5-(3-methylguanidino)-2-oxopentanoate

Three steps

• dodecanamideReach from here →
  1. N(omega)-methyl-L-arginine + glyoxylate = 5-(3-methylguanidino)-2-oxopentanoate + glycine
  2. N-dodecanoyl-(2S)-hydroxyglycine = dodecanamide + glyoxylate
  3. N-dodecanoyl-(2S)-hydroxyglycine = dodecanamide + glyoxylate

  Catalysed by AGXT2, PAM

• 2-oxohexanoateReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. N(omega),N(omega)-dimethyl-L-arginine + pyruvate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + L-alanine
  3. 2-oxohexanoate + N(omega),N(omega)-dimethyl-L-arginine = L-2-aminohexanoate + 5-(3,3-dimethylguanidino)-2-oxopentanoate

  Catalysed by AGXT2

• D-cysteineReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  3. D-cysteine(out) + L-alanine(in) = D-cysteine(in) + L-alanine(out)

  Catalysed by AGXT2, SLC7A10inner side of the membrane, outer side of the membraneOne of 2 routes

• L-alpha-aminobutyric acidReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. 2-oxobutanoate + L-alanine = (2S)-2-aminobutanoate + pyruvate
  3. glutamic-pyruvic transaminase ((S)-2-aminobutanoate)

  Catalysed by AGXT2, GPTcytosol

• 5-aminolevulinateReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. N(omega)-methyl-L-arginine + glyoxylate = 5-(3-methylguanidino)-2-oxopentanoate + glycine
  3. succinyl-CoA + glycine + H(+) = 5-aminolevulinate + CO2 + CoA

  Catalysed by AGXT2, ALAS1, ALAS2

• glycochenodeoxycholateReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. N(omega)-methyl-L-arginine + glyoxylate = 5-(3-methylguanidino)-2-oxopentanoate + glycine
  3. chenodeoxycholoyl-CoA + glycine = glycochenodeoxycholate + CoA + H(+)

  Catalysed by AGXT2, BAAT

• glycochenodeoxycholic acidReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. N(omega)-methyl-L-arginine + glyoxylate = 5-(3-methylguanidino)-2-oxopentanoate + glycine
  3. bile acid-CoA: amino acid N-acyltransferase

  Catalysed by AGXT2, BAATperoxisomeOne of 3 routes

• 3-hydroxyisovaleric acidReach from here →
  1. N(omega)-methyl-L-arginine + glyoxylate = 5-(3-methylguanidino)-2-oxopentanoate + glycine
  2. L-leucine + glyoxylate = 4-methyl-2-oxopentanoate + glycine
  3. 4-methyl-2-oxopentanoate decarboxylation

  Catalysed by AGXT2, AADAT, ALOX12B, ALOXE3cytosol

• glycolithocholic acidReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. N(omega)-methyl-L-arginine + glyoxylate = 5-(3-methylguanidino)-2-oxopentanoate + glycine
  3. bile acid-CoA:amino acid N-acyltransferase (glycine)

  Catalysed by AGXT2, BAATcytosolOne of 2 routes

• decanamideReach from here →
  1. N(omega)-methyl-L-arginine + glyoxylate = 5-(3-methylguanidino)-2-oxopentanoate + glycine
  2. N-decanoyl-(2S)-hydroxyglycine = decanamide + glyoxylate
  3. N-decanoyl-(2S)-hydroxyglycine = decanamide + glyoxylate

  Catalysed by AGXT2, PAM

• L-2-amino-3-oxobutanoic acidReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. N(omega)-methyl-L-arginine + glyoxylate = 5-(3-methylguanidino)-2-oxopentanoate + glycine
  3. Acetyl-CoA:glycine C-acetyltransferase

  Catalysed by AGXT2, GCATmitochondrial matrix

• (3S)-3-hydroxy-3-methylglutaryl-CoAReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. transport of acetoacetate and pyruvate (cytosol to mitochondria)
  3. (3S)-3-hydroxy-3-methylglutaryl-CoA = acetoacetate + acetyl-CoA

  Catalysed by AGXT2, HMGCL, HMGCLL1mitochondrial matrix, cytosol

• 13-cis-retinalReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. transport of pyruvate and retinoate (cytosol to extracellular)
  3. retinal dehydrogenase (13-cis-retinal)

  Catalysed by AGXT2, SLC16A4, SLC16A5, SLC16A3 and 5 moreextracellular space, cytosol, endoplasmic reticulum

• L-ornithineReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  3. Amino Acid-Polyamine-Organocation (Apc) Tcdb:2.A.3.8.15

  Catalysed by AGXT2, DDAH1, SLC7A9extracellular space, cytosolOne of 37 routes

• N-(acetyl)-sphing-4-enineReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. transport of acetate and pyruvate (cytosol to extracellular)
  3. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate

  Catalysed by AGXT2, SLC16A4, SLC16A5, SLC16A3 and 3 moreextracellular space, cytosol

• 1,2-dihydroxy-5-(methylsulfanyl)pent-1-en-3-oneReach from here →
  1. N(omega)-methyl-L-arginine + glyoxylate = 5-(3-methylguanidino)-2-oxopentanoate + glycine
  2. glyoxylate + L-methionine = 4-methylsulfanyl-2-oxobutanoate + glycine
  3. 1,2-dihydroxy-5-(methylsulfanyl)pent-1-en-3-one + O2 = 4-methylsulfanyl-2-oxobutanoate + formate + 2 H(+)

  Catalysed by AGXT2, AADAT, ADI1

• gamma-Glu-AlaReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  3. gamma-glutamyltransferase (alanine)

  Catalysed by AGXT2, GGT1, GGT5, GGTLC2 and 3 moreextracellular space, cytosol

• S(8)-aminomethyldihydrolipoamideReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. N(omega)-methyl-L-arginine + glyoxylate = 5-(3-methylguanidino)-2-oxopentanoate + glycine
  3. dihydrolipoyl dehydrogenase ([protein]-N6-(lipoyl)lysine)

  Catalysed by AGXT2, GLDC, GCSHmitochondrial matrix

• acetoacetyl-CoAReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. transport of acetoacetate and pyruvate (cytosol to mitochondria)
  3. acetoacetate + ATP + CoA = acetoacetyl-CoA + AMP + diphosphate

  Catalysed by AGXT2, AACSmitochondrial matrix, cytosolOne of 2 routes

• (S)-malyl-CoAReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. (S)-malate + NAD(+) = pyruvate + CO2 + NADH
  3. (S)-malate + ATP + CoA = (S)-malyl-CoA + ADP + phosphate

  Catalysed by AGXT2, ME2, SUCLG1, SUCLA2

• (R)-methylmalonyl-CoAReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. aldehyde dehydrogenase (2-methyl-3-oxopropanoate)

  Catalysed by AGXT2, ALDH6A1mitochondrial matrix

• butanoyl-CoAReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. transport of butyrate and pyruvate (cytosol to extracellular)
  3. Butanoate:CoA ligase (AMP-forming)

  Catalysed by AGXT2, SLC16A4, SLC16A5, SLC16A3 and 9 moreextracellular space, cytosolOne of 2 routes

• propanoyl-CoAReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. (R)-3-amino-2-methylpropanoate + pyruvate = 2-methyl-3-oxopropanoate + L-alanine
  3. 2-methyl-3-oxopropanoate + NAD(+) + CoA + H2O = propanoyl-CoA + hydrogencarbonate + NADH + H(+)

  Catalysed by AGXT2, ALDH6A1One of 2 routes

• prostaglandin E1Reach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. (S)-lactate + NAD(+) = pyruvate + NADH + H(+)
  3. prostaglandin E1(out) + 2 (S)-lactate(in) = prostaglandin E1(in) + 2 (S)-lactate(out)

  Catalysed by AGXT2, LDHA, LDHB, LDHC and 3 moreinner side of the membrane, outer side of the membraneOne of 2 routes

• prostaglandin F2alphaReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. (S)-lactate + NAD(+) = pyruvate + NADH + H(+)
  3. prostaglandin F2alpha(out) + 2 (S)-lactate(in) = prostaglandin F2alpha(in) + 2 (S)-lactate(out)

  Catalysed by AGXT2, LDHA, LDHB, LDHC and 3 moreinner side of the membrane, outer side of the membraneOne of 2 routes

• prostaglandin H2Reach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. (S)-lactate + NAD(+) = pyruvate + NADH + H(+)
  3. prostaglandin H2(out) + 2 (S)-lactate(in) = prostaglandin H2(in) + 2 (S)-lactate(out)

  Catalysed by AGXT2, LDHA, LDHB, LDHC and 3 moreinner side of the membrane, outer side of the membraneOne of 2 routes

• prostaglandin D2Reach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. (S)-lactate + NAD(+) = pyruvate + NADH + H(+)
  3. prostaglandin D2(out) + 2 (S)-lactate(in) = prostaglandin D2(in) + 2 (S)-lactate(out)

  Catalysed by AGXT2, LDHA, LDHB, LDHC and 3 moreinner side of the membrane, outer side of the membraneOne of 2 routes

• D-alanineReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  3. D-alanine(out) + L-alanine(in) = D-alanine(in) + L-alanine(out)

  Catalysed by AGXT2, SLC7A10inner side of the membrane, outer side of the membraneOne of 2 routes

• sarcosineReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. N(omega)-methyl-L-arginine + glyoxylate = 5-(3-methylguanidino)-2-oxopentanoate + glycine
  3. sarcosine + O2 + H2O = formaldehyde + glycine + H2O2

  Catalysed by AGXT2, PIPOXOne of 2 routes

• (6S)-5,6,7,8-tetrahydrofolateReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. N(omega)-methyl-L-arginine + glyoxylate = 5-(3-methylguanidino)-2-oxopentanoate + glycine
  3. (6R)-5,10-methylene-5,6,7,8-tetrahydrofolate + glycine + H2O = (6S)-5,6,7,8-tetrahydrofolate + L-serine

  Catalysed by AGXT2, SHMT1, SHMT2

• 2-(N(omega)-L-arginino)succinateReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  3. L-Citrulline:L-aspartate ligase (AMP-forming)

  Catalysed by AGXT2, DDAH1, ASS1cytosolOne of 4 routes

• 4-guanidinobutanoateReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. N(omega)-methyl-L-arginine(in) + L-arginine(out) = N(omega)-methyl-L-arginine(out) + L-arginine(in)
  3. 4-aminobutanoate + L-arginine = 4-guanidinobutanoate + L-ornithine

  Catalysed by AGXT2, SLC25A29, GATMinner side of the membrane, outer side of the membrane

• N-acetyl-D-glucosamine 6-phosphateReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. transport of acetate and pyruvate (cytosol to extracellular)
  3. N-acetyl-D-glucosamine 6-phosphate + H2O = D-glucosamine 6-phosphate + acetate

  Catalysed by AGXT2, SLC16A4, SLC16A5, SLC16A3 and 3 moreextracellular space, cytosol

• 3-guanidinopropanoateReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. N(omega)-methyl-L-arginine(in) + L-arginine(out) = N(omega)-methyl-L-arginine(out) + L-arginine(in)
  3. beta-alanine + L-arginine = 3-guanidinopropanoate + L-ornithine

  Catalysed by AGXT2, SLC25A29, GATMinner side of the membrane, outer side of the membrane

• L-histidineReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. N(omega)-methyl-L-arginine(in) + L-arginine(out) = N(omega)-methyl-L-arginine(out) + L-arginine(in)
  3. L-histidine(out) + L-arginine(in) + Na(+)(out) = L-histidine(in) + L-arginine(out) + Na(+)(in)

  Catalysed by AGXT2, SLC25A29, SLC7A6inner side of the membrane, outer side of the membraneOne of 3 routes

• an N-acylglycineReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. N(omega)-methyl-L-arginine + glyoxylate = 5-(3-methylguanidino)-2-oxopentanoate + glycine
  3. an acyl-CoA + glycine = an N-acylglycine + CoA + H(+)

  Catalysed by AGXT2, GLYATL3, GLYAT, GLYATL2

• guanidinoacetateReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. N(omega)-methyl-L-arginine(in) + L-arginine(out) = N(omega)-methyl-L-arginine(out) + L-arginine(in)
  3. L-Arginine:glycine amidinotransferase

  Catalysed by AGXT2, SLC25A29, GATMinner side of the membrane, outer side of the membrane, cytosolOne of 4 routes

• D-threonineReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  3. D-threonine(out) + L-alanine(in) = D-threonine(in) + L-alanine(out)

  Catalysed by AGXT2, SLC7A10inner side of the membrane, outer side of the membraneOne of 2 routes

• CMP-N-acetyl-beta-neuraminateReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)
  3. CTP:N-acetylneuraminate cytidylyltransferase

  Catalysed by AGXT2, NPL, CMAScytosol, nucleusOne of 2 routes

• L-tryptophanReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  3. transport of citrulline and tryptophan (cytosol to extracellular)

  Catalysed by AGXT2, DDAH1, SLC7A9, SLC3A1 and 1 moreextracellular space, cytosolOne of 18 routes

• glutathioneReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. N(omega)-methyl-L-arginine + glyoxylate = 5-(3-methylguanidino)-2-oxopentanoate + glycine
  3. gamma-L-glutamyl-L-cysteine + glycine + ATP = glutathione + ADP + phosphate + H(+)

  Catalysed by AGXT2, GSS

• L-threonineReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  3. L-threonine(out) + L-alanine(in) = L-threonine(in) + L-alanine(out)

  Catalysed by AGXT2, SLC7A10inner side of the membrane, outer side of the membraneOne of 5 routes

• L-kynurenineReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  3. L-kynurenine + H2O = anthranilate + L-alanine + H(+)

  Catalysed by AGXT2, KYNU

• beta-alanineReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  3. beta-alanine(out) + L-alanine(in) = beta-alanine(in) + L-alanine(out)

  Catalysed by AGXT2, SLC7A10inner side of the membrane, outer side of the membraneOne of 2 routes

• leukotriene C4Reach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. N(omega)-methyl-L-arginine + glyoxylate = 5-(3-methylguanidino)-2-oxopentanoate + glycine
  3. leukotriene C4 hydrolysis

  Catalysed by AGXT2cytosol

• 2-hydroxy-3-oxopropanoateReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. L-Serine:pyruvate aminotransferase
  3. hydroxypyruvate aldose-ketose-isomerase

  Catalysed by AGXT2, AGXT, HYIcytosolOne of 2 routes

• L-asparagineReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  3. transport of asparagine and citrulline (cytosol to extracellular)

  Catalysed by AGXT2, DDAH1, SLC7A9, SLC3A1 and 1 moreextracellular space, cytosolOne of 16 routes

• taurocyamineReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. N(omega)-methyl-L-arginine(in) + L-arginine(out) = N(omega)-methyl-L-arginine(out) + L-arginine(in)
  3. taurine + L-arginine = taurocyamine + L-ornithine

  Catalysed by AGXT2, SLC25A29, GATMinner side of the membrane, outer side of the membrane

• L-phenylalanineReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  3. transport of citrulline and phenylalanine (cytosol to extracellular)

  Catalysed by AGXT2, DDAH1, SLC7A6extracellular space, cytosolOne of 30 routes

• 3-hydroxy-L-kynurenineReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  3. 3-hydroxy-L-kynurenine + H2O = 3-hydroxyanthranilate + L-alanine + H(+)

  Catalysed by AGXT2, KYNU