N-formyl-L-kynurenine

Three steps

• 3-guanidinopropanoateReach from here →
  1. L-tryptophan + O2 = N-formyl-L-kynurenine
  2. transport of arginine and tryptophan (cytosol to extracellular)
  3. beta-alanine + L-arginine = 3-guanidinopropanoate + L-ornithine

  Catalysed by IDO1, TDO2, IDO2, SLC7A6 and 1 moreextracellular space, cytosol

• L-histidineReach from here →
  1. N-formyl-L-kynurenine + H2O = L-kynurenine + formate + H(+)
  2. Transport of L-Kynurenine
  3. L-histidine(in) + L-phenylalanine(out) = L-histidine(out) + L-phenylalanine(in)

  Catalysed by AFMID, SLC7A8extracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 7 routes

• D-ornithineReach from here →
  1. L-tryptophan + O2 = N-formyl-L-kynurenine
  2. transport of ornithine and tryptophan (cytosol to extracellular)
  3. D-ornithine(in) + L-ornithine(out) = D-ornithine(out) + L-ornithine(in)

  Catalysed by IDO1, TDO2, IDO2, SLC7A6 and 1 moreextracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• an N-acylglycineReach from here →
  1. N-formyl-L-kynurenine + H2O = L-kynurenine + formate + H(+)
  2. L-kynurenine + glyoxylate = kynurenate + glycine + H2O
  3. an acyl-CoA + glycine = an N-acylglycine + CoA + H(+)

  Catalysed by AFMID, KYAT3, AADAT, GLYATL3 and 2 more

• 2-oxo-3-sulfanylpropanoateReach from here →
  1. N-formyl-L-kynurenine + H2O = L-kynurenine + formate + H(+)
  2. 2-oxo-3-sulfanylpropanoate + L-kynurenine = kynurenate + L-cysteine + H2O
  3. L-Cysteine:2-oxoglutarate aminotransferase

  Catalysed by AFMID, AADAT, GOT2, GOT1cytosolOne of 3 routes

• guanidinoacetateReach from here →
  1. N-formyl-L-kynurenine + H2O = L-kynurenine + formate + H(+)
  2. L-kynurenine + glyoxylate = kynurenate + glycine + H2O
  3. L-Arginine:glycine amidinotransferase

  Catalysed by AFMID, KYAT3, AADAT, GATMcytosolOne of 5 routes

• D-threonineReach from here →
  1. N-formyl-L-kynurenine + H2O = L-kynurenine + formate + H(+)
  2. L-Kynurenine hydrolase
  3. D-threonine(out) + L-alanine(in) = D-threonine(in) + L-alanine(out)

  Catalysed by AFMID, KYNU, SLC7A10cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• L-dopaquinoneReach from here →
  1. L-tryptophan + O2 = N-formyl-L-kynurenine
  2. transport of tryptophan and tyrosine (cytosol to extracellular)
  3. L-Tyrosine,L-dopa:oxygen oxidoreductase

  Catalysed by IDO1, TDO2, IDO2, SLC7A5 and 1 moreextracellular space, cytosol

• glutathioneReach from here →
  1. N-formyl-L-kynurenine + H2O = L-kynurenine + formate + H(+)
  2. S-formylglutathione + H2O = formate + glutathione + H(+)
  3. S-formylglutathione + H2O = formate + glutathione + H(+)

  Catalysed by AFMID, ESDOne of 2 routes

• L-threonineReach from here →
  1. N-formyl-L-kynurenine + H2O = L-kynurenine + formate + H(+)
  2. L-Kynurenine hydrolase
  3. L-threonine(out) + L-alanine(in) = L-threonine(in) + L-alanine(out)

  Catalysed by AFMID, KYNU, SLC7A10cytosol, inner side of the membrane, outer side of the membraneOne of 8 routes

• L-saccharopineReach from here →
  1. L-tryptophan + O2 = N-formyl-L-kynurenine
  2. transport of lysine and tryptophan (cytosol to extracellular)
  3. N6-(L-1,3-Dicarboxypropyl)-L-lysine:NADP+ oxidoreductase (L-lysine-forming)

  Catalysed by IDO1, TDO2, IDO2, SLC7A6 and 1 moreextracellular space, cytosol, mitochondrial matrix

• beta-alanineReach from here →
  1. N-formyl-L-kynurenine + H2O = L-kynurenine + formate + H(+)
  2. L-Kynurenine hydrolase
  3. beta-alanine(out) + L-alanine(in) = beta-alanine(in) + L-alanine(out)

  Catalysed by AFMID, KYNU, SLC7A10cytosol, inner side of the membrane, outer side of the membraneOne of 6 routes

• leukotriene C4Reach from here →
  1. N-formyl-L-kynurenine + H2O = L-kynurenine + formate + H(+)
  2. L-kynurenine + glyoxylate = kynurenate + glycine + H2O
  3. leukotriene C4 hydrolysis

  Catalysed by AFMID, KYAT3, AADATcytosol

• taurocyamineReach from here →
  1. L-tryptophan + O2 = N-formyl-L-kynurenine
  2. transport of arginine and tryptophan (cytosol to extracellular)
  3. taurine + L-arginine = taurocyamine + L-ornithine

  Catalysed by IDO1, TDO2, IDO2, SLC7A6 and 1 moreextracellular space, cytosol

• L-glutamate 5-semialdehydeReach from here →
  1. L-tryptophan + O2 = N-formyl-L-kynurenine
  2. transport of ornithine and tryptophan (cytosol to extracellular)
  3. L-ornithine + 2-oxoglutarate = L-glutamate 5-semialdehyde + L-glutamate

  Catalysed by IDO1, TDO2, IDO2, SLC7A6 and 1 moreextracellular space, cytosol

• N(4)-(beta-N-acetyl-D-glucosaminyl)-L-asparagineReach from here →
  1. L-tryptophan + O2 = N-formyl-L-kynurenine
  2. L-tryptophan(out) + L-aspartate(in) = L-tryptophan(in) + L-aspartate(out)
  3. N(4)-(beta-N-acetyl-D-glucosaminyl)-L-asparagine + H2O = N-acetyl-beta-D-glucosaminylamine + L-aspartate + H(+)

  Catalysed by IDO1, TDO2, IDO2, SLC7A13 and 1 moreinner side of the membrane, outer side of the membrane

• gamma-L-glutamyl-L-cysteineReach from here →
  1. N-formyl-L-kynurenine + H2O = L-kynurenine + formate + H(+)
  2. 2-oxo-3-sulfanylpropanoate + L-kynurenine = kynurenate + L-cysteine + H2O
  3. L-glutamate:L-cysteine gamma-ligase (ADP-forming)

  Catalysed by AFMID, AADAT, GCLC, GCLMcytosolOne of 2 routes

• 6-amino-2-oxohexanoateReach from here →
  1. L-tryptophan + O2 = N-formyl-L-kynurenine
  2. transport of lysine and tryptophan (cytosol to extracellular)
  3. L-lysine:oxygen 2-oxidoreductase (deaminating)

  Catalysed by IDO1, TDO2, IDO2, SLC7A6extracellular space, cytosol, peroxisome

• L-homocysteineReach from here →
  1. N-formyl-L-kynurenine + H2O = L-kynurenine + formate + H(+)
  2. 4-methylsulfanyl-2-oxobutanoate + L-kynurenine = kynurenate + L-methionine + H2O
  3. S-methyl-L-methionine + L-homocysteine = 2 L-methionine + H(+)

  Catalysed by AFMID, AADAT, BHMT2

• carbamoyl phosphateReach from here →
  1. L-tryptophan + O2 = N-formyl-L-kynurenine
  2. transport of glutamine and tryptophan (cytosol to extracellular)
  3. HCO3-:L-glutamine amido-ligase (ADP-forming, carbamate-phosphorylating)

  Catalysed by IDO1, TDO2, IDO2, SLC7A5 and 1 moreextracellular space, cytosolOne of 4 routes

• S-methyl-L-methionineReach from here →
  1. N-formyl-L-kynurenine + H2O = L-kynurenine + formate + H(+)
  2. 4-methylsulfanyl-2-oxobutanoate + L-kynurenine = kynurenate + L-methionine + H2O
  3. S-methyl-L-methionine + L-homocysteine = 2 L-methionine + H(+)

  Catalysed by AFMID, AADAT, BHMT2

• L-tyrosineReach from here →
  1. N-formyl-L-kynurenine + H2O = L-kynurenine + formate + H(+)
  2. Transport of L-Kynurenine
  3. (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + L-phenylalanine + O2 = (4aS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterin + L-tyrosine

  Catalysed by AFMID, SLC7A8, PAHextracellular space, cytosolOne of 4 routes

• N(omega),N(omega)-dimethyl-L-arginineReach from here →
  1. N-formyl-L-kynurenine + H2O = L-kynurenine + formate + H(+)
  2. L-Kynurenine hydrolase
  3. N(omega),N(omega)-dimethyl-L-arginine + pyruvate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + L-alanine

  Catalysed by AFMID, KYNU, AGXT2cytosolOne of 10 routes

• trans-4-hydroxy-L-prolineReach from here →
  1. N-formyl-L-kynurenine + H2O = L-kynurenine + formate + H(+)
  2. L-Kynurenine hydrolase
  3. trans-4-hydroxy-L-proline(out) + L-alanine(in) + Na(+)(out) = trans-4-hydroxy-L-proline(in) + L-alanine(out) + Na(+)(in)

  Catalysed by AFMID, KYNU, SLC1A4cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• histamineReach from here →
  1. L-tryptophan + O2 = N-formyl-L-kynurenine
  2. transport of histidine and tryptophan (cytosol to extracellular)
  3. L-histidine carboxy-lyase (histamine-forming)

  Catalysed by IDO1, TDO2, IDO2, SLC7A6 and 1 moreextracellular space, cytosol

• (2S)-2-[5-amino-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamido]succinateReach from here →
  1. L-tryptophan + O2 = N-formyl-L-kynurenine
  2. L-tryptophan(out) + L-aspartate(in) = L-tryptophan(in) + L-aspartate(out)
  3. 1-(5-Phosphoribosyl)-5-amino-4-carboxyimidazole:L-aspartate ligase (ADP-forming)

  Catalysed by IDO1, TDO2, IDO2, SLC7A13 and 1 moreinner side of the membrane, outer side of the membrane, cytosolOne of 2 routes

• 5-formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamideReach from here →
  1. N-formyl-L-kynurenine + H2O = L-kynurenine + formate + H(+)
  2. (6S)-5,6,7,8-tetrahydrofolate + formate + ATP = (6R)-10-formyltetrahydrofolate + ADP + phosphate
  3. (6R)-10-formyltetrahydrofolate + 5-amino-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamide = 5-formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide + (6S)-5,6,7,8-tetrahydrofolate

  Catalysed by AFMID, MTHFD1, MTHFD1L, ATIC

• 5-guanidino-2-oxopentanoateReach from here →
  1. L-tryptophan + O2 = N-formyl-L-kynurenine
  2. transport of arginine and tryptophan (cytosol to extracellular)
  3. L-arginine + O2 + H2O = 5-guanidino-2-oxopentanoate + H2O2 + NH4(+)

  Catalysed by IDO1, TDO2, IDO2, SLC7A6 and 1 moreextracellular space, cytosol

• S-sulfanyl-L-cysteineReach from here →
  1. N-formyl-L-kynurenine + H2O = L-kynurenine + formate + H(+)
  2. 2-oxo-3-sulfanylpropanoate + L-kynurenine = kynurenate + L-cysteine + H2O
  3. 2 L-cysteine = S-sulfanyl-L-cysteine + L-alanine

  Catalysed by AFMID, AADAT, CARS2

• 5-phospho-beta-D-ribosylamineReach from here →
  1. L-tryptophan + O2 = N-formyl-L-kynurenine
  2. transport of glutamine and tryptophan (cytosol to extracellular)
  3. phosphoribosyl pyrophosphate amidotransferase (glutamine)

  Catalysed by IDO1, TDO2, IDO2, SLC7A5 and 1 moreextracellular space, cytosolOne of 2 routes

• D-glucosamine 6-phosphateReach from here →
  1. L-tryptophan + O2 = N-formyl-L-kynurenine
  2. transport of glutamine and tryptophan (cytosol to extracellular)
  3. D-fructose 6-phosphate + L-glutamine = D-glucosamine 6-phosphate + L-glutamate

  Catalysed by IDO1, TDO2, IDO2, SLC7A5 and 2 moreextracellular space, cytosol

• L-methionine (S)-S-oxideReach from here →
  1. N-formyl-L-kynurenine + H2O = L-kynurenine + formate + H(+)
  2. 4-methylsulfanyl-2-oxobutanoate + L-kynurenine = kynurenate + L-methionine + H2O
  3. [thioredoxin]-disulfide + L-methionine + H2O = L-methionine (S)-S-oxide + [thioredoxin]-dithiol

  Catalysed by AFMID, AADAT, MSRA

• L-methionine (R)-S-oxideReach from here →
  1. N-formyl-L-kynurenine + H2O = L-kynurenine + formate + H(+)
  2. 4-methylsulfanyl-2-oxobutanoate + L-kynurenine = kynurenate + L-methionine + H2O
  3. [thioredoxin]-disulfide + L-methionine + H2O = L-methionine (R)-S-oxide + [thioredoxin]-dithiol

  Catalysed by AFMID, AADAT, MSRB3, MSRB1 and 1 more

• 5-amino-2-oxopentanoateReach from here →
  1. L-tryptophan + O2 = N-formyl-L-kynurenine
  2. transport of ornithine and tryptophan (cytosol to extracellular)
  3. L-ornithine + pyruvate = 5-amino-2-oxopentanoate + L-alanine

  Catalysed by IDO1, TDO2, IDO2, SLC7A6 and 1 moreextracellular space, cytosolOne of 2 routes

• 5-methylsulfanyl-2,3-dioxopentyl phosphateReach from here →
  1. N-formyl-L-kynurenine + H2O = L-kynurenine + formate + H(+)
  2. 1,2-dihydroxy-5-(methylsulfanyl)pent-1-en-3-one + O2 = 3-(methylsulfanyl)propanoate + CO + formate + 2 H(+)
  3. 5-methylsulfanyl-2,3-dioxopentyl phosphate + H2O = 1,2-dihydroxy-5-(methylsulfanyl)pent-1-en-3-one + phosphate

  Catalysed by AFMID, ADI1, ENOPH1

• N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycineReach from here →
  1. N-formyl-L-kynurenine + H2O = L-kynurenine + formate + H(+)
  2. L-kynurenine + glyoxylate = kynurenate + glycine + H2O
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + glycine = N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycine + CoA + H(+)

  Catalysed by AFMID, KYAT3, AADAT, GLYATL2One of 2 routes

• N-[(R)-4-phosphopantothenoyl]-L-cysteineReach from here →
  1. N-formyl-L-kynurenine + H2O = L-kynurenine + formate + H(+)
  2. 2-oxo-3-sulfanylpropanoate + L-kynurenine = kynurenate + L-cysteine + H2O
  3. (R)-4'-phosphopantothenate:L-cysteine ligase

  Catalysed by AFMID, AADAT, PPCScytosolOne of 4 routes

• (6R)-L-erythro-5,6,7,8-tetrahydrobiopterinReach from here →
  1. L-tryptophan + O2 = N-formyl-L-kynurenine
  2. (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
  3. (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

  Catalysed by IDO1, TDO2, IDO2, TPH1 and 1 moreOne of 3 routes

• an N-acyl-L-amino acidReach from here →
  1. N-formyl-L-kynurenine + H2O = L-kynurenine + formate + H(+)
  2. an L-alpha-amino acid(in) + L-kynurenine(out) = an L-alpha-amino acid(out) + L-kynurenine(in)
  3. an N-acyl-L-amino acid + H2O = an L-alpha-amino acid + a carboxylate

  Catalysed by AFMID, SLC7A11, ACY1, PM20D1inner side of the membrane, outer side of the membrane

• 4-aminobutanoateReach from here →
  1. L-tryptophan + O2 = N-formyl-L-kynurenine
  2. Transport of L-Tryptophan by Atb0 Transporter
  3. transport of 4-aminobutyrate and chloride (cytosol to extracellular)

  Catalysed by IDO1, TDO2, IDO2, SLC6A14 and 1 moreextracellular space, cytosolOne of 4 routes

• 3-iodo-L-tyrosineReach from here →
  1. L-tryptophan + O2 = N-formyl-L-kynurenine
  2. transport of tryptophan and tyrosine (cytosol to extracellular)
  3. thyroid peroxidase (iodine)

  Catalysed by IDO1, TDO2, IDO2, SLC7A5 and 1 moreextracellular space, cytosolOne of 2 routes

• L-prolineReach from here →
  1. N-formyl-L-kynurenine + H2O = L-kynurenine + formate + H(+)
  2. L-Kynurenine hydrolase
  3. L-proline(out) + L-alanine(in) + Na(+)(out) = L-proline(in) + L-alanine(out) + Na(+)(in)

  Catalysed by AFMID, KYNU, SLC1A4cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• N-benzoylglycineReach from here →
  1. N-formyl-L-kynurenine + H2O = L-kynurenine + formate + H(+)
  2. L-kynurenine + glyoxylate = kynurenate + glycine + H2O
  3. Hippurate (Benzoylglycinate) Formation

  Catalysed by AFMID, KYAT3, AADATmitochondrial matrixOne of 2 routes

• 3-sulfino-L-alanineReach from here →
  1. N-formyl-L-kynurenine + H2O = L-kynurenine + formate + H(+)
  2. 2-oxo-3-sulfanylpropanoate + L-kynurenine = kynurenate + L-cysteine + H2O
  3. L-Cysteine:oxygen oxidoreductase

  Catalysed by AFMID, AADAT, CDO1cytosolOne of 6 routes

• L-cysteinylglycineReach from here →
  1. N-formyl-L-kynurenine + H2O = L-kynurenine + formate + H(+)
  2. L-Kynurenine hydrolase
  3. gamma-glutamyltransferase (alanine)

  Catalysed by AFMID, KYNU, GGTLC3, GGT1 and 4 morecytosolOne of 2 routes

• N(5)-[(Z)-amino(hydroxyimino)methyl]ornithineReach from here →
  1. L-tryptophan + O2 = N-formyl-L-kynurenine
  2. transport of arginine and tryptophan (cytosol to extracellular)
  3. L-arginine,NADPH:oxygen oxidoreductase (N-(omega)-hydroxyarginine-forming)

  Catalysed by IDO1, TDO2, IDO2, SLC7A6 and 3 moreextracellular space, cytosol

• xanthurenateReach from here →
  1. N-formyl-L-kynurenine + H2O = L-kynurenine + formate + H(+)
  2. L-Kynurenine,NADPH:oxygen oxidoreductase (3-hydroxylating)
  3. Kynurenine-Oxoglutarate Transaminase

  Catalysed by AFMID, KMO, AADATcytosol, mitochondrial matrixOne of 3 routes

• Mo-molybdopterinReach from here →
  1. N-formyl-L-kynurenine + H2O = L-kynurenine + formate + H(+)
  2. L-Kynurenine hydrolase
  3. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O

  Catalysed by AFMID, KYNU, MOCOScytosol

• an L-aminoacyl-L-amino acidReach from here →
  1. N-formyl-L-kynurenine + H2O = L-kynurenine + formate + H(+)
  2. an L-alpha-amino acid(in) + L-kynurenine(out) = an L-alpha-amino acid(out) + L-kynurenine(in)
  3. an L-aminoacyl-L-amino acid + H2O = 2 an L-alpha-amino acid

  Catalysed by AFMID, SLC7A11, DPEP1, DPEP2inner side of the membrane, outer side of the membrane

• thio-Mo-molybdopterinReach from here →
  1. N-formyl-L-kynurenine + H2O = L-kynurenine + formate + H(+)
  2. 2-oxo-3-sulfanylpropanoate + L-kynurenine = kynurenate + L-cysteine + H2O
  3. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O

  Catalysed by AFMID, AADAT, MOCOS