan + O2-
N-formyl-L-kynurenine
show the reaction diagram
serotonin + O2
?
show the reaction diagram
tryptamine + O2
?
show the reaction diagram
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
FMNH2
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4-5-fold higher activity than acitivity with methylene blue as the electron donor
methylene blue
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stimulates the formation of D-kynurenine
tetrahydrobiopterin
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additional information
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Cd2+
-
0.007-0.1 mM, maximal stimulation at 0.007 mM
CN-
-
enhances the affinity for L-tryptophan for the ferric enzyme in reziprocal manner, positive cooperativity
copper
F-
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enhances the affinity for L-tryptophan for the ferric enzyme in reziprocal manner, positive cooperativity
N3-
-
enhances the affinity for L-tryptophan for the ferric enzyme in reziprocal manner, positive cooperativity
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(10Z,13Z)-nonadecadienoic acid
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32% inhibition at 0.02 mM
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(11Z,14Z)-eicosadienoic acid
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42% inhibition at 0.02 mM
(11Z,14Z,17Z)-eisosatrienoic acid
-
19% inhibition at 0.02 mM
-
(12Z,15Z)-heneicosadienoic acid
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39% inhibition at 0.02 mM
-
(13Z,16Z)-docosadienoic acid
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39% inhibition at 0.02 mM
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(13Z,16Z,19Z)-docosatrienoic acid
-
52% inhibition at 0.02 mM
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(2,4-dichlorophenyl)methanethiol
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(2-chlorophenyl)methanethiol
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(3,4-dichlorophenyl)methanethiol
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(3-hydroxyphenyl)(phenyl)methanone
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(3R,4S and 3S,4R)-3-bromo-4-hydroxy-2,2-dimethyl-3,4-dihydro-2H-benzo[g]chromene-5,10-dione
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(3R,4S and 3S,4R)-3-hydroxy-2,2-dimethyl-4-morpholino-3,4-dihydro-2H-benzo[g]chromene-5,10-dione
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(3R,4S and 3S,4R)-3-hydroxy-4-methoxy-2,2-dimethyl-3,4-dihydro-2H-benzo[g]chromene-5,10-dione
-
-
(3R,4S and 3S,4R)-4-(allylamino)-3-hydroxy-2,2-dimethyl-3,4-dihydro-2H-benzo[g]chromene-5,10-dione
-
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(3R,4S and 3S,4R)-4-(benzylamino)-3-hydroxy-2,2-dimethyl-3,4-dihydro-2H-benzo[g]chromene-5,10-dione
-
-
(3R,4S and 3S,4R)-4-(benzylthio)-3-hydroxy-2,2-dimethyl-3,4-dihydro-2H-benzo[g]chromene-5,10-dione
-
-
(3R,4S and 3S,4R)-4-(butylamino)-3-hydroxy-2,2-dimethyl-3,4-dihydro-2H-benzo[g]chromene-5,10-dione
-
-
(3S,4S and 3R,4R)-3,4-dihydroxy-2,2-dimethyl-3,4-dihydro-2H-benzo[g]chromene-5,10-dione
-
alpha-lapachone
(3S,4S and 3R,4R)-3-hydroxy-2,2-dimethyl-4-morpholino-3,4-dihydro-2H-benzo[g]chromene-5,10-dione
-
-
(3S,4S and 3R,4R)-3-hydroxy-4-methoxy-2,2-dimethyl-3,4-dihydro-2H-benzo[g]chromene-5,10-dione
-
-
(3S,4S and 3R,4R)-4-(allylamino)-3-hydroxy-2,2-dimethyl-3,4-dihydro-2H-benzo[g]chromene-5,10-dione
-
-
(3S,4S and 3R,4R)-4-(benzylamino)-3-hydroxy-2,2-dimethyl-3,4-dihydro-2H-benzo[g]chromene-5,10-dione
-
-
(3S,4S and 3R,4R)-4-(benzyloxy)-3-hydroxy-2,2-dimethyl-3,4-dihydro-2H-benzo[g]chromene-5,10-dione
-
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(3S,4S and 3R,4R)-4-(benzylthio)-3-hydroxy-2,2-dimethyl-3,4-dihydro-2H-benzo[g]chromene-5,10-dione
-
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(3S,4S)-4-(benzylamino)-3,9-dihydroxy-2,2-dimethyl-3,4-dihydro-2H-benzo[g]chromene-5,10-dione
-
-
(3S,4S)-4-(butylamino)-3-hydroxy-2,2-dimethyl-3,4-dihydro-2H-benzo[g]chromene-5,10-dione
-
-
(4-chlorophenyl)methanethiol
-
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(4-chlorophenyl)methanol
-
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(4-fluorophenyl)methanethiol
-
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(4-methoxyphenyl)methanethiol
-
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(4-methylphenyl)methanethiol
-
-
(4E,4'E)-4,4'-bis(isopropylimino)-2,2'-binaphthyl-1,1'-(4H,4'H)-dione
-
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(4E,4'E)-4,4'-bis(pentan-3-ylimino)-2,2'-binaphthyl-1,1'-(4H,4'H)-dione
-
-
(4Z,7Z,10Z,13Z,16Z)-docosapentaenoic acid
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48% inhibition at 0.02 mM
-
(4Z,7Z,10Z,13Z,16Z,19Z)-Docosahexaenoic acid
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35% inhibition at 0.02 mM
(5Z,8Z)-eicosadienoic acid
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42% inhibition at 0.02 mM
-
(5Z,8Z,11Z)-eisosatrienoic acid
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45% inhibition at 0.02 mM
-
(5Z,8Z,11Z,14Z)-eicosatetraenoic acid
-
55% inhibition at 0.02 mM; 80% inhibition at 0.02 mM
(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoic acid
-
19% inhibition at 0.02 mM
(7Z,10Z,13Z,16Z)-docosatetraenoic acid
-
42% inhibition at 0.02 mM
-
(7Z,7Z)-dimethyleicosadienoic acid
-
29% inhibition at 0.02 mM
-
(8Z,11Z,14Z)-eisosatrienoic acid
-
68% inhibition at 0.02 mM
-
(9E,11Z)-octadecadienoic acid
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26% inhibition at 0.02 mM
-
(9E,12E)-octadecadienoic acid
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23% inhibition at 0.02 mM
-
(9Z,12Z)-octadecadienoic acid
-
16% inhibition at 0.02 mM
(9Z,12Z,15Z)-octadecatrienoic acid
-
23% inhibition at 0.02 mM
(E)-4-(isopropylimino)-2-methylnaphthalen-1(4H)-one
-
-
(E)-6-fluoro-3-[2-(3-pyridyl)vinyl]-1H-indole
-
-
(R)-2-amino-N-(4-hydroxynaphth-1-yl)propanamide
-
-
(S)-2-amino-5-((R)-1-(carboxymethylamino)-3-(1,4-dihydroxy-3-methylnaphthalen-2-ylthio)-1-oxopropan-2-ylamino)-5-oxopentanoic acid
-
-
(S)-2-amino-5-((R)-1-(carboxymethylamino)-3-(3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-ylthio)-1-oxopropan-2-ylamino)-5-oxopentanoic acid
-
-
(S)-2-amino-N-(4-hydroxynaphth-1-yl)propanamide
-
-
1,2-naphthoquinone
-
-
1,4-naphtho-quinone
-
-
1-(1,3-benzothiazol-2-ylsulfanyl)-N,N-dimethylmethanamine
-
-
1-(2-methylbenzyl)-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione
-
-
1-(3-bromobenzyl)-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione
-
-
1-(3-chlorobenzyl)-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione
-
-
1-(3-[(4-acetyl-1-piperazinyl)carbonyl]benzyl)-1H-naphtho-[2,3-d][1,2,3]triazole-4,9-dione
-
-
1-(3-[(4-methyl-1-piperazinyl)carbonyl]benzyl)-1H-naphtho-[2,3-d][1,2,3]triazole-4,9-dione
-
-
1-(4-bromobenzyl)-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione
-
-
1-(4-chlorobenzyl)urea
-
-
1-(4-chlorophenyl)methanamine
-
-
1-(4-chlorophenyl)thiourea
-
-
1-(4-fluorobenzyl)-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione
-
-
1-(4-methylbenzyl)-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione
-
-
1-(4-[(4-acetylpiperazin-1-yl)carbonyl]benzyl)-1H-naphtho-[2,3-d][1,2,3]triazole-4,9-dione
-
-
1-(4-[(4-methoxypiperidin-1-yl)carbonyl]benzyl)-1Hnaphtho[2,3-d][1,2,3]triazole-4,9-dione
-
-
1-benzofuran-DL-tryptophan
-
1 mM, 43% inhibition relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min
-
1-benzothiophene-DL-tryptophan
-
1 mM, 16% inhibition relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min
-
1-benzyl-5-phenyl-1H-imidazole
-
-
1-cyclohexyl-2-(5H-imidazo[5,1-a]isoindol-5-yl)ethan-1-ol
-
-
1-hydroxy-5,6-dimethoxy-3-oxo-2-phenyl-3H-indol-1-ium
-
-
1-L-methyltryptophan
1-methyl tryptophan
-
a tryptophan analogue. Galanal does not decrease the IkappaB-alpha expression in LPS-stimulated THP-1 cells
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1-methyl-D-tryptophan
1-methyl-DL-Trp
-
-
1-methyl-DL-tryptophan
1-methyl-L-tryptophan
1-methyl-tryptophan
1-Methyltryptophan
1-oxo-2-phenyl-3H-1lambda5-indol-3-one
-
-
1-phenyl-2-(phenylsulfanyl)hydrazine
-
-
1-[(3-methylphenyl)methyl]-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione
-
-
1-[(4-chlorophenyl)methyl]-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione
-
-
1-[2-(4-chlorophenyl)ethyl]thiourea
-
-
1-[3-(4-morpholinylcarbonyl)benzyl]-1H-naphtho[2,3-d]-[1,2,3]triazole-4,9-dione
-
-
1-[4-(morpholin-4-ylcarbonyl)benzyl]-1H-naphtho[2,3-d]-[1,2,3]triazole-4,9-dione
-
-
1-[4-[(4-methylpiperazin-1-yl)carbonyl]benzyl]-1H-naphtho-[2,3-d][1,2,3]triazole-4,9-dione
-
-
15-deoxy-DELTA12,14-prostaglandin
-
-
1H-benzotriazole
-
-
1H-phenanthro[9,10-d]imidazole
-
-
2,1,3-benzothiadiazole
-
-
2,1,3-benzoxadiazole
-
-
2,2-dimethyl-1a,9b-dihydro-2H-benzo[g]oxireno[c]chromene-4,9-dione
-
-
2,2-dimethyl-2H-benzo[g]chromene-5,10-dione
-
dehydro-alpha-lapachone
2,2-dimethyl-3,4-dihydro-2H-benzo[g]chromene-5,10-dione
-
-
2,2-dimethyl-3,4-epoxy-2H-naphtho[2,3-b]pyran-5,10-dione
-
-
2,3-dichloro-1,4-naphthoquinone
-
-
2,4-dichlorobenzyl carbamimidothioate hydrobromide
-
-
2-(1H-imidazol-4-yl)benzene-1,3-diol
-
-
2-(1H-imidazol-4-yl)benzenethiol
-
-
2-(1H-imidazol-4-yl)phenol
-
-
2-(1H-phenanthro[9,10-d]imidazol-2-yl)phenol
-
-
2-(1H-pyrazol-3-yl)phenol
-
-
2-(2-chlorophenyl)ethyl carbamimidothioate hydrobromide
-
-
2-(2-fluorophenyl)-1H-phenanthro[9,10-d]imidazole
-
-
2-(2-methylphenyl)-1-oxo-3H-1lambda5-indol-3-one
-
-
2-(2-methylphenyl)-1H-phenanthro[9,10-d]imidazole
-
-
2-(3-chlorophenyl)ethyl carbamimidothioate hydrobromide
-
-
2-(4-chlorophenyl)ethanamine
-
-
2-(4-chlorophenyl)ethyl carbamimidothioate hydrobromide
-
-
2-(4-methoxyphenyl)-1-oxo-3H-1lambda5-indol-3-one
-
-
2-(4-methoxyphenyl)-3H-indol-3-one
-
-
2-(4-methoxyphenyl)-3H-indole
-
-
2-(4-[(4,9-dioxo-4,9-dihydro-1H-naphtho[2,3-d][1,2,3]-triazol-1-yl)methyl]phenyl)-N,N-diethylacetamide
-
-
2-([5-(3-methoxyphenyl)[1,3]thiazolo[2,3-c][1,2,4]triazol-3-yl]sulfanyl)-N-(5-methyl-1,3-thiazol-2-yl)acetamide
F5H5G0, P14902
poor inhibitor; poor inhibitor
2-amino-3-hydroxy-N-(4-hydroxynaphthalen-1-yl)propanamide
-
-
2-amino-N-(4-hydroxynaphth-1-yl)acetamide
-
-
2-bromo-L-tryptophan
-
1 mM, 11% inhibition relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min
2-chloro-L-tryptophan
-
1 mM, 20% inhibition relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min
2-chloro-N-[[(4-chlorophenyl)sulfanyl]methyl]aniline
-
-
2-chlorobenzyl carbamimidothioate hydrochloride
-
-
2-Hydroxy-1,4-naphthoquinone
-
-
2-hydroxy-L-tryptophan
-
1 mM, 30% inhibition relative to L-tryptophan, 50 mM potassium phosphate, pH 6.5, 10 mM ascorbic acid, 0.01 mM methylene blue, 0.1 mg catalase, 37°C, 10 min
2-hydroxygarveatin E
-
-
2-hydroxygarvin A
-
-
2-mercaptobenzothiazole
-
-
2-methoxy-1,4-naphthoquinone
-
-
2-methyl-1,4-naphthoquinone
-
-
2-methylindole
-
-
2-methylnaphthalene-1,4-dione
-
-