CHEBI:28666

Three steps

• heptadecanoyl-CoAReach from here →
  1. membrane dipeptidase (LTD4)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (margaric acid)

  Catalysed by DPEP1, DPEP2, BAAT, SLC27A2 and 7 moreextracellular space, peroxisome, cytosolOne of 6 routes

• (9Z)-heptadecenoyl-CoAReach from here →
  1. membrane dipeptidase (LTD4)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (9-heptadecylenic acid)

  Catalysed by DPEP1, DPEP2, BAAT, SLC27A2 and 7 moreextracellular space, peroxisome, cytosolOne of 5 routes

• (11Z,14Z,17Z)-eicosatrienoyl-CoAReach from here →
  1. membrane dipeptidase (LTD4)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase ((11Z,14Z,17Z)-eicosatrienoic acid)

  Catalysed by DPEP1, DPEP2, BAAT, SLC27A2 and 7 moreextracellular space, peroxisome, cytosolOne of 5 routes

• nonadecanoyl-CoAReach from here →
  1. membrane dipeptidase (LTD4)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (nonadecylic acid)

  Catalysed by DPEP1, DPEP2, BAAT, SLC27A2 and 7 moreextracellular space, peroxisome, cytosolOne of 6 routes

• (11Z)-octadecenoyl-CoAReach from here →
  1. membrane dipeptidase (LTD4)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix

  Catalysed by DPEP1, DPEP2, BAAT, CPT1A and 2 moreextracellular space, peroxisome, cytosolOne of 3 routes

• (12R)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoateReach from here →
  1. transport of LTD4 (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (12R)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate

  Catalysed by SLCO1B1, ALOX12Bextracellular space, cytosol

• (8S)-hydroperoxy-(5Z,9E,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of LTD4 (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. Arachidonate:oxygen 8-oxidoreductase

  Catalysed by SLCO1B1, ALOX12extracellular space, cytosolOne of 2 routes

• 2-O-(5Z,8Z,11Z,14Z)-eicosatetraenylglycerolReach from here →
  1. transport of LTD4 (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. fatty acid amide hydrolase (arachidonate)

  Catalysed by SLCO1B1, FAAHextracellular space, cytosol

• dodecanedioyl-CoAReach from here →
  1. membrane dipeptidase (LTD4)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Activation of dodecanedioic acid

  Catalysed by DPEP1, DPEP2, BAATextracellular space, peroxisome, cytosolOne of 4 routes

• decanedioyl-CoAReach from here →
  1. membrane dipeptidase (LTD4)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Production of Sebacoylcarnitine

  Catalysed by DPEP1, DPEP2, BAAT, CPT1A and 2 moreextracellular space, peroxisome, cytosolOne of 4 routes

• octanedioyl-CoAReach from here →
  1. membrane dipeptidase (LTD4)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Production of Suberylcarnitine

  Catalysed by DPEP1, DPEP2, BAAT, CPT1A and 2 moreextracellular space, peroxisome, cytosolOne of 4 routes

• hexanedioyl-CoAReach from here →
  1. membrane dipeptidase (LTD4)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Activation of adipic acid for Formation of Adipoyl Carnitine

  Catalysed by DPEP1, DPEP2, BAATextracellular space, peroxisome, cytosolOne of 4 routes

• (4Z,7Z,10Z,13Z,16Z)-docosapentaenoyl-CoAReach from here →
  1. membrane dipeptidase (LTD4)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase ((4Z,7Z,10Z,13Z,16Z)-DPA)

  Catalysed by DPEP1, DPEP2, BAAT, SLC27A2 and 7 moreextracellular space, peroxisome, cytosolOne of 7 routes

• (11Z,14Z)-eicosadienoyl-CoAReach from here →
  1. membrane dipeptidase (LTD4)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase ((11Z,14Z)-eicosadienoic acid)

  Catalysed by DPEP1, DPEP2, BAAT, SLC27A2 and 7 moreextracellular space, peroxisome, cytosolOne of 5 routes

• (R)-3-hydroxy-(11Z)-octadecenoyl-CoAReach from here →
  1. membrane dipeptidase (LTD4)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Production of 3-Hydroxyoctadecenoylcarnitinec

  Catalysed by DPEP1, DPEP2, BAAT, CPT1A and 2 moreextracellular space, peroxisome, cytosol

• (13Z)-eicosenoyl-CoAReach from here →
  1. membrane dipeptidase (LTD4)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase ((13Z)-eicosenoic acid)

  Catalysed by DPEP1, DPEP2, BAAT, SLC27A2 and 7 moreextracellular space, peroxisome, cytosolOne of 5 routes

• 11,12-epoxy-(5Z,8Z,14Z)-eicosatrienoateReach from here →
  1. transport of LTD4 (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  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 SLCO1B1, CYP2C9extracellular space, cytosol

• 19-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of LTD4 (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  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 SLCO1B1, CYP1A1, CYP1A2, CYP2C9 and 2 moreextracellular space, cytosol

• 20-oxo-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. transport of LTD4 (cytosol to extracellular)
  2. Resistance-Nodulation-Cell Division (Rnd) Tcdb:2.A.60.1.5
  3. 10-HETE[n] + NAD+[n] = H+[n] + NADH[n] + 20-oxo-(5Z,8Z,11Z,14Z)-eicosatetraenoate[n]

  Catalysed by SLCO1B1, ADH4extracellular space, cytosol, nucleusOne of 3 routes

• 4,8-dimethylnonanoyl-CoAReach from here →
  1. membrane dipeptidase (LTD4)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Carnitine Dimethyl Nonanoyl Transferase, Revsible, Peroxisomal

  Catalysed by DPEP1, DPEP2, BAAT, CRAT and 1 moreextracellular space, peroxisomeOne of 3 routes

• tetradecanedioyl-CoAReach from here →
  1. membrane dipeptidase (LTD4)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Fatty Acid Beta Oxidation (C16Dc->C14Dc), Peroxisomal

  Catalysed by DPEP1, DPEP2, BAAT, ACAA1 and 3 moreextracellular space, peroxisome

• hexadecanedioyl-CoAReach from here →
  1. membrane dipeptidase (LTD4)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Production of Hexadecanedioylcarnitine

  Catalysed by DPEP1, DPEP2, BAAT, CPT1A and 2 moreextracellular space, peroxisome, cytosolOne of 2 routes

• pristanoyl-CoAReach from here →
  1. membrane dipeptidase (LTD4)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. fatty-acid-CoA ligase

  Catalysed by DPEP1, DPEP2, BAAT, SLC27A2extracellular space, peroxisome, cytosolOne of 2 routes

• undecanoyl-CoAReach from here →
  1. membrane dipeptidase (LTD4)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. medium-chain acyl-CoA ligase (undecylic acid)

  Catalysed by DPEP1, DPEP2, BAAT, ACSM4 and 5 moreextracellular space, peroxisome, cytosolOne of 3 routes

• a fatty acyl-CoAReach from here →
  1. membrane dipeptidase (LTD4)
  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 DPEP1, DPEP2, GLYATL2extracellular space

• (9S)-hydroxy-(10E,12Z)-octadecadienoateReach from here →
  1. membrane dipeptidase (LTD4)
  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 DPEP1, DPEP2, GSS, GPX1 and 1 moreextracellular space

• 7-oxolithocholateReach from here →
  1. transport of LTD4 (cytosol to extracellular)
  2. solute carrier organic anion transporter (chenodiol)
  3. chenodeoxycholate + NAD(+) = 7-oxolithocholate + NADH + H(+)

  Catalysed by SLCO1B1, SLCO1A2, SLCO1B3, HSD17B10extracellular space, cytosolOne of 2 routes

• (11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoateReach from here →
  1. transport of LTD4 (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoate + A + H2O

  Catalysed by SLCO1B1, PTGS2extracellular space, cytosolOne of 2 routes

• (15R)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. transport of LTD4 (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (15R)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoate + A + H2O

  Catalysed by SLCO1B1, PTGS2extracellular space, cytosolOne of 2 routes

• (15R)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. transport of LTD4 (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (15R)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate

  Catalysed by SLCO1B1, PTGS2extracellular space, cytosol

• 11R-hydroperoxy-(5Z,8Z,12E,14Z)-eicosatetraenoateReach from here →
  1. transport of LTD4 (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. Arachidonate: oxygen 11-oxidoreductase

  Catalysed by SLCO1B1, ALOX12extracellular space, cytosolOne of 2 routes

• thio-Mo-molybdopterinReach from here →
  1. membrane dipeptidase (LTD4)
  2. transport of cysteine and glycine (cytosol to extracellular)
  3. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O

  Catalysed by DPEP1, DPEP2, SLC3A2, SLC7A5 and 2 moreextracellular space, cytosol

• (12R)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoateReach from here →
  1. membrane dipeptidase (LTD4)
  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 DPEP1, DPEP2, GSS, GPX1 and 2 moreextracellular spaceOne of 2 routes

• 14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoateReach from here →
  1. transport of LTD4 (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. unspecific monooxygenase (arachidonate)

  Catalysed by SLCO1B1, CYP1A1, CYP1A2, CYP2E1 and 24 moreextracellular space, cytosolOne of 4 routes

• 8,9-epoxy-(5Z,11Z,14Z)-eicosatrienoateReach from here →
  1. transport of LTD4 (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. unspecific monooxygenase (arachidonate)

  Catalysed by SLCO1B1, CYP1A1, CYP1A2, CYP2E1 and 23 moreextracellular space, cytosolOne of 3 routes

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoserineReach from here →
  1. transport of LTD4 (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoserine + H2O = 1-heptadecanoyl-sn-glycero-3-phosphoserine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)

  Catalysed by SLCO1B1, ABHD16Aextracellular space, cytosol

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. transport of LTD4 (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + H2O = 1-heptadecanoyl-sn-glycero-3-phosphocholine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)

  Catalysed by SLCO1B1, ABHD16Aextracellular space, cytosol

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. transport of LTD4 (cytosol to extracellular)
  2. transport of arachidonate (cytosol to extracellular)
  3. 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine + H2O = 1-heptadecanoyl-sn-glycero-3-phosphoethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)

  Catalysed by SLCO1B1, ABHD16Aextracellular space, cytosol

• (5Z)-tetradecenoyl-CoAReach from here →
  1. membrane dipeptidase (LTD4)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (physeteric acid)

  Catalysed by DPEP1, DPEP2, BAAT, SLC27A2 and 7 moreextracellular space, peroxisome, cytosolOne of 8 routes

• (3E)-decenoyl-CoAReach from here →
  1. membrane dipeptidase (LTD4)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. Fatty Acid Beta Oxidation (C12:1->C10:1), Mitochondrial

  Catalysed by DPEP1, DPEP2, BAAT, ACADM and 3 moreextracellular space, peroxisome, mitochondrial matrix

• 11beta-prostaglandin F2Reach from here →
  1. transport of LTD4 (cytosol to extracellular)
  2. transport of prostaglandin D2 (cytosol to extracellular)
  3. prostaglandin D2 + NADPH + H(+) = 11beta-prostaglandin F2 + NADP(+)

  Catalysed by SLCO1B1, AKR1C3, AKR1C2extracellular space, cytosol

• (2R,6)-dimethylheptanoyl-CoAReach from here →
  1. membrane dipeptidase (LTD4)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. acetyl-CoA C-acyltransferase (3-oxo-4(R),8-dimethyl-nonanoyl-CoA)

  Catalysed by DPEP1, DPEP2, BAAT, HADHA and 2 moreextracellular space, peroxisome, mitochondrial matrix

• 16alpha-hydroxydehydroepiandrosterone 3-sulfateReach from here →
  1. transport of LTD4 (cytosol to extracellular)
  2. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  3. dehydroepiandrosterone 3-sulfate + reduced [NADPH--hemoprotein reductase] + O2 = 16alpha-hydroxydehydroepiandrosterone 3-sulfate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by SLCO1B1, CYP3A7extracellular space, cytosol

• an N(2)-acyl-L-glutamineReach from here →
  1. membrane dipeptidase (LTD4)
  2. transport of glutamine and glycine (cytosol to extracellular)
  3. an acyl-CoA + L-glutamine = an N(2)-acyl-L-glutamine + CoA + H(+)

  Catalysed by DPEP1, DPEP2, SLC7A5, GLYATL1B and 1 moreextracellular space, cytosol

• (7Z)-hexadecenoyl-CoAReach from here →
  1. membrane dipeptidase (LTD4)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (7-palmitoleic acid)

  Catalysed by DPEP1, DPEP2, BAAT, SLC27A2 and 7 moreextracellular space, peroxisome, cytosolOne of 8 routes

• 3-methylmalateReach from here →
  1. membrane dipeptidase (LTD4)
  2. glycine + 2-oxoglutarate = glyoxylate + L-glutamate
  3. propanoyl-CoA + glyoxylate + H2O = 3-methylmalate + CoA + H(+)

  Catalysed by DPEP1, DPEP2, AADAT, CLYBLextracellular space

• tricosanoyl-CoAReach from here →
  1. membrane dipeptidase (LTD4)
  2. bile acid-CoA: amino acid N-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (tricosanoic acid)

  Catalysed by DPEP1, DPEP2, BAAT, SLC27A2 and 7 moreextracellular space, peroxisome, cytosolOne of 4 routes

• (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. membrane dipeptidase (LTD4)
  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 DPEP1, DPEP2, GSS, PTGES and 5 moreextracellular space

• (12S)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoateReach from here →
  1. membrane dipeptidase (LTD4)
  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 DPEP1, DPEP2, GSS, GPX1 and 1 moreextracellular space

• (12S)-hydroxy-(5Z,8E,10E)-heptadecatrienoateReach from here →
  1. transport of LTD4 (cytosol to extracellular)
  2. transport of prostaglandin H2 (cytosol to extracellular)
  3. prostaglandin H2 = (12S)-hydroxy-(5Z,8E,10E)-heptadecatrienoate + malonaldehyde

  Catalysed by SLCO1B1, TBXAS1, CYP2S1, PTGES2extracellular space, cytosol