N(5)-[(Z)-amino(hydroxyimino)methyl]ornithine

Three steps

• L-tyrosineReach from here →
  1. N-(omega)-Hydroxyarginine,NADPH:oxygen oxidoreductase (nitric-oxide-forming)
  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 NOS3, NOS1, NOS2, SLC7A6 and 1 morecytosol, extracellular spaceOne of 2 routes

• N(1)-acetylspermidineReach from here →
  1. L-arginine,NADPH:oxygen oxidoreductase (N-(omega)-hydroxyarginine-forming)
  2. Putrescine Export via Putrescine/Arginine Antiporter
  3. N(1)-acetylspermidine + O2 + H2O = 3-acetamidopropanal + putrescine + H2O2

  Catalysed by NOS3, NOS1, NOS2, SLC3A2 and 2 morecytosol, extracellular space

• trans-4-hydroxy-L-prolineReach from here →
  1. N-(omega)-Hydroxyarginine,NADPH:oxygen oxidoreductase (nitric-oxide-forming)
  2. transport of alanine and citrulline (cytosol to extracellular)
  3. trans-4-hydroxy-L-proline(out) + L-alanine(in) + Na(+)(out) = trans-4-hydroxy-L-proline(in) + L-alanine(out) + Na(+)(in)

  Catalysed by NOS3, NOS1, NOS2, SLC7A6 and 1 morecytosol, extracellular space, inner side of the membrane, outer side of the membraneOne of 2 routes

• histamineReach from here →
  1. N-(omega)-Hydroxyarginine,NADPH:oxygen oxidoreductase (nitric-oxide-forming)
  2. transport of citrulline and histidine (cytosol to extracellular)
  3. L-histidine carboxy-lyase (histamine-forming)

  Catalysed by NOS3, NOS1, NOS2, SLC7A5 and 2 morecytosol, extracellular spaceOne of 2 routes

• L-2-aminopentanoateReach from here →
  1. L-arginine,NADPH:oxygen oxidoreductase (N-(omega)-hydroxyarginine-forming)
  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 NOS3, NOS1, NOS2, SLC25A2 and 1 morecytosol, inner side of the membrane, outer side of the membrane

• L-2-aminohexanoateReach from here →
  1. L-arginine,NADPH:oxygen oxidoreductase (N-(omega)-hydroxyarginine-forming)
  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 NOS3, NOS1, NOS2, SLC25A2 and 1 morecytosol, inner side of the membrane, outer side of the membrane

• S-sulfanyl-L-cysteineReach from here →
  1. N-(omega)-Hydroxyarginine,NADPH:oxygen oxidoreductase (nitric-oxide-forming)
  2. transport of citrulline and cysteine (cytosol to extracellular)
  3. 2 L-cysteine = S-sulfanyl-L-cysteine + L-alanine

  Catalysed by NOS3, NOS1, NOS2, SLC7A6 and 1 morecytosol, extracellular space

• N-formyl-L-kynurenineReach from here →
  1. N-(omega)-Hydroxyarginine,NADPH:oxygen oxidoreductase (nitric-oxide-forming)
  2. transport of citrulline and tryptophan (cytosol to extracellular)
  3. L-tryptophan + O2 = N-formyl-L-kynurenine

  Catalysed by NOS3, NOS1, NOS2, SLC7A9 and 5 morecytosol, extracellular space

• 5-phospho-beta-D-ribosylamineReach from here →
  1. N-(omega)-Hydroxyarginine,NADPH:oxygen oxidoreductase (nitric-oxide-forming)
  2. transport of citrulline and glutamine (cytosol to extracellular)
  3. phosphoribosyl pyrophosphate amidotransferase (glutamine)

  Catalysed by NOS3, NOS1, NOS2, SLC7A6 and 1 morecytosol, extracellular spaceOne of 2 routes

• D-glucosamine 6-phosphateReach from here →
  1. N-(omega)-Hydroxyarginine,NADPH:oxygen oxidoreductase (nitric-oxide-forming)
  2. transport of citrulline and glutamine (cytosol to extracellular)
  3. D-fructose 6-phosphate + L-glutamine = D-glucosamine 6-phosphate + L-glutamate

  Catalysed by NOS3, NOS1, NOS2, SLC7A6 and 2 morecytosol, extracellular space

• L-methionine (S)-S-oxideReach from here →
  1. N-(omega)-Hydroxyarginine,NADPH:oxygen oxidoreductase (nitric-oxide-forming)
  2. transport of citrulline and methionine (cytosol to extracellular)
  3. [thioredoxin]-disulfide + L-methionine + H2O = L-methionine (S)-S-oxide + [thioredoxin]-dithiol

  Catalysed by NOS3, NOS1, NOS2, SLC7A6 and 1 morecytosol, extracellular space

• L-methionine (R)-S-oxideReach from here →
  1. N-(omega)-Hydroxyarginine,NADPH:oxygen oxidoreductase (nitric-oxide-forming)
  2. transport of citrulline and methionine (cytosol to extracellular)
  3. [thioredoxin]-disulfide + L-methionine + H2O = L-methionine (R)-S-oxide + [thioredoxin]-dithiol

  Catalysed by NOS3, NOS1, NOS2, SLC7A6 and 3 morecytosol, extracellular space

• 5-amino-2-oxopentanoateReach from here →
  1. N-(omega)-Hydroxyarginine,NADPH:oxygen oxidoreductase (nitric-oxide-forming)
  2. Amino Acid-Polyamine-Organocation (Apc) Tcdb:2.A.3.8.15
  3. L-ornithine + pyruvate = 5-amino-2-oxopentanoate + L-alanine

  Catalysed by NOS3, NOS1, NOS2, SLC7A9 and 1 morecytosol, extracellular spaceOne of 2 routes

• N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycineReach from here →
  1. N-(omega)-Hydroxyarginine,NADPH:oxygen oxidoreductase (nitric-oxide-forming)
  2. transport of citrulline and glycine (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + glycine = N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycine + CoA + H(+)

  Catalysed by NOS3, NOS1, NOS2, SLC7A9 and 3 morecytosol, extracellular spaceOne of 2 routes

• methylamineReach from here →
  1. L-arginine,NADPH:oxygen oxidoreductase (N-(omega)-hydroxyarginine-forming)
  2. N(omega)-methyl-L-arginine(in) + L-arginine(out) = N(omega)-methyl-L-arginine(out) + L-arginine(in)
  3. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine

  Catalysed by NOS3, NOS1, NOS2, SLC25A29 and 1 morecytosol, inner side of the membrane, outer side of the membrane

• N-[(R)-4-phosphopantothenoyl]-L-cysteineReach from here →
  1. N-(omega)-Hydroxyarginine,NADPH:oxygen oxidoreductase (nitric-oxide-forming)
  2. transport of citrulline and cysteine (cytosol to extracellular)
  3. (R)-4'-phosphopantothenate:L-cysteine ligase

  Catalysed by NOS3, NOS1, NOS2, SLC7A6 and 1 morecytosol, extracellular spaceOne of 4 routes

• 4-aminobutanoateReach from here →
  1. L-arginine,NADPH:oxygen oxidoreductase (N-(omega)-hydroxyarginine-forming)
  2. transport of arginine and chloride (cytosol to extracellular)
  3. transport of 4-aminobutyrate and chloride (cytosol to extracellular)

  Catalysed by NOS3, NOS1, NOS2, SLC6A14 and 1 morecytosol, extracellular spaceOne of 5 routes

• 3-iodo-L-tyrosineReach from here →
  1. N-(omega)-Hydroxyarginine,NADPH:oxygen oxidoreductase (nitric-oxide-forming)
  2. transport of citrulline and tyrosine (cytosol to extracellular)
  3. thyroid peroxidase (iodine)

  Catalysed by NOS3, NOS1, NOS2, SLC7A6 and 1 morecytosol, extracellular spaceOne of 2 routes

• L-prolineReach from here →
  1. N-(omega)-Hydroxyarginine,NADPH:oxygen oxidoreductase (nitric-oxide-forming)
  2. transport of alanine and citrulline (cytosol to extracellular)
  3. L-proline(out) + L-alanine(in) + Na(+)(out) = L-proline(in) + L-alanine(out) + Na(+)(in)

  Catalysed by NOS3, NOS1, NOS2, SLC7A6 and 1 morecytosol, extracellular space, inner side of the membrane, outer side of the membraneOne of 2 routes

• N-benzoylglycineReach from here →
  1. N-(omega)-Hydroxyarginine,NADPH:oxygen oxidoreductase (nitric-oxide-forming)
  2. transport of citrulline and glycine (cytosol to extracellular)
  3. Hippurate (Benzoylglycinate) Formation

  Catalysed by NOS3, NOS1, NOS2, SLC7A9 and 2 morecytosol, extracellular space, mitochondrial matrixOne of 2 routes

• 3-sulfino-L-alanineReach from here →
  1. N-(omega)-Hydroxyarginine,NADPH:oxygen oxidoreductase (nitric-oxide-forming)
  2. transport of citrulline and cysteine (cytosol to extracellular)
  3. L-Cysteine:oxygen oxidoreductase

  Catalysed by NOS3, NOS1, NOS2, SLC7A6 and 1 morecytosol, extracellular spaceOne of 2 routes

• L-cysteinylglycineReach from here →
  1. N-(omega)-Hydroxyarginine,NADPH:oxygen oxidoreductase (nitric-oxide-forming)
  2. transport of alanine and citrulline (cytosol to extracellular)
  3. gamma-glutamyltransferase (alanine)

  Catalysed by NOS3, NOS1, NOS2, SLC7A6 and 6 morecytosol, extracellular spaceOne of 2 routes

• Mo-molybdopterinReach from here →
  1. N-(omega)-Hydroxyarginine,NADPH:oxygen oxidoreductase (nitric-oxide-forming)
  2. transport of alanine and citrulline (cytosol to extracellular)
  3. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O

  Catalysed by NOS3, NOS1, NOS2, SLC7A6 and 1 morecytosol, extracellular space

• (2S)-2-aminobutanoateReach from here →
  1. N-(omega)-Hydroxyarginine,NADPH:oxygen oxidoreductase (nitric-oxide-forming)
  2. transport of alanine and citrulline (cytosol to extracellular)
  3. 2-oxobutanoate + L-alanine = (2S)-2-aminobutanoate + pyruvate

  Catalysed by NOS3, NOS1, NOS2, SLC7A6 and 1 morecytosol, extracellular spaceOne of 3 routes

• thio-Mo-molybdopterinReach from here →
  1. N-(omega)-Hydroxyarginine,NADPH:oxygen oxidoreductase (nitric-oxide-forming)
  2. transport of citrulline and cysteine (cytosol to extracellular)
  3. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O

  Catalysed by NOS3, NOS1, NOS2, SLC7A6 and 1 morecytosol, extracellular space

• glycodeoxycholateReach from here →
  1. N-(omega)-Hydroxyarginine,NADPH:oxygen oxidoreductase (nitric-oxide-forming)
  2. transport of citrulline and glycine (cytosol to extracellular)
  3. Glycodeoxycholate amidohydrolase

  Catalysed by NOS3, NOS1, NOS2, SLC7A9 and 2 morecytosol, extracellular spaceOne of 2 routes

• N-tetradecanoylglycineReach from here →
  1. N-(omega)-Hydroxyarginine,NADPH:oxygen oxidoreductase (nitric-oxide-forming)
  2. transport of citrulline and glycine (cytosol to extracellular)
  3. tetradecanoyl-CoA + glycine = N-tetradecanoylglycine + CoA + H(+)

  Catalysed by NOS3, NOS1, NOS2, SLC7A9 and 3 morecytosol, extracellular space

• N-eicosanoylglycinateReach from here →
  1. N-(omega)-Hydroxyarginine,NADPH:oxygen oxidoreductase (nitric-oxide-forming)
  2. transport of citrulline and glycine (cytosol to extracellular)
  3. eicosanoyl-CoA + glycine = N-eicosanoylglycinate + CoA + H(+)

  Catalysed by NOS3, NOS1, NOS2, SLC7A9 and 3 morecytosol, extracellular space

• N-docosanoylglycineReach from here →
  1. N-(omega)-Hydroxyarginine,NADPH:oxygen oxidoreductase (nitric-oxide-forming)
  2. transport of citrulline and glycine (cytosol to extracellular)
  3. docosanoyl-CoA + glycine = N-docosanoylglycine + CoA + H(+)

  Catalysed by NOS3, NOS1, NOS2, SLC7A9 and 3 morecytosol, extracellular space

• N-hexacosanoylglycineReach from here →
  1. N-(omega)-Hydroxyarginine,NADPH:oxygen oxidoreductase (nitric-oxide-forming)
  2. transport of citrulline and glycine (cytosol to extracellular)
  3. hexacosanoyl-CoA + glycine = N-hexacosanoylglycine + CoA + H(+)

  Catalysed by NOS3, NOS1, NOS2, SLC7A9 and 3 morecytosol, extracellular space

• an N(2)-acyl-L-glutamineReach from here →
  1. N-(omega)-Hydroxyarginine,NADPH:oxygen oxidoreductase (nitric-oxide-forming)
  2. transport of citrulline and glutamine (cytosol to extracellular)
  3. an acyl-CoA + L-glutamine = an N(2)-acyl-L-glutamine + CoA + H(+)

  Catalysed by NOS3, NOS1, NOS2, SLC7A6 and 2 morecytosol, extracellular space