L-phenylalanine

Three steps

• (3S)-citramalyl-CoAReach from here →
  1. transport of alanine and phenylalanine (cytosol to extracellular)
  2. (R)-3-Amino-2-methylpropanoate:pyruvate aminotransferase
  3. (3S)-citramalyl-CoA = pyruvate + acetyl-CoA

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

• (25R)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oyl-CoAReach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. 3alpha,7alpha,12alpha-trihydroxy-5beta-cholestanoate:CoA ligase (AMP-forming)

  Catalysed by SLC7A5, BAAT, SLC27A2, SLC27A5extracellular space, cytosol, peroxisome, endoplasmic reticulumOne of 3 routes

• phosphoenolpyruvateReach from here →
  1. L-aspartate(in) + L-phenylalanine(out) = L-aspartate(out) + L-phenylalanine(in)
  2. L-Aspartate:2-oxoglutarate aminotransferase
  3. oxaloacetate + GTP = phosphoenolpyruvate + GDP + CO2

  Catalysed by SLC7A13, GOT2, PCK1, PCK2inner side of the membrane, outer side of the membrane, mitochondrial matrix

• deoxycholoyl-CoAReach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. cholate-CoA ligase (3alpha,12alpha-dihydroxy-5beta-cholanate)

  Catalysed by SLC7A5, BAAT, SLC27A2, SLC27A5extracellular space, cytosol, peroxisomeOne of 4 routes

• S-sulfanylglutathioneReach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. Sulfide:glutathione,quinone oxidoreductase

  Catalysed by SLC7A5, GSS, SQORextracellular space, cytosol, mitochondrial matrixOne of 8 routes

• methylamineReach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. N(omega)-methyl-L-arginine + glyoxylate = 5-(3-methylguanidino)-2-oxopentanoate + glycine
  3. N(omega)-methyl-L-arginine + H2O = L-citrulline + methylamine

  Catalysed by SLC7A5, AGXT2, DDAH1extracellular space, cytosol

• monodehydro-L-ascorbate radicalReach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. (9Z)-octadecenoyl-CoA + glycine = N-(9Z-octadecenoyl)glycine + CoA + H(+)
  3. N-(9Z-octadecenoyl)glycine + 2 L-ascorbate + O2 = N-(9Z-octadecenoyl)-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O

  Catalysed by SLC7A5, GLYATL3, GLYATL2, PAMextracellular space, cytosolOne of 6 routes

• pyridoxal 5'-phosphateReach from here →
  1. transport of alanine and phenylalanine (cytosol to extracellular)
  2. L-selenocysteine selenide-lyase (L-alanine-forming)
  3. pyridoxine 5'-phosphate + O2 = pyridoxal 5'-phosphate + H2O2

  Catalysed by SLC7A5, SCLY, PNPOextracellular space, cytosol

• 2-hydroxy-4-methylvaleric acidReach from here →
  1. transport of leucine and phenylalanine (cytosol to extracellular)
  2. L-Leucine:2-oxoglutarate aminotransferase
  3. 4-methyl-2-oxopentanoate reduction

  Catalysed by SLC7A5, BCAT2, SDR42E2, AKR1B15 and 16 moreextracellular space, cytosol, mitochondrial matrix

• an N-acyl-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 N-acyl-L-amino acid + H2O = an L-alpha-amino acid + a carboxylate

  Catalysed by SLC7A8, SLC7A11, ACY1, PM20D1extracellular space, cytosol, inner side of the membrane, outer side of the membrane

• (2S)-2-phospholactateReach from here →
  1. (S)-lactate + L-phenylalanine = N-[(S)-lactoyl]-L-phenylalanine + H2O
  2. (S)-lactate + L-phenylalanine = N-[(S)-lactoyl]-L-phenylalanine + H2O
  3. (2S)-2-phospholactate + H2O = (S)-lactate + phosphate

  Catalysed by CNDP2, PGPOne of 2 routes

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

  Catalysed by SLC7A5, BAAT, SULT2A1extracellular space, cytosolOne of 3 routes

• a 2,3-dehydroacyl-CoAReach 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. a 2,3-saturated acyl-CoA + A = a 2,3-dehydroacyl-CoA + AH2

  Catalysed by SLC7A5, MOCOS, ACAD10extracellular space, cytosol

• estrone 3-sulfateReach from here →
  1. Transport of L-Phenylalanine by Atb0 Transporter
  2. transport of chloride and sulfate (cytosol to extracellular)
  3. estrone 3-sulfate + H2O = estrone + sulfate + H(+)

  Catalysed by SLC6A14, SLC26A6, STSextracellular space, cytosol

• prostaglandin E2Reach 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 E2 (cytosol to extracellular)

  Catalysed by SLC7A5, GSS, SLCO1A2, SLCO1B3extracellular space, cytosolOne of 4 routes

• decanoyl-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 (decanoic acid)

  Catalysed by SLC7A5, BAAT, ACSM4, ACSM1 and 4 moreextracellular space, cytosol, peroxisomeOne of 8 routes

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

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

• (2E)-hexadecenoyl-CoAReach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Carnitine O-Palmitoyltransferase

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

• (9Z)-hexadecenoyl-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 (palmitolate)

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

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

  Catalysed by FARSB, FARSA, TXN, RRM1 and 3 morecytosolOne of 3 routes

• Fe(II)-heme aReach 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. Fe(II)-heme o + 2 A + H2O = Fe(II)-heme a + 2 AH2

  Catalysed by SLC7A5, MOCOS, COX15extracellular space, cytosol

• (R)-4'-phosphopantetheineReach from here →
  1. transport of cysteine and phenylalanine (cytosol to extracellular)
  2. (R)-4'-phosphopantothenate:L-cysteine ligase
  3. N-[(R)-4-phosphopantothenoyl]-L-cysteine + H(+) = (R)-4'-phosphopantetheine + CO2

  Catalysed by SLC7A5, PPCS, PPCDCextracellular space, cytosol

• (4R)-4-hydroxy-2-oxoglutarateReach from here →
  1. Phenylalanine Transaminase, Mitochondrial
  2. glyoxylate + L-phenylalanine = 3-phenylpyruvate + glycine
  3. (4R)-4-hydroxy-2-oxoglutarate = glyoxylate + pyruvate

  Catalysed by GOT2, TAT, AADAT, HOGA1mitochondrial matrixOne of 2 routes

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

  Catalysed by SLC7A5, BAAT, CPT1A, CPT1Bextracellular space, cytosol, peroxisome

• (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylateReach from here →
  1. transport of alanine and phenylalanine (cytosol to extracellular)
  2. Transport of Hydroxy-Proline
  3. trans-4-Hydroxy-L-proline:NAD+ 5-oxidoreductase

  Catalysed by SLC7A5, SLC1A4, PYCR1, PYCR3 and 1 moreextracellular space, cytosolOne of 5 routes

• (5-hydroxyindol-3-yl)acetateReach from here →
  1. Transport of L-Phenylalanine by Atb0 Transporter
  2. transport of chloride and sulfate (cytosol to extracellular)
  3. Transport of 5-Hydroxyindoleacetate

  Catalysed by SLC6A14, SLC26A6, SLC4A1extracellular space, cytosolOne of 2 routes

• 2-deoxy-D-ribose 5-phosphateReach from here →
  1. transport of phenylalanine and threonine (cytosol to extracellular)
  2. L-threonine acetaldehyde-lyase (glycine-forming)
  3. 2-deoxy-D-ribose 5-phosphate = D-glyceraldehyde 3-phosphate + acetaldehyde

  Catalysed by SLC7A5, DERAextracellular space, cytosol

• leukotriene D4Reach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. leukotriene C4 hydrolysis
  3. leukotriene C4 + H2O = leukotriene D4 + L-glutamate

  Catalysed by SLC7A5, GGT1, GGT5extracellular space, cytosol

• CHEBI:63544Reach 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 (adrenic acid)

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

• 18-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. cytochrome P450 (arachidonate)

  Catalysed by PM20D1, CYP4F8endoplasmic reticulumOne of 2 routes

• ubiquinol-10Reach from here →
  1. transport of glycine and phenylalanine (cytosol to extracellular)
  2. gamma-L-glutamyl-L-cysteine + glycine + ATP = glutathione + ADP + phosphate + H(+)
  3. ubiquinone-10 + hydrogen sulfide + glutathione + H(+) = S-sulfanylglutathione + ubiquinol-10

  Catalysed by SLC7A5, GSS, SQORextracellular space, cytosolOne of 3 routes

• hexacosanoyl-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 (cerotic acid)

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

• tetracosanoyl-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 (lignocerate)

  Catalysed by SLC7A5, BAAT, SLC27A2, ACSL4 and 6 moreextracellular space, cytosol, peroxisomeOne of 10 routes

• docosanoyl-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 (behenic acid)

  Catalysed by SLC7A5, BAAT, SLC27A2, ACSL4 and 6 moreextracellular space, cytosol, peroxisomeOne of 9 routes

• a 2,3-saturated acyl-CoAReach 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. a 2,3-saturated acyl-CoA + A = a 2,3-dehydroacyl-CoA + AH2

  Catalysed by SLC7A5, MOCOS, ACAD10extracellular space, cytosol

• xanthurenateReach from here →
  1. Phenylalanine Transaminase, Mitochondrial
  2. glyoxylate + L-phenylalanine = 3-phenylpyruvate + glycine
  3. 3-hydroxy-L-kynurenine + glyoxylate = xanthurenate + glycine + H2O

  Catalysed by GOT2, TAT, AADAT, KYAT3mitochondrial matrixOne of 4 routes

• (2E)-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

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

• (6Z,9Z,12Z,15Z)-octadecatetraenoyl-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 (stearidonic acid)

  Catalysed by SLC7A5, BAAT, SLC27A2, ACSL4 and 6 moreextracellular space, cytosol, peroxisomeOne of 8 routes

• (8Z,11Z,14Z)-eicosatrienoateReach from here →
  1. Transport of L-Phenylalanine by Atb0 Transporter
  2. Carnitine Transport by Atb0
  3. Utilized Transport

  Catalysed by SLC6A14extracellular space, cytosol, endoplasmic reticulum

• (4S)-4-hydroxy-2-oxoglutarateReach from here →
  1. Phenylalanine Transaminase, Mitochondrial
  2. glyoxylate + L-phenylalanine = 3-phenylpyruvate + glycine
  3. (4S)-4-hydroxy-2-oxoglutarate = glyoxylate + pyruvate

  Catalysed by GOT2, TAT, AADAT, HOGA1mitochondrial matrixOne of 2 routes

• (R)-noradrenalineReach 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 noradrenaline (cytosol to extracellular)

  Catalysed by SLC7A5, GSS, SLCO1A2, SLCO1B3extracellular space, cytosolOne of 4 routes

• 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol)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-(1'-sn-glycerol) + H2O = sn-glycero-3-phospho-(1'-sn-glycerol) + (9Z)-octadecenoate + H(+)

  Catalysed by PM20D1, ABHD12

• 1-hexadecanoyl-2-(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-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1D-myo-inositol) + H2O = 1-hexadecanoyl-sn-glycero-3-phospho-(1D-myo-inositol) + (9Z)-octadecenoate + H(+)

  Catalysed by PM20D1, ABHD16A

• a 1-(1-hydroxyalkyl)-sn-glycerolReach from here →
  1. (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + L-phenylalanine + O2 = (4aS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterin + L-tyrosine
  2. (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + L-tryptophan + O2 = 5-hydroxy-L-tryptophan + (4aS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterin
  3. 1-O-(1,2-saturated-alkyl)-sn-glycerol + (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + O2 = a 1-(1-hydroxyalkyl)-sn-glycerol + (6R)-L-erythro-6,7-dihydrobiopterin + H2O

  Catalysed by PAH, TPH1, TPH2, AGMO

• L-threonylcarbamoyladenylateReach from here →
  1. transport of alanine and phenylalanine (cytosol to extracellular)
  2. L-threonine(out) + L-alanine(in) = L-threonine(in) + L-alanine(out)
  3. L-threonine + hydrogencarbonate + ATP = L-threonylcarbamoyladenylate + diphosphate + H2O

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

• (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-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 (EPA)

  Catalysed by SLC7A5, BAAT, SLC27A2, ACSL4 and 6 moreextracellular space, cytosol, peroxisomeOne of 9 routes

• (7Z,10Z,13Z,16Z,19Z)-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 (DPA)

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

• (9Z,12Z,15Z)-octadecatrienoyl-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 (linolenate)

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

• (13Z)-docosenoyl-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 (cis-erucic acid)

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

• (11Z)-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 (cis-gondoic acid)

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