N(omega)-methyl-L-arginine

Three steps

• 2-[(11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoyl]-sn-glycero-3-phosphocholineReach 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-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine + AH2 + O2 = 2-[(11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoyl]-sn-glycero-3-phosphocholine + A + H2O

  Catalysed by AGXT2, MOCOS, PTGS2

• 2-[(15R)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoyl]-sn-glycero-3-phosphocholineReach 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-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine + AH2 + O2 = 2-[(15R)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoyl]-sn-glycero-3-phosphocholine + A + H2O

  Catalysed by AGXT2, MOCOS, PTGS2

• 2-[(15S)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoyl]-sn-glycero-3-phosphocholineReach 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-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine + AH2 + O2 = 2-[(15S)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoyl]-sn-glycero-3-phosphocholine + A + H2O

  Catalysed by AGXT2, MOCOS, PTGS2

• 2-(prostaglandin H2)-sn-glycero-3-phosphoethanolamineReach 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-(prostaglandin G2)-sn-glycero-3-phosphoethanolamine + AH2 = 2-(prostaglandin H2)-sn-glycero-3-phosphoethanolamine + A + H2O

  Catalysed by AGXT2, MOCOS, PTGS2

• 2-(prostaglandin H2)-sn-glycero-3-phosphocholineReach 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-(prostaglandin G2)-sn-glycero-3-phosphocholine + AH2 = 2-(prostaglandin H2)-sn-glycero-3-phosphocholine + A + H2O

  Catalysed by AGXT2, MOCOS, PTGS2

• N-(4-oxoglutaryl)-L-cysteinylglycineReach from here →
  1. N(omega)-methyl-L-arginine + pyruvate = 5-(3-methylguanidino)-2-oxopentanoate + L-alanine
  2. gamma-glutamyltransferase (alanine)
  3. N-(4-oxoglutaryl)-L-cysteinylglycine + H2O = L-cysteinylglycine + 2-oxoglutarate

  Catalysed by AGXT2, GGTLC3, GGT1, GGT5 and 4 morecytosol

• S-methyl 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. apo-[alkylcobalamin reductase] + methylcob(III)alamin + glutathione = S-methyl glutathione + cob(I)alamin-[alkylcobalamin reductase] + H(+)

  Catalysed by AGXT2, GSS, MMACHC

• N-octanoyl-(2S)-hydroxyglycineReach 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. N-octanoyl-(2S)-hydroxyglycine = octanamide + glyoxylate

  Catalysed by AGXT2, PAMOne of 2 routes

• N-decanoyl-(2S)-hydroxyglycineReach 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. N-decanoyl-(2S)-hydroxyglycine = decanamide + glyoxylate

  Catalysed by AGXT2, PAMOne of 2 routes

• N-dodecanoyl-(2S)-hydroxyglycineReach 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. N-dodecanoyl-(2S)-hydroxyglycine = dodecanamide + glyoxylate

  Catalysed by AGXT2, PAMOne of 2 routes

• N-tetradecanoyl-(2S)-hydroxyglycineReach 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. N-tetradecanoyl-(2S)-hydroxyglycine = tetradecamide + glyoxylate

  Catalysed by AGXT2, PAMOne of 2 routes

• N-(9Z-octadecenoyl)-(2S)-hydroxyglycineReach 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. N-(9Z-octadecenoyl)-(2S)-hydroxyglycine = (9Z)-octadecenamide + glyoxylate

  Catalysed by AGXT2, PAMOne of 2 routes

• N-(9Z,12Z,15Z)-octadecatrienoyl-(2S)-hydroxyglycineReach 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. N-(9Z,12Z,15Z)-octadecatrienoyl-(2S)-hydroxyglycine = (9Z,12Z,15Z)-octadecatrienamide + glyoxylate

  Catalysed by AGXT2, PAM

• D-histidineReach 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-histidine(in) + L-ornithine(out) + H(+)(in) = D-histidine(out) + L-ornithine(in) + H(+)(out)

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

• L-homocarnosineReach from here →
  1. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  2. transport of citrulline and histidine (cytosol to extracellular)
  3. Formation of homocarnosine

  Catalysed by DDAH1, SLC7A5, SLC7A6, CARNS1extracellular space, cytosolOne of 2 routes

• 2,3-didehydrophenylalanineReach from here →
  1. N(omega)-methyl-L-arginine + glyoxylate = 5-(3-methylguanidino)-2-oxopentanoate + glycine
  2. glycyldehydrophenylalanine + H2O = 2,3-didehydrophenylalanine + glycine
  3. glycyldehydrophenylalanine + H2O = 2,3-didehydrophenylalanine + glycine

  Catalysed by AGXT2, DPEP1

• S-adenosylglutathioneReach 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. apo-[alkylcobalamin reductase] + adenosylcob(III)alamin + glutathione = S-adenosylglutathione + cob(I)alamin-[alkylcobalamin reductase] + H(+)

  Catalysed by AGXT2, GSS, MMACHC

• N(2)-formyl-N(1)-(5-phospho-beta-D-ribosyl)glycinamideReach from here →
  1. N(omega)-methyl-L-arginine + glyoxylate = 5-(3-methylguanidino)-2-oxopentanoate + glycine
  2. 5-phospho-beta-D-ribosylamine + glycine + ATP = N(1)-(5-phospho-beta-D-ribosyl)glycinamide + ADP + phosphate + H(+)
  3. N(1)-(5-phospho-beta-D-ribosyl)glycinamide + (6R)-10-formyltetrahydrofolate = N(2)-formyl-N(1)-(5-phospho-beta-D-ribosyl)glycinamide + (6S)-5,6,7,8-tetrahydrofolate + H(+)

  Catalysed by AGXT2, GART

• 2-formamido-N(1)-(5-O-phospho-beta-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. N(2)-formyl-N(1)-(5-phospho-beta-D-ribosyl)glycinamide + L-glutamine + ATP + H2O = 2-formamido-N(1)-(5-O-phospho-beta-D-ribosyl)acetamidine + L-glutamate + ADP + phosphate + H(+)

  Catalysed by DDAH1, SLC7A6, PFASextracellular space, cytosol

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

  Catalysed by DDAH1, SLC7A6, CMA1extracellular space, cytosolOne of 3 routes

• (7Z)-octadecenoyl-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. carnitine O-palmitoyltransferase ((7Z)-octadecenoyl-CoA)

  Catalysed by AGXT2, CPT1A, CPT1C, CPT1Bmitochondrial matrix, cytosolOne of 3 routes

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

  Catalysed by DDAH1, SLC7A6extracellular space, cytosolOne of 2 routes

• CHEBI:15345Reach 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. Acetoacetate:CoA ligase (AMP-forming)

  Catalysed by AGXT2, AACSmitochondrial matrix, cytosolOne of 2 routes

• cholineReach 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 choline (cytosol to extracellular)

  Catalysed by SLC25A29, SLC6A14, SLC5A7inner side of the membrane, outer side of the membrane, extracellular space, cytosolOne of 2 routes

• acetylcholineReach 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 acetylcholine and GSH (cytosol to extracellular)

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

• acetylpyruvateReach 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. acetylpyruvate + H2O = acetate + pyruvate + H(+)

  Catalysed by AGXT2, FAHD1

• all-trans-retinoic 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 pyruvate and retinoate (cytosol to extracellular)

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

• 4a-hydroxytetrahydrobiopterinReach from here →
  1. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  2. transport of citrulline and phenylalanine (cytosol to extracellular)
  3. L-phenylalanine,tetrahydrobiopterin:oxygen oxidoreductase(4-hydroxylating)

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

• CHEBI:15380Reach 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. 5-aminolevulinate synthase (2-amino-3-oxoadipate)

  Catalysed by AGXT2, ALAS1, CPNE7mitochondrial matrixOne of 8 routes

• CHEBI:15477Reach 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. glycine N-acyltransferase (2-methylbutyryl-CoA)

  Catalysed by AGXT2, GLYAT, GLYATL2, GLYATL1mitochondrial matrixOne of 3 routes

• 2-methylcrotonoyl-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. Production of Tiglylcarnitine

  Catalysed by AGXT2, CPT1A, CPT1Bmitochondrial matrix, cytosolOne of 2 routes

• isobutyryl-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-oxo-4-methyl-pentanoyl-CoA)

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

• 3-methylbut-2-enoyl-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. glycine-N-acyltransferase (3-methylcrotonoylglycine)

  Catalysed by AGXT2, GLYATmitochondrial matrix

• isovaleryl-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. glycine N-acyltransferase (isovalerylglycine)

  Catalysed by AGXT2, GLYAT, GLYATL2, GLYATL1mitochondrial matrixOne of 3 routes

• arachidonoyl-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. Arachidonate:CoA ligase (AMP-forming)

  Catalysed by AGXT2, SLC27A2, ACSL4, ACSL3 and 5 moremitochondrial matrix, cytosolOne of 11 routes

• CHEBI:15519Reach 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 C-acyltransferase

  Catalysed by AGXT2, ACAA1, SCP2, MYO5Bmitochondrial matrix, peroxisomeOne of 2 routes

• palmitoyl-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. Palmitate:CoA ligase (AMP-forming)

  Catalysed by AGXT2, SLC27A2, ACSL4, ACSL3 and 5 moremitochondrial matrix, cytosolOne of 11 routes

• oleoyl-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. Transport of octadecenoyl-CoA into Mitochondrial Matrix

  Catalysed by AGXT2, CPT1A, CPT1C, CPT1Bmitochondrial matrix, cytosolOne of 11 routes

• phenylacetyl-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. Phenylacetate:CoA ligase

  Catalysed by AGXT2mitochondrial matrix, cytosolOne of 4 routes

• propionyl-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. Propanoate:CoA ligase (AMP-forming)

  Catalysed by AGXT2, ACSS3, ACSS2, ACSS1mitochondrial matrix, cytosolOne of 43 routes

• (S)-malateReach 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)-malate + NAD(+) = pyruvate + CO2 + NADH

  Catalysed by AGXT2, ME2One of 4 routes

• (6R)-5,10-methylene-5,6,7,8-tetrahydrofolateReach 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. (6R)-5,10-methylene-5,6,7,8-tetrahydrofolate + glycine + H2O = (6S)-5,6,7,8-tetrahydrofolate + L-serine

  Catalysed by AGXT2, SHMT1, SHMT2One of 2 routes

• 10-formyltetrahydrofolic acidReach from here →
  1. N(omega)-methyl-L-arginine + glyoxylate = 5-(3-methylguanidino)-2-oxopentanoate + glycine
  2. 5,10-Methylenetetrahydrofolate:glycine hydroxymethyltransferase
  3. Formate:tetrahydrofolate ligase (ADP-forming)

  Catalysed by AGXT2, SHMT1, MTHFD1cytosolOne of 3 routes

• 5-methyltetrahydrofolic acidReach from here →
  1. N(omega)-methyl-L-arginine + glyoxylate = 5-(3-methylguanidino)-2-oxopentanoate + glycine
  2. 5,10-Methylenetetrahydrofolate:glycine hydroxymethyltransferase
  3. histamine N-methyltransferase (SAM)

  Catalysed by AGXT2, SHMT1, HNMTcytosol

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

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

• CHEBI:15650Reach 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-acetyl-LTE4 to leukotriene E4 conversion

  Catalysed by AGXT2, ZDHHC11B, NAA10, ESCO2 and 29 moremitochondrial matrix, cytosolOne of 6 routes

• trimethylenediamineReach from here →
  1. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  2. transport of citrulline and lysine (cytosol to extracellular)
  3. deoxyhypusine synthase (1,3-diaminopropane)

  Catalysed by DDAH1, SLC7A5, SLC7A6, DHPSextracellular space, cytosol

• CHEBI:15727Reach from here →
  1. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  2. transport of citrulline and histidine (cytosol to extracellular)
  3. L-histidine:beta-alanine ligase (ADP-forming)

  Catalysed by DDAH1, SLC7A5, SLC7A6, CARNS1extracellular space, cytosolOne of 3 routes

• formateReach from here →
  1. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine
  2. methylamine:oxygen oxidoreductase (deaminating) (copper-containing)
  3. formaldehyde + NAD(+) + H2O = formate + NADH + 2 H(+)

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

• CHEBI:15746Reach 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. diamine N-acetyltransferase (N1-acetylspermine)

  Catalysed by AGXT2, SAT1, SAT2mitochondrial matrix, cytosolOne of 2 routes