L-phenylalanine

Three steps

• (9Z,12Z,15Z,18Z,21Z)-tetracosapentaenoyl-CoAReach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase ((9Z,12Z,15Z,18Z,21Z)-TPA)

  Catalysed by SLC7A5, BAAT, SLC27A2, ACSL4 and 6 moreextracellular space, cytosol, peroxisomeOne of 5 routes

• (6Z,9Z,12Z,15Z,18Z,21Z)-tetracosahexaenoyl-CoAReach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase ((6Z,9Z,12Z,15Z,18Z,21Z)-THA)

  Catalysed by SLC7A5, BAAT, SLC27A2, ACSL4 and 6 moreextracellular space, cytosol, peroxisomeOne of 4 routes

• (15Z)-tetracosenoyl-CoAReach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (nervonic acid)

  Catalysed by SLC7A5, BAAT, SLC27A2, ACSL4 and 6 moreextracellular space, cytosol, peroxisomeOne of 6 routes

• (17Z)-hexacosenoyl-CoAReach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (ximenic acid)

  Catalysed by SLC7A5, BAAT, SLC27A2, ACSL4 and 6 moreextracellular space, cytosol, peroxisomeOne of 4 routes

• CHEBI:742324Reach from here →
  1. L-dopa(out) + L-phenylalanine(in) = L-dopa(in) + L-phenylalanine(out)
  2. L-dopa + H(+) = dopamine + CO2
  3. S-Adenosyl-L-methionine:catechol O-methyltransferase

  Catalysed by SLC7A8, DDC, COMT, LRTOMTinner side of the membrane, outer side of the membrane, cytosol

• (8Z,11Z,14Z)-eicosatrienoyl-CoAReach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)

  Catalysed by SLC7A5, BAAT, SLC27A2, ACSL4 and 6 moreextracellular space, cytosol, peroxisomeOne of 5 routes

• (8Z,11Z,14Z,17Z)-eicosatetraenoyl-CoAReach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (omega-3-arachidonic acid)

  Catalysed by SLC7A5, BAAT, SLC27A2, ACSL4 and 6 moreextracellular space, cytosol, peroxisomeOne of 5 routes

• (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoAReach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (DHA)

  Catalysed by SLC7A5, BAAT, SLC27A2, ACSL4 and 6 moreextracellular space, cytosol, peroxisomeOne of 7 routes

• heptadecanoyl-CoAReach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (margaric acid)

  Catalysed by SLC7A5, BAAT, SLC27A2, ACSL4 and 6 moreextracellular space, cytosol, peroxisomeOne of 6 routes

• (9Z)-heptadecenoyl-CoAReach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (9-heptadecylenic acid)

  Catalysed by SLC7A5, BAAT, SLC27A2, ACSL4 and 6 moreextracellular space, cytosol, peroxisomeOne of 5 routes

• (11Z,14Z,17Z)-eicosatrienoyl-CoAReach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase ((11Z,14Z,17Z)-eicosatrienoic acid)

  Catalysed by SLC7A5, BAAT, SLC27A2, ACSL4 and 6 moreextracellular space, cytosol, peroxisomeOne of 5 routes

• nonadecanoyl-CoAReach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (nonadecylic acid)

  Catalysed by SLC7A5, BAAT, SLC27A2, ACSL4 and 6 moreextracellular space, cytosol, peroxisomeOne of 6 routes

• (11Z)-octadecenoyl-CoAReach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix

  Catalysed by SLC7A5, BAAT, CPT1A, CPT1C and 1 moreextracellular space, cytosol, peroxisomeOne of 3 routes

• (12R)-hydroperoxy-(5Z,8Z,10E,14Z)-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 + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (12R)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate

  Catalysed by PM20D1, ALOX12B

• (8S)-hydroperoxy-(5Z,9E,11Z,14Z)-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 + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  3. Arachidonate:oxygen 8-oxidoreductase

  Catalysed by PM20D1, ALOX12cytosolOne of 2 routes

• 2-O-(5Z,8Z,11Z,14Z)-eicosatetraenylglycerolReach 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 + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  3. fatty acid amide hydrolase (arachidonate)

  Catalysed by PM20D1, FAAHcytosol

• dodecanedioyl-CoAReach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Activation of dodecanedioic acid

  Catalysed by SLC7A5, BAATextracellular space, cytosol, peroxisomeOne of 4 routes

• decanedioyl-CoAReach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Production of Sebacoylcarnitine

  Catalysed by SLC7A5, BAAT, CPT1A, CPT1C and 1 moreextracellular space, cytosol, peroxisomeOne of 4 routes

• octanedioyl-CoAReach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Production of Suberylcarnitine

  Catalysed by SLC7A5, BAAT, CPT1A, CPT1C and 1 moreextracellular space, cytosol, peroxisomeOne of 4 routes

• hexanedioyl-CoAReach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Activation of adipic acid for Formation of Adipoyl Carnitine

  Catalysed by SLC7A5, BAATextracellular space, cytosol, peroxisomeOne of 4 routes

• (4Z,7Z,10Z,13Z,16Z)-docosapentaenoyl-CoAReach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase ((4Z,7Z,10Z,13Z,16Z)-DPA)

  Catalysed by SLC7A5, BAAT, SLC27A2, ACSL4 and 6 moreextracellular space, cytosol, peroxisomeOne of 7 routes

• (11Z,14Z)-eicosadienoyl-CoAReach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase ((11Z,14Z)-eicosadienoic acid)

  Catalysed by SLC7A5, BAAT, SLC27A2, ACSL4 and 6 moreextracellular space, cytosol, peroxisomeOne of 5 routes

• 2-iminobutanoateReach from here →
  1. transport of phenylalanine and threonine (cytosol to extracellular)
  2. L-threonine ammonia-lyase (2-oxobutanoate-forming)
  3. 2-iminobutanoate + H2O = 2-oxobutanoate + NH4(+)

  Catalysed by SLC7A5, SDS, SDSL, RIDAextracellular space, cytosol

• (R)-3-hydroxy-(11Z)-octadecenoyl-CoAReach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Production of 3-Hydroxyoctadecenoylcarnitinec

  Catalysed by SLC7A5, BAAT, CPT1A, CPT1C and 1 moreextracellular space, cytosol, peroxisome

• (13Z)-eicosenoyl-CoAReach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase ((13Z)-eicosenoic acid)

  Catalysed by SLC7A5, BAAT, SLC27A2, ACSL4 and 6 moreextracellular space, cytosol, peroxisomeOne of 5 routes

• 2-aminoprop-2-enoateReach from here →
  1. transport of alanine and phenylalanine (cytosol to extracellular)
  2. D-serine(out) + L-alanine(in) = D-serine(in) + L-alanine(out)
  3. D-serine = 2-aminoprop-2-enoate + H2O

  Catalysed by SLC7A5, SLC7A10, SRRextracellular space, cytosol, inner side of the membrane, outer side of the membrane

• 20-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. Resistance-Nodulation-Cell Division (Rnd) Tcdb:2.A.60.1.2

  Catalysed by SLC7A5, GSS, SLCO2A1extracellular space, cytosolOne of 5 routes

• 11,12-epoxy-(5Z,8Z,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 + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = 11,12-epoxy-(5Z,8Z,14Z)-eicosatrienoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by PM20D1, CYP2C9

• 19-hydroxy-(5Z,8Z,11Z,14Z)-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 + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = 19-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by PM20D1, CYP1A1, CYP1A2, CYP2C9 and 2 more

• N-acetyl-L-aspartyl-L-glutamateReach from here →
  1. L-aspartate(in) + L-phenylalanine(out) = L-aspartate(out) + L-phenylalanine(in)
  2. acetyl-CoA:L-aspartate N-acetyltransferase
  3. N-acetyl-L-aspartate + L-glutamate + ATP = N-acetyl-L-aspartyl-L-glutamate + ADP + phosphate + H(+)

  Catalysed by SLC7A13, NAT8L, RIMKLA, RIMKLBinner side of the membrane, outer side of the membrane, mitochondrial matrix

• N-acetyl-L-aspartyl-L-glutamyl-L-glutamateReach from here →
  1. L-aspartate(in) + L-phenylalanine(out) = L-aspartate(out) + L-phenylalanine(in)
  2. acetyl-CoA:L-aspartate N-acetyltransferase
  3. N-acetyl-L-aspartate + 2 L-glutamate + 2 ATP = N-acetyl-L-aspartyl-L-glutamyl-L-glutamate + 2 ADP + 2 phosphate + 2 H(+)

  Catalysed by SLC7A13, NAT8L, RIMKLAinner side of the membrane, outer side of the membrane, mitochondrial matrix

• 4,8-dimethylnonanoyl-CoAReach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Carnitine Dimethyl Nonanoyl Transferase, Revsible, Peroxisomal

  Catalysed by SLC7A5, BAAT, CRAT, CROTextracellular space, cytosol, peroxisomeOne of 3 routes

• tetradecanedioyl-CoAReach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Fatty Acid Beta Oxidation (C16Dc->C14Dc), Peroxisomal

  Catalysed by SLC7A5, BAAT, ACAA1, HSD17B4 and 2 moreextracellular space, cytosol, peroxisome

• hexadecanedioyl-CoAReach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Production of Hexadecanedioylcarnitine

  Catalysed by SLC7A5, BAAT, CPT1A, CPT1C and 1 moreextracellular space, cytosol, peroxisomeOne of 2 routes

• O-dodecanoyl-R-carnitineReach from here →
  1. Transport of L-Phenylalanine by Atb0 Transporter
  2. Carnitine Transport by Atb0
  3. carnitine O-palmitoyltransferase (dodecanoylcarnitine)

  Catalysed by SLC6A14, CPT1A, CPT1C, CPT1Bextracellular space, cytosolOne of 7 routes

• pristanoyl-CoAReach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. fatty-acid-CoA ligase

  Catalysed by SLC7A5, BAAT, SLC27A2extracellular space, cytosol, peroxisomeOne of 2 routes

• an L-aminoacyl-L-amino acidReach from here →
  1. Transport of L-Kynurenine
  2. an L-alpha-amino acid(in) + L-kynurenine(out) = an L-alpha-amino acid(out) + L-kynurenine(in)
  3. an L-aminoacyl-L-amino acid + H2O = 2 an L-alpha-amino acid

  Catalysed by SLC7A8, SLC7A11, DPEP1, DPEP2extracellular space, cytosol, inner side of the membrane, outer side of the membrane

• undecanoyl-CoAReach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. medium-chain acyl-CoA ligase (undecylic acid)

  Catalysed by SLC7A5, BAAT, ACSM4, ACSM1 and 4 moreextracellular space, cytosol, peroxisomeOne of 3 routes

• a fatty acyl-CoAReach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. a fatty acyl-CoA + glycine = an N-(fatty acyl)-glycine + CoA + H(+)
  3. a fatty acyl-CoA + glycine = an N-(fatty acyl)-glycine + CoA + H(+)

  Catalysed by SLC7A5, GLYATL2extracellular space, cytosol

• (9S)-hydroxy-(10E,12Z)-octadecadienoateReach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. gamma-L-glutamyl-L-cysteine + glycine + ATP = glutathione + ADP + phosphate + H(+)
  3. (9S)-hydroperoxy-(10E,12Z)-octadecadienoate + 2 glutathione = (9S)-hydroxy-(10E,12Z)-octadecadienoate + glutathione disulfide + H2O

  Catalysed by SLC7A5, GSS, GPX1, GPX4extracellular space, cytosolOne of 2 routes

• (9R)-hydroxy-(10E,12Z)-octadecadienoateReach from here →
  1. transport of alanine and phenylalanine (cytosol to extracellular)
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. (9Z,12Z)-octadecadienoate + AH2 + O2 = (9R)-hydroxy-(10E,12Z)-octadecadienoate + A + H2O

  Catalysed by SLC7A5, MOCOS, PTGS1, PTGS2extracellular space, cytosol

• N-(9Z-octadecenoyl)-sphing-4-enineReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  3. N-(9Z-octadecenoyl)-sphing-4-enine + H2O = sphing-4-enine + (9Z)-octadecenoate

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

• 18-hydroxy-(9Z)-octadecenoateReach from here →
  1. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  2. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O
  3. (9Z)-octadecenoate + reduced [NADPH--hemoprotein reductase] + O2 = 18-hydroxy-(9Z)-octadecenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by PM20D1, CYP4A11, CYP4F11

• ursodeoxycholateReach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. transport of GSH and ursodeoxycholate (cytosol to extracellular)

  Catalysed by SLC7A5, GSS, SLCO1A2, SLCO1B3extracellular space, cytosolOne of 2 routes

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

  Catalysed by PM20D1, ABHD12

• (11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoateReach from here →
  1. transport of alanine and phenylalanine (cytosol to extracellular)
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoate + A + H2O

  Catalysed by SLC7A5, MOCOS, PTGS2extracellular space, cytosolOne of 3 routes

• (15R)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. transport of alanine and phenylalanine (cytosol to extracellular)
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (15R)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoate + A + H2O

  Catalysed by SLC7A5, MOCOS, PTGS2extracellular space, cytosolOne of 3 routes

• (15R)-hydroperoxy-(5Z,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 + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (15R)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate

  Catalysed by PM20D1, PTGS2

• 11R-hydroperoxy-(5Z,8Z,12E,14Z)-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 + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O
  3. Arachidonate: oxygen 11-oxidoreductase

  Catalysed by PM20D1, ALOX12cytosolOne of 2 routes

• prostaglandin G2Reach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. transport of GSH and prostaglandin G2 (cytosol to extracellular)

  Catalysed by SLC7A5, GSS, SLCO2A1extracellular space, cytosolOne of 4 routes