L-tryptophan

Three steps

• 9-hydroxy-(10E,12Z)-octadecadienoateReach from here →
  1. transport of alanine and tryptophan (cytosol to extracellular)
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. (9Z,12Z)-octadecadienoate + AH2 + O2 = 9-hydroxy-(10E,12Z)-octadecadienoate + A + H2O

  Catalysed by SLC7A5, MOCOS, PTGS2extracellular space, cytosol

• 2,4-dinitrophenyl-S-glutathioneReach from here →
  1. L-Tryptophan, Tetrahydrobiopterin:Oxygen Oxidoreductase (5-Hydroxylating)
  2. 5-Hydroxy-L-tryptophan decarboxy-lyase
  3. transport of serotonin (cytosol to extracellular)

  Catalysed by TPH1, TPH2, DDC, SLCO1A2 and 1 morecytosol, extracellular spaceOne of 15 routes

• cholesterol sulfateReach from here →
  1. Transport of L-Tryptophan by Atb0 Transporter
  2. transport of chloride and sulfate (cytosol to extracellular)
  3. Steryl-Sulfatase

  Catalysed by SLC6A14, SLC26A6, STSextracellular space, cytosol, Golgi apparatusOne of 2 routes

• (13R)-hydroxy-(9Z,11E)-octadecadienoateReach from here →
  1. transport of alanine and tryptophan (cytosol to extracellular)
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. (9Z,12Z)-octadecadienoate + AH2 + O2 = (13R)-hydroxy-(9Z,11E)-octadecadienoate + A + H2O

  Catalysed by SLC7A5, MOCOS, PTGS1, PTGS2extracellular space, cytosol

• 5alpha-dihydrotestosterone sulfateReach from here →
  1. Transport of L-Tryptophan by Atb0 Transporter
  2. transport of chloride and sulfate (cytosol to extracellular)
  3. steroid sulfatase (5-alpha-dihydrotestosterone)

  Catalysed by SLC6A14, SLC26A6, STSextracellular space, cytosolOne of 3 routes

• acetoacetateReach from here →
  1. L-tryptophan:oxygen 2,3-oxidoreductase (decyclizing)
  2. arylformamidase (L-formylkynurenine)
  3. transport of acetoacetate and formate (cytosol to extracellular)

  Catalysed by IDO1, TDO2, IDO2, AFMID and 2 morecytosol, extracellular spaceOne of 6 routes

• (13R)-S-glutathionyl-(14S)-hydroxy-(4Z,7Z,9E,11E,16Z,19Z)-docosahexaenoateReach from here →
  1. transport of glycine and tryptophan (cytosol to extracellular)
  2. gamma-L-glutamyl-L-cysteine + glycine + ATP = glutathione + ADP + phosphate + H(+)
  3. (13S,14S)-epoxy-(4Z,7Z,9E,11E,16Z,19Z)-docosahexaenoate + glutathione = (13R)-S-glutathionyl-(14S)-hydroxy-(4Z,7Z,9E,11E,16Z,19Z)-docosahexaenoate

  Catalysed by SLC7A5, GSS, GSTM4, LTC4Sextracellular space, cytosol

• 2-[(11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoyl]-sn-glycero-3-phosphocholineReach from here →
  1. transport of alanine and tryptophan (cytosol to extracellular)
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. 2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine + AH2 + O2 = 2-[(11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoyl]-sn-glycero-3-phosphocholine + A + H2O

  Catalysed by SLC7A5, MOCOS, PTGS2extracellular space, cytosol

• 2-[(15R)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoyl]-sn-glycero-3-phosphocholineReach from here →
  1. transport of alanine and tryptophan (cytosol to extracellular)
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. 2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine + AH2 + O2 = 2-[(15R)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoyl]-sn-glycero-3-phosphocholine + A + H2O

  Catalysed by SLC7A5, MOCOS, PTGS2extracellular space, cytosol

• 2-[(15S)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoyl]-sn-glycero-3-phosphocholineReach from here →
  1. transport of alanine and tryptophan (cytosol to extracellular)
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. 2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine + AH2 + O2 = 2-[(15S)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoyl]-sn-glycero-3-phosphocholine + A + H2O

  Catalysed by SLC7A5, MOCOS, PTGS2extracellular space, cytosol

• 5-amino-1-(5-phospho-beta-D-ribosyl)imidazoleReach from here →
  1. transport of glutamine and tryptophan (cytosol to extracellular)
  2. 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(+)
  3. 2-formamido-N(1)-(5-O-phospho-beta-D-ribosyl)acetamidine + ATP = 5-amino-1-(5-phospho-beta-D-ribosyl)imidazole + ADP + phosphate + H(+)

  Catalysed by SLC7A5, PFAS, GARTextracellular space, cytosol

• 2-(prostaglandin H2)-sn-glycero-3-phosphoethanolamineReach from here →
  1. transport of alanine and tryptophan (cytosol to extracellular)
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. 2-(prostaglandin G2)-sn-glycero-3-phosphoethanolamine + AH2 = 2-(prostaglandin H2)-sn-glycero-3-phosphoethanolamine + A + H2O

  Catalysed by SLC7A5, MOCOS, PTGS2extracellular space, cytosol

• 2-(prostaglandin H2)-sn-glycero-3-phosphocholineReach from here →
  1. transport of alanine and tryptophan (cytosol to extracellular)
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. 2-(prostaglandin G2)-sn-glycero-3-phosphocholine + AH2 = 2-(prostaglandin H2)-sn-glycero-3-phosphocholine + A + H2O

  Catalysed by SLC7A5, MOCOS, PTGS2extracellular space, cytosol

• N-(4-oxoglutaryl)-L-cysteinylglycineReach from here →
  1. transport of alanine and tryptophan (cytosol to extracellular)
  2. gamma-glutamyltransferase (alanine)
  3. N-(4-oxoglutaryl)-L-cysteinylglycine + H2O = L-cysteinylglycine + 2-oxoglutarate

  Catalysed by SLC7A5, GGTLC3, GGT1, GGT5 and 4 moreextracellular space, cytosol

• an aryl sulfateReach from here →
  1. Transport of L-Tryptophan by Atb0 Transporter
  2. transport of chloride and sulfate (cytosol to extracellular)
  3. an aryl sulfate + H2O = a phenol + sulfate + H(+)

  Catalysed by SLC6A14, SLC26A6, ARSL, ARSF and 4 moreextracellular space, cytosol

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

  Catalysed by SLC7A5, CDO1, GOT1extracellular space, cytosolOne of 2 routes

• S-methyl glutathioneReach from here →
  1. transport of glycine and tryptophan (cytosol to extracellular)
  2. gamma-L-glutamyl-L-cysteine + glycine + ATP = glutathione + ADP + phosphate + H(+)
  3. apo-[alkylcobalamin reductase] + methylcob(III)alamin + glutathione = S-methyl glutathione + cob(I)alamin-[alkylcobalamin reductase] + H(+)

  Catalysed by SLC7A5, GSS, MMACHCextracellular space, cytosol

• N-octanoyl-(2S)-hydroxyglycineReach from here →
  1. transport of glycine and tryptophan (cytosol to extracellular)
  2. glycine + 2-oxoglutarate = glyoxylate + L-glutamate
  3. N-octanoyl-(2S)-hydroxyglycine = octanamide + glyoxylate

  Catalysed by SLC7A5, AADAT, PAMextracellular space, cytosolOne of 2 routes

• N-decanoyl-(2S)-hydroxyglycineReach from here →
  1. transport of glycine and tryptophan (cytosol to extracellular)
  2. glycine + 2-oxoglutarate = glyoxylate + L-glutamate
  3. N-decanoyl-(2S)-hydroxyglycine = decanamide + glyoxylate

  Catalysed by SLC7A5, AADAT, PAMextracellular space, cytosolOne of 2 routes

• N-dodecanoyl-(2S)-hydroxyglycineReach from here →
  1. transport of glycine and tryptophan (cytosol to extracellular)
  2. glycine + 2-oxoglutarate = glyoxylate + L-glutamate
  3. N-dodecanoyl-(2S)-hydroxyglycine = dodecanamide + glyoxylate

  Catalysed by SLC7A5, AADAT, PAMextracellular space, cytosolOne of 2 routes

• N-tetradecanoyl-(2S)-hydroxyglycineReach from here →
  1. transport of glycine and tryptophan (cytosol to extracellular)
  2. glycine + 2-oxoglutarate = glyoxylate + L-glutamate
  3. N-tetradecanoyl-(2S)-hydroxyglycine = tetradecamide + glyoxylate

  Catalysed by SLC7A5, AADAT, PAMextracellular space, cytosolOne of 2 routes

• N-(9Z-octadecenoyl)-(2S)-hydroxyglycineReach from here →
  1. transport of glycine and tryptophan (cytosol to extracellular)
  2. glycine + 2-oxoglutarate = glyoxylate + L-glutamate
  3. N-(9Z-octadecenoyl)-(2S)-hydroxyglycine = (9Z)-octadecenamide + glyoxylate

  Catalysed by SLC7A5, AADAT, PAMextracellular space, cytosolOne of 2 routes

• N-(9Z,12Z,15Z)-octadecatrienoyl-(2S)-hydroxyglycineReach from here →
  1. transport of glycine and tryptophan (cytosol to extracellular)
  2. glycine + 2-oxoglutarate = glyoxylate + L-glutamate
  3. N-(9Z,12Z,15Z)-octadecatrienoyl-(2S)-hydroxyglycine = (9Z,12Z,15Z)-octadecatrienamide + glyoxylate

  Catalysed by SLC7A5, AADAT, PAMextracellular space, cytosol

• 2-amino-2-deoxy-6-phospho-D-glucono-1,5-lactoneReach from here →
  1. transport of glutamine and tryptophan (cytosol to extracellular)
  2. D-fructose 6-phosphate + L-glutamine = D-glucosamine 6-phosphate + L-glutamate
  3. D-glucosamine 6-phosphate + NADP(+) = 2-amino-2-deoxy-6-phospho-D-glucono-1,5-lactone + NADPH + 2 H(+)

  Catalysed by SLC7A5, GFPT2, GFPT1, H6PDextracellular space, cytosol

• 2,3-didehydrophenylalanineReach from here →
  1. transport of glycine and tryptophan (cytosol to extracellular)
  2. glycyldehydrophenylalanine + H2O = 2,3-didehydrophenylalanine + glycine
  3. glycyldehydrophenylalanine + H2O = 2,3-didehydrophenylalanine + glycine

  Catalysed by SLC7A5, DPEP1extracellular space, cytosol

• S-adenosylglutathioneReach from here →
  1. transport of glycine and tryptophan (cytosol to extracellular)
  2. gamma-L-glutamyl-L-cysteine + glycine + ATP = glutathione + ADP + phosphate + H(+)
  3. apo-[alkylcobalamin reductase] + adenosylcob(III)alamin + glutathione = S-adenosylglutathione + cob(I)alamin-[alkylcobalamin reductase] + H(+)

  Catalysed by SLC7A5, GSS, MMACHCextracellular space, cytosol

• N(2)-formyl-N(1)-(5-phospho-beta-D-ribosyl)glycinamideReach from here →
  1. transport of glycine and tryptophan (cytosol to extracellular)
  2. 5-phospho-beta-D-ribosylamine + glycine + ATP = N(1)-(5-phospho-beta-D-ribosyl)glycinamide + ADP + phosphate + H(+)
  3. N(1)-(5-phospho-beta-D-ribosyl)glycinamide + (6R)-10-formyltetrahydrofolate = N(2)-formyl-N(1)-(5-phospho-beta-D-ribosyl)glycinamide + (6S)-5,6,7,8-tetrahydrofolate + H(+)

  Catalysed by SLC7A5, GARTextracellular space, cytosol

• kinetensin-(1-8)Reach from here →
  1. transport of phenylalanine and tryptophan (cytosol to extracellular)
  2. Chymase
  3. kinetensin + H2O = kinetensin-(1-8) + L-leucine

  Catalysed by SLC7A5, CMA1, ACE2extracellular space, cytosol

• (7Z)-octadecenoyl-CoAReach from here →
  1. transport of glycine and tryptophan (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. carnitine O-palmitoyltransferase ((7Z)-octadecenoyl-CoA)

  Catalysed by SLC7A5, BAAT, CPT1A, CPT1C and 1 moreextracellular space, cytosol, peroxisomeOne of 3 routes

• CHEBI:15345Reach from here →
  1. transport of glycine and tryptophan (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Acetoacetate:CoA ligase (AMP-forming)

  Catalysed by SLC7A5, BAAT, AACSextracellular space, cytosol, peroxisomeOne of 2 routes

• acetylcholineReach from here →
  1. transport of glycine and tryptophan (cytosol to extracellular)
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. transport of acetylcholine and GSH (cytosol to extracellular)

  Catalysed by SLC7A5, GSS, SLCO1A2, SLCO1B3extracellular space, cytosolOne of 5 routes

• acetylpyruvateReach from here →
  1. transport of alanine and tryptophan (cytosol to extracellular)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. acetylpyruvate + H2O = acetate + pyruvate + H(+)

  Catalysed by SLC7A5, AGXT2, FAHD1extracellular space, cytosol, mitochondrial matrix

• all-trans-retinoic acidReach from here →
  1. L-tryptophan:oxygen 2,3-oxidoreductase (decyclizing)
  2. arylformamidase (L-formylkynurenine)
  3. transport of formate and retinoate (cytosol to extracellular)

  Catalysed by IDO1, TDO2, IDO2, AFMID and 2 morecytosol, extracellular spaceOne of 4 routes

• CHEBI:15380Reach from here →
  1. transport of glycine and tryptophan (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. 5-aminolevulinate synthase (2-amino-3-oxoadipate)

  Catalysed by SLC7A5, BAAT, ALAS1, CPNE7extracellular space, cytosol, peroxisome, mitochondrial matrixOne of 8 routes

• CHEBI:15477Reach from here →
  1. transport of glycine and tryptophan (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. glycine N-acyltransferase (2-methylbutyryl-CoA)

  Catalysed by SLC7A5, BAAT, GLYAT, GLYATL2 and 1 moreextracellular space, cytosol, peroxisome, mitochondrial matrixOne of 3 routes

• 2-methylcrotonoyl-CoAReach from here →
  1. transport of glycine and tryptophan (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Production of Tiglylcarnitine

  Catalysed by SLC7A5, BAAT, CPT1A, CPT1Bextracellular space, cytosol, peroxisomeOne of 2 routes

• isobutyryl-CoAReach from here →
  1. transport of glycine and tryptophan (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. acetyl-CoA C-acyltransferase (3-oxo-4-methyl-pentanoyl-CoA)

  Catalysed by SLC7A5, BAAT, HADHA, ACAA2 and 1 moreextracellular space, cytosol, peroxisome, mitochondrial matrixOne of 3 routes

• 3-methylbut-2-enoyl-CoAReach from here →
  1. transport of glycine and tryptophan (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. glycine-N-acyltransferase (3-methylcrotonoylglycine)

  Catalysed by SLC7A5, BAAT, GLYATextracellular space, cytosol, peroxisome, mitochondrial matrix

• isovaleryl-CoAReach from here →
  1. transport of glycine and tryptophan (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. glycine N-acyltransferase (isovalerylglycine)

  Catalysed by SLC7A5, BAAT, GLYAT, GLYATL2 and 1 moreextracellular space, cytosol, peroxisome, mitochondrial matrixOne of 3 routes

• arachidonoyl-CoAReach from here →
  1. transport of glycine and tryptophan (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Arachidonate:CoA ligase (AMP-forming)

  Catalysed by SLC7A5, BAAT, SLC27A2, ACSL4 and 6 moreextracellular space, cytosol, peroxisomeOne of 11 routes

• CHEBI:15519Reach from here →
  1. transport of glycine and tryptophan (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. propanoyl-CoA C-acyltransferase

  Catalysed by SLC7A5, BAAT, ACAA1, SCP2 and 1 moreextracellular space, cytosol, peroxisomeOne of 2 routes

• palmitoyl-CoAReach from here →
  1. transport of glycine and tryptophan (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Palmitate:CoA ligase (AMP-forming)

  Catalysed by SLC7A5, BAAT, SLC27A2, ACSL4 and 6 moreextracellular space, cytosol, peroxisomeOne of 11 routes

• oleoyl-CoAReach from here →
  1. transport of glycine and tryptophan (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Transport of octadecenoyl-CoA into Mitochondrial Matrix

  Catalysed by SLC7A5, BAAT, CPT1A, CPT1C and 1 moreextracellular space, cytosol, peroxisomeOne of 11 routes

• phenylacetyl-CoAReach from here →
  1. transport of glycine and tryptophan (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Phenylacetate:CoA ligase

  Catalysed by SLC7A5, BAATextracellular space, cytosol, peroxisomeOne of 4 routes

• propionyl-CoAReach from here →
  1. transport of glycine and tryptophan (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Propanoate:CoA ligase (AMP-forming)

  Catalysed by SLC7A5, BAAT, ACSS3, ACSS2 and 1 moreextracellular space, cytosol, peroxisomeOne of 46 routes

• (S)-malateReach from here →
  1. transport of glycine and tryptophan (cytosol to extracellular)
  2. glycine:oxygen oxidoreductase (deaminating)
  3. acetyl-CoA[m] + glyoxalate[m] + H2O[m] = CoA[m] + H+[m] + malate[m]

  Catalysed by SLC7A5, DAO, CLYBLextracellular space, cytosol, peroxisome, mitochondrial matrixOne of 13 routes

• (6R)-5,10-methylene-5,6,7,8-tetrahydrofolateReach from here →
  1. transport of glycine and tryptophan (cytosol to extracellular)
  2. (6R)-5,10-methylene-5,6,7,8-tetrahydrofolate + glycine + H2O = (6S)-5,6,7,8-tetrahydrofolate + L-serine
  3. (6R)-5,10-methylene-5,6,7,8-tetrahydrofolate + glycine + H2O = (6S)-5,6,7,8-tetrahydrofolate + L-serine

  Catalysed by SLC7A5, SHMT1, SHMT2extracellular space, cytosolOne of 2 routes

• 10-formyltetrahydrofolic acidReach from here →
  1. L-tryptophan:oxygen 2,3-oxidoreductase (decyclizing)
  2. arylformamidase (L-formylkynurenine)
  3. Formate:tetrahydrofolate ligase (ADP-forming)

  Catalysed by IDO1, TDO2, IDO2, AFMID and 1 morecytosolOne of 5 routes

• 5-methyltetrahydrofolic acidReach from here →
  1. transport of glycine and tryptophan (cytosol to extracellular)
  2. 5,10-Methylenetetrahydrofolate:glycine hydroxymethyltransferase
  3. histamine N-methyltransferase (SAM)

  Catalysed by SLC7A5, SHMT1, HNMTextracellular space, cytosol

• CHEBI:15650Reach from here →
  1. transport of glycine and tryptophan (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. N-acetyl-LTE4 to leukotriene E4 conversion

  Catalysed by SLC7A5, BAAT, ZDHHC11B, NAA10 and 30 moreextracellular space, cytosol, peroxisomeOne of 6 routes