N-(9Z-octadecenoyl)-L-phenylalanine

Three steps

• 5,6,7,8-tetrahydrofolic acidReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. transport of glycine and phenylalanine (cytosol to extracellular)
  3. 5,10-Methylenetetrahydrofolate:glycine hydroxymethyltransferase

  Catalysed by PM20D1, SLC7A5, SHMT1extracellular space, cytosolOne of 2 routes

• S-disulfanyl-L-cysteineReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. transport of cysteine and phenylalanine (cytosol to extracellular)
  3. S-sulfanyl-L-cysteine + L-cysteine = S-disulfanyl-L-cysteine + L-alanine

  Catalysed by PM20D1, SLC7A5, CARS2extracellular space, cytosol

• 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(3'-(9Z-octadecenoyl)-1'-sn-glycerol)Reach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol) + H2O = sn-glycero-3-phospho-(1'-sn-glycerol) + (9Z)-octadecenoate + H(+)
  3. 2 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol) = 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(3'-(9Z-octadecenoyl)-1'-sn-glycerol) + sn-glycero-3-phospho-(1'-sn-glycerol)

  Catalysed by PM20D1, ABHD12, CLN5

• docosanoateReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by PM20D1cytosol, extracellular spaceOne of 12 routes

• CHEBI:240943Reach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. transport of glycine and phenylalanine (cytosol to extracellular)
  3. glycine N-acyltransferase (2-methylbutyryl-CoA)

  Catalysed by PM20D1, SLC7A5, GLYAT, GLYATL2 and 1 moreextracellular space, cytosol, mitochondrial matrixOne of 3 routes

• hypochlorous acidReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. Transport of L-Phenylalanine by Atb0 Transporter
  3. Peroxidase

  Catalysed by PM20D1, SLC6A14, LPOextracellular space, cytosolOne of 4 routes

• octadecanoateReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by PM20D1cytosol, extracellular spaceOne of 12 routes

• potassium atomReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. Transport of L-Phenylalanine by Atb0 Transporter
  3. transport of chloride (cytosol to extracellular)

  Catalysed by PM20D1, SLC6A14, SLC12A2, SLC12A1extracellular space, cytosolOne of 3 routes

• alpha-linolenic acidReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by PM20D1cytosol, extracellular spaceOne of 13 routes

• phenylacetylglycineReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. transport of glycine and phenylalanine (cytosol to extracellular)
  3. phenylacetyl-CoA:glycine N-phenylacetyltransferase

  Catalysed by PM20D1, SLC7A5, GLYATextracellular space, cytosolOne of 3 routes

• elaidic acidReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by PM20D1cytosol, extracellular spaceOne of 13 routes

• all-cis-docosa-4,7,10,13,16,19-hexaenoic acidReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by PM20D1cytosol, extracellular spaceOne of 12 routes

• 5-hydroxytryptophanReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. transport of phenylalanine and tryptophan (cytosol to extracellular)
  3. L-Tryptophan, Tetrahydrobiopterin:Oxygen Oxidoreductase (5-Hydroxylating)

  Catalysed by PM20D1, SLC7A5, TPH1, TPH2extracellular space, cytosolOne of 2 routes

• (2-hydroxyphenyl)acetic acidReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. Phenylalanine Transaminase, Mitochondrial
  3. Phenylpyruvate:oxygen oxidoreductase (hydroxylating,decarboxylating)

  Catalysed by PM20D1, GOT2, TAT, HPDmitochondrial matrix, cytosol

• CHEBI:28666Reach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. transport of glycine and phenylalanine (cytosol to extracellular)
  3. LTD4 hydrolysis

  Catalysed by PM20D1, SLC7A5extracellular space, cytosol

• pyridoxine 5'-phosphateReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. transport of alanine and phenylalanine (cytosol to extracellular)
  3. L-selenocysteine selenide-lyase (L-alanine-forming)

  Catalysed by PM20D1, SLC7A5, SCLYextracellular space, cytosol

• N-acetyl-L-cysteineReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. transport of cysteine and phenylalanine (cytosol to extracellular)
  3. N-acetylglutamate synthase (N-acetyl-L-cysteine)

  Catalysed by PM20D1, SLC7A5, NAGSextracellular space, cytosol, mitochondrial matrix

• K(+)Reach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. transport of cysteine and phenylalanine (cytosol to extracellular)
  3. K(+)(in) + L-cysteine(out) + 3 Na(+)(out) + H(+)(out) = K(+)(out) + L-cysteine(in) + 3 Na(+)(in) + H(+)(in)

  Catalysed by PM20D1, SLC7A5, SLC1A1extracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 4 routes

• Cys-tRNA(Cys)Reach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. transport of cysteine and phenylalanine (cytosol to extracellular)
  3. L-Cysteine:tRNA(Cys) ligase (AMP-forming)

  Catalysed by PM20D1, SLC7A5, CARS1extracellular space, cytosol

• Gly-tRNA(Gly)Reach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. transport of glycine and phenylalanine (cytosol to extracellular)
  3. glycine:tRNA(Gly) ligase (AMP-forming)

  Catalysed by PM20D1, SLC7A5, GARS1extracellular space, cytosol

• Asp-tRNA(Asp)Reach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. L-aspartate(in) + L-phenylalanine(out) = L-aspartate(out) + L-phenylalanine(in)
  3. L-Aspartate:tRNA(Asp) ligase (AMP-forming)

  Catalysed by PM20D1, SLC7A13, DARS1inner side of the membrane, outer side of the membrane, cytosol

• Trp-tRNA(Trp)Reach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. transport of phenylalanine and tryptophan (cytosol to extracellular)
  3. L-Tryptophan -tRNA(Trp) ligase (AMP-forming)

  Catalysed by PM20D1, SLC7A5, WARS1extracellular space, cytosol

• Ile-tRNA(Ile)Reach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. transport of isoleucine and phenylalanine (cytosol to extracellular)
  3. L-Isoleucine:tRNA(Ile) ligase (AMP-forming)

  Catalysed by PM20D1, SLC7A5, IARS1extracellular space, cytosol

• Gln-tRNA(Gln)Reach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. transport of glutamine and phenylalanine (cytosol to extracellular)
  3. L-Glutamine:tRNA(Gln) ligase (AMP-forming)

  Catalysed by PM20D1, SLC7A5, QARS1extracellular space, cytosol

• isocyanateReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. transport of citrulline and phenylalanine (cytosol to extracellular)
  3. L-citrulline + H(+) = isocyanate + L-ornithine

  Catalysed by PM20D1, SLC7A6, LACC1extracellular space, cytosol

• Asn-tRNA(Asn)Reach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. transport of asparagine and phenylalanine (cytosol to extracellular)
  3. L-Asparagine:tRNA(Asn) ligase (AMP-forming)

  Catalysed by PM20D1, SLC7A5, NARS1extracellular space, cytosol

• glycocholateReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. transport of glycine and phenylalanine (cytosol to extracellular)
  3. bile acid-CoA: amino acid N-acyltransferase

  Catalysed by PM20D1, SLC7A5, BAATextracellular space, cytosol, peroxisomeOne of 3 routes

• hydrogen sulfideReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. transport of cysteine and phenylalanine (cytosol to extracellular)
  3. L-cysteine hydrogen-sulfide-lyase (deaminating

  Catalysed by PM20D1, SLC7A5, CTHextracellular space, cytosolOne of 2 routes

• CHEBI:30249Reach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. transport of phenylalanine and tryptophan (cytosol to extracellular)
  3. L-tryptophan:oxygen 2,3-oxidoreductase (decyclizing)

  Catalysed by PM20D1, SLC7A5, IDO1, TDO2 and 1 moreextracellular space, cytosol

• formic acidReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. Transport of L-Phenylalanine by Atb0 Transporter
  3. transport of chloride and formate (cytosol to extracellular)

  Catalysed by PM20D1, SLC6A14, SLC26A4extracellular space, cytosolOne of 2 routes

• anthranilic acidReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. Transport of L-Kynurenine
  3. L-Kynurenine hydrolase

  Catalysed by PM20D1, SLC7A8, KYNUextracellular space, cytosol

• malonic acidReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. Transport of L-Phenylalanine by Atb0 Transporter
  3. Malonate Transport, Antiport with Chloride

  Catalysed by PM20D1, SLC6A14extracellular space, cytosolOne of 2 routes

• tetradecanoateReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by PM20D1cytosol, extracellular spaceOne of 12 routes

• hexacosanoateReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by PM20D1cytosol, extracellular spaceOne of 12 routes

• tetracosanoateReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by PM20D1cytosol, extracellular spaceOne of 12 routes

• an N-acylsphinganineReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. (10Z)-heptadecenoic acid formation
  3. N-acylsphingosine amidohydrolase

  Catalysed by PM20D1, ASAH1, ACER2, ACER1 and 2 morecytosol

• eicosanoateReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by PM20D1cytosol, extracellular spaceOne of 12 routes

• (9Z)-hexadecenoateReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by PM20D1cytosol, extracellular spaceOne of 18 routes

• (15Z)-tetracosenoateReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by PM20D1cytosol, extracellular spaceOne of 12 routes

• (5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by PM20D1cytosol, extracellular spaceOne of 15 routes

• (11Z)-eicosenoateReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by PM20D1cytosol, extracellular spaceOne of 12 routes

• L-lysineReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. transport of leucine and phenylalanine (cytosol to extracellular)
  3. L-lysine(in) + L-leucine(out) + Na(+)(out) = L-lysine(out) + L-leucine(in) + Na(+)(in)

  Catalysed by PM20D1, SLC7A5, SLC7A7extracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 5 routes

• D-lysineReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. transport of ornithine and phenylalanine (cytosol to extracellular)
  3. D-lysine(in) + L-ornithine(out) = D-lysine(out) + L-ornithine(in)

  Catalysed by PM20D1, SLC7A6, SLC25A2extracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• putrescineReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. transport of arginine and phenylalanine (cytosol to extracellular)
  3. Putrescine Export via Putrescine/Arginine Antiporter

  Catalysed by PM20D1, SLC7A6, SLC3A2, SLC7A7extracellular space, cytosolOne of 4 routes

• D-arginineReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. transport of ornithine and phenylalanine (cytosol to extracellular)
  3. D-arginine(in) + L-ornithine(out) = D-arginine(out) + L-ornithine(in)

  Catalysed by PM20D1, SLC7A6, SLC25A2extracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• N-carbamoyl-L-aspartateReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. L-aspartate(in) + L-phenylalanine(out) = L-aspartate(out) + L-phenylalanine(in)
  3. carbamoyl phosphate + L-aspartate = N-carbamoyl-L-aspartate + phosphate + H(+)

  Catalysed by PM20D1, SLC7A13, CADinner side of the membrane, outer side of the membrane

• 4-methylthio-2-oxobutanoic acidReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. transport of methionine and phenylalanine (cytosol to extracellular)
  3. L-Methionine:oxygen oxidoreductase (deaminating)

  Catalysed by PM20D1, SLC7A5, IL4I1extracellular space, cytosol

• di-mu-sulfido-diiron(2+)Reach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. transport of cysteine and phenylalanine (cytosol to extracellular)
  3. De novo synthesis of 2Fe2S

  Catalysed by PM20D1, SLC7A5, NDUFAB1, FDXR and 5 moreextracellular space, cytosol, mitochondrial matrix

• 1-O-hexadecyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphocholineReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  3. 1-O-hexadecyl-sn-glycero-3-phosphocholine + (9Z)-octadecenoyl-CoA = 1-O-hexadecyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by PM20D1, SLC27A2, ACSL3, ACSL1 and 6 more

• (S)-3-methyl-2-oxopentanoateReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. transport of isoleucine and phenylalanine (cytosol to extracellular)
  3. L-isoleucine + 2-oxoglutarate = (S)-3-methyl-2-oxopentanoate + L-glutamate

  Catalysed by PM20D1, SLC7A5, BCAT2, BCAT1extracellular space, cytosol