3-hydroxy-L-kynurenine

Three steps

• N-dodecanoyl-(2S)-hydroxyglycineReach from here →
  1. 3-hydroxy-L-kynurenine + glyoxylate = xanthurenate + glycine + H2O
  2. glycine + 2-oxoglutarate = glyoxylate + L-glutamate
  3. N-dodecanoyl-(2S)-hydroxyglycine = dodecanamide + glyoxylate

  Catalysed by KYAT3, AADAT, PAMOne of 2 routes

• N-tetradecanoyl-(2S)-hydroxyglycineReach from here →
  1. 3-hydroxy-L-kynurenine + glyoxylate = xanthurenate + glycine + H2O
  2. glycine + 2-oxoglutarate = glyoxylate + L-glutamate
  3. N-tetradecanoyl-(2S)-hydroxyglycine = tetradecamide + glyoxylate

  Catalysed by KYAT3, AADAT, PAMOne of 2 routes

• N-(9Z-octadecenoyl)-(2S)-hydroxyglycineReach from here →
  1. 3-hydroxy-L-kynurenine + glyoxylate = xanthurenate + glycine + H2O
  2. glycine + 2-oxoglutarate = glyoxylate + L-glutamate
  3. N-(9Z-octadecenoyl)-(2S)-hydroxyglycine = (9Z)-octadecenamide + glyoxylate

  Catalysed by KYAT3, AADAT, PAMOne of 2 routes

• N-(9Z,12Z,15Z)-octadecatrienoyl-(2S)-hydroxyglycineReach from here →
  1. 3-hydroxy-L-kynurenine + glyoxylate = xanthurenate + glycine + H2O
  2. glycine + 2-oxoglutarate = glyoxylate + L-glutamate
  3. N-(9Z,12Z,15Z)-octadecatrienoyl-(2S)-hydroxyglycine = (9Z,12Z,15Z)-octadecatrienamide + glyoxylate

  Catalysed by KYAT3, AADAT, PAM

• D-histidineReach from here →
  1. 3-hydroxy-L-kynurenine + H2O = 3-hydroxyanthranilate + L-alanine + H(+)
  2. transport of alanine and ornithine (cytosol to extracellular)
  3. D-histidine(in) + L-ornithine(out) + H(+)(in) = D-histidine(out) + L-ornithine(in) + H(+)(out)

  Catalysed by KYNU, SLC7A6, SLC25A2extracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• L-homoarginineReach from here →
  1. 3-hydroxy-L-kynurenine + H2O = 3-hydroxyanthranilate + L-alanine + H(+)
  2. transport of alanine and arginine (cytosol to extracellular)
  3. L-homoarginine(in) + L-arginine(out) = L-homoarginine(out) + L-arginine(in)

  Catalysed by KYNU, SLC7A6, SLC25A29extracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 4 routes

• L-homocarnosineReach from here →
  1. 3-hydroxy-L-kynurenine + H2O = 3-hydroxyanthranilate + L-alanine + H(+)
  2. transport of alanine and histidine (cytosol to extracellular)
  3. Formation of homocarnosine

  Catalysed by KYNU, SLC7A6, CARNS1extracellular space, cytosol

• 2,3-didehydrophenylalanineReach from here →
  1. 3-hydroxy-L-kynurenine + glyoxylate = xanthurenate + glycine + H2O
  2. glycyldehydrophenylalanine + H2O = 2,3-didehydrophenylalanine + glycine
  3. glycyldehydrophenylalanine + H2O = 2,3-didehydrophenylalanine + glycine

  Catalysed by KYAT3, AADAT, DPEP1

• S-adenosylglutathioneReach from here →
  1. 3-hydroxy-L-kynurenine + glyoxylate = xanthurenate + glycine + H2O
  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 KYAT3, AADAT, GSS, MMACHC

• N(2)-formyl-N(1)-(5-phospho-beta-D-ribosyl)glycinamideReach from here →
  1. 3-hydroxy-L-kynurenine + glyoxylate = xanthurenate + glycine + H2O
  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 KYAT3, AADAT, GART

• 2-formamido-N(1)-(5-O-phospho-beta-D-ribosyl)acetamidineReach from here →
  1. 3-hydroxy-L-kynurenine + H2O = 3-hydroxyanthranilate + L-alanine + H(+)
  2. transport of alanine and glutamine (cytosol to extracellular)
  3. 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 KYNU, SLC3A2, SLC7A5, SLC7A10 and 1 moreextracellular space, cytosol

• kinetensinReach from here →
  1. L-kynurenine + NADPH + O2 + H(+) = 3-hydroxy-L-kynurenine + NADP(+) + H2O
  2. Transport of L-Kynurenine
  3. Chymase

  Catalysed by KMO, SLC7A8, CMA1extracellular space, cytosolOne of 3 routes

• (7Z)-octadecenoyl-CoAReach from here →
  1. 3-hydroxy-L-kynurenine + H2O = 3-hydroxyanthranilate + L-alanine + H(+)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. carnitine O-palmitoyltransferase ((7Z)-octadecenoyl-CoA)

  Catalysed by KYNU, CPT1A, CPT1C, CPT1Bmitochondrial matrix, cytosolOne of 3 routes

• acetaldehydeReach from here →
  1. 3-hydroxy-L-kynurenine + H2O = 3-hydroxyanthranilate + L-alanine + H(+)
  2. transport of alanine and threonine (cytosol to extracellular)
  3. L-threonine acetaldehyde-lyase (glycine-forming)

  Catalysed by KYNU, SLC7A5extracellular space, cytosolOne of 2 routes

• CHEBI:15345Reach from here →
  1. 3-hydroxy-L-kynurenine + H2O = 3-hydroxyanthranilate + L-alanine + H(+)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. Acetoacetate:CoA ligase (AMP-forming)

  Catalysed by KYNU, AACSmitochondrial matrix, cytosolOne of 2 routes

• cholineReach from here →
  1. 3-hydroxy-L-kynurenine + H2O = 3-hydroxyanthranilate + L-alanine + H(+)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. Acetyl-CoA:choline O-acetyltransferase

  Catalysed by KYNU, CHATmitochondrial matrix, nucleusOne of 2 routes

• acetylcholineReach from here →
  1. 3-hydroxy-L-kynurenine + glyoxylate = xanthurenate + glycine + H2O
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. transport of acetylcholine and GSH (cytosol to extracellular)

  Catalysed by KYAT3, AADAT, GSS, SLCO1A2 and 1 morecytosol, extracellular spaceOne of 2 routes

• acetylpyruvateReach from here →
  1. 3-hydroxy-L-kynurenine + H2O = 3-hydroxyanthranilate + L-alanine + H(+)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. acetylpyruvate + H2O = acetate + pyruvate + H(+)

  Catalysed by KYNU, AGXT2, FAHD1mitochondrial matrix

• all-trans-retinoic acidReach from here →
  1. 3-hydroxy-L-kynurenine + H2O = 3-hydroxyanthranilate + L-alanine + H(+)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. transport of pyruvate and retinoate (cytosol to extracellular)

  Catalysed by KYNU, AGXT2, SLC16A4, SLC16A5 and 4 moremitochondrial matrix, extracellular space, cytosolOne of 2 routes

• 4a-hydroxytetrahydrobiopterinReach from here →
  1. L-kynurenine + NADPH + O2 + H(+) = 3-hydroxy-L-kynurenine + NADP(+) + H2O
  2. Transport of L-Kynurenine
  3. L-phenylalanine,tetrahydrobiopterin:oxygen oxidoreductase(4-hydroxylating)

  Catalysed by KMO, SLC7A8, PAHextracellular space, cytosolOne of 3 routes

• CHEBI:15380Reach from here →
  1. 3-hydroxy-L-kynurenine + H2O = 3-hydroxyanthranilate + L-alanine + H(+)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. 5-aminolevulinate synthase (2-amino-3-oxoadipate)

  Catalysed by KYNU, ALAS1, CPNE7mitochondrial matrixOne of 8 routes

• CHEBI:15477Reach from here →
  1. 3-hydroxy-L-kynurenine + H2O = 3-hydroxyanthranilate + L-alanine + H(+)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. glycine N-acyltransferase (2-methylbutyryl-CoA)

  Catalysed by KYNU, GLYAT, GLYATL2, GLYATL1mitochondrial matrixOne of 3 routes

• 2-methylcrotonoyl-CoAReach from here →
  1. 3-hydroxy-L-kynurenine + H2O = 3-hydroxyanthranilate + L-alanine + H(+)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. Production of Tiglylcarnitine

  Catalysed by KYNU, CPT1A, CPT1Bmitochondrial matrix, cytosolOne of 2 routes

• isobutyryl-CoAReach from here →
  1. 3-hydroxy-L-kynurenine + H2O = 3-hydroxyanthranilate + L-alanine + H(+)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. acetyl-CoA C-acyltransferase (3-oxo-4-methyl-pentanoyl-CoA)

  Catalysed by KYNU, HADHA, ACAA2, HADHBmitochondrial matrixOne of 3 routes

• 3-methylbut-2-enoyl-CoAReach from here →
  1. 3-hydroxy-L-kynurenine + H2O = 3-hydroxyanthranilate + L-alanine + H(+)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. glycine-N-acyltransferase (3-methylcrotonoylglycine)

  Catalysed by KYNU, GLYATmitochondrial matrix

• isovaleryl-CoAReach from here →
  1. 3-hydroxy-L-kynurenine + H2O = 3-hydroxyanthranilate + L-alanine + H(+)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. glycine N-acyltransferase (isovalerylglycine)

  Catalysed by KYNU, GLYAT, GLYATL2, GLYATL1mitochondrial matrixOne of 3 routes

• arachidonoyl-CoAReach from here →
  1. 3-hydroxy-L-kynurenine + H2O = 3-hydroxyanthranilate + L-alanine + H(+)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. Arachidonate:CoA ligase (AMP-forming)

  Catalysed by KYNU, SLC27A2, ACSL4, ACSL3 and 5 moremitochondrial matrix, cytosolOne of 11 routes

• CHEBI:15519Reach from here →
  1. 3-hydroxy-L-kynurenine + H2O = 3-hydroxyanthranilate + L-alanine + H(+)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. propanoyl-CoA C-acyltransferase

  Catalysed by KYNU, ACAA1, SCP2, MYO5Bmitochondrial matrix, peroxisomeOne of 2 routes

• palmitoyl-CoAReach from here →
  1. 3-hydroxy-L-kynurenine + H2O = 3-hydroxyanthranilate + L-alanine + H(+)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. Palmitate:CoA ligase (AMP-forming)

  Catalysed by KYNU, SLC27A2, ACSL4, ACSL3 and 5 moremitochondrial matrix, cytosolOne of 11 routes

• oleoyl-CoAReach from here →
  1. 3-hydroxy-L-kynurenine + H2O = 3-hydroxyanthranilate + L-alanine + H(+)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. Transport of octadecenoyl-CoA into Mitochondrial Matrix

  Catalysed by KYNU, CPT1A, CPT1C, CPT1Bmitochondrial matrix, cytosolOne of 11 routes

• phenylacetyl-CoAReach from here →
  1. 3-hydroxy-L-kynurenine + H2O = 3-hydroxyanthranilate + L-alanine + H(+)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. Phenylacetate:CoA ligase

  Catalysed by KYNUmitochondrial matrix, cytosolOne of 4 routes

• propionyl-CoAReach from here →
  1. 3-hydroxy-L-kynurenine + H2O = 3-hydroxyanthranilate + L-alanine + H(+)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. Propanoate:CoA ligase (AMP-forming)

  Catalysed by KYNU, ACSS3, ACSS2, ACSS1mitochondrial matrix, cytosolOne of 43 routes

• (S)-malateReach from here →
  1. 3-hydroxy-L-kynurenine + H2O = 3-hydroxyanthranilate + L-alanine + H(+)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. (S)-malate + NAD(+) = pyruvate + CO2 + NADH

  Catalysed by KYNU, AGXT2, ME2mitochondrial matrixOne of 4 routes

• (6R)-5,10-methylene-5,6,7,8-tetrahydrofolateReach from here →
  1. 3-hydroxy-L-kynurenine + glyoxylate = xanthurenate + glycine + H2O
  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 KYAT3, AADAT, SHMT1, SHMT2One of 2 routes

• 10-formyltetrahydrofolic acidReach from here →
  1. 3-hydroxy-L-kynurenine + glyoxylate = xanthurenate + glycine + H2O
  2. 5,10-Methylenetetrahydrofolate:glycine hydroxymethyltransferase
  3. Formate:tetrahydrofolate ligase (ADP-forming)

  Catalysed by KYAT3, AADAT, SHMT1, MTHFD1cytosolOne of 3 routes

• 5-methyltetrahydrofolic acidReach from here →
  1. 3-hydroxy-L-kynurenine + glyoxylate = xanthurenate + glycine + H2O
  2. 5,10-Methylenetetrahydrofolate:glycine hydroxymethyltransferase
  3. histamine N-methyltransferase (SAM)

  Catalysed by KYAT3, AADAT, SHMT1, HNMTcytosol

• (4aS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterinReach from here →
  1. L-kynurenine + NADPH + O2 + H(+) = 3-hydroxy-L-kynurenine + NADP(+) + H2O
  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 KMO, SLC7A8, PAHextracellular space, cytosolOne of 3 routes

• CHEBI:15650Reach from here →
  1. 3-hydroxy-L-kynurenine + H2O = 3-hydroxyanthranilate + L-alanine + H(+)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. N-acetyl-LTE4 to leukotriene E4 conversion

  Catalysed by KYNU, ZDHHC11B, NAA10, ESCO2 and 29 moremitochondrial matrix, cytosolOne of 6 routes

• trimethylenediamineReach from here →
  1. 3-hydroxy-L-kynurenine + H2O = 3-hydroxyanthranilate + L-alanine + H(+)
  2. transport of alanine and lysine (cytosol to extracellular)
  3. deoxyhypusine synthase (1,3-diaminopropane)

  Catalysed by KYNU, SLC7A6, DHPSextracellular space, cytosol

• CHEBI:15727Reach from here →
  1. 3-hydroxy-L-kynurenine + H2O = 3-hydroxyanthranilate + L-alanine + H(+)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. N-alpha-acetyltransferase 10, NatA catalytic subunit (acetylcarnosine)

  Catalysed by KYNU, NAA10mitochondrial matrix, cytosolOne of 3 routes

• formateReach from here →
  1. L-kynurenine + NADPH + O2 + H(+) = 3-hydroxy-L-kynurenine + NADP(+) + H2O
  2. N-formyl-L-kynurenine + H2O = L-kynurenine + formate + H(+)
  3. N-formyl-L-kynurenine + H2O = L-kynurenine + formate + H(+)

  Catalysed by KMO, AFMID

• CHEBI:15746Reach from here →
  1. 3-hydroxy-L-kynurenine + H2O = 3-hydroxyanthranilate + L-alanine + H(+)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. diamine N-acetyltransferase (N1-acetylspermine)

  Catalysed by KYNU, SAT1, SAT2mitochondrial matrix, cytosolOne of 2 routes

• CHEBI:15765Reach from here →
  1. L-kynurenine + NADPH + O2 + H(+) = 3-hydroxy-L-kynurenine + NADP(+) + H2O
  2. Transport of L-Kynurenine
  3. solute carrier (L-dopa)

  Catalysed by KMO, SLC43A1, SLC3A2, SLC7A5extracellular space, cytosolOne of 5 routes

• 4-(2-amino-3-hydroxyphenyl)-2,4-dioxobutanoateReach from here →
  1. L-kynurenine + NADPH + O2 + H(+) = 3-hydroxy-L-kynurenine + NADP(+) + H2O
  2. L-Kynurenine,NADPH:oxygen oxidoreductase (3-hydroxylating)
  3. 3-hydroxy-L-kynurenine:2-oxoglutarate aminotransferase

  Catalysed by KMO, KYAT1, KYAT3, AADATcytosol

• 3-hydroxyanthranilic acidReach from here →
  1. L-kynurenine + NADPH + O2 + H(+) = 3-hydroxy-L-kynurenine + NADP(+) + H2O
  2. L-Kynurenine,NADPH:oxygen oxidoreductase (3-hydroxylating)
  3. 3-Hydroxy-L-kynurenine hydrolase

  Catalysed by KMO, KYNUcytosol

• bromideReach from here →
  1. 3-hydroxy-L-kynurenine + glyoxylate = xanthurenate + glycine + H2O
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. 2-bromoacetaldehyde:glutathione S-(formylmethyl)transferase

  Catalysed by KYAT3, AADAT, GSS, MGST3 and 16 morecytosolOne of 2 routes

• N-carbamoyl-L-aspartic acidReach from here →
  1. 3-hydroxy-L-kynurenine + H2O = 3-hydroxyanthranilate + L-alanine + H(+)
  2. oxaloacetate + L-alanine = L-aspartate + pyruvate
  3. carbamoyl-phosphate:L-aspartate carbamoyltransferase

  Catalysed by KYNU, AGXT2, CADcytosol

• alpha-D-glucosamine 6-phosphateReach from here →
  1. 3-hydroxy-L-kynurenine + H2O = 3-hydroxyanthranilate + L-alanine + H(+)
  2. transport of alanine and glutamine (cytosol to extracellular)
  3. L-glutamine:D-fructose-6-phosphate isomerase (deaminating)

  Catalysed by KYNU, SLC3A2, SLC7A5, SLC7A10 and 2 moreextracellular space, cytosol

• thioredoxin dithiolReach from here →
  1. 3-hydroxy-L-kynurenine + H2O = 3-hydroxyanthranilate + L-alanine + H(+)
  2. L-Alanine:tRNA(Ala) ligase (AMP-forming)
  3. glycyl-tRNA(gly) phosphorylation

  Catalysed by KYNU, AARS1cytosolOne of 4 routes

• a halide anionReach from here →
  1. 3-hydroxy-L-kynurenine + glyoxylate = xanthurenate + glycine + H2O
  2. gamma-L-glutamyl-L-cysteine + glycine + ATP = glutathione + ADP + phosphate + H(+)
  3. RX + glutathione = an S-substituted glutathione + a halide anion + H(+)

  Catalysed by KYAT3, AADAT, GSS, GSTT4 and 22 more