N(omega)-methyl-L-arginine

Three steps

• CHEBI:15765Reach from here →
  1. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  2. transport of citrulline and tyrosine (cytosol to extracellular)
  3. L-Tyrosine,tetrahydrobiopterin:oxygen oxidoreductase (3-hydroxylating)

  Catalysed by DDAH1, SLC7A6, THextracellular space, cytosolOne of 5 routes

• bromideReach 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. 2-bromoacetaldehyde:glutathione S-(formylmethyl)transferase

  Catalysed by AGXT2, GSS, MGST3, GSTA4 and 15 morecytosolOne of 2 routes

• N-carbamoyl-L-aspartic acidReach from here →
  1. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  2. Carbamoyl-phosphate:L-ornithine carbamoyltransferase
  3. carbamoyl-phosphate:L-aspartate carbamoyltransferase

  Catalysed by DDAH1, OTC, CADmitochondrial matrix, cytosolOne of 2 routes

• alpha-D-glucosamine 6-phosphateReach from here →
  1. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  2. transport of citrulline and glutamine (cytosol to extracellular)
  3. L-glutamine:D-fructose-6-phosphate isomerase (deaminating)

  Catalysed by DDAH1, SLC7A6, GFPT2, GFPT1extracellular space, cytosol

• thioredoxin dithiolReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. L-Alanine:tRNA(Ala) ligase (AMP-forming)
  3. glycyl-tRNA(gly) phosphorylation

  Catalysed by AGXT2, AARS1cytosolOne of 4 routes

• methanethiolReach from here →
  1. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  2. methylamine:oxygen oxidoreductase (deaminating) (copper-containing)
  3. methanethiol + O2 + H2O = hydrogen sulfide + formaldehyde + H2O2 + H(+)

  Catalysed by DDAH1, AOC2, AOC1, AOC3 and 1 morecytosol

• a halide anionReach 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. RX + glutathione = an S-substituted glutathione + a halide anion + H(+)

  Catalysed by AGXT2, GSS, GSTT4, GSTA4 and 21 more

• sulfateReach 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 sulfate (cytosol to extracellular)

  Catalysed by SLC25A29, SLC6A14, SLC26A6inner side of the membrane, outer side of the membrane, extracellular space, cytosolOne of 3 routes

• 2-methyl-3-oxopropanoic 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

• nitriteReach 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. 4 nitric oxide + O2 + 2 H2O = 4 nitrite + 4 H(+)

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

• 11-cis-retinolReach 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. Palmitoyl-CoA:retinol O-acyltransferase

  Catalysed by AGXT2, DGAT1, LRAT, AWAT1 and 2 moremitochondrial matrix, cytosol

• cob(II)alaminReach 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. 2 cob(II)alamin + A + 2 H2O + 2 H(+) = 2 aquacob(III)alamin + AH2

  Catalysed by AGXT2, MOCOS, MTRR

• lithocholic acidReach 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 lithocholate (cytosol to extracellular)

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

• iodideReach from here →
  1. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  2. transport of citrulline and tyrosine (cytosol to extracellular)
  3. thyroid peroxidase (iodine)

  Catalysed by DDAH1, SLC7A6, TPOextracellular space, cytosolOne of 25 routes

• oxaloacetateReach 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:carbon-dioxide ligase (ADP-forming)

  Catalysed by AGXT2, PCmitochondrial matrixOne of 9 routes

• selaneReach 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. L-selenocysteine selenide-lyase (L-alanine-forming)

  Catalysed by AGXT2, SCLYcytosolOne of 3 routes

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

  Catalysed by DDAH1, SLC7A9, ACY1extracellular space, cytosol

• 2-phenylacetamideReach from here →
  1. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  2. transport of citrulline and phenylalanine (cytosol to extracellular)
  3. L-phenylalanine:oxygen 2-oxidoreductase (decarboxylating)

  Catalysed by DDAH1, SLC7A6, EPXextracellular space, cytosol

• anthranilateReach 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 + H2O = anthranilate + L-alanine + H(+)

  Catalysed by AGXT2, KYNU

• D-alanyl-D-alanineReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. alanine racemase
  3. Formation of Alanylalanine

  Catalysed by AGXT2cytosol

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

  Catalysed by DDAH1, SLC7A6, MARS1extracellular space, cytosol

• (S)-lactateReach 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. (S)-lactate + NAD(+) = pyruvate + NADH + H(+)

  Catalysed by AGXT2, LDHA, LDHB, LDHC and 2 more

• 3'-deoxy-3',4'-didehydro-CTPReach 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. CTP + AH2 + S-adenosyl-L-methionine = 3'-deoxy-3',4'-didehydro-CTP + 5'-deoxyadenosine + L-methionine + A + H2O + H(+)

  Catalysed by AGXT2, MOCOS, RSAD2

• cyanamideReach 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. urea = cyanamide + H2O

  Catalysed by SLC25A29, ARG1, CA1, CA2inner side of the membrane, outer side of the membrane, cytosol

• pyridoxineReach 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 phosphohydrolase

  Catalysed by AGXT2, SCLY, PHOSPHO2, PDXPcytosolOne of 2 routes

• 4-methylsulfanyl-2-oxobutanoateReach from here →
  1. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  2. transport of citrulline and methionine (cytosol to extracellular)
  3. glyoxylate + L-methionine = 4-methylsulfanyl-2-oxobutanoate + glycine

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

• N-[(S)-lactoyl]-L-phenylalanineReach from here →
  1. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  2. transport of citrulline and phenylalanine (cytosol to extracellular)
  3. (S)-lactate + L-phenylalanine = N-[(S)-lactoyl]-L-phenylalanine + H2O

  Catalysed by DDAH1, SLC7A6, CNDP2extracellular space, cytosol

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

  Catalysed by DDAH1, SLC7A6, SDS, SDSLextracellular space, cytosolOne of 7 routes

• tryptamineReach from here →
  1. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  2. transport of citrulline and tryptophan (cytosol to extracellular)
  3. L-tryptophan decarboxy-lyase

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

• 2-oxoglutaramateReach from here →
  1. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  2. transport of citrulline and glutamine (cytosol to extracellular)
  3. L-Glutamine:pyruvate aminotransferase

  Catalysed by DDAH1, SLC7A6, KYAT1extracellular space, cytosolOne of 5 routes

• (S)-2-hydroxyglutarateReach 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. (S)-2-hydroxyglutarate + A = 2-oxoglutarate + AH2

  Catalysed by AGXT2, MOCOS, L2HGDH

• 3-fumarylpyruvateReach 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-fumarylpyruvate + H2O = fumarate + pyruvate + H(+)

  Catalysed by AGXT2, FAHD1

• trans-1,2-dithiane-4,5-diolReach 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. selenocysteine lyase (dithiothreitol)

  Catalysed by AGXT2, SCLYcytosol

• creatineReach from here →
  1. N(omega)-methyl-L-arginine(in) + L-arginine(out) = N(omega)-methyl-L-arginine(out) + L-arginine(in)
  2. L-Arginine:glycine amidinotransferase
  3. S-Adenosyl-L-methionine:guanidinoacetate N-methyltransferase

  Catalysed by SLC25A29, GATM, GAMTinner side of the membrane, outer side of the membrane, cytosolOne of 2 routes

• N-acetyl-L-aspartateReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. oxaloacetate + L-alanine = L-aspartate + pyruvate
  3. acetyl-CoA:L-aspartate N-acetyltransferase

  Catalysed by AGXT2, NAT8Lmitochondrial matrixOne of 2 routes

• bilirubin IXalphaReach 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 bilirubin and GSH (cytosol to extracellular)

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

• oxalic 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 oxalate (cytosol to extracellular)

  Catalysed by SLC25A29, SLC6A14, SLC26A6inner side of the membrane, outer side of the membrane, extracellular space, cytosolOne of 3 routes

• (R)-3-hydroxybutyric 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 (R)-3-hydroxybutanoate and pyruvate (cytosol to extracellular)

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

• taurolithocholateReach 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 taurolithocholate (cytosol to extracellular)

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

• 3-hydroxypyruvateReach 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-serine + pyruvate = 3-hydroxypyruvate + L-alanine

  Catalysed by AGXT2, AGXTOne of 2 routes

• CHEBI:17208Reach 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:dehydroascorbate oxidoreductase

  Catalysed by AGXT2, GSScytosol

• homocysteineReach 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. Formation of Homocystine

  Catalysed by AGXT2, GSScytosol

• L-glutamic 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-oxo-acid aminotransferase

  Catalysed by DDAH1, SLC7A9, OATextracellular space, cytosol, mitochondrial matrix

• anilineReach 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:arylamine N-acetyltransferase

  Catalysed by AGXT2, NAT2, NAT1mitochondrial matrix, cytosol

• aceneuramateReach 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. aceneuramate = aldehydo-N-acetyl-D-mannosamine + pyruvate

  Catalysed by AGXT2, NPL

• CHEBI:17312Reach 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. N1,N12-diacetylspermine to N1-acetylspermine conversion

  Catalysed by AGXT2mitochondrial matrix, cytosolOne of 2 routes

• 5'-deoxyadenosineReach 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(1)-methylguanosine(37) in tRNA(Phe) + pyruvate + S-adenosyl-L-methionine = 4-demethylwyosine(37) in tRNA(Phe) + 5'-deoxyadenosine + L-methionine + CO2 + H2O

  Catalysed by AGXT2, TYW1B, TYW1One of 5 routes

• sulfiteReach 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. thiosulfate + 2 glutathione = glutathione disulfide + hydrogen sulfide + sulfite + 2 H(+)

  Catalysed by AGXT2, GSS, TSTD1One of 2 routes

• CHEBI:17380Reach from here →
  1. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  2. transport of citrulline and tryptophan (cytosol to extracellular)
  3. Transport of 3-Hydroxy-L-Kynurenine

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

• (S)-1-pyrroline-5-carboxylateReach from here →
  1. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  2. transport of citrulline and proline (cytosol to extracellular)
  3. L-proline:(acceptor) oxidoreductase

  Catalysed by DDAH1, SLC7A6, PRODH2extracellular space, cytosolOne of 3 routes