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

Three steps

• CHEBI:28701Reach 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. 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),N(omega)-dimethyl-L-arginine(in) + L-arginine(out) = N(omega),N(omega)-dimethyl-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 SLC25A2, SLC7A9, CTHinner side of the membrane, outer side of the membrane, cytosol

• N-acetyl-L-cysteineReach from here →
  1. Nomega,Nomega'-dimethyl-L-arginine dimethylamidohydrolase
  2. transport of citrulline and cysteine (cytosol to extracellular)
  3. N-acetylglutamate synthase (N-acetyl-L-cysteine)

  Catalysed by DDAH1, SLC7A6, NAGScytosol, extracellular space, mitochondrial matrix

• a dicarboxylateReach from here →
  1. N(omega),N(omega)-dimethyl-L-arginine + glyoxylate = 5-(3,3-dimethylguanidino)-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 4 routes

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

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

• Ca(2+)Reach 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 Ca2+ and K+ (cytosol to extracellular)

  Catalysed by AGXT2, SLC1A7, SLC1A3, SLC1A2 and 7 moreextracellular space, cytosolOne of 3 routes

• Cys-tRNA(Cys)Reach from here →
  1. Nomega,Nomega'-dimethyl-L-arginine dimethylamidohydrolase
  2. transport of citrulline and cysteine (cytosol to extracellular)
  3. L-Cysteine:tRNA(Cys) ligase (AMP-forming)

  Catalysed by DDAH1, SLC7A6, CARS1cytosol, extracellular space

• Phe-tRNA(Phe)Reach from here →
  1. Nomega,Nomega'-dimethyl-L-arginine dimethylamidohydrolase
  2. transport of citrulline and phenylalanine (cytosol to extracellular)
  3. L-Phenylalanine:tRNA(Ala) ligase (AMP-forming)

  Catalysed by DDAH1, SLC7A6, FARSB, FARSAcytosol, extracellular space

• Trp-tRNA(Trp)Reach from here →
  1. Nomega,Nomega'-dimethyl-L-arginine dimethylamidohydrolase
  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 morecytosol, extracellular space

• Ile-tRNA(Ile)Reach from here →
  1. Nomega,Nomega'-dimethyl-L-arginine dimethylamidohydrolase
  2. transport of citrulline and isoleucine (cytosol to extracellular)
  3. L-Isoleucine:tRNA(Ile) ligase (AMP-forming)

  Catalysed by DDAH1, SLC7A6, IARS1cytosol, extracellular space

• Gln-tRNA(Gln)Reach from here →
  1. Nomega,Nomega'-dimethyl-L-arginine dimethylamidohydrolase
  2. transport of citrulline and glutamine (cytosol to extracellular)
  3. L-Glutamine:tRNA(Gln) ligase (AMP-forming)

  Catalysed by DDAH1, SLC7A6, QARS1cytosol, extracellular space

• Asn-tRNA(Asn)Reach from here →
  1. Nomega,Nomega'-dimethyl-L-arginine dimethylamidohydrolase
  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 morecytosol, extracellular space

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

  Catalysed by AGXT2, MOCOS, SCLY

• cholateReach 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. solute carrier organic anion transporter (cholate)

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

• glycolateReach 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 + glyoxylate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + glycine
  3. glycolate + NADP(+) = glyoxylate + NADPH + H(+)

  Catalysed by AGXT2, GRHPROne of 3 routes

• hydrogen sulfideReach from here →
  1. Nomega,Nomega'-dimethyl-L-arginine dimethylamidohydrolase
  2. transport of citrulline and cysteine (cytosol to extracellular)
  3. L-cysteine hydrogen-sulfide-lyase (deaminating

  Catalysed by DDAH1, SLC7A6, CTHcytosol, extracellular spaceOne of 3 routes

• D-aspartateReach from here →
  1. N(omega),N(omega)-dimethyl-L-arginine + oxaloacetate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + L-aspartate
  2. K(+)(in) + L-aspartate(out) + 3 Na(+)(out) + H(+)(out) = K(+)(out) + L-aspartate(in) + 3 Na(+)(in) + H(+)(in)
  3. D-aspartate(out) + K(+)(in) + 3 Na(+)(out) + H(+)(out) = D-aspartate(in) + K(+)(out) + 3 Na(+)(in) + H(+)(in)

  Catalysed by AGXT2, SLC1A7, SLC1A3, SLC1A2 and 2 moreinner side of the membrane, outer side of the membraneOne of 4 routes

• acetateReach from here →
  1. N(omega),N(omega)-dimethyl-L-arginine(in) + L-ornithine(out) = N(omega),N(omega)-dimethyl-L-arginine(out) + L-ornithine(in)
  2. N2-Acetyl-L-ornithine amidohydrolase
  3. N2-Acetyl-L-ornithine amidohydrolase

  Catalysed by SLC25A2, ACY1inner side of the membrane, outer side of the membrane, cytosolOne of 5 routes

• CHEBI:30249Reach from here →
  1. Nomega,Nomega'-dimethyl-L-arginine dimethylamidohydrolase
  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 morecytosol, extracellular space

• 3-acetamidopropanalReach 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 by Y+Lat-2 into Extracellular Space
  3. N1-acetylspermidine:oxygen oxidoreductase (3-acetamidopropanal-forming)

  Catalysed by SLC25A2, 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),N(omega)-dimethyl-L-arginine + pyruvate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + L-alanine
  2. N(omega),N(omega)-dimethyl-L-arginine + glyoxylate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + glycine
  3. glyoxylate + O2 + H2O = oxalate + H2O2 + H(+)

  Catalysed by AGXT2, HAO1One of 3 routes

• formic 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 formate (cytosol to extracellular)

  Catalysed by SLC25A2, SLC6A14, SLC26A4inner side of the membrane, outer side of the membrane, extracellular space, cytosolOne of 4 routes

• anthranilic acidReach from here →
  1. N(omega),N(omega)-dimethyl-L-arginine + pyruvate = 5-(3,3-dimethylguanidino)-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),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 propanoate and pyruvate (cytosol to extracellular)

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

• citric 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 + oxaloacetate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + L-aspartate
  3. acetyl-CoA:oxaloacetate C-acetyltransferase (thioester-hydrolysing)

  Catalysed by AGXT2, CSmitochondrial matrixOne of 2 routes

• butyric 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 butyrate and pyruvate (cytosol to extracellular)

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

• maleateReach 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. maleate(in) + sulfate(out) = maleate(out) + sulfate(in)

  Catalysed by AGXT2, SLC25A14, SLC25A30inner side of the membrane, outer side of the membraneOne of 2 routes

• malonic 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. Malonate Transport, Antiport with Chloride

  Catalysed by SLC25A2, SLC6A14inner side of the membrane, outer side of the membrane, extracellular space, cytosolOne of 4 routes

• (9Z)-octadecenoateReach from here →
  1. N(omega),N(omega)-dimethyl-L-arginine + glyoxylate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + glycine
  2. (9Z)-octadecenoyl-CoA + glycine = N-(9Z-octadecenoyl)glycine + CoA + H(+)
  3. (9Z)-octadecenoate + glycine = N-(9Z-octadecenoyl)glycine + H2O

  Catalysed by AGXT2, GLYATL3, GLYATL2, FAAH and 1 more

• 3-hydroxypyruvic 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. L-Serine:pyruvate aminotransferase

  Catalysed by AGXT2, AGXTcytosolOne of 2 routes

• (S)-dihydroorotateReach from here →
  1. N(omega),N(omega)-dimethyl-L-arginine + oxaloacetate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + L-aspartate
  2. carbamoyl-phosphate:L-aspartate carbamoyltransferase
  3. (S)-dihydroorotate amidohydrolase

  Catalysed by AGXT2, CADcytosolOne of 2 routes

• an alcoholReach 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. a hydroperoxide + 2 glutathione = an alcohol + glutathione disulfide + H2O

  Catalysed by AGXT2, GSS, CP, PRDX6

• glutarateReach from here →
  1. N(omega),N(omega)-dimethyl-L-arginine + glyoxylate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + glycine
  2. bile acid-CoA: amino acid N-acyltransferase
  3. glycocholate(out) + glutarate(in) = glycocholate(in) + glutarate(out)

  Catalysed by AGXT2, BAAT, SLC22A24peroxisome, inner side of the membrane, outer side of the membraneOne of 2 routes

• 4-hydroxy-2-oxoglutaric 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 + oxaloacetate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + L-aspartate
  3. D-aspartate:2-oxoglutarate aminotransferase

  Catalysed by AGXT2, GOT2mitochondrial matrix

• (2R,3R)-tartrateReach 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. (2R,3R)-tartrate(in) + sulfate(out) = (2R,3R)-tartrate(out) + sulfate(in)

  Catalysed by AGXT2, SLC25A14, SLC25A30inner side of the membrane, outer side of the membraneOne of 2 routes

• (S,S)-tartrateReach 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. (S,S)-tartrate(in) + sulfate(out) = (S,S)-tartrate(out) + sulfate(in)

  Catalysed by AGXT2, SLC25A14, SLC25A30inner side of the membrane, outer side of the membraneOne of 2 routes

• (3R)-citramalateReach 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. (3R)-citramalate(in) + sulfate(out) = (3R)-citramalate(out) + sulfate(in)

  Catalysed by AGXT2, SLC25A14, SLC25A30inner side of the membrane, outer side of the membraneOne of 2 routes

• (3S)-citramalateReach 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. (3S)-citramalate(in) + sulfate(out) = (3S)-citramalate(out) + sulfate(in)

  Catalysed by AGXT2, SLC25A14, SLC25A30inner side of the membrane, outer side of the membraneOne of 2 routes

• (5Z,8Z,11Z,14Z)-eicosatetraenoateReach 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 arachidonate and GSH (cytosol to extracellular)

  Catalysed by AGXT2, GSScytosol, extracellular spaceOne of 3 routes

• 3-oxopropanoateReach 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-oxopropanoate + L-alanine = beta-alanine + pyruvate

  Catalysed by AGXT2One of 2 routes

• thiosulfateReach 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. thiosulfate(in) + sulfate(out) = thiosulfate(out) + sulfate(in)

  Catalysed by AGXT2, SLC25A14, SLC25A30, SLC26A1 and 1 moreinner side of the membrane, outer side of the membraneOne of 2 routes

• 4-methylthio-2-oxobutanoic acidReach from here →
  1. Nomega,Nomega'-dimethyl-L-arginine dimethylamidohydrolase
  2. transport of citrulline and methionine (cytosol to extracellular)
  3. L-Methionine:oxygen oxidoreductase (deaminating)

  Catalysed by DDAH1, SLC7A6, IL4I1cytosol, extracellular space

• di-mu-sulfido-diiron(2+)Reach from here →
  1. Nomega,Nomega'-dimethyl-L-arginine dimethylamidohydrolase
  2. transport of citrulline and cysteine (cytosol to extracellular)
  3. De novo synthesis of 2Fe2S

  Catalysed by DDAH1, SLC7A6, NDUFAB1, FDXR and 5 morecytosol, extracellular space, mitochondrial matrix

• serotoninReach 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 serotonin (cytosol to extracellular)

  Catalysed by AGXT2, GSS, SLCO1A2, SLCO1B3cytosol, extracellular spaceOne of 4 routes

• (S)-3-methyl-2-oxopentanoateReach from here →
  1. Nomega,Nomega'-dimethyl-L-arginine dimethylamidohydrolase
  2. transport of citrulline and isoleucine (cytosol to extracellular)
  3. L-isoleucine + 2-oxoglutarate = (S)-3-methyl-2-oxopentanoate + L-glutamate

  Catalysed by DDAH1, SLC7A6, BCAT2, BCAT1cytosol, extracellular space

• L-alpha-aminobutyric 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 + 2-oxobutanoate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + (2S)-2-aminobutanoate
  3. glutamic-pyruvic transaminase ((S)-2-aminobutanoate)

  Catalysed by AGXT2, GPTcytosol

• 3-methyl-2-oxovaleric acidReach from here →
  1. Nomega,Nomega'-dimethyl-L-arginine dimethylamidohydrolase
  2. transport of citrulline and isoleucine (cytosol to extracellular)
  3. L-Leucine:2-oxoglutarate aminotransferase

  Catalysed by DDAH1, SLC7A6, BCAT1cytosol, extracellular spaceOne of 2 routes

• 3-(4-hydroxyphenyl)pyruvateReach from here →
  1. Nomega,Nomega'-dimethyl-L-arginine dimethylamidohydrolase
  2. transport of citrulline and tyrosine (cytosol to extracellular)
  3. L-tyrosine:2-oxoglutarate aminotransferase

  Catalysed by DDAH1, SLC7A6, GOT2, GOT1 and 1 morecytosol, extracellular spaceOne of 7 routes

• taurocholateReach 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. solute carrier organic anion transporter (GSH)

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

• 3-hydroxyanthranilateReach from here →
  1. N(omega),N(omega)-dimethyl-L-arginine + pyruvate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + L-alanine
  2. 3-hydroxy-L-kynurenine + H2O = 3-hydroxyanthranilate + L-alanine + H(+)
  3. 3-hydroxy-L-kynurenine + H2O = 3-hydroxyanthranilate + L-alanine + H(+)

  Catalysed by AGXT2, KYNU