cholesterol

Three steps

• 2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholineReach from here →
  1. 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
  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 + N-(acetyl)-sphing-4-enine = 1-hexadecanoyl-N-(acetyl)-sphing-4-enine + 2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine

  Catalysed by LCAT, LPCAT3, MBOAT7, PLA2G15One of 2 routes

• 1-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-N-(acetyl)-sphing-4-enineReach from here →
  1. 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
  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 + N-(acetyl)-sphing-4-enine = 1-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-N-(acetyl)-sphing-4-enine + 1-hexadecanoyl-sn-glycero-3-phosphocholine

  Catalysed by LCAT, LPCAT3, MBOAT7, PLA2G15

• (9Z-octadecenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. 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
  2. 1-hexadecanoyl-sn-glycero-3-phosphocholine + H2O = 1-hexadecanoyl-sn-glycerol + phosphocholine + H(+)
  3. 1-hexadecanoyl-sn-glycerol + 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine = 1-hexadecanoyl-3-(9Z)-octadecenoyl-sn-glycerol + (9Z-octadecenoyl)-sn-glycero-3-phosphocholine

  Catalysed by LCAT, SMPD2, ENPP6, ENPP7 and 2 more

• 2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. 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
  2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 1-hexadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholine + CoA
  3. 1-hexadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholine + 1-hexadecanoyl-N-(acetyl)-sphing-4-enine

  Catalysed by LCAT, LPCAT1, PLA2G15One of 2 routes

• 1-(9Z,12Z-octadecadienoyl)-N-acetylsphing-4-enineReach from here →
  1. 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
  2. (9Z,12Z)-octadecadienoyl-CoA + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine + CoA
  3. 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-(9Z,12Z-octadecadienoyl)-N-acetylsphing-4-enine + 1-hexadecanoyl-sn-glycero-3-phosphocholine

  Catalysed by LCAT, LPCAT3, MBOAT2, LPCAT1 and 1 more

• 1-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-N-(acetyl)-sphing-4-enineReach from here →
  1. 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
  2. (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 1-hexadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholine + CoA
  3. 1-hexadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-N-(acetyl)-sphing-4-enine + 1-hexadecanoyl-sn-glycero-3-phosphocholine

  Catalysed by LCAT, LPCAT1, PLA2G15

• 1-O-alkyl-3-acylglycerolReach 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. acyl-CoA:sphingosine N-acyltransferase
  3. 1-O-alkylglycerol + an acyl-CoA = 1-O-alkyl-3-acylglycerol + CoA

  Catalysed by GBA1, GBA2, ASAH1, ACER2 and 4 moreGolgi apparatusOne of 3 routes

• (4Z,7Z,10Z,13Z,16Z)-docosapentaenoyl-CoAReach 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. acyl-CoA:sphingosine N-acyltransferase
  3. acyl-CoA pool formation and breakdown

  Catalysed by GBA1, GBA2, ASAH1, ACER2 and 2 moreGolgi apparatus, cytosol

• (11Z,14Z)-eicosadienoyl-CoAReach 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. acyl-CoA:sphingosine N-acyltransferase
  3. acyl-CoA pool formation and breakdown

  Catalysed by GBA1, GBA2, ASAH1, ACER2 and 2 moreGolgi apparatus, cytosol

• (13Z)-eicosenoyl-CoAReach 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. acyl-CoA:sphingosine N-acyltransferase
  3. acyl-CoA pool formation and breakdown

  Catalysed by GBA1, GBA2, ASAH1, ACER2 and 2 moreGolgi apparatus, cytosol

• 1-O-alkyl-2,3-diacyl-sn-glycerolReach from here →
  1. a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol 4-phosphate)(out) + cholesterol(in) = a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol 4-phosphate)(in) + cholesterol(out)
  2. a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol 4-phosphate)(out) + a 1,2-diacyl-sn-glycero-3-phosphocholine(in) = a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol 4-phosphate)(in) + a 1,2-diacyl-sn-glycero-3-phosphocholine(out)
  3. 1-O-alkyl-2-acyl-sn-glycerol + a 1,2-diacyl-sn-glycero-3-phosphocholine = 1-O-alkyl-2,3-diacyl-sn-glycerol + a 2-acyl-sn-glycero-3-phosphocholine

  Catalysed by OSBP, OSBPL3, PLA2G15inner side of the membrane, outer side of the membraneOne of 2 routes

• 20-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + cholesterol = cholesteryl (5Z,8Z,11Z,14Z)-eicosatetraenoate + CoA
  2. sterol esterase (Cholesteryl Arachidonate)
  3. arachidonic acid:oxygen 1-oxidoreductase

  Catalysed by SOAT2, SOAT1, CEL, LIPA and 27 morelysosome, cytosolOne of 3 routes

• 11,12-epoxy-(5Z,8Z,14Z)-eicosatrienoateReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + cholesterol = cholesteryl (5Z,8Z,11Z,14Z)-eicosatetraenoate + CoA
  2. sterol esterase (Cholesteryl Arachidonate)
  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 SOAT2, SOAT1, CEL, LIPA and 1 morelysosome

• 19-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + cholesterol = cholesteryl (5Z,8Z,11Z,14Z)-eicosatetraenoate + CoA
  2. sterol esterase (Cholesteryl Arachidonate)
  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 SOAT2, SOAT1, CEL, LIPA and 5 morelysosome

• 11-hydroxydodecanoateReach from here →
  1. 1-(beta-D-galactosyl)-N-dodecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-galactoside + N-dodecanoylsphing-4-enine
  2. H2O[c] + N-dodecanoylsphing-4-enine[c] = lauric acid[c] + sphingosine[c]
  3. lauric acid[r] + O2[r] + FMNH2[r] = FMN[r] + H2O[r] + 11-hydroxydodecanoate[r]

  Catalysed by GBA1, GBA2, NAAA, CYP2E1cytosol, endoplasmic reticulumOne of 3 routes

• (17R,18S)-epoxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA + cholesterol = (5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-cholesterol + CoA
  2. Steryl-ester acylhydrolase
  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 SOAT2, CEL, LIPA, CYP1A1 and 6 morelysosome

• (17S,18R)-epoxy-(5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA + cholesterol = (5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-cholesterol + CoA
  2. Steryl-ester acylhydrolase
  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 SOAT2, CEL, LIPA, CYP2C8 and 2 morelysosome

• 19-hydroxy-(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoateReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA + cholesterol = (5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-cholesterol + CoA
  2. Steryl-ester acylhydrolase
  3. EPA[r] + O2[r] + FMNH2[r] = FMN[r] + H2O[r] + 19-hydroxy-(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate[r]

  Catalysed by SOAT2, CEL, LIPA, CYP2E1lysosome, endoplasmic reticulumOne of 3 routes

• 20-hydroxy-(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoateReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA + cholesterol = (5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-cholesterol + CoA
  2. Steryl-ester acylhydrolase
  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 SOAT2, CEL, LIPA, CYP4F2 and 2 morelysosome

• 1-octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycerolReach from here →
  1. octadecanoyl-CoA + cholesterol = cholesteryl octadecanoate + CoA
  2. Steryl-ester acylhydrolase
  3. 1-octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycerol + H2O = 2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-glycerol + octadecanoate + H(+)

  Catalysed by SOAT1, CEL, LIPA, ABHD11lysosome

• (11Z,14Z)-eicosadienoateReach 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. N-Acylsphingosine amidohydrolase
  3. (10Z)-heptadecenoic acid formation

  Catalysed by GBA1, GBA2, ASAH1lysosome, extracellular spaceOne of 12 routes

• (17Z)-hexacosenoateReach 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. N-Acylsphingosine amidohydrolase
  3. (10Z)-heptadecenoic acid formation

  Catalysed by GBA1, GBA2, ASAH1lysosome, extracellular spaceOne of 12 routes

• (7Z,10Z,13Z,16Z,19Z)-docosapentaenoateReach 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. N-Acylsphingosine amidohydrolase
  3. (10Z)-heptadecenoic acid formation

  Catalysed by GBA1, GBA2, ASAH1lysosome, extracellular spaceOne of 12 routes

• (7Z,10Z,13Z,16Z)-docosatetraenoateReach 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. N-Acylsphingosine amidohydrolase
  3. (10Z)-heptadecenoic acid formation

  Catalysed by GBA1, GBA2, ASAH1lysosome, extracellular spaceOne of 12 routes

• a 1,3-diacyl-sn-glycerolReach from here →
  1. an acyl-CoA + cholesterol = a cholesterol ester + CoA
  2. a cholesterol ester + H2O = cholesterol + a fatty acid + H(+)
  3. a 1,3-diacyl-sn-glycerol + H2O = a 1-acyl-sn-glycerol + a fatty acid + H(+)

  Catalysed by SOAT2, SOAT1, CES1, LIPN and 3 moreOne of 3 routes

• a 1-O-(1Z-alkenyl)-2-acyl-sn-glycero-3-phosphocholineReach 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. acyl-CoA:sphingosine N-acyltransferase
  3. a 1-O-(1Z-alkenyl)-sn-glycero-3-phosphocholine + an acyl-CoA = a 1-O-(1Z-alkenyl)-2-acyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by GBA1, GBA2, ASAH1, ACER2 and 4 moreGolgi apparatus

• a 1-O-(1Z-alkenyl)-sn-glycero-3-phosphocholineReach from here →
  1. 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
  2. 1-hexadecanoyl-sn-glycero-3-phosphocholine + H2O = sn-glycerol 3-phosphocholine + hexadecanoate + H(+)
  3. a 1-O-(1Z-alkenyl)-sn-glycero-3-phosphocholine + H2O = a 2,3-saturated aldehyde + sn-glycerol 3-phosphocholine

  Catalysed by LCAT, PLA2G6, LYPLA1, LYPLA2 and 16 more

• a 1-O-(1Z-alkenyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. 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
  2. 1-hexadecanoyl-sn-glycero-3-phosphoethanolamine + 1-hexadecanoyl-sn-glycero-3-phosphocholine = sn-glycero-3-phosphoethanolamine + 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine
  3. a 1-O-(1Z-alkenyl)-sn-glycero-3-phosphoethanolamine + H2O = a 2,3-saturated aldehyde + sn-glycero-3-phosphoethanolamine

  Catalysed by LCAT, PLA2G4C, TMEM86A, TMEM86B

• a 1-O-(1Z-alkenyl)-2-acyl-sn-glycero-3-phosphoethanolamineReach 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. acyl-CoA:sphingosine N-acyltransferase
  3. a 1-O-(1Z-alkenyl)-sn-glycero-3-phosphoethanolamine + an acyl-CoA = a 1-O-(1Z-alkenyl)-2-acyl-sn-glycero-3-phosphoethanolamine + CoA

  Catalysed by GBA1, GBA2, ASAH1, ACER2 and 3 moreGolgi apparatus

• 1-O-(1Z)-alkenyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. 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
  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 + a 1-O-(1Z-alkenyl)-sn-glycero-3-phosphoethanolamine = 1-O-(1Z)-alkenyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphoethanolamine + 1-hexadecanoyl-sn-glycero-3-phosphocholine

  Catalysed by LCAT, LPCAT3, MBOAT7, PLA2G4C

• a 1-hexadecanoyl-2-acyl-sn-glycero-3-phosphocholineReach from here →
  1. 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
  2. 1-hexadecanoyl-sn-glycero-3-phosphocholine + hexadecanoyl-CoA = 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine + CoA
  3. 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine + a 2-acyl-sn-glycero-3-phosphocholine = a 1-hexadecanoyl-2-acyl-sn-glycero-3-phosphocholine + 2-hexadecanoyl-sn-glycero-3-phosphocholine

  Catalysed by LCAT, PRDX6, LPCAT3, LPCAT1 and 1 more

• a fatty acyl-CoAReach from here →
  1. an acyl-CoA + cholesterol = a cholesterol ester + CoA
  2. a cholesterol ester + H2O = cholesterol + a fatty acid + H(+)
  3. a fatty acid + ATP + CoA = a fatty acyl-CoA + AMP + diphosphate

  Catalysed by SOAT2, SOAT1, CES1, LIPN and 3 more

• (9S)-hydroxy-(10E,12Z)-octadecadienoateReach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. (9Z,12Z)-octadecadienoate + AH2 + O2 = (9S)-hydroxy-(10E,12Z)-octadecadienoate + A + H2O

  Catalysed by CH25H, AIFM1, PYROXD1, PTGS1 and 1 more

• (9R)-hydroxy-(10E,12Z)-octadecadienoateReach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. (9Z,12Z)-octadecadienoate + AH2 + O2 = (9R)-hydroxy-(10E,12Z)-octadecadienoate + A + H2O

  Catalysed by CH25H, AIFM1, PYROXD1, PTGS1 and 1 more

• N-dodecanoyl-(4R)-hydroxysphinganineReach from here →
  1. 1-(beta-D-galactosyl)-N-dodecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-galactoside + N-dodecanoylsphing-4-enine
  2. H2O[c] + N-dodecanoylsphing-4-enine[c] = lauric acid[c] + sphingosine[c]
  3. N-dodecanoyl-(4R)-hydroxysphinganine + H2O = (4R)-hydroxysphinganine + dodecanoate

  Catalysed by GBA1, GBA2, NAAA, ASAH1cytosol

• (5Z,8Z,11Z)-eicosatrienoateReach 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. N-Acylsphingosine amidohydrolase
  3. (10Z)-heptadecenoic acid formation

  Catalysed by GBA1, GBA2, ASAH1lysosome, extracellular spaceOne of 12 routes

• (5Z,7Z,8Z,10E,14Z,17Z)-12-hydroperoxyeicosapentaenoateReach from here →
  1. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA + cholesterol = (5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-cholesterol + CoA
  2. Steryl-ester acylhydrolase
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + O2 = (5Z,7Z,8Z,10E,14Z,17Z)-12-hydroperoxyeicosapentaenoate

  Catalysed by SOAT2, CEL, LIPA, ALOX12Blysosome

• N-hexadecanoyl-1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. 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
  2. 1-hexadecanoyl-sn-glycero-3-phosphocholine + hexadecanoyl-CoA = 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine + CoA
  3. 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(+)

  Catalysed by LCAT, PRDX6, LPCAT3, LPCAT1 and 2 moreOne of 4 routes

• 9-cis-retinolReach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. all-trans-13,14-dihydroretinol + A = all-trans-retinol + AH2
  3. retinol binding protein (retinol)

  Catalysed by CH25H, RETSAT, RBP1, RBP2cytosolOne of 2 routes

• a 1-(9Z-octadecenoyl)-2-acyl-sn-glycero-3-phosphocholineReach 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. ceramide:phosphatidylcholine cholinephosphotransferase
  3. 1-(9Z-octadecenoyl)-2-acyl-sn-3-glycerol + a sphingomyelin = a 1-(9Z-octadecenoyl)-2-acyl-sn-glycero-3-phosphocholine + an N-acylsphing-4-enine

  Catalysed by GBA1, GBA2, SGMS1, SGMS2Golgi apparatusOne of 2 routes

• 18-hydroxy-(9Z)-octadecenoateReach from here →
  1. cholesterol + (9Z)-octadecenoyl-CoA = cholesteryl (9Z-octadecenoate) + CoA
  2. Steryl-ester acylhydrolase
  3. (9Z)-octadecenoate + reduced [NADPH--hemoprotein reductase] + O2 = 18-hydroxy-(9Z)-octadecenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by SOAT2, SOAT1, CEL, LIPA and 2 morelysosome

• a ganglioside GM4 (d18:1(4E))Reach 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. an N-acylsphing-4-enine + UDP-alpha-D-galactose = a beta-D-galactosyl-(1<->1')-N-acylsphing-4-enine + UDP + H(+)
  3. a beta-D-galactosyl-(1<->1')-N-acylsphing-4-enine + CMP-N-acetyl-beta-neuraminate = a ganglioside GM4 (d18:1(4E)) + CMP + H(+)

  Catalysed by GBA1, GBA2, UGT8, ST3GAL5

• N-hexadecanoyl-sphinganine-1-phosphocholineReach from here →
  1. a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol 4-phosphate)(out) + cholesterol(in) = a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol 4-phosphate)(in) + cholesterol(out)
  2. a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol 4-phosphate)(out) + a 1,2-diacyl-sn-glycero-3-phosphocholine(in) = a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol 4-phosphate)(in) + a 1,2-diacyl-sn-glycero-3-phosphocholine(out)
  3. N-hexadecanoylsphinganine + a 1,2-diacyl-sn-glycero-3-phosphocholine = N-hexadecanoyl-sphinganine-1-phosphocholine + a 1,2-diacyl-sn-glycerol

  Catalysed by OSBP, OSBPL3, SGMS1, SGMS2inner side of the membrane, outer side of the membrane

• N-hexadecanoyl-(4R)-hydroxysphinganine-phosphocholineReach from here →
  1. a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol 4-phosphate)(out) + cholesterol(in) = a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol 4-phosphate)(in) + cholesterol(out)
  2. a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol 4-phosphate)(out) + a 1,2-diacyl-sn-glycero-3-phosphocholine(in) = a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol 4-phosphate)(in) + a 1,2-diacyl-sn-glycero-3-phosphocholine(out)
  3. N-hexadecanoyl-(4R)-hydroxysphinganine + a 1,2-diacyl-sn-glycero-3-phosphocholine = N-hexadecanoyl-(4R)-hydroxysphinganine-phosphocholine + a 1,2-diacyl-sn-glycerol

  Catalysed by OSBP, OSBPL3, SGMS1, SGMS2inner side of the membrane, outer side of the membrane

• an N-acyl-(4R)-4-hydroxysphinganine-phosphocholineReach from here →
  1. a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol 4-phosphate)(out) + cholesterol(in) = a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol 4-phosphate)(in) + cholesterol(out)
  2. a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol 4-phosphate)(out) + a 1,2-diacyl-sn-glycero-3-phosphocholine(in) = a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol 4-phosphate)(in) + a 1,2-diacyl-sn-glycero-3-phosphocholine(out)
  3. an N-acyl-(4R)-4-hydroxysphinganine + a 1,2-diacyl-sn-glycero-3-phosphocholine = an N-acyl-(4R)-4-hydroxysphinganine-phosphocholine + a 1,2-diacyl-sn-glycerol

  Catalysed by OSBP, OSBPL3, SGMS1, SGMS2inner side of the membrane, outer side of the membrane

• 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1D-myo-inositol)Reach from here →
  1. cholesterol + (9Z)-octadecenoyl-CoA = cholesteryl (9Z-octadecenoate) + CoA
  2. Steryl-ester acylhydrolase
  3. 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1D-myo-inositol) + H2O = sn-glycero-3-phospho-1D-myo-inositol + (9Z)-octadecenoate + H(+)

  Catalysed by SOAT2, SOAT1, CEL, LIPA and 1 morelysosome

• (11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoateReach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoate + A + H2O

  Catalysed by CH25H, AIFM1, PYROXD1, PTGS2One of 3 routes

• (15R)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (15R)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoate + A + H2O

  Catalysed by CH25H, AIFM1, PYROXD1, PTGS2One of 3 routes

• tricosanoateReach 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. N-Acylsphingosine amidohydrolase
  3. (10Z)-heptadecenoic acid formation

  Catalysed by GBA1, GBA2, ASAH1lysosome, extracellular spaceOne of 12 routes

• 7alpha,25-dihydroxy-4-cholesten-3-oneReach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. cytochrome P450 (25-hydroxycholesterol)
  3. cholest-5-ene-3beta,7alpha,25-triol:NAD+ 3-oxidoreductase

  Catalysed by CH25H, CYP7B1, HSD3B7endoplasmic reticulumOne of 2 routes