N(omega)-methyl-L-arginine

Three steps

• prostaglandin F2alphaReach 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. transport of GSH and prostaglandin F2alpha (cytosol to extracellular)

  Catalysed by AGXT2, GSS, SLCO2A1cytosol, extracellular spaceOne of 2 routes

• prostaglandin H2Reach 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. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + A + H2O

  Catalysed by AGXT2, MOCOS, PTGS1, PTGS2One of 4 routes

• prostaglandin D2Reach 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. transport of GSH and prostaglandin D2 (cytosol to extracellular)

  Catalysed by AGXT2, GSS, SLCO2A1cytosol, extracellular spaceOne of 2 routes

• (15S)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach 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. (15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate + AH2 = (15S)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoate + A + H2O

  Catalysed by AGXT2, MOCOS, TBXAS1, PTGS2 and 1 moreOne of 3 routes

• 7,8-dihydrofolateReach from here →
  1. N(omega)-methyl-L-arginine + glyoxylate = 5-(3-methylguanidino)-2-oxopentanoate + glycine
  2. 5,10-Methylenetetrahydrofolate:glycine hydroxymethyltransferase
  3. 5,6,7,8-tetrahydrofolate:NAD+ oxidoreductase

  Catalysed by AGXT2, SHMT1, DHFR, DHFR2cytosolOne of 3 routes

• 5-formimidoyltetrahydrofolateReach from here →
  1. N(omega)-methyl-L-arginine + glyoxylate = 5-(3-methylguanidino)-2-oxopentanoate + glycine
  2. 5,10-Methylenetetrahydrofolate:glycine hydroxymethyltransferase
  3. 5-Formiminotetrahydrofolate:L-glutamate N-formiminotransferase

  Catalysed by AGXT2, SHMT1, FTCDcytosolOne of 2 routes

• leukotriene A4Reach 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. transport of GSH and leukotriene A4 (cytosol to extracellular)

  Catalysed by AGXT2, GSS, SLCO2A1cytosol, extracellular spaceOne of 3 routes

• (R)-S-lactoylglutathioneReach 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. (R)-S-Lactoylglutathione methylglyoxal-lyase (isomerizing)

  Catalysed by AGXT2, GSS, GLO1, GLOD4cytosolOne of 3 routes

• carnosineReach from here →
  1. N(omega)-methyl-L-arginine(in) + L-arginine(out) = N(omega)-methyl-L-arginine(out) + L-arginine(in)
  2. L-histidine(out) + L-arginine(in) + Na(+)(out) = L-histidine(in) + L-arginine(out) + Na(+)(in)
  3. beta-alanine + L-histidine + ATP = carnosine + ADP + phosphate + H(+)

  Catalysed by SLC25A29, SLC7A6, CARNS1inner side of the membrane, outer side of the membraneOne of 2 routes

• 2-oxoadipateReach 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. L-2-aminoadipate + glyoxylate = 2-oxoadipate + glycine

  Catalysed by AGXT2, AADAT

• L-dopaReach from here →
  1. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  2. transport of citrulline and phenylalanine (cytosol to extracellular)
  3. L-dopa(out) + L-phenylalanine(in) = L-dopa(in) + L-phenylalanine(out)

  Catalysed by DDAH1, SLC7A6, SLC7A8extracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 3 routes

• N(6)-(1,2-dicarboxyethyl)-AMPReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. oxaloacetate + L-alanine = L-aspartate + pyruvate
  3. IMP:L-aspartate ligase (GDP-forming)

  Catalysed by AGXT2, ADSS2, ADSS1cytosolOne of 2 routes

• D-ornithineReach from here →
  1. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  2. Amino Acid-Polyamine-Organocation (Apc) Tcdb:2.A.3.8.15
  3. D-ornithine(in) + L-ornithine(out) = D-ornithine(out) + L-ornithine(in)

  Catalysed by DDAH1, SLC7A9, SLC25A2extracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• 2-oxo-3-sulfanylpropanoateReach from here →
  1. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  2. transport of citrulline and cysteine (cytosol to extracellular)
  3. L-Cysteine:2-oxoglutarate aminotransferase

  Catalysed by DDAH1, SLC7A6, GOT2, GOT1extracellular space, cytosolOne of 5 routes

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

  Catalysed by DDAH1, AOC2, AOC1, AOC3 and 6 morecytosolOne of 3 routes

• 2-methyl-3-oxopropanoateReach 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 = 2-methyl-3-oxopropanoate + L-alanine

  Catalysed by AGXT2

• sphing-4-enineReach 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. acyl-CoA:sphingosine N-acyltransferase

  Catalysed by AGXT2, ASAH1, ACER2, ACER1 and 1 moremitochondrial matrix, Golgi apparatusOne of 2 routes

• spermidineReach 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 7 routes

• L-dopaquinoneReach from here →
  1. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  2. transport of citrulline and tyrosine (cytosol to extracellular)
  3. L-Tyrosine,L-dopa:oxygen oxidoreductase

  Catalysed by DDAH1, SLC7A6, TYRextracellular space, cytosolOne of 2 routes

• L-saccharopineReach from here →
  1. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  2. transport of citrulline and lysine (cytosol to extracellular)
  3. N6-(L-1,3-Dicarboxypropyl)-L-lysine:NADP+ oxidoreductase (L-lysine-forming)

  Catalysed by DDAH1, SLC7A5, SLC7A6, AASSextracellular space, cytosol, mitochondrial matrixOne of 2 routes

• dimethylamineReach 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. Nomega,Nomega'-dimethyl-L-arginine dimethylamidohydrolase

  Catalysed by SLC25A29, SLC25A2, DDAH1inner side of the membrane, outer side of the membrane, cytosolOne of 2 routes

• L-glutamate 5-semialdehydeReach from here →
  1. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  2. Amino Acid-Polyamine-Organocation (Apc) Tcdb:2.A.3.8.15
  3. L-ornithine + 2-oxoglutarate = L-glutamate 5-semialdehyde + L-glutamate

  Catalysed by DDAH1, SLC7A9, OATextracellular space, cytosol

• N(4)-(beta-N-acetyl-D-glucosaminyl)-L-asparagineReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  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, AGA

• porphobilinogenReach from here →
  1. N(omega)-methyl-L-arginine + glyoxylate = 5-(3-methylguanidino)-2-oxopentanoate + glycine
  2. succinyl-CoA:glycine C-succinyltransferase (decarboxylating)
  3. 5-aminolevulinate hydro-lyase (adding 5-aminolevulinate and cyclizing

  Catalysed by AGXT2, ALAS1, ALAS2, CPNE7 and 1 moremitochondrial matrix, cytosolOne of 2 routes

• L,L-cystathionineReach 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. N-acetylglutamate synthase (N-acetyl-L-cystathionine)

  Catalysed by AGXT2, NAGSmitochondrial matrix

• gamma-L-glutamyl-L-cysteineReach from here →
  1. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  2. transport of citrulline and cysteine (cytosol to extracellular)
  3. L-glutamate:L-cysteine gamma-ligase (ADP-forming)

  Catalysed by DDAH1, SLC7A6, GCLC, GCLMextracellular space, cytosolOne of 2 routes

• 6-amino-2-oxohexanoateReach from here →
  1. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  2. transport of citrulline and lysine (cytosol to extracellular)
  3. L-lysine:oxygen 2-oxidoreductase (deaminating)

  Catalysed by DDAH1, SLC7A5, SLC7A6extracellular space, cytosol, peroxisome

• L-homocysteineReach from here →
  1. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  2. transport of citrulline and methionine (cytosol to extracellular)
  3. S-methyl-L-methionine + L-homocysteine = 2 L-methionine + H(+)

  Catalysed by DDAH1, SLC7A6, BHMT2extracellular space, cytosol

• N,N-dimethylglycineReach from here →
  1. N(omega)-methyl-L-arginine + glyoxylate = 5-(3-methylguanidino)-2-oxopentanoate + glycine
  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 AGXT2, PIPOX, DMGDH

• S-methyl-L-methionineReach from here →
  1. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  2. transport of citrulline and methionine (cytosol to extracellular)
  3. S-methyl-L-methionine + L-homocysteine = 2 L-methionine + H(+)

  Catalysed by DDAH1, SLC7A6, BHMT2extracellular space, cytosol

• N-acetylputrescineReach 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. acetyl-CoA:putrescine N-acetyltransferase

  Catalysed by SLC25A29, SLC3A2, SLC7A7, SAT1 and 1 moreinner side of the membrane, outer side of the membrane, extracellular space, cytosolOne of 2 routes

• 4-aminobutanalReach 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 + O2 + H2O = 4-aminobutanal + H2O2 + NH4(+)

  Catalysed by SLC25A29, SLC3A2, SLC7A7, AOC1inner side of the membrane, outer side of the membrane, extracellular space, cytosol

• glutathione disulfideReach 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. cystine to cysteine conversion

  Catalysed by SLC25A29, SLC7A9inner side of the membrane, outer side of the membrane, cytosolOne of 36 routes

• taurolithocholate 3-sulfateReach 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. transport of GSH and sulfotaurolithocholate (cytosol to extracellular)

  Catalysed by AGXT2, GSS, SLCO1A2, SLCO1B3cytosol, extracellular spaceOne of 2 routes

• N(1)-acetylspermidineReach 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. N(1)-acetylspermidine + O2 + H2O = 3-acetamidopropanal + putrescine + H2O2

  Catalysed by SLC25A29, SLC3A2, SLC7A7, PAOXinner side of the membrane, outer side of the membrane, extracellular space, cytosol

• an acyl-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. acyl-CoA:sphingosine N-acyltransferase

  Catalysed by AGXT2, ASAH1, ACER2, ACER1 and 1 moremitochondrial matrix, Golgi apparatusOne of 2 routes

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

  Catalysed by AGXT2, GSS, CHAC2, CHAC1

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

  Catalysed by DDAH1, SLC7A5, SLC7A6, HDCextracellular space, cytosolOne of 4 routes

• L-2-aminopentanoateReach 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. 2-oxopentanoate + N(omega),N(omega)-dimethyl-L-arginine = 5-(3,3-dimethylguanidino)-2-oxopentanoate + L-2-aminopentanoate

  Catalysed by SLC25A29, SLC25A2, AGXT2inner side of the membrane, outer side of the membraneOne of 2 routes

• (2S)-2-[5-amino-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamido]succinateReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  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. N(omega)-methyl-L-arginine + glyoxylate = 5-(3-methylguanidino)-2-oxopentanoate + glycine
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. transport of GSH and thyroxine (cytosol to extracellular)

  Catalysed by AGXT2, GSS, SLCO1A2, SLCO1B3cytosol, extracellular spaceOne of 2 routes

• kynurenateReach 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. L-kynurenine + glyoxylate = kynurenate + glycine + H2O

  Catalysed by AGXT2, KYAT3, AADATOne of 14 routes

• L-2-aminohexanoateReach 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. 2-oxohexanoate + N(omega),N(omega)-dimethyl-L-arginine = L-2-aminohexanoate + 5-(3,3-dimethylguanidino)-2-oxopentanoate

  Catalysed by SLC25A29, SLC25A2, AGXT2inner side of the membrane, outer side of the membraneOne of 2 routes

• 5-amino-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamideReach from here →
  1. N(omega)-methyl-L-arginine + glyoxylate = 5-(3-methylguanidino)-2-oxopentanoate + glycine
  2. 5,10-Methylenetetrahydrofolate:glycine hydroxymethyltransferase
  3. phosphoribosylaminoimidazolecarboxamide formyltransferase (10-formyl-THF)

  Catalysed by AGXT2, SHMT1, ATICcytosol

• (3Z)-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-5-enoyl-CoA)

  Catalysed by AGXT2, HADHA, ACAA2, HADHBmitochondrial matrixOne of 3 routes

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

  Catalysed by DDAH1, SLC7A6, CARS2extracellular space, cytosol

• N-formyl-L-kynurenineReach 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 = N-formyl-L-kynurenine

  Catalysed by DDAH1, SLC7A9, SLC3A1, SLC7A6 and 3 moreextracellular space, cytosolOne of 2 routes

• (3S)-citramalyl-CoAReach 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. (3S)-citramalyl-CoA = pyruvate + acetyl-CoA

  Catalysed by AGXT2, CLYBL

• L-2-aminoadipateReach 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. 2-oxoadipate + L-kynurenine = L-2-aminoadipate + kynurenate + H2O

  Catalysed by AGXT2, KYNU, AADAT

• (25R)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oyl-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. 3alpha,7alpha,12alpha-trihydroxy-5beta-cholestanoate:CoA ligase (AMP-forming)

  Catalysed by AGXT2, SLC27A2, SLC27A5mitochondrial matrix, endoplasmic reticulumOne of 3 routes