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Literature summary for 1.14.16.4 extracted from

  • Shi, Z.C.; Devasagayaraj, A.; Gu, K.; Jin, H.; Marinelli, B.; Samala, L.; Scott, S.; Stouch, T.; Tunoori, A.; Wang, Y.; Zang, Y.; Zhang, C.; Kimball, S.D.; Main, A.J.; Sun, W.; Yang, Q.; Nouraldeen, A.; Yu, X.Q.; Buxton, E.; Patel, S.; Nguyen, N.; Swaffield, J.; Powell, D.R.; Wilson, A.; Liu, Q.
    Modulation of peripheral serotonin levels by novel tryptophan hydroxylase inhibitors for the potential treatment of functional gastrointestinal disorders (2008), J. Med. Chem., 51, 3684-3687.
    View publication on PubMed

Inhibitors

Inhibitors Comment Organism Structure
3-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)phenylalanine
-
Mus musculus
3-amino-3-[4-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)phenyl]propanoic acid
-
Mus musculus
3-[1-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)piperidin-4-yl]alanine
-
Mus musculus
3-[3-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)-1H-pyrazol-1-yl]alanine
-
Mus musculus
3-[5-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)pyridin-2-yl]alanine
-
Mus musculus
4-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)-2-fluorophenylalanine
-
Mus musculus
4-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)-a-methylphenylalanine
-
Mus musculus
4-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)-L-phenylalanine
-
Mus musculus
4-(5-[[(1-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl)methyl]amino]pyrazin-2-yl)-L-phenylalanine
-
Mus musculus
4-(5-[[(1-hydroxynaphthalen-2-yl)methyl]amino]pyrazin-2-yl)-L-phenylalanine
-
Mus musculus
4-(5-[[(2'-methylbiphenyl-2-yl)methyl]amino]pyrazin-2-yl)-L-phenylalanine
-
Mus musculus
4-(5-[[(9-ethyl-9H-carbazol-3-yl)methyl]amino]pyrazin-2-yl)-L-phenylalanine
-
Mus musculus
4-(5-[[3-(cyclopentyloxy)-4-methoxybenzyl]amino]pyrazin-2-yl)-L-phenylalanine
-
Mus musculus
4-Chlorophenylalanine
-
Mus musculus
4-ethynylphenylalanine
-
Mus musculus
4-[4-amino-6-(1-naphthalen-2-ylethoxy)-1,3,5-triazin-2-yl]-L-phenylalanine
-
Mus musculus
4-[4-amino-6-(2,2,2-trifluoro-1-naphthalen-2-ylethoxy)-1,3,5-triazin-2-yl]-L-phenylalanine
-
Mus musculus
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
4-[4-amino-6-[2,2,2-trifluoro-1-(2-furan-2-ylphenyl)ethoxy]-1,3,5-triazin-2-yl]-L-phenylalanine
-
Mus musculus
4-[4-amino-6-[2,2,2-trifluoro-1-(3'-methylbiphenyl-2-yl)ethoxy]-1,3,5-triazin-2-yl]-L-phenylalanine
-
Mus musculus
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
4-[5-[(3,4-dimethoxybenzyl)amino]pyrazin-2-yl]-L-phenylalanine
-
Mus musculus
4-[5-[(4-cyanobenzyl)amino]pyrazin-2-yl]-L-phenylalanine
-
Mus musculus
4-[5-[(biphenyl-4-ylmethyl)amino]pyrazin-2-yl]-L-phenylalanine
-
Mus musculus
4-[5-[(cyclohexylmethyl)amino]pyrazin-2-yl]-L-phenylalanine
-
Mus musculus
4-[5-[(furan-3-ylmethyl)amino]pyrazin-2-yl]-L-phenylalanine
-
Mus musculus
4-[5-[(pyridin-3-ylmethyl)amino]pyrazin-2-yl]-L-phenylalanine
-
Mus musculus
4-[5-[(quinolin-3-ylmethyl)amino]pyrazin-2-yl]-L-phenylalanine
-
Mus musculus

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
L-tryptophan + tetrahydrobiopterin + O2 Mus musculus 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 5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
?

Organism

Organism UniProt Comment Textmining
Mus musculus
-
-
-

Source Tissue

Source Tissue Comment Organism Textmining
brain
-
Mus musculus
-
central nervous system
-
Mus musculus
-
additional information TPH1 is primarily expressed in the pineal gland and non-neuronal tissues, such as enterochromaffin cells of the gastrointestinal tract. TPH2, the dominant isozyme in the brain, is expressed exclusively in neuronal cells, such as dorsal raphe or myenteric plexus cells Mus musculus
-
pineal gland
-
Mus musculus
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
L-tryptophan + tetrahydrobiopterin + O2
-
Mus musculus 5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
?
L-tryptophan + tetrahydrobiopterin + O2 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 Mus musculus 5-hydroxy-L-tryptophan + 4a-hydroxytetrahydrobiopterin
-
?

Synonyms

Synonyms Comment Organism
TPH1
-
Mus musculus
TPH2
-
Mus musculus
tryptophan hydroxylase
-
Mus musculus

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.000013
-
-
Mus musculus 4-(5-[[(1-hydroxynaphthalen-2-yl)methyl]amino]pyrazin-2-yl)-L-phenylalanine
0.000024
-
-
Mus musculus 4-[4-amino-6-[2,2,2-trifluoro-1-(2-furan-2-ylphenyl)ethoxy]-1,3,5-triazin-2-yl]-L-phenylalanine
0.000026
-
-
Mus musculus 4-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)-L-phenylalanine
0.000029
-
-
Mus musculus 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
0.000031
-
-
Mus musculus 4-(5-[[(9-ethyl-9H-carbazol-3-yl)methyl]amino]pyrazin-2-yl)-L-phenylalanine
0.000032
-
-
Mus musculus 4-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)-L-phenylalanine
0.00004
-
-
Mus musculus 4-(5-[[(2'-methylbiphenyl-2-yl)methyl]amino]pyrazin-2-yl)-L-phenylalanine
0.000044
-
-
Mus musculus 4-[5-[(biphenyl-4-ylmethyl)amino]pyrazin-2-yl]-L-phenylalanine
0.000045
-
-
Mus musculus 4-(5-[[3-(cyclopentyloxy)-4-methoxybenzyl]amino]pyrazin-2-yl)-L-phenylalanine
0.000046
-
-
Mus musculus 4-(5-[[(1-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl)methyl]amino]pyrazin-2-yl)-L-phenylalanine
0.000054
-
-
Mus musculus 4-[4-amino-6-[2,2,2-trifluoro-1-(5-furan-2-ylthiophen-2-yl)ethoxy]-1,3,5-triazin-2-yl]-L-phenylalanine
0.000069
-
-
Mus musculus 4-[5-[(3,4-dimethoxybenzyl)amino]pyrazin-2-yl]-L-phenylalanine
0.00007
-
-
Mus musculus 4-[4-amino-6-[2,2,2-trifluoro-1-(3'-methylbiphenyl-2-yl)ethoxy]-1,3,5-triazin-2-yl]-L-phenylalanine
0.00011
-
-
Mus musculus 4-[5-[(4-cyanobenzyl)amino]pyrazin-2-yl]-L-phenylalanine
0.00018
-
-
Mus musculus 4-[4-amino-6-(2,2,2-trifluoro-1-naphthalen-2-ylethoxy)-1,3,5-triazin-2-yl]-L-phenylalanine
0.00019
-
-
Mus musculus 4-[5-[(quinolin-3-ylmethyl)amino]pyrazin-2-yl]-L-phenylalanine
0.0002
-
-
Mus musculus 4-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)-2-fluorophenylalanine
0.00024
-
-
Mus musculus 4-[5-[(cyclohexylmethyl)amino]pyrazin-2-yl]-L-phenylalanine
0.00038
-
-
Mus musculus 4-[4-amino-6-(1-naphthalen-2-ylethoxy)-1,3,5-triazin-2-yl]-L-phenylalanine
0.00077
-
-
Mus musculus 3-[1-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)piperidin-4-yl]alanine
0.00089
-
-
Mus musculus 3-[5-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)pyridin-2-yl]alanine
0.00096
-
-
Mus musculus 4-[5-[(furan-3-ylmethyl)amino]pyrazin-2-yl]-L-phenylalanine
0.00377
-
-
Mus musculus 3-amino-3-[4-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)phenyl]propanoic acid
0.00615
-
-
Mus musculus 4-[5-[(pyridin-3-ylmethyl)amino]pyrazin-2-yl]-L-phenylalanine
0.011
-
-
Mus musculus 3-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)phenylalanine
0.0111
-
-
Mus musculus 4-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)-a-methylphenylalanine
0.0126
-
-
Mus musculus 3-[3-(4-amino-6-[[(1R)-1-naphthalen-2-ylethyl]amino]-1,3,5-triazin-2-yl)-1H-pyrazol-1-yl]alanine
0.03
-
-
Mus musculus 4-ethynylphenylalanine
0.092
-
-
Mus musculus 4-Chlorophenylalanine