5-(3-methylguanidino)-2-oxopentanoate

Three steps

• propionyl-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. 2-Methyl-3-oxopropanoate:NAD+ oxidoreductase (CoA-propanoylating)

  Catalysed by AGXT2, ALDH6A1mitochondrial matrixOne of 5 routes

• CHEBI:15570Reach 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. alanine racemase

  Catalysed by AGXT2cytosolOne of 3 routes

• L-leucineReach 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 leucine (cytosol to extracellular)

  Catalysed by AGXT2, DDAH1extracellular space, cytosolOne of 25 routes

• CHEBI:15611Reach 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. S-Adenosyl-L-methionine:glycine N-methyltransferase

  Catalysed by AGXT2, GNMTcytosol

• 10-formyltetrahydrofolic acidReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. transport of formate and pyruvate (cytosol to extracellular)
  3. Formate:tetrahydrofolate ligase (ADP-forming)

  Catalysed by AGXT2, SLC16A4, SLC16A5, SLC16A7 and 3 moreextracellular space, cytosolOne of 2 routes

• CHEBI:15699Reach 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 homoserine (cytosol to extracellular)

  Catalysed by AGXT2, DDAH1, SLC7A9, SLC3A1 and 1 moreextracellular space, cytosolOne of 13 routes

• formateReach from here →
  1. N(omega)-methyl-L-arginine + glyoxylate = 5-(3-methylguanidino)-2-oxopentanoate + glycine
  2. glyoxylate + O2 + H2O = oxalate + H2O2 + H(+)
  3. oxalate(in) + formate(out) = oxalate(out) + formate(in)

  Catalysed by AGXT2, HAO1, SLC26A6inner side of the membrane, outer side of the membraneOne of 2 routes

• malonateReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. (S)-malate + NAD(+) = pyruvate + CO2 + NADH
  3. malonate(out) + (S)-malate(in) = malonate(in) + (S)-malate(out)

  Catalysed by AGXT2, ME2, SLC25A10inner side of the membrane, outer side of the membraneOne of 2 routes

• CHEBI:15971Reach 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 histidine (cytosol to extracellular)

  Catalysed by AGXT2, DDAH1, SLC7A5, SLC7A6extracellular space, cytosolOne of 16 routes

• homogentisateReach from here →
  1. N(omega)-methyl-L-arginine + glyoxylate = 5-(3-methylguanidino)-2-oxopentanoate + glycine
  2. L-tyrosine + glyoxylate = 3-(4-hydroxyphenyl)pyruvate + glycine
  3. 4-Hydroxyphenylpyruvate:oxygen oxidoreductase (hydroxylating,decarboxylating)

  Catalysed by AGXT2, AADAT, HPDcytosolOne of 2 routes

• CHEBI:16174Reach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. pyruvate kinase (dTDP)
  3. nucleoside-diphosphate kinase (dADP)

  Catalysed by AGXT2, PKM, PKLR, NME4 and 5 morecytosolOne of 3 routes

• sulfateReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. (S)-malate + NAD(+) = pyruvate + CO2 + NADH
  3. transport of malate and sulfate (cytosol to mitochondria)

  Catalysed by AGXT2, ME2, SLC25A10mitochondrial matrix, cytosolOne of 6 routes

• ureaReach 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 amidinohydrolase

  Catalysed by AGXT2, SLC25A29, ARG1inner side of the membrane, outer side of the membrane, cytosolOne of 3 routes

• L-cystineReach 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-cystine(out) + L-arginine(in) = L-cystine(in) + L-arginine(out)

  Catalysed by AGXT2, SLC25A29, SLC7A9inner side of the membrane, outer side of the membraneOne of 2 routes

• CHEBI:16284Reach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. pyruvate kinase (dTDP)
  3. deoxythymidylate kinase (dADP)

  Catalysed by AGXT2, PKM, PKLR, DTYMKcytosol, mitochondrial matrixOne of 3 routes

• (R)-3-aminoisobutyric acidReach 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. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase

  Catalysed by AGXT2mitochondrial matrixOne of 3 routes

• L-valineReach 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 valine (cytosol to extracellular)

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

• nitric oxideReach 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, NADPH:Oxygen Oxidoreductase (Nitric-Oxide-Forming)

  Catalysed by AGXT2, SLC25A29, NOS3, NOS1 and 1 moreinner side of the membrane, outer side of the membrane, cytosolOne of 2 routes

• CHEBI:16497Reach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. pyruvate kinase (dTDP)
  3. dGTP:pyruvate 2-O-phosphotransferase

  Catalysed by AGXT2, PKM, PKLRcytosol

• CHEBI:16523Reach 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. transport of D-serine and glycine (cytosol to extracellular)

  Catalysed by AGXT2, SLC3A2, SLC7A10extracellular space, cytosolOne of 2 routes

• protein polypeptide chainReach 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. PROTEIN_BS

  Catalysed by AGXT2, SLC25A29inner side of the membrane, outer side of the membrane, cytosolOne of 4 routes

• N(2)-acetyl-L-ornithineReach 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. N2-Acetyl-L-ornithine amidohydrolase

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

• CHEBI:16633Reach 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-selenocysteine selenide-lyase (L-alanine-forming)

  Catalysed by AGXT2, SCLYcytosol

• Met-tRNA(Met)Reach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. N(1)-methylguanosine(37) in tRNA(Phe) + pyruvate + S-adenosyl-L-methionine = 4-demethylwyosine(37) in tRNA(Phe) + 5'-deoxyadenosine + L-methionine + CO2 + H2O
  3. L-Methionine:tRNAMet ligase (AMP-forming)

  Catalysed by AGXT2, TYW1B, TYW1, MARS1cytosol

• (R)-glycerateReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. L-Serine:pyruvate aminotransferase
  3. D-glycerate:NADP+ 2-oxidoreductase

  Catalysed by AGXT2, AGXT, GRHPRcytosolOne of 4 routes

• N-[(S)-lactoyl]-L-phenylalanineReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. (S)-lactate + NAD(+) = pyruvate + NADH + H(+)
  3. (S)-lactate + L-phenylalanine = N-[(S)-lactoyl]-L-phenylalanine + H2O

  Catalysed by AGXT2, LDHA, LDHB, LDHC and 3 more

• enol-phenylpyruvateReach from here →
  1. N(omega)-methyl-L-arginine + glyoxylate = 5-(3-methylguanidino)-2-oxopentanoate + glycine
  2. glyoxylate + L-phenylalanine = 3-phenylpyruvate + glycine
  3. 3-phenylpyruvate = enol-phenylpyruvate

  Catalysed by AGXT2, AADAT, MIF

• formaldehydeReach 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. methylamine:oxygen oxidoreductase (deaminating) (copper-containing)

  Catalysed by AGXT2, DDAH1, AOC2, AOC1 and 1 morecytosolOne of 2 routes

• CHEBI:16856Reach 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 ligase (ADP-forming)

  Catalysed by AGXT2, GSScytosol

• CHEBI:16857Reach 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 threonine (cytosol to extracellular)

  Catalysed by AGXT2, DDAH1, SLC7A6extracellular space, cytosolOne of 15 routes

• glyoxylic 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. glycine:oxygen oxidoreductase (deaminating)

  Catalysed by AGXT2, DAOperoxisomeOne of 4 routes

• ferrocytochrome cReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. (S)-Lactate:NAD+ oxidoreductase
  3. (S)-Lactate:ferricytochrome-c 2-oxidoreductase

  Catalysed by AGXT2, LDHB, LDHAL6B, CYB5D1mitochondrial matrix, cytosolOne of 2 routes

• glycolaldehydeReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. L-Serine:pyruvate aminotransferase
  3. hydroxypyruvate carboxy-lyase (glycolaldehyde-forming)

  Catalysed by AGXT2, AGXTcytosolOne of 2 routes

• aldehydo-N-acetyl-D-mannosamineReach 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. N-Acetylneuraminate pyruvate-lyase (N-acetyl-D-mannosamine-forming)

  Catalysed by AGXT2, NPLcytosolOne of 2 routes

• L-isoleucineReach 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 isoleucine (cytosol to extracellular)

  Catalysed by AGXT2, DDAH1, SLC7A6extracellular space, cytosolOne of 14 routes

• CHEBI:17203Reach 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 proline (cytosol to extracellular)

  Catalysed by AGXT2, DDAH1, SLC7A6extracellular space, cytosolOne of 12 routes

• (S)-4-hydroxymandelateReach from here →
  1. N(omega)-methyl-L-arginine + glyoxylate = 5-(3-methylguanidino)-2-oxopentanoate + glycine
  2. L-tyrosine + glyoxylate = 3-(4-hydroxyphenyl)pyruvate + glycine
  3. 3-(4-hydroxyphenyl)pyruvate + O2 = (S)-4-hydroxymandelate + CO2

  Catalysed by AGXT2, AADAT, HPDL

• 17alpha-hydroxyprogesteroneReach 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. cytochrome P450 (17alpha-hydroxyprogesterone)

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

• sulfiteReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. (S)-malate + NAD(+) = pyruvate + CO2 + NADH
  3. transport of malate and sulfite (cytosol to mitochondria)

  Catalysed by AGXT2, ME2, SLC25A10mitochondrial matrix, cytosolOne of 2 routes

• CHEBI:17380Reach from here →
  1. N(omega)-methyl-L-arginine + glyoxylate = 5-(3-methylguanidino)-2-oxopentanoate + glycine
  2. 3-hydroxy-L-kynurenine + glyoxylate = xanthurenate + glycine + H2O
  3. Kynurenine-Oxoglutarate Transaminase

  Catalysed by AGXT2, KYAT3, AADATmitochondrial matrixOne of 2 routes

• agmatineReach 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 carboxy-lyase (agmatine-forming)

  Catalysed by AGXT2, SLC25A29inner side of the membrane, outer side of the membrane, mitochondrial matrix

• enol-oxaloacetateReach 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 + a quinone = enol-oxaloacetate + a quinol

  Catalysed by AGXT2, ME2, SDHB, SDHA

• AH2Reach 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. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O

  Catalysed by AGXT2, MOCOSOne of 7 routes

• 5-aminolevulinic 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. succinyl-CoA:glycine C-succinyltransferase (decarboxylating)

  Catalysed by AGXT2, ALAS1, ALAS2, CPNE7mitochondrial matrix

• L-cysteineReach 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 cysteine (cytosol to extracellular)

  Catalysed by AGXT2, DDAH1, SLC7A6extracellular space, cytosolOne of 32 routes

• Ala-tRNA(Ala)Reach 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-Alanine:tRNA(Ala) ligase (AMP-forming)

  Catalysed by AGXT2, AARS1cytosol

• 4-methylumbelliferyl acetateReach 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. 4-methylumbelliferyl acetate + H2O = 4-methylumbelliferone + acetate + H(+)

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

• urateReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. (S)-Lactate:NAD+ oxidoreductase
  3. transport of L-lactate and urate (cytosol to extracellular)

  Catalysed by AGXT2, LDHB, LDHAL6B, SLC22A12mitochondrial matrix, extracellular space, cytosolOne of 2 routes

• CHEBI:17895Reach 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 tyrosine (cytosol to extracellular)

  Catalysed by AGXT2, DDAH1, SLC7A6extracellular space, cytosolOne of 16 routes

• all-trans-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. retinoate reduction

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