N(omega)-methyl-L-arginine

Three steps

• 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, DIO2One of 2 routes

• (R)-adrenaline 4'-O-sulfateReach 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 + 3'-phosphoadenylyl sulfate = (R)-adrenaline 4'-O-sulfate + adenosine 3',5'-bisphosphate + H(+)

  Catalysed by DDAH1, MAOA, MAOB, SULT1A3 and 1 more

• 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. L-thyronine + iodide + A + H(+) = 3-iodo-L-thyronine + AH2

  Catalysed by AGXT2, MOCOS, DIO3

• thyronamineReach 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. thyronamine + iodide + A + H(+) = 3-iodothyronamine + AH2

  Catalysed by AGXT2, MOCOS, DIO3

• 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, DIO2One of 2 routes

• 3,3'-diiodothyronamineReach 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'-diiodothyronamine + iodide + A + H(+) = 3,3',5'-triiodothyronamine + AH2

  Catalysed by AGXT2, MOCOS, DIO1, DIO2One of 2 routes

• 3',5'-diiodothyronamineReach 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'-diiodothyronamine + iodide + A + H(+) = 3,3',5'-triiodothyronamine + AH2

  Catalysed by AGXT2, MOCOS, DIO3

• 3,3',5'-triiodothyronamineReach 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'-triiodothyronamine + iodide + A + H(+) = 3,3',5,5'-tetraiodothyronamine + AH2

  Catalysed by AGXT2, MOCOS, DIO3

• (4Z,7Z,10Z,13Z)-hexadecatetraenoyl-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 (C18:4->C16:4), Mitochondrial

  Catalysed by AGXT2, HADHA, ACADVL, HADHBmitochondrial matrixOne of 3 routes

• (7Z,10Z)-hexadecadienoyl-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 Trans (C18:2->C16:2), Mitochondrial

  Catalysed by AGXT2, HADHA, ACADVL, HADHBmitochondrial matrix

• (4Z,7Z)-decadienoyl-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 (C12:3->C10:2), Mitochondrial

  Catalysed by AGXT2, ECHS1, ACAA2, HADHmitochondrial matrixOne of 2 routes

• (5Z)-octenoyl-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 (C10:2->C8:1), Mitochondrial

  Catalysed by AGXT2, ECHS1, ACAA2, HADHmitochondrial matrixOne of 2 routes

• 3-(glutathion-S-yl)-4-hydroxynonanalReach 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. (E)-4-hydroxynon-2-enal + glutathione = 3-(glutathion-S-yl)-4-hydroxynonanal

  Catalysed by AGXT2, GSS, GSTP1

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

  Catalysed by AGXT2, SULT2A1cytosol

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

  Catalysed by AGXT2, BAAT, SULT2A1

• deoxycholateReach from here →
  1. N(omega)-methyl-L-arginine + glyoxylate = 5-(3-methylguanidino)-2-oxopentanoate + glycine
  2. Glycodeoxycholate amidohydrolase
  3. Glycodeoxycholate amidohydrolase

  Catalysed by AGXT2cytosol

• a quinolReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. trans-4-hydroxy-L-proline(out) + L-alanine(in) + Na(+)(out) = trans-4-hydroxy-L-proline(in) + L-alanine(out) + Na(+)(in)
  3. trans-4-hydroxy-L-proline + a quinone = (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate + a quinol + H(+)

  Catalysed by AGXT2, SLC1A4, PRODH2inner side of the membrane, outer side of the membraneOne of 3 routes

• hypochlorous acidReach 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. Peroxidase

  Catalysed by SLC25A29, SLC6A14, LPOinner side of the membrane, outer side of the membrane, extracellular space, cytosolOne of 4 routes

• potassium atomReach 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 chloride (cytosol to extracellular)

  Catalysed by SLC25A29, SLC6A14, SLC12A2, SLC12A1inner side of the membrane, outer side of the membrane, extracellular space, cytosolOne of 3 routes

• CHEBI:27540Reach 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. medium-chain acyl-CoA ligase (hexanoic acid)

  Catalysed by AGXT2, ACSM4, ACSM1, ACSM2A and 3 moremitochondrial matrix, cytosolOne of 6 routes

• CHEBI:27760Reach 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. Selenocystathionine Lysteine-lyase (deaminating)

  Catalysed by AGXT2, SCLY, CTHcytosol

• elaidic acidReach 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 (elaidate)

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

• 5-hydroxytryptophanReach from here →
  1. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  2. transport of citrulline and tryptophan (cytosol to extracellular)
  3. L-Tryptophan, Tetrahydrobiopterin:Oxygen Oxidoreductase (5-Hydroxylating)

  Catalysed by DDAH1, SLC7A9, SLC3A1, SLC7A6 and 2 moreextracellular space, cytosolOne of 2 routes

• 5(S)-HETEReach from here →
  1. N(omega)-methyl-L-arginine + glyoxylate = 5-(3-methylguanidino)-2-oxopentanoate + glycine
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. Glutathione: 5-HPETE oxidoreductase

  Catalysed by AGXT2, GSS, GPX5, GPX1 and 7 morecytosolOne of 2 routes

• CHEBI:28701Reach 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. Propanoyl-CoA:acetyl-CoA C-acyltransferase

  Catalysed by AGXT2, ACAA1, SCP2, MYO5Bmitochondrial matrix, peroxisomeOne of 7 routes

• 3-disulfanyl-L-alanineReach from here →
  1. N(omega)-methyl-L-arginine(in) + L-arginine(out) = N(omega)-methyl-L-arginine(out) + L-arginine(in)
  2. L-cystine(out) + L-arginine(in) = L-cystine(in) + L-arginine(out)
  3. L-cystine thiocysteine-lyase (deaminating

  Catalysed by SLC25A29, SLC7A9, CTHinner side of the membrane, outer side of the membrane, cytosol

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

  Catalysed by DDAH1, SLC7A6, NAGSextracellular space, cytosol, mitochondrial matrix

• a dicarboxylateReach from here →
  1. N(omega)-methyl-L-arginine + glyoxylate = 5-(3-methylguanidino)-2-oxopentanoate + glycine
  2. Hippurate (Benzoylglycinate) Formation
  3. N-benzoylglycine(out) + a dicarboxylate(in) = N-benzoylglycine(in) + a dicarboxylate(out)

  Catalysed by AGXT2, SLC22A6, SLC22A8mitochondrial matrix, inner side of the membrane, outer side of the membraneOne of 2 routes

• L-ascorbic 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. L-dehydroascorbate + 2 glutathione = glutathione disulfide + L-ascorbate

  Catalysed by AGXT2, GSS, CLIC1, GSTO1 and 1 more

• K(+)Reach from here →
  1. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  2. transport of citrulline and cysteine (cytosol to extracellular)
  3. K(+)(in) + L-cysteine(out) + 3 Na(+)(out) + H(+)(out) = K(+)(out) + L-cysteine(in) + 3 Na(+)(in) + H(+)(in)

  Catalysed by DDAH1, SLC7A6, SLC1A1extracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 4 routes

• Cys-tRNA(Cys)Reach from here →
  1. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  2. transport of citrulline and cysteine (cytosol to extracellular)
  3. L-Cysteine:tRNA(Cys) ligase (AMP-forming)

  Catalysed by DDAH1, SLC7A6, CARS1extracellular space, cytosol

• Phe-tRNA(Phe)Reach from here →
  1. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  2. transport of citrulline and phenylalanine (cytosol to extracellular)
  3. L-Phenylalanine:tRNA(Ala) ligase (AMP-forming)

  Catalysed by DDAH1, SLC7A6, FARSB, FARSAextracellular space, cytosol

• Asp-tRNA(Asp)Reach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. oxaloacetate + L-alanine = L-aspartate + pyruvate
  3. L-Aspartate:tRNA(Asp) ligase (AMP-forming)

  Catalysed by AGXT2, DARS1cytosol

• Trp-tRNA(Trp)Reach from here →
  1. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  2. transport of citrulline and tryptophan (cytosol to extracellular)
  3. L-Tryptophan -tRNA(Trp) ligase (AMP-forming)

  Catalysed by DDAH1, SLC7A9, SLC3A1, SLC7A6 and 1 moreextracellular space, cytosol

• Ile-tRNA(Ile)Reach from here →
  1. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  2. transport of citrulline and isoleucine (cytosol to extracellular)
  3. L-Isoleucine:tRNA(Ile) ligase (AMP-forming)

  Catalysed by DDAH1, SLC7A6, IARS1extracellular space, cytosol

• Gln-tRNA(Gln)Reach from here →
  1. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  2. transport of citrulline and glutamine (cytosol to extracellular)
  3. L-Glutamine:tRNA(Gln) ligase (AMP-forming)

  Catalysed by DDAH1, SLC7A6, QARS1extracellular space, cytosol

• Asn-tRNA(Asn)Reach from here →
  1. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  2. transport of asparagine and citrulline (cytosol to extracellular)
  3. L-Asparagine:tRNA(Asn) ligase (AMP-forming)

  Catalysed by DDAH1, SLC7A9, SLC3A1, SLC7A6 and 1 moreextracellular space, cytosol

• hydrogenselenideReach 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. L-selenocysteine + AH2 = hydrogenselenide + L-alanine + A + H(+)

  Catalysed by AGXT2, MOCOS, SCLY

• cholateReach from here →
  1. N(omega)-methyl-L-arginine + glyoxylate = 5-(3-methylguanidino)-2-oxopentanoate + glycine
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. solute carrier organic anion transporter (cholate)

  Catalysed by AGXT2, GSS, SLCO1A2, SLCO1B3cytosol, extracellular spaceOne of 3 routes

• glycolateReach 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. glycolate + NADP(+) = glyoxylate + NADPH + H(+)

  Catalysed by AGXT2, GRHPROne of 3 routes

• hydrogen sulfideReach from here →
  1. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  2. transport of citrulline and cysteine (cytosol to extracellular)
  3. L-cysteine hydrogen-sulfide-lyase (deaminating

  Catalysed by DDAH1, SLC7A6, CTHextracellular space, cytosolOne of 3 routes

• acetateReach 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. transport of acetate and pyruvate (cytosol to extracellular)

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

• CHEBI:30249Reach from here →
  1. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  2. transport of citrulline and tryptophan (cytosol to extracellular)
  3. L-tryptophan:oxygen 2,3-oxidoreductase (decyclizing)

  Catalysed by DDAH1, SLC7A9, SLC3A1, SLC7A6 and 3 moreextracellular space, cytosol

• 3-acetamidopropanalReach from here →
  1. N(omega)-methyl-L-arginine(in) + L-arginine(out) = N(omega)-methyl-L-arginine(out) + L-arginine(in)
  2. Transport by Y+Lat-2 into Extracellular Space
  3. N1-acetylspermidine:oxygen oxidoreductase (3-acetamidopropanal-forming)

  Catalysed by SLC25A29, SLC3A2, SLC7A6, PAOX and 1 moreinner side of the membrane, outer side of the membrane, extracellular space, cytosolOne of 2 routes

• oxalateReach 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. glyoxylate + O2 + H2O = oxalate + H2O2 + H(+)

  Catalysed by AGXT2, HAO1

• formic acidReach 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 chloride and formate (cytosol to extracellular)

  Catalysed by SLC25A29, SLC6A14, SLC26A4inner side of the membrane, outer side of the membrane, extracellular space, cytosolOne of 4 routes

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

  Catalysed by AGXT2, KYNUcytosol

• propionic 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. transport of propanoate and pyruvate (cytosol to extracellular)

  Catalysed by AGXT2, SLC16A4, SLC16A5, SLC16A3 and 3 moreextracellular space, cytosolOne of 2 routes

• butyric 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. transport of butyrate and pyruvate (cytosol to extracellular)

  Catalysed by AGXT2, SLC16A4, SLC16A5, SLC16A3 and 3 moreextracellular space, cytosolOne of 2 routes

• malonic acidReach 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. Malonate Transport, Antiport with Chloride

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