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Information on EC 1.14.16.4 - tryptophan 5-monooxygenase
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1.14.16.4 tryptophan 5-monooxygenaseIUBMB Comments
The active centre contains mononuclear iron(II). The enzyme is activated by phosphorylation, catalysed by a Ca2+-activated protein kinase. The 4a-hydroxytetrahydropteridine formed can dehydrate to 6,7-dihydropteridine, both spontaneously and by the action of EC 4.2.1.96, 4a-hydroxytetrahydrobiopterin dehydratase. The 6,7-dihydropteridine must be enzymically reduced back to tetrahydropteridine, by EC 1.5.1.34, 6,7-dihydropteridine reductase, before it slowly rearranges into the more stable but inactive compound 7,8-dihydropteridine.
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Word Map
- 1.14.16.4
- serotonin
-
serotonergic
-
raphe
- 5-hydroxytryptamine
-
monoamine
- dopamine
-
neurotransmitter
-
dorsal
-
anxiety
-
reuptake
- hippocampus
- midbrain
-
antidepressant
-
psychiatric
- 5-hydroxytryptophan
- p-chlorophenylalanine
-
pineal
-
enterochromaffin
-
mood
-
neurotransmission
-
5-hydroxyindoleacetic
- fluoxetine
- hypothalamus
-
neurochemical
- brainstem
- striatum
-
5-hiaa
-
immobility
- tetrahydropterins
- citalopram
- biopterins
-
impulsivity
-
impulsive
-
slc6a4
- methamphetamine
-
antidepressant-like
- 3,4-methylenedioxymethamphetamine
-
5-httlpr
-
oxidase-a
- alpha-methyl-p-tyrosine
- n-acetylserotonin
-
8-oh-dpat
- 5-hydroxyindole
-
monoaminergic
- analysis
-
5,7-dihydroxytryptamine
-
autoreceptors
- medicine
- pargyline
- drug development
- fenfluramine
- carcinoid
- neostriatal
The enzyme appears in viruses and cellular organisms
Reaction Schemes
+
+
=
+
+
+
=
+
a 4a-hydroxy-5,6,7,8-tetrahydropteridine
Synonyms
hTPH2, indoleacetic acid-5-hydroxylase, L-tryptophan 5-hydroxylase, L-tryptophan hydroxylase, oxygenase, tryptophan 5-mono-, peripheral tryptophan hydroxylase, PTMO, putative tryptophan monooxygenase, TH2, TPH, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
indoleacetic acid-5-hydroxylase
-
-
-
-
L-tryptophan hydroxylase
-
-
-
-
oxygenase, tryptophan 5-mono-
-
-
-
-
TPH
TPH-1
TPH-2
TPH1
TPH2
TRpOH
tryptophan 5-hydroxylase
-
-
-
-
tryptophan hydroxylase
tryptophan hydroxylase 1
tryptophan hydroxylase 2
tryptophan hydroxylase type I
tryptophan hydroxylase-1
tryptophan hydroxylase-2
TPH2
-
-
TPH2
-
tryptophan hydroxylase
-
-
-
-
tryptophan hydroxylase 2
-
-
tryptophan hydroxylase 2
-
tryptophan hydroxylase-2
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
L-tryptophan + a 5,6,7,8-tetrahydropteridine + O2 = 5-hydroxy-L-tryptophan + a 4a-hydroxy-5,6,7,8-tetrahydropteridine
L-tryptophan + a 5,6,7,8-tetrahydropteridine + O2 = 5-hydroxy-L-tryptophan + a 4a-hydroxy-5,6,7,8-tetrahydropteridine
hydroxylation regiospecificity
-
L-tryptophan + a 5,6,7,8-tetrahydropteridine + O2 = 5-hydroxy-L-tryptophan + a 4a-hydroxy-5,6,7,8-tetrahydropteridine
phenylalanine hydroxylase, EC 1.14.16.1 also catalyzes this reaction
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L-tryptophan + a 5,6,7,8-tetrahydropteridine + O2 = 5-hydroxy-L-tryptophan + a 4a-hydroxy-5,6,7,8-tetrahydropteridine
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-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
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-
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redox reaction
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reduction
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-
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-
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PATHWAY SOURCE
PATHWAYS
BRENDA
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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-hydroxytetrahydropteridine formed can dehydrate to 6,7-dihydropteridine, both spontaneously and by the action of EC 4.2.1.96, 4a-hydroxytetrahydrobiopterin dehydratase. The 6,7-dihydropteridine must be enzymically reduced back to tetrahydropteridine, by EC 1.5.1.34, 6,7-dihydropteridine reductase, before it slowly rearranges into the more stable but inactive compound 7,8-dihydropteridine.
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CAS REGISTRY NUMBER
COMMENTARY
9037-21-2
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
2-azaisotryptophan + 6-methyltetrahydropterin + O2
5-hydroxy-2-azaisotryptophan + 6-hydroxy-2-azaisotryptophan + 6-methyldihydropterin + H2O
-
recombinant N- and C-terminal truncated enzyme
-
?
4-azatryptophan + 6-methyltetrahydropterin + O2
5-hydroxy-4-azatryptophan + 6-methyldihydropterin + H2O
-
recombinant N- and C-terminal truncated enzyme
-
?
4-methyltryptophan + 6-methyltetrahydropterin + O2
5-hydroxy-4-methyltryptophan + 6-methyldihydropterin + H2O
-
recombinant N- and C-terminal truncated enzyme
-
?
5-methyltryptophan + 6-methyltetrahydropterin + O2
5-hydroxymethyltryptophan + 5-hydroxy-4-methyltryptophan + 6-methyldihydropterin + H2O
-
recombinant N- and C-terminal truncated enzyme
more than 99% 5-hydroxymethyltryptophan
?
6-azatryptophan + 6-methyltetrahydropterin + O2
5-hydroxy-6-azatryptophan + 6-methyldihydropterin + H2O
-
recombinant N- and C-terminal truncated enzyme
-
?
6-methyltryptophan + 6-methyltetrahydropterin + O2
5-hydroxy-6-methyltryptophan + 6-methyldihydropterin + H2O
-
recombinant N- and C-terminal truncated enzyme
-
?
7-azatryptophan + 6-methyltetrahydropterin + O2
5-hydroxy-7-azatryptophan + 6-methyldihydropterin + H2O
-
recombinant N- and C-terminal truncated enzyme
-
?
7-methyltryptophan + 6-methyltetrahydropterin + O2
5-hydroxy-7-methyltryptophan + 6-methyldihydropterin + H2O
-
recombinant N- and C-terminal truncated enzyme
-
?
L-methionine + ? + O2
?
-
relative high activity with pronase-treated PTMO
-
-
?
L-phenylalanine + (7R)-5,6,7,8-tetrahydrobiopterine + O2
L-tyrosine + dihydropteridine + H2O
-
-
-
-
r
L-phenylalanine + tetrahydrobiopteridine + O2
L-tyrosine + dihydropteridine + H2O
-
-
-
-
r
L-phenylalanine + tetrahydropteridine + O2
L-tyrosine + dihydropteridine + H2O
-
purified PTMO shows no activity, relative high activity with pronase-treated PTMO
-
-
?
L-tryptophan + (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan
-
-
-
-
?
L-tryptophan + (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
L-tryptophan + 6-methyl-tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 6-methyl-4a-hydroxytetrahydrobiopterin
L-tryptophan + 6-methyl-tetrahydropterin + O2
5-hydroxy-L-tryptophan + 6-methyl-4a-hydroxytetrahydropterin
-
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
L-phenylalanine + tetrahydropteridine + O2
tyrosine + dihydropteridine + H2O
-
at a comparable rate of L-tryptophan hydroxylation
-
-
?
L-phenylalanine + tetrahydropteridine + O2
tyrosine + dihydropteridine + H2O
-
-
-
-
?
L-phenylalanine + tetrahydropteridine + O2
tyrosine + dihydropteridine + H2O
-
at a comparable rate of L-tryptophan hydroxylation
-
-
?
L-phenylalanine + tetrahydropteridine + O2
tyrosine + dihydropteridine + H2O
-
-
-
?
L-phenylalanine + tetrahydropteridine + O2
tyrosine + dihydropteridine + H2O
-
28.8% of the rate observed with L-tryptophan
-
?
L-phenylalanine + tetrahydropteridine + O2
tyrosine + dihydropteridine + H2O
-
tryptophan hydroxylase form I, 39% of activity with L-tryptophan
-
-
?
L-tryptophan + (6R)-L-erytho-5,6,7,8-tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + ?
-
-
-
-
?
L-tryptophan + (6R)-L-erytho-5,6,7,8-tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + ?
-
-
-
?
L-tryptophan + (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
-
?
L-tryptophan + (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
-
?
L-tryptophan + (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
-
?
L-tryptophan + (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
-
?
L-tryptophan + (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
?
L-tryptophan + (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
-
?
L-tryptophan + (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
over 300 single nucleotide polymorphisms have been identified and are associated with symptoms ranging from mild hyperphenylalaninemia to severe phenylketonuria
-
-
?
L-tryptophan + (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
-
?
L-tryptophan + (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
-
?
L-tryptophan + (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
1.3fold activity compared to the human tryptophan hydroxylase 2
-
-
?
L-tryptophan + 2-amino-4-hydroxy-6,7-dimethyl-5,6,7,8-tetrahydropteridine + O2
?
-
-
-
-
r
L-tryptophan + 2-amino-4-hydroxy-6,7-dimethyl-5,6,7,8-tetrahydropteridine + O2
?
-
-
-
-
r
L-tryptophan + 2-amino-4-hydroxy-6,7-dimethyl-5,6,7,8-tetrahydropteridine + O2
?
-
-
-
-
r
L-tryptophan + 2-amino-4-hydroxy-6-methyl-tetrahydropteridine + O2
?
-
-
-
-
r
L-tryptophan + 2-amino-4-hydroxy-6-methyl-tetrahydropteridine + O2
?
-
-
-
-
r
L-tryptophan + 6-methyl-tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 6-methyl-4a-hydroxytetrahydrobiopterin
-
-
-
-
?
L-tryptophan + 6-methyl-tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 6-methyl-4a-hydroxytetrahydrobiopterin
-
-
-
-
?
L-tryptophan + tetrahydrobiopterin
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
-
?
L-tryptophan + tetrahydrobiopterin
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
rate-limiting enzyme in serotonin synthesis
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
the enzyme is required for serotonin, i.e. 5-hydroxytryptamine, biosynthesis
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
first and rate-determining step in the biosynthesis of the neurotransmitter serotonin
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
brain-specific isozyme TPH2 is the rate-limiting enzyme in serotonin biosynthesis, a truncated enzyme version occurs in brain tissues being the cause of impaired serotonin transmission
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
differences in the regulation of isozyme TPH2 versus isozyme TPH1, overview
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
first and rate limiting step in the biosynthesis of the neurotransmitter serotonin
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
initial and rate-limiting enzyme in the biosynthesis of serotonin
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
low tryptophan levels are associated with depression and may arise because of stress, the hypothalamic and peripheral serotonin, i.e.5-hydroxytryptamine-system has a significant role in appetite regulation, possibly a homeostatic mechanism in regulating peripheral TRP levels, overview
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
rate-limiting step in the biosynthesis of serotonin, regulation of isozymes TPH1 and TPH2, overview
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
rate-limiting step in the synthesis of serotonin
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
the enzyme is rate limiting in serotonin biosynthesis and important in serotonergic neurotransmission, overview
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
the enzyme is rate-limiting in neuronal serotonin biosynthesis, disturbances of the central serotonergic system, due to genetic variations in the TPH2 gene, are involved in the pathophysiology of alcohol dependence and suicidal behavior
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
the enzyme is rate-limiting in serotonin biosynthesis, deficient levels of serotonin are associated with suicide and depression
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
the enzyme is responsible for serotonin biosynthesis
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
TPH catalyzes the first step and rate-limiting reaction in the biosynthesis of 5-hydroxytryptamine, i.e. serotonin, and plays a role in brain development, overview
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
TPH is rate-limiting in serotonin biosynthesis
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
TPH is rate-limiting in serotonin biosynthesis
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
TPH is the rate-limiting enzyme in the biosynthesis of 5-hydroxytryptamine, i.e. serotonin, possible involvement of the TPH1 218A allele in susceptibility to schizophrenia, overview
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
TPH1 is the rate-limiting enzyme in serotonin biosynthesis
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
TPH2 control 5-hydroxytryptamine, i.e. serotonin, biosynthesis and its deficiency is involved in affective disorders, pathophysiological mechanism, overview
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
TPH2 is involved in serotonin biosynthesis, which is involved in behavioural processes, e.g. working memory, overview
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
TPH2 is rate-limiting in serotonin, i.e. 5-hydroxytryptamine, biosynthesis, serotonin is involved in the pathophysiology of several psychiatric disorders including major depression, MD, overview
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
TPH2 is the first and rate-limiting enzyme in the serotonin biosynthetic pathway
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
TPH2 is the rate-limiting enzyme during 5-hydroxytryptamine synthesis in the brain
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
TPH2 is the rate-limiting enzyme in brain serotonin/5-hydroxytryptamine biosynthesis
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
TPH2 is the rate-limiting enzyme in raphe serotonin biosynthesis, and polymorphisms of TPH2 are implicated in vulnerability to psychiatric disorders
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
the enzyme is involved in neuronal serotonin, i.e. 5-hydroxytryptamine, biosynthesis, genetic variance is associated with numerous behavioral traits and psychiatric disorders
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
first and rate-limiting step in serotonin biosynthesis, overview. Serotonin, i.e. 5-hydroxytryptamine, is a neurotransmitter that modulates central and peripheral functions through action on neurons, smooth muscle, and other cell types
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
first and rate-limiting step in serotonin biosynthesis, serotonin, i.e. 5-hydroxytryptamine, is a neurotransmitter with both central and peripheral functions, including the modulation of mood, appetite, hemodynamics, gastrointestinal sensation, secretion, and motility
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
key enzyme of serotonin synthesis in the brain is tryptophan hydroxylase-2
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
rate-limiting enzyme in serotonin biosynthesis, mice deficient in peripheral tryptophan hydroxylase and serotonin exhibit a reduced risk of thrombosis and thromboembolism
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
rate-limiting step in serotonin, i.e. 5-hydroxytryptamine, biosynthesis
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
the enzyme is responsible for serotonin biosynthesis
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
TPH catalyzes the first step and rate-limiting reaction in the biosynthesis of 5-hydroxytryptamine, i.e. serotonin, and plays a role in brain and serotonergic neuron development, also TPH1 is involved in behavioural disorders, overview
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
TPH catalyzes the first step and rate-limiting reaction in the biosynthesis of 5-hydroxytryptamine, i.e. serotonin, and plays a role in brain and serotonergic neuron development, overview
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
TPH is involved in 5-hydroxytryptamine biosynthesis
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
the enzyme is responsible for serotonin biosynthesis
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
TPH2 is a rate-limiting enzyme of neuronal serotonin biosynthesis
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
relative high activity with pronase-treated PTMO
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
isozyme TPH2 is the rate-limiting enzyme in serotonin/5-hydroxytryptamine biosynthesis
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
the calcium influx through L-type high voltage-activated calcium channels is essential for the full activation of tryptophan hydroxylase leading to melatonin synthesis in the pineal gland
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
the enzyme is involved in emotional responses
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
the enzyme is responsible for serotonin biosynthesis
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
TPH is involved in the biosynthesis of 5-hydroxytryptamine, i.e. serotonin, important neurotransmitters in the brain and involved in regulation of body temperature, blood pressure, endocrine activity, appetite, sexual behavior, movement, emesis, and pain, the enzyme activity plays a role in exercise-induced fatigue, overvieww
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
TPH is rate-limiting in serotonin biosynthesis
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
TPH is the rate limiting enzyme in serotonin biosynthesis, the enzyme and 5-hydroxytryptamine might be involved in exercise-induced fatigue
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
TPH2 is the rate-limiting enzyme in 5-hydroxytryptamine, i.e. serotonin, biosynthesis in the brain, and is a candidate for participation in a mechanism mediating the antidepressant effect of selective 5-hydroxytryptamine reuptake inhibitors such as fluoxetine, TPH2 gene expression in the midbrain part of the dorsal raphenucleus is implicated in depression and stress response
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
TPH2 is the rate-limiting enzyme in brain serotonin/5-hydroxytryptamine biosynthesis
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
TPH2 is the rate-limiting enzyme in raphe serotonin biosynthesis
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
r
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
-
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
-
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
-
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
enzyme catalyzes the rate-limiting step in biosynthesis of putative neurotransmitter 5-hydroxytryptamine, serotonin
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
enzyme catalyzes the rate-limiting step in biosynthesis of putative neurotransmitter 5-hydroxytryptamine, serotonin
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
-
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
enzyme catalyzes the rate-limiting step in biosynthesis of putative neurotransmitter 5-hydroxytryptamine, serotonin
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
-
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
enzyme catalyzes the rate-limiting step in biosynthesis of putative neurotransmitter 5-hydroxytryptamine, serotonin
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
-
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
initial and uncommited step in the biosynthesis of melatonin
-
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
rate-determining step of serotonin biosynthesis
-
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
rate-limiting step in biosynthesis of serotonin in brain
-
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
ovarian steroids stimulate TPH-2 mRNA expression, which can in turn cause an increase in serotonin synthesis
-
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
-
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
-
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
cofactor 2-amino-4-hydroxy-6,7-dimethyltetrahydropteridine
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
believed to be the rate-limeting enzyme in the biosynthesis of serotonin in the central nervous system
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
tryptophan hydroxylase-2 controls brain serotonin synthesis
-
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
-
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
-
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
-
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
-
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
cofactor tetrahydrobiopterin
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
cofactor tetrahydrobiopterin
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
cofactor 2-amino-4-hydroxy-6,7-dimethyltetrahydropteridine
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
cofactor 2-amino-4-hydroxy-6,7-dimethyltetrahydropteridine
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
cofactor 2-amino-4-hydroxy-6-methyltetrahydropteridine
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
cofactor 2-amino-4-hydroxy-6-methyltetrahydropteridine
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
enzyme catalyzes the rate-limiting step in biosynthesis of putative neurotransmitter 5-hydroxytryptamine, serotonin
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
-
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
-
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
-
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
-
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
-
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
-
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
cofactor 2-amino-4-hydroxy-6-methyltetrahydropteridine
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
enzyme catalyzes the rate-limiting step in biosynthesis of putative neurotransmitter 5-hydroxytryptamine, serotonin
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
enzyme catalyzes the rate-limiting step in biosynthesis of putative neurotransmitter 5-hydroxytryptamine, serotonin
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
enzyme catalyzes the rate-limiting step in biosynthesis of putative neurotransmitter 5-hydroxytryptamine, serotonin
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
rate-limiting enzyme in synthesis of 5-hydroxy-L-tryptophan
-
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
-
-
?
L-tyrosine + tetrahydropteridine + O2
?
-
1% of activity with L-tryptophan
-
-
?
L-tyrosine + tetrahydropteridine + O2
?
-
relative high activity with pronase-treated PTMO
-
-
?
additional information
?
-
5-hydroxytryptamine is a major modulator of behavior in vertebrates and invertebrates, and deficiencies in the serotonergic system account for several behavioral disorders in humans, 5-hydroxyytryptamine is a major therapeutic target in patients with psychiatric disorders, overview
-
-
?
additional information
?
-
5-hydroxytryptamine is a major modulator of behavior in vertebrates and invertebrates, and deficiencies in the serotonergic system account for several behavioral disorders in humans, 5-hydroxyytryptamine is a major therapeutic target in patients with psychiatric disorders, overview
-
-
?
additional information
?
-
5-hydroxytryptamine is a major modulator of behavior in vertebrates and invertebrates, and deficiencies in the serotonergic system account for several behavioral disorders in humans, 5-hydroxyytryptamine is a major therapeutic target in patients with psychiatric disorders, overview, association of TPH1 with suicidal behavior, TPH1 is involved in brain and serotonergic neuron development, overview
-
-
?
additional information
?
-
5-hydroxytryptamine is a major modulator of behavior in vertebrates and invertebrates, and deficiencies in the serotonergic system account for several behavioral disorders in humans, 5-hydroxyytryptamine is a major therapeutic target in patients with psychiatric disorders, overview, association of TPH1 with suicidal behavior, TPH1 is involved in brain and serotonergic neuron development, overview
-
-
?
additional information
?
-
additive effects of serotonin transporter and tryptophan hydroxylase-2 gene variation on neural correlates of affective processing, serotonergic regulation of neural processing of affective stimuli with the striatum as a critical site where gene-gene regulation takes place, whole brain analysis for emotional word Stroop task, overview
-
-
?
additional information
?
-
alcohol consumption may influence TPH1 and TPH2 expression and regulation
-
-
?
additional information
?
-
association between the tryptophan hydroxylase-1 gene A218C polymorphism and citalopram antidepressant response in a Korean population with major depressive disorder
-
-
?
additional information
?
-
-
association between the tryptophan hydroxylase-1 gene A218C polymorphism and citalopram antidepressant response in a Korean population with major depressive disorder
-
-
?
additional information
?
-
localized changes in TPH2 expression in specific subnuclei of the dorsal raphe nucleus suggest that the serotonergic compensatory mechanism in depression and suicide is specifically regulated within the DRN and has implications for regions innervated by this subnucleus, overview
-
-
?
additional information
?
-
-
the borderline personality disorder might be partly due to serotonergic dysfunction
-
-
?
additional information
?
-
TPH2 expression is part of the developmental program regulated by REST, i.e. the RE-1 silencer of transcription, REST/NRSF is implicated in neurogenesis and transcriptionally regulates a network of genes, overview
-
-
?
additional information
?
-
-
TPH2 expression is part of the developmental program regulated by REST, i.e. the RE-1 silencer of transcription, REST/NRSF is implicated in neurogenesis and transcriptionally regulates a network of genes, overview
-
-
?
additional information
?
-
TPH2 gene and its 5' upstream region variants may be involved in the predisposition to suicide in major depression disorder, however, may not play a role in impulsive-aggressive behaviors as mediators, overview
-
-
?
additional information
?
-
-
TPH2 gene and its 5' upstream region variants may be involved in the predisposition to suicide in major depression disorder, however, may not play a role in impulsive-aggressive behaviors as mediators, overview
-
-
?
additional information
?
-
residue lying adjacent to substrate is F313, role of F313 in substrate specificity, residue is different from L-phenylalanine 4-hydroxylase
-
-
?
additional information
?
-
-
emotional behavior and expression pattern tryptophan hydroxylase is altered in senescence-accelerated prone mouse 6, which show increased serotonin levels, overview
-
-
?
additional information
?
-
temporal expression pattern of TPH1 and pathway regulation, overview
-
-
?
additional information
?
-
temporal expression pattern of TPH1 and pathway regulation, overview
-
-
?
additional information
?
-
temporal expression pattern of TPH2 and pathway regulation, overview
-
-
?
additional information
?
-
temporal expression pattern of TPH2 and pathway regulation, overview
-
-
?
additional information
?
-
-
pronase-treated PTMO shows less than 5% activity of that of L-phenylalanine for L-lysine, L-histidine and L-threonine
-
-
?
additional information
?
-
-
chronic treatment with milnacipran or fluvoxamine is effective to improve both the hyperemotional behavior and the loss of TPH-positive cells in olfactory bulbectomized rats, overview
-
-
?
additional information
?
-
the enzyme expression in brain is correlated to glucocorticoid fluctuations, e.g. corticosterone, overview
-
-
?
additional information
?
-
TPH2 expression is part of the developmental program regulated by REST, i.e. the RE-1 silencer of transcription, REST/NRSF is implicated in neurogenesis and transcriptionally regulates a network of genes, overview
-
-
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
L-tryptophan + (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
L-tryptophan + (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
-
?
L-tryptophan + (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
-
?
L-tryptophan + (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
-
?
L-tryptophan + (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
over 300 single nucleotide polymorphisms have been identified and are associated with symptoms ranging from mild hyperphenylalaninemia to severe phenylketonuria
-
-
?
L-tryptophan + (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
-
?
L-tryptophan + (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
rate-limiting enzyme in serotonin synthesis
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
the enzyme is required for serotonin, i.e. 5-hydroxytryptamine, biosynthesis
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
first and rate-determining step in the biosynthesis of the neurotransmitter serotonin
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
brain-specific isozyme TPH2 is the rate-limiting enzyme in serotonin biosynthesis, a truncated enzyme version occurs in brain tissues being the cause of impaired serotonin transmission
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
differences in the regulation of isozyme TPH2 versus isozyme TPH1, overview
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
first and rate limiting step in the biosynthesis of the neurotransmitter serotonin
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
initial and rate-limiting enzyme in the biosynthesis of serotonin
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
low tryptophan levels are associated with depression and may arise because of stress, the hypothalamic and peripheral serotonin, i.e.5-hydroxytryptamine-system has a significant role in appetite regulation, possibly a homeostatic mechanism in regulating peripheral TRP levels, overview
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
rate-limiting step in the biosynthesis of serotonin, regulation of isozymes TPH1 and TPH2, overview
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
rate-limiting step in the synthesis of serotonin
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
the enzyme is rate limiting in serotonin biosynthesis and important in serotonergic neurotransmission, overview
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
the enzyme is rate-limiting in neuronal serotonin biosynthesis, disturbances of the central serotonergic system, due to genetic variations in the TPH2 gene, are involved in the pathophysiology of alcohol dependence and suicidal behavior
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
the enzyme is rate-limiting in serotonin biosynthesis, deficient levels of serotonin are associated with suicide and depression
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
the enzyme is responsible for serotonin biosynthesis
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
TPH catalyzes the first step and rate-limiting reaction in the biosynthesis of 5-hydroxytryptamine, i.e. serotonin, and plays a role in brain development, overview
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
TPH is rate-limiting in serotonin biosynthesis
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
TPH is rate-limiting in serotonin biosynthesis
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
TPH is the rate-limiting enzyme in the biosynthesis of 5-hydroxytryptamine, i.e. serotonin, possible involvement of the TPH1 218A allele in susceptibility to schizophrenia, overview
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
TPH1 is the rate-limiting enzyme in serotonin biosynthesis
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
TPH2 control 5-hydroxytryptamine, i.e. serotonin, biosynthesis and its deficiency is involved in affective disorders, pathophysiological mechanism, overview
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
TPH2 is involved in serotonin biosynthesis, which is involved in behavioural processes, e.g. working memory, overview
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
TPH2 is rate-limiting in serotonin, i.e. 5-hydroxytryptamine, biosynthesis, serotonin is involved in the pathophysiology of several psychiatric disorders including major depression, MD, overview
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
TPH2 is the first and rate-limiting enzyme in the serotonin biosynthetic pathway
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
TPH2 is the rate-limiting enzyme during 5-hydroxytryptamine synthesis in the brain
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
TPH2 is the rate-limiting enzyme in brain serotonin/5-hydroxytryptamine biosynthesis
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
TPH2 is the rate-limiting enzyme in raphe serotonin biosynthesis, and polymorphisms of TPH2 are implicated in vulnerability to psychiatric disorders
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
the enzyme is involved in neuronal serotonin, i.e. 5-hydroxytryptamine, biosynthesis, genetic variance is associated with numerous behavioral traits and psychiatric disorders
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
first and rate-limiting step in serotonin biosynthesis, overview. Serotonin, i.e. 5-hydroxytryptamine, is a neurotransmitter that modulates central and peripheral functions through action on neurons, smooth muscle, and other cell types
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
first and rate-limiting step in serotonin biosynthesis, serotonin, i.e. 5-hydroxytryptamine, is a neurotransmitter with both central and peripheral functions, including the modulation of mood, appetite, hemodynamics, gastrointestinal sensation, secretion, and motility
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
key enzyme of serotonin synthesis in the brain is tryptophan hydroxylase-2
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
rate-limiting enzyme in serotonin biosynthesis, mice deficient in peripheral tryptophan hydroxylase and serotonin exhibit a reduced risk of thrombosis and thromboembolism
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
rate-limiting step in serotonin, i.e. 5-hydroxytryptamine, biosynthesis
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
the enzyme is responsible for serotonin biosynthesis
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
TPH catalyzes the first step and rate-limiting reaction in the biosynthesis of 5-hydroxytryptamine, i.e. serotonin, and plays a role in brain and serotonergic neuron development, also TPH1 is involved in behavioural disorders, overview
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
TPH catalyzes the first step and rate-limiting reaction in the biosynthesis of 5-hydroxytryptamine, i.e. serotonin, and plays a role in brain and serotonergic neuron development, overview
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
TPH is involved in 5-hydroxytryptamine biosynthesis
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
the enzyme is responsible for serotonin biosynthesis
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
TPH2 is a rate-limiting enzyme of neuronal serotonin biosynthesis
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
isozyme TPH2 is the rate-limiting enzyme in serotonin/5-hydroxytryptamine biosynthesis
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
the calcium influx through L-type high voltage-activated calcium channels is essential for the full activation of tryptophan hydroxylase leading to melatonin synthesis in the pineal gland
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
the enzyme is involved in emotional responses
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
the enzyme is responsible for serotonin biosynthesis
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
TPH is involved in the biosynthesis of 5-hydroxytryptamine, i.e. serotonin, important neurotransmitters in the brain and involved in regulation of body temperature, blood pressure, endocrine activity, appetite, sexual behavior, movement, emesis, and pain, the enzyme activity plays a role in exercise-induced fatigue, overvieww
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
TPH is rate-limiting in serotonin biosynthesis
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
TPH is the rate limiting enzyme in serotonin biosynthesis, the enzyme and 5-hydroxytryptamine might be involved in exercise-induced fatigue
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
TPH2 is the rate-limiting enzyme in 5-hydroxytryptamine, i.e. serotonin, biosynthesis in the brain, and is a candidate for participation in a mechanism mediating the antidepressant effect of selective 5-hydroxytryptamine reuptake inhibitors such as fluoxetine, TPH2 gene expression in the midbrain part of the dorsal raphenucleus is implicated in depression and stress response
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
TPH2 is the rate-limiting enzyme in brain serotonin/5-hydroxytryptamine biosynthesis
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
TPH2 is the rate-limiting enzyme in raphe serotonin biosynthesis
-
-
?
L-tryptophan + tetrahydrobiopterin + O2
5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
-
-
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
enzyme catalyzes the rate-limiting step in biosynthesis of putative neurotransmitter 5-hydroxytryptamine, serotonin
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
enzyme catalyzes the rate-limiting step in biosynthesis of putative neurotransmitter 5-hydroxytryptamine, serotonin
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
enzyme catalyzes the rate-limiting step in biosynthesis of putative neurotransmitter 5-hydroxytryptamine, serotonin
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
enzyme catalyzes the rate-limiting step in biosynthesis of putative neurotransmitter 5-hydroxytryptamine, serotonin
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
initial and uncommited step in the biosynthesis of melatonin
-
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
rate-determining step of serotonin biosynthesis
-
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
rate-limiting step in biosynthesis of serotonin in brain
-
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
ovarian steroids stimulate TPH-2 mRNA expression, which can in turn cause an increase in serotonin synthesis
-
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
believed to be the rate-limeting enzyme in the biosynthesis of serotonin in the central nervous system
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
tryptophan hydroxylase-2 controls brain serotonin synthesis
-
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
enzyme catalyzes the rate-limiting step in biosynthesis of putative neurotransmitter 5-hydroxytryptamine, serotonin
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
enzyme catalyzes the rate-limiting step in biosynthesis of putative neurotransmitter 5-hydroxytryptamine, serotonin
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
enzyme catalyzes the rate-limiting step in biosynthesis of putative neurotransmitter 5-hydroxytryptamine, serotonin
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
enzyme catalyzes the rate-limiting step in biosynthesis of putative neurotransmitter 5-hydroxytryptamine, serotonin
-
?
L-tryptophan + tetrahydropteridine + O2
5-hydroxy-L-tryptophan + dihydropteridine + H2O
-
rate-limiting enzyme in synthesis of 5-hydroxy-L-tryptophan
-
-
?
additional information
?
-
5-hydroxytryptamine is a major modulator of behavior in vertebrates and invertebrates, and deficiencies in the serotonergic system account for several behavioral disorders in humans, 5-hydroxyytryptamine is a major therapeutic target in patients with psychiatric disorders, overview
-
-
?
additional information
?
-
5-hydroxytryptamine is a major modulator of behavior in vertebrates and invertebrates, and deficiencies in the serotonergic system account for several behavioral disorders in humans, 5-hydroxyytryptamine is a major therapeutic target in patients with psychiatric disorders, overview
-
-
?
additional information
?
-
5-hydroxytryptamine is a major modulator of behavior in vertebrates and invertebrates, and deficiencies in the serotonergic system account for several behavioral disorders in humans, 5-hydroxyytryptamine is a major therapeutic target in patients with psychiatric disorders, overview, association of TPH1 with suicidal behavior, TPH1 is involved in brain and serotonergic neuron development, overview
-
-
?
additional information
?
-
5-hydroxytryptamine is a major modulator of behavior in vertebrates and invertebrates, and deficiencies in the serotonergic system account for several behavioral disorders in humans, 5-hydroxyytryptamine is a major therapeutic target in patients with psychiatric disorders, overview, association of TPH1 with suicidal behavior, TPH1 is involved in brain and serotonergic neuron development, overview
-
-
?
additional information
?
-
additive effects of serotonin transporter and tryptophan hydroxylase-2 gene variation on neural correlates of affective processing, serotonergic regulation of neural processing of affective stimuli with the striatum as a critical site where gene-gene regulation takes place, whole brain analysis for emotional word Stroop task, overview
-
-
?
additional information
?
-
alcohol consumption may influence TPH1 and TPH2 expression and regulation
-
-
?
additional information
?
-
association between the tryptophan hydroxylase-1 gene A218C polymorphism and citalopram antidepressant response in a Korean population with major depressive disorder
-
-
?
additional information
?
-
-
association between the tryptophan hydroxylase-1 gene A218C polymorphism and citalopram antidepressant response in a Korean population with major depressive disorder
-
-
?
additional information
?
-
localized changes in TPH2 expression in specific subnuclei of the dorsal raphe nucleus suggest that the serotonergic compensatory mechanism in depression and suicide is specifically regulated within the DRN and has implications for regions innervated by this subnucleus, overview
-
-
?
additional information
?
-
-
the borderline personality disorder might be partly due to serotonergic dysfunction
-
-
?
additional information
?
-
TPH2 expression is part of the developmental program regulated by REST, i.e. the RE-1 silencer of transcription, REST/NRSF is implicated in neurogenesis and transcriptionally regulates a network of genes, overview
-
-
?
additional information
?
-
-
TPH2 expression is part of the developmental program regulated by REST, i.e. the RE-1 silencer of transcription, REST/NRSF is implicated in neurogenesis and transcriptionally regulates a network of genes, overview
-
-
?
additional information
?
-
TPH2 gene and its 5' upstream region variants may be involved in the predisposition to suicide in major depression disorder, however, may not play a role in impulsive-aggressive behaviors as mediators, overview
-
-
?
additional information
?
-
-
TPH2 gene and its 5' upstream region variants may be involved in the predisposition to suicide in major depression disorder, however, may not play a role in impulsive-aggressive behaviors as mediators, overview
-
-
?
additional information
?
-
-
emotional behavior and expression pattern tryptophan hydroxylase is altered in senescence-accelerated prone mouse 6, which show increased serotonin levels, overview
-
-
?
additional information
?
-
temporal expression pattern of TPH1 and pathway regulation, overview
-
-
?
additional information
?
-
temporal expression pattern of TPH1 and pathway regulation, overview
-
-
?
additional information
?
-
temporal expression pattern of TPH2 and pathway regulation, overview
-
-
?
additional information
?
-
temporal expression pattern of TPH2 and pathway regulation, overview
-
-
?
additional information
?
-
-
chronic treatment with milnacipran or fluvoxamine is effective to improve both the hyperemotional behavior and the loss of TPH-positive cells in olfactory bulbectomized rats, overview
-
-
?
additional information
?
-
the enzyme expression in brain is correlated to glucocorticoid fluctuations, e.g. corticosterone, overview
-
-
?
additional information
?
-
TPH2 expression is part of the developmental program regulated by REST, i.e. the RE-1 silencer of transcription, REST/NRSF is implicated in neurogenesis and transcriptionally regulates a network of genes, overview
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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
LITERATURE
Ca2+
Fe2+
Ca2+
-
the calcium influx through L-type high voltage-activated calcium channels is essential for the full activation of tryptophan hydroxylase leading to melatonin synthesis in the pineal gland
Fe2+
the iron coordination is a distorted trigonal bipyramidal coordination with His273, His278, and Glu318 (partially bidentate) and one imidazole as ligands. The tryptophan stacks against Pro269 with a distance of 3.9 A between the iron and the tryptophan Czeta3 atom that is hydroxylated
Fe2+
-
Fe2+ concentration for half-maximal activation of recombinant N-terminal truncated enzyme: 0.0013 mM
Fe2+
-
N- and C-terminal recombinant enzyme, iron is required for activity
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
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
-
-
(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
-
-
(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
-
-
(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
-
-
(7R)-5,6,7,8-tetrahydrobiopterin
-
recombinant pinal enzyme, 2.1 mM, 50% inhibition
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
-
-
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
-
-
3-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)phenylalanine
-
-
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
-
-
3-amino-3-[4-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)phenyl]propanoic acid
-
-
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
-
-
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
-
-
3-[1-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)piperidin-4-yl]alanine
-
-
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
-
-
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
-
-
3-[3-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)-1H-pyrazol-1-yl]alanine
-
-
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
-
-
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
-
-
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
-
-
3-[5-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)pyridin-2-yl]alanine
-
-
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
-
-
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
-
-
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-[[(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-[[3-(cyclopentyloxy)-4-methoxybenzyl]amino]pyrazin-2-yl)-L-phenylalanine
-
-
4-([(E)-amino[([1,1'-biphenyl]-2-yl)amino]methylidene]carbamoyl)-L-phenylalanine
-
-
4-([(E)-amino[([2-(piperidin-1-yl)-6-[(propan-2-yl)oxy]phenyl]methyl)amino]methylidene]carbamoyl)-L-phenylalanine
-
-
4-([(E)-amino[([2-(piperidin-1-yl)-6-[2-(trifluoromethyl)phenoxy]phenyl]methyl)amino]methylidene]carbamoyl)-L-phenylalanine
-
-
4-([(E)-amino[([2-(piperidin-1-yl)-6-[3-(trifluoromethyl)phenoxy]phenyl]methyl)amino]methylidene]carbamoyl)-L-phenylalanine
-
-
4-([(E)-amino[([2-(piperidin-1-yl)-6-[4-(trifluoromethyl)phenoxy]phenyl]methyl)amino]methylidene]carbamoyl)-L-phenylalanine
-
-
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
-
-
4-[4-(methylamino)-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-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-([[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-[[(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
-
-
4-[[(E)-amino([[2-(2-chlorophenoxy)-6-(piperidin-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
-
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
-
-
4-[[(E)-amino([[2-(2-methylpiperidin-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino([[2-(2H-1,2,3-triazol-2-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
-
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
-
-
4-[[(E)-amino([[2-(3-methoxyphenoxy)-6-(piperidin-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino([[2-(3-methyl-1H-pyrazol-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino([[2-(3-methylphenoxy)-6-(piperidin-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
-
4-[[(E)-amino([[2-(3-methylpiperidin-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
-
-
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
-
-
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-[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
-
-
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
D-Dopa
-
noncompetitive vs. L-tryptophan and (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin
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
-
-
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-tyrosine
-
noncompetitive vs. L-tryptophan and (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin
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
4-(4-amino-6-[[(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)-L-phenylalanine
-
-
4-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)-L-phenylalanine
-
substituted 3-(4-(1,3,5-triazin-2-yl)-phenyl)-2-aminopropanoic acid, which can selectively reduce serotonin levels in the intestine without affecting levels in the brain. It can selectively inhibit peripheral 5-HT synthesis without effects on the central nervous system because of very poor systemic exposure and the inability to cross the blood-brain barrier
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-naphthalen-2-ylethoxy)-1,3,5-triazin-2-yl]-L-phenylalanine
-
-
dopamine
-
noncompetitive vs. L-tryptophan and (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin
L-phenylalanine
-
substrate inhibition with tetrahydrobiopterin as cofactor, above 0.5 mM
L-tryptophan
-
substrate inhibition with 2-amino-4-hydroxy-6-methyl-5,6,7,8-tetrahydropteridine, not with 2-amino-4-hydroxy-6,7-dimethyl-5,6,7,8-tetrahydropteridine, above 0.2 mM
additional information
-
no substrate inhibition by (6R)-L-erytho-5,6,7,8-tetrahydrobiopterin
-
additional information
-
removal of 44 amino acids from the N-terminus of TPH2 results in a 3-4fold increased Vmax, which indicates a strong inhibitory function of this part on the enzymes activity
-
additional information
glucocorticoids inhibits TPH2 expression, the suppression is blocked by mifepristone, i.e. RU-486
-
additional information
-
glucocorticoids inhibits TPH2 expression, the suppression is blocked by mifepristone, i.e. RU-486
-
additional information
-
development and pharmacokinetic and pharmacodynamic effects of inhibitors inhibiting specifically the enzyme in the gastrointestinal tract, inhibitory potency on different genotypes, overview
-
additional information
-
development of antithrombotic miniribozymes that target peripheral tryptophan hydroxylase, overview
-
additional information
-
glucocorticoids inhibits TPH2 expression, the suppression is blocked by mifepristone, i.e. RU-486
-
additional information
-
oxidation inhibits activity and leads to the formation of high molecular weight aggregates in a dithiothreitol-reversible manner, only cysteine-less mutants are resistant to this effect
-
additional information
glucocorticoids inhibits TPH2 expression, the suppression is blocked by mifepristone, i.e. RU-486
-
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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
N-acetylcysteine
-
30 mM, 31.2% activity compared to activation with dithiothreitol
2-mercaptoethanol
-
30 mM, 79.3% activity compared to activation with dithiothreitol
dithiothreitol
-
or other sulfhydryl reagents like 2-mercaptoethanol and L-cysteine are essential for activation, 5fold increase in activity
additional information
phosphorylation at Ser19 by protein kinase A or Ca2+/calmodulin dependent protein kinase II activates TPH2 by about 30%, high-affinity binding of purified PKA-phosphorylated TPH2 bound to the 14-3-3 proteins gamma , epsilon and BMH1 causes further increased enzyme activity, overview
-
additional information
-
phosphorylation at Ser19 by protein kinase A or Ca2+/calmodulin dependent protein kinase II activates TPH2 by about 30%, high-affinity binding of purified PKA-phosphorylated TPH2 bound to the 14-3-3 proteins gamma , epsilon and BMH1 causes further increased enzyme activity, overview
-
additional information
-
phosphorylation of TPH2 at Ser19 within the regulatory domain of the enzyme by calmodulin-dependent protein kinase II activates the enzyme
-
additional information
-
citalopram raises basal extracellular serotonin levels in DBA/2J, DBA/2N and BALB/c mice carrying the 1473G allele, but not in C57BL/6J and C57BL/6N mice carrying the 1473C allele, overview
-
additional information
-
enzyme expression and activity are increased in hypoxic rats, the effect is partially reversed by 4-chlorophenylalanine and is reduced in TPH1-deficient rats, overview
-
additional information
-
senescence-accelerated prone mouse 6 show increased serotonin levels, probably due to phosphorylation at Ser58, overview
-
additional information
-
pronase is most effective for activation. Trypsin, chymotrypsin, V8 protease and lysylendoprotease also activate PTMO, but the activity obtained using these proteases is only 5% of that with pronase
-
additional information
-
Acanthopanax senticosus, as aqueous extracts from fresh stem braks, increases the time to exhaustion by treadmill running and it suppressed the exercise-induced increase of 5-hydroxytryptamine synthesis and TPH expression. Acanthopanax senticosus is effective as caffeine for increasing the exhaustion time in treadmill running and for reducing the exercise-induced increase of 5-hydroxytryptamine synthesis and TPH expression in the dorsal raphe, overview
-
additional information
-
administration of 3,4-methylenedioxymethamphetamine to rats induces TPH1, but affects serotonin biosynthesis and TPH enzyme activity in dorsal raphe nuclei, and it decreases SERT binding sites in the striatum, nucleus accumbens and cingulate cortex demonstrating a loss of 5-hydroxytryptamine terminals, overview
-
additional information
fluoxetine treatment for 4 and 8 weeks significantly increases basal TPH2 mRNA levels in the midbrain, correlated with the appearance of antidepressant-like effects in the forced swim test, co-induction of TPH2 and the 5-hydroxytryptamine transporter expression, overview
-
additional information
-
in differentiated RN46A cells, the TPH2 promoter is induced 2.5fold by ionomycin, similar to its action on TPH2 RNA. By contrast, ionomycin has no effect onTPH2 promoter activity in GH4C1 cells or TPH2-negative L6 myoblasts, overview
-
additional information
-
the calcium influx through L-type high voltage-activated calcium channels is essential for the full activation of tryptophan hydroxylase leading to melatonin synthesis in the pineal gland
-
additional information
TPH2 is upregulated by dominant-negative RE-1 silencer of transcription, minimum of 4.4fold relative to hypoxanthine-guanine phosphoribosyltransferase, overview
-
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0128
(6R)-L-erytho-5,6,7,8-tetrahydrobiopterin
-
TPH2 fusion protein with maltose-binding protein
0.0265
(6R)-L-erytho-5,6,7,8-tetrahydrobiopterin
doubly truncated enzyme form DELTANH102-DELTACOOH402
0.027
(6R)-L-erytho-5,6,7,8-tetrahydrobiopterin
-
TPH as fusion protein with maltose-binding protein expressed in Escherichia coli
0.027
(6R)-L-erytho-5,6,7,8-tetrahydrobiopterin
-
TPH1 fusion protein with maltose-binding protein
0.039
(6R)-L-erytho-5,6,7,8-tetrahydrobiopterin
-
TPH expressed in Pichia pastoris
0.146
(6R)-L-erytho-5,6,7,8-tetrahydrobiopterin
-
TPH1, in vitro transcription and translation product
0.281
(6R)-L-erytho-5,6,7,8-tetrahydrobiopterin
-
TPH2, in vitro transcription and translation product
0.0344
(6R)-L-erythro-5,6,7,8-tetrahydrobiopterin
-
biphasic kinetic, low Km value
0.796
(6R)-L-erythro-5,6,7,8-tetrahydrobiopterin
-
biphasic kinetic, high Km value
0.006
2-amino-4-hydroxy-6,7-dimethyl-5,6,7,8-tetrahydropteridine
-
soluble enzyme from brain
0.055
2-amino-4-hydroxy-6-methyltetrahydropteridine
-
substrate L-tryptophan
0.125
2-amino-4-hydroxy-6-methyltetrahydropteridine
-
tryptohan hydroxylase form I
0.0146
6-methyltetrahydropterin
-
recombinant N- and C-terminal truncated enzyme, substrate phenylalanine
0.177
6-methyltetrahydropterin
-
recombinant N- and C-terminal truncated enzyme, substrate tryptophan
0.0606
L-phenylalanine
-
recombinant N- and C-terminal truncated enzyme, cofactor tetrahydrobiopterin
0.1
L-phenylalanine
-
cofactor 2-amino-4-hydroxy-6-methyltetrahydropteridine
0.102
L-phenylalanine
-
recombinant N- and C-terminal truncated enzyme, cofactor 6-methyltetrahydropterin
0.0058
L-tryptophan
-
recombinant N- and C-terminal truncated enzyme, cofactor 6-methyltetrahydrobipterin
0.0075
L-tryptophan
-
TPH as fusion protein with maltose-binding protein expressed in Escherichia coli
0.0132
L-tryptophan
0.02 mM ferrous ammonium, 0.5 mM (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin, 30°C
0.0186
L-tryptophan
pH 7.0, 30°C, recombinant mutant R441H fusion enzyme
0.0255
L-tryptophan
pH 7.0, 30°C, recombinant mutant P449R fusion enzyme
0.0282
L-tryptophan
pH 7.0, 30°C, recombinant wild-type TPH2 fusion enzyme
0.0449
L-tryptophan
pH 7.0, 30°C, recombinant phosphorylated wild-type TPH2
0.045
L-tryptophan
-
cofactor 2-amino-4-hydroxy-6-methyltetrahydropteridine
0.0479
L-tryptophan
-
recombinant N- and C-terminal truncated enzyme, cofactor tetrahydrobiopterin
0.0545
L-tryptophan
pH 7.0, 30°C, recombinant non-phosphorylated wild-type TPH2
0.0142
tetrahydrobiopterin
-
recombinant N- and C-terminal truncated enzyme, substrate phenylalanine
0.0147
tetrahydrobiopterin
pH 7.0, 30°C, recombinant mutant P449R fusion enzyme
0.0217
tetrahydrobiopterin
pH 7.0, 30°C, recombinant wild-type TPH2 fusion enzyme
0.0249
tetrahydrobiopterin
pH 7.0, 30°C, recombinant mutant R441H fusion enzyme
0.0289
tetrahydrobiopterin
pH 7.0, 30°C, recombinant detagged mutant R441H
0.0351
tetrahydrobiopterin
pH 7.0, 30°C, recombinant non-phosphorylated wild-type TPH2
0.0423
tetrahydrobiopterin
pH 7.0, 30°C, recombinant phosphorylated wild-type TPH2
0.0518
tetrahydrobiopterin
pH 7.0, 30°C, recombinant detagged mutant P449R
0.0684
tetrahydrobiopterin
pH 7.0, 30°C, recombinant detagged wild-type TPH2
0.135
tetrahydrobiopterin
-
recombinant N- and C-terminal truncated enzyme, substrate tryptophan
0.078
tryptophan
-
cofactor 2-amino-4-hydroxy-6-methyltetrahydropteridine
0.29
tryptophan
-
cofactor 2-amino-4-hydroxy-6,7-dimethyl-5,6,7,8-tetrahydropteridine
additional information
additional information
-
1.2% O2 with 0.2 mM 2-amino-4-hydroxy-6-methyl-5,6,7,8-tetrahydropteridine, 7.1% O2 with 0.4 mM 2-amino-4-hydroxy-6,7-dimethyl-5,6,7,8-tetrahydropteridine
-
additional information
additional information
-
20% O2, cofactor 2-amino-4-hydroxy-6,7-dimethyl-5,6,7,8-tetrahydropteridine, 2.5% O2, cofactor tetrahydrobipterine
-
additional information
additional information
-
the KM-value of TrpOH in the cerebral cortex and in the brainstem from diabetic rates are significantly increased when compared to those from control rats
-
additional information
additional information
-
isozymes TPH1 and TPH2 kinetics, overview
-
additional information
additional information
isozymes TPH1 and TPH2 kinetics, overview
-
additional information
additional information
kinetic mechanism of isozyme TPH1
-
additional information
additional information
kinetic mechanism of isozyme TPH1
-
additional information
additional information
kinetic mechanism of isozyme TPH1
-
additional information
additional information
kinetic mechanism of isozyme TPH1
-
additional information
additional information
kinetic mechanism of isozyme TPH2
-
additional information
additional information
kinetic mechanism of isozyme TPH2
-
additional information
additional information
kinetic mechanism of isozyme TPH2
-
additional information
additional information
kinetic mechanism of isozyme TPH2
-
additional information
additional information
kinetics of phosphorylated and non-phosphorylated wild-type and mutant enzymes
-
additional information
additional information
-
kinetics of phosphorylated and non-phosphorylated wild-type and mutant enzymes
-
additional information
additional information
-
kinetics of wild-type isozyme TPH1, overview
-
additional information
additional information
-
kinetics of wild-type isozyme TPH2 and of TPH2 deletion mutants, overview
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0026
1,10-phenanthroline
-
vs. 2-amino-4-hydroxy-6-methyl-5,6,7,8-tetrahydropteridine
0.202
D-Dopa
-
vs. (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin, component with low affinity
0.609
D-Dopa
-
vs. (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin, component with high affinity
0.007
dopamine
-
vs. (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin, component with high affinity
0.0393
dopamine
-
vs. (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin, component with low affinity
0.0803
L-Dopa
-
vs. (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin, component with high affinity
0.0887
L-Dopa
-
vs. (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin, component with low affinity
0.0727
L-phenylalanine
0.02 mM ferrous ammonium, 0.5 mM (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin, 30°C
0.0162
L-tyrosine
-
vs. (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin, component with high affinity
0.306
L-tyrosine
-
vs. (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin, component with low affinity
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
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
0.007552
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
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
-
-
0.00016
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
Homo sapiens
-
0.000024
4-[4-amino-6-[2,2,2-trifluoro-1-(2-furan-2-ylphenyl)ethoxy]-1,3,5-triazin-2-yl]-L-phenylalanine
Mus musculus
-
-
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
-
0.011036
4-[[(E)-amino(benzylamino)methylidene]carbamoyl]-L-phenylalanine
Homo sapiens
-
pH and temperature not specified in the publication
0.001844
4-[[(E)-amino([[2-(1H-1,2,4-triazol-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
Homo sapiens
-
pH and temperature not specified in the publication
0.000501
4-[[(E)-amino([[2-(1H-pyrazol-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
Homo sapiens
-
pH and temperature not specified in the publication
0.000011
4-[[(E)-amino([[2-(2-azabicyclo[2.2.1]heptan-2-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
Homo sapiens
-
pH and temperature not specified in the publication
0.000015
4-[[(E)-amino([[2-(2-chlorophenoxy)-6-(piperidin-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
Homo sapiens
-
pH and temperature not specified in the publication
0.00001
4-[[(E)-amino([[2-(2-methoxyphenoxy)-6-(piperidin-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
Homo sapiens
-
pH and temperature not specified in the publication
0.000011
4-[[(E)-amino([[2-(2-methylphenoxy)-6-(piperidin-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
Homo sapiens
-
pH and temperature not specified in the publication
0.000015
4-[[(E)-amino([[2-(2-methylpiperidin-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
Homo sapiens
-
pH and temperature not specified in the publication
0.000335
4-[[(E)-amino([[2-(2H-1,2,3-triazol-2-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
Homo sapiens
-
pH and temperature not specified in the publication
0.000025
4-[[(E)-amino([[2-(3,5-dimethylpiperidin-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
Homo sapiens
-
pH and temperature not specified in the publication
0.000045
4-[[(E)-amino([[2-(3-azabicyclo[3.1.0]hexan-3-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
Homo sapiens
-
pH and temperature not specified in the publication
0.000006
4-[[(E)-amino([[2-(3-chlorophenoxy)-6-(piperidin-1-yl)phenyl]methyl]amino)methylidene]carbamoyl]-L-phenylalanine
Homo sapiens
-