Information on EC 1.14.16.4 - tryptophan 5-monooxygenase

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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria

EC NUMBER
COMMENTARY hide
1.14.16.4
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RECOMMENDED NAME
GeneOntology No.
tryptophan 5-monooxygenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
L-tryptophan + tetrahydrobiopterin + O2 = 5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
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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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
serotonin and melatonin biosynthesis
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Tryptophan metabolism
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Folate biosynthesis
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Metabolic pathways
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SYSTEMATIC NAME
IUBMB Comments
L-tryptophan,tetrahydrobiopterin:oxygen oxidoreductase (5-hydroxylating)
The active centre contains mononuclear iron(II). The enzyme is activated by phosphorylation, catalysed by a Ca2+-activated protein kinase. The 4a-hydroxytetrahydrobiopterin formed can dehydrate to 6,7-dihydrobiopterin, both spontaneously and by the action of EC 4.2.1.96, 4a-hydroxytetrahydrobiopterin dehydratase. The 6,7-dihydrobiopterin can be enzymically reduced back to tetrahydrobiopterin, by EC 1.5.1.34 (6,7-dihydropteridine reductase), or slowly rearranges into the more stable compound 7,8-dihydrobiopterin.
CAS REGISTRY NUMBER
COMMENTARY hide
9037-21-2
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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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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A1Y9J6
UniProt
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
a planarian, gene TPH
UniProt
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
C57/BL6 mice
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Manually annotated by BRENDA team
no activity in Rattus norvegicus
PC-12 cells
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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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Uniprot
Manually annotated by BRENDA team
sp. scombroidei, yellofin tuna
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
metabolism
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
2-azaisotryptophan + 6-methyltetrahydropterin + O2
5-hydroxy-2-azaisotryptophan + 6-hydroxy-2-azaisotryptophan + 6-methyldihydropterin + H2O
show the reaction diagram
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recombinant N- and C-terminal truncated enzyme
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?
4-azatryptophan + 6-methyltetrahydropterin + O2
5-hydroxy-4-azatryptophan + 6-methyldihydropterin + H2O
show the reaction diagram
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recombinant N- and C-terminal truncated enzyme
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?
4-methyltryptophan + 6-methyltetrahydropterin + O2
5-hydroxy-4-methyltryptophan + 6-methyldihydropterin + H2O
show the reaction diagram
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recombinant N- and C-terminal truncated enzyme
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?
5-methyltryptophan + 6-methyltetrahydropterin + O2
5-hydroxymethyltryptophan + 5-hydroxy-4-methyltryptophan + 6-methyldihydropterin + H2O
show the reaction diagram
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recombinant N- and C-terminal truncated enzyme
more than 99% 5-hydroxymethyltryptophan
?
6-azatryptophan + 6-methyltetrahydropterin + O2
5-hydroxy-6-azatryptophan + 6-methyldihydropterin + H2O
show the reaction diagram
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recombinant N- and C-terminal truncated enzyme
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?
6-methyltryptophan + 6-methyltetrahydropterin + O2
5-hydroxy-6-methyltryptophan + 6-methyldihydropterin + H2O
show the reaction diagram
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recombinant N- and C-terminal truncated enzyme
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?
7-azatryptophan + 6-methyltetrahydropterin + O2
5-hydroxy-7-azatryptophan + 6-methyldihydropterin + H2O
show the reaction diagram
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recombinant N- and C-terminal truncated enzyme
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?
7-methyltryptophan + 6-methyltetrahydropterin + O2
5-hydroxy-7-methyltryptophan + 6-methyldihydropterin + H2O
show the reaction diagram
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recombinant N- and C-terminal truncated enzyme
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?
L-methionine + ? + O2
?
show the reaction diagram
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relative high activity with pronase-treated PTMO
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?
L-phenylalanine + tetrahydropteridine + O2
L-tyrosine + dihydropteridine + H2O
show the reaction diagram
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purified PTMO shows no activity, relative high activity with pronase-treated PTMO
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?
L-phenylalanine + tetrahydropteridine + O2
tyrosine + dihydropteridine + H2O
show the reaction diagram
L-tryptophan + (6R)-L-erytho-5,6,7,8-tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + ?
show the reaction diagram
L-tryptophan + (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan
show the reaction diagram
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?
L-tryptophan + (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
show the reaction diagram
L-tryptophan + 6-methyl-tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 6-methyl-4a-hydroxytetrahydrobiopterin
show the reaction diagram
L-tryptophan + 6-methyl-tetrahydropterin + O2
5-hydroxy-L-tryptophan + 6-methyl-4a-hydroxytetrahydropterin
show the reaction diagram
L-tryptophan + tetrahydrobiopterin
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
show the reaction diagram
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
show the reaction diagram
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
show the reaction diagram
L-tyrosine + tetrahydropteridine + O2
?
show the reaction diagram
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
L-tryptophan + (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
show the reaction diagram
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
show the reaction diagram
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
show the reaction diagram
additional information
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
tetrahydrobiopterin
additional information
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residue Y235 is involved in cofactor binding, residue is different from L-phenylalanine 4-hydroxylase
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(2S)-2-amino-5-(2-amino-6-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]pyrimidin-4-yl)pent-4-ynoic acid
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(3R)-8-(2-amino-6-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]pyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-3-carboxylic acid
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(3S)-8-(2-amino-6-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]pyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-3-carboxylic acid
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(3S)-8-(2-amino-6-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]pyrimidin-4-yl)-2-methyl-2,8-diazaspiro[4.5]decane-3-carboxylic acid
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(6R)-5,6,7,8-tetrahydrobiopterin
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(6R)-L-erytho-5,6,7,8-tetrahydrobiopterin
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TPH2, substrate inhibition
(7R)-5,6,7,8-tetrahydrobiopterin
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recombinant pinal enzyme, 2.1 mM, 50% inhibition
1,10-phenanthroline
2,2'-dipyridyl
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2-(2-amino-6-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]pyrimidin-4-yl)-2,6-diazaspiro[3.4]octane-7-carboxylic acid
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3,4-dihydroxyphenylalanine
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3,4-Dihydroxyphenylethylamine
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3,4-Dihydroxystyrene
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3,4-methylenedioxymethamphetamine
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inactivation of the enzyme
3-(2-amino-6-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]pyrimidin-4-yl)-N-(2-methylprop-2-en-1-yl)-3-azabicyclo[3.2.1]octan-8-amine
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3-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)phenylalanine
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3-amino-3-[1-(2-amino-6-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]pyrimidin-4-yl)piperidin-4-yl]propanoic acid
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3-amino-3-[4-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)phenyl]propanoic acid
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3-[(3R)-3-(2-amino-6-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]pyrimidin-4-yl)pyrrolidin-1-yl]-L-alanine
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3-[1-(2-amino-6-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]pyrimidin-4-yl)piperidin-4-yl]propanoic acid
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3-[1-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)piperidin-4-yl]alanine
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3-[3-(2-amino-6-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]pyrimidin-4-yl)-3,6-diazabicyclo[3.1.1]heptan-6-yl]-L-alanine
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3-[3-(2-amino-6-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]pyrimidin-4-yl)-3,8-diazabicyclo[3.2.1]octan-8-yl]-L-alanine
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3-[3-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)-1H-pyrazol-1-yl]alanine
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3-[4-(2-amino-6-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]pyrimidin-4-yl)-1,4-diazepan-1-yl]-L-alanine
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3-[4-(2-amino-6-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]pyrimidin-4-yl)piperazin-1-yl]-L-alanine
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3-[5-(2-amino-6-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]pyrimidin-4-yl)-2,5-diazabicyclo[2.2.2]octan-2-yl]-L-alanine
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3-[5-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)pyridin-2-yl]alanine
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3-[6-(2-amino-6-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]pyrimidin-4-yl)-3,6-diazabicyclo[3.1.1]heptan-3-yl]-L-alanine
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3-[8-(2-amino-6-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]pyrimidin-4-yl)-3,8-diazabicyclo[3.2.1]octan-3-yl]-L-alanine
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4-(4-amino-6-[methyl[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)-L-phenylalanine
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4-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)-2-fluorophenylalanine
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4-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)-a-methylphenylalanine
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4-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)-L-phenylalanine
4-(4-amino-6-[[(1S)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)-L-phenylalanine
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4-(4-amino-6-[[(4'-methylbiphenyl-4-yl)methyl]amino]-1,3,5-triazin-2-yl)-L-phenylalanine
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4-(4-amino-6-[[4-(trifluoromethyl)benzyl]amino]-1,3,5-triazin-2-yl)-L-phenylalanine
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4-(5-[[(1-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl)methyl]amino]pyrazin-2-yl)-L-phenylalanine
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4-(5-[[(1-hydroxynaphthalen-2-yl)methyl]amino]pyrazin-2-yl)-L-phenylalanine
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4-(5-[[(2'-methylbiphenyl-2-yl)methyl]amino]pyrazin-2-yl)-L-phenylalanine
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4-(5-[[(9-ethyl-9H-carbazol-3-yl)methyl]amino]pyrazin-2-yl)-L-phenylalanine
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4-(5-[[3-(cyclopentyloxy)-4-methoxybenzyl]amino]pyrazin-2-yl)-L-phenylalanine
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4-([(E)-amino[([1,1'-biphenyl]-2-yl)amino]methylidene]carbamoyl)-L-phenylalanine
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4-([(E)-amino[([2-(piperidin-1-yl)-6-[(propan-2-yl)oxy]phenyl]methyl)amino]methylidene]carbamoyl)-L-phenylalanine
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4-([(E)-amino[([2-(piperidin-1-yl)-6-[2-(trifluoromethyl)phenoxy]phenyl]methyl)amino]methylidene]carbamoyl)-L-phenylalanine
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4-([(E)-amino[([2-(piperidin-1-yl)-6-[3-(trifluoromethyl)phenoxy]phenyl]methyl)amino]methylidene]carbamoyl)-L-phenylalanine
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4-([(E)-amino[([2-(piperidin-1-yl)-6-[4-(trifluoromethyl)phenoxy]phenyl]methyl)amino]methylidene]carbamoyl)-L-phenylalanine
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4-chloro-L-phenylalanine
4-Chlorophenylalanine
4-ethynylphenylalanine
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4-Fluorotryptophan
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4-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]-6-[4-[(2H-tetrazol-5-yl)amino]piperidin-1-yl]pyrimidin-2-amine
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4-[(diaminomethylidene)carbamoyl]-L-phenylalanine
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4-[4-(methylamino)-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl]-L-phenylalanine
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4-[4-amino-6-(1-naphthalen-2-ylethoxy)-1,3,5-triazin-2-yl]-L-phenylalanine
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4-[4-amino-6-(2,2,2-trifluoro-1-naphthalen-2-ylethoxy)-1,3,5-triazin-2-yl]-L-phenylalanine
4-[4-amino-6-(2,2,2-trifluoro-1-[2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl]ethoxy)-1,3,5-triazin-2-yl]-L-phenylalanine
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4-[4-amino-6-(benzylamino)-1,3,5-triazin-2-yl]-L-phenylalanine
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4-[4-amino-6-([[4'-(trifluoromethyl)biphenyl-4-yl]methyl]amino)-1,3,5-triazin-2-yl]-L-phenylalanine
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4-[4-amino-6-[(1-biphenyl-4-ylethyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
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4-[4-amino-6-[(1-methyl-1-naphthalen-2-ylethyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
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4-[4-amino-6-[(1-naphthalen-2-ylpropyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
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4-[4-amino-6-[(1-tricyclo[3.3.1.1(3,7)]dec-1-ylethyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
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4-[4-amino-6-[(2,2,2-trifluoro-1-naphthalen-2-ylethyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
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4-[4-amino-6-[(2-methyl-1-naphthalen-2-ylpropyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
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4-[4-amino-6-[(3,4-dimethylbenzyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
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4-[4-amino-6-[(3-methyl-1-naphthalen-2-ylbutyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
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4-[4-amino-6-[(4-phenoxybenzyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
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4-[4-amino-6-[(biphenyl-2-ylmethyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
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4-[4-amino-6-[(biphenyl-3-ylmethyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
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4-[4-amino-6-[(biphenyl-4-ylmethyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
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4-[4-amino-6-[(cyclohexylmethyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
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4-[4-amino-6-[(naphthalen-2-ylmethyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
-
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4-[4-amino-6-[2,2,2-trifluoro-1-(2-furan-2-ylphenyl)ethoxy]-1,3,5-triazin-2-yl]-L-phenylalanine
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4-[4-amino-6-[2,2,2-trifluoro-1-(3'-methylbiphenyl-2-yl)ethoxy]-1,3,5-triazin-2-yl]-L-phenylalanine
-
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4-[4-amino-6-[2,2,2-trifluoro-1-(5-furan-2-ylthiophen-2-yl)ethoxy]-1,3,5-triazin-2-yl]-L-phenylalanine
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4-[4-morpholin-4-yl-6-[(naphthalen-2-ylmethyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
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4-[4-[(1-naphthalen-2-ylethyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
-
-
4-[5-[(3,4-dimethoxybenzyl)amino]pyrazin-2-yl]-L-phenylalanine
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4-[5-[(4-cyanobenzyl)amino]pyrazin-2-yl]-L-phenylalanine
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4-[5-[(biphenyl-4-ylmethyl)amino]pyrazin-2-yl]-L-phenylalanine
-
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4-[5-[(cyclohexylmethyl)amino]pyrazin-2-yl]-L-phenylalanine
-
-
4-[5-[(furan-3-ylmethyl)amino]pyrazin-2-yl]-L-phenylalanine
-
-
4-[5-[(pyridin-3-ylmethyl)amino]pyrazin-2-yl]-L-phenylalanine
-
-
4-[5-[(quinolin-3-ylmethyl)amino]pyrazin-2-yl]-L-phenylalanine
-
-
4-[[(E)-amino(benzylamino)methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino([[2-(1H-1,2,4-triazol-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino([[2-(1H-pyrazol-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino([[2-(2-azabicyclo[2.2.1]heptan-2-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
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4-[[(E)-amino([[2-(2-chlorophenoxy)-6-(piperidin-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
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4-[[(E)-amino([[2-(2-methoxyphenoxy)-6-(piperidin-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino([[2-(2-methylphenoxy)-6-(piperidin-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
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-
4-[[(E)-amino([[2-(2-methylpiperidin-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
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4-[[(E)-amino([[2-(2H-1,2,3-triazol-2-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
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4-[[(E)-amino([[2-(3,5-dimethylpiperidin-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino([[2-(3-azabicyclo[3.1.0]hexan-3-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino([[2-(3-chlorophenoxy)-6-(piperidin-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
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4-[[(E)-amino([[2-(3-methoxyphenoxy)-6-(piperidin-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
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4-[[(E)-amino([[2-(3-methyl-1H-pyrazol-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
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4-[[(E)-amino([[2-(3-methylphenoxy)-6-(piperidin-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
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4-[[(E)-amino([[2-(3-methylpiperidin-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
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4-[[(E)-amino([[2-(4-benzylpiperidin-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino([[2-(4-chlorophenoxy)-6-(piperidin-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino([[2-(4-hydroxypiperidin-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino([[2-(4-methoxyphenoxy)-6-(piperidin-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino([[2-(4-methoxypiperidin-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino([[2-(4-methyl-1H-imidazol-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino([[2-(4-methylphenoxy)-6-(piperidin-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino([[2-(4-phenylpiperidin-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino([[2-(azepan-1-yl)-6-methoxyphenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino([[2-(azepan-1-yl)-6-phenoxyphenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino([[2-(azepan-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino([[2-(azetidin-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino([[2-(cyclobutyloxy)-6-(piperidin-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino([[2-(cyclohexyloxy)-6-(piperidin-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino([[2-(diethylamino)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino([[2-(morpholin-4-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino([[2-(piperidin-1-yl)-5-(1,3-thiazol-2-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino([[2-(piperidin-1-yl)-6-(trifluoromethyl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino([[2-(piperidin-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino([[2-(pyrrolidin-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino([[2-(thiomorpholin-4-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino([[2-chloro-6-(piperidin-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino([[2-ethoxy-6-(piperidin-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino([[2-methoxy-6-(piperidin-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino([[2-methyl-6-(piperidin-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino([[2-phenoxy-6-(piperidin-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino([[3-(piperidin-1-yl)[1,1'-biphenyl]-2-yl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino([[3-chloro-2-(piperidin-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino([[3-methoxy-2-(piperidin-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino([[3-methyl-2-(piperidin-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino([[4-(piperidin-1-yl)[1,1'-biphenyl]-3-yl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino([[4-chloro-2-(piperidin-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino([[4-methoxy-2-(piperidin-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino([[4-methyl-2-(piperidin-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino([[5-chloro-2-(piperidin-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino([[5-methoxy-2-(piperidin-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino([[5-methyl-2-(piperidin-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino[[([1,1'-biphenyl]-2-yl)methyl](methyl)amino]methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino[[([1,1'-biphenyl]-2-yl)methyl]amino]methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino[[([1,1'-biphenyl]-3-yl)methyl]amino]methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino[[([1,1'-biphenyl]-4-yl)methyl]amino]methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino[[2-([1,1'-biphenyl]-2-yl)ethyl]amino]methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino[[3-([1,1'-biphenyl]-2-yl)propyl]amino]methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-[[([1,1'-biphenyl]-2-yl)methyl]amino](methylamino)methylidene]carbamoyl]-L-phenylalanine
-
-
5-Fluorotryptophan
-
-
5-hydroxytryptophan
6-Fluorotryptophan
7-(2-amino-6-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]pyrimidin-4-yl)-2,7-diazaspiro[4.4]nonane-3-carboxylic acid
-
-
8-(2-amino-6-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]pyrimidin-4-yl)-1,8-diazaspiro[4.5]decane-2-carboxylic acid
-
-
8-(2-amino-6-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]pyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-3-carboxylic acid
-
-
8-(4-amino-6-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]-1,3,5-triazin-2-yl)-2,8-diazaspiro[4.5]decane-3-carboxylic acid
-
-
8-(4-amino-6-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]pyrimidin-2-yl)-2,8-diazaspiro[4.5]decane-3-carboxylic acid
-
-
8-(5-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]pyridazin-3-yl)-2,8-diazaspiro[4.5]decane-3-carboxylic acid
-
-
8-(5-[(1S)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]pyrazin-2-yl)-2,8-diazaspiro[4.5]decane-3-carboxylic acid
-
-
8-(6-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]-2-hydroxypyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-3-carboxylic acid
-
-
8-(6-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]-2-methylpyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-3-carboxylic acid
-
-
8-(6-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]-2-phenoxypyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-3-carboxylic acid
-
-
8-(6-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]pyrazin-2-yl)-2,8-diazaspiro[4.5]decane-3-carboxylic acid
-
-
8-(6-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]pyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-3-carboxylic acid
-
-
8-hydroxyquinoline
-
-
8-[6-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]-2-(cyclohexylamino)pyrimidin-4-yl]-2,8-diazaspiro[4.5]decane-3-carboxylic acid
-
-
9-(2-amino-6-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]pyrimidin-4-yl)-3,9-diazaspiro[5.5]undecane-2-carboxylic acid
-
-
Aroclor 1254
-
-
citalopram
selective serotonin reuptake inhibitors, like citalopram, exert their activity enhancing the general serotonergic tone, citalopram is the most selective one with little or no affinity for a variety of receptor types, association between gene TPH1 A218C polymorphism and citalopram antidepressant response in a Korean population, overview
Co2+
-
80% inhibition at 0.1 mM
CoCl2
-
1 mM, complete inhibition
D,L-4-chlorophenylalanine
D-Dopa
-
noncompetitive vs. L-tryptophan and (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin
desferrioxamine
-
0.010 mM or higher, irreversible loss of activity
dithiothreitol
-
-
dopamine
ethyl (3S)-8-(2-amino-6-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]pyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-3-carboxylate
-
-
Fe2+
-
-
H2O2
-
complete dependence on catalase in the absence of a mercaptan
Iron chelators
-
L-4-chlorophenylalanine
-
-
L-5-hydroxytryptophan
-
-
L-Dopa
-
noncompetitive vs. L-tryptophan and (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin
L-erythro-7,8-dihydrobiopterin
-
recombinant N-terminal truncated enzyme, competitive vs. (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin
L-p-Chlorophenylalanine
-
-
L-phenylalanine
L-tryptophan
L-tyrosine
-
noncompetitive vs. L-tryptophan and (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin
LP 533,401
-
-
-
LP-533,401
-
-
-
LP-533401
-
-
LP-615819
-
-
LP533401
-
-
-
LX 1033
-
-
-
LX-1033
-
-
-
LX1606
-
-
-
Mn2+
-
50% inhibition at 0.01 mM
N-[1-(2-amino-6-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]pyrimidin-4-yl)-3,5-dimethylpiperidin-4-yl]glycine
-
-
N-[1-(2-amino-6-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]pyrimidin-4-yl)-4-methylpiperidin-4-yl]glycine
-
-
N-[1-(2-amino-6-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]pyrimidin-4-yl)piperidin-4-yl]glycine
-
-
N-[4-(2-amino-6-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]pyrimidin-4-yl)phenyl]methanesulfonamide
-
-
nifedipine
-
reduces the enzyme activity by blocking the Ca2+-influx accompanied with a reduction of 5-hydroxytryptophan, serotonin, N-acetylserotonin and melatonin intracellular content, as well as a reduction of serotonin and melatonin secretion
NVS-TPH120
-
-
-
NVS-TPH146
-
-
-
NVS-TPH176
-
-
-
NVS-TPH180
-
-
-
phenylalanine
-
-
serotonin
-
1 mM, 7.5% inhibition, 10 mM, 70% inhibition
tryptophan
-
substrate inhibition of the catalytic domain of TPH1
ZnSO4
-
1 mM, 80% inhibition
additional information
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
14-3-3 protein
-
activates the phosphorylated TPH2
-
2-mercaptoethanol
2-mercaptoethylamine
-
30 mM, 93.8% activity compared to activation with dithiothreitol
2-mercaptopropionate
-
30 mM, 11.7% activity compared to activation with dithiothreitol
3-Mercaptopropionate
-
30 mM, 22% activity compared to activation with dithiothreitol
CaCl2
-
1 mM, 7% activation
dithiothreitol
Fe(NH4)2(SO4)2
-
-
glutathione
-
30 mM, 16.1% activity compared to activation with dithiothreitol
L-cysteine
N-acetylcysteine
-
30 mM, 31.2% activity compared to activation with dithiothreitol
additional information
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.045
(6R)-5,6,7,8-tetrahydrobiopterin
-
substrate tryptophan
0.0128 - 0.281
(6R)-L-erytho-5,6,7,8-tetrahydrobiopterin
0.01789 - 0.796
(6R)-L-erythro-5,6,7,8-tetrahydrobiopterin
2.1
(7R)-5,6,7,8-tetrahydrobiopterin
-
substrate tryptophan
0.006 - 0.13
2-amino-4-hydroxy-6,7-dimethyl-5,6,7,8-tetrahydropteridine
0.05
2-amino-4-hydroxy-6-methyl-5,6,7,8-tetrahydropteridine
-
-
-
0.055 - 0.125
2-amino-4-hydroxy-6-methyltetrahydropteridine
0.0865
2-azaisotryptophan
-
-
0.262
4-azatryptophan
-
-
0.994
4-methyltryptophan
-
-
0.295
6-azatryptophan
-
-
0.075
6-methyl-5,6,7,8-tetrahydrobiopterin
-
substrate tryptophan
0.053 - 0.802
6-methyl-tetrahydropterin
0.0146 - 0.177
6-methyltetrahydropterin
0.0151
6-methyltryptophan
-
-
0.0662
7-azatryptophan
-
-
0.0375
7-methyltryptophan
-
-
0.022 - 0.102
L-phenylalanine
0.002 - 0.355
L-tryptophan
0.039 - 0.273
O2
0.09 - 0.286
phenylalanine
0.0067 - 0.324
tetrahydrobiopterin
0.05 - 0.29
tryptophan
additional information
additional information
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.217
2-azaisotryptophan
-
-
0.358
4-azatryptophan
-
-
0.273
4-methyltryptophan
-
-
0.533
6-azatryptophan
-
-
0.0733
6-methyltryptophan
-
-
0.252
7-azatryptophan
-
-
0.315
7-methyltryptophan
-
-
0.207 - 32
L-tryptophan
1.383 - 22.8
O2
2.167 - 43
tetrahydrobiopterin
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00082 - 0.0026
1,10-phenanthroline
0.021
D,L-4-chlorophenylalanine
-
-
0.0761 - 0.609
D-Dopa
0.007 - 0.0943
dopamine
0.026
L-4-chlorophenylalanine
-
-
0.035
L-5-hydroxytryptophan
-
-
0.017 - 0.0887
L-Dopa
0.161
L-erythro-7,8-dihydrobiopterin
-
recombinant truncated enzyme
0.0727 - 0.197
L-phenylalanine
0.072 - 0.164
L-tryptophan
0.0162 - 0.306
L-tyrosine
0.15
phenylalanine
-
-
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.02
(2S)-2-amino-5-(2-amino-6-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]pyrimidin-4-yl)pent-4-ynoic acid
Rattus norvegicus
-
pH and temperature not specified in the publication
0.001787
(3R)-8-(2-amino-6-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]pyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-3-carboxylic acid
Rattus norvegicus
-
pH and temperature not specified in the publication
0.000026
(3S)-8-(2-amino-6-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]pyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-3-carboxylic acid
Rattus norvegicus
-
pH and temperature not specified in the publication
0.000871
(3S)-8-(2-amino-6-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]pyrimidin-4-yl)-2-methyl-2,8-diazaspiro[4.5]decane-3-carboxylic acid
Rattus norvegicus
-
pH and temperature not specified in the publication
0.02
2-(2-amino-6-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]pyrimidin-4-yl)-2,6-diazaspiro[3.4]octane-7-carboxylic acid
Rattus norvegicus
-
pH and temperature not specified in the publication
0.000361
3-(2-amino-6-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]pyrimidin-4-yl)-N-(2-methylprop-2-en-1-yl)-3-azabicyclo[3.2.1]octan-8-amine
Rattus norvegicus
-
pH and temperature not specified in the publication
0.011
3-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)phenylalanine
Mus musculus
-
-
0.001019
3-amino-3-[1-(2-amino-6-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]pyrimidin-4-yl)piperidin-4-yl]propanoic acid
Rattus norvegicus
-
pH and temperature not specified in the publication
0.00377
3-amino-3-[4-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)phenyl]propanoic acid
Mus musculus
-
-
0.002149
3-[(3R)-3-(2-amino-6-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]pyrimidin-4-yl)pyrrolidin-1-yl]-L-alanine
Rattus norvegicus
-
pH and temperature not specified in the publication
0.002714
3-[1-(2-amino-6-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]pyrimidin-4-yl)piperidin-4-yl]propanoic acid
Rattus norvegicus
-
pH and temperature not specified in the publication
0.00077
3-[1-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)piperidin-4-yl]alanine
Mus musculus
-
-
0.00622
3-[3-(2-amino-6-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]pyrimidin-4-yl)-3,6-diazabicyclo[3.1.1]heptan-6-yl]-L-alanine
Rattus norvegicus
-
pH and temperature not specified in the publication
0.000096
3-[3-(2-amino-6-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]pyrimidin-4-yl)-3,8-diazabicyclo[3.2.1]octan-8-yl]-L-alanine
Rattus norvegicus
-
pH and temperature not specified in the publication
0.0126
3-[3-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)-1H-pyrazol-1-yl]alanine
Mus musculus
-
-
0.000211
3-[4-(2-amino-6-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]pyrimidin-4-yl)-1,4-diazepan-1-yl]-L-alanine
Rattus norvegicus
-
pH and temperature not specified in the publication
0.00005
3-[4-(2-amino-6-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]pyrimidin-4-yl)piperazin-1-yl]-L-alanine
Rattus norvegicus
-
pH and temperature not specified in the publication
0.000449
3-[5-(2-amino-6-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]pyrimidin-4-yl)-2,5-diazabicyclo[2.2.2]octan-2-yl]-L-alanine
Rattus norvegicus
-
pH and temperature not specified in the publication
0.00089
3-[5-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)pyridin-2-yl]alanine
Mus musculus
-
-
0.004039 - 0.005126
3-[6-(2-amino-6-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]pyrimidin-4-yl)-3,6-diazabicyclo[3.1.1]heptan-3-yl]-L-alanine
0.000519
3-[8-(2-amino-6-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]pyrimidin-4-yl)-3,8-diazabicyclo[3.2.1]octan-3-yl]-L-alanine
Rattus norvegicus
-
pH and temperature not specified in the publication
0.00005
4-(4-amino-6-[methyl[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)-L-phenylalanine
Homo sapiens
-
-
0.0002
4-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)-2-fluorophenylalanine
Mus musculus
-
-
0.0111
4-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)-a-methylphenylalanine
Mus musculus
-
-
0.000026 - 0.000032
4-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)-L-phenylalanine
0.000044
4-(4-amino-6-[[(1S)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)-L-phenylalanine
Homo sapiens
-
-
0.000014
4-(4-amino-6-[[(4'-methylbiphenyl-4-yl)methyl]amino]-1,3,5-triazin-2-yl)-L-phenylalanine
Homo sapiens
-
-
0.00012
4-(4-amino-6-[[4-(trifluoromethyl)benzyl]amino]-1,3,5-triazin-2-yl)-L-phenylalanine
Homo sapiens
-
-
0.000046
4-(5-[[(1-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl)methyl]amino]pyrazin-2-yl)-L-phenylalanine
Mus musculus
-
-
0.000013
4-(5-[[(1-hydroxynaphthalen-2-yl)methyl]amino]pyrazin-2-yl)-L-phenylalanine
Mus musculus
-
-
0.00004
4-(5-[[(2'-methylbiphenyl-2-yl)methyl]amino]pyrazin-2-yl)-L-phenylalanine
Mus musculus
-
-
0.000031
4-(5-[[(9-ethyl-9H-carbazol-3-yl)methyl]amino]pyrazin-2-yl)-L-phenylalanine
Mus musculus
-
-
0.000045
4-(5-[[3-(cyclopentyloxy)-4-methoxybenzyl]amino]pyrazin-2-yl)-L-phenylalanine
Mus musculus
-
-
0.000974
4-([(E)-amino[([1,1'-biphenyl]-2-yl)amino]methylidene]carbamoyl)-L-phenylalanine
Homo sapiens
-
pH and temperature not specified in the publication
0.000028
4-([(E)-amino[([2-(piperidin-1-yl)-6-[(propan-2-yl)oxy]phenyl]methyl)amino]methylidene]carbamoyl)-L-phenylalanine
Homo sapiens
-
pH and temperature not specified in the publication
0.00001
4-([(E)-amino[([2-(piperidin-1-yl)-6-[2-(trifluoromethyl)phenoxy]phenyl]methyl)amino]methylidene]carbamoyl)-L-phenylalanine
Homo sapiens
-
pH and temperature not specified in the publication
0.000014
4-([(E)-amino[([2-(piperidin-1-yl)-6-[3-(trifluoromethyl)phenoxy]phenyl]methyl)amino]methylidene]carbamoyl)-L-phenylalanine
Homo sapiens
-
pH and temperature not specified in the publication
0.000006
4-([(E)-amino[([2-(piperidin-1-yl)-6-[4-(trifluoromethyl)phenoxy]phenyl]methyl)amino]methylidene]carbamoyl)-L-phenylalanine
Homo sapiens
-
pH and temperature not specified in the publication
0.00155 - 0.092
4-Chlorophenylalanine
0.03
4-ethynylphenylalanine
Mus musculus
-
-
0.007552
4-[(1R)-1-[4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl]-2,2,2-trifluoroethoxy]-6-[4-[(2H-tetrazol-5-yl)amino]piperidin-1-yl]pyrimidin-2-amine
Rattus norvegicus
-
pH and temperature not specified in the publication
0.02
4-[(diaminomethylidene)carbamoyl]-L-phenylalanine
Homo sapiens
-
pH and temperature not specified in the publication
0.00061
4-[4-(methylamino)-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl]-L-phenylalanine
Homo sapiens
-
-
0.00038
4-[4-amino-6-(1-naphthalen-2-ylethoxy)-1,3,5-triazin-2-yl]-L-phenylalanine
Mus musculus
-
-
0.00018 - 0.00032
4-[4-amino-6-(2,2,2-trifluoro-1-naphthalen-2-ylethoxy)-1,3,5-triazin-2-yl]-L-phenylalanine