3-oxo-(7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl-CoA

Three steps

• (7Z,10Z,13Z,16Z,19Z)-docosapentaenoateReach from here →
  1. 3-oxo-(7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl-CoA + CoA = (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA + acetyl-CoA
  2. fatty-acyl-CoA elongation (N-C20:5CoA)
  3. (7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl-CoA hydrolase

  Catalysed by ACAA1, ELOVL4, ELOVL6, ELOVL2 and 3 morecytosol

• pristanoyl-CoAReach from here →
  1. 3-oxo-(7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl-CoA + CoA = (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA + acetyl-CoA
  2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  3. fatty-acid-CoA ligase

  Catalysed by ACAA1, BAAT, ACOT6, ACOT1 and 1 morecytosolOne of 2 routes

• a 1,3-diacyl-sn-glycerolReach from here →
  1. 3-oxo-(7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl-CoA + CoA = (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA + acetyl-CoA
  2. acyl-CoA pool formation and breakdown
  3. a 3-acyl-sn-glycerol + an acyl-CoA = a 1,3-diacyl-sn-glycerol + CoA

  Catalysed by ACAA1, MOGAT1cytosolOne of 2 routes

• a 1-O-(1Z-alkenyl)-2-acyl-sn-glycero-3-phosphocholineReach from here →
  1. 3-oxo-(7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl-CoA + CoA = (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA + acetyl-CoA
  2. acyl-CoA pool formation and breakdown
  3. a 1-O-(1Z-alkenyl)-sn-glycero-3-phosphocholine + an acyl-CoA = a 1-O-(1Z-alkenyl)-2-acyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by ACAA1, LPCAT2, LPCAT1cytosol

• a 1-O-(1Z-alkenyl)-2-acyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. 3-oxo-(7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl-CoA + CoA = (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA + acetyl-CoA
  2. acyl-CoA pool formation and breakdown
  3. a 1-O-(1Z-alkenyl)-sn-glycero-3-phosphoethanolamine + an acyl-CoA = a 1-O-(1Z-alkenyl)-2-acyl-sn-glycero-3-phosphoethanolamine + CoA

  Catalysed by ACAA1, LPCAT4cytosol

• undecanoyl-CoAReach from here →
  1. 3-oxo-(7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl-CoA + CoA = (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA + acetyl-CoA
  2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  3. medium-chain acyl-CoA ligase (undecylic acid)

  Catalysed by ACAA1, BAAT, ACOT6, ACOT1 and 6 morecytosolOne of 3 routes

• (5Z,7Z,8Z,10E,14Z,17Z)-12-hydroperoxyeicosapentaenoateReach from here →
  1. 3-oxo-(7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl-CoA + CoA = (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA + acetyl-CoA
  2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + O2 = (5Z,7Z,8Z,10E,14Z,17Z)-12-hydroperoxyeicosapentaenoate

  Catalysed by ACAA1, BAAT, ACOT6, ACOT1 and 1 morecytosol

• (5Z)-tetradecenoyl-CoAReach from here →
  1. 3-oxo-(7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl-CoA + CoA = (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA + acetyl-CoA
  2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (physeteric acid)

  Catalysed by ACAA1, BAAT, ACOT6, ACOT1 and 8 morecytosolOne of 9 routes

• (3E)-decenoyl-CoAReach from here →
  1. 3-oxo-(7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl-CoA + CoA = (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA + acetyl-CoA
  2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  3. Fatty Acid Beta Oxidation (C12:1->C10:1), Mitochondrial

  Catalysed by ACAA1, BAAT, ACOT6, ACOT1 and 4 morecytosol, mitochondrial matrix

• (2R,6)-dimethylheptanoyl-CoAReach from here →
  1. 3-oxo-(7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl-CoA + CoA = (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA + acetyl-CoA
  2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  3. acetyl-CoA C-acyltransferase (3-oxo-4(R),8-dimethyl-nonanoyl-CoA)

  Catalysed by ACAA1, BAAT, ACOT6, ACOT1 and 3 morecytosol, mitochondrial matrix

• an N(2)-acyl-L-glutamineReach from here →
  1. 3-oxo-(7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl-CoA + CoA = (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA + acetyl-CoA
  2. acyl-CoA pool formation and breakdown
  3. an acyl-CoA + L-glutamine = an N(2)-acyl-L-glutamine + CoA + H(+)

  Catalysed by ACAA1, GLYATL1B, GLYATL1cytosol

• (7Z)-hexadecenoyl-CoAReach from here →
  1. 3-oxo-(7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl-CoA + CoA = (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA + acetyl-CoA
  2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (7-palmitoleic acid)

  Catalysed by ACAA1, BAAT, ACOT6, ACOT1 and 8 morecytosolOne of 9 routes

• tricosanoyl-CoAReach from here →
  1. 3-oxo-(7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl-CoA + CoA = (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA + acetyl-CoA
  2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (tricosanoic acid)

  Catalysed by ACAA1, BAAT, ACOT6, ACOT1 and 8 morecytosolOne of 5 routes

• a 3-oxoacyl-CoAReach from here →
  1. 3-oxo-(7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl-CoA + CoA = (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA + acetyl-CoA
  2. acyl-CoA pool formation and breakdown
  3. an acyl-CoA + acetyl-CoA = a 3-oxoacyl-CoA + CoA

  Catalysed by ACAA1, SCP2, ACAA2, HADHBcytosol

• (12S)-hydroperoxy-(5Z,8Z,10E,14Z,17Z)-eicosapentaenoateReach from here →
  1. 3-oxo-(7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl-CoA + CoA = (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA + acetyl-CoA
  2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + O2 = (12S)-hydroperoxy-(5Z,8Z,10E,14Z,17Z)-eicosapentaenoate

  Catalysed by ACAA1, BAAT, ACOT6, ACOT1 and 1 morecytosol

• (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoateReach from here →
  1. 3-oxo-(7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl-CoA + CoA = (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA + acetyl-CoA
  2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  3. prostaglandin-endoperoxide synthase (EPA)

  Catalysed by ACAA1, BAAT, ACOT6, ACOT1 and 2 morecytosolOne of 2 routes

• (15R)-hydroxy-(5Z,8Z,11Z,13E,17Z)-eicosapentaenoateReach from here →
  1. 3-oxo-(7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl-CoA + CoA = (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA + acetyl-CoA
  2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (15R)-hydroxy-(5Z,8Z,11Z,13E,17Z)-eicosapentaenoate + A + H2O

  Catalysed by ACAA1, BAAT, ACOT6, ACOT1 and 1 morecytosol

• (11R)-hydroxy-(5Z,8Z,12E,14Z,17Z)-eicosapentaenoateReach from here →
  1. 3-oxo-(7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl-CoA + CoA = (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA + acetyl-CoA
  2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (11R)-hydroxy-(5Z,8Z,12E,14Z,17Z)-eicosapentaenoate + A + H2O

  Catalysed by ACAA1, BAAT, ACOT6, ACOT1 and 1 morecytosol