cholesteryl (9Z-octadecenoate)

Three steps

• 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

• chlorine(.)Reach from here →
  1. Steryl-ester acylhydrolase
  2. Utilized Transport
  3. Carnitine Transport by Atb0

  Catalysed by CEL, LIPA, SLC6A14lysosome, endoplasmic reticulum, cytosol, extracellular space

• phosphocholineReach from here →
  1. cholesteryl (9Z-octadecenoate) + H2O = cholesterol + (9Z)-octadecenoate + H(+)
  2. 1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + cholesterol = cholesteryl (5Z,8Z,11Z,14Z)-eicosatetraenoate + 1-hexadecanoyl-sn-glycero-3-phosphocholine
  3. 1-hexadecanoyl-sn-glycero-3-phosphocholine + H2O = 1-hexadecanoyl-sn-glycerol + phosphocholine + H(+)

  Catalysed by CEL, CES1, LIPA, LIPE and 6 more

• 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

• a 1-O-alkyl-sn-glycero-3-phosphocholineReach from here →
  1. cholesteryl (9Z-octadecenoate) + H2O = cholesterol + (9Z)-octadecenoate + H(+)
  2. 1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + cholesterol = cholesteryl (5Z,8Z,11Z,14Z)-eicosatetraenoate + 1-hexadecanoyl-sn-glycero-3-phosphocholine
  3. a 1-O-alkyl-2-acetyl-sn-glycero-3-phosphocholine + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 1-hexadecanoyl-2-acetyl-sn-glycero-3-phosphocholine + a 1-O-alkyl-sn-glycero-3-phosphocholine

  Catalysed by CEL, CES1, LIPA, LIPE and 2 more

• 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 18 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 13 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 15 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

• 1-O-hexadecyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphocholineReach from here →
  1. Steryl-ester acylhydrolase
  2. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  3. 1-O-hexadecyl-sn-glycero-3-phosphocholine + (9Z)-octadecenoyl-CoA = 1-O-hexadecyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by CEL, LIPA, SLC27A2, ACSL3 and 7 morelysosome

• 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

• D-glucoseReach from here →
  1. cholesteryl (9Z-octadecenoate) + H2O = cholesterol + (9Z)-octadecenoate + H(+)
  2. a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + an N-acylsphing-4-enine
  3. cholesteryl 3-beta-D-glucoside + H2O = cholesterol + D-glucose

  Catalysed by CEL, CES1, LIPA, LIPE and 3 more

• 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

• 1,2-di-(9Z-octadecenoyl)-glycerolReach from here →
  1. Steryl-ester acylhydrolase
  2. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  3. 1-(9Z-octadecenoyl)-glycerol + (9Z)-octadecenoyl-CoA = 1,2-di-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by CEL, LIPA, SLC27A2, ACSL3 and 12 morelysosomeOne of 3 routes

• 1,2-di-(9Z-octadecenoyl)-sn-glycerolReach from here →
  1. Steryl-ester acylhydrolase
  2. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  3. 2-(9Z-octadecenoyl)-glycerol + (9Z)-octadecenoyl-CoA = 1,2-di-(9Z-octadecenoyl)-sn-glycerol + CoA

  Catalysed by CEL, LIPA, SLC27A2, ACSL3 and 9 morelysosomeOne of 2 routes

• a 1,2-diacyl-sn-glycero-3-phospho-L-serineReach from here →
  1. cholesteryl (9Z-octadecenoate) + H2O = cholesterol + (9Z)-octadecenoate + H(+)
  2. 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)
  3. a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol 4-phosphate)(out) + a 1,2-diacyl-sn-glycero-3-phospho-L-serine(in) = a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol 4-phosphate)(in) + a 1,2-diacyl-sn-glycero-3-phospho-L-serine(out)

  Catalysed by CEL, CES1, LIPA, LIPE and 8 moreinner side of the membrane, outer side of the membraneOne of 2 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 11 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 15 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 21 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 16 routes

• 7,8-dihydrofolateReach from here →
  1. cholesteryl (9Z-octadecenoate) + H2O = cholesterol + (9Z)-octadecenoate + H(+)
  2. cholesterol + AH2 + O2 = 25-hydroxycholesterol + 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, CES1, LIPA, LIPE and 3 more

• 1-hexadecanoyl-sn-glycero-3-phosphateReach from here →
  1. cholesteryl (9Z-octadecenoate) + H2O = cholesterol + (9Z)-octadecenoate + H(+)
  2. 1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + cholesterol = cholesteryl (5Z,8Z,11Z,14Z)-eicosatetraenoate + 1-hexadecanoyl-sn-glycero-3-phosphocholine
  3. 1-hexadecanoyl-sn-glycero-3-phosphocholine + H2O = 1-hexadecanoyl-sn-glycero-3-phosphate + choline + H(+)

  Catalysed by CEL, CES1, LIPA, LIPE and 5 more

• O-acetyl-(R)-carnitineReach from here →
  1. Steryl-ester acylhydrolase
  2. Utilized Transport
  3. Acetyl-CoA:carnitine O-acetyltransferase

  Catalysed by CEL, LIPA, CPT1A, CPT1C and 1 morelysosome, endoplasmic reticulum, cytosolOne of 9 routes

• a 1,2-diacyl-sn-glycero-3-phosphocholineReach from here →
  1. cholesteryl (9Z-octadecenoate) + H2O = cholesterol + (9Z)-octadecenoate + H(+)
  2. 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)
  3. a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol 4-phosphate)(out) + a 1,2-diacyl-sn-glycero-3-phosphocholine(in) = a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol 4-phosphate)(in) + a 1,2-diacyl-sn-glycero-3-phosphocholine(out)

  Catalysed by CEL, CES1, LIPA, LIPE and 3 moreinner side of the membrane, outer side of the membraneOne of 2 routes

• an N-acylsphing-4-enine 1-phosphateReach from here →
  1. cholesteryl (9Z-octadecenoate) + H2O = cholesterol + (9Z)-octadecenoate + H(+)
  2. a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + an N-acylsphing-4-enine
  3. an N-acylsphing-4-enine + ATP = an N-acylsphing-4-enine 1-phosphate + ADP + H(+)

  Catalysed by CEL, CES1, LIPA, LIPE and 5 more

• 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 16 routes

• a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol-5-phosphate)Reach from here →
  1. cholesteryl (9Z-octadecenoate) + H2O = cholesterol + (9Z)-octadecenoate + H(+)
  2. 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)
  3. a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol-4,5-bisphosphate) + H2O = a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol-5-phosphate) + phosphate

  Catalysed by CEL, CES1, LIPA, LIPE and 5 moreinner side of the membrane, outer side of the membrane

• 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

• a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol)Reach from here →
  1. cholesteryl (9Z-octadecenoate) + H2O = cholesterol + (9Z)-octadecenoate + H(+)
  2. 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)
  3. a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol 4-phosphate) + H2O = a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol) + phosphate

  Catalysed by CEL, CES1, LIPA, LIPE and 6 moreinner side of the membrane, outer side of the membrane