an acyl-CoA

Three steps

• 1-O-(9Z)-octadecenyl (9Z)-octadecenoateReach from here →
  1. acyl-CoA pool formation and breakdown
  2. octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. (9Z)-octadecen-1-ol + (9Z)-octadecenoyl-CoA = 1-O-(9Z)-octadecenyl (9Z)-octadecenoate + CoA

  Catalysed by SCD, SCD5, AWAT1, AWAT2cytosol

• 1-O-eicosanyl (9Z)-octadecenoateReach from here →
  1. acyl-CoA pool formation and breakdown
  2. eicosanoyl-CoA + 2 NADPH + 2 H(+) = eicosan-1-ol + 2 NADP(+) + CoA
  3. eicosan-1-ol + (9Z)-octadecenoyl-CoA = 1-O-eicosanyl (9Z)-octadecenoate + CoA

  Catalysed by FAR1, FAR2, AWAT1cytosolOne of 2 routes

• 1,3-dihexadecanoyl-2-(9Z-octadecenoyl)glycerolReach from here →
  1. acyl-CoA pool formation and breakdown
  2. hexadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-hexadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycerol + hexadecanoyl-CoA = 1,3-dihexadecanoyl-2-(9Z-octadecenoyl)glycerol + CoA

  Catalysed by SCD, SCD5, MOGAT3cytosol

• 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-3-(9Z)-octadecenoyl-sn-glycerolReach from here →
  1. acyl-CoA pool formation and breakdown
  2. octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerol + (9Z)-octadecenoyl-CoA = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-3-(9Z)-octadecenoyl-sn-glycerol + CoA

  Catalysed by SCD, SCD5, DGAT1cytosol

• 1,3-di-(9Z-octadecenoyl)-glycerolReach from here →
  1. acyl-CoA pool formation and breakdown
  2. octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. 1-(9Z-octadecenoyl)-sn-glycerol + (9Z)-octadecenoyl-CoA = 1,3-di-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by SCD, SCD5, MOGAT2, MOGAT1cytosol

• 1-(9Z-octadecenoyl)-3-hexadecanoylglycerolReach from here →
  1. acyl-CoA pool formation and breakdown
  2. octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. 1-hexadecanoylglycerol + (9Z)-octadecenoyl-CoA = 1-(9Z-octadecenoyl)-3-hexadecanoylglycerol + CoA

  Catalysed by SCD, SCD5, MOGAT2, MOGAT1cytosol

• 2-O-(5Z,8Z,11Z,14Z)-eicosatetraenylglycerolReach from here →
  1. acyl-CoA pool formation and breakdown
  2. Arachidonyl-CoA hydrolase
  3. fatty acid amide hydrolase (arachidonate)

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 2 morecytosol

• (R)-2-hydroxytetracosanoateReach from here →
  1. acyl-CoA pool formation and breakdown
  2. Tetracosenoyl-CoA hydrolase
  3. tetracosanoate + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (R)-2-hydroxytetracosanoate + 2 Fe(III)-[cytochrome b5] + H2O

  Catalysed by BAAT, THEM4, FA2Hcytosol

• di-(9Z)-octadecenoylglycerolReach from here →
  1. all-trans-retinol + an acyl-CoA = an all-trans-retinyl ester + CoA
  2. carboxylesterase (retinyl-ester)
  3. 1,2,3-tri-(9Z-octadecenoyl)-glycerol + all-trans-retinol = all-trans-retinyl 9Z-octadecenoate + di-(9Z)-octadecenoylglycerol

  Catalysed by DGAT1, PNPLA4, AWAT2, DGAT2 and 19 morecytosol

• 1'-[1,2-diacyl-sn-glycero-3-phospho],3'-[1-acyl,2-octanoyl-sn-glycero-3-phospho]-glycerolReach from here →
  1. acyl-CoA:sn-glycerol-3-phosphate 1-O-acyltransferase
  2. Octanoyl-CoA:L-carnitine O-octanoyltransferase
  3. 1'-[1,2-diacyl-sn-glycero-3-phospho],3'-[1-acyl-sn-glycero-3-phospho]-glycerol + octanoyl-CoA = 1'-[1,2-diacyl-sn-glycero-3-phospho],3'-[1-acyl,2-octanoyl-sn-glycero-3-phospho]-glycerol + CoA

  Catalysed by GPAT3, GPAT2, GPAT4, GPAM and 2 moremitochondrial matrixOne of 2 routes

• 1'-[1-acyl-2-octanoyl-sn-glycero-3-phospho],3'-[1-acyl,2-hydroxy-sn-glycero-3-phospho]-glycerolReach from here →
  1. acyl-CoA:sn-glycerol-3-phosphate 1-O-acyltransferase
  2. Octanoyl-CoA:L-carnitine O-octanoyltransferase
  3. 1',3'-bis-[1-acyl-sn-glycero-3-phospho]-glycerol + octanoyl-CoA = 1'-[1-acyl-2-octanoyl-sn-glycero-3-phospho],3'-[1-acyl,2-hydroxy-sn-glycero-3-phospho]-glycerol + CoA

  Catalysed by GPAT3, GPAT2, GPAT4, GPAM and 2 moremitochondrial matrix

• 1'-[1,2-diacyl-sn-glycero-3-phospho],3'-[1-acyl,2-hexadecanoyl-sn-glycero-3-phospho]-glycerolReach from here →
  1. acyl-CoA pool formation and breakdown
  2. hexadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-hexadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. 1'-[1,2-diacyl-sn-glycero-3-phospho],3'-[1-acyl-sn-glycero-3-phospho]-glycerol + hexadecanoyl-CoA = 1'-[1,2-diacyl-sn-glycero-3-phospho],3'-[1-acyl,2-hexadecanoyl-sn-glycero-3-phospho]-glycerol + CoA

  Catalysed by SCD, SCD5, LCLAT1cytosolOne of 2 routes

• 1'-[1,2-diacyl-sn-glycero-3-phospho],3'-[1-acyl,2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho]-glycerolReach from here →
  1. acyl-CoA pool formation and breakdown
  2. (8Z,11Z,14Z)-eicosatrienoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. 1'-[1,2-diacyl-sn-glycero-3-phospho],3'-[1-acyl-sn-glycero-3-phospho]-glycerol + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1'-[1,2-diacyl-sn-glycero-3-phospho],3'-[1-acyl,2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho]-glycerol + CoA

  Catalysed by FADS1, LCLAT1cytosolOne of 2 routes

• 1'-[1-acyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho],3'-[1-acyl,2-hydroxy-sn-glycero-3-phospho]-glycerolReach from here →
  1. acyl-CoA pool formation and breakdown
  2. (8Z,11Z,14Z)-eicosatrienoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. 1',3'-bis-[1-acyl-sn-glycero-3-phospho]-glycerol + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1'-[1-acyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho],3'-[1-acyl,2-hydroxy-sn-glycero-3-phospho]-glycerol + CoA

  Catalysed by FADS1, LCLAT1cytosol

• 1-(9Z-octadecenoyl)-N-(acetyl)-sphing-4-enineReach from here →
  1. acyl-CoA pool formation and breakdown
  2. 2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + octadecanoyl-CoA = 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + CoA
  3. 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-(9Z-octadecenoyl)-N-(acetyl)-sphing-4-enine + 1-octadecanoyl-sn-glycero-3-phosphocholine

  Catalysed by LPGAT1, PLA2G15cytosol

• 1-O-hexadecyl-3-(9Z)-octadecenoylglycerolReach from here →
  1. acyl-CoA pool formation and breakdown
  2. octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. 1-O-hexadecylglycerol + (9Z)-octadecenoyl-CoA = 1-O-hexadecyl-3-(9Z)-octadecenoylglycerol + CoA

  Catalysed by SCD, SCD5, MOGAT2cytosol

• 2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. acyl-CoA pool formation and breakdown
  2. 2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + octadecanoyl-CoA = 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + CoA
  3. 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-octadecanoyl-N-(acetyl)-sphing-4-enine + 2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine

  Catalysed by LPGAT1, PLA2G15cytosolOne of 3 routes

• 1-octadecanoyl-N-(acetyl)-sphing-4-enineReach from here →
  1. acyl-CoA pool formation and breakdown
  2. 2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + octadecanoyl-CoA = 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + CoA
  3. 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-octadecanoyl-N-(acetyl)-sphing-4-enine + 2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine

  Catalysed by LPGAT1, PLA2G15cytosolOne of 2 routes

• 2-octadecanoyl-sn-glycero-3-phosphocholineReach from here →
  1. acyl-CoA pool formation and breakdown
  2. octadecanoyl-CoA + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine + CoA
  3. 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine + 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine = 2-octadecanoyl-sn-glycero-3-phosphocholine + N-hexadecanoyl-1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + H(+)

  Catalysed by LPCAT3, PLA2G4EcytosolOne of 2 routes

• 1-hexadecanoyl-N-(acetyl)-sphing-4-enineReach from here →
  1. acyl-CoA pool formation and breakdown
  2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 1-hexadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholine + CoA
  3. 1-hexadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholine + 1-hexadecanoyl-N-(acetyl)-sphing-4-enine

  Catalysed by LPCAT1, PLA2G15cytosolOne of 2 routes

• 2-hexadecanoyl-sn-glycero-3-phosphocholineReach from here →
  1. a 2-acyl-sn-glycero-3-phosphocholine + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phosphocholine + CoA
  2. a 2-acyl-sn-glycero-3-phosphocholine + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phosphocholine + CoA
  3. 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine + a 2-acyl-sn-glycero-3-phosphocholine = a 1-hexadecanoyl-2-acyl-sn-glycero-3-phosphocholine + 2-hexadecanoyl-sn-glycero-3-phosphocholine

  Catalysed by LPGAT1, PLAAT1One of 2 routes

• 2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholineReach from here →
  1. acyl-CoA pool formation and breakdown
  2. 2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine + octadecanoyl-CoA = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + CoA
  3. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-octadecanoyl-N-(acetyl)-sphing-4-enine + 2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine

  Catalysed by LPGAT1, PLA2G15cytosolOne of 2 routes

• 1-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-N-(acetyl)-sphing-4-enineReach from here →
  1. acyl-CoA pool formation and breakdown
  2. 2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine + octadecanoyl-CoA = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + CoA
  3. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-N-(acetyl)-sphing-4-enine + 1-octadecanoyl-sn-glycero-3-phosphocholine

  Catalysed by LPGAT1, PLA2G15cytosol

• 2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholineReach from here →
  1. acyl-CoA pool formation and breakdown
  2. (9Z,12Z)-octadecadienoyl-CoA + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine + CoA
  3. 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine + 1-hexadecanoyl-N-(acetyl)-sphing-4-enine

  Catalysed by LPCAT3, MBOAT2, LPCAT1, PLA2G15cytosolOne of 4 routes

• 2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. acyl-CoA pool formation and breakdown
  2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 1-hexadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholine + CoA
  3. 1-hexadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholine + 1-hexadecanoyl-N-(acetyl)-sphing-4-enine

  Catalysed by LPCAT1, PLA2G15cytosolOne of 3 routes

• 1-(9Z,12Z-octadecadienoyl)-N-acetylsphing-4-enineReach from here →
  1. acyl-CoA pool formation and breakdown
  2. (9Z,12Z)-octadecadienoyl-CoA + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine + CoA
  3. 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-(9Z,12Z-octadecadienoyl)-N-acetylsphing-4-enine + 1-hexadecanoyl-sn-glycero-3-phosphocholine

  Catalysed by LPCAT3, MBOAT2, LPCAT1, PLA2G15cytosolOne of 2 routes

• 1-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-N-(acetyl)-sphing-4-enineReach from here →
  1. acyl-CoA pool formation and breakdown
  2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 1-hexadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholine + CoA
  3. 1-hexadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-N-(acetyl)-sphing-4-enine + 1-hexadecanoyl-sn-glycero-3-phosphocholine

  Catalysed by LPCAT1, PLA2G15cytosol

• a 1-O-alkyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. Acyl-CoA:1-acyl-sn-glycero-3-phosphoethanolamine O-acyltransferase
  2. L-1-phosphatidylethanolamine:L-serine phosphatidyltransferase
  3. a 1-O-alkyl-sn-glycero-3-phosphoethanolamine + H2O = a 1-O-alkyl-sn-glycero-3-phosphate + ethanolamine + H(+)

  Catalysed by LPCAT4, LPCAT3, LPCAT2, LPCAT1 and 3 morecytosol

• hexadecanedioateReach from here →
  1. acyl-CoA:sn-glycerol-3-phosphate 1-O-acyltransferase
  2. Production of Hexadecanedioylcarnitine
  3. hexadecanedioyl-CoA + H2O = hexadecanedioate + CoA + H(+)

  Catalysed by GPAT3, GPAT2, GPAT4, GPAM and 4 moremitochondrial matrix, cytosol

• docosanedioateReach from here →
  1. acyl-CoA pool formation and breakdown
  2. Docosanoyl-CoA hydrolase
  3. Fatty Acid Omega Oxidation by Hydroxylases (C22->C22Dc), Endoplasmatic Reticulum

  Catalysed by BAAT, ACOT6, CYP4F2, CYP4F3cytosol, endoplasmic reticulum

• 3-oxo-(13Z)-eicosenoyl-CoAReach from here →
  1. acyl-CoA:sn-glycerol-3-phosphate 1-O-acyltransferase
  2. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix
  3. (11Z)-octadecenoyl-CoA + malonyl-CoA + H(+) = 3-oxo-(13Z)-eicosenoyl-CoA + CO2 + CoA

  Catalysed by GPAT3, GPAT2, GPAT4, GPAM and 4 moremitochondrial matrix, cytosol

• (25R)-cholest-5-ene-3beta,26-diolReach from here →
  1. an acyl-CoA + cholesterol = a cholesterol ester + CoA
  2. a cholesterol ester + H2O = cholesterol + a fatty acid + H(+)
  3. 2 reduced [adrenodoxin] + cholesterol + O2 + 2 H(+) = (25R)-cholest-5-ene-3beta,26-diol + 2 oxidized [adrenodoxin] + H2O

  Catalysed by SOAT2, SOAT1, CES1, LIPN and 3 more

• 24-hydroxytetracosanoateReach from here →
  1. acyl-CoA pool formation and breakdown
  2. Tetracosenoyl-CoA hydrolase
  3. tetracosanoate + reduced [NADPH--hemoprotein reductase] + O2 = 24-hydroxytetracosanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by BAAT, THEM4, CYP4F2, CYP4F3cytosol

• 20-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. acyl-CoA pool formation and breakdown
  2. Arachidonyl-CoA hydrolase
  3. arachidonic acid:oxygen 1-oxidoreductase

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 28 morecytosolOne of 3 routes

• 11,12-epoxy-(5Z,8Z,14Z)-eicosatrienoateReach from here →
  1. acyl-CoA pool formation and breakdown
  2. Arachidonyl-CoA hydrolase
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = 11,12-epoxy-(5Z,8Z,14Z)-eicosatrienoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 2 morecytosol

• 19-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. acyl-CoA pool formation and breakdown
  2. Arachidonyl-CoA hydrolase
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = 19-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 6 morecytosol

• 11-hydroxydodecanoateReach from here →
  1. acyl-CoA pool formation and breakdown
  2. Lauroyl-CoA hydrolase
  3. lauric acid[r] + O2[r] + FMNH2[r] = FMN[r] + H2O[r] + 11-hydroxydodecanoate[r]

  Catalysed by ACOT7, BAAT, ACOT1, ACOT13 and 1 morecytosol, endoplasmic reticulumOne of 3 routes

• (17R,18S)-epoxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. acyl-CoA pool formation and breakdown
  2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  3. (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. acyl-CoA pool formation and breakdown
  2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  3. (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. acyl-CoA pool formation and breakdown
  2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  3. 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. acyl-CoA pool formation and breakdown
  2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  3. (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

• 22-hydroxy-(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoateReach from here →
  1. acyl-CoA pool formation and breakdown
  2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA hydrolase
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + reduced [NADPH--hemoprotein reductase] + O2 = 22-hydroxy-(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by BAAT, ACOT6, CYP4F2, CYP4F3 and 2 morecytosol

• 14-hydroxytetradecanoateReach from here →
  1. acyl-CoA pool formation and breakdown
  2. Myristoyl-CoA hydrolase
  3. alkane 1-monooxygenase (myristic acid)

  Catalysed by ACOT7, BAAT, THEM4, ACOT1 and 3 morecytosolOne of 2 routes

• 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphateReach from here →
  1. acyl-CoA:sn-glycerol-3-phosphate 1-O-acyltransferase
  2. 1-acylglycerol-3-phosphate pool formation and breakdown
  3. 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

  Catalysed by GPAT3, GPAT2, GPAT4, GPAM and 1 moremitochondrial matrix, cytosolOne of 2 routes

• 1-octadecanoyl-2-(9Z,12Z)-octadecadienoyl-sn-glycerolReach from here →
  1. acyl-CoA pool formation and breakdown
  2. 1-octadecanoyl-sn-glycero-3-phosphate + (9Z,12Z)-octadecadienoyl-CoA = 1-octadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphate + CoA
  3. 1-octadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphate + H2O = 1-octadecanoyl-2-(9Z,12Z)-octadecadienoyl-sn-glycerol + phosphate

  Catalysed by AGPAT4, LPIN1cytosol

• 1-octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycerolReach from here →
  1. acyl-CoA pool formation and breakdown
  2. 1-octadecanoyl-sn-glycero-3-phosphate + (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA = 1-octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphate + CoA
  3. 1-octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphate + H2O = 1-octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycerol + phosphate

  Catalysed by AGPAT4, LPIN1cytosolOne of 2 routes

• 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphateReach from here →
  1. an acyl-CoA + cholesterol = a cholesterol ester + CoA
  2. a cholesterol ester + H2O = cholesterol + a fatty acid + H(+)
  3. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(out) + cholesterol(in) = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(in) + cholesterol(out)

  Catalysed by SOAT2, SOAT1, CES1, LIPN and 3 moreinner side of the membrane, outer side of the membraneOne of 2 routes

• 2,6,10,14-tetramethylpentadecanoateReach from here →
  1. acyl-CoA:sn-glycerol-3-phosphate 1-O-acyltransferase
  2. fatty-acid-CoA ligase
  3. peroxisomal acyl-CoA thioesterase

  Catalysed by GPAT3, GPAT2, GPAT4, GPAM and 2 moremitochondrial matrix, cytosol, peroxisomeOne of 2 routes

• a 1-O-(1Z-alkenyl)-sn-glycero-3-phosphateReach from here →
  1. a 1-O-(1Z-alkenyl)-sn-glycero-3-phosphocholine + an acyl-CoA = a 1-O-(1Z-alkenyl)-2-acyl-sn-glycero-3-phosphocholine + CoA
  2. a 1-O-(1Z-alkenyl)-sn-glycero-3-phosphocholine + an acyl-CoA = a 1-O-(1Z-alkenyl)-2-acyl-sn-glycero-3-phosphocholine + CoA
  3. a 1-O-(1Z-alkenyl)-sn-glycero-3-phosphocholine + H2O = a 1-O-(1Z-alkenyl)-sn-glycero-3-phosphate + choline + H(+)

  Catalysed by LPCAT2, LPCAT1, ENPP2

• 1-O-(1Z)-alkenyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. acyl-CoA pool formation and breakdown
  2. octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O
  3. a 1-O-(1Z-alkenyl)-sn-glycero-3-phosphoethanolamine + (9Z)-octadecenoyl-CoA = 1-O-(1Z)-alkenyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphoethanolamine + CoA

  Catalysed by SCD, SCD5, LPCAT4, MBOAT1 and 1 morecytosolOne of 2 routes