(5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-cholesterol

Three steps

• (4Z,7Z,10Z,13Z)-hexadecatetraenoyl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. Fatty Acid Beta Oxidation (C18:4->C16:4), Mitochondrial

  Catalysed by CEL, LIPA, SOAT2, SOAT1 and 3 morelysosome, endoplasmic reticulum, mitochondrial matrixOne of 3 routes

• (7Z,10Z)-hexadecadienoyl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. Fatty Acid Beta Oxidation Trans (C18:2->C16:2), Mitochondrial

  Catalysed by CEL, LIPA, SOAT2, SOAT1 and 3 morelysosome, endoplasmic reticulum, mitochondrial matrix

• (4Z,7Z)-decadienoyl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. Fatty Acid Beta Oxidation (C12:3->C10:2), Mitochondrial

  Catalysed by CEL, LIPA, SOAT2, SOAT1 and 3 morelysosome, endoplasmic reticulum, mitochondrial matrixOne of 2 routes

• (5Z)-octenoyl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. Fatty Acid Beta Oxidation (C10:2->C8:1), Mitochondrial

  Catalysed by CEL, LIPA, SOAT2, SOAT1 and 3 morelysosome, endoplasmic reticulum, mitochondrial matrixOne of 2 routes

• leukotriene A5Reach from here →
  1. Steryl-ester acylhydrolase
  2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + O2 = (5S)-hydroperoxy-(6E,8Z,11Z,14Z,17Z)-eicosapentaenoate
  3. (5S)-hydroperoxy-(6E,8Z,11Z,14Z,17Z)-eicosapentaenoate = leukotriene A5 + H2O

  Catalysed by CEL, LIPA, ALOX5lysosome

• docosanoateReach from here →
  1. Steryl-ester acylhydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by CEL, LIPAlysosome, cytosol, extracellular spaceOne of 12 routes

• octadecanoateReach from here →
  1. Steryl-ester acylhydrolase
  2. Acyl-CoA:cholesterol O-acyltransferase
  3. Steryl-ester acylhydrolase

  Catalysed by CEL, LIPA, SOAT2, SOAT1lysosome, endoplasmic reticulumOne of 14 routes

• alpha-linolenic acidReach from here →
  1. Steryl-ester acylhydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by CEL, LIPAlysosome, cytosol, extracellular spaceOne of 12 routes

• CHEBI:27540Reach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. medium-chain acyl-CoA ligase (hexanoic acid)

  Catalysed by CEL, LIPA, SOAT2, SOAT1 and 6 morelysosome, endoplasmic reticulum, cytosolOne of 6 routes

• 7-dehydrodesmosterolReach from here →
  1. Steryl-ester acylhydrolase
  2. 3-hydroxyacyl-CoA dehydrogenase (desmosterol)
  3. 7-Dehydrocholesterol Reductase

  Catalysed by CEL, LIPA, DHCR7lysosome, nucleus

• elaidic acidReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. long-chain-fatty-acid-CoA ligase (elaidate)

  Catalysed by CEL, LIPA, SOAT2, SOAT1 and 8 morelysosome, endoplasmic reticulum, cytosolOne of 17 routes

• all-cis-docosa-4,7,10,13,16,19-hexaenoic acidReach from here →
  1. Steryl-ester acylhydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by CEL, LIPAlysosome, cytosol, extracellular spaceOne of 12 routes

• CHEBI:28701Reach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. Propanoyl-CoA:acetyl-CoA C-acyltransferase

  Catalysed by CEL, LIPA, SOAT2, SOAT1 and 3 morelysosome, endoplasmic reticulum, peroxisomeOne of 7 routes

• 17alpha-hydroxypregnenoloneReach from here →
  1. Steryl-ester acylhydrolase
  2. cytochrome P450 (cholesterol)
  3. cytochrome P450 (pregnenolone)

  Catalysed by CEL, LIPA, CYP11A1, CYP17A1lysosome, mitochondrial matrix, cytosolOne of 3 routes

• tetradecanoateReach from here →
  1. Steryl-ester acylhydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by CEL, LIPAlysosome, cytosol, extracellular spaceOne of 12 routes

• (9Z)-octadecenoateReach from here →
  1. Steryl-ester acylhydrolase
  2. Acyl-CoA:cholesterol O-acyltransferase
  3. Steryl-ester acylhydrolase

  Catalysed by CEL, LIPA, SOAT2, SOAT1lysosome, endoplasmic reticulumOne of 15 routes

• hexacosanoateReach from here →
  1. Steryl-ester acylhydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by CEL, LIPAlysosome, cytosol, extracellular spaceOne of 12 routes

• tetracosanoateReach from here →
  1. Steryl-ester acylhydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by CEL, LIPAlysosome, cytosol, extracellular spaceOne of 12 routes

• an N-acylsphinganineReach from here →
  1. Steryl-ester acylhydrolase
  2. (10Z)-heptadecenoic acid formation
  3. N-acylsphingosine amidohydrolase

  Catalysed by CEL, LIPA, ASAH1, ACER2 and 3 morelysosome, cytosol

• eicosanoateReach from here →
  1. Steryl-ester acylhydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by CEL, LIPAlysosome, cytosol, extracellular spaceOne of 12 routes

• (9Z)-hexadecenoateReach from here →
  1. Steryl-ester acylhydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by CEL, LIPAlysosome, cytosol, extracellular spaceOne of 12 routes

• (15Z)-tetracosenoateReach from here →
  1. Steryl-ester acylhydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by CEL, LIPAlysosome, cytosol, extracellular spaceOne of 12 routes

• (5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. Steryl-ester acylhydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by CEL, LIPAlysosome, cytosol, extracellular spaceOne of 12 routes

• (11Z)-eicosenoateReach from here →
  1. Steryl-ester acylhydrolase
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by CEL, LIPAlysosome, cytosol, extracellular spaceOne of 12 routes

• a fatty aldehydeReach from here →
  1. cholesterol-ester plasma pool to cholesterol-ester-10,13,16,19-docosa conversion
  2. a cholesterol ester + H2O = cholesterol + a fatty acid + H(+)
  3. a fatty aldehyde + NAD(+) + H2O = a fatty acid + NADH + 2 H(+)

  Catalysed by CES1, LIPN, NCEH1, LDAH and 1 moreendoplasmic reticulum

• 7alpha,25-dihydroxycholesterolReach from here →
  1. Steryl-ester acylhydrolase
  2. cholesterol 25-hydroxylase (cholesterol)
  3. cytochrome P450 (25-hydroxycholesterol)

  Catalysed by CEL, LIPA, CH25H, CYP7B1lysosome, endoplasmic reticulumOne of 2 routes

• (24S)-7alpha-dihydroxycholesterolReach from here →
  1. Steryl-ester acylhydrolase
  2. Cytochrome P450, Family 46, Subfamily A, Polypeptide 1
  3. Oxysterol 7-Alpha-Hydroxylase

  Catalysed by CEL, LIPA, CYP46A1, CYP39A1lysosome, endoplasmic reticulumOne of 4 routes

• N-octanoylsphing-4-enineReach from here →
  1. cholesterol-ester plasma pool to cholesterol-ester-10,13,16,19-docosa conversion
  2. a cholesterol ester + H2O = cholesterol + a fatty acid + H(+)
  3. beta-D-glucosyl-N-octanoylsphing-4E-enine + cholesterol = N-octanoylsphing-4-enine + cholesteryl 3-beta-D-glucoside

  Catalysed by CES1, LIPN, NCEH1, LDAH and 1 moreendoplasmic reticulum

• (24R)-hydroxycholesterolReach from here →
  1. cholesterol-ester plasma pool to cholesterol-ester-10,13,16,19-docosa conversion
  2. a cholesterol ester + H2O = cholesterol + a fatty acid + H(+)
  3. cholesterol + reduced [NADPH--hemoprotein reductase] + O2 = (24R)-hydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CES1, LIPN, NCEH1, LDAH and 1 moreendoplasmic reticulum

• taurineReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)

  Catalysed by CEL, LIPA, SOAT2, SOAT1 and 1 morelysosome, endoplasmic reticulum, cytosolOne of 2 routes

• an N-acylsphing-4-enineReach from here →
  1. cholesterol-ester plasma pool to cholesterol-ester-10,13,16,19-docosa conversion
  2. a cholesterol ester + H2O = cholesterol + a fatty acid + H(+)
  3. a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + an N-acylsphing-4-enine

  Catalysed by CES1, LIPN, NCEH1, LDAH and 2 moreendoplasmic reticulumOne of 3 routes

• glycineReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. glycine N-acyltransferase (N-arachidonoylglycine)

  Catalysed by CEL, LIPA, SOAT2, SOAT1 and 3 morelysosome, endoplasmic reticulum, mitochondrial matrixOne of 10 routes

• (R)-methylmalonyl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. aldehyde dehydrogenase (2-methyl-3-oxopropanoate)

  Catalysed by CEL, LIPA, SOAT2, SOAT1 and 1 morelysosome, endoplasmic reticulum, mitochondrial matrixOne of 2 routes

• (S)-methylmalonyl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. (S)-methylmalonyl-CoA hydrolase

  Catalysed by CEL, LIPA, SOAT2, SOAT1lysosome, endoplasmic reticulum, mitochondrial matrix

• 3'-dephospho-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. acid phosphatase 2, lysosomal (CoA)

  Catalysed by CEL, LIPA, SOAT2, SOAT1 and 1 morelysosome, endoplasmic reticulumOne of 2 routes

• (2E)-dodecenoyl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. (2E)-dodecenoyl-CoA formation

  Catalysed by CEL, LIPA, SOAT2, SOAT1lysosome, endoplasmic reticulum, mitochondrial matrixOne of 3 routes

• 4,8,12-trimethyltridecanoyl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. propanoyl-CoA C-acyltransferase (3-ketopristanoyl-CoA)

  Catalysed by CEL, LIPA, SOAT2, SOAT1 and 2 morelysosome, endoplasmic reticulum, peroxisomeOne of 2 routes

• (6Z,9Z,12Z)-octadecatrienoyl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. long-chain-fatty-acid-CoA ligase (gamma-linolenate)

  Catalysed by CEL, LIPA, SOAT2, SOAT1 and 8 morelysosome, endoplasmic reticulum, cytosolOne of 7 routes

• butanoyl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. Butanoate:CoA ligase (AMP-forming)

  Catalysed by CEL, LIPA, SOAT2, SOAT1 and 6 morelysosome, endoplasmic reticulum, cytosolOne of 9 routes

• dodecanoyl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. long-chain-fatty-acid-CoA ligase (lauric acid)

  Catalysed by CEL, LIPA, SOAT2, SOAT1 and 8 morelysosome, endoplasmic reticulum, cytosolOne of 9 routes

• glutaryl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. Production of Glutaryl Carnitine

  Catalysed by CEL, LIPA, SOAT2, SOAT1 and 3 morelysosome, endoplasmic reticulum, cytosolOne of 2 routes

• eicosanoyl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. long-chain-fatty-acid-CoA ligase (eicosanoate)

  Catalysed by CEL, LIPA, SOAT2, SOAT1 and 8 morelysosome, endoplasmic reticulum, cytosolOne of 12 routes

• itaconyl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. Itaconate:CoA ligase (GDP-forming)

  Catalysed by CEL, LIPA, SOAT2, SOAT1 and 3 morelysosome, endoplasmic reticulum, mitochondrial matrixOne of 2 routes

• (9Z,12Z)-octadecadienoyl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)

  Catalysed by CEL, LIPA, SOAT2, SOAT1 and 8 morelysosome, endoplasmic reticulum, cytosolOne of 13 routes

• tetradecanoyl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. long-chain-fatty-acid-CoA ligase (myristic acid)

  Catalysed by CEL, LIPA, SOAT2, SOAT1 and 8 morelysosome, endoplasmic reticulum, cytosolOne of 11 routes

• octanoyl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. Octanoyl-CoA:L-carnitine O-octanoyltransferase

  Catalysed by CEL, LIPA, SOAT2, SOAT1 and 1 morelysosome, endoplasmic reticulum, mitochondrial matrixOne of 20 routes

• phytanoyl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. phytanate-CoA ligase

  Catalysed by CEL, LIPA, SOAT2, SOAT1lysosome, endoplasmic reticulum, cytosolOne of 5 routes

• octadecanoyl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. long-chain-fatty-acid-CoA ligase (stearate)

  Catalysed by CEL, LIPA, SOAT2, SOAT1 and 7 morelysosome, endoplasmic reticulum, cytosolOne of 15 routes

• 7,8-dihydrofolateReach from here →
  1. Steryl-ester acylhydrolase
  2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (18R)-hydroxy-(5Z,8Z,11Z,14Z,16E)-eicosapentaenoate + 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 CEL, LIPA, PTGS2, MTO1lysosome

• sphing-4-enineReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. acyl-CoA:sphingosine N-acyltransferase

  Catalysed by CEL, LIPA, SOAT2, SOAT1 and 4 morelysosome, endoplasmic reticulum, Golgi apparatusOne of 2 routes