1-(alk-1-enyl)-2-acyl-sn-glycero-3-phosphoethanolamine

Three steps

• (11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoateReach from here →
  1. plasmenylethanolamine 2-acylhydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoate + A + H2O

  Catalysed by PLA2G10, PLA2G6, PLA2G1B, PLA2G4B and 15 morecytosol, extracellular spaceOne of 2 routes

• (15R)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. plasmenylethanolamine 2-acylhydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (15R)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoate + A + H2O

  Catalysed by PLA2G10, PLA2G6, PLA2G1B, PLA2G4B and 15 morecytosol, extracellular spaceOne of 2 routes

• hexadecanoateReach from here →
  1. ethanolaminephosphotransferase (1-alkenyl-2-acylglycerol)
  2. 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycerol + CDP-ethanolamine = 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + CMP + H(+)
  3. 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + H2O = 2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + hexadecanoate + H(+)

  Catalysed by SELENOI, CEPT1, DDHD2cytosol

• (15R)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. plasmenylethanolamine 2-acylhydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (15R)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate

  Catalysed by PLA2G10, PLA2G6, PLA2G1B, PLA2G4B and 15 morecytosol, extracellular space

• 11R-hydroperoxy-(5Z,8Z,12E,14Z)-eicosatetraenoateReach from here →
  1. plasmenylethanolamine 2-acylhydrolase
  2. (10Z)-heptadecenoic acid formation
  3. Arachidonate: oxygen 11-oxidoreductase

  Catalysed by PLA2G10, PLA2G6, PLA2G1B, PLA2G4B and 15 morecytosol, extracellular spaceOne of 2 routes

• prostaglandin G2Reach from here →
  1. plasmenylethanolamine 2-acylhydrolase
  2. (10Z)-heptadecenoic acid formation
  3. Arachidonate:oxygen oxidoreductase

  Catalysed by PLA2G10, PLA2G6, PLA2G1B, PLA2G4B and 16 morecytosol, extracellular space, endoplasmic reticulumOne of 2 routes

• 14-hydroperoxy-(4Z,7Z,10Z,12E,16Z,19Z)-docosahexaenoateReach from here →
  1. plasmenylethanolamine 2-acylhydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + O2 = 14-hydroperoxy-(4Z,7Z,10Z,12E,16Z,19Z)-docosahexaenoate

  Catalysed by PLA2G10, PLA2G6, PLA2G1B, PLA2G4B and 15 morecytosol, extracellular space

• (12R)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoateReach from here →
  1. plasmenylethanolamine 2-acylhydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = (12R)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by PLA2G10, PLA2G6, PLA2G1B, PLA2G4B and 15 morecytosol, extracellular space

• 14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoateReach from here →
  1. plasmenylethanolamine 2-acylhydrolase
  2. (10Z)-heptadecenoic acid formation
  3. unspecific monooxygenase (arachidonate)

  Catalysed by PLA2G10, PLA2G6, PLA2G1B, PLA2G4B and 41 morecytosol, extracellular spaceOne of 4 routes

• 8,9-epoxy-(5Z,11Z,14Z)-eicosatrienoateReach from here →
  1. plasmenylethanolamine 2-acylhydrolase
  2. (10Z)-heptadecenoic acid formation
  3. unspecific monooxygenase (arachidonate)

  Catalysed by PLA2G10, PLA2G6, PLA2G1B, PLA2G4B and 40 morecytosol, extracellular spaceOne of 3 routes

• tetradecanalReach from here →
  1. plasmenylethanolamine 2-acylhydrolase
  2. (10Z)-heptadecenoic acid formation
  3. tetradecanal + NAD(+) + H2O = tetradecanoate + NADH + 2 H(+)

  Catalysed by PLA2G10, PLA2G6, PLA2G1B, PLA2G4B and 15 morecytosol, extracellular space

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoserineReach from here →
  1. plasmenylethanolamine 2-acylhydrolase
  2. (10Z)-heptadecenoic acid formation
  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 PLA2G10, PLA2G6, PLA2G1B, PLA2G4B and 15 morecytosol, extracellular space

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. plasmenylethanolamine 2-acylhydrolase
  2. (10Z)-heptadecenoic acid formation
  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 PLA2G10, PLA2G6, PLA2G1B, PLA2G4B and 15 morecytosol, extracellular space

• 1-O-acyl-N-(acetyl)-sphing-4-enineReach from here →
  1. ethanolaminephosphotransferase (1-alkenyl-2-acylglycerol)
  2. CDP-ethanolamine + a 1,2-diacyl-sn-glycerol = a 1,2-diacyl-sn-glycero-3-phosphoethanolamine + CMP + H(+)
  3. N-(acetyl)-sphing-4-enine + a 1,2-diacyl-sn-glycero-3-phosphoethanolamine = 1-O-acyl-N-(acetyl)-sphing-4-enine + a 1-acyl-sn-glycero-3-phosphoethanolamine

  Catalysed by SELENOI, CEPT1, PLA2G15cytosolOne of 2 routes

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. plasmenylethanolamine 2-acylhydrolase
  2. (10Z)-heptadecenoic acid formation
  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 PLA2G10, PLA2G6, PLA2G1B, PLA2G4B and 15 morecytosol, extracellular space

• (5Z)-tetradecenoyl-CoAReach from here →
  1. plasmenylethanolamine 2-acylhydrolase
  2. Acyl-CoA:1-alkenylglycerophosphoethanolamine O-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (physeteric acid)

  Catalysed by PLA2G10, PLA2G6, PLA2G1B, PLA2G4B and 26 morecytosolOne of 8 routes

• (3E)-decenoyl-CoAReach from here →
  1. plasmenylethanolamine 2-acylhydrolase
  2. Acyl-CoA:1-alkenylglycerophosphoethanolamine O-acyltransferase
  3. Fatty Acid Beta Oxidation (C12:1->C10:1), Mitochondrial

  Catalysed by PLA2G10, PLA2G6, PLA2G1B, PLA2G4B and 22 morecytosol, mitochondrial matrix

• 7-hydroxydodecanoateReach from here →
  1. plasmenylethanolamine 2-acylhydrolase
  2. (10Z)-heptadecenoic acid formation
  3. dodecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 7-hydroxydodecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by PLA2G10, PLA2G6, PLA2G1B, PLA2G4B and 15 morecytosol, extracellular space

• N-(dodecanoyl)-sphinganineReach from here →
  1. plasmenylethanolamine 2-acylhydrolase
  2. (10Z)-heptadecenoic acid formation
  3. N-(dodecanoyl)-sphinganine + H2O = dodecanoate + sphinganine

  Catalysed by PLA2G10, PLA2G6, PLA2G1B, PLA2G4B and 15 morecytosol, extracellular space

• N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. ethanolaminephosphotransferase (1-alkenyl-2-acylglycerol)
  2. CDP-ethanolamine + 1,2-di-(9Z-octadecenoyl)-sn-glycerol = 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + CMP + H(+)
  3. 1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + 1-hexadecanoyl-sn-glycero-3-phosphocholine + H(+)

  Catalysed by SELENOI, CEPT1, PLAAT5cytosolOne of 2 routes

• N,1,2-tri-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. ethanolaminephosphotransferase (1-alkenyl-2-acylglycerol)
  2. CDP-ethanolamine + 1,2-di-(9Z-octadecenoyl)-sn-glycerol = 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + CMP + H(+)
  3. 2 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine = N,1,2-tri-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + 2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + H(+)

  Catalysed by SELENOI, CEPT1, PLA2G4EcytosolOne of 2 routes

• N-octadecanoyl-1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. ethanolaminephosphotransferase (1-alkenyl-2-acylglycerol)
  2. CDP-ethanolamine + 1,2-di-(9Z-octadecenoyl)-sn-glycerol = 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + CMP + H(+)
  3. 1-octadecanoyl-2-hexadecanoyl-sn-glycero-3-phosphocholine + 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine = N-octadecanoyl-1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + 2-hexadecanoyl-sn-glycero-3-phosphocholine + H(+)

  Catalysed by SELENOI, CEPT1, PLA2G4Ecytosol

• 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phospho-N-methylethanolamineReach from here →
  1. ethanolaminephosphotransferase (1-alkenyl-2-acylglycerol)
  2. CDP-ethanolamine + 1,2-di-(9Z-octadecenoyl)-sn-glycerol = 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + CMP + H(+)
  3. 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + S-adenosyl-L-methionine = 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phospho-N-methylethanolamine + S-adenosyl-L-homocysteine + H(+)

  Catalysed by SELENOI, CEPT1, PEMTcytosol

• (2R,6)-dimethylheptanoyl-CoAReach from here →
  1. plasmenylethanolamine 2-acylhydrolase
  2. Acyl-CoA:1-alkenylglycerophosphoethanolamine O-acyltransferase
  3. acetyl-CoA C-acyltransferase (3-oxo-4(R),8-dimethyl-nonanoyl-CoA)

  Catalysed by PLA2G10, PLA2G6, PLA2G1B, PLA2G4B and 21 morecytosol, mitochondrial matrix

• (7Z)-hexadecenoyl-CoAReach from here →
  1. plasmenylethanolamine 2-acylhydrolase
  2. Acyl-CoA:1-alkenylglycerophosphoethanolamine O-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (7-palmitoleic acid)

  Catalysed by PLA2G10, PLA2G6, PLA2G1B, PLA2G4B and 26 morecytosolOne of 8 routes

• tricosanoyl-CoAReach from here →
  1. plasmenylethanolamine 2-acylhydrolase
  2. Acyl-CoA:1-alkenylglycerophosphoethanolamine O-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (tricosanoic acid)

  Catalysed by PLA2G10, PLA2G6, PLA2G1B, PLA2G4B and 26 morecytosolOne of 6 routes

• (12S)-hydroperoxy-(5Z,8Z,10E,14Z,17Z)-eicosapentaenoateReach from here →
  1. plasmenylethanolamine 2-acylhydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + O2 = (12S)-hydroperoxy-(5Z,8Z,10E,14Z,17Z)-eicosapentaenoate

  Catalysed by PLA2G10, PLA2G6, PLA2G1B, PLA2G4B and 15 morecytosol, extracellular space

• (18R)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. plasmenylethanolamine 2-acylhydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by PLA2G10, PLA2G6, PLA2G1B, PLA2G4B and 15 morecytosol, extracellular space

• 17R-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoateReach from here →
  1. plasmenylethanolamine 2-acylhydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + AH2 + O2 = 17R-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate + A + H2O

  Catalysed by PLA2G10, PLA2G6, PLA2G1B, PLA2G4B and 15 morecytosol, extracellular space

• 13-hydroxy-(4Z,7Z,10Z,14E,16Z,19Z)-docosahexaenoateReach from here →
  1. plasmenylethanolamine 2-acylhydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + AH2 + O2 = 13-hydroxy-(4Z,7Z,10Z,14E,16Z,19Z)-docosahexaenoate + A + H2O

  Catalysed by PLA2G10, PLA2G6, PLA2G1B, PLA2G4B and 15 morecytosol, extracellular space

• (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoateReach from here →
  1. plasmenylethanolamine 2-acylhydrolase
  2. (10Z)-heptadecenoic acid formation
  3. prostaglandin-endoperoxide synthase (EPA)

  Catalysed by PLA2G10, PLA2G6, PLA2G1B, PLA2G4B and 16 morecytosol, extracellular spaceOne of 2 routes

• (15R)-hydroxy-(5Z,8Z,11Z,13E,17Z)-eicosapentaenoateReach from here →
  1. plasmenylethanolamine 2-acylhydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (15R)-hydroxy-(5Z,8Z,11Z,13E,17Z)-eicosapentaenoate + A + H2O

  Catalysed by PLA2G10, PLA2G6, PLA2G1B, PLA2G4B and 15 morecytosol, extracellular space

• (11R)-hydroxy-(5Z,8Z,12E,14Z,17Z)-eicosapentaenoateReach from here →
  1. plasmenylethanolamine 2-acylhydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (11R)-hydroxy-(5Z,8Z,12E,14Z,17Z)-eicosapentaenoate + A + H2O

  Catalysed by PLA2G10, PLA2G6, PLA2G1B, PLA2G4B and 15 morecytosol, extracellular space

• 15-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. plasmenylethanolamine 2-acylhydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = 15-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate

  Catalysed by PLA2G10, PLA2G6, PLA2G1B, PLA2G4B and 15 morecytosol, extracellular space

• 5-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. plasmenylethanolamine 2-acylhydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = 5-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate

  Catalysed by PLA2G10, PLA2G6, PLA2G1B, PLA2G4B and 15 morecytosol, extracellular space

• 13R-hydroxy-(7Z,10Z,14E,16Z,19Z)-docosapentaenoateReach from here →
  1. plasmenylethanolamine 2-acylhydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (7Z,10Z,13Z,16Z,19Z)-docosapentaenoate + AH2 + O2 = 13R-hydroxy-(7Z,10Z,14E,16Z,19Z)-docosapentaenoate + A + H2O

  Catalysed by PLA2G10, PLA2G6, PLA2G1B, PLA2G4B and 15 morecytosol, extracellular space