an N-acylsphing-4-enine

Three steps

• 13-hydroxytetradecanoateReach from here →
  1. N-Acylsphingosine amidohydrolase
  2. (10Z)-heptadecenoic acid formation
  3. myristic acid[r] + O2[r] + FMNH2[r] = FMN[r] + H2O[r] + 13-hydroxytetradecanoate[r]

  Catalysed by ASAH1, CYP2E1lysosome, extracellular space, endoplasmic reticulumOne of 3 routes

• (18S)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoateReach from here →
  1. N-Acylsphingosine amidohydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18S)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + A + H2O

  Catalysed by ASAH1, PTGS2lysosome, extracellular space

• (15S)-hydroxy-(5Z,8Z,11Z,13E,17Z)-eicosapentaenoateReach from here →
  1. N-Acylsphingosine amidohydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (15S)-hydroxy-(5Z,8Z,11Z,13E,17Z)-eicosapentaenoate + A + H2O

  Catalysed by ASAH1, PTGS2lysosome, extracellular space

• pregnenolone sulfateReach from here →
  1. a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + an N-acylsphing-4-enine
  2. 6 reduced [adrenodoxin] + cholesterol + 3 O2 + 6 H(+) = 4-methylpentanal + pregnenolone + 6 oxidized [adrenodoxin] + 4 H2O
  3. 3'-phosphoadenylyl-sulfate:pregnenolone sulfotransferase

  Catalysed by GBA1, GBA2, CYP11A1, SULT2B1cytosolOne of 4 routes

• prostaglandin G1Reach from here →
  1. N-Acylsphingosine amidohydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (8Z,11Z,14Z)-eicosatrienoate + 2 O2 = prostaglandin G1

  Catalysed by ASAH1, PTGS2lysosome, extracellular space

• prostaglandin G3Reach from here →
  1. N-Acylsphingosine amidohydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + 2 O2 = prostaglandin G3

  Catalysed by ASAH1, PTGS2lysosome, extracellular space

• 10-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. N-Acylsphingosine amidohydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = 10-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by ASAH1, CYP3A4, CYP2C9lysosome, extracellular space

• (17S)-hydroperoxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoateReach from here →
  1. N-Acylsphingosine amidohydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + O2 = (17S)-hydroperoxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoate

  Catalysed by ASAH1, ALOX5, ALOX15lysosome, extracellular space

• 14-hydroperoxy-(7Z,10Z,12E,16Z,19Z)-docosapentaenoateReach from here →
  1. N-Acylsphingosine amidohydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (7Z,10Z,13Z,16Z,19Z)-docosapentaenoate + O2 = 14-hydroperoxy-(7Z,10Z,12E,16Z,19Z)-docosapentaenoate

  Catalysed by ASAH1, ALOX15lysosome, extracellular space

• (8S,15S)-dihydroperoxy-(5Z,9E,11Z,13E)-eicosatetraenoateReach from here →
  1. N-Acylsphingosine amidohydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + 2 O2 = (8S,15S)-dihydroperoxy-(5Z,9E,11Z,13E)-eicosatetraenoate

  Catalysed by ASAH1, ALOX15lysosome, extracellular space

• (14R,15S)-dihydroperoxy-(5Z,8Z,10E,12E)-eicosatetraenoateReach from here →
  1. N-Acylsphingosine amidohydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + 2 O2 = (14R,15S)-dihydroperoxy-(5Z,8Z,10E,12E)-eicosatetraenoate

  Catalysed by ASAH1, ALOX15lysosome, extracellular space

• 19,20-epoxy-(4Z,7Z,10Z,13Z,16Z)-docosapentaenoateReach from here →
  1. N-Acylsphingosine amidohydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + reduced [NADPH--hemoprotein reductase] + O2 = 19,20-epoxy-(4Z,7Z,10Z,13Z,16Z)-docosapentaenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by ASAH1, CYP4F8, CYP4F12lysosome, extracellular space

• 16,17-epoxy-(4Z,7Z,10Z,13Z,19Z)-docosapentaenoateReach from here →
  1. N-Acylsphingosine amidohydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + reduced [NADPH--hemoprotein reductase] + O2 = 16,17-epoxy-(4Z,7Z,10Z,13Z,19Z)-docosapentaenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by ASAH1, CYP4F8, CYP4F12lysosome, extracellular space

• 13,14-epoxy-(4Z,7Z,10Z,16Z,19Z)-docosapentaenoateReach from here →
  1. N-Acylsphingosine amidohydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + reduced [NADPH--hemoprotein reductase] + O2 = 13,14-epoxy-(4Z,7Z,10Z,16Z,19Z)-docosapentaenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by ASAH1, CYP4F8, CYP4F12lysosome, extracellular space

• 10,11-epoxy-(4Z,7Z,13Z,16Z,19Z)-docosapentaenoateReach from here →
  1. N-Acylsphingosine amidohydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + reduced [NADPH--hemoprotein reductase] + O2 = 10,11-epoxy-(4Z,7Z,13Z,16Z,19Z)-docosapentaenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by ASAH1, CYP4F8, CYP4F12lysosome, extracellular space

• 19,20-epoxy-(7Z,10Z,13Z,16Z)-docosatetraenoateReach from here →
  1. N-Acylsphingosine amidohydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (7Z,10Z,13Z,16Z,19Z)-docosapentaenoate + reduced [NADPH--hemoprotein reductase] + O2 = 19,20-epoxy-(7Z,10Z,13Z,16Z)-docosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by ASAH1, CYP4F8, CYP4F12lysosome, extracellular space

• 16,17-epoxy-(7Z,10Z,13Z,19Z)-docosatetraenoateReach from here →
  1. N-Acylsphingosine amidohydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (7Z,10Z,13Z,16Z,19Z)-docosapentaenoate + reduced [NADPH--hemoprotein reductase] + O2 = 16,17-epoxy-(7Z,10Z,13Z,19Z)-docosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by ASAH1, CYP4F8, CYP4F12lysosome, extracellular space

• 13,14-epoxy-(7Z,10Z,16Z,19Z)-docosatetraenoateReach from here →
  1. N-Acylsphingosine amidohydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (7Z,10Z,13Z,16Z,19Z)-docosapentaenoate + reduced [NADPH--hemoprotein reductase] + O2 = 13,14-epoxy-(7Z,10Z,16Z,19Z)-docosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by ASAH1, CYP4F8, CYP4F12lysosome, extracellular space

• 10,11-epoxy-(7Z,13Z,16Z,19Z)-docosatetraenoateReach from here →
  1. N-Acylsphingosine amidohydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (7Z,10Z,13Z,16Z,19Z)-docosapentaenoate + reduced [NADPH--hemoprotein reductase] + O2 = 10,11-epoxy-(7Z,13Z,16Z,19Z)-docosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by ASAH1, CYP4F8, CYP4F12lysosome, extracellular space

• 2,4-dinitrophenyl-S-glutathioneReach from here →
  1. N-Acylsphingosine amidohydrolase
  2. (10Z)-heptadecenoic acid formation
  3. transport of arachidonate (cytosol to extracellular)

  Catalysed by ASAH1, SLCO1B1lysosome, extracellular space, cytosolOne of 2 routes

• N-(9Z-octadecenoyl)-L-phenylalanineReach from here →
  1. N-Acylsphingosine amidohydrolase
  2. (10Z)-heptadecenoic acid formation
  3. L-phenylalanine + (9Z)-octadecenoate = N-(9Z-octadecenoyl)-L-phenylalanine + H2O

  Catalysed by ASAH1, PM20D1lysosome, extracellular space

• N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanineReach from here →
  1. N-Acylsphingosine amidohydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + L-phenylalanine = N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-L-phenylalanine + H2O

  Catalysed by ASAH1, PM20D1lysosome, extracellular space

• N-(9Z-octadecenoyl)-L-leucineReach from here →
  1. N-Acylsphingosine amidohydrolase
  2. (10Z)-heptadecenoic acid formation
  3. N-(9Z-octadecenoyl)-L-leucine + H2O = L-leucine + (9Z)-octadecenoate

  Catalysed by ASAH1, PM20D1lysosome, extracellular space

• N-octadecanoylglycineReach from here →
  1. acyl-CoA:sphingosine N-acyltransferase
  2. acyl-CoA pool formation and breakdown
  3. octadecanoyl-CoA + glycine = N-octadecanoylglycine + CoA + H(+)

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 1 moreGolgi apparatus, cytosol

• N-(9Z-hexadecenoyl)-glycineReach from here →
  1. acyl-CoA:sphingosine N-acyltransferase
  2. acyl-CoA pool formation and breakdown
  3. (9Z)-hexadecenoyl-CoA + glycine = N-(9Z-hexadecenoyl)-glycine + CoA + H(+)

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 1 moreGolgi apparatus, cytosol

• (19R,20S)-epoxy-(4Z,7Z,10Z,13Z,16Z)-docosapentaenoateReach from here →
  1. N-Acylsphingosine amidohydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + reduced [NADPH--hemoprotein reductase] + O2 = (19R,20S)-epoxy-(4Z,7Z,10Z,13Z,16Z)-docosapentaenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by ASAH1, CYP1A1, CYP1A2, CYP3A4 and 4 morelysosome, extracellular space

• (19S,20R)-epoxy-(4Z,7Z,10Z,13Z,16Z)-docosapentaenoateReach from here →
  1. N-Acylsphingosine amidohydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + reduced [NADPH--hemoprotein reductase] + O2 = (19S,20R)-epoxy-(4Z,7Z,10Z,13Z,16Z)-docosapentaenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by ASAH1, CYP1A1, CYP3A4, CYP2C8 and 3 morelysosome, extracellular space

• 8,9-epoxy-(5Z,11Z,14Z,17Z)-eicosatetraenoateReach from here →
  1. N-Acylsphingosine amidohydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + reduced [NADPH--hemoprotein reductase] + O2 = 8,9-epoxy-(5Z,11Z,14Z,17Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by ASAH1, CYP2C9lysosome, extracellular space

• 11,12-epoxy-(5Z,8Z,14Z,17Z)-eicosatetraenoateReach from here →
  1. N-Acylsphingosine amidohydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + reduced [NADPH--hemoprotein reductase] + O2 = 11,12-epoxy-(5Z,8Z,14Z,17Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by ASAH1, CYP2C8, CYP2C9lysosome, extracellular space

• 14,15-epoxy-(5Z,8Z,11Z,17Z)-eicosatetraenoateReach from here →
  1. N-Acylsphingosine amidohydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + reduced [NADPH--hemoprotein reductase] + O2 = 14,15-epoxy-(5Z,8Z,11Z,17Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by ASAH1, CYP2C8, CYP2C9lysosome, extracellular space

• 7-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. N-Acylsphingosine amidohydrolase
  2. (10Z)-heptadecenoic acid formation
  3. unspecific monooxygenase (arachidonate)

  Catalysed by ASAH1, CYP1A1, CYP1A2, CYP2E1 and 23 morelysosome, extracellular space, cytosolOne of 2 routes

• 13-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. N-Acylsphingosine amidohydrolase
  2. (10Z)-heptadecenoic acid formation
  3. unspecific monooxygenase (arachidonate)

  Catalysed by ASAH1, CYP1A1, CYP1A2, CYP2E1 and 23 morelysosome, extracellular space, cytosolOne of 2 routes

• (24S)-hydroxycholesterol 24-sulfateReach from here →
  1. a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + an N-acylsphing-4-enine
  2. cholesterol + reduced [NADPH--hemoprotein reductase] + O2 = (24S)-hydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
  3. (24S)-hydroxycholesterol + 3'-phosphoadenylyl sulfate = (24S)-hydroxycholesterol 24-sulfate + adenosine 3',5'-bisphosphate + H(+)

  Catalysed by GBA1, GBA2, CYP46A1, SULT2A1

• (24S)-hydroxycholesterol 3-sulfateReach from here →
  1. a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + an N-acylsphing-4-enine
  2. cholesterol + reduced [NADPH--hemoprotein reductase] + O2 = (24S)-hydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
  3. (24S)-hydroxycholesterol + 3'-phosphoadenylyl sulfate = (24S)-hydroxycholesterol 3-sulfate + adenosine 3',5'-bisphosphate + H(+)

  Catalysed by GBA1, GBA2, CYP46A1, SULT2B1 and 2 more

• 13(S)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. N-Acylsphingosine amidohydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = 13(S)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by ASAH1, CYP2C9lysosome, extracellular space

• 16(R)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. N-Acylsphingosine amidohydrolase
  2. (10Z)-heptadecenoic acid formation
  3. unspecific monooxygenase (arachidonate)

  Catalysed by ASAH1, CYP1A1, CYP1A2, CYP2E1 and 23 morelysosome, extracellular space, cytosol

• 1-hexadecanoyl-2-heptanoyl-sn-glycero-3-phosphocholineReach from here →
  1. ceramide:phosphatidylcholine cholinephosphotransferase
  2. 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine + an N-acylsphing-4-enine = 1,2-dihexadecanoyl-sn-glycerol + a sphingomyelin
  3. 1,2-diheptanoyl-sn-glycero-3-phosphocholine + 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine = 1-hexadecanoyl-2-heptanoyl-sn-glycero-3-phosphocholine + 1-heptanoyl-2-hexadecanoyl-sn-glycero-3-phosphocholine

  Catalysed by SGMS1, SGMS2, PLAAT2Golgi apparatus

• 1-heptanoyl-2-hexadecanoyl-sn-glycero-3-phosphocholineReach from here →
  1. ceramide:phosphatidylcholine cholinephosphotransferase
  2. 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine + an N-acylsphing-4-enine = 1,2-dihexadecanoyl-sn-glycerol + a sphingomyelin
  3. 1,2-diheptanoyl-sn-glycero-3-phosphocholine + 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine = 1-hexadecanoyl-2-heptanoyl-sn-glycero-3-phosphocholine + 1-heptanoyl-2-hexadecanoyl-sn-glycero-3-phosphocholine

  Catalysed by SGMS1, SGMS2, PLAAT2Golgi apparatus

• 2-hydroxyeicosanoyl-CoAReach from here →
  1. acyl-CoA:sphingosine N-acyltransferase
  2. acyl-CoA pool formation and breakdown
  3. eicosanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxyeicosanoyl-CoA + succinate + CO2

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 1 moreGolgi apparatus, cytosol

• 2-hydroxydodecanoyl-CoAReach from here →
  1. acyl-CoA:sphingosine N-acyltransferase
  2. acyl-CoA pool formation and breakdown
  3. dodecanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxydodecanoyl-CoA + succinate + CO2

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 1 moreGolgi apparatus, cytosol

• 2-hydroxytetradecanoyl-CoAReach from here →
  1. acyl-CoA:sphingosine N-acyltransferase
  2. acyl-CoA pool formation and breakdown
  3. tetradecanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxytetradecanoyl-CoA + succinate + CO2

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 1 moreGolgi apparatus, cytosol

• 1-O-(1Z-octadecenoyl)-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-N-hexadecanoyl-ethanolamineReach from here →
  1. ceramide:phosphatidylcholine cholinephosphotransferase
  2. 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine + an N-acylsphing-4-enine = 1,2-dihexadecanoyl-sn-glycerol + a sphingomyelin
  3. 1-(1Z-octadecenyl)-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine = 1-O-(1Z-octadecenoyl)-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-N-hexadecanoyl-ethanolamine + 2-hexadecanoyl-sn-glycero-3-phosphocholine + H(+)

  Catalysed by SGMS1, SGMS2, PLA2G4EGolgi apparatus

• 11-cis-retinyl tetradecanoateReach from here →
  1. acyl-CoA:sphingosine N-acyltransferase
  2. acyl-CoA pool formation and breakdown
  3. 11-cis-retinol + tetradecanoyl-CoA = 11-cis-retinyl tetradecanoate + CoA

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 1 moreGolgi apparatus, cytosol

• 9-cis-retinyl tetradecanoateReach from here →
  1. acyl-CoA:sphingosine N-acyltransferase
  2. acyl-CoA pool formation and breakdown
  3. 9-cis-retinol + tetradecanoyl-CoA = 9-cis-retinyl tetradecanoate + CoA

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 1 moreGolgi apparatus, cytosol

• 13-cis-retinyl tetradecanoateReach from here →
  1. acyl-CoA:sphingosine N-acyltransferase
  2. acyl-CoA pool formation and breakdown
  3. 13-cis-retinol + tetradecanoyl-CoA = 13-cis-retinyl tetradecanoate + CoA

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 1 moreGolgi apparatus, cytosol

• all-trans-retinyl tetradecanoateReach from here →
  1. acyl-CoA:sphingosine N-acyltransferase
  2. acyl-CoA pool formation and breakdown
  3. all-trans-retinol + tetradecanoyl-CoA = all-trans-retinyl tetradecanoate + CoA

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 1 moreGolgi apparatus, cytosol

• tetradecyl tetradecanoateReach from here →
  1. acyl-CoA:sphingosine N-acyltransferase
  2. acyl-CoA pool formation and breakdown
  3. tetradecan-1-ol + tetradecanoyl-CoA = tetradecyl tetradecanoate + CoA

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 1 moreGolgi apparatus, cytosol

• 1-(9Z-octadecenoyl)-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphateReach from here →
  1. acyl-CoA:sphingosine N-acyltransferase
  2. acyl-CoA pool formation and breakdown
  3. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA + 1-(9Z-octadecenoyl)-sn-glycero-3-phosphate = 1-(9Z-octadecenoyl)-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphate + CoA

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 1 moreGolgi apparatus, cytosol

• beta-D-glucosyl-N-(9Z-octadecenoyl)-sphing-4E-enineReach from here →
  1. acyl-CoA:sphingosine N-acyltransferase
  2. N-(9Z-octadecenoyl)-sphing-4-enine + H2O = sphing-4-enine + (9Z)-octadecenoate
  3. beta-D-glucosyl-N-(9Z-octadecenoyl)-sphing-4E-enine + cholesterol = N-(9Z-octadecenoyl)-sphing-4-enine + cholesteryl 3-beta-D-glucoside

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 3 moreGolgi apparatusOne of 2 routes

• a 3-hydroxyacyl derivative of bacterial toxinReach from here →
  1. an N-acylsphing-4-enine + H2O = sphing-4-enine + a fatty acid
  2. a 3-(acyloxy)acyl derivative of bacterial toxin + H2O = a 3-hydroxyacyl derivative of bacterial toxin + a fatty acid + H(+)
  3. a 3-(acyloxy)acyl derivative of bacterial toxin + H2O = a 3-hydroxyacyl derivative of bacterial toxin + a fatty acid + H(+)

  Catalysed by NAAA, ASAH1, ACER2, ACER1 and 3 more