N(omega)-methyl-L-arginine

Three steps

• S-methyl-5'-thioadenosineReach from here →
  1. N(omega)-methyl-L-arginine(in) + L-arginine(out) = N(omega)-methyl-L-arginine(out) + L-arginine(in)
  2. Putrescine Export via Putrescine/Arginine Antiporter
  3. S-adenosylmethioninamine:putrescine 3-aminopropyltransferase

  Catalysed by SLC25A29, SLC3A2, SLC7A7, SRMinner side of the membrane, outer side of the membrane, extracellular space, cytosolOne of 2 routes

• nitrateReach from here →
  1. N(omega)-methyl-L-arginine(in) + L-arginine(out) = N(omega)-methyl-L-arginine(out) + L-arginine(in)
  2. L-Arginine, NADPH:Oxygen Oxidoreductase (Nitric-Oxide-Forming)
  3. Fe(II)-heme b-[protein] + nitric oxide + O2 = Fe(III)-heme b-[protein] + nitrate

  Catalysed by SLC25A29, NOS3, NOS1, NOS2 and 1 moreinner side of the membrane, outer side of the membrane, cytosol

• indole-3-pyruvateReach from here →
  1. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  2. transport of citrulline and tryptophan (cytosol to extracellular)
  3. L-tryptophan + O2 + H2O = indole-3-pyruvate + H2O2 + NH4(+)

  Catalysed by DDAH1, SLC7A9, SLC3A1, SLC7A6 and 1 moreextracellular space, cytosolOne of 3 routes

• 3,3',5'-triiodo-L-thyronine sulfateReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. 3,3',5'-triiodo-L-thyronine sulfate + iodide + A + H(+) = L-thyroxine sulfate + AH2

  Catalysed by AGXT2, MOCOS, DIO1

• 3,3'-diiodo-L-thyronineReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. 3,3'-diiodo-L-thyronine + iodide + A + H(+) = 3,3',5-triiodo-L-thyronine + AH2

  Catalysed by AGXT2, MOCOS, DIO1, DIO3One of 2 routes

• 3,3'-diiodo-L-thyronine sulfateReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. 3,3'-diiodo-L-thyronine sulfate + iodide + A + H(+) = 3,3',5-triiodo-L-thyronine sulfate + AH2

  Catalysed by AGXT2, MOCOS, DIO1One of 2 routes

• (7Z,10Z,13Z)-hexadecatrienoyl-CoAReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. Fatty Acid Beta Oxidation (C18:3->C16:3), Mitochondrial

  Catalysed by AGXT2, HADHA, ACADVL, HADHBmitochondrial matrix

• CHEBI:17724Reach from here →
  1. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  2. methylamine:oxygen oxidoreductase (deaminating) (copper-containing)
  3. dimethylglycine dehydrogenase (formaldehyde)

  Catalysed by DDAH1, AOC2, AOC1, AOC3 and 2 morecytosolOne of 2 routes

• glycine betaineReach from here →
  1. N(omega)-methyl-L-arginine(in) + L-arginine(out) = N(omega)-methyl-L-arginine(out) + L-arginine(in)
  2. transport of arginine and chloride (cytosol to extracellular)
  3. transport of betaine and chloride (cytosol to extracellular)

  Catalysed by SLC25A29, SLC6A14, SLC6A12inner side of the membrane, outer side of the membrane, extracellular space, cytosolOne of 3 routes

• CHEBI:17769Reach from here →
  1. N(omega)-methyl-L-arginine(in) + L-arginine(out) = N(omega)-methyl-L-arginine(out) + L-arginine(in)
  2. Putrescine Export via Putrescine/Arginine Antiporter
  3. Putrescine:oxygen oxidoreductase (deaminating)

  Catalysed by SLC25A29, SLC3A2, SLC7A7, AOC2 and 2 moreinner side of the membrane, outer side of the membrane, extracellular space, cytosolOne of 2 routes

• trans-urocanateReach from here →
  1. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  2. transport of citrulline and histidine (cytosol to extracellular)
  3. L-histidine ammonia-lyase (urocanate-forming)

  Catalysed by DDAH1, SLC7A5, SLC7A6, HALextracellular space, cytosolOne of 2 routes

• urateReach from here →
  1. N(omega)-methyl-L-arginine(in) + L-arginine(out) = N(omega)-methyl-L-arginine(out) + L-arginine(in)
  2. L-Arginine amidinohydrolase
  3. Peroxidase

  Catalysed by SLC25A29, ARG1, MPOinner side of the membrane, outer side of the membrane, cytosol, nucleusOne of 4 routes

• 5-hydroxy-L-tryptophanReach from here →
  1. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  2. transport of citrulline and tryptophan (cytosol to extracellular)
  3. (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + L-tryptophan + O2 = 5-hydroxy-L-tryptophan + (4aS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterin

  Catalysed by DDAH1, SLC7A9, SLC3A1, SLC7A6 and 2 moreextracellular space, cytosol

• methylarsonous acidReach from here →
  1. N(omega)-methyl-L-arginine + glyoxylate = 5-(3-methylguanidino)-2-oxopentanoate + glycine
  2. gamma-L-glutamyl-L-cysteine + glycine + ATP = glutathione + ADP + phosphate + H(+)
  3. methylarsonate + 2 glutathione + H(+) = methylarsonous acid + glutathione disulfide + H2O

  Catalysed by AGXT2, GSS, GSTO1, GSTO2

• 4-methyl-2-oxopentanoateReach from here →
  1. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  2. transport of citrulline and leucine (cytosol to extracellular)
  3. L-Leucine:2-oxoglutarate aminotransferase

  Catalysed by DDAH1, BCAT2extracellular space, cytosol, mitochondrial matrixOne of 5 routes

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

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

• 3-phenylpyruvateReach from here →
  1. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  2. transport of citrulline and phenylalanine (cytosol to extracellular)
  3. Phenylalanine Transaminase, Mitochondrial

  Catalysed by DDAH1, SLC7A6, GOT2, TATextracellular space, cytosol, mitochondrial matrixOne of 6 routes

• fumaric acidReach from here →
  1. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  2. L-Citrulline:L-aspartate ligase (AMP-forming)
  3. 2-(Nomega-L-arginino)succinate arginine-lyase (fumarate-forming)

  Catalysed by DDAH1, ASS1, ASLcytosolOne of 2 routes

• dTDPReach 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. pyruvate kinase (dTDP)

  Catalysed by AGXT2, PKM, PKLRcytosol

• (R)-3,4-dihydroxymandelaldehydeReach from here →
  1. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  2. (R)-adrenaline + O2 + H2O = (R)-3,4-dihydroxymandelaldehyde + methylamine + H2O2
  3. (R)-adrenaline + O2 + H2O = (R)-3,4-dihydroxymandelaldehyde + methylamine + H2O2

  Catalysed by DDAH1, MAOA, MAOB

• CHEBI:18183Reach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. gamma-glutamyltransferase (alanine)
  3. gamma-glutamylcyclotransferase ((5-L-glutamyl)-L-amino acid)

  Catalysed by AGXT2, GGT1, GGT5, GGTLC2 and 5 moreextracellular space, cytosol

• N-carbamoyl-beta-alanineReach from here →
  1. N(omega)-methyl-L-arginine(in) + L-arginine(out) = N(omega)-methyl-L-arginine(out) + L-arginine(in)
  2. transport of arginine and chloride (cytosol to extracellular)
  3. Transport of 3-Ureidopropionate

  Catalysed by SLC25A29, SLC6A14inner side of the membrane, outer side of the membrane, extracellular space, cytosolOne of 2 routes

• N(2)-formyl-N(1)-(5-phospho-D-ribosyl)glycinamideReach from here →
  1. N(omega)-methyl-L-arginine + glyoxylate = 5-(3-methylguanidino)-2-oxopentanoate + glycine
  2. 5-Phospho-D-ribosylamine:glycine ligase (ADP-forming)
  3. 10-formyltetrahydrofolate:5'-phosphoribosylglycinamide formyltransferase

  Catalysed by AGXT2, GARTcytosol

• arsenic triglutathioneReach from here →
  1. N(omega)-methyl-L-arginine + glyoxylate = 5-(3-methylguanidino)-2-oxopentanoate + glycine
  2. gamma-L-glutamyl-L-cysteine + glycine + ATP = glutathione + ADP + phosphate + H(+)
  3. arsenic triglutathione + 3 [thioredoxin]-dithiol + 3 S-adenosyl-L-methionine = trimethylarsine + 3 [thioredoxin]-disulfide + 3 glutathione + 3 S-adenosyl-L-homocysteine + 3 H(+)

  Catalysed by AGXT2, GSS, AS3MTOne of 3 routes

• 2-phenylethylamineReach from here →
  1. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  2. transport of citrulline and phenylalanine (cytosol to extracellular)
  3. L-phenylalanine carboxy-lyase (phenylethylamine-forming)

  Catalysed by DDAH1, SLC7A6, DDCextracellular space, cytosol

• CHEBI:18405Reach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. L-selenocysteine selenide-lyase (L-alanine-forming)
  3. pyridoxine 5'-phosphate:oxygen oxidoreductase

  Catalysed by AGXT2, SCLY, PNPOcytosolOne of 3 routes

• 2-formamido-N(1)-(5-phospho-D-ribosyl)acetamidineReach from here →
  1. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  2. transport of citrulline and glutamine (cytosol to extracellular)
  3. 5'-Phosphoribosylformylglycinamide:L-glutamine amido-ligase (ADP-forming)

  Catalysed by DDAH1, SLC7A6, PFASextracellular space, cytosol

• gamma-L-glutamyl-(2S)-2-aminobutanoateReach 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. (2S)-2-aminobutanoate + L-glutamate + ATP = gamma-L-glutamyl-(2S)-2-aminobutanoate + ADP + phosphate + H(+)

  Catalysed by AGXT2, GCLC

• S-methylmercury-L-cysteineReach from here →
  1. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  2. transport of citrulline and methionine (cytosol to extracellular)
  3. S-methylmercury-L-cysteine(out) + L-methionine(in) = S-methylmercury-L-cysteine(in) + L-methionine(out)

  Catalysed by DDAH1, SLC7A6, SLC7A8extracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 6 routes

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

  Catalysed by AGXT2, SLC7A10inner side of the membrane, outer side of the membrane

• 15-deoxy-Delta(12,14)-prostaglandin J2-S-(R)-glutathioneReach from here →
  1. N(omega)-methyl-L-arginine + glyoxylate = 5-(3-methylguanidino)-2-oxopentanoate + glycine
  2. gamma-L-glutamyl-L-cysteine + glycine + ATP = glutathione + ADP + phosphate + H(+)
  3. 15-deoxy-Delta(12,14)-prostaglandin J2 + glutathione = 15-deoxy-Delta(12,14)-prostaglandin J2-S-(R)-glutathione

  Catalysed by AGXT2, GSS, MGST3

• Xaa-L-Pro dipeptideReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. L-proline(out) + L-alanine(in) + Na(+)(out) = L-proline(in) + L-alanine(out) + Na(+)(in)
  3. Xaa-L-Pro dipeptide + H2O = an L-alpha-amino acid + L-proline

  Catalysed by AGXT2, SLC1A4, PEPDinner side of the membrane, outer side of the membrane

• (6R)-10-formyltetrahydrofolateReach from here →
  1. N(omega)-methyl-L-arginine + glyoxylate = 5-(3-methylguanidino)-2-oxopentanoate + glycine
  2. (6R)-5,10-methylene-5,6,7,8-tetrahydrofolate + glycine + H2O = (6S)-5,6,7,8-tetrahydrofolate + L-serine
  3. (6S)-5,6,7,8-tetrahydrofolate + formate + ATP = (6R)-10-formyltetrahydrofolate + ADP + phosphate

  Catalysed by AGXT2, SHMT1, SHMT2, MTHFD1 and 1 more

• (5S)-hydroxy-(6E,8Z,11Z,14Z,17Z)-eicosapentaenoateReach from here →
  1. N(omega)-methyl-L-arginine + glyoxylate = 5-(3-methylguanidino)-2-oxopentanoate + glycine
  2. gamma-L-glutamyl-L-cysteine + glycine + ATP = glutathione + ADP + phosphate + H(+)
  3. (5S)-hydroperoxy-(6E,8Z,11Z,14Z,17Z)-eicosapentaenoate + 2 glutathione = (5S)-hydroxy-(6E,8Z,11Z,14Z,17Z)-eicosapentaenoate + glutathione disulfide + H2O

  Catalysed by AGXT2, GSS, GPX1, GPX4

• (12S)-hydroxy-(5Z,8Z,10E,14Z,17Z)-eicosapentaenoateReach from here →
  1. N(omega)-methyl-L-arginine + glyoxylate = 5-(3-methylguanidino)-2-oxopentanoate + glycine
  2. gamma-L-glutamyl-L-cysteine + glycine + ATP = glutathione + ADP + phosphate + H(+)
  3. (12S)-hydroperoxy-(5Z,8Z,10E,14Z,17Z)-eicosapentaenoate + 2 glutathione = (12S)-hydroxy-(5Z,8Z,10E,14Z,17Z)-eicosapentaenoate + glutathione disulfide + H2O

  Catalysed by AGXT2, GSS, GPX1, GPX4

• (15S)-hydroxy-(11Z,13E)-eicosadienoateReach from here →
  1. N(omega)-methyl-L-arginine + glyoxylate = 5-(3-methylguanidino)-2-oxopentanoate + glycine
  2. gamma-L-glutamyl-L-cysteine + glycine + ATP = glutathione + ADP + phosphate + H(+)
  3. (15S)-hydroperoxy-(11Z,13E)-eicosadienoate + 2 glutathione = (15S)-hydroxy-(11Z,13E)-eicosadienoate + glutathione disulfide + H2O

  Catalysed by AGXT2, GSS, GPX1, GPX4

• (17S)-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoateReach from here →
  1. N(omega)-methyl-L-arginine + glyoxylate = 5-(3-methylguanidino)-2-oxopentanoate + glycine
  2. gamma-L-glutamyl-L-cysteine + glycine + ATP = glutathione + ADP + phosphate + H(+)
  3. (17S)-hydroperoxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate + 2 glutathione = (17S)-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate + glutathione disulfide + H2O

  Catalysed by AGXT2, GSS, GPX1, GPX4

• a hydroxy-1,2-diacyl-glycero-3-phosphocholineReach from here →
  1. N(omega)-methyl-L-arginine + glyoxylate = 5-(3-methylguanidino)-2-oxopentanoate + glycine
  2. gamma-L-glutamyl-L-cysteine + glycine + ATP = glutathione + ADP + phosphate + H(+)
  3. a hydroperoxy-1,2-diacyl-glycero-3-phosphocholine + 2 glutathione = a hydroxy-1,2-diacyl-glycero-3-phosphocholine + glutathione disulfide + H2O

  Catalysed by AGXT2, GSS, GPX4

• biocytinReach from here →
  1. N(omega)-methyl-L-arginine(in) + L-arginine(out) = N(omega)-methyl-L-arginine(out) + L-arginine(in)
  2. L-lysine(out) + L-arginine(in) = L-lysine(in) + L-arginine(out)
  3. biocytin + H2O = biotin + L-lysine

  Catalysed by SLC25A29, SLC7A9, SLC7A6, BTDinner side of the membrane, outer side of the membrane

• glycodeoxycholate 3-sulfateReach from here →
  1. N(omega)-methyl-L-arginine + glyoxylate = 5-(3-methylguanidino)-2-oxopentanoate + glycine
  2. Glycodeoxycholate amidohydrolase
  3. glycodeoxycholate + 3'-phosphoadenylyl sulfate = glycodeoxycholate 3-sulfate + adenosine 3',5'-bisphosphate + H(+)

  Catalysed by AGXT2, SULT2A1cytosol

• 3',5'-diiodo-L-thyronineReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. 3',5'-diiodo-L-thyronine + iodide + A + H(+) = 3,3',5'-triiodo-L-thyronine + AH2

  Catalysed by AGXT2, MOCOS, DIO3

• 5-(3,3-dimethylguanidino)-2-oxopentanoateReach from here →
  1. N(omega)-methyl-L-arginine(in) + L-arginine(out) = N(omega)-methyl-L-arginine(out) + L-arginine(in)
  2. N(omega),N(omega)-dimethyl-L-arginine(in) + L-arginine(out) = N(omega),N(omega)-dimethyl-L-arginine(out) + L-arginine(in)
  3. N(omega),N(omega)-dimethyl-L-arginine + pyruvate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + L-alanine

  Catalysed by SLC25A29, SLC25A2, AGXT2inner side of the membrane, outer side of the membraneOne of 8 routes

• 5-(3,3'-dimethylguanidino)-2-oxopentanoateReach 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. N(omega),N('omega)-dimethyl-L-arginine + pyruvate = 5-(3,3'-dimethylguanidino)-2-oxopentanoate + L-alanine

  Catalysed by AGXT2One of 4 routes

• (6R)-5,10-methylenetetrahydrofolic acidReach from here →
  1. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  2. methylamine:oxygen oxidoreductase (deaminating) (copper-containing)
  3. formaldehyde to 5,10-methylene-THF conversion

  Catalysed by DDAH1, AOC2, AOC1, AOC3cytosolOne of 8 routes

• S-disulfanyl-L-cysteineReach from here →
  1. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  2. transport of citrulline and cysteine (cytosol to extracellular)
  3. S-sulfanyl-L-cysteine + L-cysteine = S-disulfanyl-L-cysteine + L-alanine

  Catalysed by DDAH1, SLC7A6, CARS2extracellular space, cytosol

• (5Z)-dodecenoyl-CoAReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. acetyl-CoA C-acyltransferase (3-oxomyrist-7-enoyl-CoA)

  Catalysed by AGXT2, HADHA, ACAA2, HADHBmitochondrial matrixOne of 2 routes

• 3-iodothyronamineReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. 3-iodothyronamine + iodide + A + H(+) = 3,5-diiodothyronamine + AH2

  Catalysed by AGXT2, MOCOS, DIO1, DIO3One of 2 routes

• (11Z)-docosenoyl-CoA(4-)Reach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. long-chain-fatty-acid-CoA ligase (cis-cetoleic acid)

  Catalysed by AGXT2, SLC27A2, ACSL4, ACSL3 and 5 moremitochondrial matrix, cytosolOne of 5 routes

• 3-iodo-L-thyronineReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. 3-iodo-L-thyronine + iodide + A + H(+) = 3,5-diiodo-L-thyronine + AH2

  Catalysed by AGXT2, MOCOS, DIO1, DIO3One of 2 routes

• (7Z)-tetradecenoyl-CoAReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. long-chain-fatty-acid-CoA ligase ((7Z)-tetradecenoic acid)

  Catalysed by AGXT2, SLC27A2, ACSL4, ACSL3 and 5 moremitochondrial matrix, cytosolOne of 8 routes