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

Three steps

• cholesteryl (7Z)-octadecenoateReach 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. (7Z)-octadecenoyl-CoA + cholesterol = cholesteryl (7Z)-octadecenoate + CoA

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

• (7Z)-octadecenoyl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. carnitine O-palmitoyltransferase ((7Z)-octadecenoyl-CoA)

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

• CHEBI:15345Reach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. Acetoacetate:CoA ligase (AMP-forming)

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

• cholineReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. Acetyl-CoA:choline O-acetyltransferase

  Catalysed by CEL, LIPA, SOAT2, SOAT1 and 1 morelysosome, endoplasmic reticulum, nucleus

• CHEBI:15380Reach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. 5-aminolevulinate synthase (2-amino-3-oxoadipate)

  Catalysed by CEL, LIPA, SOAT2, SOAT1 and 2 morelysosome, endoplasmic reticulum, mitochondrial matrixOne of 8 routes

• CHEBI:15477Reach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. glycine N-acyltransferase (2-methylbutyryl-CoA)

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

• 2-methylcrotonoyl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. Production of Tiglylcarnitine

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

• isobutyryl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. acetyl-CoA C-acyltransferase (3-oxo-4-methyl-pentanoyl-CoA)

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

• 3-methylbut-2-enoyl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. glycine-N-acyltransferase (3-methylcrotonoylglycine)

  Catalysed by CEL, LIPA, SOAT2, SOAT1 and 1 morelysosome, endoplasmic reticulum, mitochondrial matrix

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

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

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

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

• CHEBI:15519Reach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. propanoyl-CoA C-acyltransferase

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

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

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

• oleoyl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. Transport of octadecenoyl-CoA into Mitochondrial Matrix

  Catalysed by CEL, LIPA, SOAT2, SOAT1 and 3 morelysosome, endoplasmic reticulum, cytosolOne of 11 routes

• phenylacetyl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. Phenylacetate:CoA ligase

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

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

  Catalysed by CEL, LIPA, SOAT2, SOAT1 and 3 morelysosome, endoplasmic reticulum, cytosolOne of 43 routes

• 15(S)-HPETEReach from here →
  1. Steryl-ester acylhydrolase
  2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + AH2 + O2 = (15S)-hydroxy-(5Z,8Z,11Z,13E,17Z)-eicosapentaenoate + A + H2O
  3. palmitoyl-CoA hydrolase (15(S)-HPETE)

  Catalysed by CEL, LIPA, PTGS2lysosome, cytosol

• CHEBI:15650Reach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. N-acetyl-LTE4 to leukotriene E4 conversion

  Catalysed by CEL, LIPA, SOAT2, SOAT1 and 32 morelysosome, endoplasmic reticulum, cytosolOne of 2 routes

• betaine aldehydeReach 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. choline + A = betaine aldehyde + AH2

  Catalysed by CEL, LIPA, PTGS2, CHDHlysosome

• CHEBI:15727Reach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. N-alpha-acetyltransferase 10, NatA catalytic subunit (acetylcarnosine)

  Catalysed by CEL, LIPA, SOAT2, SOAT1 and 1 morelysosome, endoplasmic reticulum, cytosol

• CHEBI:15746Reach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. diamine N-acetyltransferase (N1-acetylspermine)

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

• hexadecanoic acidReach 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

• 1,2-diacyl-sn-glycero-3-phosphocholine(1+)Reach from here →
  1. Steryl-ester acylhydrolase
  2. Phosphatidylcholine:sterol O-acyltransferase
  3. Acyl-CoA:1-acyl-sn-glycero-3-phosphocholine O-acyltransferase

  Catalysed by CEL, LIPA, LCAT, LPCAT4 and 3 morelysosome, cytosol

• sulfateReach from here →
  1. Steryl-ester acylhydrolase
  2. 3'-phosphoadenylyl-sulfate:cholesterol sulfotransferase
  3. Cholesterol-sulfate sulfohydrolase

  Catalysed by CEL, LIPA, SULT2B1, SULT1A3 and 1 morelysosome, cytosolOne of 4 routes

• 11-cis-retinolReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. Palmitoyl-CoA:retinol O-acyltransferase

  Catalysed by CEL, LIPA, SOAT2, SOAT1 and 5 morelysosome, endoplasmic reticulum, cytosol

• oxaloacetateReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. ATP citrate lyase (citrate)

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

• formaldehydeReach 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. N(6),N(6)-dimethyl-L-lysyl(4)-[histone H3] + 2 A + 2 H2O = L-lysyl(4)-[histone H3] + 2 formaldehyde + 2 AH2

  Catalysed by CEL, LIPA, PTGS2, KDM1A and 1 morelysosomeOne of 3 routes

• sn-glycerol 3-phosphocholineReach from here →
  1. Steryl-ester acylhydrolase
  2. Phosphatidylcholine:sterol O-acyltransferase
  3. 1-Acyl-sn-glycero-3-phosphocholine acylhydrolase

  Catalysed by CEL, LIPA, LCAT, LYPLA1 and 9 morelysosome, cytosol

• progesteroneReach from here →
  1. Steryl-ester acylhydrolase
  2. cytochrome P450 (cholesterol)
  3. Pregnenolone:NAD+ 3-oxidoreductase

  Catalysed by CEL, LIPA, CYP11A1, HSD3B1 and 1 morelysosome, mitochondrial matrix, cytosolOne of 2 routes

• anilineReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. Acetyl-CoA:arylamine N-acetyltransferase

  Catalysed by CEL, LIPA, SOAT2, SOAT1 and 2 morelysosome, endoplasmic reticulum, cytosol

• CHEBI:17312Reach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. N1,N12-diacetylspermine to N1-acetylspermine conversion

  Catalysed by CEL, LIPA, SOAT2, SOAT1lysosome, endoplasmic reticulum, cytosolOne of 2 routes

• all-trans-retinolReach 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. all-trans-13,14-dihydroretinol + A = all-trans-retinol + AH2

  Catalysed by CEL, LIPA, PTGS2, RETSATlysosome

• linoleic acidReach 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

• a monoacylglycerolReach 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 monoacylglycerol + H2O = glycerol + a fatty acid + H(+)

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

• cholesteryl 3-beta-D-glucosideReach 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 7 routes

• AH2Reach 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. A + NADH + H(+) = AH2 + NAD(+)

  Catalysed by CEL, LIPA, PTGS2, AIFM1 and 1 morelysosomeOne of 19 routes

• L-cysteineReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. N-acetylglutamate synthase (N-acetyl-L-cysteine)

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

• 26-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 = 26-hydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

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

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

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

• 7alpha-hydroxycholest-4-en-3-oneReach from here →
  1. Steryl-ester acylhydrolase
  2. cytochrome P450 (cholesterol)
  3. 7alpha-Hydroxycholesterol:NAD+ 3-oxidoreductase

  Catalysed by CEL, LIPA, CYP7A1, HSD3B7lysosome, endoplasmic reticulumOne of 5 routes

• CHEBI:17927Reach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. N1,N8-diacetylspermidine to N1-acetylspermidine conversion

  Catalysed by CEL, LIPA, SOAT2, SOAT1lysosome, endoplasmic reticulum, cytosol

• dodecanoateReach 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

• (2E,5Z,8Z,11Z,14Z,17Z)-eicosahexaenoyl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. long-chain-fatty-acid-CoA ligase (EPA)
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA + O2 = (2E,5Z,8Z,11Z,14Z,17Z)-eicosahexaenoyl-CoA + H2O2

  Catalysed by CEL, LIPA, SLC27A2, ACSL4 and 7 morelysosome, cytosol

• cholesteryl 3-beta-D-galactosideReach 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-galactosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-galactoside + an N-acylsphing-4-enine

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

• cholesteryl 3-beta-D-xylosideReach 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-xylosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-xyloside + an N-acylsphing-4-enine

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

• (5S)-hydroxy-(6E,8Z,11Z,14Z,17Z)-eicosapentaenoateReach 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 + 2 glutathione = (5S)-hydroxy-(6E,8Z,11Z,14Z,17Z)-eicosapentaenoate + glutathione disulfide + H2O

  Catalysed by CEL, LIPA, ALOX5, GPX1 and 1 morelysosome

• (12S)-hydroxy-(5Z,8Z,10E,14Z,17Z)-eicosapentaenoateReach from here →
  1. Steryl-ester acylhydrolase
  2. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + O2 = (12S)-hydroperoxy-(5Z,8Z,10E,14Z,17Z)-eicosapentaenoate
  3. (12S)-hydroperoxy-(5Z,8Z,10E,14Z,17Z)-eicosapentaenoate + 2 glutathione = (12S)-hydroxy-(5Z,8Z,10E,14Z,17Z)-eicosapentaenoate + glutathione disulfide + H2O

  Catalysed by CEL, LIPA, ALOX12, GPX1 and 1 morelysosome

• (5Z)-dodecenoyl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. acetyl-CoA C-acyltransferase (3-oxomyrist-7-enoyl-CoA)

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

• (11Z)-docosenoyl-CoA(4-)Reach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. long-chain-fatty-acid-CoA ligase (cis-cetoleic acid)

  Catalysed by CEL, LIPA, SOAT2, SOAT1 and 8 morelysosome, endoplasmic reticulum, cytosolOne of 5 routes

• (7Z)-tetradecenoyl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. long-chain-fatty-acid-CoA ligase ((7Z)-tetradecenoic acid)

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