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
-
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
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Metabolic pathways
-
-
serotonin and melatonin biosynthesis
-
-
Tryptophan metabolism
-
-
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
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
a planarian, gene TPH
UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
Mus musculus C57BL/6
C57/BL6 mice
-
-
Manually annotated by BRENDA team
no activity in Rattus norvegicus
PC-12 cells
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
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Uniprot
Manually annotated by BRENDA team
synthetic construct
-
-
-
Manually annotated by BRENDA team
-
-
-
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
-
rate-limiting enzyme in the serotonin biosynthesis
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
-
recombinant N- and C-terminal truncated enzyme
-
?
4-azatryptophan + 6-methyltetrahydropterin + O2
5-hydroxy-4-azatryptophan + 6-methyldihydropterin + H2O
show the reaction diagram
-
recombinant N- and C-terminal truncated enzyme
-
?
4-methyltryptophan + 6-methyltetrahydropterin + O2
5-hydroxy-4-methyltryptophan + 6-methyldihydropterin + H2O
show the reaction diagram
-
recombinant N- and C-terminal truncated enzyme
-
?
5-methyltryptophan + 6-methyltetrahydropterin + O2
5-hydroxymethyltryptophan + 5-hydroxy-4-methyltryptophan + 6-methyldihydropterin + H2O
show the reaction diagram
-
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
-
recombinant N- and C-terminal truncated enzyme
-
?
6-methyltryptophan + 6-methyltetrahydropterin + O2
5-hydroxy-6-methyltryptophan + 6-methyldihydropterin + H2O
show the reaction diagram
-
recombinant N- and C-terminal truncated enzyme
-
?
7-azatryptophan + 6-methyltetrahydropterin + O2
5-hydroxy-7-azatryptophan + 6-methyldihydropterin + H2O
show the reaction diagram
-
recombinant N- and C-terminal truncated enzyme
-
?
7-methyltryptophan + 6-methyltetrahydropterin + O2
5-hydroxy-7-methyltryptophan + 6-methyldihydropterin + H2O
show the reaction diagram
-
recombinant N- and C-terminal truncated enzyme
-
?
L-methionine + ? + O2
?
show the reaction diagram
-
relative high activity with pronase-treated PTMO
-
-
?
L-phenylalanine + tetrahydropteridine + O2
L-tyrosine + dihydropteridine + H2O
show the reaction diagram
-
purified PTMO shows no activity, relative high activity with pronase-treated PTMO
-
-
?
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
-
-
-
-
?
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
?
-
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
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
tetrahydrobiopterin
additional information
-
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
(6R)-5,6,7,8-tetrahydrobiopterin
-
-
(6R)-L-erytho-5,6,7,8-tetrahydrobiopterin
-
TPH2, substrate inhibition
(7R)-5,6,7,8-tetrahydrobiopterin
-
recombinant pinal enzyme, 2.1 mM, 50% inhibition
1,10-phenanthroline
2,2'-dipyridyl
-
-
3,4-dihydroxyphenylalanine
-
-
3,4-Dihydroxyphenylethylamine
-
-
3,4-Dihydroxystyrene
-
-
3,4-methylenedioxymethamphetamine
-
inactivation of the enzyme
3-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)phenylalanine
-
-
3-amino-3-[4-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)phenyl]propanoic acid
-
-
3-[1-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)piperidin-4-yl]alanine
-
-
3-[3-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)-1H-pyrazol-1-yl]alanine
-
-
3-[5-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)pyridin-2-yl]alanine
-
-
4-(4-amino-6-[methyl[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)-L-phenylalanine
-
-
4-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)-2-fluorophenylalanine
-
-
4-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)-a-methylphenylalanine
-
-
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
-
-
4-(4-amino-6-[[(4'-methylbiphenyl-4-yl)methyl]amino]-1,3,5-triazin-2-yl)-L-phenylalanine
-
-
4-(4-amino-6-[[4-(trifluoromethyl)benzyl]amino]-1,3,5-triazin-2-yl)-L-phenylalanine
-
-
4-(5-[[(1-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl)methyl]amino]pyrazin-2-yl)-L-phenylalanine
-
-
4-(5-[[(1-hydroxynaphthalen-2-yl)methyl]amino]pyrazin-2-yl)-L-phenylalanine
-
-
4-(5-[[(2'-methylbiphenyl-2-yl)methyl]amino]pyrazin-2-yl)-L-phenylalanine
-
-
4-(5-[[(9-ethyl-9H-carbazol-3-yl)methyl]amino]pyrazin-2-yl)-L-phenylalanine
-
-
4-(5-[[3-(cyclopentyloxy)-4-methoxybenzyl]amino]pyrazin-2-yl)-L-phenylalanine
-
-
4-chloro-L-phenylalanine
4-Chlorophenylalanine
4-ethynylphenylalanine
-
-
4-Fluorotryptophan
-
-
4-[4-(methylamino)-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl]-L-phenylalanine
-
-
4-[4-amino-6-(1-naphthalen-2-ylethoxy)-1,3,5-triazin-2-yl]-L-phenylalanine
-
-
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
-
-
4-[4-amino-6-(benzylamino)-1,3,5-triazin-2-yl]-L-phenylalanine
-
-
4-[4-amino-6-([[4'-(trifluoromethyl)biphenyl-4-yl]methyl]amino)-1,3,5-triazin-2-yl]-L-phenylalanine
-
-
4-[4-amino-6-[(1-biphenyl-4-ylethyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
-
-
4-[4-amino-6-[(1-methyl-1-naphthalen-2-ylethyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
-
-
4-[4-amino-6-[(1-naphthalen-2-ylpropyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
-
-
4-[4-amino-6-[(1-tricyclo[3.3.1.1(3,7)]dec-1-ylethyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
-
-
4-[4-amino-6-[(2,2,2-trifluoro-1-naphthalen-2-ylethyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
-
-
4-[4-amino-6-[(2-methyl-1-naphthalen-2-ylpropyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
-
-
4-[4-amino-6-[(3,4-dimethylbenzyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
-
-
4-[4-amino-6-[(3-methyl-1-naphthalen-2-ylbutyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
-
-
4-[4-amino-6-[(4-phenoxybenzyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
-
-
4-[4-amino-6-[(biphenyl-2-ylmethyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
-
-
4-[4-amino-6-[(biphenyl-3-ylmethyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
-
-
4-[4-amino-6-[(biphenyl-4-ylmethyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
-
-
4-[4-amino-6-[(cyclohexylmethyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
-
-
4-[4-amino-6-[(naphthalen-2-ylmethyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
-
-
4-[4-amino-6-[2,2,2-trifluoro-1-(2-furan-2-ylphenyl)ethoxy]-1,3,5-triazin-2-yl]-L-phenylalanine
-
-
4-[4-amino-6-[2,2,2-trifluoro-1-(3'-methylbiphenyl-2-yl)ethoxy]-1,3,5-triazin-2-yl]-L-phenylalanine
-
-
4-[4-amino-6-[2,2,2-trifluoro-1-(5-furan-2-ylthiophen-2-yl)ethoxy]-1,3,5-triazin-2-yl]-L-phenylalanine
-
-
4-[4-morpholin-4-yl-6-[(naphthalen-2-ylmethyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
-
-
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
-
-
4-[5-[(4-cyanobenzyl)amino]pyrazin-2-yl]-L-phenylalanine
-
-
4-[5-[(biphenyl-4-ylmethyl)amino]pyrazin-2-yl]-L-phenylalanine
-
-
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
-
-
5-Fluorotryptophan
-
-
5-hydroxytryptophan
6-Fluorotryptophan
8-hydroxyquinoline
-
-
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
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-533401
-
-
LP-615819
-
-
Mn2+
-
50% inhibition at 0.01 mM
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
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
Oryctolagus cuniculus
-
-
0.358
4-azatryptophan
Oryctolagus cuniculus
-
-
0.273
4-methyltryptophan
Oryctolagus cuniculus
-
-
0.533
6-azatryptophan
Oryctolagus cuniculus
-
-
0.0733
6-methyltryptophan
Oryctolagus cuniculus
-
-
0.252
7-azatryptophan
Oryctolagus cuniculus
-
-
0.315
7-methyltryptophan
Oryctolagus cuniculus
-
-
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
0.011
3-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)phenylalanine
Mus musculus
-
-
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
-
-
0.00077
3-[1-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)piperidin-4-yl]alanine
Mus musculus
-
-
0.0126
3-[3-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)-1H-pyrazol-1-yl]alanine
Mus musculus
-
-
0.00089
3-[5-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)pyridin-2-yl]alanine
Mus musculus
-
-
0.00005
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
-
-
0.092
4-Chlorophenylalanine
Mus musculus
-
-
0.03
4-ethynylphenylalanine
Mus musculus
-
-
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
0.000029
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
Mus musculus
-
-
0.0005
4-[4-amino-6-(benzylamino)-1,3,5-triazin-2-yl]-L-phenylalanine
Homo sapiens
-
-
0.00016
4-[4-amino-6-([[4'-(trifluoromethyl)biphenyl-4-yl]methyl]amino)-1,3,5-triazin-2-yl]-L-phenylalanine
Homo sapiens
-
-
0.000024
4-[4-amino-6-[(1-biphenyl-4-ylethyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
Homo sapiens
-
-
0.000055
4-[4-amino-6-[(1-methyl-1-naphthalen-2-ylethyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
Homo sapiens
-
-
0.00015
4-[4-amino-6-[(1-naphthalen-2-ylpropyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
Homo sapiens
-
-
0.000019
4-[4-amino-6-[(1-tricyclo[3.3.1.1(3,7)]dec-1-ylethyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
Homo sapiens
-
-
0.00033
4-[4-amino-6-[(2,2,2-trifluoro-1-naphthalen-2-ylethyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
Homo sapiens
-
-
0.00025
4-[4-amino-6-[(2-methyl-1-naphthalen-2-ylpropyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
Homo sapiens
-
-
0.0001
4-[4-amino-6-[(3,4-dimethylbenzyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
Homo sapiens
-
-
0.00012
4-[4-amino-6-[(3-methyl-1-naphthalen-2-ylbutyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
Homo sapiens
-
-
0.00015
4-[4-amino-6-[(4-phenoxybenzyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
Homo sapiens
-
-
0.000007
4-[4-amino-6-[(biphenyl-2-ylmethyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
Homo sapiens
-
-
0.000038
4-[4-amino-6-[(biphenyl-3-ylmethyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
Homo sapiens
-
-
0.00006
4-[4-amino-6-[(biphenyl-4-ylmethyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
Homo sapiens
-
-
0.00012
4-[4-amino-6-[(cyclohexylmethyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
Homo sapiens
-
-
0.000024
4-[4-amino-6-[(naphthalen-2-ylmethyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
0.00007
4-[4-amino-6-[2,2,2-trifluoro-1-(3'-methylbiphenyl-2-yl)ethoxy]-1,3,5-triazin-2-yl]-L-phenylalanine
Mus musculus
-
-
0.000054
4-[4-amino-6-[2,2,2-trifluoro-1-(5-furan-2-ylthiophen-2-yl)ethoxy]-1,3,5-triazin-2-yl]-L-phenylalanine
Mus musculus
-
-
0.00156
4-[4-morpholin-4-yl-6-[(naphthalen-2-ylmethyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
Homo sapiens
-
-
0.00019
4-[4-[(1-naphthalen-2-ylethyl)amino]-1,3,5-triazin-2-yl]-L-phenylalanine
Homo sapiens
-
-
0.000069
4-[5-[(3,4-dimethoxybenzyl)amino]pyrazin-2-yl]-L-phenylalanine
Mus musculus
-
-
0.00011
4-[5-[(4-cyanobenzyl)amino]pyrazin-2-yl]-L-phenylalanine
Mus musculus
-
-
0.000044
4-[5-[(biphenyl-4-ylmethyl)amino]pyrazin-2-yl]-L-phenylalanine
Mus musculus
-
-
0.00024
4-[5-[(cyclohexylmethyl)amino]pyrazin-2-yl]-L-phenylalanine
Mus musculus
-
-
0.00096
4-[5-[(furan-3-ylmethyl)amino]pyrazin-2-yl]-L-phenylalanine
Mus musculus
-
-
0.00615
4-[5-[(pyridin-3-ylmethyl)amino]pyrazin-2-yl]-L-phenylalanine
Mus musculus
-
-
0.00019
4-[5-[(quinolin-3-ylmethyl)amino]pyrazin-2-yl]-L-phenylalanine
Mus musculus
-
-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.000018
-
enzyme from carconoid tumor
0.000064
recombinant mutant R441H TPH2 in HEK-293 cells
0.00018
-
partially purified enzyme from hindbrain
0.00052
recombinant wild-type TPH2 in HEK-293 cells
0.00165
recombinant mutant P449R TPH2 in HEK-293 cells
0.0021
-
hindbrain enzyme
0.0144
-
purified recombinant enzyme, pH and temperature not specified in the publication
0.0214
-
TPH expressed in Pichia pastoris
0.0271
-
brain tryptophan hydroxylase
0.045
-
brain tryptophan hydroxylase
0.082
-
tryptophan hydroxylase form II
0.17
recombinant His-tagged enzyme
0.235
-
tryptophan hydroxylase from pineal gland
0.296
-
TPH as fusion protein with maltose-binding protein expressed in Escherichia coli
0.434
-
recombinant enzyme, activity in cell extracts
13.3
-
liver enzyme
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.4
-
in the presence of 0.2 mM Fe2+ and 2-mercaptoethanol
6.8
-
in the presence of 0.2 mM Fe2+, without 2-mercaptoethanol
7.4
-
assay at
8 - 8.5
-
soluble enzyme from brain
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6 - 8.7
-
about 50% activity at pH 6.0 and 8.7
6 - 9.5
-
about 50% activity at pH 6 and 9.5
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
high expression of TPH-1; high expression of TPH-2
Manually annotated by BRENDA team
-
dermal
Manually annotated by BRENDA team
-
pituitary cell line
Manually annotated by BRENDA team
low levels of TPH-1; low levels of TPH-2
Manually annotated by BRENDA team
low levels of TPH-2
Manually annotated by BRENDA team
expression of the native truncated mutant TPH2
Manually annotated by BRENDA team
low levels of TPH-2
Manually annotated by BRENDA team
TPH expression pattern during development, TPH expression was found from tailbud stage in the precursor cells of the visceral ganglion and in the tail
Manually annotated by BRENDA team
-
-
Manually annotated by BRENDA team
-
in vivo predominantly localized to normal and malignant melanocytes
Manually annotated by BRENDA team
main expression of gene TPH at commissure axonal connections in the ventral nerve cords
Manually annotated by BRENDA team
low levels of TPH-1; low levels of TPH-2
Manually annotated by BRENDA team
-
expression of TPH2
Manually annotated by BRENDA team
expression of the native truncated mutant TPH2
Manually annotated by BRENDA team
-
raphe cell line
Manually annotated by BRENDA team
-
human small cell lung carcinoma cell line, SHP-77 cells preferentially express TPH1 over TPH2 mRNA
Manually annotated by BRENDA team
-
ventral horn, enzyme expression in muscle after exercise-induced fatigue and control muscle, overview
Manually annotated by BRENDA team
-
TPH1
Manually annotated by BRENDA team
low levels of TPH-1; low levels of TPH-2
Manually annotated by BRENDA team
-
TPH1
Manually annotated by BRENDA team
additional information