5-hydroxy-L-tryptophan

Three steps

• (3Z)-dodecenoyl-CoAReach from here →
  1. 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
  2. acetyl-CoA:aralkylamine N-acetyltransferase
  3. acetyl-CoA C-acyltransferase (3-oxomyrist-5-enoyl-CoA)

  Catalysed by DDC, AANAT, HADHA, ACAA2 and 1 morecytosol, mitochondrial matrixOne of 3 routes

• S-sulfanyl-L-cysteineReach from here →
  1. (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
  2. transport of cysteine and tryptophan (cytosol to extracellular)
  3. 2 L-cysteine = S-sulfanyl-L-cysteine + L-alanine

  Catalysed by TPH1, TPH2, SLC7A5, CARS2extracellular space, cytosol

• (25R)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oyl-CoAReach from here →
  1. 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
  2. acetyl-CoA:aralkylamine N-acetyltransferase
  3. 3alpha,7alpha,12alpha-trihydroxy-5beta-cholestanoate:CoA ligase (AMP-forming)

  Catalysed by DDC, AANAT, SLC27A2, SLC27A5cytosol, endoplasmic reticulumOne of 3 routes

• 5-phospho-beta-D-ribosylamineReach from here →
  1. (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
  2. transport of glutamine and tryptophan (cytosol to extracellular)
  3. phosphoribosyl pyrophosphate amidotransferase (glutamine)

  Catalysed by TPH1, TPH2, SLC7A5, PPATextracellular space, cytosolOne of 2 routes

• D-glucosamine 6-phosphateReach from here →
  1. (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
  2. transport of glutamine and tryptophan (cytosol to extracellular)
  3. D-fructose 6-phosphate + L-glutamine = D-glucosamine 6-phosphate + L-glutamate

  Catalysed by TPH1, TPH2, SLC7A5, GFPT2 and 1 moreextracellular space, cytosol

• L-methionine (S)-S-oxideReach from here →
  1. (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
  2. transport of methionine and tryptophan (cytosol to extracellular)
  3. [thioredoxin]-disulfide + L-methionine + H2O = L-methionine (S)-S-oxide + [thioredoxin]-dithiol

  Catalysed by TPH1, TPH2, SLC7A5, MSRAextracellular space, cytosol

• L-methionine (R)-S-oxideReach from here →
  1. (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
  2. transport of methionine and tryptophan (cytosol to extracellular)
  3. [thioredoxin]-disulfide + L-methionine + H2O = L-methionine (R)-S-oxide + [thioredoxin]-dithiol

  Catalysed by TPH1, TPH2, SLC7A5, MSRB3 and 2 moreextracellular space, cytosol

• 5-amino-2-oxopentanoateReach from here →
  1. (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
  2. transport of ornithine and tryptophan (cytosol to extracellular)
  3. L-ornithine + pyruvate = 5-amino-2-oxopentanoate + L-alanine

  Catalysed by TPH1, TPH2, SLC7A6, AGXT2extracellular space, cytosolOne of 2 routes

• deoxycholoyl-CoAReach from here →
  1. 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
  2. acetyl-CoA:aralkylamine N-acetyltransferase
  3. cholate-CoA ligase (3alpha,12alpha-dihydroxy-5beta-cholanate)

  Catalysed by DDC, AANAT, SLC27A2, SLC27A5cytosolOne of 4 routes

• S-sulfanylglutathioneReach from here →
  1. 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
  2. transport of GSH and serotonin (cytosol to extracellular)
  3. Sulfide:glutathione,quinone oxidoreductase

  Catalysed by DDC, SLCO1A2, SLCO1B3, SQORextracellular space, cytosol, mitochondrial matrix

• N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycineReach from here →
  1. (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
  2. transport of glycine and tryptophan (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + glycine = N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycine + CoA + H(+)

  Catalysed by TPH1, TPH2, SLC7A5, GLYATL2extracellular space, cytosolOne of 2 routes

• N-[(R)-4-phosphopantothenoyl]-L-cysteineReach from here →
  1. (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
  2. transport of cysteine and tryptophan (cytosol to extracellular)
  3. (R)-4'-phosphopantothenate:L-cysteine ligase

  Catalysed by TPH1, TPH2, SLC7A5, PPCSextracellular space, cytosolOne of 4 routes

• 4-aminobutanoateReach from here →
  1. (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
  2. Transport of L-Tryptophan by Atb0 Transporter
  3. transport of 4-aminobutyrate and chloride (cytosol to extracellular)

  Catalysed by TPH1, TPH2, SLC6A14, SLC6A12extracellular space, cytosolOne of 4 routes

• 3-iodo-L-tyrosineReach from here →
  1. (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
  2. transport of tryptophan and tyrosine (cytosol to extracellular)
  3. thyroid peroxidase (iodine)

  Catalysed by TPH1, TPH2, SLC7A5, TPOextracellular space, cytosolOne of 2 routes

• dopamineReach from here →
  1. (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
  2. (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + L-tyrosine + O2 = (4aS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterin + L-dopa
  3. L-dopa + H(+) = dopamine + CO2

  Catalysed by TPH1, TPH2, TH, DDCOne of 5 routes

• glycolithocholate 3-sulfateReach from here →
  1. 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
  2. transport of serotonin (cytosol to extracellular)
  3. transport of S-glutathionyl-2-4-dinitrobenzene (cytosol to extracellular)

  Catalysed by DDC, SLCO1A2, SLCO1B3extracellular space, cytosolOne of 4 routes

• L-prolineReach from here →
  1. (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
  2. transport of alanine and tryptophan (cytosol to extracellular)
  3. L-proline(out) + L-alanine(in) + Na(+)(out) = L-proline(in) + L-alanine(out) + Na(+)(in)

  Catalysed by TPH1, TPH2, SLC7A5, SLC1A4extracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• estrone 3-sulfateReach from here →
  1. 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
  2. transport of serotonin (cytosol to extracellular)
  3. transport of estrone 3-sulfate (cytosol to extracellular)

  Catalysed by DDC, SLCO1A2, SLCO1B3, SLCO1B1extracellular space, cytosolOne of 2 routes

• prostaglandin E2Reach from here →
  1. (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
  2. (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin(out) + a dicarboxylate(in) = (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin(in) + a dicarboxylate(out)
  3. prostaglandin E2(out) + a dicarboxylate(in) = prostaglandin E2(in) + a dicarboxylate(out)

  Catalysed by TPH1, TPH2, SLC22A6, SLC22A8inner side of the membrane, outer side of the membraneOne of 6 routes

• N-benzoylglycineReach from here →
  1. (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
  2. transport of glycine and tryptophan (cytosol to extracellular)
  3. Hippurate (Benzoylglycinate) Formation

  Catalysed by TPH1, TPH2, SLC7A5extracellular space, cytosol, mitochondrial matrixOne of 4 routes

• 3-sulfino-L-alanineReach from here →
  1. (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
  2. transport of cysteine and tryptophan (cytosol to extracellular)
  3. L-Cysteine:oxygen oxidoreductase

  Catalysed by TPH1, TPH2, SLC7A5, CDO1extracellular space, cytosolOne of 6 routes

• decanoyl-CoAReach from here →
  1. 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
  2. acetyl-CoA:aralkylamine N-acetyltransferase
  3. medium-chain acyl-CoA ligase (decanoic acid)

  Catalysed by DDC, AANAT, ACSM4, ACSM1 and 4 morecytosolOne of 7 routes

• (2E)-hexadecenoyl-CoAReach from here →
  1. 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
  2. acetyl-CoA:aralkylamine N-acetyltransferase
  3. Carnitine O-Palmitoyltransferase

  Catalysed by DDC, AANAT, CPT1A, CPT1C and 1 morecytosolOne of 4 routes

• (9Z)-hexadecenoyl-CoAReach from here →
  1. 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
  2. acetyl-CoA:aralkylamine N-acetyltransferase
  3. long-chain-fatty-acid-CoA ligase (palmitolate)

  Catalysed by DDC, AANAT, SLC27A2, ACSL4 and 6 morecytosolOne of 11 routes

• L-cysteinylglycineReach from here →
  1. (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
  2. transport of alanine and tryptophan (cytosol to extracellular)
  3. gamma-glutamyltransferase (alanine)

  Catalysed by TPH1, TPH2, SLC7A5, GGTLC3 and 5 moreextracellular space, cytosolOne of 6 routes

• 3-hydroxyisovaleryl-CoAReach from here →
  1. 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
  2. acetyl-CoA:aralkylamine N-acetyltransferase
  3. (3-Hydroxyisovalerylcoa->3-Hydroxyisovalerylcarnitine)

  Catalysed by DDC, AANAT, CPT1A, CPT1Bcytosol

• (5-hydroxyindol-3-yl)acetateReach from here →
  1. 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
  2. 5-Hydroxytryptamine:oxygen oxidoreductase(deaminating)(flavin-containing)
  3. 5-Hydroxyindoleacetaldehyde:NAD+ Oxidoreductase, Mitochondrial

  Catalysed by DDC, MAOA, MAOB, ALDH2 and 1 morecytosol, mitochondrial matrixOne of 4 routes

• CHEBI:63544Reach from here →
  1. 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
  2. acetyl-CoA:aralkylamine N-acetyltransferase
  3. long-chain-fatty-acid-CoA ligase (adrenic acid)

  Catalysed by DDC, AANAT, SLC27A2, ACSL4 and 6 morecytosolOne of 7 routes

• hexacosanoyl-CoAReach from here →
  1. 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
  2. acetyl-CoA:aralkylamine N-acetyltransferase
  3. long-chain-fatty-acid-CoA ligase (cerotic acid)

  Catalysed by DDC, AANAT, SLC27A2, ACSL4 and 6 morecytosolOne of 5 routes

• tetracosanoyl-CoAReach from here →
  1. 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
  2. acetyl-CoA:aralkylamine N-acetyltransferase
  3. long-chain-fatty-acid-CoA ligase (lignocerate)

  Catalysed by DDC, AANAT, SLC27A2, ACSL4 and 6 morecytosolOne of 10 routes

• docosanoyl-CoAReach from here →
  1. 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
  2. acetyl-CoA:aralkylamine N-acetyltransferase
  3. long-chain-fatty-acid-CoA ligase (behenic acid)

  Catalysed by DDC, AANAT, SLC27A2, ACSL4 and 6 morecytosolOne of 9 routes

• N(5)-[(Z)-amino(hydroxyimino)methyl]ornithineReach from here →
  1. (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
  2. transport of arginine and tryptophan (cytosol to extracellular)
  3. L-arginine,NADPH:oxygen oxidoreductase (N-(omega)-hydroxyarginine-forming)

  Catalysed by TPH1, TPH2, SLC7A6, NOS3 and 2 moreextracellular space, cytosol

• xanthurenateReach from here →
  1. (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
  2. Transport of 3-Hydroxy-L-Kynurenine
  3. Kynurenine-Oxoglutarate Transaminase

  Catalysed by TPH1, TPH2, SLC7A5, AADATextracellular space, cytosol, mitochondrial matrixOne of 2 routes

• Mo-molybdopterinReach from here →
  1. (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
  2. transport of alanine and tryptophan (cytosol to extracellular)
  3. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O

  Catalysed by TPH1, TPH2, SLC7A5, MOCOSextracellular space, cytosol

• (2E)-octadecenoyl-CoAReach from here →
  1. 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
  2. acetyl-CoA:aralkylamine N-acetyltransferase
  3. Carnitine O-Palmitoyltransferase

  Catalysed by DDC, AANAT, CPT1A, CPT1C and 1 morecytosolOne of 3 routes

• (6Z,9Z,12Z,15Z)-octadecatetraenoyl-CoAReach from here →
  1. 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
  2. acetyl-CoA:aralkylamine N-acetyltransferase
  3. long-chain-fatty-acid-CoA ligase (stearidonic acid)

  Catalysed by DDC, AANAT, SLC27A2, ACSL4 and 6 morecytosolOne of 8 routes

• (R)-noradrenalineReach from here →
  1. 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
  2. transport of serotonin (cytosol to extracellular)
  3. transport of noradrenaline (cytosol to extracellular)

  Catalysed by DDC, SLCO1A2, SLCO1B3extracellular space, cytosolOne of 4 routes

• (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoAReach from here →
  1. 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
  2. acetyl-CoA:aralkylamine N-acetyltransferase
  3. long-chain-fatty-acid-CoA ligase (EPA)

  Catalysed by DDC, AANAT, SLC27A2, ACSL4 and 6 morecytosolOne of 9 routes

• (7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl-CoAReach from here →
  1. 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
  2. acetyl-CoA:aralkylamine N-acetyltransferase
  3. long-chain-fatty-acid-CoA ligase (DPA)

  Catalysed by DDC, AANAT, SLC27A2, ACSL4 and 6 morecytosolOne of 6 routes

• (9Z,12Z,15Z)-octadecatrienoyl-CoAReach from here →
  1. 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
  2. acetyl-CoA:aralkylamine N-acetyltransferase
  3. long-chain-fatty-acid-CoA ligase (linolenate)

  Catalysed by DDC, AANAT, SLC27A2, ACSL4 and 6 morecytosolOne of 7 routes

• (13Z)-docosenoyl-CoAReach from here →
  1. 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
  2. acetyl-CoA:aralkylamine N-acetyltransferase
  3. long-chain-fatty-acid-CoA ligase (cis-erucic acid)

  Catalysed by DDC, AANAT, SLC27A2, ACSL4 and 6 morecytosolOne of 6 routes

• (11Z)-eicosenoyl-CoAReach from here →
  1. 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
  2. acetyl-CoA:aralkylamine N-acetyltransferase
  3. long-chain-fatty-acid-CoA ligase (cis-gondoic acid)

  Catalysed by DDC, AANAT, SLC27A2, ACSL4 and 6 morecytosolOne of 7 routes

• (9Z,12Z,15Z,18Z,21Z)-tetracosapentaenoyl-CoAReach from here →
  1. 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
  2. acetyl-CoA:aralkylamine N-acetyltransferase
  3. long-chain-fatty-acid-CoA ligase ((9Z,12Z,15Z,18Z,21Z)-TPA)

  Catalysed by DDC, AANAT, SLC27A2, ACSL4 and 6 morecytosolOne of 5 routes

• (6Z,9Z,12Z,15Z,18Z,21Z)-tetracosahexaenoyl-CoAReach from here →
  1. 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
  2. acetyl-CoA:aralkylamine N-acetyltransferase
  3. long-chain-fatty-acid-CoA ligase ((6Z,9Z,12Z,15Z,18Z,21Z)-THA)

  Catalysed by DDC, AANAT, SLC27A2, ACSL4 and 6 morecytosolOne of 4 routes

• (15Z)-tetracosenoyl-CoAReach from here →
  1. 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
  2. acetyl-CoA:aralkylamine N-acetyltransferase
  3. long-chain-fatty-acid-CoA ligase (nervonic acid)

  Catalysed by DDC, AANAT, SLC27A2, ACSL4 and 6 morecytosolOne of 6 routes

• (17Z)-hexacosenoyl-CoAReach from here →
  1. 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
  2. acetyl-CoA:aralkylamine N-acetyltransferase
  3. long-chain-fatty-acid-CoA ligase (ximenic acid)

  Catalysed by DDC, AANAT, SLC27A2, ACSL4 and 6 morecytosolOne of 4 routes

• (8Z,11Z,14Z)-eicosatrienoyl-CoAReach from here →
  1. 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
  2. acetyl-CoA:aralkylamine N-acetyltransferase
  3. long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)

  Catalysed by DDC, AANAT, SLC27A2, ACSL4 and 6 morecytosolOne of 5 routes

• (8Z,11Z,14Z,17Z)-eicosatetraenoyl-CoAReach from here →
  1. 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
  2. acetyl-CoA:aralkylamine N-acetyltransferase
  3. long-chain-fatty-acid-CoA ligase (omega-3-arachidonic acid)

  Catalysed by DDC, AANAT, SLC27A2, ACSL4 and 6 morecytosolOne of 5 routes

• (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoAReach from here →
  1. 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
  2. acetyl-CoA:aralkylamine N-acetyltransferase
  3. long-chain-fatty-acid-CoA ligase (DHA)

  Catalysed by DDC, AANAT, SLC27A2, ACSL4 and 6 morecytosolOne of 7 routes

• heptadecanoyl-CoAReach from here →
  1. 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
  2. acetyl-CoA:aralkylamine N-acetyltransferase
  3. long-chain-fatty-acid-CoA ligase (margaric acid)

  Catalysed by DDC, AANAT, SLC27A2, ACSL4 and 6 morecytosolOne of 6 routes