N(omega),N(omega)-dimethyl-L-arginine

Three steps

• quinolinic acidReach from here →
  1. N(omega),N(omega)-dimethyl-L-arginine + oxaloacetate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + L-aspartate
  2. L-aspartate(in) + sulfate(out) = L-aspartate(out) + sulfate(in)
  3. Transport of Quinolinic Acid

  Catalysed by AGXT2, SLC25A14, SLC25A30, SLC22A6inner side of the membrane, outer side of the membrane, extracellular space, cytosolOne of 2 routes

• 3'-deoxy-3',4'-didehydro-CTPReach from here →
  1. N(omega),N(omega)-dimethyl-L-arginine + pyruvate = 5-(3,3-dimethylguanidino)-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),N(omega)-dimethyl-L-arginine(in) + L-arginine(out) = N(omega),N(omega)-dimethyl-L-arginine(out) + L-arginine(in)
  2. L-Arginine amidinohydrolase
  3. urea = cyanamide + H2O

  Catalysed by SLC25A2, ARG1, CA1, CA2inner side of the membrane, outer side of the membrane, cytosol

• pyridoxineReach from here →
  1. N(omega),N(omega)-dimethyl-L-arginine + pyruvate = 5-(3,3-dimethylguanidino)-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. Nomega,Nomega'-dimethyl-L-arginine dimethylamidohydrolase
  2. transport of citrulline and methionine (cytosol to extracellular)
  3. glyoxylate + L-methionine = 4-methylsulfanyl-2-oxobutanoate + glycine

  Catalysed by DDAH1, SLC7A6, AADATcytosol, extracellular spaceOne of 2 routes

• N-[(S)-lactoyl]-L-phenylalanineReach from here →
  1. Nomega,Nomega'-dimethyl-L-arginine dimethylamidohydrolase
  2. transport of citrulline and phenylalanine (cytosol to extracellular)
  3. (S)-lactate + L-phenylalanine = N-[(S)-lactoyl]-L-phenylalanine + H2O

  Catalysed by DDAH1, SLC7A6, CNDP2cytosol, extracellular space

• tryptamineReach from here →
  1. Nomega,Nomega'-dimethyl-L-arginine dimethylamidohydrolase
  2. transport of citrulline and tryptophan (cytosol to extracellular)
  3. L-tryptophan decarboxy-lyase

  Catalysed by DDAH1, SLC7A9, SLC3A1, SLC7A6 and 1 morecytosol, extracellular space

• 2-oxoglutaramateReach from here →
  1. Nomega,Nomega'-dimethyl-L-arginine dimethylamidohydrolase
  2. transport of citrulline and glutamine (cytosol to extracellular)
  3. L-Glutamine:pyruvate aminotransferase

  Catalysed by DDAH1, SLC7A6, KYAT1cytosol, extracellular spaceOne of 5 routes

• (S)-2-hydroxyglutarateReach from here →
  1. N(omega),N(omega)-dimethyl-L-arginine + pyruvate = 5-(3,3-dimethylguanidino)-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

• formaldehydeReach from here →
  1. N(omega),N(omega)-dimethyl-L-arginine + glyoxylate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + glycine
  2. S-Adenosyl-L-methionine:glycine N-methyltransferase
  3. sarcosine:oxygen oxidoreductase (demethylating)

  Catalysed by AGXT2, GNMT, PIPOX, SARDHcytosol, peroxisomeOne of 2 routes

• 3-fumarylpyruvateReach from here →
  1. N(omega),N(omega)-dimethyl-L-arginine + pyruvate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + L-alanine
  2. N(omega),N(omega)-dimethyl-L-arginine + pyruvate = 5-(3,3-dimethylguanidino)-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),N(omega)-dimethyl-L-arginine + pyruvate = 5-(3,3-dimethylguanidino)-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),N(omega)-dimethyl-L-arginine(in) + L-arginine(out) = N(omega),N(omega)-dimethyl-L-arginine(out) + L-arginine(in)
  2. L-Arginine:glycine amidinotransferase
  3. S-Adenosyl-L-methionine:guanidinoacetate N-methyltransferase

  Catalysed by SLC25A2, GATM, GAMTinner side of the membrane, outer side of the membrane, cytosolOne of 2 routes

• bilirubin IXalphaReach from here →
  1. N(omega),N(omega)-dimethyl-L-arginine + glyoxylate = 5-(3,3-dimethylguanidino)-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),N(omega)-dimethyl-L-arginine(in) + L-arginine(out) = N(omega),N(omega)-dimethyl-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 SLC25A2, SLC6A14, SLC26A6inner side of the membrane, outer side of the membrane, extracellular space, cytosolOne of 4 routes

• (R)-3-hydroxybutyric acidReach from here →
  1. N(omega),N(omega)-dimethyl-L-arginine + pyruvate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + L-alanine
  2. N(omega),N(omega)-dimethyl-L-arginine + pyruvate = 5-(3,3-dimethylguanidino)-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),N(omega)-dimethyl-L-arginine + glyoxylate = 5-(3,3-dimethylguanidino)-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),N(omega)-dimethyl-L-arginine + pyruvate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + L-alanine
  2. N(omega),N(omega)-dimethyl-L-arginine + pyruvate = 5-(3,3-dimethylguanidino)-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),N(omega)-dimethyl-L-arginine + glyoxylate = 5-(3,3-dimethylguanidino)-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),N(omega)-dimethyl-L-arginine + glyoxylate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + glycine
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. Formation of Homocystine

  Catalysed by AGXT2, GSScytosol

• anilineReach from here →
  1. N(omega),N(omega)-dimethyl-L-arginine + pyruvate = 5-(3,3-dimethylguanidino)-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),N(omega)-dimethyl-L-arginine + pyruvate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + L-alanine
  2. N(omega),N(omega)-dimethyl-L-arginine + pyruvate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + L-alanine
  3. aceneuramate = aldehydo-N-acetyl-D-mannosamine + pyruvate

  Catalysed by AGXT2, NPL

• CHEBI:17312Reach from here →
  1. N(omega),N(omega)-dimethyl-L-arginine + pyruvate = 5-(3,3-dimethylguanidino)-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),N(omega)-dimethyl-L-arginine + pyruvate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + L-alanine
  2. N(omega),N(omega)-dimethyl-L-arginine + pyruvate = 5-(3,3-dimethylguanidino)-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),N(omega)-dimethyl-L-arginine + glyoxylate = 5-(3,3-dimethylguanidino)-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 4 routes

• D-aspartic acidReach from here →
  1. N(omega),N(omega)-dimethyl-L-arginine + oxaloacetate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + L-aspartate
  2. transport of aspartate (cytosol to extracellular)
  3. transport of D-aspartate (cytosol to extracellular)

  Catalysed by AGXT2, SLC1A7, SLC1A3, SLC1A2 and 2 moreextracellular space, cytosol

• CHEBI:17380Reach from here →
  1. Nomega,Nomega'-dimethyl-L-arginine dimethylamidohydrolase
  2. transport of citrulline and tryptophan (cytosol to extracellular)
  3. Transport of 3-Hydroxy-L-Kynurenine

  Catalysed by DDAH1, SLC7A9, SLC3A1, SLC7A6 and 1 morecytosol, extracellular spaceOne of 3 routes

• (S)-1-pyrroline-5-carboxylateReach from here →
  1. Nomega,Nomega'-dimethyl-L-arginine dimethylamidohydrolase
  2. transport of citrulline and proline (cytosol to extracellular)
  3. L-proline:(acceptor) oxidoreductase

  Catalysed by DDAH1, SLC7A6, PRODH2cytosol, extracellular spaceOne of 5 routes

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

  Catalysed by SLC25A2, SLC3A2, SLC7A7, SRMinner side of the membrane, outer side of the membrane, extracellular space, cytosolOne of 2 routes

• nitrateReach from here →
  1. N(omega),N(omega)-dimethyl-L-arginine(in) + L-arginine(out) = N(omega),N(omega)-dimethyl-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 SLC25A2, NOS3, NOS1, NOS2 and 1 moreinner side of the membrane, outer side of the membrane, cytosol

• indole-3-pyruvateReach from here →
  1. Nomega,Nomega'-dimethyl-L-arginine dimethylamidohydrolase
  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 morecytosol, extracellular spaceOne of 3 routes

• 3,3',5'-triiodo-L-thyronine sulfateReach from here →
  1. N(omega),N(omega)-dimethyl-L-arginine + pyruvate = 5-(3,3-dimethylguanidino)-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),N(omega)-dimethyl-L-arginine + pyruvate = 5-(3,3-dimethylguanidino)-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),N(omega)-dimethyl-L-arginine + pyruvate = 5-(3,3-dimethylguanidino)-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 4 routes

• (7Z,10Z,13Z)-hexadecatrienoyl-CoAReach from here →
  1. N(omega),N(omega)-dimethyl-L-arginine + pyruvate = 5-(3,3-dimethylguanidino)-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),N(omega)-dimethyl-L-arginine + glyoxylate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + glycine
  2. S-Adenosyl-L-methionine:glycine N-methyltransferase
  3. dimethylglycine dehydrogenase (formaldehyde)

  Catalysed by AGXT2, GNMT, PDPR, DMGDHcytosol

• glycine betaineReach from here →
  1. N(omega),N(omega)-dimethyl-L-arginine(in) + L-arginine(out) = N(omega),N(omega)-dimethyl-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 SLC25A2, SLC6A14, SLC6A12inner side of the membrane, outer side of the membrane, extracellular space, cytosolOne of 3 routes

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

  Catalysed by SLC25A2, 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. Nomega,Nomega'-dimethyl-L-arginine dimethylamidohydrolase
  2. transport of citrulline and histidine (cytosol to extracellular)
  3. L-histidine ammonia-lyase (urocanate-forming)

  Catalysed by DDAH1, SLC7A5, SLC7A6, HALcytosol, extracellular spaceOne of 2 routes

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

  Catalysed by SLC25A2, ARG1, MPOinner side of the membrane, outer side of the membrane, cytosol, nucleusOne of 4 routes

• 5-hydroxy-L-tryptophanReach from here →
  1. Nomega,Nomega'-dimethyl-L-arginine dimethylamidohydrolase
  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 morecytosol, extracellular space

• methylarsonous acidReach from here →
  1. N(omega),N(omega)-dimethyl-L-arginine + glyoxylate = 5-(3,3-dimethylguanidino)-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. Nomega,Nomega'-dimethyl-L-arginine dimethylamidohydrolase
  2. transport of citrulline and leucine (cytosol to extracellular)
  3. L-Leucine:2-oxoglutarate aminotransferase

  Catalysed by DDAH1, BCAT2cytosol, extracellular space, mitochondrial matrixOne of 5 routes

• 3-oxopropanoic acidReach from here →
  1. N(omega),N(omega)-dimethyl-L-arginine + pyruvate = 5-(3,3-dimethylguanidino)-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. Nomega,Nomega'-dimethyl-L-arginine dimethylamidohydrolase
  2. transport of citrulline and phenylalanine (cytosol to extracellular)
  3. Phenylalanine Transaminase, Mitochondrial

  Catalysed by DDAH1, SLC7A6, GOT2, TATcytosol, extracellular space, mitochondrial matrixOne of 6 routes

• fumaric acidReach from here →
  1. Nomega,Nomega'-dimethyl-L-arginine dimethylamidohydrolase
  2. L-Citrulline:L-aspartate ligase (AMP-forming)
  3. 2-(Nomega-L-arginino)succinate arginine-lyase (fumarate-forming)

  Catalysed by DDAH1, ASS1, ASLcytosolOne of 8 routes

• dTDPReach from here →
  1. N(omega),N(omega)-dimethyl-L-arginine + pyruvate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + L-alanine
  2. N(omega),N(omega)-dimethyl-L-arginine + pyruvate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + L-alanine
  3. pyruvate kinase (dTDP)

  Catalysed by AGXT2, PKM, PKLRcytosol

• CHEBI:18183Reach from here →
  1. N(omega),N(omega)-dimethyl-L-arginine(in) + L-lysine(out) = N(omega),N(omega)-dimethyl-L-arginine(out) + L-lysine(in)
  2. epsilon-(gamma-L-glutamyl)-L-lysine = 5-oxo-L-proline + L-lysine
  3. epsilon-(gamma-L-Glutamyl)-L-lysine[c] = 5-oxoproline[c] + lysine[c]

  Catalysed by SLC25A2, GGACTinner side of the membrane, outer side of the membrane, cytosolOne of 3 routes

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

  Catalysed by SLC25A2, 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),N(omega)-dimethyl-L-arginine + glyoxylate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + glycine
  2. 5-Phospho-D-ribosylamine:glycine ligase (ADP-forming)
  3. 10-formyltetrahydrofolate:5'-phosphoribosylglycinamide formyltransferase

  Catalysed by AGXT2, GARTcytosol