CHEBI:15699

Three steps

• S-butanoyl-4'-phosphopantetheineReach from here →
  1. Acetylation of Homoserine
  2. Butanoate:CoA ligase (AMP-forming)
  3. butanoyl-CoA + H2O = S-butanoyl-4'-phosphopantetheine + adenosine 3',5'-bisphosphate + 2 H(+)

  Catalysed by ACSM4, ACSM1, ACSM2A, ACSM3 and 5 moremitochondrial matrix, cytosol

• S-octanoyl-4'-phosphopantetheineReach from here →
  1. Acetylation of Homoserine
  2. Octanoyl-CoA:L-carnitine O-octanoyltransferase
  3. octanoyl-CoA + H2O = S-octanoyl-4'-phosphopantetheine + adenosine 3',5'-bisphosphate + 2 H(+)

  Catalysed by CROT, NUDT19, NUDT7, NUDT8mitochondrial matrix

• decanoyl-4'-phosphopantetheineReach from here →
  1. Acetylation of Homoserine
  2. medium-chain acyl-CoA ligase (decanoic acid)
  3. decanoyl-CoA + H2O = decanoyl-4'-phosphopantetheine + adenosine 3',5'-bisphosphate + 2 H(+)

  Catalysed by ACSM4, ACSM1, ACSM2A, ACSM3 and 3 moremitochondrial matrix, cytosol

• S-dodecanoyl-4'-phosphopantetheineReach from here →
  1. Acetylation of Homoserine
  2. long-chain-fatty-acid-CoA ligase (lauric acid)
  3. dodecanoyl-CoA + H2O = S-dodecanoyl-4'-phosphopantetheine + adenosine 3',5'-bisphosphate + 2 H(+)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 moremitochondrial matrix, cytosol

• tetradecanoyl-4'-phosphopantetheineReach from here →
  1. Acetylation of Homoserine
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. tetradecanoyl-CoA + H2O = tetradecanoyl-4'-phosphopantetheine + adenosine 3',5'-bisphosphate + 2 H(+)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 moremitochondrial matrix, cytosol

• an acyl-4'-phosphopantetheineReach from here →
  1. Acetylation of Homoserine
  2. acyl-CoA:sphingosine N-acyltransferase
  3. an acyl-CoA + H2O = an acyl-4'-phosphopantetheine + adenosine 3',5'-bisphosphate + 2 H(+)

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 3 moremitochondrial matrix, Golgi apparatus

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

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

• N-(12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoyl-glycineReach from here →
  1. transport of glycine and homoserine (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 SLC7A5, GLYATL2, ALOX15, ALOX12extracellular space, cytosol

• N-(15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoyl-glycineReach from here →
  1. transport of glycine and homoserine (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 SLC7A5, GLYATL2, ALOX15B, ALOX15 and 1 moreextracellular space, cytosol

• (18S)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoateReach from here →
  1. transport of alanine and homoserine (cytosol to extracellular)
  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 SLC7A5, MOCOS, PTGS2extracellular space, cytosol

• (15S)-hydroxy-(5Z,8Z,11Z,13E,17Z)-eicosapentaenoateReach from here →
  1. transport of glycine and homoserine (cytosol to extracellular)
  2. gamma-L-glutamyl-L-cysteine + glycine + ATP = glutathione + ADP + phosphate + H(+)
  3. (15S)-hydroperoxy-(5Z,8Z,11Z,13E,17Z)-eicosapentaenoate + 2 glutathione = (15S)-hydroxy-(5Z,8Z,11Z,13E,17Z)-eicosapentaenoate + glutathione disulfide + H2O

  Catalysed by SLC7A5, GSS, GPX1, GPX4extracellular space, cytosolOne of 2 routes

• a quinoneReach from here →
  1. transport of homoserine and proline (cytosol to extracellular)
  2. L-proline:(acceptor) oxidoreductase
  3. L-proline + a quinone = (S)-1-pyrroline-5-carboxylate + a quinol + H(+)

  Catalysed by PRODH2, PRODHextracellular space, cytosol

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

  Catalysed by SLC7A5, GSS, PTGES, MGST3 and 19 moreextracellular space, cytosolOne of 5 routes

• prostaglandin E3Reach from here →
  1. transport of glycine and homoserine (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 SLC7A5, GSS, SLCO2A1extracellular space, cytosolOne of 2 routes

• prostaglandin H3Reach from here →
  1. transport of alanine and homoserine (cytosol to extracellular)
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. prostaglandin G3 + AH2 = prostaglandin H3 + A + H2O

  Catalysed by SLC7A5, MOCOS, PTGS2extracellular space, cytosol

• prostaglandin A2Reach from here →
  1. transport of glycine and homoserine (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 SLC7A5, GSS, SLCO2A1extracellular space, cytosolOne of 2 routes

• prostaglandin B1Reach from here →
  1. transport of glycine and homoserine (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 SLC7A5, GSS, SLCO2A1extracellular space, cytosolOne of 2 routes

• leukotriene F4Reach from here →
  1. transport of glycine and homoserine (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 SLC7A5, GSSextracellular space, cytosolOne of 5 routes

• epsilon-(gamma-L-glutamyl)-L-lysineReach from here →
  1. transport of homoserine and leucine (cytosol to extracellular)
  2. L-lysine(in) + L-leucine(out) + Na(+)(out) = L-lysine(out) + L-leucine(in) + Na(+)(in)
  3. epsilon-(gamma-L-glutamyl)-L-lysine = 5-oxo-L-proline + L-lysine

  Catalysed by SLC7A5, SLC7A7, GGACTextracellular space, cytosol, inner side of the membrane, outer side of the membrane

• prostaglandin A2-S-(R)-glutathioneReach from here →
  1. transport of glycine and homoserine (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 SLC7A5, GSS, GSTA1, GSTM1extracellular space, cytosol

• prostaglandin A2-S-(S)-glutathioneReach from here →
  1. transport of glycine and homoserine (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 SLC7A5, GSS, GSTP1, GSTM1extracellular space, cytosol

• prostaglandin J2-S-(R)-glutathioneReach from here →
  1. transport of glycine and homoserine (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 SLC7A5, GSS, GSTA1, GSTP1 and 1 moreextracellular space, cytosol

• prostaglandin J2-S-(S)-glutathioneReach from here →
  1. transport of glycine and homoserine (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 SLC7A5, GSS, GSTP1, GSTM1extracellular space, cytosol

• 13-hydroxy-(9Z,11E)-octadecadienoateReach from here →
  1. transport of alanine and homoserine (cytosol to extracellular)
  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 SLC7A5, MOCOS, PTGS2extracellular space, cytosol

• 9-hydroxy-(10E,12Z)-octadecadienoateReach from here →
  1. transport of alanine and homoserine (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. transport of glycine and homoserine (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. solute carrier organic anion transporter (glycocholate)

  Catalysed by SLC7A5, BAAT, SLCO1A2, SLCO1B3extracellular space, cytosol, peroxisomeOne of 15 routes

• (13R)-hydroxy-(9Z,11E)-octadecadienoateReach from here →
  1. transport of alanine and homoserine (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

• acetoacetateReach from here →
  1. transport of alanine and homoserine (cytosol to extracellular)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. transport of acetoacetate and pyruvate (cytosol to mitochondria)

  Catalysed by SLC7A5, AGXT2extracellular space, cytosol, mitochondrial matrixOne of 4 routes

• (13R)-S-glutathionyl-(14S)-hydroxy-(4Z,7Z,9E,11E,16Z,19Z)-docosahexaenoateReach from here →
  1. transport of glycine and homoserine (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 homoserine (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 homoserine (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 homoserine (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 homoserine (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 homoserine (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 homoserine (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 homoserine (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

• 2-hydroxyoctanoyl-CoAReach from here →
  1. Acetylation of Homoserine
  2. Octanoyl-CoA:L-carnitine O-octanoyltransferase
  3. octanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxyoctanoyl-CoA + succinate + CO2

  Catalysed by CROT, PHYHmitochondrial matrix

• 2-hydroxydecanoyl-CoAReach from here →
  1. Acetylation of Homoserine
  2. medium-chain acyl-CoA ligase (decanoic acid)
  3. decanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxydecanoyl-CoA + succinate + CO2

  Catalysed by ACSM4, ACSM1, ACSM2A, ACSM3 and 3 moremitochondrial matrix, cytosol

• 2-hydroxyeicosanoyl-CoAReach from here →
  1. Acetylation of Homoserine
  2. long-chain-fatty-acid-CoA ligase (eicosanoate)
  3. eicosanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxyeicosanoyl-CoA + succinate + CO2

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 5 moremitochondrial matrix, cytosol

• 2-hydroxydodecanoyl-CoAReach from here →
  1. Acetylation of Homoserine
  2. long-chain-fatty-acid-CoA ligase (lauric acid)
  3. dodecanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxydodecanoyl-CoA + succinate + CO2

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 5 moremitochondrial matrix, cytosol

• 2-hydroxytetradecanoyl-CoAReach from here →
  1. Acetylation of Homoserine
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. tetradecanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxytetradecanoyl-CoA + succinate + CO2

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 5 moremitochondrial matrix, cytosol

• 11-cis-retinyl tetradecanoateReach from here →
  1. Acetylation of Homoserine
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. 11-cis-retinol + tetradecanoyl-CoA = 11-cis-retinyl tetradecanoate + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 5 moremitochondrial matrix, cytosolOne of 2 routes

• 9-cis-retinyl tetradecanoateReach from here →
  1. Acetylation of Homoserine
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. 9-cis-retinol + tetradecanoyl-CoA = 9-cis-retinyl tetradecanoate + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 5 moremitochondrial matrix, cytosol

• 13-cis-retinyl tetradecanoateReach from here →
  1. Acetylation of Homoserine
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. 13-cis-retinol + tetradecanoyl-CoA = 13-cis-retinyl tetradecanoate + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 5 moremitochondrial matrix, cytosol

• all-trans-retinyl tetradecanoateReach from here →
  1. Acetylation of Homoserine
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. all-trans-retinol + tetradecanoyl-CoA = all-trans-retinyl tetradecanoate + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 5 moremitochondrial matrix, cytosol

• tetradecyl tetradecanoateReach from here →
  1. Acetylation of Homoserine
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. tetradecan-1-ol + tetradecanoyl-CoA = tetradecyl tetradecanoate + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 5 moremitochondrial matrix, cytosol

• 1-(9Z-octadecenoyl)-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphateReach from here →
  1. Acetylation of Homoserine
  2. long-chain-fatty-acid-CoA ligase (DHA)
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA + 1-(9Z-octadecenoyl)-sn-glycero-3-phosphate = 1-(9Z-octadecenoyl)-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphate + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 5 moremitochondrial matrix, cytosol

• 3-sulfinopyruvateReach from here →
  1. transport of cysteine and homoserine (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 homoserine (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 homoserine (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