N-octadecanoylsphing-4-enine

Three steps

• CHEBI:17808Reach from here →
  1. beta-D-glucosyl-(1<->1)-N-octadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-octadecanoylsphing-4-enine
  2. beta-D-glucosyl-(1<->1)-N-octadecanoylsphing-4-enine + H2O = N-octadecanoylsphing-4-enine + D-glucose
  3. ITP:D-glucose 6-phosphotransferase

  Catalysed by GBA1, GBA3, HK1, HK2 and 2 morecytosol

• a 1,2-diacyl-sn-glycerolReach from here →
  1. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  2. sphing-4-enine + a fatty acyl-CoA = an N-acylsphing-4-enine + CoA + H(+)
  3. ceramide:phosphatidylcholine cholinephosphotransferase

  Catalysed by ASAH1, ACER2, ASAH2, CERS1 and 7 moreGolgi apparatusOne of 9 routes

• 7alpha-hydroxycholest-4-en-3-oneReach from here →
  1. beta-D-glucosyl-(1<->1)-N-octadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-octadecanoylsphing-4-enine
  2. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  3. Cholest-5-Ene-3Beta, 7Alpha-Diol:NAD+ 3-Oxidoreductase Bile Acid Biosynthesis

  Catalysed by GBA1, CH25H, HSD3B7endoplasmic reticulumOne of 5 routes

• D-glucitolReach from here →
  1. beta-D-glucosyl-(1<->1)-N-octadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-octadecanoylsphing-4-enine
  2. beta-D-glucosyl-(1<->1)-N-octadecanoylsphing-4-enine + H2O = N-octadecanoylsphing-4-enine + D-glucose
  3. Aldehyde Reductase

  Catalysed by GBA1, GBA3cytosolOne of 3 routes

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

  Catalysed by ASAH1, ACER2, ASAH2cytosol, extracellular spaceOne of 14 routes

• D-glucosyl-N-acylsphingosineReach from here →
  1. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  2. sphing-4-enine + a fatty acyl-CoA = an N-acylsphing-4-enine + CoA + H(+)
  3. UDP-glucose:N-acylsphingosine D-glucosyltransferase

  Catalysed by ASAH1, ACER2, ASAH2, CERS1 and 6 morecytosolOne of 2 routes

• a beta-D-galactosyl-(1<->1')-N-acylsphing-4-enineReach from here →
  1. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  2. sphing-4-enine + a fatty acyl-CoA = an N-acylsphing-4-enine + CoA + H(+)
  3. an N-acylsphing-4-enine + UDP-alpha-D-galactose = a beta-D-galactosyl-(1<->1')-N-acylsphing-4-enine + UDP + H(+)

  Catalysed by ASAH1, ACER2, ASAH2, CERS1 and 6 moreOne of 3 routes

• 2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-glycerolReach from here →
  1. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  2. 1-octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycerol + H2O = 2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-glycerol + octadecanoate + H(+)
  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 ASAH1, ACER2, ASAH2, ABHD11

• a beta-D-xylosyl-(1<->1')-N-acylsphing-4-enineReach from here →
  1. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  2. sphing-4-enine + a fatty acyl-CoA = an N-acylsphing-4-enine + CoA + H(+)
  3. a beta-D-xylosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-xyloside + an N-acylsphing-4-enine

  Catalysed by ASAH1, ACER2, ASAH2, CERS1 and 7 moreOne of 3 routes

• beta-D-xylosyl-(1<->1')-N-(9Z-octadecenoyl)-sphing-4-enineReach from here →
  1. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  2. N-(9Z-octadecenoyl)-sphing-4-enine + H2O = sphing-4-enine + (9Z)-octadecenoate
  3. N-(9Z-octadecenoyl)-sphing-4-enine + UDP-alpha-D-xylose = beta-D-xylosyl-(1<->1')-N-(9Z-octadecenoyl)-sphing-4-enine + UDP + H(+)

  Catalysed by ASAH1, ACER2, ASAH2, ACER1 and 2 more

• 1-octadecanoyl-2-acyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. a 2-acyl-sn-glycero-3-phosphoethanolamine + octadecanoyl-CoA = 1-octadecanoyl-2-acyl-sn-glycero-3-phosphoethanolamine + CoA

  Catalysed by ASAH1, ACER2, ASAH2, SLC27A2 and 7 morecytosol

• 1D-myo-inositol 1,4,5-trisphosphateReach from here →
  1. beta-D-glucosyl-(1<->1)-N-octadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-octadecanoylsphing-4-enine
  2. a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol-4,5-bisphosphate)(out) + cholesterol(in) = a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol-4,5-bisphosphate)(in) + cholesterol(out)
  3. a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol-4,5-bisphosphate) + H2O = 1D-myo-inositol 1,4,5-trisphosphate + a 1,2-diacyl-sn-glycerol + H(+)

  Catalysed by GBA1, OSBP2, OSBPL2, PLCH2 and 12 moreinner side of the membrane, outer side of the membrane

• a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enineReach from here →
  1. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  2. sphing-4-enine + a fatty acyl-CoA = an N-acylsphing-4-enine + CoA + H(+)
  3. an N-acylsphing-4-enine + UDP-alpha-D-glucose = a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + UDP + H(+)

  Catalysed by ASAH1, ACER2, ASAH2, CERS1 and 6 moreOne of 3 routes

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

  Catalysed by ASAH1, ACER2, ASAH2cytosol, extracellular spaceOne of 12 routes

• octanoateReach from here →
  1. beta-D-glucosyl-(1<->1)-N-octadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-octadecanoylsphing-4-enine
  2. beta-D-glucosyl-N-octanoylsphing-4E-enine + cholesterol = N-octanoylsphing-4-enine + cholesteryl 3-beta-D-glucoside
  3. N-octanoylsphing-4-enine + H2O = octanoate + sphing-4-enine

  Catalysed by GBA1, ASAH1, ASAH2

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

  Catalysed by ASAH1, ACER2, ASAH2cytosol, extracellular spaceOne of 12 routes

• elaidic acidReach from here →
  1. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. stearoyl-CoA 9-desaturase (stearoyl-CoA)

  Catalysed by ASAH1, ACER2, ASAH2, SLC27A2 and 8 morecytosolOne of 14 routes

• alpha-D-galactoseReach from here →
  1. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  2. UDP-alpha-D-galactose:sphingosine 1-beta-galactosyltransferase
  3. galactosylceramidase (psychosine)

  Catalysed by ASAH1, ACER2, ASAH2, GALCcytosol, lysosome

• all-cis-docosa-4,7,10,13,16,19-hexaenoic acidReach from here →
  1. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by ASAH1, ACER2, ASAH2cytosol, extracellular spaceOne of 12 routes

• 1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  2. 1-O-hexadecyl-2-acetyl-sn-glycero-3-phosphocholine + sphing-4-enine = 1-O-hexadecyl-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine + H(+)
  3. 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine = 1-(9Z-octadecenoyl)-N-(acetyl)-sphing-4-enine + 1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine

  Catalysed by ASAH1, ACER2, ASAH2, PAFAH2 and 1 moreOne of 4 routes

• 17alpha-hydroxypregnenoloneReach from here →
  1. beta-D-glucosyl-(1<->1)-N-octadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-octadecanoylsphing-4-enine
  2. 6 reduced [adrenodoxin] + cholesterol + 3 O2 + 6 H(+) = 4-methylpentanal + pregnenolone + 6 oxidized [adrenodoxin] + 4 H2O
  3. cytochrome P450 (pregnenolone)

  Catalysed by GBA1, CYP11A1, CYP17A1cytosolOne of 3 routes

• a fatty acidReach from here →
  1. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  2. sphing-4-enine + a fatty acyl-CoA = an N-acylsphing-4-enine + CoA + H(+)
  3. an N-acylsphing-4-enine + H2O = sphing-4-enine + a fatty acid

  Catalysed by ASAH1, ACER2, ASAH2, CERS1 and 8 moreOne of 2 routes

• phosphocholineReach from here →
  1. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  2. 1-O-hexadecyl-2-acetyl-sn-glycero-3-phosphocholine + sphing-4-enine = 1-O-hexadecyl-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine + H(+)
  3. 1-O-hexadecyl-sn-glycero-3-phosphocholine + H2O = 1-O-hexadecyl-sn-glycerol + phosphocholine + H(+)

  Catalysed by ASAH1, ACER2, ASAH2, PAFAH2 and 1 moreOne of 2 routes

• acetateReach from here →
  1. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  2. 1-O-hexadecyl-2-acetyl-sn-glycero-3-phosphocholine + sphing-4-enine = 1-O-hexadecyl-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine + H(+)
  3. N-(acetyl)-sphing-4-enine + H2O = sphing-4-enine + acetate

  Catalysed by ASAH1, ACER2, ASAH2, PAFAH2

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

  Catalysed by ASAH1, ACER2, ASAH2cytosol, extracellular spaceOne of 13 routes

• (9Z)-octadecenoateReach from here →
  1. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by ASAH1, ACER2, ASAH2cytosol, extracellular spaceOne of 17 routes

• a 1-O-alkyl-sn-glycero-3-phosphocholineReach from here →
  1. beta-D-glucosyl-(1<->1)-N-octadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-octadecanoylsphing-4-enine
  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-alkyl-2-acetyl-sn-glycero-3-phosphocholine + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 1-hexadecanoyl-2-acetyl-sn-glycero-3-phosphocholine + a 1-O-alkyl-sn-glycero-3-phosphocholine

  Catalysed by GBA1, LCAT

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

  Catalysed by ASAH1, ACER2, ASAH2cytosol, extracellular spaceOne of 12 routes

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

  Catalysed by ASAH1, ACER2, ASAH2cytosol, extracellular spaceOne of 13 routes

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

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

• octadecan-1-olReach from here →
  1. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. octadecanoyl-CoA + 2 NADPH + 2 H(+) = octadecan-1-ol + 2 NADP(+) + CoA

  Catalysed by ASAH1, ACER2, ASAH2, SLC27A2 and 8 morecytosol

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

  Catalysed by ASAH1, ACER2, ASAH2cytosol, extracellular spaceOne of 13 routes

• (9Z)-hexadecenoateReach from here →
  1. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by ASAH1, ACER2, ASAH2cytosol, extracellular spaceOne of 12 routes

• (15Z)-tetracosenoateReach from here →
  1. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by ASAH1, ACER2, ASAH2cytosol, extracellular spaceOne of 13 routes

• (5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by ASAH1, ACER2, ASAH2cytosol, extracellular spaceOne of 13 routes

• (11Z)-eicosenoateReach from here →
  1. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by ASAH1, ACER2, ASAH2cytosol, extracellular spaceOne of 12 routes

• 1-O-hexadecyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphocholineReach from here →
  1. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  2. 1-O-hexadecyl-2-acetyl-sn-glycero-3-phosphocholine + sphing-4-enine = 1-O-hexadecyl-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine + H(+)
  3. 1-O-hexadecyl-sn-glycero-3-phosphocholine + (9Z)-octadecenoyl-CoA = 1-O-hexadecyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by ASAH1, ACER2, ASAH2, PAFAH2 and 1 more

• 1-O-hexadecyl-sn-glycerolReach from here →
  1. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  2. 1-O-hexadecyl-2-acetyl-sn-glycero-3-phosphocholine + sphing-4-enine = 1-O-hexadecyl-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine + H(+)
  3. 1-O-hexadecyl-sn-glycero-3-phosphocholine + H2O = 1-O-hexadecyl-sn-glycerol + phosphocholine + H(+)

  Catalysed by ASAH1, ACER2, ASAH2, PAFAH2 and 1 more

• alpha-lactoseReach from here →
  1. beta-D-glucosyl-(1<->1)-N-octadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-octadecanoylsphing-4-enine
  2. beta-D-glucosyl-(1<->1)-N-octadecanoylsphing-4-enine + H2O = N-octadecanoylsphing-4-enine + D-glucose
  3. UDP-alpha-D-galactose:D-glucose 4-beta-D-galactosyltransferase

  Catalysed by GBA1, GBA3, B4GALT2, LALBA and 1 moreGolgi apparatus

• 7alpha,25-dihydroxycholesterolReach from here →
  1. beta-D-glucosyl-(1<->1)-N-octadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-octadecanoylsphing-4-enine
  2. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  3. cytochrome P450 (25-hydroxycholesterol)

  Catalysed by GBA1, CH25H, CYP7B1endoplasmic reticulumOne of 2 routes

• (24S)-7alpha-dihydroxycholesterolReach from here →
  1. beta-D-glucosyl-(1<->1)-N-octadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-octadecanoylsphing-4-enine
  2. cholesterol + reduced [NADPH--hemoprotein reductase] + O2 = 7alpha-hydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
  3. 7alpha-hydroxycholesterol + reduced [NADPH--hemoprotein reductase] + O2 = (24S)-7alpha-dihydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by GBA1, CYP7A1, CYP46A1One of 4 routes

• D-glucopyranose 6-phosphateReach from here →
  1. beta-D-glucosyl-(1<->1)-N-octadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-octadecanoylsphing-4-enine
  2. beta-D-glucosyl-(1<->1)-N-octadecanoylsphing-4-enine + H2O = N-octadecanoylsphing-4-enine + D-glucose
  3. ATP:D-glucose 6-phosphotransferase

  Catalysed by GBA1, GBA3, HK1, GCK and 3 morecytosolOne of 5 routes

• 1-O-hexadecyl-2-acetyl-sn-glycero-3-phosphocholineReach from here →
  1. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  2. 1-O-hexadecyl-2-acetyl-sn-glycero-3-phosphocholine + sphing-4-enine = 1-O-hexadecyl-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine + H(+)
  3. 1-O-hexadecyl-sn-glycero-3-phosphocholine + acetyl-CoA = 1-O-hexadecyl-2-acetyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by ASAH1, ACER2, ASAH2, PAFAH2 and 2 more

• 1-O-hexadecyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholineReach from here →
  1. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  2. 1-O-hexadecyl-2-acetyl-sn-glycero-3-phosphocholine + sphing-4-enine = 1-O-hexadecyl-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine + H(+)
  3. 1-O-hexadecyl-sn-glycero-3-phosphocholine + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-O-hexadecyl-2-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by ASAH1, ACER2, ASAH2, PAFAH2 and 1 moreOne of 2 routes

• a 1,2-diacyl-sn-glycero-3-phospho-L-serineReach from here →
  1. beta-D-glucosyl-(1<->1)-N-octadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-octadecanoylsphing-4-enine
  2. 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)
  3. a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol 4-phosphate)(out) + a 1,2-diacyl-sn-glycero-3-phospho-L-serine(in) = a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol 4-phosphate)(in) + a 1,2-diacyl-sn-glycero-3-phospho-L-serine(out)

  Catalysed by GBA1, OSBP, OSBPL9, OSBPL11 and 4 moreinner side of the membrane, outer side of the membraneOne of 2 routes

• (9Z)-octadecenoyl-CoAReach from here →
  1. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O

  Catalysed by ASAH1, ACER2, ASAH2, SLC27A2 and 8 morecytosol

• 7,8-dihydrofolateReach from here →
  1. beta-D-glucosyl-(1<->1)-N-octadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-octadecanoylsphing-4-enine
  2. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  3. uridine(34) in tRNA + 5,10-methylenetetrahydrofolate + taurine + GTP + A + H2O = 5-taurinomethyluridine(34) in tRNA + 7,8-dihydrofolate + GDP + AH2 + phosphate + H(+)

  Catalysed by GBA1, CH25H, MTO1

• 1-hexadecanoyl-sn-glycero-3-phosphateReach from here →
  1. beta-D-glucosyl-(1<->1)-N-octadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-octadecanoylsphing-4-enine
  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-glycero-3-phosphate + choline + H(+)

  Catalysed by GBA1, LCAT, ENPP2, GDPD3 and 1 more

• a 1,2-diacyl-sn-glycero-3-phosphocholineReach from here →
  1. beta-D-glucosyl-(1<->1)-N-octadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-octadecanoylsphing-4-enine
  2. 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)
  3. 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)

  Catalysed by GBA1, OSBP, OSBPL3inner side of the membrane, outer side of the membraneOne of 2 routes

• an N-acylsphing-4-enine 1-phosphateReach from here →
  1. N-octadecanoylsphing-4-enine + H2O = sphing-4-enine + octadecanoate
  2. sphing-4-enine + a fatty acyl-CoA = an N-acylsphing-4-enine + CoA + H(+)
  3. an N-acylsphing-4-enine + ATP = an N-acylsphing-4-enine 1-phosphate + ADP + H(+)

  Catalysed by ASAH1, ACER2, ASAH2, CERS1 and 7 more