CHEBI:17203

Three steps

• (17Z)-hexacosenoyl-CoAReach from here →
  1. transport of alanine and proline (cytosol to extracellular)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. long-chain-fatty-acid-CoA ligase (ximenic acid)

  Catalysed by SLC7A5, SLC27A2, ACSL4, ACSL3 and 5 moreextracellular space, cytosol, mitochondrial matrixOne of 4 routes

• (8Z,11Z,14Z)-eicosatrienoyl-CoAReach from here →
  1. transport of alanine and proline (cytosol to extracellular)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)

  Catalysed by SLC7A5, SLC27A2, ACSL4, ACSL3 and 5 moreextracellular space, cytosol, mitochondrial matrixOne of 5 routes

• (8Z,11Z,14Z,17Z)-eicosatetraenoyl-CoAReach from here →
  1. transport of alanine and proline (cytosol to extracellular)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. long-chain-fatty-acid-CoA ligase (omega-3-arachidonic acid)

  Catalysed by SLC7A5, SLC27A2, ACSL4, ACSL3 and 5 moreextracellular space, cytosol, mitochondrial matrixOne of 5 routes

• (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoAReach from here →
  1. transport of alanine and proline (cytosol to extracellular)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. long-chain-fatty-acid-CoA ligase (DHA)

  Catalysed by SLC7A5, SLC27A2, ACSL4, ACSL3 and 5 moreextracellular space, cytosol, mitochondrial matrixOne of 7 routes

• heptadecanoyl-CoAReach from here →
  1. transport of alanine and proline (cytosol to extracellular)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. long-chain-fatty-acid-CoA ligase (margaric acid)

  Catalysed by SLC7A5, SLC27A2, ACSL4, ACSL3 and 5 moreextracellular space, cytosol, mitochondrial matrixOne of 6 routes

• (9Z)-heptadecenoyl-CoAReach from here →
  1. transport of alanine and proline (cytosol to extracellular)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. long-chain-fatty-acid-CoA ligase (9-heptadecylenic acid)

  Catalysed by SLC7A5, SLC27A2, ACSL4, ACSL3 and 5 moreextracellular space, cytosol, mitochondrial matrixOne of 5 routes

• (11Z,14Z,17Z)-eicosatrienoyl-CoAReach from here →
  1. transport of alanine and proline (cytosol to extracellular)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. long-chain-fatty-acid-CoA ligase ((11Z,14Z,17Z)-eicosatrienoic acid)

  Catalysed by SLC7A5, SLC27A2, ACSL4, ACSL3 and 5 moreextracellular space, cytosol, mitochondrial matrixOne of 5 routes

• nonadecanoyl-CoAReach from here →
  1. transport of alanine and proline (cytosol to extracellular)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. long-chain-fatty-acid-CoA ligase (nonadecylic acid)

  Catalysed by SLC7A5, SLC27A2, ACSL4, ACSL3 and 5 moreextracellular space, cytosol, mitochondrial matrixOne of 6 routes

• (11Z)-octadecenoyl-CoAReach from here →
  1. transport of alanine and proline (cytosol to extracellular)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix

  Catalysed by SLC7A5, CPT1A, CPT1C, CPT1Bextracellular space, cytosol, mitochondrial matrixOne of 3 routes

• dodecanedioyl-CoAReach from here →
  1. transport of alanine and proline (cytosol to extracellular)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. Activation of dodecanedioic acid

  Catalysed by SLC7A5extracellular space, cytosol, mitochondrial matrixOne of 4 routes

• decanedioyl-CoAReach from here →
  1. transport of alanine and proline (cytosol to extracellular)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. Production of Sebacoylcarnitine

  Catalysed by SLC7A5, CPT1A, CPT1C, CPT1Bextracellular space, cytosol, mitochondrial matrixOne of 4 routes

• octanedioyl-CoAReach from here →
  1. transport of alanine and proline (cytosol to extracellular)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. Production of Suberylcarnitine

  Catalysed by SLC7A5, CPT1A, CPT1C, CPT1Bextracellular space, cytosol, mitochondrial matrixOne of 4 routes

• hexanedioyl-CoAReach from here →
  1. transport of alanine and proline (cytosol to extracellular)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. Activation of adipic acid for Formation of Adipoyl Carnitine

  Catalysed by SLC7A5extracellular space, cytosol, mitochondrial matrixOne of 4 routes

• (4Z,7Z,10Z,13Z,16Z)-docosapentaenoyl-CoAReach from here →
  1. transport of alanine and proline (cytosol to extracellular)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. long-chain-fatty-acid-CoA ligase ((4Z,7Z,10Z,13Z,16Z)-DPA)

  Catalysed by SLC7A5, SLC27A2, ACSL4, ACSL3 and 5 moreextracellular space, cytosol, mitochondrial matrixOne of 7 routes

• (11Z,14Z)-eicosadienoyl-CoAReach from here →
  1. transport of alanine and proline (cytosol to extracellular)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. long-chain-fatty-acid-CoA ligase ((11Z,14Z)-eicosadienoic acid)

  Catalysed by SLC7A5, SLC27A2, ACSL4, ACSL3 and 5 moreextracellular space, cytosol, mitochondrial matrixOne of 5 routes

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

  Catalysed by SDS, SDSL, RIDAextracellular space, cytosol

• (R)-3-hydroxy-(11Z)-octadecenoyl-CoAReach from here →
  1. transport of alanine and proline (cytosol to extracellular)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. Production of 3-Hydroxyoctadecenoylcarnitinec

  Catalysed by SLC7A5, CPT1A, CPT1C, CPT1Bextracellular space, cytosol, mitochondrial matrix

• (13Z)-eicosenoyl-CoAReach from here →
  1. transport of alanine and proline (cytosol to extracellular)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. long-chain-fatty-acid-CoA ligase ((13Z)-eicosenoic acid)

  Catalysed by SLC7A5, SLC27A2, ACSL4, ACSL3 and 5 moreextracellular space, cytosol, mitochondrial matrixOne of 5 routes

• 2-aminoprop-2-enoateReach from here →
  1. transport of alanine and proline (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 cysteine and proline (cytosol to extracellular)
  2. cystine to cysteine conversion
  3. Resistance-Nodulation-Cell Division (Rnd) Tcdb:2.A.60.1.2

  Catalysed by SLC7A5, SLCO2A1extracellular space, cytosolOne of 2 routes

• N-acetyl-L-aspartyl-L-glutamateReach from here →
  1. Aspartate Intake by System Asct-1 Transporter
  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 NAT8L, RIMKLA, RIMKLBextracellular space, cytosol, mitochondrial matrix

• N-acetyl-L-aspartyl-L-glutamyl-L-glutamateReach from here →
  1. Aspartate Intake by System Asct-1 Transporter
  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 NAT8L, RIMKLAextracellular space, cytosol, mitochondrial matrix

• 4,8-dimethylnonanoyl-CoAReach from here →
  1. transport of alanine and proline (cytosol to extracellular)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. Carnitine Dimethyl Nonanoyl Transferase, Revsible, Peroxisomal

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

• tetradecanedioyl-CoAReach from here →
  1. transport of alanine and proline (cytosol to extracellular)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. Fatty Acid Beta Oxidation (C16Dc->C14Dc), Peroxisomal

  Catalysed by SLC7A5, ACAA1, HSD17B4, EHHADH and 1 moreextracellular space, cytosol, mitochondrial matrix, peroxisome

• hexadecanedioyl-CoAReach from here →
  1. transport of alanine and proline (cytosol to extracellular)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. Production of Hexadecanedioylcarnitine

  Catalysed by SLC7A5, CPT1A, CPT1C, CPT1Bextracellular space, cytosol, mitochondrial matrixOne of 2 routes

• O-dodecanoyl-R-carnitineReach from here →
  1. Transport of L-Proline by the Apical Imino Amino Acid Transporters
  2. Carnitine Transport by Atb0
  3. carnitine O-palmitoyltransferase (dodecanoylcarnitine)

  Catalysed by CLTRN, SLC6A20, SLC6A14, CPT1A and 2 moreextracellular space, cytosolOne of 7 routes

• pristanoyl-CoAReach from here →
  1. transport of alanine and proline (cytosol to extracellular)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. fatty-acid-CoA ligase

  Catalysed by SLC7A5, SLC27A2extracellular space, cytosol, mitochondrial matrixOne of 2 routes

• undecanoyl-CoAReach from here →
  1. transport of alanine and proline (cytosol to extracellular)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. medium-chain acyl-CoA ligase (undecylic acid)

  Catalysed by SLC7A5, ACSM4, ACSM1, ACSM2A and 3 moreextracellular space, cytosol, mitochondrial matrixOne of 3 routes

• a fatty acyl-CoAReach from here →
  1. transport of glycine and proline (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, SLC7A6, GLYATL2extracellular space, cytosol

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

  Catalysed by SLC7A5, MOCOS, PTGS1, PTGS2extracellular space, cytosolOne of 2 routes

• (9R)-hydroxy-(10E,12Z)-octadecadienoateReach from here →
  1. transport of alanine and proline (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

• ursodeoxycholateReach from here →
  1. transport of cysteine and proline (cytosol to extracellular)
  2. cystine to cysteine conversion
  3. transport of GSH and ursodeoxycholate (cytosol to extracellular)

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

• (11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoateReach from here →
  1. transport of alanine and proline (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, cytosol

• (15R)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. transport of alanine and proline (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, cytosol

• 3-phenyllactateReach from here →
  1. transport of phenylalanine and proline (cytosol to extracellular)
  2. Phenylalanine Transaminase, Mitochondrial
  3. Formation of Phenyl-Lactate

  Catalysed by SLC7A5, GOT2, TATextracellular space, cytosol, mitochondrial matrix

• prostaglandin G2Reach from here →
  1. transport of cysteine and proline (cytosol to extracellular)
  2. cystine to cysteine conversion
  3. transport of GSH and prostaglandin G2 (cytosol to extracellular)

  Catalysed by SLC7A5, SLCO2A1extracellular space, cytosolOne of 2 routes

• (12R)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoateReach from here →
  1. transport of glycine and proline (cytosol to extracellular)
  2. gamma-L-glutamyl-L-cysteine + glycine + ATP = glutathione + ADP + phosphate + H(+)
  3. (12R)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate + 2 glutathione = (12R)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoate + glutathione disulfide + H2O

  Catalysed by SLC7A5, SLC7A6, GSS, GPX1 and 2 moreextracellular space, cytosol

• (5Z)-tetradecenoyl-CoAReach from here →
  1. transport of alanine and proline (cytosol to extracellular)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. long-chain-fatty-acid-CoA ligase (physeteric acid)

  Catalysed by SLC7A5, SLC27A2, ACSL4, ACSL3 and 5 moreextracellular space, cytosol, mitochondrial matrixOne of 8 routes

• O-4,8-dimethylnonanoyl-(R)-carnitineReach from here →
  1. Transport of L-Proline by the Apical Imino Amino Acid Transporters
  2. Carnitine Transport by Atb0
  3. Carnitine Dimethyl Nonanoyl Transferase, Revsible, Peroxisomal

  Catalysed by CLTRN, SLC6A20, SLC6A14, CRAT and 1 moreextracellular space, cytosol, peroxisomeOne of 5 routes

• (3E)-decenoyl-CoAReach from here →
  1. transport of alanine and proline (cytosol to extracellular)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. Fatty Acid Beta Oxidation (C12:1->C10:1), Mitochondrial

  Catalysed by SLC7A5, ACADM, ECHS1, ACAA2 and 1 moreextracellular space, cytosol, mitochondrial matrix

• 2-glyceryl-prostaglandin H2Reach from here →
  1. transport of alanine and proline (cytosol to extracellular)
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. 2-glyceryl-prostaglandin G2 + AH2 = 2-glyceryl-prostaglandin H2 + A + H2O

  Catalysed by SLC7A5, MOCOS, PTGS2extracellular space, cytosol

• (2R,6)-dimethylheptanoyl-CoAReach from here →
  1. transport of alanine and proline (cytosol to extracellular)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. acetyl-CoA C-acyltransferase (3-oxo-4(R),8-dimethyl-nonanoyl-CoA)

  Catalysed by SLC7A5, HADHA, ACAA2, HADHBextracellular space, cytosol, mitochondrial matrix

• (7Z)-hexadecenoyl-CoAReach from here →
  1. transport of alanine and proline (cytosol to extracellular)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. long-chain-fatty-acid-CoA ligase (7-palmitoleic acid)

  Catalysed by SLC7A5, SLC27A2, ACSL4, ACSL3 and 5 moreextracellular space, cytosol, mitochondrial matrixOne of 8 routes

• 3-methylmalateReach from here →
  1. transport of glycine and proline (cytosol to extracellular)
  2. glycine + 2-oxoglutarate = glyoxylate + L-glutamate
  3. propanoyl-CoA + glyoxylate + H2O = 3-methylmalate + CoA + H(+)

  Catalysed by SLC7A5, SLC7A6, AADAT, CLYBLextracellular space, cytosol

• tricosanoyl-CoAReach from here →
  1. transport of alanine and proline (cytosol to extracellular)
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. long-chain-fatty-acid-CoA ligase (tricosanoic acid)

  Catalysed by SLC7A5, SLC27A2, ACSL4, ACSL3 and 5 moreextracellular space, cytosol, mitochondrial matrixOne of 4 routes

• (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of glycine and proline (cytosol to extracellular)
  2. gamma-L-glutamyl-L-cysteine + glycine + ATP = glutathione + ADP + phosphate + H(+)
  3. (5S)-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + 2 glutathione = (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + glutathione disulfide + H2O

  Catalysed by SLC7A5, SLC7A6, GSS, PTGES and 5 moreextracellular space, cytosol

• Se-methylselenocysteineReach from here →
  1. transport of alanine and proline (cytosol to extracellular)
  2. L-selenocysteine selenide-lyase (L-alanine-forming)
  3. S-Adenosyl-L-methionine:thiol S-methyltransferase

  Catalysed by SLC7A5, SCLYextracellular space, cytosol

• (12S)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoateReach from here →
  1. transport of glycine and proline (cytosol to extracellular)
  2. gamma-L-glutamyl-L-cysteine + glycine + ATP = glutathione + ADP + phosphate + H(+)
  3. (12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate + 2 glutathione = (12S)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoate + glutathione disulfide + H2O

  Catalysed by SLC7A5, SLC7A6, GSS, GPX1 and 1 moreextracellular space, cytosol

• thromboxane B2Reach from here →
  1. transport of cysteine and proline (cytosol to extracellular)
  2. cystine to cysteine conversion
  3. transport of GSH and thromboxane B2 (cytosol to extracellular)

  Catalysed by SLC7A5, SLCO1B1extracellular space, cytosolOne of 2 routes

• an S-substituted glutathioneReach from here →
  1. transport of glycine and proline (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, SLC7A6, GSS, GSTT4 and 22 moreextracellular space, cytosolOne of 2 routes