cholesteryl (5Z,8Z,11Z,14Z)-eicosatetraenoate

Three steps

• (24S)-hydroxycholesterol 3-sulfateReach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  2. Cytochrome P450, Family 46, Subfamily A, Polypeptide 1
  3. (24S)-hydroxycholesterol + 3'-phosphoadenylyl sulfate = (24S)-hydroxycholesterol 3-sulfate + adenosine 3',5'-bisphosphate + H(+)

  Catalysed by CEL, LIPA, CYP46A1, SULT2B1 and 2 morelysosome, endoplasmic reticulum

• 2-[15(S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoyl]-glycerolReach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  2. fatty acid amide hydrolase (2-arachidonoylglycerol)
  3. 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + O2 = 2-[15(S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoyl]-glycerol

  Catalysed by CEL, LIPA, FAAH, ALOX15Blysosome, cytosol

• (13S)-hydroxy-(14S,15S)-epoxy-(5Z,8Z,11Z)-eicosatrienoateReach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate
  3. (15S)-hydroperoxy-(5Z,8Z,11Z,13E)-eicosatetraenoate = (13S)-hydroxy-(14S,15S)-epoxy-(5Z,8Z,11Z)-eicosatrienoate

  Catalysed by CEL, LIPA, ALOX15B, ALOX15 and 2 morelysosome

• (5S,15S)-dihydroperoxy-(6E,8Z,11Z,13E)-eicosatetraenoateReach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (5S)-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate
  3. (5S)-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate + O2 = (5S,15S)-dihydroperoxy-(6E,8Z,11Z,13E)-eicosatetraenoate

  Catalysed by CEL, LIPA, ALOX5, ALOX15Blysosome

• 2-[12-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoyl]-glycerolReach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  2. fatty acid amide hydrolase (2-arachidonoylglycerol)
  3. 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + O2 = 2-[12-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoyl]-glycerol

  Catalysed by CEL, LIPA, FAAH, ALOX15Blysosome, cytosol

• 1-(10Z-heptadecenoyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamineReach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + ATP + CoA = (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + AMP + diphosphate
  3. 1-(10Z-heptadecenoyl)-sn-glycero-3-phosphoethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-(10Z-heptadecenoyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine + CoA

  Catalysed by CEL, LIPA, SLC27A2, ACSL4 and 10 morelysosome

• (7Z)-octadecenoyl-CoAReach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  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

• (15S)-15-hydroperoxy-prostaglandin E2Reach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  2. Arachidonate:oxygen oxidoreductase
  3. prostaglandin G2 = (15S)-15-hydroperoxy-prostaglandin E2

  Catalysed by CEL, LIPA, PTGS1, PTGS2 and 1 morelysosome, endoplasmic reticulum

• CHEBI:15345Reach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  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. sterol esterase (Cholesteryl Arachidonate)
  2. Sterol O-Acyltransferase
  3. Acetyl-CoA:choline O-acetyltransferase

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

• acetylcholineReach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  2. transport of arachidonate (cytosol to extracellular)
  3. transport of acetylcholine (cytosol to extracellular)

  Catalysed by CEL, LIPA, SLCO1B1, SLCO1B3lysosome, extracellular space, cytosolOne of 4 routes

• CHEBI:15380Reach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  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. sterol esterase (Cholesteryl Arachidonate)
  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. sterol esterase (Cholesteryl Arachidonate)
  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. sterol esterase (Cholesteryl Arachidonate)
  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. sterol esterase (Cholesteryl Arachidonate)
  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. sterol esterase (Cholesteryl Arachidonate)
  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

• CHEBI:15519Reach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  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. sterol esterase (Cholesteryl Arachidonate)
  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. sterol esterase (Cholesteryl Arachidonate)
  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. sterol esterase (Cholesteryl Arachidonate)
  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. sterol esterase (Cholesteryl Arachidonate)
  2. Utilized Transport
  3. Active Transport

  Catalysed by CEL, LIPAlysosome, endoplasmic reticulum, cytosol, mitochondrial matrixOne of 45 routes

• CHEBI:15650Reach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  2. transport of arachidonate (cytosol to extracellular)
  3. transport of leukotriene E4 (cytosol to extracellular)

  Catalysed by CEL, LIPA, SLCO1B1lysosome, extracellular space, cytosolOne of 6 routes

• S-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-4'-phosphopantetheineReach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + ATP + CoA = (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + AMP + diphosphate
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + H2O = S-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-4'-phosphopantetheine + adenosine 3',5'-bisphosphate + 2 H(+)

  Catalysed by CEL, LIPA, SLC27A2, ACSL4 and 10 morelysosome

• betaine aldehydeReach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
  3. choline + A = betaine aldehyde + AH2

  Catalysed by CEL, LIPA, PTGS1, PTGS2 and 1 morelysosome

• CHEBI:15727Reach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  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. sterol esterase (Cholesteryl Arachidonate)
  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. sterol esterase (Cholesteryl Arachidonate)
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by CEL, LIPAlysosome, cytosol, extracellular spaceOne of 16 routes

• bromideReach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. 2-bromoacetaldehyde:glutathione S-(formylmethyl)transferase

  Catalysed by CEL, LIPA, MGST3, GSTA4 and 15 morelysosome, extracellular space, cytosolOne of 2 routes

• 1,2-diacyl-sn-glycero-3-phosphocholine(1+)Reach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  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

• cholesterolReach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  2. Phosphatidylcholine:sterol O-acyltransferase
  3. a cholesterol ester + H2O = cholesterol + a fatty acid + H(+)

  Catalysed by CEL, LIPA, LCAT, CES1 and 3 morelysosome, cytosolOne of 3 routes

• sulfateReach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  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. sterol esterase (Cholesteryl Arachidonate)
  2. Sterol O-Acyltransferase
  3. Palmitoyl-CoA:retinol O-acyltransferase

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

• lithocholic acidReach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  2. transport of arachidonate (cytosol to extracellular)
  3. transport of lithocholate (cytosol to extracellular)

  Catalysed by CEL, LIPA, SLCO1B1, SLCO1A2 and 1 morelysosome, extracellular space, cytosolOne of 4 routes

• oxaloacetateReach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
  3. (R)-malate + A = oxaloacetate + AH2

  Catalysed by CEL, LIPA, PTGS1, PTGS2 and 1 morelysosomeOne of 2 routes

• (S)-lactateReach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  2. prostaglandin-endoperoxide synthase (arachidonate)
  3. prostaglandin H2(out) + 2 (S)-lactate(in) = prostaglandin H2(in) + 2 (S)-lactate(out)

  Catalysed by CEL, LIPA, PTGS1, PTGS2 and 1 morelysosome, cytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• formaldehydeReach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + 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, PTGS1, PTGS2 and 2 morelysosomeOne of 3 routes

• sn-glycerol 3-phosphocholineReach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  2. Phosphatidylcholine:sterol O-acyltransferase
  3. 1-Acyl-sn-glycero-3-phosphocholine acylhydrolase

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

• bilirubin IXalphaReach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  2. transport of arachidonate (cytosol to extracellular)
  3. transport of bilirubin (cytosol to extracellular)

  Catalysed by CEL, LIPA, SLCO1B1, SLCO1A2 and 1 morelysosome, extracellular space, cytosolOne of 4 routes

• progesteroneReach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  2. cytochrome P450 (cholesterol)
  3. Pregnenolone:NAD+ 3-oxidoreductase

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

• taurolithocholateReach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  2. transport of arachidonate (cytosol to extracellular)
  3. transport of S-glutathionyl-2-4-dinitrobenzene (cytosol to extracellular)

  Catalysed by CEL, LIPA, SLCO1B1, SLCO1A2 and 1 morelysosome, extracellular space, cytosolOne of 4 routes

• CHEBI:17208Reach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. glutathione:dehydroascorbate oxidoreductase

  Catalysed by CEL, LIPAlysosome, extracellular space, cytosol

• homocysteineReach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. Formation of Homocystine

  Catalysed by CEL, LIPAlysosome, extracellular space, cytosol

• anilineReach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  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. sterol esterase (Cholesteryl Arachidonate)
  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. sterol esterase (Cholesteryl Arachidonate)
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
  3. all-trans-13,14-dihydroretinol + A = all-trans-retinol + AH2

  Catalysed by CEL, LIPA, PTGS1, PTGS2 and 1 morelysosome

• linoleic acidReach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by CEL, LIPAlysosome, cytosol, extracellular spaceOne of 16 routes

• O-hexadecanoyl-(R)-carnitineReach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  2. Utilized Transport
  3. palmitoyl-CoA:L-carnitine O-palmitoyltransferase

  Catalysed by CEL, LIPA, CPT2, CPT1Alysosome, endoplasmic reticulum, cytosol, peroxisomeOne of 10 routes

• AH2Reach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + 2 O2 = prostaglandin H2 + A + H2O
  3. A + NADH + H(+) = AH2 + NAD(+)

  Catalysed by CEL, LIPA, PTGS1, PTGS2 and 2 morelysosomeOne of 19 routes

• L-cysteineReach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  2. transport of arachidonate and GSH (cytosol to extracellular)
  3. cystine to cysteine conversion

  Catalysed by CEL, LIPAlysosome, extracellular space, cytosolOne of 3 routes