(5Z,8Z,11Z,14Z)-eicosatetraenoate

Three steps

• thio-Mo-molybdopterinReach from here →
  1. transport of arachidonate and GSH (cytosol to extracellular)
  2. cystine to cysteine conversion
  3. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O

  Catalysed by MOCOSextracellular space, cytosolOne of 3 routes

• glycodeoxycholateReach from here →
  1. N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycine + H2O = (5Z,8Z,11Z,14Z)-eicosatetraenoate + glycine
  2. N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycine + H2O = (5Z,8Z,11Z,14Z)-eicosatetraenoate + glycine
  3. Glycodeoxycholate amidohydrolase

  Catalysed by FAAH, PM20D1cytosolOne of 2 routes

• 14-hydroperoxy-(4Z,7Z,10Z,12E,16Z,19Z)-docosahexaenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  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 ALOX12Bcytosol, extracellular space

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

  Catalysed by ALDH3A2cytosol, extracellular space

• (5Z)-tetradecenoyl-CoAReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (physeteric acid)

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

• (3E)-decenoyl-CoAReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. Fatty Acid Beta Oxidation (C12:1->C10:1), Mitochondrial

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 13 morecytosol, mitochondrial matrix

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

  Catalysed by CYP4Z1cytosol, extracellular space

• 2-glyceryl-prostaglandin H2Reach from here →
  1. fatty acid amide hydrolase (2-arachidonoylglycerol)
  2. 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + 2 O2 = 2-glyceryl-prostaglandin G2
  3. 2-glyceryl-prostaglandin G2 + AH2 = 2-glyceryl-prostaglandin H2 + A + H2O

  Catalysed by FAAH, PTGS2cytosolOne of 2 routes

• 11beta-prostaglandin F2Reach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. transport of prostaglandin D2 (cytosol to extracellular)
  3. prostaglandin D2 + NADPH + H(+) = 11beta-prostaglandin F2 + NADP(+)

  Catalysed by SLCO1B1, AKR1C3, AKR1C2extracellular space, cytosol

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

  Catalysed by ASAH1cytosol, extracellular space

• N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + ATP + CoA = (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + AMP + diphosphate
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + CoA
  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 SLC27A2, ACSL4, ACSL3, ACSL1 and 10 more

• 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-cytidine-5'-diphosphateReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + ATP + CoA = (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + AMP + diphosphate
  2. 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
  3. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate + CTP + H(+) = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-cytidine-5'-diphosphate + diphosphate

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 more

• 1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-cytidine-5'-diphosphateReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + ATP + CoA = (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + AMP + diphosphate
  2. 1-hexadecanoyl-sn-glycero-3-phosphate + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate + CoA
  3. 1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate + CTP + H(+) = 1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-cytidine-5'-diphosphate + diphosphate

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 11 more

• N-tetradecanoylglycineReach from here →
  1. arachidonate to 8-peroxy-(5Z,9E,11Z,14Z)-eicosatetraenoate conversion
  2. 8-peroxy-(5Z,9E,11Z,14Z)... to 5,9-cyclo-6,8-cycloperoxy-12... conversion
  3. N-tetradecanoylglycine + 2 L-ascorbate + O2 = N-tetradecanoyl-(2S)-hydroxyglycine + 2 monodehydro-L-ascorbate radical + H2O

  Catalysed by PAMcytosolOne of 2 routes

• (2R,6)-dimethylheptanoyl-CoAReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. acetyl-CoA C-acyltransferase (3-oxo-4(R),8-dimethyl-nonanoyl-CoA)

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

• N-eicosanoylglycinateReach from here →
  1. N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycine + H2O = (5Z,8Z,11Z,14Z)-eicosatetraenoate + glycine
  2. N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycine + H2O = (5Z,8Z,11Z,14Z)-eicosatetraenoate + glycine
  3. eicosanoyl-CoA + glycine = N-eicosanoylglycinate + CoA + H(+)

  Catalysed by FAAH, PM20D1, BAAT

• N-docosanoylglycineReach from here →
  1. N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycine + H2O = (5Z,8Z,11Z,14Z)-eicosatetraenoate + glycine
  2. N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycine + H2O = (5Z,8Z,11Z,14Z)-eicosatetraenoate + glycine
  3. docosanoyl-CoA + glycine = N-docosanoylglycine + CoA + H(+)

  Catalysed by FAAH, PM20D1, BAAT

• N-hexacosanoylglycineReach from here →
  1. N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycine + H2O = (5Z,8Z,11Z,14Z)-eicosatetraenoate + glycine
  2. N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycine + H2O = (5Z,8Z,11Z,14Z)-eicosatetraenoate + glycine
  3. hexacosanoyl-CoA + glycine = N-hexacosanoylglycine + CoA + H(+)

  Catalysed by FAAH, PM20D1, BAAT

• 16alpha-hydroxydehydroepiandrosterone 3-sulfateReach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. transport of dehydroepiandrosterone sulfate (cytosol to extracellular)
  3. dehydroepiandrosterone 3-sulfate + reduced [NADPH--hemoprotein reductase] + O2 = 16alpha-hydroxydehydroepiandrosterone 3-sulfate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by SLCO1B1, CYP3A7extracellular space, cytosol

• an N(2)-acyl-L-glutamineReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. acyl-CoA pool formation and breakdown
  3. an acyl-CoA + L-glutamine = an N(2)-acyl-L-glutamine + CoA + H(+)

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

• (7Z)-hexadecenoyl-CoAReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (7-palmitoleic acid)

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

• tricosanoyl-CoAReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. Arachidonyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (tricosanoic acid)

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

• a 3-oxoacyl-CoAReach from here →
  1. Arachidonate:CoA ligase (AMP-forming)
  2. acyl-CoA pool formation and breakdown
  3. an acyl-CoA + acetyl-CoA = a 3-oxoacyl-CoA + CoA

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

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

  Catalysed by ALOX12cytosol, extracellular space

• prostaglandin H1Reach from here →
  1. transport of arachidonate (cytosol to extracellular)
  2. transport of prostaglandin E1 (cytosol to extracellular)
  3. prostaglandin-E synthase (prostaglandin E1)

  Catalysed by SLCO1B1, PTGES, PTGES3, PTGES2extracellular space, cytosolOne of 3 routes

• (5S,11R)-dihydroxy-(6E,8Z,12E,14Z)-eicosatetraenoateReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (5S)-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate
  2. (5S)-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + 2 glutathione = (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + glutathione disulfide + H2O
  3. (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (5S,11R)-dihydroxy-(6E,8Z,12E,14Z)-eicosatetraenoate + A + H2O

  Catalysed by ALOX5, PTGES, MGST3, GPX1 and 4 moreOne of 2 routes

• (5S,15R)-dihydroxy-(6E,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (5S)-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate
  2. (5S)-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + 2 glutathione = (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + glutathione disulfide + H2O
  3. (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (5S,15R)-dihydroxy-(6E,8Z,11Z,13E)-eicosatetraenoate + A + H2O

  Catalysed by ALOX5, PTGES, MGST3, GPX1 and 4 moreOne of 2 routes

• (5S,15S)-dihydroxy-(6E,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (5S)-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate
  2. (5S)-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + 2 glutathione = (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + glutathione disulfide + H2O
  3. (5S)-hydroxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (5S,15S)-dihydroxy-(6E,8Z,11Z,13E)-eicosatetraenoate + A + H2O

  Catalysed by ALOX5, PTGES, MGST3, GPX1 and 4 moreOne of 2 routes

• 17R-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  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 PTGS2cytosol, extracellular spaceOne of 2 routes

• 13-hydroxy-(4Z,7Z,10Z,14E,16Z,19Z)-docosahexaenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  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 PTGS2cytosol, extracellular spaceOne of 2 routes

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

  Catalysed by PTGS1, PTGS2cytosol, extracellular spaceOne of 3 routes

• (15R)-hydroxy-(5Z,8Z,11Z,13E,17Z)-eicosapentaenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  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 PTGS2cytosol, extracellular spaceOne of 2 routes

• (11R)-hydroxy-(5Z,8Z,12E,14Z,17Z)-eicosapentaenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  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 PTGS2cytosol, extracellular spaceOne of 2 routes

• 13R-hydroxy-(7Z,10Z,14E,16Z,19Z)-docosapentaenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  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 PTGS2cytosol, extracellular spaceOne of 2 routes

• (13S)-hydroxy-(9Z,11E)-octadecadienoateReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. (9Z,12Z)-octadecadienoate + AH2 + O2 = (13S)-hydroxy-(9Z,11E)-octadecadienoate + A + H2O

  Catalysed by PTGS1, PTGS2, AIFM1, PYROXD1