eicosanoate

Three steps

• 2-hydroxyoctadecanoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (eicosanoate)
  2. Beta Oxidation of Long Chain Fatty Acid
  3. octadecanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxyoctadecanoyl-CoA + succinate + CO2

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosol, mitochondrial matrix

• (15Z)-tetracosenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (eicosanoate)
  2. Eicosanoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (nervonic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 9 routes

• (17Z)-hexacosenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (eicosanoate)
  2. Eicosanoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (ximenic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 7 routes

• (8Z,11Z,14Z)-eicosatrienoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (eicosanoate)
  2. Eicosanoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 8 routes

• (8Z,11Z,14Z,17Z)-eicosatetraenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (eicosanoate)
  2. Eicosanoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (omega-3-arachidonic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 6 routes

• (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (eicosanoate)
  2. Eicosanoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (DHA)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 11 routes

• heptadecanoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (eicosanoate)
  2. Eicosanoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (margaric acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 7 routes

• (9Z)-heptadecenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (eicosanoate)
  2. Eicosanoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (9-heptadecylenic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 6 routes

• (11Z,14Z,17Z)-eicosatrienoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (eicosanoate)
  2. Eicosanoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase ((11Z,14Z,17Z)-eicosatrienoic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 6 routes

• N-(15Z-tetracosenoyl)-sphing-4-enineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. N-(15Z-tetracosenoyl)-sphing-4-enine + H2O = (15Z)-tetracosenoate + sphing-4-enine

  Catalysed by ACER2, ACER1, ASAH2cytosol, extracellular space

• 1-(9Z-octadecenoyl)-2-octadecanoyl-sn-glycero-3-phosphateReach from here →
  1. long-chain-fatty-acid-CoA ligase (eicosanoate)
  2. Beta Oxidation of Long Chain Fatty Acid
  3. 1-(9Z-octadecenoyl)-sn-glycero-3-phosphate + octadecanoyl-CoA = 1-(9Z-octadecenoyl)-2-octadecanoyl-sn-glycero-3-phosphate + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 12 morecytosol, mitochondrial matrix

• 1-octadecanoyl-sn-glycero-3-phosphateReach from here →
  1. long-chain-fatty-acid-CoA ligase (eicosanoate)
  2. Beta Oxidation of Long Chain Fatty Acid
  3. glycerol-3-phosphate 1-O-acyltransferase (sn-glycerol-3-phosphate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosol, mitochondrial matrixOne of 2 routes

• 1-(9Z-octadecenoyl)-2-octadecanoyl-sn-glycero-3-phospho-L-serineReach from here →
  1. long-chain-fatty-acid-CoA ligase (eicosanoate)
  2. Beta Oxidation of Long Chain Fatty Acid
  3. 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-L-serine + octadecanoyl-CoA = 1-(9Z-octadecenoyl)-2-octadecanoyl-sn-glycero-3-phospho-L-serine + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosol, mitochondrial matrix

• 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. long-chain-fatty-acid-CoA ligase (eicosanoate)
  2. Beta Oxidation of Long Chain Fatty Acid
  3. 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

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosol, mitochondrial matrix

• 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. long-chain-fatty-acid-CoA ligase (eicosanoate)
  2. Beta Oxidation of Long Chain Fatty Acid
  3. 2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + octadecanoyl-CoA = 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosol, mitochondrial matrix

• 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. long-chain-fatty-acid-CoA ligase (eicosanoate)
  2. Beta Oxidation of Long Chain Fatty Acid
  3. 2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + octadecanoyl-CoA = 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosol, mitochondrial matrix

• nonadecanoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (eicosanoate)
  2. Eicosanoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (nonadecylic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 7 routes

• (11Z)-octadecenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (eicosanoate)
  2. Eicosanoyl-CoA hydrolase
  3. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosolOne of 4 routes

• 1'-[1-acyl-2-octadecanoyl-sn-glycero-3-phospho],3'-[1-acyl,2-hydroxy-sn-glycero-3-phospho]-glycerolReach from here →
  1. long-chain-fatty-acid-CoA ligase (eicosanoate)
  2. Beta Oxidation of Long Chain Fatty Acid
  3. 1',3'-bis-[1-acyl-sn-glycero-3-phospho]-glycerol + octadecanoyl-CoA = 1'-[1-acyl-2-octadecanoyl-sn-glycero-3-phospho],3'-[1-acyl,2-hydroxy-sn-glycero-3-phospho]-glycerol + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosol, mitochondrial matrix

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

  Catalysed by ALOX12Bcytosol, extracellular space

• 1-acyl-2-octadecanoyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. long-chain-fatty-acid-CoA ligase (eicosanoate)
  2. Beta Oxidation of Long Chain Fatty Acid
  3. a 1-acyl-sn-glycero-3-phosphoethanolamine + octadecanoyl-CoA = 1-acyl-2-octadecanoyl-sn-glycero-3-phosphoethanolamine + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosol, mitochondrial matrix

• (8S)-hydroperoxy-(5Z,9E,11Z,14Z)-eicosatetraenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. Arachidonate:oxygen 8-oxidoreductase

  Catalysed by ALOX12cytosol, extracellular spaceOne of 2 routes

• 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycerolReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycerol + H2O = 2-(9Z-octadecenoyl)-glycerol + octadecanoate + H(+)

  Catalysed by ABHD11cytosol, extracellular space

• a 2,3-diacyl-sn-glycerolReach from here →
  1. long-chain-fatty-acid-CoA ligase (eicosanoate)
  2. acyl-CoA pool formation and breakdown
  3. a 2-acylglycerol + an acyl-CoA = a 2,3-diacyl-sn-glycerol + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosol

• 1-octadecanoyl-2-(9Z-octadecenoyl)-glycerolReach from here →
  1. long-chain-fatty-acid-CoA ligase (eicosanoate)
  2. Beta Oxidation of Long Chain Fatty Acid
  3. 2-(9Z-octadecenoyl)-glycerol + octadecanoyl-CoA = 1-octadecanoyl-2-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosol, mitochondrial matrix

• 1-O-eicosanyl (9Z)-octadecenoateReach from here →
  1. long-chain-fatty-acid-CoA ligase (eicosanoate)
  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 SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosol

• hexadecyl octadecanoateReach from here →
  1. long-chain-fatty-acid-CoA ligase (eicosanoate)
  2. Beta Oxidation of Long Chain Fatty Acid
  3. hexadecan-1-ol + octadecanoyl-CoA = hexadecyl octadecanoate + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosol, mitochondrial matrix

• 2-O-(5Z,8Z,11Z,14Z)-eicosatetraenylglycerolReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. fatty acid amide hydrolase (arachidonate)

  Catalysed by FAAHcytosol, extracellular space

• (R)-2-hydroxytetracosanoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. tetracosanoate + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (R)-2-hydroxytetracosanoate + 2 Fe(III)-[cytochrome b5] + H2O

  Catalysed by FA2Hcytosol, extracellular space

• 1-O-alkyl-3-acylglycerolReach from here →
  1. long-chain-fatty-acid-CoA ligase (eicosanoate)
  2. acyl-CoA pool formation and breakdown
  3. 1-O-alkylglycerol + an acyl-CoA = 1-O-alkyl-3-acylglycerol + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosol

• docosanedioateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. Fatty Acid Omega Oxidation by Hydroxylases (C22->C22Dc), Endoplasmatic Reticulum

  Catalysed by CYP4F2, CYP4F3cytosol, extracellular space, endoplasmic reticulum

• dodecanedioyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (eicosanoate)
  2. Eicosanoyl-CoA hydrolase
  3. Activation of dodecanedioic acid

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 4 routes

• decanedioyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (eicosanoate)
  2. Eicosanoyl-CoA hydrolase
  3. Production of Sebacoylcarnitine

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosolOne of 4 routes

• octanedioyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (eicosanoate)
  2. Eicosanoyl-CoA hydrolase
  3. Production of Suberylcarnitine

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosolOne of 4 routes

• hexanedioyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (eicosanoate)
  2. Eicosanoyl-CoA hydrolase
  3. Activation of adipic acid for Formation of Adipoyl Carnitine

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 4 routes

• (4Z,7Z,10Z,13Z,16Z)-docosapentaenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (eicosanoate)
  2. Eicosanoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase ((4Z,7Z,10Z,13Z,16Z)-DPA)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 8 routes

• (11Z,14Z)-eicosadienoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (eicosanoate)
  2. Eicosanoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase ((11Z,14Z)-eicosadienoic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 8 routes

• (R)-3-hydroxy-(11Z)-octadecenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (eicosanoate)
  2. Eicosanoyl-CoA hydrolase
  3. Production of 3-Hydroxyoctadecenoylcarnitinec

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosolOne of 2 routes

• (13Z)-eicosenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (eicosanoate)
  2. Eicosanoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase ((13Z)-eicosenoic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 6 routes

• 24-hydroxytetracosanoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. tetracosanoate + reduced [NADPH--hemoprotein reductase] + O2 = 24-hydroxytetracosanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CYP4F2, CYP4F3cytosol, extracellular space

• 20-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. arachidonic acid:oxygen 1-oxidoreductase

  Catalysed by CYP1A1, CYP1A2, CYP2E1, CYP3A4 and 23 morecytosol, extracellular spaceOne of 3 routes

• 11,12-epoxy-(5Z,8Z,14Z)-eicosatrienoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  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 CYP2C9cytosol, extracellular space

• 19-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  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 CYP1A1, CYP1A2, CYP2C9, CYP2C19 and 1 morecytosol, extracellular space

• 11-hydroxydodecanoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. lauric acid[r] + O2[r] + FMNH2[r] = FMN[r] + H2O[r] + 11-hydroxydodecanoate[r]

  Catalysed by CYP2E1cytosol, extracellular space, endoplasmic reticulumOne of 3 routes

• (17R,18S)-epoxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  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 CYP1A1, CYP1A2, CYP3A4, CYP2C8 and 3 morecytosol, extracellular space

• (17S,18R)-epoxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  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 CYP2C8, CYP2D6, CYP2J2cytosol, extracellular space

• 19-hydroxy-(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. EPA[r] + O2[r] + FMNH2[r] = FMN[r] + H2O[r] + 19-hydroxy-(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate[r]

  Catalysed by CYP2E1cytosol, extracellular space, endoplasmic reticulumOne of 3 routes

• 20-hydroxy-(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  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 CYP4F2, CYP4F3, CYP4V2cytosol, extracellular space

• 22-hydroxy-(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  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 CYP4F2, CYP4F3, CYP4V2, CYP4F11cytosol, extracellular space

• 14-hydroxytetradecanoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. alkane 1-monooxygenase (myristic acid)

  Catalysed by CYP4A11, CYP4A22cytosol, extracellular spaceOne of 2 routes