CHEBI:15570

Three steps

• 4-guanidinobutanoateReach from here →
  1. alanine racemase
  2. transport of alanine and arginine (cytosol to extracellular)
  3. 4-aminobutanoate + L-arginine = 4-guanidinobutanoate + L-ornithine

  Catalysed by SLC7A6, GATMcytosol, extracellular space

• 2-oxoadipateReach from here →
  1. transport of D-alanine and glycine (cytosol to extracellular)
  2. glycine + 2-oxoglutarate = glyoxylate + L-glutamate
  3. L-2-aminoadipate + glyoxylate = 2-oxoadipate + glycine

  Catalysed by SLC3A2, SLC7A10, AADATextracellular space, cytosol

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

  Catalysed by SLC7A5, SLC7A8cytosol, extracellular space, inner side of the membrane, outer side of the membraneOne of 3 routes

• N-acetyl-D-glucosamine 6-phosphateReach from here →
  1. transport of D-alanine and glutamine (cytosol to extracellular)
  2. L-glutamine:D-fructose-6-phosphate isomerase (deaminating)
  3. acetyl-CoA:D-glucosamine-6-phosphate N-acetyltransferase

  Catalysed by SLC3A2, SLC7A10, GFPT2, GFPT1 and 1 moreextracellular space, cytosolOne of 4 routes

• N(6)-(1,2-dicarboxyethyl)-AMPReach from here →
  1. alanine racemase
  2. oxaloacetate + L-alanine = L-aspartate + pyruvate
  3. IMP:L-aspartate ligase (GDP-forming)

  Catalysed by AGXT2, ADSS2, ADSS1cytosolOne of 2 routes

• 3-guanidinopropanoateReach from here →
  1. alanine racemase
  2. transport of alanine and arginine (cytosol to extracellular)
  3. beta-alanine + L-arginine = 3-guanidinopropanoate + L-ornithine

  Catalysed by SLC7A6, GATMcytosol, extracellular spaceOne of 2 routes

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

  Catalysed by SLC7A5, SLC7A8cytosol, extracellular space, inner side of the membrane, outer side of the membraneOne of 7 routes

• beta-D-fructose 6-phosphateReach from here →
  1. transport of D-alanine and glutamine (cytosol to extracellular)
  2. L-glutamine:D-fructose-6-phosphate isomerase (deaminating)
  3. alpha-D-glucosamine 6-phosphate + H2O = beta-D-fructose 6-phosphate + NH4(+)

  Catalysed by SLC3A2, SLC7A10, GFPT2, GFPT1 and 2 moreextracellular space, cytosol

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

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

• S-formylglutathioneReach from here →
  1. transport of D-alanine and glycine (cytosol to extracellular)
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. alcohol dehydrogenase (formaldehyde)

  Catalysed by SLC3A2, SLC7A10, GSS, ADH1C and 5 moreextracellular space, cytosolOne of 2 routes

• sphing-4-enineReach from here →
  1. alanine racemase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. acyl-CoA:sphingosine N-acyltransferase

  Catalysed by ASAH1, ACER2, ACER1, ASAH2cytosol, mitochondrial matrix, Golgi apparatusOne of 2 routes

• CMP-N-acetyl-beta-neuraminateReach from here →
  1. D-alanine:oxygen oxidoreductase (deaminating)
  2. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)
  3. CTP:N-acetylneuraminate cytidylyltransferase

  Catalysed by DAO, NPL, CMASperoxisome, cytosol, nucleusOne of 2 routes

• spermidineReach from here →
  1. alanine racemase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. diamine N-acetyltransferase (N1-acetylspermidine)

  Catalysed by SAT1, SAT2cytosol, mitochondrial matrixOne of 3 routes

• L-dopaquinoneReach from here →
  1. alanine racemase
  2. transport of alanine and tyrosine (cytosol to extracellular)
  3. L-Tyrosine,L-dopa:oxygen oxidoreductase

  Catalysed by SLC7A5, TYRcytosol, extracellular spaceOne of 2 routes

• L-saccharopineReach from here →
  1. alanine racemase
  2. transport of alanine and lysine (cytosol to extracellular)
  3. N6-(L-1,3-Dicarboxypropyl)-L-lysine:NADP+ oxidoreductase (L-lysine-forming)

  Catalysed by SLC7A6, AASScytosol, extracellular space, mitochondrial matrix

• 2-hydroxy-3-oxopropanoateReach from here →
  1. D-alanine:oxygen oxidoreductase (deaminating)
  2. L-Serine:pyruvate aminotransferase
  3. hydroxypyruvate aldose-ketose-isomerase

  Catalysed by DAO, AGXT, HYIperoxisome, cytosolOne of 2 routes

• dimethylamineReach from here →
  1. alanine racemase
  2. N(omega),N(omega)-dimethyl-L-arginine + pyruvate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + L-alanine
  3. Nomega,Nomega'-dimethyl-L-arginine dimethylamidohydrolase

  Catalysed by AGXT2, DDAH1cytosolOne of 2 routes

• taurocyamineReach from here →
  1. alanine racemase
  2. transport of alanine and arginine (cytosol to extracellular)
  3. taurine + L-arginine = taurocyamine + L-ornithine

  Catalysed by SLC7A6, GATMcytosol, extracellular space

• L-glutamate 5-semialdehydeReach from here →
  1. alanine racemase
  2. transport of alanine and ornithine (cytosol to extracellular)
  3. L-ornithine + 2-oxoglutarate = L-glutamate 5-semialdehyde + L-glutamate

  Catalysed by SLC7A6, OATcytosol, extracellular space

• N(4)-(beta-N-acetyl-D-glucosaminyl)-L-asparagineReach from here →
  1. alanine racemase
  2. oxaloacetate + L-alanine = L-aspartate + pyruvate
  3. N(4)-(beta-N-acetyl-D-glucosaminyl)-L-asparagine + H2O = N-acetyl-beta-D-glucosaminylamine + L-aspartate + H(+)

  Catalysed by AGXT2, AGAcytosol

• porphobilinogenReach from here →
  1. transport of D-alanine and glycine (cytosol to extracellular)
  2. succinyl-CoA:glycine C-succinyltransferase (decarboxylating)
  3. 5-aminolevulinate hydro-lyase (adding 5-aminolevulinate and cyclizing

  Catalysed by SLC3A2, SLC7A10, ALAS1, ALAS2 and 2 moreextracellular space, cytosol, mitochondrial matrixOne of 2 routes

• L,L-cystathionineReach from here →
  1. alanine racemase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. N-acetylglutamate synthase (N-acetyl-L-cystathionine)

  Catalysed by NAGScytosol, mitochondrial matrix

• gamma-L-glutamyl-L-cysteineReach from here →
  1. alanine racemase
  2. transport of alanine and cysteine (cytosol to extracellular)
  3. L-glutamate:L-cysteine gamma-ligase (ADP-forming)

  Catalysed by SLC7A5, GCLC, GCLMcytosol, extracellular spaceOne of 2 routes

• 6-amino-2-oxohexanoateReach from here →
  1. alanine racemase
  2. transport of alanine and lysine (cytosol to extracellular)
  3. L-lysine:oxygen 2-oxidoreductase (deaminating)

  Catalysed by SLC7A6cytosol, extracellular space, peroxisome

• L-homocysteineReach from here →
  1. alanine racemase
  2. transport of alanine and methionine (cytosol to extracellular)
  3. S-methyl-L-methionine + L-homocysteine = 2 L-methionine + H(+)

  Catalysed by SLC7A5, BHMT2cytosol, extracellular space

• N,N-dimethylglycineReach from here →
  1. transport of D-alanine and glycine (cytosol to extracellular)
  2. sarcosine + O2 + H2O = formaldehyde + glycine + H2O2
  3. (6S)-5,6,7,8-tetrahydrofolyl-(gamma-L-Glu)(n) + N,N-dimethylglycine + oxidized [electron-transfer flavoprotein] + H(+) = (6R)-5,10-methylenetetrahydrofolyl-(gamma-L-Glu)(n) + sarcosine + reduced [electron-transfer flavoprotein]

  Catalysed by SLC3A2, SLC7A10, PIPOX, DMGDHextracellular space, cytosol

• S-methyl-L-methionineReach from here →
  1. alanine racemase
  2. transport of alanine and methionine (cytosol to extracellular)
  3. S-methyl-L-methionine + L-homocysteine = 2 L-methionine + H(+)

  Catalysed by SLC7A5, BHMT2cytosol, extracellular space

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

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

• (2R)-2-phosphoglycerateReach from here →
  1. D-alanine:oxygen oxidoreductase (deaminating)
  2. pyruvate kinase (dTDP)
  3. 2-phospho-D-glycerate hydro-lyase (phosphoenolpyruvate-forming)

  Catalysed by DAO, PKM, PKLR, ENO1 and 2 moreperoxisome, cytosol

• glutathione disulfideReach from here →
  1. alanine racemase
  2. Transport of L-Cystine (L-Alanine antiport) by B0, +At Transporter
  3. cystine to cysteine conversion

  Catalysed by SLC7A9, SLC3A1cytosol, extracellular spaceOne of 36 routes

• taurolithocholate 3-sulfateReach 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 sulfotaurolithocholate (cytosol to extracellular)

  Catalysed by SLC3A2, SLC7A10, GSS, SLCO1A2 and 1 moreextracellular space, cytosolOne of 2 routes

• an acyl-CoAReach from here →
  1. alanine racemase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. acyl-CoA:sphingosine N-acyltransferase

  Catalysed by ASAH1, ACER2, ACER1, ASAH2cytosol, mitochondrial matrix, Golgi apparatusOne of 3 routes

• 5-oxo-L-prolineReach 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. glutathione = L-cysteinylglycine + 5-oxo-L-proline

  Catalysed by SLC3A2, SLC7A10, GSS, CHAC2 and 1 moreextracellular space, cytosol

• histamineReach from here →
  1. alanine racemase
  2. transport of alanine and histidine (cytosol to extracellular)
  3. L-histidine carboxy-lyase (histamine-forming)

  Catalysed by SLC7A6, HDCcytosol, extracellular spaceOne of 3 routes

• L-2-aminopentanoateReach from here →
  1. alanine racemase
  2. L-kynurenine + H2O = anthranilate + L-alanine + H(+)
  3. 2-oxopentanoate + L-kynurenine = L-2-aminopentanoate + kynurenate + H2O

  Catalysed by KYNU, AADATcytosolOne of 2 routes

• (2S)-2-[5-amino-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamido]succinateReach from here →
  1. alanine racemase
  2. oxaloacetate + L-alanine = L-aspartate + pyruvate
  3. 1-(5-Phosphoribosyl)-5-amino-4-carboxyimidazole:L-aspartate ligase (ADP-forming)

  Catalysed by AGXT2, PAICScytosolOne of 2 routes

• L-thyroxineReach 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 thyroxine (cytosol to extracellular)

  Catalysed by SLC3A2, SLC7A10, GSS, SLCO1A2 and 1 moreextracellular space, cytosolOne of 2 routes

• kynurenateReach from here →
  1. alanine racemase
  2. L-kynurenine + H2O = anthranilate + L-alanine + H(+)
  3. Kynurenine-Oxoglutarate Transaminase

  Catalysed by KYNU, KYAT3, AADATcytosol, mitochondrial matrixOne of 16 routes

• L-2-aminohexanoateReach from here →
  1. alanine racemase
  2. L-kynurenine + H2O = anthranilate + L-alanine + H(+)
  3. 2-oxohexanoate + L-kynurenine = L-2-aminohexanoate + kynurenate + H2O

  Catalysed by KYNU, AADATcytosolOne of 2 routes

• 5-amino-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamideReach from here →
  1. transport of D-alanine and glycine (cytosol to extracellular)
  2. 5,10-Methylenetetrahydrofolate:glycine hydroxymethyltransferase
  3. phosphoribosylaminoimidazolecarboxamide formyltransferase (10-formyl-THF)

  Catalysed by SLC3A2, SLC7A10, SHMT1, ATICextracellular space, cytosol

• 5-guanidino-2-oxopentanoateReach from here →
  1. alanine racemase
  2. transport of alanine and arginine (cytosol to extracellular)
  3. L-arginine + O2 + H2O = 5-guanidino-2-oxopentanoate + H2O2 + NH4(+)

  Catalysed by SLC7A6, IL4I1cytosol, extracellular space

• N(8)-acetylspermidineReach from here →
  1. D-alanine:oxygen oxidoreductase (deaminating)
  2. transport of acetate and pyruvate (cytosol to extracellular)
  3. N(8)-acetylspermidine + H2O = spermidine + acetate

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

• (3Z)-dodecenoyl-CoAReach from here →
  1. alanine racemase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. acetyl-CoA C-acyltransferase (3-oxomyrist-5-enoyl-CoA)

  Catalysed by HADHA, ACAA2, HADHBcytosol, mitochondrial matrixOne of 3 routes

• S-sulfanyl-L-cysteineReach from here →
  1. alanine racemase
  2. transport of alanine and cysteine (cytosol to extracellular)
  3. 2 L-cysteine = S-sulfanyl-L-cysteine + L-alanine

  Catalysed by SLC7A5, CARS2cytosol, extracellular space

• N-formyl-L-kynurenineReach from here →
  1. alanine racemase
  2. transport of alanine and tryptophan (cytosol to extracellular)
  3. L-tryptophan + O2 = N-formyl-L-kynurenine

  Catalysed by SLC7A5, IDO1, TDO2, IDO2cytosol, extracellular spaceOne of 2 routes

• (S)-3-amino-2-methylpropanoateReach from here →
  1. D-alanine:oxygen oxidoreductase (deaminating)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. L-3-amino-isobutanoate:2-oxoglutarate aminotransferase

  Catalysed by DAO, AGXT2, ABATperoxisome, mitochondrial matrix

• L-2-aminoadipateReach from here →
  1. alanine racemase
  2. L-kynurenine + H2O = anthranilate + L-alanine + H(+)
  3. 2-oxoadipate + L-kynurenine = L-2-aminoadipate + kynurenate + H2O

  Catalysed by KYNU, AADATcytosol

• (25R)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oyl-CoAReach from here →
  1. alanine racemase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. 3alpha,7alpha,12alpha-trihydroxy-5beta-cholestanoate:CoA ligase (AMP-forming)

  Catalysed by SLC27A2, SLC27A5cytosol, mitochondrial matrix, endoplasmic reticulumOne of 3 routes

• phosphoenolpyruvateReach from here →
  1. D-alanine:oxygen oxidoreductase (deaminating)
  2. Pyruvate:carbon-dioxide ligase (ADP-forming)
  3. oxaloacetate + GTP = phosphoenolpyruvate + GDP + CO2

  Catalysed by DAO, PC, PCK1, PCK2peroxisome, mitochondrial matrix

• an N-acetyl-L-cysteine-S-conjugateReach from here →
  1. D-alanine:oxygen oxidoreductase (deaminating)
  2. transport of acetate and pyruvate (cytosol to extracellular)
  3. an N-acetyl-L-cysteine-S-conjugate + H2O = an S-substituted L-cysteine + acetate

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