D-alanine

Three steps

• prostaglandin A2Reach from here →
  1. D-alanine + O2 + H2O = pyruvate + H2O2 + NH4(+)
  2. (S)-Lactate:NAD+ oxidoreductase
  3. Transport of Prostaglandin A2, Lactate Antiport

  Catalysed by DAO, LDHB, LDHAL6Bmitochondrial matrix, extracellular space, cytosolOne of 2 routes

• prostaglandin J2Reach from here →
  1. D-alanine + O2 + H2O = pyruvate + H2O2 + NH4(+)
  2. (S)-Lactate:NAD+ oxidoreductase
  3. Transport of Prostaglandin J2, Lactate Antiport

  Catalysed by DAO, LDHB, LDHAL6Bmitochondrial matrix, extracellular space, cytosolOne of 2 routes

• 15-oxoprostaglandin F2alphaReach from here →
  1. D-alanine + O2 + H2O = pyruvate + H2O2 + NH4(+)
  2. (S)-Lactate:NAD+ oxidoreductase
  3. Transport of 15-Keto-Prostaglandin F2A, Lactate Antiport

  Catalysed by DAO, LDHB, LDHAL6Bmitochondrial matrix, extracellular space, cytosolOne of 2 routes

• 13-hydroxy-(9Z,11E)-octadecadienoateReach from here →
  1. D-alanine(out) + L-alanine(in) = D-alanine(in) + L-alanine(out)
  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 SLC7A10, MOCOS, PTGS2inner side of the membrane, outer side of the membrane

• 9-hydroxy-(10E,12Z)-octadecadienoateReach from here →
  1. D-alanine(out) + L-alanine(in) = D-alanine(in) + L-alanine(out)
  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 SLC7A10, MOCOS, PTGS2inner side of the membrane, outer side of the membrane

• N-(9Z-octadecenoyl)glycineReach from here →
  1. D-alanine(out) + L-alanine(in) = D-alanine(in) + L-alanine(out)
  2. L-Alanine:glyoxylate aminotransferase
  3. (9Z)-octadecenoyl-CoA + glycine = N-(9Z-octadecenoyl)glycine + CoA + H(+)

  Catalysed by SLC7A10, AGXT, AGXT2, GLYATL3 and 1 moreinner side of the membrane, outer side of the membrane, mitochondrial matrix

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

  Catalysed by SLC7A10, SLC7A5, PM20D1inner side of the membrane, outer side of the membrane, extracellular space, cytosol

• N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanineReach from here →
  1. D-alanine(out) + L-alanine(in) = D-alanine(in) + L-alanine(out)
  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 SLC7A10, SLC7A5, PM20D1inner side of the membrane, outer side of the membrane, extracellular space, cytosol

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

  Catalysed by SLC7A10, SLC7A5, PM20D1inner side of the membrane, outer side of the membrane, extracellular space, cytosol

• N-octadecanoylglycineReach from here →
  1. D-alanine(out) + L-alanine(in) = D-alanine(in) + L-alanine(out)
  2. L-Alanine:glyoxylate aminotransferase
  3. octadecanoyl-CoA + glycine = N-octadecanoylglycine + CoA + H(+)

  Catalysed by SLC7A10, AGXT, AGXT2, GLYATL2inner side of the membrane, outer side of the membrane, mitochondrial matrix

• N-(9Z-hexadecenoyl)-glycineReach from here →
  1. D-alanine(out) + L-alanine(in) = D-alanine(in) + L-alanine(out)
  2. L-Alanine:glyoxylate aminotransferase
  3. (9Z)-hexadecenoyl-CoA + glycine = N-(9Z-hexadecenoyl)-glycine + CoA + H(+)

  Catalysed by SLC7A10, AGXT, AGXT2, GLYATL2inner side of the membrane, outer side of the membrane, mitochondrial matrix

• all-trans-4-hydroxyretinoateReach from here →
  1. D-alanine + O2 + H2O = pyruvate + H2O2 + NH4(+)
  2. transport of pyruvate and retinoate (cytosol to extracellular)
  3. cytochrome P450 (retinoate)

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

• N-acetylcadaverineReach from here →
  1. D-alanine + O2 + H2O = pyruvate + H2O2 + NH4(+)
  2. transport of acetate and pyruvate (cytosol to extracellular)
  3. N-acetylcadaverine + H2O = cadaverine + acetate

  Catalysed by DAO, SLC16A4, SLC16A5, SLC16A3 and 3 moreextracellular space, cytosol

• (13R)-hydroxy-(9Z,11E)-octadecadienoateReach from here →
  1. D-alanine(out) + L-alanine(in) = D-alanine(in) + L-alanine(out)
  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 SLC7A10, MOCOS, PTGS1, PTGS2inner side of the membrane, outer side of the membrane

• 2-[(11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoyl]-sn-glycero-3-phosphocholineReach from here →
  1. D-alanine(out) + L-alanine(in) = D-alanine(in) + L-alanine(out)
  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 SLC7A10, MOCOS, PTGS2inner side of the membrane, outer side of the membrane

• 2-[(15R)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoyl]-sn-glycero-3-phosphocholineReach from here →
  1. D-alanine(out) + L-alanine(in) = D-alanine(in) + L-alanine(out)
  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 SLC7A10, MOCOS, PTGS2inner side of the membrane, outer side of the membrane

• 2-[(15S)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoyl]-sn-glycero-3-phosphocholineReach from here →
  1. D-alanine(out) + L-alanine(in) = D-alanine(in) + L-alanine(out)
  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 SLC7A10, MOCOS, PTGS2inner side of the membrane, outer side of the membrane

• 2-(prostaglandin H2)-sn-glycero-3-phosphoethanolamineReach from here →
  1. D-alanine(out) + L-alanine(in) = D-alanine(in) + L-alanine(out)
  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 SLC7A10, MOCOS, PTGS2inner side of the membrane, outer side of the membrane

• 2-(prostaglandin H2)-sn-glycero-3-phosphocholineReach from here →
  1. D-alanine(out) + L-alanine(in) = D-alanine(in) + L-alanine(out)
  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 SLC7A10, MOCOS, PTGS2inner side of the membrane, outer side of the membrane

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

  Catalysed by SLC7A10, GGTLC3, GGT1, GGT5 and 4 moreinner side of the membrane, outer side of the membrane, cytosol

• all-trans-retinoyl-1-O-(beta-D-glucuronate)Reach from here →
  1. D-alanine + O2 + H2O = pyruvate + H2O2 + NH4(+)
  2. transport of pyruvate and retinoate (cytosol to extracellular)
  3. glucuronosyltransferase (retinoate)

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

• all-trans-18-hydroxyretinoateReach from here →
  1. D-alanine + O2 + H2O = pyruvate + H2O2 + NH4(+)
  2. transport of pyruvate and retinoate (cytosol to extracellular)
  3. unspecific monooxygenase (retinoate)

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

• a phenyl acetateReach from here →
  1. D-alanine + O2 + H2O = pyruvate + H2O2 + NH4(+)
  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 moreextracellular space, cytosol

• N-hexadecanoylglycineReach from here →
  1. D-alanine(out) + L-alanine(in) = D-alanine(in) + L-alanine(out)
  2. L-Alanine:glyoxylate aminotransferase
  3. hexadecanoyl-CoA + glycine = N-hexadecanoylglycine + CoA + H(+)

  Catalysed by SLC7A10, AGXT, AGXT2, GLYATL3inner side of the membrane, outer side of the membrane, mitochondrial matrix

• N-dodecanoylglycineReach from here →
  1. D-alanine(out) + L-alanine(in) = D-alanine(in) + L-alanine(out)
  2. L-Alanine:glyoxylate aminotransferase
  3. dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)

  Catalysed by SLC7A10, AGXT, AGXT2, GLYATL2inner side of the membrane, outer side of the membrane, mitochondrial matrix

• N-decanoylglycineReach from here →
  1. D-alanine(out) + L-alanine(in) = D-alanine(in) + L-alanine(out)
  2. L-Alanine:glyoxylate aminotransferase
  3. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)

  Catalysed by SLC7A10, AGXT, AGXT2, GLYATL2inner side of the membrane, outer side of the membrane, mitochondrial matrix

• N-octanoylglycineReach from here →
  1. D-alanine(out) + L-alanine(in) = D-alanine(in) + L-alanine(out)
  2. L-Alanine:glyoxylate aminotransferase
  3. octanoyl-CoA + glycine = N-octanoylglycine + CoA + H(+)

  Catalysed by SLC7A10, AGXT, AGXT2, GLYATL2inner side of the membrane, outer side of the membrane, mitochondrial matrix

• D-histidineReach from here →
  1. D-alanine(out) + L-alanine(in) = D-alanine(in) + L-alanine(out)
  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 SLC7A10, SLC7A6, SLC25A2inner side of the membrane, outer side of the membrane, extracellular space, cytosolOne of 2 routes

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

  Catalysed by SLC7A10, SLC7A6, SLC25A29inner side of the membrane, outer side of the membrane, extracellular space, cytosolOne of 4 routes

• L-homocarnosineReach from here →
  1. D-alanine(out) + L-alanine(in) = D-alanine(in) + L-alanine(out)
  2. transport of alanine and histidine (cytosol to extracellular)
  3. Formation of homocarnosine

  Catalysed by SLC7A10, SLC7A6, CARNS1inner side of the membrane, outer side of the membrane, extracellular space, cytosol

• N(1)-(5-phospho-beta-D-ribosyl)glycinamideReach from here →
  1. D-alanine(out) + L-alanine(in) = D-alanine(in) + L-alanine(out)
  2. L-Alanine:glyoxylate aminotransferase
  3. 5-phospho-beta-D-ribosylamine + glycine + ATP = N(1)-(5-phospho-beta-D-ribosyl)glycinamide + ADP + phosphate + H(+)

  Catalysed by SLC7A10, AGXT, AGXT2, GARTinner side of the membrane, outer side of the membrane, mitochondrial matrix

• L-cystine-bis-glycineReach from here →
  1. D-alanine(out) + L-alanine(in) = D-alanine(in) + L-alanine(out)
  2. L-Alanine:glyoxylate aminotransferase
  3. L-cystine-bis-glycine + 2 H2O = L-cystine + 2 glycine

  Catalysed by SLC7A10, AGXT, AGXT2, DPEP1 and 1 moreinner side of the membrane, outer side of the membrane, mitochondrial matrixOne of 3 routes

• glycyldehydrophenylalanineReach from here →
  1. D-alanine(out) + L-alanine(in) = D-alanine(in) + L-alanine(out)
  2. L-Alanine:glyoxylate aminotransferase
  3. glycyldehydrophenylalanine + H2O = 2,3-didehydrophenylalanine + glycine

  Catalysed by SLC7A10, AGXT, AGXT2, DPEP1inner side of the membrane, outer side of the membrane, mitochondrial matrix

• 2-formamido-N(1)-(5-O-phospho-beta-D-ribosyl)acetamidineReach from here →
  1. D-alanine(out) + L-alanine(in) = D-alanine(in) + L-alanine(out)
  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 SLC7A10, SLC3A2, SLC7A5, PFASinner side of the membrane, outer side of the membrane, extracellular space, cytosol

• kinetensinReach from here →
  1. D-alanine(out) + L-alanine(in) = D-alanine(in) + L-alanine(out)
  2. transport of alanine and phenylalanine (cytosol to extracellular)
  3. Chymase

  Catalysed by SLC7A10, SLC7A5, CMA1inner side of the membrane, outer side of the membrane, extracellular space, cytosolOne of 3 routes

• an N-(fatty acyl)-glycineReach from here →
  1. D-alanine(out) + L-alanine(in) = D-alanine(in) + L-alanine(out)
  2. L-Alanine:glyoxylate aminotransferase
  3. a fatty acyl-CoA + glycine = an N-(fatty acyl)-glycine + CoA + H(+)

  Catalysed by SLC7A10, AGXT, AGXT2, GLYATL2inner side of the membrane, outer side of the membrane, mitochondrial matrix

• N-(9Z,12Z-octadecadienoyl)-glycineReach from here →
  1. D-alanine(out) + L-alanine(in) = D-alanine(in) + L-alanine(out)
  2. L-Alanine:glyoxylate aminotransferase
  3. (9Z,12Z)-octadecadienoyl-CoA + glycine = N-(9Z,12Z-octadecadienoyl)-glycine + CoA + H(+)

  Catalysed by SLC7A10, AGXT, AGXT2, GLYATL2inner side of the membrane, outer side of the membrane, mitochondrial matrix

• (7Z)-octadecenoyl-CoAReach from here →
  1. D-alanine(out) + L-alanine(in) = D-alanine(in) + L-alanine(out)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. carnitine O-palmitoyltransferase ((7Z)-octadecenoyl-CoA)

  Catalysed by SLC7A10, CPT1A, CPT1C, CPT1Binner side of the membrane, outer side of the membrane, mitochondrial matrix, cytosolOne of 3 routes

• acetaldehydeReach from here →
  1. D-alanine(out) + L-alanine(in) = D-alanine(in) + L-alanine(out)
  2. transport of alanine and threonine (cytosol to extracellular)
  3. L-threonine acetaldehyde-lyase (glycine-forming)

  Catalysed by SLC7A10, SLC7A5inner side of the membrane, outer side of the membrane, extracellular space, cytosolOne of 2 routes

• CHEBI:15345Reach from here →
  1. D-alanine + O2 + H2O = pyruvate + H2O2 + NH4(+)
  2. transport of acetoacetate and pyruvate (cytosol to mitochondria)
  3. Acetoacetate:CoA ligase (AMP-forming)

  Catalysed by DAO, AACSmitochondrial matrix, cytosolOne of 5 routes

• acetoneReach from here →
  1. D-alanine + O2 + H2O = pyruvate + H2O2 + NH4(+)
  2. transport of acetoacetate and pyruvate (cytosol to mitochondria)
  3. Acetoacetate carboxy-lyase (acetone-forming)

  Catalysed by DAOmitochondrial matrix, cytosol

• cholineReach from here →
  1. D-alanine(out) + L-alanine(in) = D-alanine(in) + L-alanine(out)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. Acetyl-CoA:choline O-acetyltransferase

  Catalysed by SLC7A10, CHATinner side of the membrane, outer side of the membrane, mitochondrial matrix, nucleusOne of 2 routes

• 4a-hydroxytetrahydrobiopterinReach from here →
  1. D-alanine(out) + L-alanine(in) = D-alanine(in) + L-alanine(out)
  2. transport of alanine and tryptophan (cytosol to extracellular)
  3. L-tryptophan,tetrahydrobiopterin:oxygen oxidoreductase(5-hydroxylating)

  Catalysed by SLC7A10, SLC7A5, TPH1, TPH2inner side of the membrane, outer side of the membrane, extracellular space, cytosolOne of 3 routes

• CHEBI:15380Reach from here →
  1. D-alanine(out) + L-alanine(in) = D-alanine(in) + L-alanine(out)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. 5-aminolevulinate synthase (2-amino-3-oxoadipate)

  Catalysed by SLC7A10, ALAS1, CPNE7inner side of the membrane, outer side of the membrane, mitochondrial matrixOne of 8 routes

• CHEBI:15477Reach from here →
  1. D-alanine(out) + L-alanine(in) = D-alanine(in) + L-alanine(out)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. glycine N-acyltransferase (2-methylbutyryl-CoA)

  Catalysed by SLC7A10, GLYAT, GLYATL2, GLYATL1inner side of the membrane, outer side of the membrane, mitochondrial matrixOne of 2 routes

• 2-methylcrotonoyl-CoAReach from here →
  1. D-alanine(out) + L-alanine(in) = D-alanine(in) + L-alanine(out)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. Production of Tiglylcarnitine

  Catalysed by SLC7A10, CPT1A, CPT1Binner side of the membrane, outer side of the membrane, mitochondrial matrix, cytosolOne of 2 routes

• isobutyryl-CoAReach from here →
  1. D-alanine(out) + L-alanine(in) = D-alanine(in) + L-alanine(out)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. acetyl-CoA C-acyltransferase (3-oxo-4-methyl-pentanoyl-CoA)

  Catalysed by SLC7A10, HADHA, ACAA2, HADHBinner side of the membrane, outer side of the membrane, mitochondrial matrixOne of 3 routes

• 3-methylbut-2-enoyl-CoAReach from here →
  1. D-alanine(out) + L-alanine(in) = D-alanine(in) + L-alanine(out)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. glycine-N-acyltransferase (3-methylcrotonoylglycine)

  Catalysed by SLC7A10, GLYATinner side of the membrane, outer side of the membrane, mitochondrial matrix

• isovaleryl-CoAReach from here →
  1. D-alanine(out) + L-alanine(in) = D-alanine(in) + L-alanine(out)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. glycine N-acyltransferase (isovalerylglycine)

  Catalysed by SLC7A10, GLYAT, GLYATL2, GLYATL1inner side of the membrane, outer side of the membrane, mitochondrial matrixOne of 3 routes

• arachidonoyl-CoAReach from here →
  1. D-alanine(out) + L-alanine(in) = D-alanine(in) + L-alanine(out)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. Arachidonate:CoA ligase (AMP-forming)

  Catalysed by SLC7A10, SLC27A2, ACSL4, ACSL3 and 5 moreinner side of the membrane, outer side of the membrane, mitochondrial matrix, cytosolOne of 11 routes