L-glutamine

Three steps

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

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

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

• 13-hydroxy-(9Z,11E)-octadecadienoateReach from here →
  1. L-Glutamine:pyruvate aminotransferase
  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 KYAT1, MOCOS, PTGS2cytosol

• 9-hydroxy-(10E,12Z)-octadecadienoateReach from here →
  1. L-Glutamine:pyruvate aminotransferase
  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 KYAT1, MOCOS, PTGS2cytosol

• 2,4-dinitrophenyl-S-glutathioneReach from here →
  1. transport of glutamine and glycine (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

• cholesterol sulfateReach from here →
  1. Transport of L-Glutamine by Atb0 Transporter
  2. transport of chloride and sulfate (cytosol to extracellular)
  3. Steryl-Sulfatase

  Catalysed by SLC6A14, SLC26A6, STSextracellular space, cytosol, Golgi apparatusOne of 2 routes

• (13R)-hydroxy-(9Z,11E)-octadecadienoateReach from here →
  1. L-Glutamine:pyruvate aminotransferase
  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 KYAT1, MOCOS, PTGS1, PTGS2cytosol

• 5alpha-dihydrotestosterone sulfateReach from here →
  1. Transport of L-Glutamine by Atb0 Transporter
  2. transport of chloride and sulfate (cytosol to extracellular)
  3. steroid sulfatase (5-alpha-dihydrotestosterone)

  Catalysed by SLC6A14, SLC26A6, STSextracellular space, cytosolOne of 3 routes

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

  Catalysed by KYAT1, AGXT2cytosol, mitochondrial matrixOne of 6 routes

• (13R)-S-glutathionyl-(14S)-hydroxy-(4Z,7Z,9E,11E,16Z,19Z)-docosahexaenoateReach from here →
  1. transport of glutamine 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 SLC7A5, GSS, GSTM4, LTC4Sextracellular space, cytosol

• 2-[(11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoyl]-sn-glycero-3-phosphocholineReach from here →
  1. L-Glutamine:pyruvate aminotransferase
  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 KYAT1, MOCOS, PTGS2cytosol

• 2-[(15R)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoyl]-sn-glycero-3-phosphocholineReach from here →
  1. L-Glutamine:pyruvate aminotransferase
  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 KYAT1, MOCOS, PTGS2cytosol

• 2-[(15S)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoyl]-sn-glycero-3-phosphocholineReach from here →
  1. L-Glutamine:pyruvate aminotransferase
  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 KYAT1, MOCOS, PTGS2cytosol

• 2-(prostaglandin H2)-sn-glycero-3-phosphoethanolamineReach from here →
  1. L-Glutamine:pyruvate aminotransferase
  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 KYAT1, MOCOS, PTGS2cytosol

• 2-(prostaglandin H2)-sn-glycero-3-phosphocholineReach from here →
  1. L-Glutamine:pyruvate aminotransferase
  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 KYAT1, MOCOS, PTGS2cytosol

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

  Catalysed by KYAT1, GGTLC3, GGT1, GGT5 and 4 morecytosol

• 2-hydroxyoctanoyl-CoAReach from here →
  1. Phenylacetyl-CoA:L-glutamine alpha-N-phenylacetyltransferase
  2. Octanoyl-CoA:L-carnitine O-octanoyltransferase
  3. octanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxyoctanoyl-CoA + succinate + CO2

  Catalysed by CROT, PHYHcytosol, mitochondrial matrix

• 2-hydroxydecanoyl-CoAReach from here →
  1. Phenylacetyl-CoA:L-glutamine alpha-N-phenylacetyltransferase
  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 morecytosol

• 2-hydroxyeicosanoyl-CoAReach from here →
  1. Phenylacetyl-CoA:L-glutamine alpha-N-phenylacetyltransferase
  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 morecytosol

• 2-hydroxydodecanoyl-CoAReach from here →
  1. Phenylacetyl-CoA:L-glutamine alpha-N-phenylacetyltransferase
  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 morecytosol

• 2-hydroxytetradecanoyl-CoAReach from here →
  1. Phenylacetyl-CoA:L-glutamine alpha-N-phenylacetyltransferase
  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 morecytosol

• 11-cis-retinyl tetradecanoateReach from here →
  1. Phenylacetyl-CoA:L-glutamine alpha-N-phenylacetyltransferase
  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 morecytosolOne of 2 routes

• 9-cis-retinyl tetradecanoateReach from here →
  1. Phenylacetyl-CoA:L-glutamine alpha-N-phenylacetyltransferase
  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 morecytosol

• 13-cis-retinyl tetradecanoateReach from here →
  1. Phenylacetyl-CoA:L-glutamine alpha-N-phenylacetyltransferase
  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 morecytosol

• all-trans-retinyl tetradecanoateReach from here →
  1. Phenylacetyl-CoA:L-glutamine alpha-N-phenylacetyltransferase
  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 morecytosol

• tetradecyl tetradecanoateReach from here →
  1. Phenylacetyl-CoA:L-glutamine alpha-N-phenylacetyltransferase
  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 morecytosol

• 1-(9Z-octadecenoyl)-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphateReach from here →
  1. Phenylacetyl-CoA:L-glutamine alpha-N-phenylacetyltransferase
  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 morecytosol

• an aryl sulfateReach from here →
  1. Transport of L-Glutamine by Atb0 Transporter
  2. transport of chloride and sulfate (cytosol to extracellular)
  3. an aryl sulfate + H2O = a phenol + sulfate + H(+)

  Catalysed by SLC6A14, SLC26A6, ARSL, ARSF and 4 moreextracellular space, cytosol

• 3-sulfinopyruvateReach from here →
  1. transport of cysteine and glutamine (cytosol to extracellular)
  2. L-Cysteine:oxygen oxidoreductase
  3. 3-sulfino-L-alanine:2-oxoglutarate aminotransferase

  Catalysed by SLC3A2, SLC7A5, SLC7A10, CDO1 and 1 moreextracellular space, cytosolOne of 2 routes

• S-methyl glutathioneReach from here →
  1. transport of glutamine 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 SLC7A5, GSS, MMACHCextracellular space, cytosol

• N-octanoyl-(2S)-hydroxyglycineReach from here →
  1. transport of glutamine and glycine (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

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

  Catalysed by SLC7A5, AADAT, PAMextracellular space, cytosolOne of 2 routes

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

  Catalysed by SLC7A5, AADAT, PAMextracellular space, cytosolOne of 2 routes

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

  Catalysed by SLC7A5, AADAT, PAMextracellular space, cytosolOne of 2 routes

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

  Catalysed by SLC7A5, AADAT, PAMextracellular space, cytosolOne of 2 routes

• N-(9Z,12Z,15Z)-octadecatrienoyl-(2S)-hydroxyglycineReach from here →
  1. transport of glutamine 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 SLC7A5, AADAT, PAMextracellular space, cytosol

• an N-octadecanoyl-sphingoid baseReach from here →
  1. Phenylacetyl-CoA:L-glutamine alpha-N-phenylacetyltransferase
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. a sphingoid base + octadecanoyl-CoA = an N-octadecanoyl-sphingoid base + CoA + H(+)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 4 morecytosol

• 2,3-didehydrophenylalanineReach from here →
  1. transport of glutamine and glycine (cytosol to extracellular)
  2. glycyldehydrophenylalanine + H2O = 2,3-didehydrophenylalanine + glycine
  3. glycyldehydrophenylalanine + H2O = 2,3-didehydrophenylalanine + glycine

  Catalysed by SLC7A5, DPEP1extracellular space, cytosol

• S-adenosylglutathioneReach from here →
  1. transport of glutamine and glycine (cytosol to extracellular)
  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 SLC7A5, GSS, MMACHCextracellular space, cytosol

• N(2)-formyl-N(1)-(5-phospho-beta-D-ribosyl)glycinamideReach from here →
  1. phosphoribosyl pyrophosphate amidotransferase (glutamine)
  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 PPAT, GARTcytosol

• kinetensin-(1-8)Reach from here →
  1. transport of glutamine and phenylalanine (cytosol to extracellular)
  2. Chymase
  3. kinetensin + H2O = kinetensin-(1-8) + L-leucine

  Catalysed by SLC7A5, CMA1, ACE2extracellular space, cytosol

• 1-(10Z-heptadecenoyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. Phenylacetyl-CoA:L-glutamine alpha-N-phenylacetyltransferase
  2. long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)
  3. 1-(10Z-heptadecenoyl)-sn-glycero-3-phosphoethanolamine + (9Z,12Z)-octadecadienoyl-CoA = 1-(10Z-heptadecenoyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphoethanolamine + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 5 morecytosol

• cholesteryl (7Z)-octadecenoateReach from here →
  1. Phenylacetyl-CoA:L-glutamine alpha-N-phenylacetyltransferase
  2. carnitine O-palmitoyltransferase ((7Z)-octadecenoyl-CoA)
  3. (7Z)-octadecenoyl-CoA + cholesterol = cholesteryl (7Z)-octadecenoate + CoA

  Catalysed by CPT1A, CPT1C, CPT1B, SOAT1cytosol

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

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

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

  Catalysed by KYAT1, AGXT2, FAHD1cytosol, mitochondrial matrix

• all-trans-retinoic acidReach from here →
  1. L-Glutamine:pyruvate aminotransferase
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. transport of pyruvate and retinoate (cytosol to extracellular)

  Catalysed by KYAT1, AGXT2, SLC16A4, SLC16A5 and 4 morecytosol, mitochondrial matrix, extracellular spaceOne of 4 routes

• CHEBI:15467Reach from here →
  1. Phenylacetyl-CoA:L-glutamine alpha-N-phenylacetyltransferase
  2. Acetoacetate:CoA ligase (AMP-forming)
  3. 3-hydroxy-3-methylglutaryl-CoA synthase (acetoacetyl-CoA)

  Catalysed by AACS, HMGCS1cytosolOne of 3 routes

• (S)-malateReach from here →
  1. L-Glutamine:pyruvate aminotransferase
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. (S)-malate + NAD(+) = pyruvate + CO2 + NADH

  Catalysed by KYAT1, AGXT2, ME2cytosol, mitochondrial matrixOne of 13 routes

• (6R)-5,10-methylene-5,6,7,8-tetrahydrofolateReach from here →
  1. transport of glutamine and glycine (cytosol to extracellular)
  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 SLC7A5, SHMT1, SHMT2extracellular space, cytosolOne of 2 routes