CHEBI:15570

Three steps

• (8S)-3',8-cyclo-7,8-dihydroguanosine 5'-triphosphateReach from here →
  1. alanine racemase
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. GTP + AH2 + S-adenosyl-L-methionine = (8S)-3',8-cyclo-7,8-dihydroguanosine 5'-triphosphate + 5'-deoxyadenosine + L-methionine + A + H(+)

  Catalysed by MOCOS, MOCS1cytosol

• a hydroxy polyunsaturated fatty acidReach from here →
  1. transport of D-alanine and glycine (cytosol to extracellular)
  2. gamma-L-glutamyl-L-cysteine + glycine + ATP = glutathione + ADP + phosphate + H(+)
  3. a hydroperoxy polyunsaturated fatty acid + 2 glutathione = a hydroxy polyunsaturated fatty acid + glutathione disulfide + H2O

  Catalysed by SLC3A2, SLC7A10, GSS, GPX1 and 2 moreextracellular space, cytosol

• AReach from here →
  1. alanine racemase
  2. transport of alanine and cysteine (cytosol to extracellular)
  3. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O

  Catalysed by SLC7A5, MOCOScytosol, extracellular spaceOne of 72 routes

• tauroursodeoxycholateReach from here →
  1. transport of D-alanine and glycine (cytosol to extracellular)
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. transport of GSH and tauroursodeoxycholate (cytosol to extracellular)

  Catalysed by SLC3A2, SLC7A10, GSS, SLCO1A2 and 1 moreextracellular space, cytosolOne of 3 routes

• N-(12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoyl-glycineReach from here →
  1. transport of D-alanine and glycine (cytosol to extracellular)
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + glycine = N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycine + CoA + H(+)
  3. N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycine + O2 = N-(12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoyl-glycine

  Catalysed by SLC3A2, SLC7A10, GLYATL2, ALOX15 and 1 moreextracellular space, cytosol

• N-(15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoyl-glycineReach from here →
  1. transport of D-alanine and glycine (cytosol to extracellular)
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + glycine = N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycine + CoA + H(+)
  3. N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycine + O2 = N-(15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoyl-glycine

  Catalysed by SLC3A2, SLC7A10, GLYATL2, ALOX15B and 2 moreextracellular space, cytosol

• (18S)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoateReach from here →
  1. alanine racemase
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18S)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O

  Catalysed by MOCOS, PTGS2cytosol

• (15S)-hydroxy-(5Z,8Z,11Z,13E,17Z)-eicosapentaenoateReach from here →
  1. alanine racemase
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (15S)-hydroxy-(5Z,8Z,11Z,13E,17Z)-eicosapentaenoate + A + H2O

  Catalysed by MOCOS, PTGS2cytosolOne of 2 routes

• (11S,15S)-dihydroxy-14(R)-S-glutathionyl-(5Z,8Z,12E)-eicosatrienoateReach from here →
  1. transport of D-alanine and glycine (cytosol to extracellular)
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. glutathione transferase (GSH)

  Catalysed by SLC3A2, SLC7A10, GSS, PTGES and 20 moreextracellular space, cytosolOne of 5 routes

• prostaglandin E3Reach from here →
  1. transport of D-alanine and glycine (cytosol to extracellular)
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. transport of GSH and prostaglandin E3 (cytosol to extracellular)

  Catalysed by SLC3A2, SLC7A10, GSS, SLCO2A1extracellular space, cytosolOne of 6 routes

• prostaglandin H3Reach from here →
  1. alanine racemase
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. prostaglandin G3 + AH2 = prostaglandin H3 + A + H2O

  Catalysed by MOCOS, PTGS2cytosol

• prostaglandin A2Reach from here →
  1. transport of D-alanine and glycine (cytosol to extracellular)
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. transport of GSH and prostaglandin A2 (cytosol to extracellular)

  Catalysed by SLC3A2, SLC7A10, GSS, SLCO2A1extracellular space, cytosolOne of 4 routes

• prostaglandin B1Reach from here →
  1. transport of D-alanine and glycine (cytosol to extracellular)
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. transport of GSH and prostaglandin B1 (cytosol to extracellular)

  Catalysed by SLC3A2, SLC7A10, GSS, SLCO2A1extracellular space, cytosolOne of 2 routes

• prostaglandin J2Reach from here →
  1. D-alanine:oxygen oxidoreductase (deaminating)
  2. (S)-Lactate:NAD+ oxidoreductase
  3. Transport of Prostaglandin J2, Lactate Antiport

  Catalysed by DAO, LDHB, LDHAL6Bperoxisome, mitochondrial matrix, extracellular space, cytosolOne of 2 routes

• 15-oxoprostaglandin F2alphaReach from here →
  1. D-alanine:oxygen oxidoreductase (deaminating)
  2. (S)-Lactate:NAD+ oxidoreductase
  3. Transport of 15-Keto-Prostaglandin F2A, Lactate Antiport

  Catalysed by DAO, LDHB, LDHAL6Bperoxisome, mitochondrial matrix, extracellular space, cytosolOne of 2 routes

• leukotriene F4Reach from here →
  1. transport of D-alanine and glycine (cytosol to extracellular)
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. transport of GSH and leukotriene F4 (cytosol to extracellular)

  Catalysed by SLC3A2, SLC7A10, GSSextracellular space, cytosolOne of 4 routes

• prostaglandin A2-S-(R)-glutathioneReach from here →
  1. transport of D-alanine and glycine (cytosol to extracellular)
  2. gamma-L-glutamyl-L-cysteine + glycine + ATP = glutathione + ADP + phosphate + H(+)
  3. prostaglandin A2 + glutathione = prostaglandin A2-S-(R)-glutathione

  Catalysed by SLC3A2, SLC7A10, GSS, GSTA1 and 1 moreextracellular space, cytosol

• prostaglandin A2-S-(S)-glutathioneReach from here →
  1. transport of D-alanine and glycine (cytosol to extracellular)
  2. gamma-L-glutamyl-L-cysteine + glycine + ATP = glutathione + ADP + phosphate + H(+)
  3. prostaglandin A2 + glutathione = prostaglandin A2-S-(S)-glutathione

  Catalysed by SLC3A2, SLC7A10, GSS, GSTP1 and 1 moreextracellular space, cytosol

• prostaglandin J2-S-(R)-glutathioneReach from here →
  1. transport of D-alanine and glycine (cytosol to extracellular)
  2. gamma-L-glutamyl-L-cysteine + glycine + ATP = glutathione + ADP + phosphate + H(+)
  3. prostaglandin J2 + glutathione = prostaglandin J2-S-(R)-glutathione

  Catalysed by SLC3A2, SLC7A10, GSS, GSTA1 and 2 moreextracellular space, cytosol

• prostaglandin J2-S-(S)-glutathioneReach from here →
  1. transport of D-alanine and glycine (cytosol to extracellular)
  2. gamma-L-glutamyl-L-cysteine + glycine + ATP = glutathione + ADP + phosphate + H(+)
  3. prostaglandin J2 + glutathione = prostaglandin J2-S-(S)-glutathione

  Catalysed by SLC3A2, SLC7A10, GSS, GSTP1 and 1 moreextracellular space, cytosol

• 13-hydroxy-(9Z,11E)-octadecadienoateReach from here →
  1. alanine racemase
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. (9Z,12Z)-octadecadienoate + AH2 + O2 = 13-hydroxy-(9Z,11E)-octadecadienoate + A + H2O

  Catalysed by MOCOS, PTGS2cytosol

• 9-hydroxy-(10E,12Z)-octadecadienoateReach from here →
  1. alanine racemase
  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 MOCOS, PTGS2cytosol

• 2,4-dinitrophenyl-S-glutathioneReach from here →
  1. transport of D-alanine and glycine (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. solute carrier organic anion transporter (glycocholate)

  Catalysed by SLC3A2, SLC7A10, BAAT, SLCO1A2 and 1 moreextracellular space, cytosol, peroxisomeOne of 11 routes

• N-(9Z-octadecenoyl)-L-phenylalanineReach from here →
  1. alanine racemase
  2. transport of alanine and phenylalanine (cytosol to extracellular)
  3. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O

  Catalysed by SLC7A5, PM20D1cytosol, extracellular space

• N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanineReach from here →
  1. alanine racemase
  2. transport of alanine and phenylalanine (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O

  Catalysed by SLC7A5, PM20D1cytosol, extracellular space

• N-(9Z-octadecenoyl)-L-leucineReach from here →
  1. alanine racemase
  2. transport of alanine and leucine (cytosol to extracellular)
  3. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate

  Catalysed by SLC7A5, PM20D1cytosol, extracellular space

• all-trans-4-hydroxyretinoateReach from here →
  1. D-alanine:oxygen oxidoreductase (deaminating)
  2. transport of pyruvate and retinoate (cytosol to extracellular)
  3. cytochrome P450 (retinoate)

  Catalysed by DAO, SLC16A4, SLC16A5, SLC16A3 and 4 moreperoxisome, extracellular space, cytosolOne of 3 routes

• N-acetylcadaverineReach from here →
  1. D-alanine:oxygen oxidoreductase (deaminating)
  2. transport of acetate and pyruvate (cytosol to extracellular)
  3. N-acetylcadaverine + H2O = cadaverine + acetate

  Catalysed by DAO, SLC16A4, SLC16A5, SLC16A3 and 3 moreperoxisome, extracellular space, cytosol

• (13R)-hydroxy-(9Z,11E)-octadecadienoateReach from here →
  1. alanine racemase
  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 MOCOS, PTGS1, PTGS2cytosol

• (13R)-S-glutathionyl-(14S)-hydroxy-(4Z,7Z,9E,11E,16Z,19Z)-docosahexaenoateReach from here →
  1. transport of D-alanine and glycine (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 SLC3A2, SLC7A10, GSS, GSTM4 and 1 moreextracellular space, cytosol

• 2-[(11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoyl]-sn-glycero-3-phosphocholineReach from here →
  1. alanine racemase
  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 MOCOS, PTGS2cytosol

• 2-[(15R)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoyl]-sn-glycero-3-phosphocholineReach from here →
  1. alanine racemase
  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 MOCOS, PTGS2cytosol

• 2-[(15S)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoyl]-sn-glycero-3-phosphocholineReach from here →
  1. alanine racemase
  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 MOCOS, PTGS2cytosol

• 5-amino-1-(5-phospho-beta-D-ribosyl)imidazoleReach from here →
  1. transport of D-alanine and glutamine (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 SLC3A2, SLC7A10, PFAS, GARTextracellular space, cytosol

• 2-(prostaglandin H2)-sn-glycero-3-phosphoethanolamineReach from here →
  1. alanine racemase
  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 MOCOS, PTGS2cytosol

• 2-(prostaglandin H2)-sn-glycero-3-phosphocholineReach from here →
  1. alanine racemase
  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 MOCOS, PTGS2cytosol

• N-(4-oxoglutaryl)-L-cysteinylglycineReach from here →
  1. alanine racemase
  2. gamma-glutamyltransferase (alanine)
  3. N-(4-oxoglutaryl)-L-cysteinylglycine + H2O = L-cysteinylglycine + 2-oxoglutarate

  Catalysed by GGTLC3, GGT1, GGT5, GGTLC2 and 3 morecytosol

• all-trans-retinoyl-1-O-(beta-D-glucuronate)Reach from here →
  1. D-alanine:oxygen oxidoreductase (deaminating)
  2. transport of pyruvate and retinoate (cytosol to extracellular)
  3. glucuronosyltransferase (retinoate)

  Catalysed by DAO, SLC16A4, SLC16A5, SLC16A3 and 6 moreperoxisome, extracellular space, cytosol, endoplasmic reticulum

• all-trans-18-hydroxyretinoateReach from here →
  1. D-alanine:oxygen oxidoreductase (deaminating)
  2. transport of pyruvate and retinoate (cytosol to extracellular)
  3. unspecific monooxygenase (retinoate)

  Catalysed by DAO, SLC16A4, SLC16A5, SLC16A3 and 28 moreperoxisome, extracellular space, cytosolOne of 2 routes

• a phenyl acetateReach from here →
  1. D-alanine:oxygen oxidoreductase (deaminating)
  2. transport of acetate and pyruvate (cytosol to extracellular)
  3. a phenyl acetate + H2O = a phenol + acetate + H(+)

  Catalysed by DAO, SLC16A4, SLC16A5, SLC16A3 and 5 moreperoxisome, extracellular space, cytosol

• S-methyl glutathioneReach from here →
  1. transport of D-alanine and glycine (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 SLC3A2, SLC7A10, GSS, MMACHCextracellular space, cytosol

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

  Catalysed by SLC3A2, SLC7A10, AADAT, PAMextracellular space, cytosolOne of 2 routes

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

  Catalysed by SLC3A2, SLC7A10, AADAT, PAMextracellular space, cytosolOne of 2 routes

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

  Catalysed by SLC3A2, SLC7A10, AADAT, PAMextracellular space, cytosolOne of 2 routes

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

  Catalysed by SLC3A2, SLC7A10, AADAT, PAMextracellular space, cytosolOne of 2 routes

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

  Catalysed by SLC3A2, SLC7A10, AADAT, PAMextracellular space, cytosolOne of 2 routes

• N-(9Z,12Z,15Z)-octadecatrienoyl-(2S)-hydroxyglycineReach from here →
  1. transport of D-alanine and glycine (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 SLC3A2, SLC7A10, AADAT, PAMextracellular space, cytosol

• D-histidineReach from here →
  1. alanine racemase
  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 SLC7A6, SLC25A2cytosol, extracellular space, inner side of the membrane, outer side of the membraneOne of 2 routes

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

  Catalysed by SLC7A6, SLC25A29cytosol, extracellular space, inner side of the membrane, outer side of the membraneOne of 4 routes

• L-homocarnosineReach from here →
  1. alanine racemase
  2. transport of alanine and histidine (cytosol to extracellular)
  3. Formation of homocarnosine

  Catalysed by SLC7A6, CARNS1cytosol, extracellular space