5-hydroxy-L-tryptophan

Three steps

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

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

• (11Z,14Z,17Z)-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 ((11Z,14Z,17Z)-eicosatrienoic acid)

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

• (2S)-2-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 glycine and tryptophan (cytosol to extracellular)
  3. (2S)-2-aminobutanoate + glyoxylate = 2-oxobutanoate + glycine

  Catalysed by TPH1, TPH2, SLC7A5, AGXT2extracellular space, cytosolOne of 2 routes

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

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

• (11Z)-octadecenoyl-CoAReach from here →
  1. 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
  2. acetyl-CoA:aralkylamine N-acetyltransferase
  3. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix

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

• dodecanedioyl-CoAReach from here →
  1. 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
  2. acetyl-CoA:aralkylamine N-acetyltransferase
  3. Activation of dodecanedioic acid

  Catalysed by DDC, AANATcytosolOne of 4 routes

• decanedioyl-CoAReach from here →
  1. 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
  2. acetyl-CoA:aralkylamine N-acetyltransferase
  3. Production of Sebacoylcarnitine

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

• octanedioyl-CoAReach from here →
  1. 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
  2. acetyl-CoA:aralkylamine N-acetyltransferase
  3. Production of Suberylcarnitine

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

• hexanedioyl-CoAReach from here →
  1. 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
  2. acetyl-CoA:aralkylamine N-acetyltransferase
  3. Activation of adipic acid for Formation of Adipoyl Carnitine

  Catalysed by DDC, AANATcytosolOne of 4 routes

• (4Z,7Z,10Z,13Z,16Z)-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 ((4Z,7Z,10Z,13Z,16Z)-DPA)

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

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

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

• (R)-3-hydroxy-(11Z)-octadecenoyl-CoAReach from here →
  1. 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
  2. acetyl-CoA:aralkylamine N-acetyltransferase
  3. Production of 3-Hydroxyoctadecenoylcarnitinec

  Catalysed by DDC, AANAT, CPT1A, CPT1C and 1 morecytosol

• (13Z)-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 ((13Z)-eicosenoic acid)

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

• 20-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
  2. transport of serotonin (cytosol to extracellular)
  3. Resistance-Nodulation-Cell Division (Rnd) Tcdb:2.A.60.1.5

  Catalysed by DDC, SLCO1A2, SLCO1B3, SLCO1B1extracellular space, cytosolOne of 4 routes

• 4,8-dimethylnonanoyl-CoAReach from here →
  1. 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
  2. acetyl-CoA:aralkylamine N-acetyltransferase
  3. Carnitine Dimethyl Nonanoyl Transferase, Revsible, Peroxisomal

  Catalysed by DDC, AANAT, CRAT, CROTcytosol, peroxisomeOne of 3 routes

• tetradecanedioyl-CoAReach from here →
  1. 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
  2. acetyl-CoA:aralkylamine N-acetyltransferase
  3. Fatty Acid Beta Oxidation (C16Dc->C14Dc), Peroxisomal

  Catalysed by DDC, AANAT, ACAA1, HSD17B4 and 2 morecytosol, peroxisome

• hexadecanedioyl-CoAReach from here →
  1. 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
  2. acetyl-CoA:aralkylamine N-acetyltransferase
  3. Production of Hexadecanedioylcarnitine

  Catalysed by DDC, AANAT, CPT1A, CPT1C and 1 morecytosolOne of 2 routes

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

  Catalysed by DDC, AANAT, SLC27A2cytosolOne of 2 routes

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

  Catalysed by DDC, AANAT, ACSM4, ACSM1 and 4 morecytosolOne of 3 routes

• ursodeoxycholateReach 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

• prostaglandin G2Reach from here →
  1. 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
  2. transport of serotonin (cytosol to extracellular)
  3. transport of prostaglandin G2 (cytosol to extracellular)

  Catalysed by DDC, SLCO1A2, SLCO1B3, SLCO1B1extracellular space, cytosolOne of 4 routes

• thio-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 cysteine 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

• glycodeoxycholateReach 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. Glycodeoxycholate amidohydrolase

  Catalysed by TPH1, TPH2, SLC7A5extracellular space, cytosolOne of 2 routes

• 1-O-(1,2-saturated-alkyl)-sn-glycerolReach 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. 1-O-(1,2-saturated-alkyl)-sn-glycerol + (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + O2 = a 1-(1-hydroxyalkyl)-sn-glycerol + (6R)-L-erythro-6,7-dihydrobiopterin + H2O
  3. 1-O-(1,2-saturated-alkyl)-sn-glycerol + (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + O2 = a 1-(1-hydroxyalkyl)-sn-glycerol + (6R)-L-erythro-6,7-dihydrobiopterin + H2O

  Catalysed by TPH1, TPH2, AGMOOne of 2 routes

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

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

• (3E)-decenoyl-CoAReach from here →
  1. 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
  2. acetyl-CoA:aralkylamine N-acetyltransferase
  3. Fatty Acid Beta Oxidation (C12:1->C10:1), Mitochondrial

  Catalysed by DDC, AANAT, ACADM, ECHS1 and 2 morecytosol, mitochondrial matrix

• N-tetradecanoylglycineReach 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. tetradecanoyl-CoA + glycine = N-tetradecanoylglycine + CoA + H(+)

  Catalysed by TPH1, TPH2, SLC7A5, GLYATL2extracellular space, cytosol

• (2R,6)-dimethylheptanoyl-CoAReach from here →
  1. 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
  2. acetyl-CoA:aralkylamine N-acetyltransferase
  3. acetyl-CoA C-acyltransferase (3-oxo-4(R),8-dimethyl-nonanoyl-CoA)

  Catalysed by DDC, AANAT, HADHA, ACAA2 and 1 morecytosol, mitochondrial matrix

• N-eicosanoylglycinateReach 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. eicosanoyl-CoA + glycine = N-eicosanoylglycinate + CoA + H(+)

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

• N-docosanoylglycineReach 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. docosanoyl-CoA + glycine = N-docosanoylglycine + CoA + H(+)

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

• N-hexacosanoylglycineReach 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. hexacosanoyl-CoA + glycine = N-hexacosanoylglycine + CoA + H(+)

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

• an N(2)-acyl-L-glutamineReach 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. an acyl-CoA + L-glutamine = an N(2)-acyl-L-glutamine + CoA + H(+)

  Catalysed by TPH1, TPH2, SLC7A5, GLYATL1B and 1 moreextracellular space, cytosol

• (7Z)-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 (7-palmitoleic acid)

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

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

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

• thromboxane B2Reach 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, SLCO1B3, SLCO1B1extracellular space, cytosolOne of 4 routes

• taurochenodeoxycholateReach from here →
  1. 5-hydroxy-L-tryptophan + H(+) = serotonin + CO2
  2. transport of serotonin (cytosol to extracellular)
  3. solute carrier organic anion transporter (S-glutathionyl-2-4-dinitrobenzene)

  Catalysed by DDC, SLCO1A2, SLCO1B3, SLC7A9extracellular space, cytosolOne of 4 routes