cholesteryl (9Z-octadecenoate)

Three steps

• formaldehydeReach from here →
  1. cholesteryl (9Z-octadecenoate) + H2O = cholesterol + (9Z)-octadecenoate + H(+)
  2. cholesterol + AH2 + O2 = 25-hydroxycholesterol + 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, CES1, LIPA, LIPE and 4 moreOne 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, cytosolOne of 7 routes

• 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. cholesteryl (9Z-octadecenoate) + H2O = cholesterol + (9Z)-octadecenoate + H(+)
  2. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  3. all-trans-13,14-dihydroretinol + A = all-trans-retinol + AH2

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

• 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 16 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

• O-hexadecanoyl-(R)-carnitineReach from here →
  1. Steryl-ester acylhydrolase
  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. cholesteryl (9Z-octadecenoate) + H2O = cholesterol + (9Z)-octadecenoate + H(+)
  2. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  3. A + NADH + H(+) = AH2 + NAD(+)

  Catalysed by CEL, CES1, LIPA, LIPE and 4 moreOne 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

• a sphingomyelinReach 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. ceramide:phosphatidylcholine cholinephosphotransferase

  Catalysed by CEL, CES1, LIPA, LIPE and 5 moreGolgi apparatusOne of 8 routes

• (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

• a 1,2-diacyl-sn-glycerolReach 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. ceramide:phosphatidylcholine cholinephosphotransferase

  Catalysed by CEL, CES1, LIPA, LIPE and 5 moreGolgi apparatusOne of 9 routes

• 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

• O-octanoyl-(R)-carnitineReach from here →
  1. Steryl-ester acylhydrolase
  2. Utilized Transport
  3. solute carrier (L-carnitine)

  Catalysed by CEL, LIPA, SLC25A20lysosome, endoplasmic reticulum, cytosol, mitochondrial matrixOne of 7 routes

• 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 14 routes

• D-glucosyl-N-acylsphingosineReach 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. UDP-glucose:N-acylsphingosine D-glucosyltransferase

  Catalysed by CEL, CES1, LIPA, LIPE and 4 morecytosolOne of 2 routes

• a beta-D-galactosyl-(1<->1')-N-acylsphing-4-enineReach 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 + UDP-alpha-D-galactose = a beta-D-galactosyl-(1<->1')-N-acylsphing-4-enine + UDP + H(+)

  Catalysed by CEL, CES1, LIPA, LIPE and 4 moreOne of 3 routes

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

  Catalysed by CEL, CES1, LIPA, LIPE and 4 moreOne of 3 routes

• beta-D-xylosyl-(1<->1')-N-(9Z-octadecenoyl)-sphing-4-enineReach from here →
  1. Steryl-ester acylhydrolase
  2. N-(9Z-octadecenoyl)-sphing-4-enine + H2O = sphing-4-enine + (9Z)-octadecenoate
  3. N-(9Z-octadecenoyl)-sphing-4-enine + UDP-alpha-D-xylose = beta-D-xylosyl-(1<->1')-N-(9Z-octadecenoyl)-sphing-4-enine + UDP + H(+)

  Catalysed by CEL, LIPA, ASAH1, ACER2 and 4 morelysosome

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

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

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

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

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

  Catalysed by CEL, LIPA, SLC27A2, ACSL3 and 8 morelysosome

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

  Catalysed by CEL, LIPA, SLC27A2, ACSL3 and 8 morelysosome

• 1-(9Z,12Z,15Z-octadecatrienoyl)-3-(9Z-octadecenoyl)-glycerolReach from here →
  1. Steryl-ester acylhydrolase
  2. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  3. 1-(9Z,12Z,15Z-octadecatrienoyl)-glycerol + (9Z)-octadecenoyl-CoA = 1-(9Z,12Z,15Z-octadecatrienoyl)-3-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by CEL, LIPA, SLC27A2, ACSL3 and 8 morelysosome

• 1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-3-(9Z-octadecenoyl)-glycerolReach from here →
  1. Steryl-ester acylhydrolase
  2. (9Z)-octadecenoate + ATP + CoA = (9Z)-octadecenoyl-CoA + AMP + diphosphate
  3. 1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol + (9Z)-octadecenoyl-CoA = 1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-3-(9Z-octadecenoyl)-glycerol + CoA

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

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

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

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

  Catalysed by CEL, LIPA, SLC27A2, ACSL3 and 12 morelysosome

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

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

• 1D-myo-inositol 1,4,5-trisphosphateReach 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 = 1D-myo-inositol 1,4,5-trisphosphate + a 1,2-diacyl-sn-glycerol + H(+)

  Catalysed by CEL, CES1, LIPA, LIPE and 16 moreinner side of the membrane, outer side of the membrane

• a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enineReach 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. a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + an N-acylsphing-4-enine

  Catalysed by CEL, CES1, LIPA, LIPE and 3 moreOne of 3 routes

• (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

• 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(3'-(9Z-octadecenoyl)-1'-sn-glycerol)Reach from here →
  1. Steryl-ester acylhydrolase
  2. 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol) + H2O = sn-glycero-3-phospho-(1'-sn-glycerol) + (9Z)-octadecenoate + H(+)
  3. 2 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol) = 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-(3'-(9Z-octadecenoyl)-1'-sn-glycerol) + sn-glycero-3-phospho-(1'-sn-glycerol)

  Catalysed by CEL, LIPA, ABHD12, CLN5lysosome

• (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

• (4Z,7Z,10Z,13Z)-hexadecatetraenoyl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. Fatty Acid Beta Oxidation (C18:4->C16:4), Mitochondrial

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

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

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

• (4Z,7Z)-decadienoyl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. Fatty Acid Beta Oxidation (C12:3->C10:2), Mitochondrial

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

• (5Z)-octenoyl-CoAReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. Fatty Acid Beta Oxidation (C10:2->C8:1), Mitochondrial

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

• docosanoateReach 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

• octadecanoateReach 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 15 routes

• octanoateReach from here →
  1. cholesteryl (9Z-octadecenoate) + H2O = cholesterol + (9Z)-octadecenoate + H(+)
  2. beta-D-glucosyl-N-octanoylsphing-4E-enine + cholesterol = N-octanoylsphing-4-enine + cholesteryl 3-beta-D-glucoside
  3. N-octanoylsphing-4-enine + H2O = octanoate + sphing-4-enine

  Catalysed by CEL, CES1, LIPA, LIPE and 4 more

• alpha-linolenic acidReach 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

• CHEBI:27540Reach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. medium-chain acyl-CoA ligase (hexanoic acid)

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

• 7-dehydrodesmosterolReach from here →
  1. Steryl-ester acylhydrolase
  2. 3-hydroxyacyl-CoA dehydrogenase (desmosterol)
  3. 7-Dehydrocholesterol Reductase

  Catalysed by CEL, LIPA, DHCR7lysosome, nucleus

• elaidic acidReach from here →
  1. Steryl-ester acylhydrolase
  2. Sterol O-Acyltransferase
  3. long-chain-fatty-acid-CoA ligase (elaidate)

  Catalysed by CEL, LIPA, SOAT2, SOAT1 and 8 morelysosome, endoplasmic reticulum, cytosolOne of 18 routes

• all-cis-docosa-4,7,10,13,16,19-hexaenoic acidReach 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-(9Z-octadecenoyl)-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. 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + 1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine

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