1-octadecanoyl-sn-glycero-3-phosphate

Three steps

• 11R-hydroperoxy-(5Z,8Z,12E,14Z)-eicosatetraenoateReach from here →
  1. 1-octadecanoyl-sn-glycero-3-phosphate + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate + CoA
  2. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate + H2O = 1-octadecanoyl-sn-glycero-3-phosphate + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)
  3. Arachidonate: oxygen 11-oxidoreductase

  Catalysed by AGPAT3, PLA2G4A, ALOX12cytosolOne of 2 routes

• prostaglandin G2Reach from here →
  1. 1-octadecanoyl-sn-glycero-3-phosphate + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate + CoA
  2. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate + H2O = 1-octadecanoyl-sn-glycero-3-phosphate + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)
  3. Arachidonate:oxygen oxidoreductase

  Catalysed by AGPAT3, PLA2G4A, PTGS1, PTGS2endoplasmic reticulumOne of 2 routes

• 1-hexadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphateReach from here →
  1. 1-acylglycerol-3P-LD-TG1 pool (liver tissue) formation
  2. 1-acylglycerol-3-phosphate pool formation and breakdown
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA + 1-hexadecanoyl-sn-glycero-3-phosphate = 1-hexadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphate + CoA

  Catalysed by AGPAT4cytosol

• (12R)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoateReach from here →
  1. 1-octadecanoyl-sn-glycero-3-phosphate + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate + CoA
  2. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate + H2O = 1-octadecanoyl-sn-glycero-3-phosphate + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)
  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 AGPAT3, PLA2G4A, CYP2C9

• 14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoateReach from here →
  1. 1-octadecanoyl-sn-glycero-3-phosphate + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate + CoA
  2. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate + H2O = 1-octadecanoyl-sn-glycero-3-phosphate + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)
  3. unspecific monooxygenase (arachidonate)

  Catalysed by AGPAT3, PLA2G4A, CYP1A1, CYP1A2 and 25 morecytosolOne of 4 routes

• 8,9-epoxy-(5Z,11Z,14Z)-eicosatrienoateReach from here →
  1. 1-octadecanoyl-sn-glycero-3-phosphate + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate + CoA
  2. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate + H2O = 1-octadecanoyl-sn-glycero-3-phosphate + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)
  3. unspecific monooxygenase (arachidonate)

  Catalysed by AGPAT3, PLA2G4A, CYP1A1, CYP1A2 and 24 morecytosolOne of 3 routes

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoserineReach from here →
  1. 1-octadecanoyl-sn-glycero-3-phosphate + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate + CoA
  2. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate + H2O = 1-octadecanoyl-sn-glycero-3-phosphate + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)
  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 AGPAT3, PLA2G4A, ABHD16A

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. 1-octadecanoyl-sn-glycero-3-phosphate + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate + CoA
  2. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate + H2O = 1-octadecanoyl-sn-glycero-3-phosphate + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)
  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 AGPAT3, PLA2G4A, ABHD16A

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. 1-octadecanoyl-sn-glycero-3-phosphate + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate + CoA
  2. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate + H2O = 1-octadecanoyl-sn-glycero-3-phosphate + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)
  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 AGPAT3, PLA2G4A, ABHD16A

• (5Z)-tetradecenoyl-CoAReach from here →
  1. 1-acylglycerol-3P-LD-TG1 pool (liver tissue) formation
  2. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (physeteric acid)

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 13 morecytosol, mitochondrial matrixOne of 8 routes

• (3E)-decenoyl-CoAReach from here →
  1. 1-acylglycerol-3P-LD-TG1 pool (liver tissue) formation
  2. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  3. Fatty Acid Beta Oxidation (C12:1->C10:1), Mitochondrial

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 9 morecytosol, mitochondrial matrix

• (2R,6)-dimethylheptanoyl-CoAReach from here →
  1. 1-acylglycerol-3P-LD-TG1 pool (liver tissue) formation
  2. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  3. acetyl-CoA C-acyltransferase (3-oxo-4(R),8-dimethyl-nonanoyl-CoA)

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 8 morecytosol, mitochondrial matrix

• (7Z)-hexadecenoyl-CoAReach from here →
  1. 1-acylglycerol-3P-LD-TG1 pool (liver tissue) formation
  2. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (7-palmitoleic acid)

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 13 morecytosol, mitochondrial matrixOne of 8 routes

• tricosanoyl-CoAReach from here →
  1. 1-acylglycerol-3P-LD-TG1 pool (liver tissue) formation
  2. acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase
  3. long-chain-fatty-acid-CoA ligase (tricosanoic acid)

  Catalysed by AGPAT2, LCLAT1, MBOAT1, MBOAT2 and 13 morecytosol, mitochondrial matrixOne of 4 routes

• (18R)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. 1-octadecanoyl-sn-glycero-3-phosphate + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate + CoA
  2. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate + H2O = 1-octadecanoyl-sn-glycero-3-phosphate + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)
  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 AGPAT3, PLA2G4A, CYP4F8

• 15-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. 1-octadecanoyl-sn-glycero-3-phosphate + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate + CoA
  2. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate + H2O = 1-octadecanoyl-sn-glycero-3-phosphate + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = 15-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate

  Catalysed by AGPAT3, PLA2G4A, ALOX15B

• 5-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. 1-octadecanoyl-sn-glycero-3-phosphate + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate + CoA
  2. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate + H2O = 1-octadecanoyl-sn-glycero-3-phosphate + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = 5-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate

  Catalysed by AGPAT3, PLA2G4A, ALOX15B