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

Three steps

• (24S)-24-hydroxycholesterol esterReach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  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 reticulum

• (24S)-hydroxycholesterol 3-linoleoateReach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  2. Cytochrome P450, Family 46, Subfamily A, Polypeptide 1
  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 CEL, LIPA, CYP46A1, LCATlysosome, endoplasmic reticulum

• 1-heptadecanoyl-sn-glycero-3-phosphoserineReach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  2. 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoserine + H2O = 1-heptadecanoyl-sn-glycero-3-phosphoserine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)
  3. 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoserine + H2O = 1-heptadecanoyl-sn-glycero-3-phosphoserine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)

  Catalysed by CEL, LIPA, ABHD16Alysosome

• 1-heptadecanoyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  2. 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine + H2O = 1-heptadecanoyl-sn-glycero-3-phosphoethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)
  3. 1-heptadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphoethanolamine + H2O = 1-heptadecanoyl-sn-glycero-3-phosphoethanolamine + (5Z,8Z,11Z,14Z)-eicosatetraenoate + H(+)

  Catalysed by CEL, LIPA, ABHD16Alysosome

• (5Z)-tetradecenoyl-CoAReach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  2. Sterol O-Acyltransferase
  3. long-chain-fatty-acid-CoA ligase (physeteric acid)

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

• O-4,8-dimethylnonanoyl-(R)-carnitineReach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  2. Utilized Transport
  3. Carnitine Dimethyl Nonanoyl Transferase, Revsible, Peroxisomal

  Catalysed by CEL, LIPA, CRAT, CROTlysosome, endoplasmic reticulum, cytosol, peroxisomeOne of 5 routes

• (3E)-decenoyl-CoAReach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  2. Sterol O-Acyltransferase
  3. Fatty Acid Beta Oxidation (C12:1->C10:1), Mitochondrial

  Catalysed by CEL, LIPA, SOAT2, SOAT1 and 4 morelysosome, endoplasmic reticulum, mitochondrial matrix

• 2-glyceryl-prostaglandin G2Reach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  2. fatty acid amide hydrolase (2-arachidonoylglycerol)
  3. 2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + 2 O2 = 2-glyceryl-prostaglandin G2

  Catalysed by CEL, LIPA, FAAH, PTGS2lysosome, cytosol

• 1-O-(9Z-octadecenyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphateReach 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-O-(9Z-octadecenyl)-sn-glycero-3-phosphate + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-O-(9Z-octadecenyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphate + CoA

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

• 24S,25-dihydroxycholesterolReach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  2. Cytochrome P450, Family 46, Subfamily A, Polypeptide 1
  3. (24S)-hydroxycholesterol + reduced [NADPH--hemoprotein reductase] + O2 = 24S,25-dihydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CEL, LIPA, CYP46A1lysosome, endoplasmic reticulum

• (24S,25R)-24,26-dihydroxycholesterolReach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  2. Cytochrome P450, Family 46, Subfamily A, Polypeptide 1
  3. (24S)-hydroxycholesterol + reduced [NADPH--hemoprotein reductase] + O2 = (24S,25R)-24,26-dihydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CEL, LIPA, CYP46A1lysosome, endoplasmic reticulum

• (2R,6)-dimethylheptanoyl-CoAReach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  2. Sterol O-Acyltransferase
  3. acetyl-CoA C-acyltransferase (3-oxo-4(R),8-dimethyl-nonanoyl-CoA)

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

• (7Z)-hexadecenoyl-CoAReach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  2. Sterol O-Acyltransferase
  3. long-chain-fatty-acid-CoA ligase (7-palmitoleic acid)

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

• tricosanoyl-CoAReach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  2. Sterol O-Acyltransferase
  3. long-chain-fatty-acid-CoA ligase (tricosanoic acid)

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

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

  Catalysed by CEL, LIPA, ALOX5, PTGES and 5 morelysosome

• (12S)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoateReach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 = (12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate
  3. (12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoate + 2 glutathione = (12S)-hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoate + glutathione disulfide + H2O

  Catalysed by CEL, LIPA, ALOX5, ALOX15 and 3 morelysosome

• (12S)-hydroxy-(5Z,8E,10E)-heptadecatrienoateReach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  2. prostaglandin-endoperoxide synthase (arachidonate)
  3. prostaglandin H2 = (12S)-hydroxy-(5Z,8E,10E)-heptadecatrienoate + malonaldehyde

  Catalysed by CEL, LIPA, PTGS1, PTGS2 and 3 morelysosome, cytosol

• thromboxane B2Reach 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, SLCO1B1lysosome, extracellular space, cytosolOne of 4 routes

• 11-oxo-(5Z,8Z,12E,14Z)-eicosatetraenoateReach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  2. (5Z,8Z,11Z,14Z)-eicosatetraenoate + AH2 + O2 = (11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoate + A + H2O
  3. (11R)-hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoate + NAD(+) = 11-oxo-(5Z,8Z,12E,14Z)-eicosatetraenoate + NADH + H(+)

  Catalysed by CEL, LIPA, PTGS2, HPGDlysosome

• 19-hydroxyprostaglandin H2Reach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  2. prostaglandin-endoperoxide synthase (arachidonate)
  3. prostaglandin H2 + reduced [NADPH--hemoprotein reductase] + O2 = 19-hydroxyprostaglandin H2 + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

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

• taurochenodeoxycholateReach from here →
  1. sterol esterase (Cholesteryl Arachidonate)
  2. transport of arachidonate (cytosol to extracellular)
  3. solute carrier organic anion transporter (S-glutathionyl-2-4-dinitrobenzene)

  Catalysed by CEL, LIPA, SLCO1B1, SLCO1A2 and 2 morelysosome, extracellular space, cytosolOne of 4 routes