1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate

Three steps

• pregn-5-ene-3,20-dioneReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(out) + cholesterol(in) = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(in) + cholesterol(out)
  2. 6 reduced [adrenodoxin] + cholesterol + 3 O2 + 6 H(+) = 4-methylpentanal + pregnenolone + 6 oxidized [adrenodoxin] + 4 H2O
  3. Pregnenolone:NAD+ 3-oxidoreductase

  Catalysed by OSBPL2, CYP11A1, HSD3B1, HSD3B2inner side of the membrane, outer side of the membrane, cytosolOne of 2 routes

• 4-methylpentan-1-olReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(out) + cholesterol(in) = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(in) + cholesterol(out)
  2. 6 reduced [adrenodoxin] + cholesterol + 3 O2 + 6 H(+) = 4-methylpentanal + pregnenolone + 6 oxidized [adrenodoxin] + 4 H2O
  3. aldose reductase (isocaproic-aldehyde)

  Catalysed by OSBPL2, CYP11A1, AKR1B10, AKR1B1inner side of the membrane, outer side of the membrane, cytosolOne of 2 routes

• a 1-acyl-2-hexadecanoyl-sn-glycero-3-phospho-(1D-myo-inositol)Reach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(out) + cholesterol(in) = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(in) + cholesterol(out)
  2. 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
  3. a 1-acyl-sn-glycero-3-phospho-(1D-myo-inositol) + 1-hexadecanoyl-sn-glycero-3-phosphocholine = a 1-acyl-2-hexadecanoyl-sn-glycero-3-phospho-(1D-myo-inositol) + sn-glycerol 3-phosphocholine

  Catalysed by OSBPL2, LCAT, ASPGinner side of the membrane, outer side of the membrane

• beta-D-glucosyl-N-octanoylsphing-4E-enineReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(out) + cholesterol(in) = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(in) + cholesterol(out)
  2. a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + an N-acylsphing-4-enine
  3. beta-D-glucosyl-N-octanoylsphing-4E-enine + cholesterol = N-octanoylsphing-4-enine + cholesteryl 3-beta-D-glucoside

  Catalysed by OSBPL2, GBA1, GBA2inner side of the membrane, outer side of the membraneOne of 2 routes

• Mo-molybdopterinReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(out) + cholesterol(in) = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(in) + cholesterol(out)
  2. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  3. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O

  Catalysed by OSBPL2, CH25H, MOCOSinner side of the membrane, outer side of the membrane

• (8Z,11Z,14Z)-eicosatrienoateReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(out) + cholesterol(in) = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(in) + cholesterol(out)
  2. 1-hexadecanoyl-2-(8Z,11Z,14Z-eicosatrienoyl)-sn-glycero-3-phosphocholine + cholesterol = cholesteryl (8Z,11Z,14Z)-eicosatrienoate + 1-hexadecanoyl-sn-glycero-3-phosphocholine
  3. Steryl-ester acylhydrolase

  Catalysed by OSBPL2, LCAT, CEL, LIPAinner side of the membrane, outer side of the membrane, lysosomeOne of 2 routes

• 1-O-hexadecyl-2-hexadecanoyl-sn-glycero-3-phosphocholineReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(out) + cholesterol(in) = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(in) + cholesterol(out)
  2. 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
  3. 1-O-hexadecyl-sn-glycero-3-phosphocholine + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 1-O-hexadecyl-2-hexadecanoyl-sn-glycero-3-phosphocholine + sn-glycerol 3-phosphocholine

  Catalysed by OSBPL2, LCAT, PLA2G4Cinner side of the membrane, outer side of the membrane

• N-(hexadecanoyl)-sphing-4-enine-1-phosphateReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(out) + cholesterol(in) = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(in) + cholesterol(out)
  2. beta-D-glucosyl-(1<->1')-N-hexadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-hexadecanoylsphing-4-enine
  3. N-hexadecanoylsphing-4-enine + ATP = N-(hexadecanoyl)-sphing-4-enine-1-phosphate + ADP + H(+)

  Catalysed by OSBPL2, GBA1, CERKinner side of the membrane, outer side of the membrane

• 1,2-dihexadecanoyl-sn-glycero-3-phosphocholineReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(out) + cholesterol(in) = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(in) + cholesterol(out)
  2. 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
  3. 1-hexadecanoyl-sn-glycero-3-phosphocholine + hexadecanoyl-CoA = 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by OSBPL2, LCAT, PRDX6, LPCAT3 and 1 moreinner side of the membrane, outer side of the membraneOne of 4 routes

• 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholineReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(out) + cholesterol(in) = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(in) + cholesterol(out)
  2. 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
  3. octadecanoyl-CoA + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by OSBPL2, LCAT, LPCAT3inner side of the membrane, outer side of the membrane

• 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(out) + cholesterol(in) = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(in) + cholesterol(out)
  2. 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
  3. 1-hexadecanoyl-sn-glycero-3-phosphocholine + (9Z)-octadecenoyl-CoA = 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + CoA

  Catalysed by OSBPL2, LCAT, LPCAT3, MBOAT1 and 3 moreinner side of the membrane, outer side of the membraneOne of 2 routes

• 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholineReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(out) + cholesterol(in) = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(in) + cholesterol(out)
  2. 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
  3. (9Z,12Z)-octadecadienoyl-CoA + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine + CoA

  Catalysed by OSBPL2, LCAT, LPCAT3, MBOAT2 and 1 moreinner side of the membrane, outer side of the membrane

• 1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(out) + cholesterol(in) = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(in) + cholesterol(out)
  2. 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
  3. (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

  Catalysed by OSBPL2, LCAT, LPCAT3, MBOAT7inner side of the membrane, outer side of the membraneOne of 2 routes

• 1,2-dihexadecanoyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(out) + cholesterol(in) = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(in) + cholesterol(out)
  2. 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
  3. 1-hexadecanoyl-sn-glycero-3-phosphoethanolamine + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 1,2-dihexadecanoyl-sn-glycero-3-phosphoethanolamine + sn-glycerol 3-phosphocholine

  Catalysed by OSBPL2, LCAT, ASPG, PLA2G4Cinner side of the membrane, outer side of the membrane

• an N-acylsphing-4-enine 1-phosphoethanolamineReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(out) + cholesterol(in) = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(in) + cholesterol(out)
  2. a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + an N-acylsphing-4-enine
  3. an N-acylsphing-4-enine + a 1,2-diacyl-sn-glycero-3-phosphoethanolamine = an N-acylsphing-4-enine 1-phosphoethanolamine + a 1,2-diacyl-sn-glycerol

  Catalysed by OSBPL2, GBA1, GBA2, SGMS1 and 2 moreinner side of the membrane, outer side of the membrane

• 1-(beta-D-galactosyl)-N-dodecanoylsphing-4-enineReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(out) + cholesterol(in) = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(in) + cholesterol(out)
  2. a beta-D-galactosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-galactoside + an N-acylsphing-4-enine
  3. 1-(beta-D-galactosyl)-N-dodecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-galactoside + N-dodecanoylsphing-4-enine

  Catalysed by OSBPL2, GBA1, GBA2inner side of the membrane, outer side of the membraneOne of 2 routes

• 1-hexadecanoyl-2-(9Z-hexadecenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(out) + cholesterol(in) = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(in) + cholesterol(out)
  2. 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
  3. (9Z)-hexadecenoyl-CoA + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 1-hexadecanoyl-2-(9Z-hexadecenoyl)-sn-glycero-3-phosphocholine + CoA

  Catalysed by OSBPL2, LCAT, LPCAT3, MBOAT2inner side of the membrane, outer side of the membrane

• 1-hexadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(out) + cholesterol(in) = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(in) + cholesterol(out)
  2. 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
  3. (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

  Catalysed by OSBPL2, LCAT, LPCAT1inner side of the membrane, outer side of the membrane

• 1-hexadecanoyl-2-dodecanoyl-sn-glycero-3-phosphocholineReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(out) + cholesterol(in) = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(in) + cholesterol(out)
  2. 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
  3. dodecanoyl-CoA + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 1-hexadecanoyl-2-dodecanoyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by OSBPL2, LCAT, LPCAT3, LPCAT1inner side of the membrane, outer side of the membrane

• 1-octadecanoyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(out) + cholesterol(in) = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(in) + cholesterol(out)
  2. 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
  3. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphoethanolamine + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 1-octadecanoyl-sn-glycero-3-phosphoethanolamine + 1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine

  Catalysed by OSBPL2, LCAT, PLA2G4Cinner side of the membrane, outer side of the membrane

• 1-hexadecanoyl-2-acetyl-sn-glycero-3-phosphocholineReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(out) + cholesterol(in) = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(in) + cholesterol(out)
  2. 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
  3. 1-hexadecanoyl-sn-glycero-3-phosphocholine + acetyl-CoA = 1-hexadecanoyl-2-acetyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by OSBPL2, LCAT, LPCAT2, LPCAT1inner side of the membrane, outer side of the membraneOne of 2 routes

• 1-hexadecanoyl-2-decanoyl-sn-glycero-3-phosphocholineReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(out) + cholesterol(in) = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(in) + cholesterol(out)
  2. 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
  3. decanoyl-CoA + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 1-hexadecanoyl-2-decanoyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by OSBPL2, LCAT, LPCAT1inner side of the membrane, outer side of the membrane

• 1-hexadecanoyl-2-hexanoyl-sn-glycero-3-phosphocholineReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(out) + cholesterol(in) = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(in) + cholesterol(out)
  2. 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
  3. hexanoyl-CoA + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 1-hexadecanoyl-2-hexanoyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by OSBPL2, LCAT, LPCAT1inner side of the membrane, outer side of the membrane

• 1-hexadecanoyl-2-octanoyl-sn-glycero-3-phosphocholineReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(out) + cholesterol(in) = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(in) + cholesterol(out)
  2. 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
  3. octanoyl-CoA + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 1-hexadecanoyl-2-octanoyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by OSBPL2, LCAT, LPCAT1inner side of the membrane, outer side of the membrane

• 1-hexadecanoyl-2-tetradecanoyl-sn-glycero-3-phosphocholineReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(out) + cholesterol(in) = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(in) + cholesterol(out)
  2. 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
  3. tetradecanoyl-CoA + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 1-hexadecanoyl-2-tetradecanoyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by OSBPL2, LCAT, LPCAT1inner side of the membrane, outer side of the membrane

• 1-hexadecanoyl-sn-glycerolReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(out) + cholesterol(in) = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(in) + cholesterol(out)
  2. 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
  3. 1-hexadecanoyl-sn-glycero-3-phosphocholine + H2O = 1-hexadecanoyl-sn-glycerol + phosphocholine + H(+)

  Catalysed by OSBPL2, LCAT, SMPD2, ENPP6 and 2 moreinner side of the membrane, outer side of the membrane

• 2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholineReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(out) + cholesterol(in) = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(in) + cholesterol(out)
  2. 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
  3. 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine + 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine

  Catalysed by OSBPL2, LCAT, TAFAZZINinner side of the membrane, outer side of the membrane

• beta-D-glucosyl-N-dodecanoylsphing-4-enineReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(out) + cholesterol(in) = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(in) + cholesterol(out)
  2. a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + an N-acylsphing-4-enine
  3. beta-D-glucosyl-N-dodecanoylsphing-4-enine + cholesterol = N-dodecanoylsphing-4-enine + cholesteryl 3-beta-D-glucoside

  Catalysed by OSBPL2, GBA1, GBA2inner side of the membrane, outer side of the membraneOne of 2 routes

• beta-D-glucosyl-(1<->1')-N-(15Z-tetracosenoyl)-sphing-4-enineReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(out) + cholesterol(in) = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(in) + cholesterol(out)
  2. a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + an N-acylsphing-4-enine
  3. beta-D-glucosyl-(1<->1')-N-(15Z-tetracosenoyl)-sphing-4-enine + cholesterol = N-(15Z-tetracosenoyl)-sphing-4-enine + cholesteryl 3-beta-D-glucoside

  Catalysed by OSBPL2, GBA1, GBA2inner side of the membrane, outer side of the membraneOne of 2 routes

• 1-O-(1Z)-alkenyl-2-hexadecanoyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(out) + cholesterol(in) = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(in) + cholesterol(out)
  2. 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
  3. a 1-O-(1Z-alkenyl)-sn-glycero-3-phosphoethanolamine + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 1-O-(1Z)-alkenyl-2-hexadecanoyl-sn-glycero-3-phosphoethanolamine + sn-glycerol 3-phosphocholine

  Catalysed by OSBPL2, LCAT, PLA2G4Cinner side of the membrane, outer side of the membrane

• hexadecanoateReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(out) + cholesterol(in) = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(in) + cholesterol(out)
  2. 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
  3. 1-hexadecanoyl-sn-glycero-3-phosphocholine + H2O = sn-glycerol 3-phosphocholine + hexadecanoate + H(+)

  Catalysed by OSBPL2, LCAT, PLA2G6, LYPLA1 and 15 moreinner side of the membrane, outer side of the membraneOne of 2 routes

• 7alpha-hydroxypregnenoloneReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(out) + cholesterol(in) = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(in) + cholesterol(out)
  2. 6 reduced [adrenodoxin] + cholesterol + 3 O2 + 6 H(+) = 4-methylpentanal + pregnenolone + 6 oxidized [adrenodoxin] + 4 H2O
  3. pregnenolone,NADPH:oxygen oxidoreductase (7alpha-hydroxylating)

  Catalysed by OSBPL2, CYP11A1, CYP7B1inner side of the membrane, outer side of the membrane, cytosolOne of 2 routes

• (24S)-24-hydroxycholesterol esterReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(out) + cholesterol(in) = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(in) + cholesterol(out)
  2. cholesterol + reduced [NADPH--hemoprotein reductase] + O2 = (24S)-hydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
  3. a 1-hexadecanoyl-2-acyl-sn-glycero-3-phosphocholine + (24S)-hydroxycholesterol = (24S)-24-hydroxycholesterol ester + 1-hexadecanoyl-sn-glycero-3-phosphocholine

  Catalysed by OSBPL2, CYP46A1, LCATinner side of the membrane, outer side of the membrane

• (24S)-hydroxycholesterol 3-linoleoateReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(out) + cholesterol(in) = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(in) + cholesterol(out)
  2. cholesterol + reduced [NADPH--hemoprotein reductase] + O2 = (24S)-hydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
  3. (24S)-hydroxycholesterol + 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine = (24S)-hydroxycholesterol 3-linoleoate + 1-hexadecanoyl-sn-glycero-3-phosphocholine

  Catalysed by OSBPL2, CYP46A1, LCATinner side of the membrane, outer side of the membrane

• 1,2-dihexadecanoyl-sn-glycerolReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(out) + cholesterol(in) = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(in) + cholesterol(out)
  2. a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + an N-acylsphing-4-enine
  3. 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine + an N-acylsphing-4-enine = 1,2-dihexadecanoyl-sn-glycerol + a sphingomyelin

  Catalysed by OSBPL2, GBA1, GBA2, SGMS2inner side of the membrane, outer side of the membrane

• 1-hexadecanoyl-2-eicosanoyl-sn-glycero-3-phosphocholineReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(out) + cholesterol(in) = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(in) + cholesterol(out)
  2. 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
  3. eicosanoyl-CoA + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 1-hexadecanoyl-2-eicosanoyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by OSBPL2, LCAT, LPCAT1inner side of the membrane, outer side of the membrane

• 1-(9Z-octadecenoyl)-2-acyl-sn-3-glycerolReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(out) + cholesterol(in) = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(in) + cholesterol(out)
  2. a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + an N-acylsphing-4-enine
  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 OSBPL2, GBA1, GBA2, SGMS1 and 1 moreinner side of the membrane, outer side of the membrane

• beta-D-glucosyl-(1<->1')-N-hexadecanoylsphing-4-enineReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(out) + cholesterol(in) = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(in) + cholesterol(out)
  2. a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + an N-acylsphing-4-enine
  3. beta-D-glucosyl-(1<->1')-N-hexadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-hexadecanoylsphing-4-enine

  Catalysed by OSBPL2, GBA1, GBA2inner side of the membrane, outer side of the membraneOne of 2 routes

• beta-D-glucosyl-(1<->1)-N-octadecanoylsphing-4-enineReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(out) + cholesterol(in) = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(in) + cholesterol(out)
  2. a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + an N-acylsphing-4-enine
  3. beta-D-glucosyl-(1<->1)-N-octadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-octadecanoylsphing-4-enine

  Catalysed by OSBPL2, GBA1, GBA2inner side of the membrane, outer side of the membraneOne of 2 routes

• 24S,25-dihydroxycholesterolReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(out) + cholesterol(in) = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(in) + cholesterol(out)
  2. cholesterol + reduced [NADPH--hemoprotein reductase] + O2 = (24S)-hydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
  3. (24S)-hydroxycholesterol + reduced [NADPH--hemoprotein reductase] + O2 = 24S,25-dihydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by OSBPL2, CYP46A1inner side of the membrane, outer side of the membrane

• (24S,25R)-24,26-dihydroxycholesterolReach from here →
  1. 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(out) + cholesterol(in) = 1-octadecanoyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phospho-1D-myo-inositol 4,5-bisphosphate(in) + cholesterol(out)
  2. cholesterol + reduced [NADPH--hemoprotein reductase] + O2 = (24S)-hydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
  3. (24S)-hydroxycholesterol + reduced [NADPH--hemoprotein reductase] + O2 = (24S,25R)-24,26-dihydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by OSBPL2, CYP46A1inner side of the membrane, outer side of the membrane