(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate

Three steps

• sphing-4-enineReach from here →
  1. long-chain-fatty-acid-CoA ligase (EPA)
  2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  3. acyl-CoA:sphingosine N-acyltransferase

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 11 morecytosol, Golgi apparatusOne of 2 routes

• sphinganineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. N-acylsphingosine amidohydrolase
  3. an N-acylsphinganine + H2O = sphinganine + a fatty acid

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 1 morecytosol

• spermidineReach from here →
  1. long-chain-fatty-acid-CoA ligase (EPA)
  2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  3. diamine N-acetyltransferase (N1-acetylspermidine)

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

• L-methionineReach from here →
  1. long-chain-fatty-acid-CoA ligase (EPA)
  2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  3. N-acetylglutamate synthase (N-acetylmethionine)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosol, mitochondrial matrixOne of 11 routes

• a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol)Reach from here →
  1. long-chain-fatty-acid-CoA ligase (EPA)
  2. acyl-CoA pool formation and breakdown
  3. a 1-acyl-sn-glycero-3-phospho-(1D-myo-inositol) + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol) + CoA

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

• L-tryptophanReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. transport of cysteine and tryptophan (cytosol to extracellular)

  Catalysed by PTGS2, MOCOS, SLC7A5extracellular space, cytosolOne of 4 routes

• glutathioneReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + O2 = (12S)-hydroperoxy-(5Z,8Z,10E,14Z,17Z)-eicosapentaenoate
  2. (12S)-hydroperoxy-(5Z,8Z,10E,14Z,17Z)-eicosapentaenoate + 2 glutathione = (12S)-hydroxy-(5Z,8Z,10E,14Z,17Z)-eicosapentaenoate + glutathione disulfide + H2O
  3. 2 glutathione + NADP(+) = glutathione disulfide + NADPH + H(+)

  Catalysed by ALOX12, GPX1, GPX4, GSROne of 4 routes

• a 1-acyl-sn-glycero-3-phosphateReach from here →
  1. long-chain-fatty-acid-CoA ligase (EPA)
  2. acyl-CoA pool formation and breakdown
  3. sn-glycerol 3-phosphate + an acyl-CoA = a 1-acyl-sn-glycero-3-phosphate + CoA

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

• L-alanineReach from here →
  1. long-chain-fatty-acid-CoA ligase (EPA)
  2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  3. amino-acid N-acetyltransferase (N-acetyl-L-alanine)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosol, mitochondrial matrixOne of 18 routes

• L-asparagineReach from here →
  1. long-chain-fatty-acid-CoA ligase (EPA)
  2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  3. N-acetylglutamate synthase (N-acetyl-L-asparagine)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosol, mitochondrial matrixOne of 5 routes

• L-phenylalanineReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. transport of cysteine and phenylalanine (cytosol to extracellular)

  Catalysed by PTGS2, MOCOS, SLC7A5extracellular space, cytosolOne of 6 routes

• L,L-cystathionineReach from here →
  1. long-chain-fatty-acid-CoA ligase (EPA)
  2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  3. N-acetylglutamate synthase (N-acetyl-L-cystathionine)

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

• gamma-L-glutamyl-L-cysteineReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. L-glutamate:L-cysteine gamma-ligase (ADP-forming)

  Catalysed by PTGS2, MOCOS, GCLC, GCLMcytosolOne of 2 routes

• (3Z)-dodecenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (EPA)
  2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  3. acetyl-CoA C-acyltransferase (3-oxomyrist-5-enoyl-CoA)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 10 morecytosol, mitochondrial matrixOne of 3 routes

• S-sulfanyl-L-cysteineReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. 2 L-cysteine = S-sulfanyl-L-cysteine + L-alanine

  Catalysed by PTGS2, MOCOS, CARS2

• a 1,2-diacyl-sn-glycero-3-phosphateReach from here →
  1. long-chain-fatty-acid-CoA ligase (EPA)
  2. acyl-CoA pool formation and breakdown
  3. a 1-acyl-sn-glycero-3-phosphate + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phosphate + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 17 morecytosol

• (25R)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (EPA)
  2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  3. 3alpha,7alpha,12alpha-trihydroxy-5beta-cholestanoate:CoA ligase (AMP-forming)

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

• phosphoenolpyruvateReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O
  2. (R)-malate + A = oxaloacetate + AH2
  3. oxaloacetate + GTP = phosphoenolpyruvate + GDP + CO2

  Catalysed by PTGS2, D2HGDH, PCK1, PCK2

• deoxycholoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (EPA)
  2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  3. cholate-CoA ligase (3alpha,12alpha-dihydroxy-5beta-cholanate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosolOne of 4 routes

• N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycine + H2O = (5Z,8Z,11Z,14Z)-eicosatetraenoate + glycine

  Catalysed by FAAH, PM20D1cytosol, extracellular space

• N-[(R)-4-phosphopantothenoyl]-L-cysteineReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. (R)-4'-phosphopantothenate:L-cysteine ligase

  Catalysed by PTGS2, MOCOS, PPCScytosolOne of 4 routes

• (9S)-hydroperoxy-(10E,12Z)-octadecadienoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. linoleate:oxygen 9-oxidoreductase

  No catalyst recordedcytosol, extracellular space

• 3-sulfino-L-alanineReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. L-Cysteine:oxygen oxidoreductase

  Catalysed by PTGS2, MOCOS, CDO1cytosolOne of 2 routes

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

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 13 morecytosolOne of 7 routes

• (2E)-hexadecenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (EPA)
  2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  3. Carnitine O-Palmitoyltransferase

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

• (9Z)-hexadecenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (EPA)
  2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (palmitolate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 17 routes

• a cardiolipinReach from here →
  1. long-chain-fatty-acid-CoA ligase (EPA)
  2. acyl-CoA pool formation and breakdown
  3. 1'-[1,2-diacyl-sn-glycero-3-phospho],3'-[1-acyl-sn-glycero-3-phospho]-glycerol + an acyl-CoA = a cardiolipin + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 5 morecytosol

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

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

• an all-trans-retinyl esterReach from here →
  1. long-chain-fatty-acid-CoA ligase (EPA)
  2. acyl-CoA pool formation and breakdown
  3. all-trans-retinol + an acyl-CoA = an all-trans-retinyl ester + CoA

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 8 morecytosolOne of 5 routes

• CHEBI:63544Reach from here →
  1. long-chain-fatty-acid-CoA ligase (EPA)
  2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (adrenic acid)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 10 routes

• 18-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. cytochrome P450 (arachidonate)

  Catalysed by CYP4F8cytosol, extracellular space, endoplasmic reticulumOne of 2 routes

• a 1,2-diacyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. long-chain-fatty-acid-CoA ligase (EPA)
  2. acyl-CoA pool formation and breakdown
  3. a 1-acyl-sn-glycero-3-phosphoethanolamine + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phosphoethanolamine + CoA

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

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

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

• a 1,2-diacyl-sn-glycero-3-phospho-(1'-sn-glycerol)Reach from here →
  1. long-chain-fatty-acid-CoA ligase (EPA)
  2. acyl-CoA pool formation and breakdown
  3. 1-acyl-sn-glycero-3-phospho-(1'-sn-glycerol) + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phospho-(1'-sn-glycerol) + CoA

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

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

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

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

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 17 routes

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

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 14 routes

• a 2,3-saturated acyl-CoAReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. a 2,3-saturated acyl-CoA + A = a 2,3-dehydroacyl-CoA + AH2

  Catalysed by PTGS2, AIFM1, PYROXD1, ACAD10One of 2 routes

• an N-acylsphinganine-1-phosphocholineReach from here →
  1. (10Z)-heptadecenoic acid formation
  2. N-acylsphingosine amidohydrolase
  3. an N-acylsphinganine + a 1,2-diacyl-sn-glycero-3-phosphocholine = an N-acylsphinganine-1-phosphocholine + a 1,2-diacyl-sn-glycerol

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 3 morecytosol

• all-trans-retinyl 9Z-octadecenoateReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O
  2. all-trans-13,14-dihydroretinol + A = all-trans-retinol + AH2
  3. 1,2,3-tri-(9Z-octadecenoyl)-glycerol + all-trans-retinol = all-trans-retinyl 9Z-octadecenoate + di-(9Z)-octadecenoylglycerol

  Catalysed by PTGS2, RETSAT, PNPLA4, PNPLA2

• (2E)-octadecenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (EPA)
  2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  3. Carnitine O-Palmitoyltransferase

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

• 3-oxo-(8Z,11Z,14Z,17Z)-eicosatetraenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (EPA)
  2. Beta Oxidation of Fatty Acid
  3. (6Z,9Z,12Z,15Z)-octadecatetraenoyl-CoA + malonyl-CoA + H(+) = 3-oxo-(8Z,11Z,14Z,17Z)-eicosatetraenoyl-CoA + CO2 + CoA

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

• 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol)Reach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol) + H2O = sn-glycero-3-phospho-(1'-sn-glycerol) + (9Z)-octadecenoate + H(+)

  Catalysed by ABHD12cytosol, extracellular space

• 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1D-myo-inositol)Reach from here →
  1. (10Z)-heptadecenoic acid formation
  2. (10Z)-heptadecenoic acid formation
  3. 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1D-myo-inositol) + H2O = 1-hexadecanoyl-sn-glycero-3-phospho-(1D-myo-inositol) + (9Z)-octadecenoate + H(+)

  Catalysed by ABHD16Acytosol, extracellular space

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

  Catalysed by NAAA, ASAH1, ACER2, ASAH2cytosol, extracellular space

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

  Catalysed by ASAH1, ACER2, ASAH2cytosol, extracellular space

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

  Catalysed by ASAH1, ACER2, ASAH2cytosol, extracellular space

• (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

• (9Z,12Z,15Z,18Z,21Z)-3-oxotetracosapentaenoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (EPA)
  2. fatty-acyl-CoA elongation (N-C20:5CoA)
  3. (7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl-CoA + malonyl-CoA + H(+) = (9Z,12Z,15Z,18Z,21Z)-3-oxotetracosapentaenoyl-CoA + CO2 + CoA

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

• (9Z,12Z,15Z)-octadecatrienoyl-CoAReach from here →
  1. long-chain-fatty-acid-CoA ligase (EPA)
  2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA hydrolase
  3. long-chain-fatty-acid-CoA ligase (linolenate)

  Catalysed by SLC27A2, ACSL4, ACSL3, ACSL1 and 7 morecytosolOne of 10 routes