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

Three steps

• O-octadecanoyl-(R)-carnitineReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. (R)-carnitine + octadecanoyl-CoA = O-octadecanoyl-(R)-carnitine + CoA

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 7 morecytosol

• O-eicosanoyl-(R)-carnitineReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (eicosanoate)
  3. eicosanoyl-CoA + (R)-carnitine = O-eicosanoyl-(R)-carnitine + CoA

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 8 morecytosol

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

  Catalysed by BAAT, ACOT6, ACOT1, CPT1A and 4 morecytosol, peroxisomeOne of 7 routes

• 1,2-diacyl-sn-glycero-3-phosphoethanolReach from here →
  1. acyl-CoA pool formation and breakdown
  2. a 2-acyl-sn-glycero-3-phosphocholine + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phosphocholine + CoA
  3. ethanol + a 1,2-diacyl-sn-glycero-3-phosphocholine = 1,2-diacyl-sn-glycero-3-phosphoethanol + choline

  Catalysed by LPGAT1, PLD1cytosol

• 1-octadecanoyl-2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphocholineReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. 2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine + octadecanoyl-CoA = 1-octadecanoyl-2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 7 morecytosol

• 1-octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. 2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholine + octadecanoyl-CoA = 1-octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholine + CoA

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 7 morecytosol

• N-tetradecanoylglycineReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. tetradecanoyl-CoA + glycine = N-tetradecanoylglycine + CoA + H(+)

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 8 morecytosolOne of 2 routes

• N-eicosanoylglycinateReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (eicosanoate)
  3. eicosanoyl-CoA + glycine = N-eicosanoylglycinate + CoA + H(+)

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 7 morecytosolOne of 2 routes

• N-docosanoylglycineReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (behenic acid)
  3. docosanoyl-CoA + glycine = N-docosanoylglycine + CoA + H(+)

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 7 morecytosolOne of 2 routes

• N-hexacosanoylglycineReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (cerotic acid)
  3. hexacosanoyl-CoA + glycine = N-hexacosanoylglycine + CoA + H(+)

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 7 morecytosolOne of 2 routes

• (2E,5Z)-tetradecadienoyl-CoAReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (physeteric acid)
  3. medium-chain acyl-CoA dehydrogenase (5-tetradecenoyl-CoA)

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 11 morecytosol, mitochondrial matrixOne of 4 routes

• (2E,7Z)-hexadecadienoyl-CoAReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. long-chain-fatty-acid-CoA ligase (7-palmitoleic acid)
  3. medium-chain acyl-CoA dehydrogenase (7-hexadecenoyl-CoA)

  Catalysed by BAAT, ACOT6, ACOT1, SLC27A2 and 11 morecytosol, mitochondrial matrixOne of 4 routes

• cholesteryl (11Z)-octadecenoateReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix
  3. (11Z)-octadecenoyl-CoA + cholesterol = cholesteryl (11Z)-octadecenoate + CoA

  Catalysed by BAAT, ACOT6, ACOT1, CPT1A and 3 morecytosol

• 13R-hydroxy-(7Z,10Z,14E,16Z,19Z)-docosapentaenoateReach from here →
  1. fatty-acyl-CoA elongation (N-C20:5CoA)
  2. (7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl-CoA hydrolase
  3. (7Z,10Z,13Z,16Z,19Z)-docosapentaenoate + AH2 + O2 = 13R-hydroxy-(7Z,10Z,14E,16Z,19Z)-docosapentaenoate + A + H2O

  Catalysed by ELOVL4, ELOVL6, ELOVL2, ELOVL5 and 3 morecytosol

• taurochenodeoxycholateReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  2. Propanoyl-CoA:acetyl-CoA C-acyltransferase
  3. 3alpha,7alpha-dihydroxy-5beta-cholanoyl-CoA:taurine N-choloyltransferase

  Catalysed by BAAT, ACOT6, ACOT1, ACAA1 and 2 morecytosol, peroxisomeOne of 5 routes