N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine

Three steps

• (5E)-tetradecenoyl-(R)-carnitineReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. Utilized Transport
  3. carnitine O-palmitoyltransferase ((9E)-tetradecenoyl-CoA)

  Catalysed by PM20D1, CPT1A, CPT1C, CPT1Bendoplasmic reticulum, cytosolOne of 7 routes

• tauroursodeoxycholateReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. transport of arachidonate (cytosol to extracellular)
  3. transport of S-glutathionyl-2-4-dinitrobenzene (cytosol to extracellular)

  Catalysed by PM20D1, SLCO1B1, SLCO1A2, SLCO1B3extracellular space, cytosolOne of 4 routes

• glycoursodeoxycholateReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. transport of arachidonate (cytosol to extracellular)
  3. transport of glycoursodeoxycholate (cytosol to extracellular)

  Catalysed by PM20D1, SLCO1B1, SLCO1A2, SLCO1B3extracellular space, cytosolOne of 6 routes

• (14S,15S)-epoxy-(5Z,8Z,10E,12E)-eicosatetraenoateReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate
  3. (15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate = (14S,15S)-epoxy-(5Z,8Z,10E,12E)-eicosatetraenoate + H2O

  Catalysed by PM20D1, ALOX15B, ALOX15, ALOX12

• N-(12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoyl-glycineReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycine + H2O = (5Z,8Z,11Z,14Z)-eicosatetraenoate + glycine
  3. N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycine + O2 = N-(12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoyl-glycine

  Catalysed by PM20D1, FAAH, ALOX15, ALOX12

• N-(15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoyl-glycineReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycine + H2O = (5Z,8Z,11Z,14Z)-eicosatetraenoate + glycine
  3. N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycine + O2 = N-(15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoyl-glycine

  Catalysed by PM20D1, FAAH, ALOX15B, ALOX15 and 1 more

• (15S)-hydroxy-(5Z,8Z,11Z,13E,17Z)-eicosapentaenoateReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. arachidonate:oxygen 15-oxidoreductase
  3. palmitoyl-CoA hydrolase (15(S)-HPETE)

  Catalysed by PM20D1, ALOX15B, ALOX15cytosol

• (8S)-hydroxy-(11S,12S)-epoxy-(5Z,9E,14Z)-eicosatrienoateReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate
  3. (12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate = (8S)-hydroxy-(11S,12S)-epoxy-(5Z,9E,14Z)-eicosatrienoate

  Catalysed by PM20D1, ALOX5, ALOX15, ALOX12

• (11S,15S)-dihydroxy-14(R)-S-glutathionyl-(5Z,8Z,12E)-eicosatrienoateReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. glutathione transferase (GSH)

  Catalysed by PM20D1, PTGES, MGST3, GSTA4 and 18 moreextracellular space, cytosolOne of 4 routes

• prostaglandin E3Reach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. transport of arachidonate (cytosol to extracellular)
  3. transport of prostaglandin E3 (cytosol to extracellular)

  Catalysed by PM20D1, SLCO1B1extracellular space, cytosolOne of 4 routes

• prostaglandin A2Reach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. transport of arachidonate (cytosol to extracellular)
  3. transport of prostaglandin A2 (cytosol to extracellular)

  Catalysed by PM20D1, SLCO1B1extracellular space, cytosolOne of 4 routes

• prostaglandin B1Reach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. transport of arachidonate (cytosol to extracellular)
  3. transport of prostaglandin B1 (cytosol to extracellular)

  Catalysed by PM20D1, SLCO1B1extracellular space, cytosolOne of 4 routes

• 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phospho-(1D-myo-inositol)Reach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + ATP + CoA = (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + AMP + diphosphate
  3. 1-octadecanoyl-sn-glycero-3-phospho-(1D-myo-inositol) + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phospho-(1D-myo-inositol) + CoA

  Catalysed by PM20D1, SLC27A2, ACSL4, ACSL3 and 9 more

• leukotriene F4Reach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. transport of arachidonate (cytosol to extracellular)
  3. transport of leukotriene F4 (cytosol to extracellular)

  Catalysed by PM20D1, SLCO1B1extracellular space, cytosolOne of 4 routes

• N-(9Z-octadecenoyl)glycineReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. transport of glycine and phenylalanine (cytosol to extracellular)
  3. (9Z)-octadecenoyl-CoA + glycine = N-(9Z-octadecenoyl)glycine + CoA + H(+)

  Catalysed by PM20D1, SLC7A5, GLYATL3, GLYATL2extracellular space, cytosol

• N-(9Z-octadecenoyl)-L-leucineReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. transport of leucine and phenylalanine (cytosol to extracellular)
  3. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate

  Catalysed by PM20D1, SLC7A5extracellular space, cytosol

• N-octadecanoylglycineReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. transport of glycine and phenylalanine (cytosol to extracellular)
  3. octadecanoyl-CoA + glycine = N-octadecanoylglycine + CoA + H(+)

  Catalysed by PM20D1, SLC7A5, GLYATL2extracellular space, cytosol

• N-(9Z-hexadecenoyl)-glycineReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. transport of glycine and phenylalanine (cytosol to extracellular)
  3. (9Z)-hexadecenoyl-CoA + glycine = N-(9Z-hexadecenoyl)-glycine + CoA + H(+)

  Catalysed by PM20D1, SLC7A5, GLYATL2extracellular space, cytosol

• 8,9-epoxy-(5Z,11Z,14Z)-eicosatrienoyl-CoAReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. unspecific monooxygenase (arachidonate)
  3. 8,9-epoxy-(5Z,11Z,14Z)-eicosatrienoate + ATP + CoA = 8,9-epoxy-(5Z,11Z,14Z)-eicosatrienoyl-CoA + AMP + diphosphate

  Catalysed by PM20D1, CYP1A1, CYP1A2, CYP2E1 and 24 morecytosol

• 11,12-epoxy-(5Z,8Z,14Z)-eicosatrienoyl-CoAReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = 11,12-epoxy-(5Z,8Z,14Z)-eicosatrienoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
  3. 11,12-epoxy-(5Z,8Z,14Z)-eicosatrienoate + ATP + CoA = 11,12-epoxy-(5Z,8Z,14Z)-eicosatrienoyl-CoA + AMP + diphosphate

  Catalysed by PM20D1, CYP2C9, ACSL4, ACSL3 and 1 more

• 14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoyl-CoAReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. unspecific monooxygenase (arachidonate)
  3. 14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoate + ATP + CoA = 14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoyl-CoA + AMP + diphosphate

  Catalysed by PM20D1, CYP1A1, CYP1A2, CYP2E1 and 28 morecytosol

• 5,6-epoxy-(8Z,11Z,14Z)-eicosatrienoyl-CoAReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. unspecific monooxygenase (arachidonate)
  3. 5,6-epoxy-(8Z,11Z,14Z)-eicosatrienoate + ATP + CoA = 5,6-epoxy-(8Z,11Z,14Z)-eicosatrienoyl-CoA + AMP + diphosphate

  Catalysed by PM20D1, CYP1A1, CYP1A2, CYP2E1 and 24 morecytosol

• 2-[15(S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoyl]-glycerolReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. fatty acid amide hydrolase (2-arachidonoylglycerol)
  3. 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + O2 = 2-[15(S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoyl]-glycerol

  Catalysed by PM20D1, FAAH, ALOX15Bcytosol

• (13S)-hydroxy-(14S,15S)-epoxy-(5Z,8Z,11Z)-eicosatrienoateReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate
  3. (15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate = (13S)-hydroxy-(14S,15S)-epoxy-(5Z,8Z,11Z)-eicosatrienoate

  Catalysed by PM20D1, ALOX15B, ALOX15, ALOX12 and 1 more

• (5S,15S)-dihydroperoxy-(6E,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (5S)-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate
  3. (5S)-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + O2 = (5S,15S)-dihydroperoxy-(6E,8Z,11Z,13E)-eicosatetraenoate

  Catalysed by PM20D1, ALOX5, ALOX15B

• N-hexadecanoylglycineReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. transport of glycine and phenylalanine (cytosol to extracellular)
  3. hexadecanoyl-CoA + glycine = N-hexadecanoylglycine + CoA + H(+)

  Catalysed by PM20D1, SLC7A5, GLYATL3extracellular space, cytosol

• N-dodecanoylglycineReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. transport of glycine and phenylalanine (cytosol to extracellular)
  3. dodecanoyl-CoA + glycine = N-dodecanoylglycine + CoA + H(+)

  Catalysed by PM20D1, SLC7A5, GLYATL2extracellular space, cytosol

• N-decanoylglycineReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. transport of glycine and phenylalanine (cytosol to extracellular)
  3. decanoyl-CoA + glycine = N-decanoylglycine + CoA + H(+)

  Catalysed by PM20D1, SLC7A5, GLYATL2extracellular space, cytosol

• N-octanoylglycineReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. transport of glycine and phenylalanine (cytosol to extracellular)
  3. octanoyl-CoA + glycine = N-octanoylglycine + CoA + H(+)

  Catalysed by PM20D1, SLC7A5, GLYATL2extracellular space, cytosol

• D-histidineReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. transport of ornithine and phenylalanine (cytosol to extracellular)
  3. D-histidine(in) + L-ornithine(out) + H(+)(in) = D-histidine(out) + L-ornithine(in) + H(+)(out)

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

• L-homoarginineReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. transport of arginine and phenylalanine (cytosol to extracellular)
  3. L-homoarginine(in) + L-arginine(out) = L-homoarginine(out) + L-arginine(in)

  Catalysed by PM20D1, SLC7A6, SLC25A29extracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 4 routes

• L-homocarnosineReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. transport of histidine and phenylalanine (cytosol to extracellular)
  3. Formation of homocarnosine

  Catalysed by PM20D1, SLC7A6, CARNS1extracellular space, cytosolOne of 2 routes

• N(1)-(5-phospho-beta-D-ribosyl)glycinamideReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. transport of glycine and phenylalanine (cytosol to extracellular)
  3. 5-phospho-beta-D-ribosylamine + glycine + ATP = N(1)-(5-phospho-beta-D-ribosyl)glycinamide + ADP + phosphate + H(+)

  Catalysed by PM20D1, SLC7A5, GARTextracellular space, cytosol

• L-cystine-bis-glycineReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. transport of glycine and phenylalanine (cytosol to extracellular)
  3. L-cystine-bis-glycine + 2 H2O = L-cystine + 2 glycine

  Catalysed by PM20D1, SLC7A5, DPEP1, DPEP2extracellular space, cytosol

• glycyldehydrophenylalanineReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. transport of glycine and phenylalanine (cytosol to extracellular)
  3. glycyldehydrophenylalanine + H2O = 2,3-didehydrophenylalanine + glycine

  Catalysed by PM20D1, SLC7A5, DPEP1extracellular space, cytosol

• 2-[12-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoyl]-glycerolReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. fatty acid amide hydrolase (2-arachidonoylglycerol)
  3. 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + O2 = 2-[12-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoyl]-glycerol

  Catalysed by PM20D1, FAAH, ALOX15Bcytosol

• 2-formamido-N(1)-(5-O-phospho-beta-D-ribosyl)acetamidineReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. transport of glutamine and phenylalanine (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 PM20D1, SLC7A5, PFASextracellular space, cytosol

• kinetensin-(1-8)Reach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. Chymase
  3. kinetensin + H2O = kinetensin-(1-8) + L-leucine

  Catalysed by PM20D1, CMA1, ACE2extracellular space

• an N-(fatty acyl)-glycineReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. transport of glycine and phenylalanine (cytosol to extracellular)
  3. a fatty acyl-CoA + glycine = an N-(fatty acyl)-glycine + CoA + H(+)

  Catalysed by PM20D1, SLC7A5, GLYATL2extracellular space, cytosol

• 1-(10Z-heptadecenoyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + ATP + CoA = (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + AMP + diphosphate
  3. 1-(10Z-heptadecenoyl)-sn-glycero-3-phosphoethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-(10Z-heptadecenoyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine + CoA

  Catalysed by PM20D1, SLC27A2, ACSL4, ACSL3 and 9 more

• N-(9Z,12Z-octadecadienoyl)-glycineReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. transport of glycine and phenylalanine (cytosol to extracellular)
  3. (9Z,12Z)-octadecadienoyl-CoA + glycine = N-(9Z,12Z-octadecadienoyl)-glycine + CoA + H(+)

  Catalysed by PM20D1, SLC7A5, GLYATL2extracellular space, cytosol

• (15S)-15-hydroperoxy-prostaglandin E2Reach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. Arachidonate:oxygen oxidoreductase
  3. prostaglandin G2 = (15S)-15-hydroperoxy-prostaglandin E2

  Catalysed by PM20D1, PTGS1, PTGS2, PTGESendoplasmic reticulum

• acetaldehydeReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. transport of phenylalanine and threonine (cytosol to extracellular)
  3. L-threonine acetaldehyde-lyase (glycine-forming)

  Catalysed by PM20D1, SLC7A5extracellular space, cytosol

• cholineReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. Transport of L-Phenylalanine by Atb0 Transporter
  3. transport of chloride and choline (cytosol to extracellular)

  Catalysed by PM20D1, SLC6A14, SLC5A7extracellular space, cytosol

• acetylcholineReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. transport of arachidonate (cytosol to extracellular)
  3. transport of acetylcholine (cytosol to extracellular)

  Catalysed by PM20D1, SLCO1B1, SLCO1B3extracellular space, cytosolOne of 4 routes

• pyruvateReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. transport of alanine and phenylalanine (cytosol to extracellular)
  3. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase

  Catalysed by PM20D1, SLC7A5, AGXT2extracellular space, cytosol, mitochondrial matrixOne of 16 routes

• propionyl-CoAReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. Utilized Transport
  3. Active Transport

  Catalysed by PM20D1endoplasmic reticulum, cytosol, mitochondrial matrixOne of 2 routes

• CHEBI:15570Reach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. transport of glycine and phenylalanine (cytosol to extracellular)
  3. transport of D-alanine and glycine (cytosol to extracellular)

  Catalysed by PM20D1, SLC7A5, SLC3A2, SLC7A10extracellular space, cytosolOne of 5 routes

• CHEBI:15611Reach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. transport of glycine and phenylalanine (cytosol to extracellular)
  3. S-Adenosyl-L-methionine:glycine N-methyltransferase

  Catalysed by PM20D1, SLC7A5, GNMTextracellular space, cytosol

• CHEBI:15650Reach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  2. transport of arachidonate (cytosol to extracellular)
  3. transport of leukotriene E4 (cytosol to extracellular)

  Catalysed by PM20D1, SLCO1B1extracellular space, cytosolOne of 4 routes