L-phenylalanine

Three steps

• 2,3-didehydrophenylalanineReach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. glycyldehydrophenylalanine + H2O = 2,3-didehydrophenylalanine + glycine
  3. glycyldehydrophenylalanine + H2O = 2,3-didehydrophenylalanine + glycine

  Catalysed by SLC7A5, DPEP1extracellular space, cytosol

• S-adenosylglutathioneReach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. gamma-L-glutamyl-L-cysteine + glycine + ATP = glutathione + ADP + phosphate + H(+)
  3. apo-[alkylcobalamin reductase] + adenosylcob(III)alamin + glutathione = S-adenosylglutathione + cob(I)alamin-[alkylcobalamin reductase] + H(+)

  Catalysed by SLC7A5, GSS, MMACHCextracellular space, cytosol

• 8-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 to 8-peroxy-(5Z,9E,11Z,14Z)-eicosatetraenoate conversion

  Catalysed by PM20D1cytosolOne of 2 routes

• N(2)-formyl-N(1)-(5-phospho-beta-D-ribosyl)glycinamideReach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. 5-phospho-beta-D-ribosylamine + glycine + ATP = N(1)-(5-phospho-beta-D-ribosyl)glycinamide + ADP + phosphate + H(+)
  3. N(1)-(5-phospho-beta-D-ribosyl)glycinamide + (6R)-10-formyltetrahydrofolate = N(2)-formyl-N(1)-(5-phospho-beta-D-ribosyl)glycinamide + (6S)-5,6,7,8-tetrahydrofolate + H(+)

  Catalysed by SLC7A5, GARTextracellular space, cytosol

• N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-serineReach 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. N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-serine + H2O = (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-serine

  Catalysed by PM20D1, FAAH

• (7Z)-octadecenoyl-CoAReach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. carnitine O-palmitoyltransferase ((7Z)-octadecenoyl-CoA)

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

• CHEBI:15345Reach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Acetoacetate:CoA ligase (AMP-forming)

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

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

  Catalysed by SLC7A5, GSS, SLCO1A2, SLCO1B3extracellular space, cytosolOne of 5 routes

• acetylpyruvateReach from here →
  1. transport of alanine and phenylalanine (cytosol to extracellular)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. acetylpyruvate + H2O = acetate + pyruvate + H(+)

  Catalysed by SLC7A5, AGXT2, FAHD1extracellular space, cytosol, mitochondrial matrix

• all-trans-retinoic acidReach from here →
  1. transport of alanine and phenylalanine (cytosol to extracellular)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. transport of pyruvate and retinoate (cytosol to extracellular)

  Catalysed by SLC7A5, AGXT2, SLC16A4, SLC16A5 and 4 moreextracellular space, cytosol, mitochondrial matrixOne of 4 routes

• CHEBI:15380Reach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. 5-aminolevulinate synthase (2-amino-3-oxoadipate)

  Catalysed by SLC7A5, BAAT, ALAS1, CPNE7extracellular space, cytosol, peroxisome, mitochondrial matrixOne of 8 routes

• CHEBI:15477Reach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. glycine N-acyltransferase (2-methylbutyryl-CoA)

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

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

  Catalysed by SLC7A5, BAAT, CPT1A, CPT1Bextracellular space, cytosol, peroxisomeOne of 2 routes

• isobutyryl-CoAReach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. acetyl-CoA C-acyltransferase (3-oxo-4-methyl-pentanoyl-CoA)

  Catalysed by SLC7A5, BAAT, HADHA, ACAA2 and 1 moreextracellular space, cytosol, peroxisome, mitochondrial matrixOne of 3 routes

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

  Catalysed by SLC7A5, BAAT, GLYATextracellular space, cytosol, peroxisome, mitochondrial matrix

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

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

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

  Catalysed by SLC7A5, BAAT, SLC27A2, ACSL4 and 6 moreextracellular space, cytosol, peroxisomeOne of 14 routes

• CHEBI:15519Reach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. propanoyl-CoA C-acyltransferase

  Catalysed by SLC7A5, BAAT, ACAA1, SCP2 and 1 moreextracellular space, cytosol, peroxisomeOne of 2 routes

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

  Catalysed by SLC7A5, BAAT, SLC27A2, ACSL4 and 6 moreextracellular space, cytosol, peroxisomeOne of 11 routes

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

  Catalysed by SLC7A5, BAAT, CPT1A, CPT1C and 1 moreextracellular space, cytosol, peroxisomeOne of 14 routes

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

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

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

  Catalysed by SLC7A5, BAAT, ACSS3, ACSS2 and 1 moreextracellular space, cytosol, peroxisomeOne of 46 routes

• (S)-malateReach from here →
  1. Phenylalanine Transaminase, Mitochondrial
  2. glyoxylate + L-phenylalanine = 3-phenylpyruvate + glycine
  3. glyoxylate + acetyl-CoA + H2O = (S)-malate + CoA + H(+)

  Catalysed by GOT2, TAT, AADAT, CLYBLmitochondrial matrixOne of 13 routes

• 12(S)-HPETEReach 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 12-oxidoreductase

  Catalysed by PM20D1, ALOX12cytosolOne of 4 routes

• 15(S)-HPETEReach 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 15-oxidoreductase

  Catalysed by PM20D1, ALOX15B, ALOX15cytosolOne of 4 routes

• 5(S)-HPETEReach 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 5-oxidoreductase

  Catalysed by PM20D1, ALOX5cytosol

• (6R)-5,10-methylene-5,6,7,8-tetrahydrofolateReach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. (6R)-5,10-methylene-5,6,7,8-tetrahydrofolate + glycine + H2O = (6S)-5,6,7,8-tetrahydrofolate + L-serine
  3. (6R)-5,10-methylene-5,6,7,8-tetrahydrofolate + glycine + H2O = (6S)-5,6,7,8-tetrahydrofolate + L-serine

  Catalysed by SLC7A5, SHMT1, SHMT2extracellular space, cytosolOne of 2 routes

• 10-formyltetrahydrofolic acidReach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. 5,10-Methylenetetrahydrofolate:glycine hydroxymethyltransferase
  3. Formate:tetrahydrofolate ligase (ADP-forming)

  Catalysed by SLC7A5, SHMT1, MTHFD1extracellular space, cytosolOne of 5 routes

• 5-methyltetrahydrofolic acidReach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. 5,10-Methylenetetrahydrofolate:glycine hydroxymethyltransferase
  3. histamine N-methyltransferase (SAM)

  Catalysed by SLC7A5, SHMT1, HNMTextracellular space, cytosol

• CHEBI:15650Reach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. N-acetyl-LTE4 to leukotriene E4 conversion

  Catalysed by SLC7A5, BAAT, ZDHHC11B, NAA10 and 30 moreextracellular space, cytosol, peroxisomeOne of 6 routes

• betaine aldehydeReach from here →
  1. transport of cysteine and phenylalanine (cytosol to extracellular)
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. choline + A = betaine aldehyde + AH2

  Catalysed by SLC7A5, MOCOS, CHDHextracellular space, cytosolOne of 4 routes

• formateReach from here →
  1. transport of phenylalanine and tryptophan (cytosol to extracellular)
  2. L-tryptophan + O2 = N-formyl-L-kynurenine
  3. N-formyl-L-kynurenine + H2O = L-kynurenine + formate + H(+)

  Catalysed by SLC7A5, IDO1, TDO2, IDO2 and 1 moreextracellular space, cytosol

• CHEBI:15746Reach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. diamine N-acetyltransferase (N1-acetylspermine)

  Catalysed by SLC7A5, BAAT, SAT1, SAT2extracellular space, cytosol, peroxisomeOne of 2 routes

• hexadecanoic acidReach from here →
  1. Transport of L-Phenylalanine by Atb0 Transporter
  2. Carnitine Transport by Atb0
  3. Utilized Transport

  Catalysed by SLC6A14extracellular space, cytosol, endoplasmic reticulumOne of 2 routes

• 4-(2-amino-3-hydroxyphenyl)-2,4-dioxobutanoateReach from here →
  1. transport of phenylalanine and tryptophan (cytosol to extracellular)
  2. Transport of 3-Hydroxy-L-Kynurenine
  3. 3-hydroxy-L-kynurenine:2-oxoglutarate aminotransferase

  Catalysed by SLC7A5, KYAT1, KYAT3, AADATextracellular space, cytosol

• malonateReach from here →
  1. Transport of L-Phenylalanine by Atb0 Transporter
  2. transport of chloride and sulfate (cytosol to extracellular)
  3. malonate(in) + sulfate(out) = malonate(out) + sulfate(in)

  Catalysed by SLC6A14, SLC26A6, SLC25A14, SLC25A30 and 1 moreextracellular space, cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• 3-hydroxyanthranilic acidReach from here →
  1. transport of phenylalanine and tryptophan (cytosol to extracellular)
  2. Transport of 3-Hydroxy-L-Kynurenine
  3. 3-Hydroxy-L-kynurenine hydrolase

  Catalysed by SLC7A5, KYNUextracellular space, cytosol

• bromideReach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. 2-bromoacetaldehyde:glutathione S-(formylmethyl)transferase

  Catalysed by SLC7A5, GSS, MGST3, GSTA4 and 15 moreextracellular space, cytosolOne of 2 routes

• keto-D-fructose 6-phosphateReach from here →
  1. transport of glutamine and phenylalanine (cytosol to extracellular)
  2. L-glutamine:D-fructose-6-phosphate isomerase (deaminating)
  3. D-glucosamine-6-phosphate aminohydrolase (ketol isomerizing)

  Catalysed by SLC7A5, GFPT2, GFPT1, GNPDA1 and 1 moreextracellular space, cytosol

• N-acetyl-beta-D-glucosaminylamineReach from here →
  1. L-aspartate(in) + L-phenylalanine(out) = L-aspartate(out) + L-phenylalanine(in)
  2. N(4)-(beta-N-acetyl-D-glucosaminyl)-L-asparagine + H2O = N-acetyl-beta-D-glucosaminylamine + L-aspartate + H(+)
  3. N(4)-(beta-N-acetyl-D-glucosaminyl)-L-asparagine + H2O = N-acetyl-beta-D-glucosaminylamine + L-aspartate + H(+)

  Catalysed by SLC7A13, AGAinner side of the membrane, outer side of the membrane

• methanethiolReach from here →
  1. transport of cysteine and phenylalanine (cytosol to extracellular)
  2. L-cysteine hydrogen-sulfide-lyase (deaminating
  3. methanethiol + O2 + H2O = hydrogen sulfide + formaldehyde + H2O2 + H(+)

  Catalysed by SLC7A5, CTH, SELENBP1extracellular space, cytosol

• a halide anionReach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. gamma-L-glutamyl-L-cysteine + glycine + ATP = glutathione + ADP + phosphate + H(+)
  3. RX + glutathione = an S-substituted glutathione + a halide anion + H(+)

  Catalysed by SLC7A5, GSS, GSTT4, GSTA4 and 21 moreextracellular space, cytosol

• CHEBI:16132Reach from here →
  1. transport of phenylalanine and threonine (cytosol to extracellular)
  2. L-threonine acetaldehyde-lyase (glycine-forming)
  3. deoxyribose-phosphate aldolase

  Catalysed by SLC7A5, DERAextracellular space, cytosol

• homogentisateReach from here →
  1. transport of phenylalanine and tyrosine (cytosol to extracellular)
  2. L-tyrosine:2-oxoglutarate aminotransferase
  3. 4-Hydroxyphenylpyruvate:oxygen oxidoreductase (hydroxylating,decarboxylating)

  Catalysed by SLC7A5, GOT2, GOT1, TAT and 1 moreextracellular space, cytosolOne of 2 routes

• CHEBI:16174Reach from here →
  1. L-Phenylalanine:tRNA(Ala) ligase (AMP-forming)
  2. glycyl-tRNA(gly) phosphorylation
  3. 2'-deoxyadenosine 5'-diphosphate:oxidized-thioredoxin 2'-oxidoreductase

  Catalysed by FARSB, FARSA, TXN, RRM1 and 3 morecytosol

• 2-methyl-3-oxopropanoic acidReach from here →
  1. transport of alanine and phenylalanine (cytosol to extracellular)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. (S)-3-amino-2-methylpropionate transaminase (2-methyl-3-oxopropanoate)

  Catalysed by SLC7A5, AGXT2, ABATextracellular space, cytosol, mitochondrial matrixOne of 3 routes

• succinic semialdehydeReach from here →
  1. Transport of L-Phenylalanine by Atb0 Transporter
  2. transport of 4-aminobutyrate and chloride (cytosol to extracellular)
  3. 4-aminobutanoate:2-oxoglutarate aminotransferase

  Catalysed by SLC6A14, SLC6A12, ABATextracellular space, cytosol, mitochondrial matrix

• CHEBI:16284Reach from here →
  1. L-Phenylalanine:tRNA(Ala) ligase (AMP-forming)
  2. glycyl-tRNA(gly) phosphorylation
  3. 2'-deoxyadenosine 5'-triphosphate:oxydized-thioredoxin 2'-oxidoreductase

  Catalysed by FARSB, FARSA, TXN, RRM1 and 3 morecytosol

• nitriteReach from here →
  1. transport of arginine and phenylalanine (cytosol to extracellular)
  2. L-Arginine, NADPH:Oxygen Oxidoreductase (Nitric-Oxide-Forming)
  3. 4 nitric oxide + O2 + 2 H2O = 4 nitrite + 4 H(+)

  Catalysed by SLC7A6, NOS3, NOS1, NOS2 and 1 moreextracellular space, cytosol

• 11-cis-retinolReach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Palmitoyl-CoA:retinol O-acyltransferase

  Catalysed by SLC7A5, BAAT, DGAT1, LRAT and 3 moreextracellular space, cytosol, peroxisome