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

Three steps

• spermidineReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. diamine N-acetyltransferase (N1-acetylspermidine)

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

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

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

• L-alanineReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. amino-acid N-acetyltransferase (N-acetyl-L-alanine)

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

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

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

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

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

• a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol 4-phosphate)Reach 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 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)

  Catalysed by CES1, LIPN, NCEH1, LDAH and 1 moreendoplasmic reticulum, inner side of the membrane, outer side of the membraneOne of 2 routes

• glutathione disulfideReach 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 morelysosomeOne of 2 routes

• an acyl-CoAReach 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 3 routes

• a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol-4,5-bisphosphate)Reach 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 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)

  Catalysed by CES1, LIPN, NCEH1, LDAH and 2 moreendoplasmic reticulum, inner side of the membrane, outer side of the membraneOne of 2 routes

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

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

• (25R)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oyl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. 3alpha,7alpha,12alpha-trihydroxy-5beta-cholestanoate:CoA ligase (AMP-forming)

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

• deoxycholoyl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. cholate-CoA ligase (3alpha,12alpha-dihydroxy-5beta-cholanate)

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

• a 2,3-dehydroacyl-CoAReach 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 2,3-saturated acyl-CoA + A = a 2,3-dehydroacyl-CoA + AH2

  Catalysed by CEL, LIPA, PTGS2, ACAD10lysosome

• decanoyl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. medium-chain acyl-CoA ligase (decanoic acid)

  Catalysed by CEL, LIPA, SOAT2, SOAT1 and 6 morelysosome, endoplasmic reticulum, cytosolOne of 7 routes

• (2E)-hexadecenoyl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. Carnitine O-Palmitoyltransferase

  Catalysed by CEL, LIPA, SOAT2, SOAT1 and 3 morelysosome, endoplasmic reticulum, cytosolOne of 4 routes

• (9Z)-hexadecenoyl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. long-chain-fatty-acid-CoA ligase (palmitolate)

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

• Fe(II)-heme aReach 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. Fe(II)-heme o + 2 A + H2O = Fe(II)-heme a + 2 AH2

  Catalysed by CEL, LIPA, PTGS2, COX15lysosome

• 3-hydroxyisovaleryl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. (3-Hydroxyisovalerylcoa->3-Hydroxyisovalerylcarnitine)

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

• an all-trans-retinyl esterReach 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. an all-trans-retinyl ester + H2O = 11-cis-retinol + a fatty acid + H(+)

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

• CHEBI:63544Reach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. long-chain-fatty-acid-CoA ligase (adrenic acid)

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

• pregn-5-ene-3,20-dioneReach 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

• 4-methylpentan-1-olReach from here →
  1. Steryl-ester acylhydrolase
  2. cytochrome P450 (cholesterol)
  3. aldose reductase (isocaproic-aldehyde)

  Catalysed by CEL, LIPA, CYP11A1, AKR1B10 and 1 morelysosome, mitochondrial matrix, cytosolOne of 2 routes

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

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

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

  Catalysed by CEL, LIPA, SOAT2, SOAT1 and 8 morelysosome, endoplasmic reticulum, cytosolOne of 10 routes

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

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

• (22R)-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. 2 reduced [adrenodoxin] + cholesterol + O2 + 2 H(+) = (22R)-hydroxycholesterol + 2 oxidized [adrenodoxin] + H2O

  Catalysed by CES1, LIPN, NCEH1, LDAH and 1 moreendoplasmic reticulumOne of 2 routes

• Mo-molybdopterinReach 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. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O

  Catalysed by CEL, LIPA, PTGS2, MOCOSlysosome

• (2E)-octadecenoyl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. Carnitine O-Palmitoyltransferase

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

• (6Z,9Z,12Z,15Z)-octadecatetraenoyl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. long-chain-fatty-acid-CoA ligase (stearidonic acid)

  Catalysed by CEL, LIPA, SOAT2, SOAT1 and 8 morelysosome, endoplasmic reticulum, cytosolOne of 10 routes

• (8Z,11Z,14Z)-eicosatrienoateReach 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

• N-dodecanoylsphing-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. 1-(beta-D-galactosyl)-N-dodecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-galactoside + N-dodecanoylsphing-4-enine

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

• N-hexadecanoylsphing-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-(1<->1')-N-hexadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-hexadecanoylsphing-4-enine

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

• N-octadecanoylsphing-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-(1<->1)-N-octadecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + N-octadecanoylsphing-4-enine

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

• 1-hexadecanoyl-sn-glycero-3-phosphocholineReach from here →
  1. Steryl-ester acylhydrolase
  2. Cytochrome P450, Family 46, Subfamily A, Polypeptide 1
  3. a 1-hexadecanoyl-2-acyl-sn-glycero-3-phosphocholine + (24S)-hydroxycholesterol = (24S)-24-hydroxycholesterol ester + 1-hexadecanoyl-sn-glycero-3-phosphocholine

  Catalysed by CEL, LIPA, CYP46A1, LCATlysosome, endoplasmic reticulumOne of 11 routes

• 3-oxo-(7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. long-chain-fatty-acid-CoA ligase (EPA)
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA + malonyl-CoA + H(+) = 3-oxo-(7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl-CoA + CO2 + CoA

  Catalysed by CEL, LIPA, SLC27A2, ACSL4 and 8 morelysosome, cytosol

• (7Z,10Z,13Z,16Z,19Z)-docosapentaenoyl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. long-chain-fatty-acid-CoA ligase (DPA)

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

• (9Z,12Z,15Z)-octadecatrienoyl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. long-chain-fatty-acid-CoA ligase (linolenate)

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

• (13Z)-docosenoyl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. long-chain-fatty-acid-CoA ligase (cis-erucic acid)

  Catalysed by CEL, LIPA, SOAT2, SOAT1 and 8 morelysosome, endoplasmic reticulum, cytosolOne of 6 routes

• (11Z)-eicosenoyl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. long-chain-fatty-acid-CoA ligase (cis-gondoic acid)

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

• (9Z,12Z,15Z,18Z,21Z)-tetracosapentaenoyl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. long-chain-fatty-acid-CoA ligase ((9Z,12Z,15Z,18Z,21Z)-TPA)

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

• (6Z,9Z,12Z,15Z,18Z,21Z)-tetracosahexaenoyl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. long-chain-fatty-acid-CoA ligase ((6Z,9Z,12Z,15Z,18Z,21Z)-THA)

  Catalysed by CEL, LIPA, SOAT2, SOAT1 and 8 morelysosome, endoplasmic reticulum, cytosolOne of 4 routes

• (15Z)-tetracosenoyl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. long-chain-fatty-acid-CoA ligase (nervonic acid)

  Catalysed by CEL, LIPA, SOAT2, SOAT1 and 8 morelysosome, endoplasmic reticulum, cytosolOne of 6 routes

• (17Z)-hexacosenoyl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. long-chain-fatty-acid-CoA ligase (ximenic acid)

  Catalysed by CEL, LIPA, SOAT2, SOAT1 and 8 morelysosome, endoplasmic reticulum, cytosolOne of 4 routes

• (8Z,11Z,14Z)-eicosatrienoyl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)

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

• (8Z,11Z,14Z,17Z)-eicosatetraenoyl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. long-chain-fatty-acid-CoA ligase (omega-3-arachidonic acid)

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

• (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. long-chain-fatty-acid-CoA ligase (DHA)

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

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

  Catalysed by CEL, LIPA, SOAT2, SOAT1 and 8 morelysosome, endoplasmic reticulum, cytosolOne of 6 routes

• (9Z)-heptadecenoyl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. long-chain-fatty-acid-CoA ligase (9-heptadecylenic acid)

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

• (11Z,14Z,17Z)-eicosatrienoyl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. long-chain-fatty-acid-CoA ligase ((11Z,14Z,17Z)-eicosatrienoic acid)

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

• N-(15Z-tetracosenoyl)-sphing-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-(1<->1')-N-(15Z-tetracosenoyl)-sphing-4-enine + cholesterol = N-(15Z-tetracosenoyl)-sphing-4-enine + cholesteryl 3-beta-D-glucoside

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