CHEBI:15570

Three steps

• (11Z,14Z,17Z)-eicosatrienoyl-CoAReach from here →
  1. alanine racemase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. long-chain-fatty-acid-CoA ligase ((11Z,14Z,17Z)-eicosatrienoic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 4 morecytosol, mitochondrial matrixOne of 5 routes

• nonadecanoyl-CoAReach from here →
  1. alanine racemase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. long-chain-fatty-acid-CoA ligase (nonadecylic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 4 morecytosol, mitochondrial matrixOne of 6 routes

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

  Catalysed by CPT1A, CPT1C, CPT1Bcytosol, mitochondrial matrixOne of 3 routes

• dodecanedioyl-CoAReach from here →
  1. alanine racemase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. Activation of dodecanedioic acid

  No catalyst recordedcytosol, mitochondrial matrixOne of 4 routes

• decanedioyl-CoAReach from here →
  1. alanine racemase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. Production of Sebacoylcarnitine

  Catalysed by CPT1A, CPT1C, CPT1Bcytosol, mitochondrial matrixOne of 4 routes

• octanedioyl-CoAReach from here →
  1. alanine racemase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. Production of Suberylcarnitine

  Catalysed by CPT1A, CPT1C, CPT1Bcytosol, mitochondrial matrixOne of 4 routes

• hexanedioyl-CoAReach from here →
  1. alanine racemase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. Activation of adipic acid for Formation of Adipoyl Carnitine

  No catalyst recordedcytosol, mitochondrial matrixOne of 4 routes

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

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 4 morecytosol, mitochondrial matrixOne of 7 routes

• (11Z,14Z)-eicosadienoyl-CoAReach from here →
  1. alanine racemase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. long-chain-fatty-acid-CoA ligase ((11Z,14Z)-eicosadienoic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 4 morecytosol, mitochondrial matrixOne of 5 routes

• 2-iminobutanoateReach from here →
  1. D-alanine:oxygen oxidoreductase (deaminating)
  2. 2-oxobutanoate + L-alanine = (2S)-2-aminobutanoate + pyruvate
  3. 2-iminobutanoate + H2O = 2-oxobutanoate + NH4(+)

  Catalysed by DAO, AGXT2, RIDAperoxisome

• (R)-3-hydroxy-(11Z)-octadecenoyl-CoAReach from here →
  1. alanine racemase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. Production of 3-Hydroxyoctadecenoylcarnitinec

  Catalysed by CPT1A, CPT1C, CPT1Bcytosol, mitochondrial matrix

• (13Z)-eicosenoyl-CoAReach from here →
  1. alanine racemase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. long-chain-fatty-acid-CoA ligase ((13Z)-eicosenoic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 4 morecytosol, mitochondrial matrixOne of 5 routes

• 2-aminoprop-2-enoateReach from here →
  1. alanine racemase
  2. D-serine(out) + L-alanine(in) = D-serine(in) + L-alanine(out)
  3. D-serine = 2-aminoprop-2-enoate + H2O

  Catalysed by SLC7A10, SRRcytosol, inner side of the membrane, outer side of the membrane

• 20-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of D-alanine and glycine (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 SLC3A2, SLC7A10, GSS, SLCO2A1extracellular space, cytosolOne of 2 routes

• 4,8-dimethylnonanoyl-CoAReach from here →
  1. alanine racemase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. Carnitine Dimethyl Nonanoyl Transferase, Revsible, Peroxisomal

  Catalysed by CRAT, CROTcytosol, mitochondrial matrix, peroxisomeOne of 3 routes

• tetradecanedioyl-CoAReach from here →
  1. alanine racemase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. Fatty Acid Beta Oxidation (C16Dc->C14Dc), Peroxisomal

  Catalysed by ACAA1, HSD17B4, EHHADH, ACOX1cytosol, mitochondrial matrix, peroxisome

• hexadecanedioyl-CoAReach from here →
  1. alanine racemase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. Production of Hexadecanedioylcarnitine

  Catalysed by CPT1A, CPT1C, CPT1Bcytosol, mitochondrial matrixOne of 2 routes

• pristanoyl-CoAReach from here →
  1. alanine racemase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. fatty-acid-CoA ligase

  Catalysed by SLC27A2cytosol, mitochondrial matrixOne of 2 routes

• undecanoyl-CoAReach from here →
  1. alanine racemase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. medium-chain acyl-CoA ligase (undecylic acid)

  Catalysed by ACSM4, ACSM1, ACSM2A, ACSM3 and 2 morecytosol, mitochondrial matrixOne of 3 routes

• a fatty acyl-CoAReach from here →
  1. transport of D-alanine and glycine (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 SLC3A2, SLC7A10, GLYATL2extracellular space, cytosol

• (9S)-hydroxy-(10E,12Z)-octadecadienoateReach from here →
  1. alanine racemase
  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 MOCOS, PTGS1, PTGS2cytosolOne of 2 routes

• (9R)-hydroxy-(10E,12Z)-octadecadienoateReach from here →
  1. alanine racemase
  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 MOCOS, PTGS1, PTGS2cytosol

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

  Catalysed by SLC3A2, SLC7A10, GSS, SLCO1A2 and 1 moreextracellular space, cytosolOne of 2 routes

• (11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoateReach from here →
  1. alanine racemase
  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 MOCOS, PTGS2cytosol

• (15R)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. alanine racemase
  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 MOCOS, PTGS2cytosol

• prostaglandin G2Reach from here →
  1. transport of D-alanine and glycine (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 SLC3A2, SLC7A10, GSS, SLCO2A1extracellular space, cytosolOne of 2 routes

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

  Catalysed by SLC7A5, MOCOScytosol, extracellular spaceOne of 3 routes

• (12R)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoateReach from here →
  1. transport of D-alanine and glycine (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 SLC3A2, SLC7A10, GSS, GPX1 and 2 moreextracellular space, cytosol

• (5Z)-tetradecenoyl-CoAReach from here →
  1. alanine racemase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. long-chain-fatty-acid-CoA ligase (physeteric acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 4 morecytosol, mitochondrial matrixOne of 8 routes

• (3E)-decenoyl-CoAReach from here →
  1. alanine racemase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. Fatty Acid Beta Oxidation (C12:1->C10:1), Mitochondrial

  Catalysed by ACADM, ECHS1, ACAA2, HADHcytosol, mitochondrial matrix

• 2-glyceryl-prostaglandin H2Reach from here →
  1. alanine racemase
  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 MOCOS, PTGS2cytosol

• (2R,6)-dimethylheptanoyl-CoAReach from here →
  1. alanine racemase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. acetyl-CoA C-acyltransferase (3-oxo-4(R),8-dimethyl-nonanoyl-CoA)

  Catalysed by HADHA, ACAA2, HADHBcytosol, mitochondrial matrix

• (7Z)-hexadecenoyl-CoAReach from here →
  1. alanine racemase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. long-chain-fatty-acid-CoA ligase (7-palmitoleic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 4 morecytosol, mitochondrial matrixOne of 8 routes

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

  Catalysed by SLC3A2, SLC7A10, AADAT, CLYBLextracellular space, cytosol

• tricosanoyl-CoAReach from here →
  1. alanine racemase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. long-chain-fatty-acid-CoA ligase (tricosanoic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 4 morecytosol, mitochondrial matrixOne of 4 routes

• (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of D-alanine and glycine (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 SLC3A2, SLC7A10, GSS, PTGES and 5 moreextracellular space, cytosol

• Se-methylselenocysteineReach from here →
  1. alanine racemase
  2. L-selenocysteine selenide-lyase (L-alanine-forming)
  3. S-Adenosyl-L-methionine:thiol S-methyltransferase

  Catalysed by SCLYcytosol

• (12S)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoateReach from here →
  1. transport of D-alanine and glycine (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 SLC3A2, SLC7A10, GSS, GPX1 and 1 moreextracellular space, cytosol

• thromboxane B2Reach from here →
  1. transport of D-alanine and glycine (cytosol to extracellular)
  2. gamma-L-glutamyl-L-cysteine:glycine ligase (ADP-forming)
  3. transport of GSH and thromboxane B2 (cytosol to extracellular)

  Catalysed by SLC3A2, SLC7A10, GSS, SLCO1B1extracellular space, cytosolOne of 4 routes

• an S-substituted glutathioneReach from here →
  1. transport of D-alanine and glycine (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 SLC3A2, SLC7A10, GSS, GSTT4 and 22 moreextracellular space, cytosolOne of 2 routes

• prostaglandin H1Reach from here →
  1. alanine racemase
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. prostaglandin G1 + AH2 = prostaglandin H1 + A + H2O

  Catalysed by MOCOS, PTGS2cytosol

• (5S,11R)-dihydroxy-(6E,8Z,12E,14Z)-eicosatetraenoateReach from here →
  1. alanine racemase
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (5S,11R)-dihydroxy-(6E,8Z,12E,14Z)-eicosatetraenoate + A + H2O

  Catalysed by MOCOS, PTGS2cytosol

• (5S,15R)-dihydroxy-(6E,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. alanine racemase
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (5S,15R)-dihydroxy-(6E,8Z,11Z,13E)-eicosatetraenoate + A + H2O

  Catalysed by MOCOS, PTGS2cytosol

• (5S,15S)-dihydroxy-(6E,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. alanine racemase
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (5S,15S)-dihydroxy-(6E,8Z,11Z,13E)-eicosatetraenoate + A + H2O

  Catalysed by MOCOS, PTGS2cytosol

• 17R-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoateReach from here →
  1. alanine racemase
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + AH2 + O2 = 17R-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate + A + H2O

  Catalysed by MOCOS, PTGS2cytosol

• 13-hydroxy-(4Z,7Z,10Z,14E,16Z,19Z)-docosahexaenoateReach from here →
  1. alanine racemase
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + AH2 + O2 = 13-hydroxy-(4Z,7Z,10Z,14E,16Z,19Z)-docosahexaenoate + A + H2O

  Catalysed by MOCOS, PTGS2cytosol

• (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoateReach from here →
  1. alanine racemase
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O

  Catalysed by MOCOS, PTGS2cytosol

• (15R)-hydroxy-(5Z,8Z,11Z,13E,17Z)-eicosapentaenoateReach from here →
  1. alanine racemase
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (15R)-hydroxy-(5Z,8Z,11Z,13E,17Z)-eicosapentaenoate + A + H2O

  Catalysed by MOCOS, PTGS2cytosol

• (11R)-hydroxy-(5Z,8Z,12E,14Z,17Z)-eicosapentaenoateReach from here →
  1. alanine racemase
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (11R)-hydroxy-(5Z,8Z,12E,14Z,17Z)-eicosapentaenoate + A + H2O

  Catalysed by MOCOS, PTGS2cytosol

• 13R-hydroxy-(7Z,10Z,14E,16Z,19Z)-docosapentaenoateReach from here →
  1. alanine racemase
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. (7Z,10Z,13Z,16Z,19Z)-docosapentaenoate + AH2 + O2 = 13R-hydroxy-(7Z,10Z,14E,16Z,19Z)-docosapentaenoate + A + H2O

  Catalysed by MOCOS, PTGS2cytosol