N-(15Z-tetracosenoyl)-sphing-4-enine

Three steps

• hexadecanoateReach from here →
  1. N-(15Z-tetracosenoyl)-sphing-4-enine + H2O = (15Z)-tetracosenoate + sphing-4-enine
  2. sphing-4-enine + hexadecanoyl-CoA = N-hexadecanoylsphing-4-enine + CoA + H(+)
  3. N-hexadecanoylsphing-4-enine + H2O = sphing-4-enine + hexadecanoate

  Catalysed by ACER2, ACER1, ASAH2, CERS6 and 5 moreOne of 2 routes

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

  Catalysed by ACER2, ACER1, ASAH2cytosol, extracellular spaceOne of 12 routes

• 7alpha-hydroxypregnenoloneReach from here →
  1. beta-D-glucosyl-(1<->1')-N-(15Z-tetracosenoyl)-sphing-4-enine + cholesterol = N-(15Z-tetracosenoyl)-sphing-4-enine + cholesteryl 3-beta-D-glucoside
  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 GBA1, CYP11A1, CYP7B1cytosolOne of 2 routes

• (24S)-24-hydroxycholesterol esterReach from here →
  1. beta-D-glucosyl-(1<->1')-N-(15Z-tetracosenoyl)-sphing-4-enine + cholesterol = N-(15Z-tetracosenoyl)-sphing-4-enine + cholesteryl 3-beta-D-glucoside
  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 GBA1, CYP46A1, LCAT

• (24S)-hydroxycholesterol 3-linoleoateReach from here →
  1. beta-D-glucosyl-(1<->1')-N-(15Z-tetracosenoyl)-sphing-4-enine + cholesterol = N-(15Z-tetracosenoyl)-sphing-4-enine + cholesteryl 3-beta-D-glucoside
  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 GBA1, CYP46A1, LCAT

• 1,2-dihexadecanoyl-sn-glycerolReach from here →
  1. N-(15Z-tetracosenoyl)-sphing-4-enine + H2O = (15Z)-tetracosenoate + sphing-4-enine
  2. sphing-4-enine + a fatty acyl-CoA = an N-acylsphing-4-enine + CoA + H(+)
  3. 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine + an N-acylsphing-4-enine = 1,2-dihexadecanoyl-sn-glycerol + a sphingomyelin

  Catalysed by ACER2, ACER1, ASAH2, CERS1 and 6 more

• 1-hexadecanoyl-2-eicosanoyl-sn-glycero-3-phosphocholineReach from here →
  1. beta-D-glucosyl-(1<->1')-N-(15Z-tetracosenoyl)-sphing-4-enine + cholesterol = N-(15Z-tetracosenoyl)-sphing-4-enine + cholesteryl 3-beta-D-glucoside
  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 GBA1, LCAT, LPCAT1

• 1-(9Z-octadecenoyl)-2-acyl-sn-3-glycerolReach from here →
  1. N-(15Z-tetracosenoyl)-sphing-4-enine + H2O = (15Z)-tetracosenoate + sphing-4-enine
  2. sphing-4-enine + a fatty acyl-CoA = an N-acylsphing-4-enine + CoA + H(+)
  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 ACER2, ACER1, ASAH2, CERS1 and 7 more

• 1-octadecanoyl-sn-glycero-3-phosphoserineReach from here →
  1. N-(15Z-tetracosenoyl)-sphing-4-enine + H2O = (15Z)-tetracosenoate + sphing-4-enine
  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-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-L-serine + N-(acetyl)-sphing-4-enine = 1-octadecanoyl-sn-glycero-3-phosphoserine + 1-(9Z-octadecenoyl)-N-(acetyl)-sphing-4-enine

  Catalysed by ACER2, ACER1, ASAH2, PAFAH2 and 1 more

• 1-O-acyl-N-(acetyl)-sphing-4-enineReach from here →
  1. N-(15Z-tetracosenoyl)-sphing-4-enine + H2O = (15Z)-tetracosenoate + sphing-4-enine
  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 + a 1,2-diacyl-sn-glycero-3-phosphocholine = 1-O-acyl-N-(acetyl)-sphing-4-enine + a 1-acyl-sn-glycero-3-phosphocholine

  Catalysed by ACER2, ACER1, ASAH2, PAFAH2 and 1 moreOne of 8 routes

• beta-D-glucosyl-(1<->1')-N-hexadecanoylsphing-4-enineReach from here →
  1. N-(15Z-tetracosenoyl)-sphing-4-enine + H2O = (15Z)-tetracosenoate + sphing-4-enine
  2. sphing-4-enine + hexadecanoyl-CoA = N-hexadecanoylsphing-4-enine + CoA + H(+)
  3. beta-D-glucosyl-(1<->1')-N-hexadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-hexadecanoylsphing-4-enine

  Catalysed by ACER2, ACER1, ASAH2, CERS6 and 4 moreOne of 2 routes

• beta-D-glucosyl-(1<->1)-N-octadecanoylsphing-4-enineReach from here →
  1. N-(15Z-tetracosenoyl)-sphing-4-enine + H2O = (15Z)-tetracosenoate + sphing-4-enine
  2. sphing-4-enine + octadecanoyl-CoA = N-octadecanoylsphing-4-enine + CoA + H(+)
  3. beta-D-glucosyl-(1<->1)-N-octadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-octadecanoylsphing-4-enine

  Catalysed by ACER2, ACER1, ASAH2, CERS1 and 4 moreOne of 2 routes

• N-(acetyl)-sphing-4-enine-1-phosphateReach from here →
  1. N-(15Z-tetracosenoyl)-sphing-4-enine + H2O = (15Z)-tetracosenoate + sphing-4-enine
  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 + ATP = N-(acetyl)-sphing-4-enine-1-phosphate + ADP + H(+)

  Catalysed by ACER2, ACER1, ASAH2, PAFAH2 and 1 more

• 24S,25-dihydroxycholesterolReach from here →
  1. beta-D-glucosyl-(1<->1')-N-(15Z-tetracosenoyl)-sphing-4-enine + cholesterol = N-(15Z-tetracosenoyl)-sphing-4-enine + cholesteryl 3-beta-D-glucoside
  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 GBA1, CYP46A1

• (24S,25R)-24,26-dihydroxycholesterolReach from here →
  1. beta-D-glucosyl-(1<->1')-N-(15Z-tetracosenoyl)-sphing-4-enine + cholesterol = N-(15Z-tetracosenoyl)-sphing-4-enine + cholesteryl 3-beta-D-glucoside
  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 GBA1, CYP46A1