(15Z)-tetracosenoate

Three steps

• N-tetracosanoyl-sphing-4-enineReach from here →
  1. N-(15Z-tetracosenoyl)-sphing-4-enine + H2O = (15Z)-tetracosenoate + sphing-4-enine
  2. N-(15Z-tetracosenoyl)-sphing-4-enine + H2O = (15Z)-tetracosenoate + sphing-4-enine
  3. tetracosanoyl-CoA + sphing-4-enine = N-tetracosanoyl-sphing-4-enine + CoA + H(+)

  Catalysed by ACER2, ACER1, ASAH2, CERS2

• 1-hexadecanoyl-sn-glycero-3-phosphocholineReach from here →
  1. N-(15Z-tetracosenoyl)-sphing-4-enine + H2O = (15Z)-tetracosenoate + sphing-4-enine
  2. beta-D-glucosyl-(1<->1')-N-(15Z-tetracosenoyl)-sphing-4-enine + cholesterol = N-(15Z-tetracosenoyl)-sphing-4-enine + cholesteryl 3-beta-D-glucoside
  3. 1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + cholesterol = cholesteryl (5Z,8Z,11Z,14Z)-eicosatetraenoate + 1-hexadecanoyl-sn-glycero-3-phosphocholine

  Catalysed by ACER2, ACER1, ASAH2, GBA1 and 1 moreOne of 9 routes

• (7Z,10Z,13Z,16Z)-docosatetraenoyl-CoAReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. (7Z,10Z,13Z,16Z)-docosatetraenoate + ATP + CoA = (7Z,10Z,13Z,16Z)-docosatetraenoyl-CoA + AMP + diphosphate

  Catalysed by ACSL4cytosol, extracellular space

• (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (EPA)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosolOne of 13 routes

• (7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (DPA)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosolOne of 9 routes

• (9Z,12Z,15Z)-octadecatrienoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (linolenate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosolOne of 10 routes

• (13Z)-docosenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (cis-erucic acid)

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

• (11Z)-eicosenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (cis-gondoic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosolOne of 10 routes

• (9Z,12Z,15Z,18Z,21Z)-tetracosapentaenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase ((9Z,12Z,15Z,18Z,21Z)-TPA)

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

• (6Z,9Z,12Z,15Z,18Z,21Z)-tetracosahexaenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase ((6Z,9Z,12Z,15Z,18Z,21Z)-THA)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosolOne of 5 routes

• (17Z)-hexacosenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (ximenic acid)

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

• (8Z,11Z,14Z)-eicosatrienoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosolOne of 8 routes

• (8Z,11Z,14Z,17Z)-eicosatetraenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (omega-3-arachidonic acid)

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

• (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (DHA)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosolOne of 11 routes

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

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

• (9Z)-heptadecenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (9-heptadecylenic acid)

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

• (11Z,14Z,17Z)-eicosatrienoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase ((11Z,14Z,17Z)-eicosatrienoic acid)

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

• N-(tetracosenoyl)-sphing-4-enineReach from here →
  1. N-(15Z-tetracosenoyl)-sphing-4-enine + H2O = (15Z)-tetracosenoate + sphing-4-enine
  2. N-(15Z-tetracosenoyl)-sphing-4-enine + H2O = (15Z)-tetracosenoate + sphing-4-enine
  3. tetracosenoyl-CoA + sphing-4-enine = N-(tetracosenoyl)-sphing-4-enine + CoA + H(+)

  Catalysed by ACER2, ACER1, ASAH2, CERS2

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

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

• (11Z)-octadecenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. Transport of 11-Octadecenoyl Carnitine into the Mitochondrial Matrix

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 3 routes

• (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

• (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 (nervonic acid)
  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

• 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 (nervonic acid)
  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 (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. Activation of dodecanedioic acid

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosolOne of 4 routes

• decanedioyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. Production of Sebacoylcarnitine

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 4 routes

• octanedioyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. Production of Suberylcarnitine

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosolOne of 4 routes

• hexanedioyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. Activation of adipic acid for Formation of Adipoyl Carnitine

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosolOne of 4 routes

• (4Z,7Z,10Z,13Z,16Z)-docosapentaenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase ((4Z,7Z,10Z,13Z,16Z)-DPA)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosolOne of 8 routes

• (11Z,14Z)-eicosadienoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase ((11Z,14Z)-eicosadienoic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 6 morecytosolOne of 8 routes

• (R)-3-hydroxy-(11Z)-octadecenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. Production of 3-Hydroxyoctadecenoylcarnitinec

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 9 morecytosol

• (13Z)-eicosenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase ((13Z)-eicosenoic acid)

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

• (25R)-cholest-5-ene-3beta,26-diolReach from here →
  1. N-(15Z-tetracosenoyl)-sphing-4-enine + H2O = (15Z)-tetracosenoate + sphing-4-enine
  2. beta-D-glucosyl-(1<->1')-N-(15Z-tetracosenoyl)-sphing-4-enine + cholesterol = N-(15Z-tetracosenoyl)-sphing-4-enine + cholesteryl 3-beta-D-glucoside
  3. 2 reduced [adrenodoxin] + cholesterol + O2 + 2 H(+) = (25R)-cholest-5-ene-3beta,26-diol + 2 oxidized [adrenodoxin] + H2O

  Catalysed by ACER2, ACER1, ASAH2, GBA1 and 1 more

• 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

• 4,8-dimethylnonanoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. Carnitine Dimethyl Nonanoyl Transferase, Revsible, Peroxisomal

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosol, peroxisomeOne of 3 routes

• tetradecanedioyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (nervonic acid)
  2. (15Z)-tetracosenoyl-CoA hydrolase
  3. Fatty Acid Beta Oxidation (C16Dc->C14Dc), Peroxisomal

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosol, peroxisome