5-hydroxy-L-tryptophan
362,296 routes · scope human · up to 3 steps · built 5 October 2026 · Reactions · API
386 compounds within 3 steps: 3 in 1, 46 in 2, 337 in 3
Three steps
- (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + L-tryptophan + O2 = 5-hydroxy-L-tryptophan + (4aS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterin
- transport of glycine and tryptophan (cytosol to extracellular)
- N(omega)-methyl-L-arginine + glyoxylate = 5-(3-methylguanidino)-2-oxopentanoate + glycine
Catalysed by TPH1, TPH2, SLC7A5, AGXT2extracellular space, cytosolOne of 4 routes
- (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + L-tryptophan + O2 = 5-hydroxy-L-tryptophan + (4aS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterin
- transport of tryptophan and valine (cytosol to extracellular)
- L-Valine:2-oxoglutarate aminotransferase
Catalysed by TPH1, TPH2, SLC7A5, BCAT2extracellular space, cytosol, mitochondrial matrixOne of 3 routes
- (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + L-tryptophan + O2 = 5-hydroxy-L-tryptophan + (4aS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterin
- transport of cysteine and tryptophan (cytosol to extracellular)
- Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
Catalysed by TPH1, TPH2, SLC7A5, MOCOSextracellular space, cytosol
- 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
- transport of serotonin (cytosol to extracellular)
- transport of S-glutathionyl-2-4-dinitrobenzene (cytosol to extracellular)
Catalysed by DDC, SLCO1A2, SLCO1B3extracellular space, cytosolOne of 4 routes
- (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + L-tryptophan + O2 = 5-hydroxy-L-tryptophan + (4aS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterin
- transport of glycine and tryptophan (cytosol to extracellular)
- glycine to glycoursodeoxycholate conversion
Catalysed by TPH1, TPH2, SLC7A5extracellular space, cytosolOne of 6 routes
- 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
- transport of GSH and serotonin (cytosol to extracellular)
- glutathione transferase (GSH)
Catalysed by DDC, SLCO1A2, SLCO1B3, PTGES and 20 moreextracellular space, cytosolOne of 4 routes
- 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
- transport of serotonin (cytosol to extracellular)
- transport of prostaglandin E3 (cytosol to extracellular)
Catalysed by DDC, SLCO1A2, SLCO1B3, SLCO1B1extracellular space, cytosolOne of 4 routes
- 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
- transport of serotonin (cytosol to extracellular)
- transport of prostaglandin A2 (cytosol to extracellular)
Catalysed by DDC, SLCO1A2, SLCO1B3, SLCO1B1extracellular space, cytosolOne of 4 routes
- 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
- transport of serotonin (cytosol to extracellular)
- transport of prostaglandin B1 (cytosol to extracellular)
Catalysed by DDC, SLCO1A2, SLCO1B3, SLCO1B1extracellular space, cytosolOne of 4 routes
- 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
- transport of serotonin (cytosol to extracellular)
- transport of leukotriene F4 (cytosol to extracellular)
Catalysed by DDC, SLCO1A2, SLCO1B3, SLCO1B1extracellular space, cytosolOne of 4 routes
- (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + L-tryptophan + O2 = 5-hydroxy-L-tryptophan + (4aS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterin
- transport of glycine and tryptophan (cytosol to extracellular)
- (9Z)-octadecenoyl-CoA + glycine = N-(9Z-octadecenoyl)glycine + CoA + H(+)
Catalysed by TPH1, TPH2, SLC7A5, GLYATL3 and 1 moreextracellular space, cytosol
- (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + L-tryptophan + O2 = 5-hydroxy-L-tryptophan + (4aS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterin
- transport of phenylalanine and tryptophan (cytosol to extracellular)
- L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
Catalysed by TPH1, TPH2, SLC7A5, PM20D1extracellular space, cytosol
- (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + L-tryptophan + O2 = 5-hydroxy-L-tryptophan + (4aS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterin
- transport of phenylalanine and tryptophan (cytosol to extracellular)
- (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
Catalysed by TPH1, TPH2, SLC7A5, PM20D1extracellular space, cytosol
- (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + L-tryptophan + O2 = 5-hydroxy-L-tryptophan + (4aS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterin
- transport of leucine and tryptophan (cytosol to extracellular)
- N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate
Catalysed by TPH1, TPH2, SLC7A5, PM20D1extracellular space, cytosol
- (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + L-tryptophan + O2 = 5-hydroxy-L-tryptophan + (4aS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterin
- transport of glycine and tryptophan (cytosol to extracellular)
- octadecanoyl-CoA + glycine = N-octadecanoylglycine + CoA + H(+)
Catalysed by TPH1, TPH2, SLC7A5, GLYATL2extracellular space, cytosol
- (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + L-tryptophan + O2 = 5-hydroxy-L-tryptophan + (4aS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterin
- transport of glycine and tryptophan (cytosol to extracellular)
- (9Z)-hexadecenoyl-CoA + glycine = N-(9Z-hexadecenoyl)-glycine + CoA + H(+)
Catalysed by TPH1, TPH2, SLC7A5, GLYATL2extracellular space, cytosol
- (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + L-tryptophan + O2 = 5-hydroxy-L-tryptophan + (4aS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterin
- transport of glycine and tryptophan (cytosol to extracellular)
- hexadecanoyl-CoA + glycine = N-hexadecanoylglycine + CoA + H(+)
Catalysed by TPH1, TPH2, SLC7A5, GLYATL3extracellular space, cytosol
- (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + L-tryptophan + O2 = 5-hydroxy-L-tryptophan + (4aS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterin
- transport of glycine and tryptophan (cytosol to extracellular)
- dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)
Catalysed by TPH1, TPH2, SLC7A5, GLYATL2extracellular space, cytosol
- (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + L-tryptophan + O2 = 5-hydroxy-L-tryptophan + (4aS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterin
- transport of glycine and tryptophan (cytosol to extracellular)
- decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)
Catalysed by TPH1, TPH2, SLC7A5, GLYATL2extracellular space, cytosol
- (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + L-tryptophan + O2 = 5-hydroxy-L-tryptophan + (4aS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterin
- transport of glycine and tryptophan (cytosol to extracellular)
- octanoyl-CoA + glycine = N-octanoylglycine + CoA + H(+)
Catalysed by TPH1, TPH2, SLC7A5, GLYATL2extracellular space, cytosol
- (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + L-tryptophan + O2 = 5-hydroxy-L-tryptophan + (4aS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterin
- transport of ornithine and tryptophan (cytosol to extracellular)
- D-histidine(in) + L-ornithine(out) + H(+)(in) = D-histidine(out) + L-ornithine(in) + H(+)(out)
Catalysed by TPH1, TPH2, SLC7A6, SLC25A2extracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes
- (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + L-tryptophan + O2 = 5-hydroxy-L-tryptophan + (4aS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterin
- transport of arginine and tryptophan (cytosol to extracellular)
- L-homoarginine(in) + L-arginine(out) = L-homoarginine(out) + L-arginine(in)
Catalysed by TPH1, TPH2, SLC7A6, SLC25A29extracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 4 routes
- (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + L-tryptophan + O2 = 5-hydroxy-L-tryptophan + (4aS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterin
- transport of histidine and tryptophan (cytosol to extracellular)
- Formation of homocarnosine
Catalysed by TPH1, TPH2, SLC7A6, CARNS1extracellular space, cytosol
- (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + L-tryptophan + O2 = 5-hydroxy-L-tryptophan + (4aS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterin
- transport of glycine and tryptophan (cytosol to extracellular)
- 5-phospho-beta-D-ribosylamine + glycine + ATP = N(1)-(5-phospho-beta-D-ribosyl)glycinamide + ADP + phosphate + H(+)
Catalysed by TPH1, TPH2, SLC7A5, GARTextracellular space, cytosol
- (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + L-tryptophan + O2 = 5-hydroxy-L-tryptophan + (4aS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterin
- transport of glycine and tryptophan (cytosol to extracellular)
- L-cystine-bis-glycine + 2 H2O = L-cystine + 2 glycine
Catalysed by TPH1, TPH2, SLC7A5, DPEP1 and 1 moreextracellular space, cytosol
- (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + L-tryptophan + O2 = 5-hydroxy-L-tryptophan + (4aS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterin
- (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin(out) + a dicarboxylate(in) = (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin(in) + a dicarboxylate(out)
- indoxyl sulfate(out) + a dicarboxylate(in) = indoxyl sulfate(in) + a dicarboxylate(out)
Catalysed by TPH1, TPH2, SLC22A6, SLC22A8inner side of the membrane, outer side of the membraneOne of 2 routes
- (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + L-tryptophan + O2 = 5-hydroxy-L-tryptophan + (4aS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterin
- transport of glycine and tryptophan (cytosol to extracellular)
- glycyldehydrophenylalanine + H2O = 2,3-didehydrophenylalanine + glycine
Catalysed by TPH1, TPH2, SLC7A5, DPEP1extracellular space, cytosol
- (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + L-tryptophan + O2 = 5-hydroxy-L-tryptophan + (4aS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterin
- transport of glutamine and tryptophan (cytosol to extracellular)
- N(2)-formyl-N(1)-(5-phospho-beta-D-ribosyl)glycinamide + L-glutamine + ATP + H2O = 2-formamido-N(1)-(5-O-phospho-beta-D-ribosyl)acetamidine + L-glutamate + ADP + phosphate + H(+)
Catalysed by TPH1, TPH2, SLC7A5, PFASextracellular space, cytosol
- (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + L-tryptophan + O2 = 5-hydroxy-L-tryptophan + (4aS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterin
- transport of phenylalanine and tryptophan (cytosol to extracellular)
- Chymase
Catalysed by TPH1, TPH2, SLC7A5, CMA1extracellular space, cytosolOne of 3 routes
- (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + L-tryptophan + O2 = 5-hydroxy-L-tryptophan + (4aS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterin
- transport of glycine and tryptophan (cytosol to extracellular)
- a fatty acyl-CoA + glycine = an N-(fatty acyl)-glycine + CoA + H(+)
Catalysed by TPH1, TPH2, SLC7A5, GLYATL2extracellular space, cytosol
- (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + L-tryptophan + O2 = 5-hydroxy-L-tryptophan + (4aS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterin
- transport of glycine and tryptophan (cytosol to extracellular)
- (9Z,12Z)-octadecadienoyl-CoA + glycine = N-(9Z,12Z-octadecadienoyl)-glycine + CoA + H(+)
Catalysed by TPH1, TPH2, SLC7A5, GLYATL2extracellular space, cytosol
- 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
- acetyl-CoA:aralkylamine N-acetyltransferase
- carnitine O-palmitoyltransferase ((7Z)-octadecenoyl-CoA)
Catalysed by DDC, AANAT, CPT1A, CPT1C and 1 morecytosolOne of 3 routes
- (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + L-tryptophan + O2 = 5-hydroxy-L-tryptophan + (4aS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterin
- Transport of L-Tryptophan by Atb0 Transporter
- transport of chloride and choline (cytosol to extracellular)
Catalysed by TPH1, TPH2, SLC6A14, SLC5A7extracellular space, cytosolOne of 2 routes
- 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
- transport of serotonin (cytosol to extracellular)
- transport of acetylcholine (cytosol to extracellular)
Catalysed by DDC, SLCO1A2, SLCO1B3extracellular space, cytosolOne of 4 routes
- (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + L-tryptophan + O2 = 5-hydroxy-L-tryptophan + (4aS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterin
- transport of alanine and tryptophan (cytosol to extracellular)
- (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
Catalysed by TPH1, TPH2, SLC7A5, AGXT2extracellular space, cytosol, mitochondrial matrixOne of 16 routes
- 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
- acetyl-CoA:aralkylamine N-acetyltransferase
- 5-aminolevulinate synthase (2-amino-3-oxoadipate)
Catalysed by DDC, AANAT, ALAS1, CPNE7cytosol, mitochondrial matrixOne of 8 routes
- 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
- acetyl-CoA:aralkylamine N-acetyltransferase
- glycine N-acyltransferase (2-methylbutyryl-CoA)
Catalysed by DDC, AANAT, GLYAT, GLYATL2 and 1 morecytosol, mitochondrial matrixOne of 2 routes
- 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
- acetyl-CoA:aralkylamine N-acetyltransferase
- acetyl-CoA C-acyltransferase (3-oxo-4-methyl-pentanoyl-CoA)
Catalysed by DDC, AANAT, HADHA, ACAA2 and 1 morecytosol, mitochondrial matrixOne of 3 routes
- 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
- acetyl-CoA:aralkylamine N-acetyltransferase
- glycine N-acyltransferase (isovalerylglycine)
Catalysed by DDC, AANAT, GLYAT, GLYATL2 and 1 morecytosol, mitochondrial matrixOne of 3 routes
- 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
- acetyl-CoA:aralkylamine N-acetyltransferase
- Arachidonate:CoA ligase (AMP-forming)
Catalysed by DDC, AANAT, SLC27A2, ACSL4 and 6 morecytosolOne of 11 routes
- 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
- acetyl-CoA:aralkylamine N-acetyltransferase
- propanoyl-CoA C-acyltransferase
Catalysed by DDC, AANAT, ACAA1, SCP2 and 1 morecytosol, peroxisomeOne of 2 routes
- 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
- acetyl-CoA:aralkylamine N-acetyltransferase
- Palmitate:CoA ligase (AMP-forming)
Catalysed by DDC, AANAT, SLC27A2, ACSL4 and 6 morecytosolOne of 11 routes
- 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
- acetyl-CoA:aralkylamine N-acetyltransferase
- Transport of octadecenoyl-CoA into Mitochondrial Matrix
Catalysed by DDC, AANAT, CPT1A, CPT1C and 1 morecytosolOne of 11 routes
- 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
- acetyl-CoA:aralkylamine N-acetyltransferase
- Propanoate:CoA ligase (AMP-forming)
Catalysed by DDC, AANAT, ACSS3, ACSS2 and 1 morecytosolOne of 43 routes
- (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + L-tryptophan + O2 = 5-hydroxy-L-tryptophan + (4aS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterin
- transport of glycine and tryptophan (cytosol to extracellular)
- transport of D-alanine and glycine (cytosol to extracellular)
Catalysed by TPH1, TPH2, SLC7A5, SLC3A2 and 1 moreextracellular space, cytosolOne of 5 routes