a sphingomyelin

Three steps

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoserineReach from here →
  1. SM pool hydrolysis
  2. (10Z)-heptadecenoic acid formation
  3. 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoserine + H2O = 1-heptadecanoyl-sn-glycero-3-phosphoserine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)

  Catalysed by ABHD16Acytosol, extracellular space

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. SM pool hydrolysis
  2. (10Z)-heptadecenoic acid formation
  3. 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + H2O = 1-heptadecanoyl-sn-glycero-3-phosphocholine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)

  Catalysed by ABHD16Acytosol, extracellular space

• 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. SM pool hydrolysis
  2. (10Z)-heptadecenoic acid formation
  3. 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine + H2O = 1-heptadecanoyl-sn-glycero-3-phosphoethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)

  Catalysed by ABHD16Acytosol, extracellular space

• (5Z)-tetradecenoyl-CoAReach from here →
  1. ceramide cholinephosphotransferase (CDP-choline)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. acyl-CoA pool formation and breakdown

  Catalysed by ASAH1, ACER2, ACER1, ASAH2endoplasmic reticulum, Golgi apparatus, cytosol

• 7-hydroxydodecanoateReach from here →
  1. SM pool hydrolysis
  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

• (5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-cholesterolReach from here →
  1. ceramide cholinephosphotransferase (CDP-choline)
  2. a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + an N-acylsphing-4-enine
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA + cholesterol = (5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-cholesterol + CoA

  Catalysed by GBA1, GBA2, SOAT2endoplasmic reticulumOne of 2 routes

• N,1-diacyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. an N-acylsphing-4-enine + a 1,2-diacyl-sn-glycero-3-phosphocholine = a sphingomyelin + a 1,2-diacyl-sn-glycerol
  2. a 1,2-diacyl-sn-glycero-3-phosphoethanolamine + a 1,2-diacyl-sn-glycero-3-phosphocholine = an N-acyl-1,2-diacyl-sn-glycero-3-phosphoethanolamine + a 2-acyl-sn-glycero-3-phosphocholine + H(+)
  3. an N-acyl-1,2-diacyl-sn-glycero-3-phosphoethanolamine + H2O = N,1-diacyl-sn-glycero-3-phosphoethanolamine + a fatty acid + H(+)

  Catalysed by SGMS1, SGMS2, PLA2G4E, PLAAT5 and 2 more

• N-hexadecanoyl-1-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine + an N-acylsphing-4-enine = 1,2-dihexadecanoyl-sn-glycerol + a sphingomyelin
  2. 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine = hexadecanoyl-sn-glycero-3-phosphocholine + N-hexadecanoyl-1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + H(+)
  3. N-hexadecanoyl-1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + H2O = N-hexadecanoyl-1-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine + (9Z)-octadecenoate + H(+)

  Catalysed by SGMS2, PLAAT3, PLAAT1, PLA2G1B and 3 more

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

  Catalysed by ASAH1cytosol, extracellular space

• 4beta-hydroxycholesterolReach from here →
  1. ceramide cholinephosphotransferase (CDP-choline)
  2. a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + an N-acylsphing-4-enine
  3. cholesterol + reduced [NADPH--hemoprotein reductase] + O2 = 4beta-hydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by GBA1, GBA2, CYP3A4endoplasmic reticulum

• an N(2)-acyl-L-glutamineReach from here →
  1. ceramide cholinephosphotransferase (CDP-choline)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. an acyl-CoA + L-glutamine = an N(2)-acyl-L-glutamine + CoA + H(+)

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 2 moreendoplasmic reticulum, Golgi apparatus

• (7Z)-hexadecenoyl-CoAReach from here →
  1. ceramide cholinephosphotransferase (CDP-choline)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. acyl-CoA pool formation and breakdown

  Catalysed by ASAH1, ACER2, ACER1, ASAH2endoplasmic reticulum, Golgi apparatus, cytosol

• cholesteryl (5Z,8Z,11Z)-eicosatrienoateReach from here →
  1. ceramide cholinephosphotransferase (CDP-choline)
  2. a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + an N-acylsphing-4-enine
  3. 1-hexadecanoyl-2-(5Z,8Z,11Z-eicosatrienoyl)-sn-glycero-3-phosphocholine + cholesterol = cholesteryl (5Z,8Z,11Z)-eicosatrienoate + 1-hexadecanoyl-sn-glycero-3-phosphocholine

  Catalysed by GBA1, GBA2, LCATendoplasmic reticulum

• (6Z,9Z,12Z-octadecatrienoyl)-cholesterolReach from here →
  1. ceramide cholinephosphotransferase (CDP-choline)
  2. a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + an N-acylsphing-4-enine
  3. 1-hexadecanoyl-2-(6Z,9Z,12Z-octadecatrienoyl)-sn-glycero-3-phosphocholine + cholesterol = (6Z,9Z,12Z-octadecatrienoyl)-cholesterol + 1-hexadecanoyl-sn-glycero-3-phosphocholine

  Catalysed by GBA1, GBA2, LCATendoplasmic reticulum

• cholesteryl (11Z)-octadecenoateReach from here →
  1. ceramide cholinephosphotransferase (CDP-choline)
  2. a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + an N-acylsphing-4-enine
  3. (11Z)-octadecenoyl-CoA + cholesterol = cholesteryl (11Z)-octadecenoate + CoA

  Catalysed by GBA1, GBA2, SOAT1endoplasmic reticulum

• tricosanoyl-CoAReach from here →
  1. ceramide cholinephosphotransferase (CDP-choline)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. acyl-CoA pool formation and breakdown

  Catalysed by ASAH1, ACER2, ACER1, ASAH2endoplasmic reticulum, Golgi apparatus, cytosolOne of 3 routes

• a 3-oxoacyl-CoAReach from here →
  1. ceramide cholinephosphotransferase (CDP-choline)
  2. acyl-CoA:sphingosine N-acyltransferase
  3. an acyl-CoA + acetyl-CoA = a 3-oxoacyl-CoA + CoA

  Catalysed by ASAH1, ACER2, ACER1, ASAH2 and 4 moreendoplasmic reticulum, Golgi apparatus

• (12S)-hydroperoxy-(5Z,8Z,10E,14Z,17Z)-eicosapentaenoateReach from here →
  1. SM pool hydrolysis
  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

• (18R)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. SM pool hydrolysis
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH--hemoprotein reductase] + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CYP4F8cytosol, extracellular space

• 17R-hydroxy-(4Z,7Z,10Z,13Z,15E,19Z)-docosahexaenoateReach from here →
  1. SM pool hydrolysis
  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 space

• 13-hydroxy-(4Z,7Z,10Z,14E,16Z,19Z)-docosahexaenoateReach from here →
  1. SM pool hydrolysis
  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 space

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

  Catalysed by PTGS1, PTGS2cytosol, extracellular spaceOne of 2 routes

• (15R)-hydroxy-(5Z,8Z,11Z,13E,17Z)-eicosapentaenoateReach from here →
  1. SM pool hydrolysis
  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 space

• (11R)-hydroxy-(5Z,8Z,12E,14Z,17Z)-eicosapentaenoateReach from here →
  1. SM pool hydrolysis
  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 space

• 15-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. SM pool hydrolysis
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = 15-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate

  Catalysed by ALOX15Bcytosol, extracellular space

• 5-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. SM pool hydrolysis
  2. (10Z)-heptadecenoic acid formation
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = 5-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate

  Catalysed by ALOX15Bcytosol, extracellular space

• 13R-hydroxy-(7Z,10Z,14E,16Z,19Z)-docosapentaenoateReach from here →
  1. SM pool hydrolysis
  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 space