L-kynurenine

Three steps

• L-homocysteinyl-AMPReach from here →
  1. 4-methylsulfanyl-2-oxobutanoate + L-kynurenine = kynurenate + L-methionine + H2O
  2. S-methyl-L-methionine + L-homocysteine = 2 L-methionine + H(+)
  3. L-homocysteine + ATP + H(+) = L-homocysteinyl-AMP + diphosphate

  Catalysed by AADAT, BHMT2, MARS1

• (4Z,7Z,10Z,13Z)-hexadecatetraenoyl-CoAReach from here →
  1. L-Kynurenine hydrolase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. Fatty Acid Beta Oxidation (C18:4->C16:4), Mitochondrial

  Catalysed by KYNU, HADHA, ACADVL, HADHBcytosol, mitochondrial matrixOne of 3 routes

• (7Z,10Z)-hexadecadienoyl-CoAReach from here →
  1. L-Kynurenine hydrolase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. Fatty Acid Beta Oxidation Trans (C18:2->C16:2), Mitochondrial

  Catalysed by KYNU, HADHA, ACADVL, HADHBcytosol, mitochondrial matrix

• (4Z,7Z)-decadienoyl-CoAReach from here →
  1. L-Kynurenine hydrolase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. Fatty Acid Beta Oxidation (C12:3->C10:2), Mitochondrial

  Catalysed by KYNU, ECHS1, ACAA2, HADHcytosol, mitochondrial matrixOne of 2 routes

• (5Z)-octenoyl-CoAReach from here →
  1. L-Kynurenine hydrolase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. Fatty Acid Beta Oxidation (C10:2->C8:1), Mitochondrial

  Catalysed by KYNU, ECHS1, ACAA2, HADHcytosol, mitochondrial matrixOne of 2 routes

• 3-(glutathion-S-yl)-4-hydroxynonanalReach from here →
  1. L-kynurenine + glyoxylate = kynurenate + glycine + H2O
  2. gamma-L-glutamyl-L-cysteine + glycine + ATP = glutathione + ADP + phosphate + H(+)
  3. (E)-4-hydroxynon-2-enal + glutathione = 3-(glutathion-S-yl)-4-hydroxynonanal

  Catalysed by KYAT3, AADAT, GSS, GSTP1

• glycoursodeoxycholate 3-sulfateReach from here →
  1. L-kynurenine + glyoxylate = kynurenate + glycine + H2O
  2. glycine to glycoursodeoxycholate conversion
  3. glycoursodeoxycholate + 3'-phosphoadenylyl sulfate = glycoursodeoxycholate 3-sulfate + adenosine 3',5'-bisphosphate + H(+)

  Catalysed by KYAT3, AADAT, SULT2A1cytosol

• glycochenodeoxycholate 3-sulfateReach from here →
  1. L-kynurenine + glyoxylate = kynurenate + glycine + H2O
  2. chenodeoxycholoyl-CoA + glycine = glycochenodeoxycholate + CoA + H(+)
  3. glycochenodeoxycholate + 3'-phosphoadenylyl sulfate = glycochenodeoxycholate 3-sulfate + adenosine 3',5'-bisphosphate + H(+)

  Catalysed by KYAT3, AADAT, BAAT, SULT2A1

• deoxycholateReach from here →
  1. L-kynurenine + glyoxylate = kynurenate + glycine + H2O
  2. Glycodeoxycholate amidohydrolase
  3. Glycodeoxycholate amidohydrolase

  Catalysed by KYAT3, AADATcytosol

• a quinolReach from here →
  1. L-Kynurenine hydrolase
  2. trans-4-hydroxy-L-proline(out) + L-alanine(in) + Na(+)(out) = trans-4-hydroxy-L-proline(in) + L-alanine(out) + Na(+)(in)
  3. trans-4-hydroxy-L-proline + a quinone = (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate + a quinol + H(+)

  Catalysed by KYNU, SLC1A4, PRODH2cytosol, inner side of the membrane, outer side of the membraneOne of 4 routes

• hypochlorous acidReach from here →
  1. L-Kynurenine hydrolase
  2. transport of alanine and chloride (cytosol to extracellular)
  3. Peroxidase

  Catalysed by KYNU, SLC6A14, LPOcytosol, extracellular spaceOne of 4 routes

• potassium atomReach from here →
  1. L-Kynurenine hydrolase
  2. transport of alanine and chloride (cytosol to extracellular)
  3. transport of chloride (cytosol to extracellular)

  Catalysed by KYNU, SLC6A14, SLC12A2, SLC12A1cytosol, extracellular spaceOne of 3 routes

• CHEBI:27540Reach from here →
  1. L-Kynurenine hydrolase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. medium-chain acyl-CoA ligase (hexanoic acid)

  Catalysed by KYNU, ACSM4, ACSM1, ACSM2A and 3 morecytosol, mitochondrial matrixOne of 6 routes

• selenomethionineReach from here →
  1. 2-oxobutanoate + L-kynurenine = (2S)-2-aminobutanoate + kynurenate + H2O
  2. (2S)-2-aminobutanoate + glyoxylate = 2-oxobutanoate + glycine
  3. Selenomethionine methanethiol-lyase (deaminating)

  Catalysed by AADAT, AGXT2, CTHcytosol

• CHEBI:27760Reach from here →
  1. L-Kynurenine hydrolase
  2. L-selenocysteine selenide-lyase (L-alanine-forming)
  3. Selenocystathionine Lysteine-lyase (deaminating)

  Catalysed by KYNU, SCLY, CTHcytosolOne of 2 routes

• elaidic acidReach from here →
  1. L-Kynurenine hydrolase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. long-chain-fatty-acid-CoA ligase (elaidate)

  Catalysed by KYNU, SLC27A2, ACSL4, ACSL3 and 5 morecytosol, mitochondrial matrixOne of 5 routes

• 5(S)-HETEReach from here →
  1. L-kynurenine + glyoxylate = kynurenate + glycine + H2O
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. Glutathione: 5-HPETE oxidoreductase

  Catalysed by KYAT3, AADAT, GSS, GPX5 and 8 morecytosolOne of 2 routes

• (2-hydroxyphenyl)acetic acidReach from here →
  1. Transport of L-Kynurenine
  2. Phenylalanine Transaminase, Mitochondrial
  3. Phenylpyruvate:oxygen oxidoreductase (hydroxylating,decarboxylating)

  Catalysed by SLC7A8, GOT2, TAT, HPDextracellular space, cytosol, mitochondrial matrix

• 3-mercaptolactic acidReach from here →
  1. 2-oxo-3-sulfanylpropanoate + L-kynurenine = kynurenate + L-cysteine + H2O
  2. L-Cysteine:2-oxoglutarate aminotransferase
  3. 3-Mercaptolactate:NAD+ oxidoreductase

  Catalysed by AADAT, GOT2, GOT1, LDHB and 3 morecytosol

• CHEBI:28701Reach from here →
  1. L-Kynurenine hydrolase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. Propanoyl-CoA:acetyl-CoA C-acyltransferase

  Catalysed by KYNU, ACAA1, SCP2, MYO5Bcytosol, mitochondrial matrix, peroxisomeOne of 7 routes

• 3-disulfanyl-L-alanineReach from here →
  1. L-Kynurenine hydrolase
  2. Transport of L-Cystine (L-Alanine antiport) by B0, +At Transporter
  3. L-cystine thiocysteine-lyase (deaminating

  Catalysed by KYNU, SLC7A9, SLC3A1, CTHcytosol, extracellular space

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

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

• L-ascorbic acidReach from here →
  1. L-kynurenine + glyoxylate = kynurenate + glycine + H2O
  2. gamma-L-glutamyl-L-cysteine + glycine + ATP = glutathione + ADP + phosphate + H(+)
  3. L-dehydroascorbate + 2 glutathione = glutathione disulfide + L-ascorbate

  Catalysed by KYAT3, AADAT, GSS, CLIC1 and 2 more

• Ca(2+)Reach from here →
  1. 2-oxo-3-sulfanylpropanoate + L-kynurenine = kynurenate + L-cysteine + H2O
  2. K(+)(in) + L-cysteine(out) + 3 Na(+)(out) + H(+)(out) = K(+)(out) + L-cysteine(in) + 3 Na(+)(in) + H(+)(in)
  3. Ca(2+)(out) + K(+)(out) + 4 Na(+)(in) = Ca(2+)(in) + K(+)(in) + 4 Na(+)(out)

  Catalysed by AADAT, SLC1A1, SLC24A1, SLC24A5 and 3 moreinner side of the membrane, outer side of the membraneOne of 2 routes

• 3-methyl-1-hydroxybutylthiamine diphosphateReach from here →
  1. Transport of L-Kynurenine
  2. L-Leucine:2-oxoglutarate aminotransferase
  3. branched chain keto acid dehydrogenase E1 (4-methyl-2-oxopentanoate)

  Catalysed by SLC43A1, BCAT2, BCKDHA, BCKDHBextracellular space, cytosol, mitochondrial matrix

• Asp-tRNA(Asp)Reach from here →
  1. L-Kynurenine hydrolase
  2. oxaloacetate + L-alanine = L-aspartate + pyruvate
  3. L-Aspartate:tRNA(Asp) ligase (AMP-forming)

  Catalysed by KYNU, AGXT2, DARS1cytosol

• Ile-tRNA(Ile)Reach from here →
  1. L-Kynurenine hydrolase
  2. transport of alanine and isoleucine (cytosol to extracellular)
  3. L-Isoleucine:tRNA(Ile) ligase (AMP-forming)

  Catalysed by KYNU, SLC7A5, IARS1cytosol, extracellular space

• Gln-tRNA(Gln)Reach from here →
  1. L-Kynurenine hydrolase
  2. transport of alanine and glutamine (cytosol to extracellular)
  3. L-Glutamine:tRNA(Gln) ligase (AMP-forming)

  Catalysed by KYNU, SLC3A2, SLC7A5, SLC7A10 and 1 morecytosol, extracellular space

• isocyanateReach from here →
  1. L-Kynurenine hydrolase
  2. transport of alanine and citrulline (cytosol to extracellular)
  3. L-citrulline + H(+) = isocyanate + L-ornithine

  Catalysed by KYNU, SLC7A6, LACC1cytosol, extracellular space

• a thiolReach from here →
  1. 2-oxo-3-sulfanylpropanoate + L-kynurenine = kynurenate + L-cysteine + H2O
  2. L-cysteine hydrogen-sulfide-lyase (deaminating
  3. L-cysteinyl-[sulfatase] + 2 a thiol + O2 = an organic disulfide + 3-oxo-L-alanyl-[sulfatase] + hydrogen sulfide + H2O + H(+)

  Catalysed by AADAT, CTH, SUMF1cytosol

• Asn-tRNA(Asn)Reach from here →
  1. L-Kynurenine hydrolase
  2. transport of alanine and asparagine (cytosol to extracellular)
  3. L-Asparagine:tRNA(Asn) ligase (AMP-forming)

  Catalysed by KYNU, SLC7A5, NARS1cytosol, extracellular space

• hydrogenselenideReach from here →
  1. L-Kynurenine hydrolase
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. L-selenocysteine + AH2 = hydrogenselenide + L-alanine + A + H(+)

  Catalysed by KYNU, MOCOS, SCLYcytosol

• cholateReach from here →
  1. L-kynurenine + glyoxylate = kynurenate + glycine + H2O
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. solute carrier organic anion transporter (cholate)

  Catalysed by KYAT3, AADAT, GSS, SLCO1A2 and 1 morecytosol, extracellular spaceOne of 3 routes

• glycolateReach from here →
  1. L-kynurenine + glyoxylate = kynurenate + glycine + H2O
  2. glycine:oxygen oxidoreductase (deaminating)
  3. glycolate:NADP+ oxidoreductase

  Catalysed by KYAT3, AADAT, DAO, GRHPRperoxisome, cytosolOne of 3 routes

• D-aspartateReach from here →
  1. 2-oxo-3-sulfanylpropanoate + L-kynurenine = kynurenate + L-cysteine + H2O
  2. K(+)(in) + L-cysteine(out) + 3 Na(+)(out) + H(+)(out) = K(+)(out) + L-cysteine(in) + 3 Na(+)(in) + H(+)(in)
  3. D-aspartate(out) + K(+)(in) + 3 Na(+)(out) + H(+)(out) = D-aspartate(in) + K(+)(out) + 3 Na(+)(in) + H(+)(in)

  Catalysed by AADAT, SLC1A1, SLC1A7, SLC1A3 and 2 moreinner side of the membrane, outer side of the membraneOne of 2 routes

• acetateReach from here →
  1. L-Kynurenine hydrolase
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. transport of acetate and pyruvate (cytosol to extracellular)

  Catalysed by KYNU, AGXT2, SLC16A4, SLC16A5 and 3 morecytosol, mitochondrial matrix, extracellular spaceOne of 2 routes

• oxalateReach from here →
  1. N-formyl-L-kynurenine + H2O = L-kynurenine + formate + H(+)
  2. N-formyl-L-kynurenine + H2O = L-kynurenine + formate + H(+)
  3. oxalate(in) + formate(out) = oxalate(out) + formate(in)

  Catalysed by AFMID, SLC26A6inner side of the membrane, outer side of the membraneOne of 3 routes

• formic acidReach from here →
  1. L-Kynurenine hydrolase
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. transport of formate and pyruvate (cytosol to extracellular)

  Catalysed by KYNU, AGXT2, SLC16A4, SLC16A5 and 3 morecytosol, mitochondrial matrix, extracellular spaceOne of 5 routes

• propionic acidReach from here →
  1. L-Kynurenine hydrolase
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. transport of propanoate and pyruvate (cytosol to extracellular)

  Catalysed by KYNU, AGXT2, SLC16A4, SLC16A5 and 4 morecytosol, mitochondrial matrix, extracellular spaceOne of 2 routes

• butyric acidReach from here →
  1. L-Kynurenine hydrolase
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. transport of butyrate and pyruvate (cytosol to extracellular)

  Catalysed by KYNU, AGXT2, SLC16A4, SLC16A5 and 4 morecytosol, mitochondrial matrix, extracellular spaceOne of 2 routes

• malonic acidReach from here →
  1. L-Kynurenine hydrolase
  2. transport of alanine and chloride (cytosol to extracellular)
  3. Malonate Transport, Antiport with Chloride

  Catalysed by KYNU, SLC6A14cytosol, extracellular spaceOne of 2 routes

• (9Z)-octadecenoateReach from here →
  1. Transport of L-Kynurenine
  2. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  3. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O

  Catalysed by SLC7A8, PM20D1extracellular space, cytosolOne of 3 routes

• adipic acidReach from here →
  1. Kynurenine-Oxoglutarate Transaminase
  2. kynurenate(out) + glutarate(in) = kynurenate(in) + glutarate(out)
  3. hexanedioate + glutaryl-CoA = hexanedioyl-CoA + glutarate

  Catalysed by KYAT3, AADAT, SLC22A6, SUGCTmitochondrial matrix, inner side of the membrane, outer side of the membrane

• 3-hydroxypyruvic acidReach from here →
  1. L-Kynurenine hydrolase
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. L-Serine:pyruvate aminotransferase

  Catalysed by KYNU, AGXT2, AGXTcytosol, mitochondrial matrixOne of 2 routes

• (indol-3-yl)acetateReach from here →
  1. Kynurenine-Oxoglutarate Transaminase
  2. kynurenate(out) + a dicarboxylate(in) = kynurenate(in) + a dicarboxylate(out)
  3. (indol-3-yl)acetate(out) + a dicarboxylate(in) = (indol-3-yl)acetate(in) + a dicarboxylate(out)

  Catalysed by KYAT3, AADAT, SLC22A8, SLC22A6mitochondrial matrix, inner side of the membrane, outer side of the membraneOne of 2 routes

• an alcoholReach from here →
  1. L-kynurenine + glyoxylate = kynurenate + glycine + H2O
  2. gamma-L-glutamyl-L-cysteine + glycine + ATP = glutathione + ADP + phosphate + H(+)
  3. a hydroperoxide + 2 glutathione = an alcohol + glutathione disulfide + H2O

  Catalysed by KYAT3, AADAT, GSS, CP and 1 more

• (5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. Transport of L-Kynurenine
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O

  Catalysed by SLC7A8, PM20D1extracellular space, cytosolOne of 4 routes

• D-lysineReach from here →
  1. L-Kynurenine hydrolase
  2. transport of alanine and ornithine (cytosol to extracellular)
  3. D-lysine(in) + L-ornithine(out) = D-lysine(out) + L-ornithine(in)

  Catalysed by KYNU, SLC7A6, SLC25A2cytosol, extracellular space, inner side of the membrane, outer side of the membraneOne of 2 routes

• putrescineReach from here →
  1. L-Kynurenine hydrolase
  2. transport of alanine and arginine (cytosol to extracellular)
  3. Putrescine Export via Putrescine/Arginine Antiporter

  Catalysed by KYNU, SLC7A6, SLC3A2, SLC7A7cytosol, extracellular spaceOne of 4 routes

• D-arginineReach from here →
  1. L-Kynurenine hydrolase
  2. transport of alanine and ornithine (cytosol to extracellular)
  3. D-arginine(in) + L-ornithine(out) = D-arginine(out) + L-ornithine(in)

  Catalysed by KYNU, SLC7A6, SLC25A2cytosol, extracellular space, inner side of the membrane, outer side of the membraneOne of 2 routes