(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA

Two steps

• (25R)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oyl-CoAReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. 3alpha,7alpha,12alpha-trihydroxy-5beta-cholestanoate:CoA ligase (AMP-forming)

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 1 morecytosol, endoplasmic reticulumOne of 3 routes

• deoxycholoyl-CoAReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. cholate-CoA ligase (3alpha,12alpha-dihydroxy-5beta-cholanate)

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 1 morecytosolOne of 4 routes

• decanoyl-CoAReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. medium-chain acyl-CoA ligase (decanoic acid)

  Catalysed by BAAT, ACOT6, ACOT1, ACSM4 and 5 morecytosolOne of 7 routes

• (2E)-hexadecenoyl-CoAReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. Carnitine O-Palmitoyltransferase

  Catalysed by BAAT, ACOT6, ACOT1, CPT1A and 2 morecytosolOne of 4 routes

• (9Z)-hexadecenoyl-CoAReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (palmitolate)

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 7 morecytosolOne of 12 routes

• a cardiolipinReach from here →
  1. acyl-CoA pool formation and breakdown
  2. 1'-[1,2-diacyl-sn-glycero-3-phospho],3'-[1-acyl-sn-glycero-3-phospho]-glycerol + an acyl-CoA = a cardiolipin + CoA

  Catalysed by HADHAcytosol

• 3-hydroxyisovaleryl-CoAReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. (3-Hydroxyisovalerylcoa->3-Hydroxyisovalerylcarnitine)

  Catalysed by BAAT, ACOT6, ACOT1, CPT1A and 1 morecytosol

• an all-trans-retinyl esterReach from here →
  1. acyl-CoA pool formation and breakdown
  2. all-trans-retinol + an acyl-CoA = an all-trans-retinyl ester + CoA

  Catalysed by DGAT1, PNPLA4, AWAT2, DGAT2cytosol

• CHEBI:63544Reach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (adrenic acid)

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 7 morecytosolOne of 8 routes

• a 1,2-diacyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. acyl-CoA pool formation and breakdown
  2. a 1-acyl-sn-glycero-3-phosphoethanolamine + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phosphoethanolamine + CoA

  Catalysed by LPCAT4, LPCAT3, MBOAT1, MBOAT2cytosol

• a triacyl-sn-glycerolReach from here →
  1. acyl-CoA pool formation and breakdown
  2. an acyl-CoA + a 1,2-diacyl-sn-glycerol = a triacyl-sn-glycerol + CoA

  Catalysed by DGAT1, MOGAT2, AWAT2, MOGAT3 and 2 morecytosol

• a 1,2-diacyl-sn-glycero-3-phospho-(1'-sn-glycerol)Reach from here →
  1. acyl-CoA pool formation and breakdown
  2. 1-acyl-sn-glycero-3-phospho-(1'-sn-glycerol) + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phospho-(1'-sn-glycerol) + CoA

  Catalysed by LCLAT1, LPCAT1, GPAMcytosol

• hexacosanoyl-CoAReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (cerotic acid)

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 7 morecytosolOne of 6 routes

• tetracosanoyl-CoAReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (lignocerate)

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 7 morecytosolOne of 11 routes

• docosanoyl-CoAReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (behenic acid)

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 7 morecytosolOne of 10 routes

• (2E)-octadecenoyl-CoAReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. Carnitine O-Palmitoyltransferase

  Catalysed by BAAT, ACOT6, ACOT1, CPT1A and 2 morecytosolOne of 3 routes

• 3-oxo-(8Z,11Z,14Z,17Z)-eicosatetraenoyl-CoAReach from here →
  1. Beta Oxidation of Fatty Acid
  2. (6Z,9Z,12Z,15Z)-octadecatetraenoyl-CoA + malonyl-CoA + H(+) = 3-oxo-(8Z,11Z,14Z,17Z)-eicosatetraenoyl-CoA + CO2 + CoA

  Catalysed by ACADM, ACADS, ELOVL5mitochondrial matrix

• (9Z,12Z,15Z,18Z,21Z)-3-oxotetracosapentaenoyl-CoAReach from here →
  1. fatty-acyl-CoA elongation (N-C20:5CoA)
  2. (7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl-CoA + malonyl-CoA + H(+) = (9Z,12Z,15Z,18Z,21Z)-3-oxotetracosapentaenoyl-CoA + CO2 + CoA

  Catalysed by ELOVL4, ELOVL6, ELOVL2, ELOVL5cytosol

• (9Z,12Z,15Z)-octadecatrienoyl-CoAReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (linolenate)

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 7 morecytosolOne of 8 routes

• (13Z)-docosenoyl-CoAReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (cis-erucic acid)

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 7 morecytosolOne of 7 routes

• (11Z)-eicosenoyl-CoAReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (cis-gondoic acid)

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 7 morecytosolOne of 8 routes

• (9Z,12Z,15Z,18Z,21Z)-tetracosapentaenoyl-CoAReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase ((9Z,12Z,15Z,18Z,21Z)-TPA)

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 7 morecytosolOne of 6 routes

• (6Z,9Z,12Z,15Z,18Z,21Z)-tetracosahexaenoyl-CoAReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase ((6Z,9Z,12Z,15Z,18Z,21Z)-THA)

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 7 morecytosolOne of 5 routes

• (15Z)-tetracosenoyl-CoAReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (nervonic acid)

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 7 morecytosolOne of 7 routes

• (17Z)-hexacosenoyl-CoAReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (ximenic acid)

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 7 morecytosolOne of 5 routes

• (8Z,11Z,14Z)-eicosatrienoyl-CoAReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 7 morecytosolOne of 6 routes

• (8Z,11Z,14Z,17Z)-eicosatetraenoyl-CoAReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (omega-3-arachidonic acid)

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 7 morecytosolOne of 7 routes

• (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoAReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (DHA)

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 7 morecytosolOne of 10 routes

• heptadecanoyl-CoAReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (margaric acid)

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 7 morecytosolOne of 7 routes

• (9Z)-heptadecenoyl-CoAReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (9-heptadecylenic acid)

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 7 morecytosolOne of 6 routes

• (11Z,14Z,17Z)-eicosatrienoyl-CoAReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase ((11Z,14Z,17Z)-eicosatrienoic acid)

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 7 morecytosolOne of 6 routes

• nonadecanoyl-CoAReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (nonadecylic acid)

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 7 morecytosolOne of 7 routes

• (11Z)-octadecenoyl-CoAReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix

  Catalysed by BAAT, ACOT6, ACOT1, CPT1A and 2 morecytosolOne of 3 routes

• a 2,3-diacyl-sn-glycerolReach from here →
  1. acyl-CoA pool formation and breakdown
  2. a 2-acylglycerol + an acyl-CoA = a 2,3-diacyl-sn-glycerol + CoA

  Catalysed by MOGAT2, MOGAT1cytosol

• 1-O-alkyl-3-acylglycerolReach from here →
  1. acyl-CoA pool formation and breakdown
  2. 1-O-alkylglycerol + an acyl-CoA = 1-O-alkyl-3-acylglycerol + CoA

  Catalysed by MOGAT2, AWAT2cytosol

• dodecanedioyl-CoAReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. Activation of dodecanedioic acid

  Catalysed by BAAT, ACOT6, ACOT1cytosolOne of 4 routes

• decanedioyl-CoAReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. Production of Sebacoylcarnitine

  Catalysed by BAAT, ACOT6, ACOT1, CPT1A and 2 morecytosolOne of 4 routes

• octanedioyl-CoAReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. Production of Suberylcarnitine

  Catalysed by BAAT, ACOT6, ACOT1, CPT1A and 2 morecytosolOne of 4 routes

• hexanedioyl-CoAReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. Activation of adipic acid for Formation of Adipoyl Carnitine

  Catalysed by BAAT, ACOT6, ACOT1cytosolOne of 4 routes

• (4Z,7Z,10Z,13Z,16Z)-docosapentaenoyl-CoAReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase ((4Z,7Z,10Z,13Z,16Z)-DPA)

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 7 morecytosolOne of 8 routes

• (11Z,14Z)-eicosadienoyl-CoAReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase ((11Z,14Z)-eicosadienoic acid)

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 7 morecytosolOne of 6 routes

• (R)-3-hydroxy-(11Z)-octadecenoyl-CoAReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. Production of 3-Hydroxyoctadecenoylcarnitinec

  Catalysed by BAAT, ACOT6, ACOT1, CPT1A and 2 morecytosol

• (13Z)-eicosenoyl-CoAReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase ((13Z)-eicosenoic acid)

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 7 morecytosolOne of 6 routes

• (17R,18S)-epoxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + reduced [NADPH--hemoprotein reductase] + O2 = (17R,18S)-epoxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by BAAT, ACOT6, ACOT1, CYP1A1 and 6 morecytosol

• (17S,18R)-epoxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + reduced [NADPH--hemoprotein reductase] + O2 = (17S,18R)-epoxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by BAAT, ACOT6, ACOT1, CYP2C8 and 2 morecytosol

• 19-hydroxy-(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoateReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. EPA[r] + O2[r] + FMNH2[r] = FMN[r] + H2O[r] + 19-hydroxy-(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate[r]

  Catalysed by BAAT, ACOT6, ACOT1, CYP2E1cytosol, endoplasmic reticulumOne of 3 routes

• 20-hydroxy-(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoateReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + reduced [NADPH--hemoprotein reductase] + O2 = 20-hydroxy-(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by BAAT, ACOT6, ACOT1, CYP4F2 and 2 morecytosol

• 4,8-dimethylnonanoyl-CoAReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. Carnitine Dimethyl Nonanoyl Transferase, Revsible, Peroxisomal

  Catalysed by BAAT, ACOT6, ACOT1, CRAT and 1 morecytosol, peroxisomeOne of 3 routes

• tetradecanedioyl-CoAReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. Fatty Acid Beta Oxidation (C16Dc->C14Dc), Peroxisomal

  Catalysed by BAAT, ACOT6, ACOT1, ACAA1 and 3 morecytosol, peroxisome

• hexadecanedioyl-CoAReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. Production of Hexadecanedioylcarnitine

  Catalysed by BAAT, ACOT6, ACOT1, CPT1A and 2 morecytosolOne of 2 routes