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

Three steps

• (5Z,8Z,11Z)-eicosatrienoateReach 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

• 1-(9Z-octadecenoyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phospho-1D-myo-inositolReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1D-myo-inositol) + H2O = sn-glycero-3-phospho-1D-myo-inositol + (9Z)-octadecenoate + H(+)
  3. 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1D-myo-inositol) + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-(9Z-octadecenoyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phospho-1D-myo-inositol + CoA

  Catalysed by PM20D1, ABHD12, AGPAT3, AGPAT5

• tricosanoateReach 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

• 3-phenyllactateReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. Phenylalanine Transaminase, Mitochondrial
  3. Formation of Phenyl-Lactate

  Catalysed by PM20D1, GOT2, TATmitochondrial matrix, cytosol

• thio-Mo-molybdopterinReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. transport of cysteine and phenylalanine (cytosol to extracellular)
  3. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O

  Catalysed by PM20D1, SLC7A5, MOCOSextracellular space, cytosol

• glycodeoxycholateReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. transport of glycine and phenylalanine (cytosol to extracellular)
  3. Glycodeoxycholate amidohydrolase

  Catalysed by PM20D1, SLC7A5extracellular space, cytosolOne of 2 routes

• 1'-[1,2-di-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho]-3'-[1-(9Z,12Z-octadecadienoyl)-2-(9Z-octadecenoyl)-sn-glycero-3-phospho]-glycerolReach 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'-[1,2-di-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho]-3'-[1-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho]-glycerol + (9Z)-octadecenoyl-CoA = 1'-[1,2-di-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho]-3'-[1-(9Z,12Z-octadecadienoyl)-2-(9Z-octadecenoyl)-sn-glycero-3-phospho]-glycerol + CoA

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

• O-(9Z)-octadecenoyl-(R)-carnitineReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  3. (R)-carnitine + (9Z)-octadecenoyl-CoA = O-(9Z)-octadecenoyl-(R)-carnitine + CoA

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

• O-4,8-dimethylnonanoyl-(R)-carnitineReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. Utilized Transport
  3. Carnitine Dimethyl Nonanoyl Transferase, Revsible, Peroxisomal

  Catalysed by PM20D1, CRAT, CROTendoplasmic reticulum, cytosol, peroxisomeOne of 5 routes

• 1-decanoyl-2-(9Z-octadecenoyl)-glycerolReach 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-decanoylglycerol + (9Z)-octadecenoyl-CoA = 1-decanoyl-2-(9Z-octadecenoyl)-glycerol + CoA

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

• N-tetradecanoylglycineReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. transport of glycine and phenylalanine (cytosol to extracellular)
  3. tetradecanoyl-CoA + glycine = N-tetradecanoylglycine + CoA + H(+)

  Catalysed by PM20D1, SLC7A5, GLYATL2extracellular space, cytosol

• N-eicosanoylglycinateReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. transport of glycine and phenylalanine (cytosol to extracellular)
  3. eicosanoyl-CoA + glycine = N-eicosanoylglycinate + CoA + H(+)

  Catalysed by PM20D1, SLC7A5, BAATextracellular space, cytosol

• N-docosanoylglycineReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. transport of glycine and phenylalanine (cytosol to extracellular)
  3. docosanoyl-CoA + glycine = N-docosanoylglycine + CoA + H(+)

  Catalysed by PM20D1, SLC7A5, BAATextracellular space, cytosol

• N-hexacosanoylglycineReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. transport of glycine and phenylalanine (cytosol to extracellular)
  3. hexacosanoyl-CoA + glycine = N-hexacosanoylglycine + CoA + H(+)

  Catalysed by PM20D1, SLC7A5, BAATextracellular space, cytosol

• an N(2)-acyl-L-glutamineReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. transport of glutamine and phenylalanine (cytosol to extracellular)
  3. an acyl-CoA + L-glutamine = an N(2)-acyl-L-glutamine + CoA + H(+)

  Catalysed by PM20D1, SLC7A5, GLYATL1B, GLYATL1extracellular space, cytosol