CHEBI:1307929

Three steps

• glycolithocholic acidReach from here →
  1. Sterol O-Acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. bile acid-CoA:amino acid N-acyltransferase (glycine)

  Catalysed by SOAT2, SOAT1, GLYAT, GLYATL2 and 2 moreendoplasmic reticulum, mitochondrial matrix, cytosolOne of 2 routes

• L-2-amino-3-oxobutanoic acidReach from here →
  1. Sterol O-Acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. Acetyl-CoA:glycine C-acetyltransferase

  Catalysed by SOAT2, SOAT1, GLYAT, GLYATL2 and 2 moreendoplasmic reticulum, mitochondrial matrix

• (3S)-3-hydroxy-3-methylglutaryl-CoAReach from here →
  1. Sterol O-Acyltransferase
  2. Production of Glutaryl Carnitine
  3. 3-hydroxy-3-methylglutarate + glutaryl-CoA = (3S)-3-hydroxy-3-methylglutaryl-CoA + glutarate

  Catalysed by SOAT2, SOAT1, CPT1A, CPT1C and 2 moreendoplasmic reticulum, cytosol

• phosphoenolpyruvic acidReach from here →
  1. Sterol O-Acyltransferase
  2. ATP citrate lyase (citrate)
  3. GTP:oxaloacetate carboxy-lyase (adding GTP

  Catalysed by SOAT2, SOAT1, ACLY, PCK1endoplasmic reticulum, cytosolOne of 2 routes

• 13-cis-retinolReach from here →
  1. Sterol O-Acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. 11-cis-retinol = 13-cis-retinol

  Catalysed by SOAT2, SOAT1, DGAT1, LRAT and 4 moreendoplasmic reticulum, cytosol

• spermineReach from here →
  1. Sterol O-Acyltransferase
  2. diamine N-acetyltransferase (N1-acetylspermidine)
  3. S-adenosyl 3-(methylsulfanyl)propylamine + spermidine = spermine + S-methyl-5'-thioadenosine + H(+)

  Catalysed by SOAT2, SOAT1, SAT1, SAT2 and 1 moreendoplasmic reticulum, cytosolOne of 2 routes

• N-octanoylsphing-4-enineReach from here →
  1. Phosphatidylcholine:sterol O-acyltransferase
  2. a cholesterol ester + H2O = cholesterol + a fatty acid + H(+)
  3. beta-D-glucosyl-N-octanoylsphing-4E-enine + cholesterol = N-octanoylsphing-4-enine + cholesteryl 3-beta-D-glucoside

  Catalysed by LCAT, CES1, LIPN, NCEH1 and 2 morecytosol

• L-ornithineReach from here →
  1. Sterol O-Acyltransferase
  2. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)
  3. taurine + L-arginine = taurocyamine + L-ornithine

  Catalysed by SOAT2, SOAT1, BAAT, GATMendoplasmic reticulum, cytosolOne of 15 routes

• N-(acetyl)-sphing-4-enineReach from here →
  1. Sterol O-Acyltransferase
  2. acyl-CoA:sphingosine N-acyltransferase
  3. 1-O-hexadecyl-2-acetyl-sn-glycero-3-phosphocholine + sphing-4-enine = 1-O-hexadecyl-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine + H(+)

  Catalysed by SOAT2, SOAT1, ASAH1, ACER2 and 3 moreendoplasmic reticulum, Golgi apparatusOne of 2 routes

• a 1,3-diacylglycerolReach from here →
  1. Sterol O-Acyltransferase
  2. acyl-CoA:sphingosine N-acyltransferase
  3. a 1-acylglycerol + an acyl-CoA = a 1,3-diacylglycerol + CoA

  Catalysed by SOAT2, SOAT1, ASAH1, ACER2 and 4 moreendoplasmic reticulum, Golgi apparatus

• a 1,2-diacylglycerolReach from here →
  1. Sterol O-Acyltransferase
  2. acyl-CoA:sphingosine N-acyltransferase
  3. a 2-acylglycerol + an acyl-CoA = a 1,2-diacylglycerol + CoA

  Catalysed by SOAT2, SOAT1, ASAH1, ACER2 and 7 moreendoplasmic reticulum, Golgi apparatusOne of 2 routes

• (24R)-hydroxycholesterolReach from here →
  1. Phosphatidylcholine:sterol O-acyltransferase
  2. a cholesterol ester + H2O = cholesterol + a fatty acid + H(+)
  3. cholesterol + reduced [NADPH--hemoprotein reductase] + O2 = (24R)-hydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by LCAT, CES1, LIPN, NCEH1 and 2 morecytosol

• gamma-Glu-AlaReach from here →
  1. Sterol O-Acyltransferase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. gamma-glutamyltransferase (alanine)

  Catalysed by SOAT2, SOAT1, GGT1, GGT5 and 4 moreendoplasmic reticulum, mitochondrial matrix, extracellular space, cytosol

• S(8)-aminomethyldihydrolipoamideReach from here →
  1. Sterol O-Acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. dihydrolipoyl dehydrogenase ([protein]-N6-(lipoyl)lysine)

  Catalysed by SOAT2, SOAT1, GLYAT, GLYATL2 and 3 moreendoplasmic reticulum, mitochondrial matrix

• an N-acylsphing-4-enineReach from here →
  1. Phosphatidylcholine:sterol O-acyltransferase
  2. a cholesterol ester + H2O = cholesterol + a fatty acid + H(+)
  3. a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + an N-acylsphing-4-enine

  Catalysed by LCAT, CES1, LIPN, NCEH1 and 3 morecytosolOne of 4 routes

• N-tetracosanoylsphinganineReach from here →
  1. Sterol O-Acyltransferase
  2. long-chain-fatty-acid-CoA ligase (lignocerate)
  3. tetracosanoyl-CoA + sphinganine = N-tetracosanoylsphinganine + CoA + H(+)

  Catalysed by SOAT2, SOAT1, SLC27A2, ACSL4 and 9 moreendoplasmic reticulum, cytosol

• N-hexacosanoylsphinganineReach from here →
  1. Sterol O-Acyltransferase
  2. long-chain-fatty-acid-CoA ligase (cerotic acid)
  3. hexacosanoyl-CoA + sphinganine = N-hexacosanoylsphinganine + CoA + H(+)

  Catalysed by SOAT2, SOAT1, SLC27A2, ACSL4 and 9 moreendoplasmic reticulum, cytosol

• 1,2,3-tri-(9Z-octadecenoyl)-glycerolReach from here →
  1. Acyl-CoA:cholesterol O-acyltransferase
  2. Steryl-ester acylhydrolase
  3. 1,2-di-(9Z-octadecenoyl)-glycerol + (9Z)-octadecenoate + H(+) = 1,2,3-tri-(9Z-octadecenoyl)-glycerol + H2O

  Catalysed by SOAT2, SOAT1, CEL, LIPA and 4 moreendoplasmic reticulum, lysosome

• 16-hydroxyhexadecanoateReach from here →
  1. Acyl-CoA:cholesterol O-acyltransferase
  2. Steryl-ester acylhydrolase
  3. Fatty Acid Omega Oxidation (C16->W-Ohc16), Endoplasmatic Reticulum

  Catalysed by SOAT2, SOAT1, CEL, LIPA and 2 moreendoplasmic reticulum, lysosomeOne of 2 routes

• a 1,2-diacyl-sn-glycero-3-phospho-L-serineReach from here →
  1. Sterol O-Acyltransferase
  2. acyl-CoA:sphingosine N-acyltransferase
  3. a 1-acyl-sn-glycero-3-phospho-L-serine + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phospho-L-serine + CoA

  Catalysed by SOAT2, SOAT1, ASAH1, ACER2 and 5 moreendoplasmic reticulum, Golgi apparatus

• succinyl-CoAReach from here →
  1. Sterol O-Acyltransferase
  2. aldehyde dehydrogenase (2-methyl-3-oxopropanoate)
  3. (R)-methylmalonyl-CoA = succinyl-CoA

  Catalysed by SOAT2, SOAT1, ALDH6A1, MMUTendoplasmic reticulum, mitochondrial matrixOne of 3 routes

• (2E)-butenoyl-CoAReach from here →
  1. Sterol O-Acyltransferase
  2. Butanoate:CoA ligase (AMP-forming)
  3. butanoyl-CoA:electron-transfer flavoprotein 2,3-oxidoreductase

  Catalysed by SOAT2, SOAT1, ACSM4, ACSM1 and 6 moreendoplasmic reticulum, cytosol, mitochondrial matrixOne of 4 routes

• 3-methyl-(2E)-glutaconyl-CoAReach from here →
  1. Sterol O-Acyltransferase
  2. glycine-N-acyltransferase (3-methylcrotonoylglycine)
  3. 3-Methylcrotonoyl-CoA:carbon-dioxide ligase (ADP-forming)

  Catalysed by SOAT2, SOAT1, GLYAT, MCCC1 and 1 moreendoplasmic reticulum, mitochondrial matrixOne of 2 routes

• 3-oxohexadecanoyl-CoAReach from here →
  1. Sterol O-Acyltransferase
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. tetradecanoyl-CoA + malonyl-CoA + H(+) = 3-oxohexadecanoyl-CoA + CO2 + CoA

  Catalysed by SOAT2, SOAT1, SLC27A2, ACSL4 and 8 moreendoplasmic reticulum, cytosol

• (2E)-glutaconyl-CoAReach from here →
  1. Sterol O-Acyltransferase
  2. Production of Glutaryl Carnitine
  3. glutaryl-CoA + O2 = (2E)-glutaconyl-CoA + H2O2

  Catalysed by SOAT2, SOAT1, CPT1A, CPT1C and 2 moreendoplasmic reticulum, cytosol

• acryloyl-CoAReach from here →
  1. Sterol O-Acyltransferase
  2. Propanoate:CoA ligase (AMP-forming)
  3. medium-chain acyl-CoA dehydrogenase (propanoyl-CoA)

  Catalysed by SOAT2, SOAT1, ACSS3, ACSS2 and 3 moreendoplasmic reticulum, cytosol, mitochondrial matrix

• (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoAReach from here →
  1. Sterol O-Acyltransferase
  2. long-chain-fatty-acid-CoA ligase (dihomo-gamma-linolenate)
  3. (8Z,11Z,14Z)-eicosatrienoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O

  Catalysed by SOAT2, SOAT1, SLC27A2, ACSL4 and 7 moreendoplasmic reticulum, cytosol

• hexadecanoyl-CoAReach from here →
  1. Sterol O-Acyltransferase
  2. Carnitine O-Palmitoyltransferase
  3. (2E)-hexadecenoyl-CoA + NADPH + H(+) = hexadecanoyl-CoA + NADP(+)

  Catalysed by SOAT2, SOAT1, CPT1A, CPT1C and 2 moreendoplasmic reticulum, cytosolOne of 2 routes

• (9Z)-octadecenoyl-CoAReach from here →
  1. Sterol O-Acyltransferase
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. octadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-octadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O

  Catalysed by SOAT2, SOAT1, SLC27A2, ACSL4 and 7 moreendoplasmic reticulum, cytosolOne of 2 routes

• propanoyl-CoAReach from here →
  1. Sterol O-Acyltransferase
  2. (S)-methylmalonyl-CoA hydrolase
  3. (S)-methylmalonyl-CoA + H(+) = propanoyl-CoA + CO2

  Catalysed by SOAT2, SOAT1, ECHDC1endoplasmic reticulum, mitochondrial matrix

• D-alanineReach from here →
  1. Sterol O-Acyltransferase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. D-alanine(out) + L-alanine(in) = D-alanine(in) + L-alanine(out)

  Catalysed by SOAT2, SOAT1, SLC7A10endoplasmic reticulum, mitochondrial matrix, inner side of the membrane, outer side of the membraneOne of 2 routes

• sarcosineReach from here →
  1. Sterol O-Acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. sarcosine + O2 + H2O = formaldehyde + glycine + H2O2

  Catalysed by SOAT2, SOAT1, GLYAT, GLYATL2 and 2 moreendoplasmic reticulum, mitochondrial matrixOne of 2 routes

• S-adenosyl 3-(methylsulfanyl)propylamineReach from here →
  1. Sterol O-Acyltransferase
  2. diamine N-acetyltransferase (N1-acetylspermidine)
  3. S-adenosyl 3-(methylsulfanyl)propylamine + putrescine = S-methyl-5'-thioadenosine + spermidine + H(+)

  Catalysed by SOAT2, SOAT1, SAT1, SAT2 and 1 moreendoplasmic reticulum, cytosol

• 7,8-dihydrofolateReach from here →
  1. Sterol O-Acyltransferase
  2. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)
  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 SOAT2, SOAT1, BAAT, MTO1endoplasmic reticulum, cytosol

• (6S)-5,6,7,8-tetrahydrofolateReach from here →
  1. Sterol O-Acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. (6R)-5,10-methylene-5,6,7,8-tetrahydrofolate + glycine + H2O = (6S)-5,6,7,8-tetrahydrofolate + L-serine

  Catalysed by SOAT2, SOAT1, GLYAT, GLYATL2 and 3 moreendoplasmic reticulum, mitochondrial matrix

• (13S)-hydroperoxy-(9Z,11E)-octadecadienoateReach from here →
  1. Acyl-CoA:cholesterol O-acyltransferase
  2. Steryl-ester acylhydrolase
  3. Linoleate:oxygen 13-oxidoreductase

  Catalysed by SOAT2, SOAT1, CEL, LIPA and 2 moreendoplasmic reticulum, lysosome, cytosol

• propane-1,3-diamineReach from here →
  1. Sterol O-Acyltransferase
  2. diamine N-acetyltransferase (N1-acetylspermidine)
  3. [eIF5A protein]-L-lysine + spermidine = [eIF5A protein]-deoxyhypusine + propane-1,3-diamine

  Catalysed by SOAT2, SOAT1, SAT1, SAT2 and 1 moreendoplasmic reticulum, cytosol

• 1-hexadecanoyl-sn-glycero-3-phosphateReach from here →
  1. Cytochrome P450, Family 46, Subfamily A, Polypeptide 1
  2. a 1-hexadecanoyl-2-acyl-sn-glycero-3-phosphocholine + (24S)-hydroxycholesterol = (24S)-24-hydroxycholesterol ester + 1-hexadecanoyl-sn-glycero-3-phosphocholine
  3. 1-hexadecanoyl-sn-glycero-3-phosphocholine + H2O = 1-hexadecanoyl-sn-glycero-3-phosphate + choline + H(+)

  Catalysed by CYP46A1, LCAT, ENPP2, GDPD3 and 1 moreendoplasmic reticulumOne of 2 routes

• a 1-acylglycerone 3-phosphateReach from here →
  1. Sterol O-Acyltransferase
  2. acyl-CoA:sphingosine N-acyltransferase
  3. dihydroxyacetone phosphate + an acyl-CoA = a 1-acylglycerone 3-phosphate + CoA

  Catalysed by SOAT2, SOAT1, ASAH1, ACER2 and 3 moreendoplasmic reticulum, Golgi apparatus

• (R)-2-hydroxyoctadecanoateReach from here →
  1. Acyl-CoA:cholesterol O-acyltransferase
  2. Steryl-ester acylhydrolase
  3. octadecanoate + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (R)-2-hydroxyoctadecanoate + 2 Fe(III)-[cytochrome b5] + H2O

  Catalysed by SOAT2, SOAT1, CEL, LIPA and 1 moreendoplasmic reticulum, lysosome

• O-acetyl-(R)-carnitineReach from here →
  1. Sterol O-Acyltransferase
  2. Carnitine O-Palmitoyltransferase
  3. Acetyl-CoA:carnitine O-acetyltransferase

  Catalysed by SOAT2, SOAT1, CPT1A, CPT1C and 1 moreendoplasmic reticulum, cytosolOne of 9 routes

• sn-glycerol 3-phosphateReach from here →
  1. Phosphatidylcholine:sterol O-acyltransferase
  2. 1-Acyl-sn-glycero-3-phosphocholine acylhydrolase
  3. sn-glycerol 3-phosphocholine + H2O = sn-glycerol 3-phosphate + choline + H(+)

  Catalysed by LCAT, LYPLA1, LYPLA2, PLA2G4A and 9 morecytosol

• a 1,2-diacyl-sn-glycero-3-phosphocholineReach from here →
  1. Sterol O-Acyltransferase
  2. acyl-CoA:sphingosine N-acyltransferase
  3. a 2-acyl-sn-glycero-3-phosphocholine + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phosphocholine + CoA

  Catalysed by SOAT2, SOAT1, ASAH1, ACER2 and 3 moreendoplasmic reticulum, Golgi apparatusOne of 2 routes

• an N-acylglycineReach from here →
  1. Sterol O-Acyltransferase
  2. acyl-CoA:sphingosine N-acyltransferase
  3. an acyl-CoA + glycine = an N-acylglycine + CoA + H(+)

  Catalysed by SOAT2, SOAT1, ASAH1, ACER2 and 5 moreendoplasmic reticulum, Golgi apparatusOne of 2 routes

• 2-oxo-3-sulfanylpropanoateReach from here →
  1. Sterol O-Acyltransferase
  2. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  3. L-Cysteine:2-oxoglutarate aminotransferase

  Catalysed by SOAT2, SOAT1, NAGS, GOT2 and 1 moreendoplasmic reticulum, mitochondrial matrix, cytosolOne of 3 routes

• guanidinoacetateReach from here →
  1. Sterol O-Acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. L-Arginine:glycine amidinotransferase

  Catalysed by SOAT2, SOAT1, GLYAT, GLYATL2 and 2 moreendoplasmic reticulum, mitochondrial matrix, cytosolOne of 2 routes

• D-threonineReach from here →
  1. Sterol O-Acyltransferase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. D-threonine(out) + L-alanine(in) = D-threonine(in) + L-alanine(out)

  Catalysed by SOAT2, SOAT1, SLC7A10endoplasmic reticulum, mitochondrial matrix, inner side of the membrane, outer side of the membraneOne of 2 routes

• N-sulfo-D-glucosamineReach from here →
  1. 3'-phosphoadenylyl-sulfate:cholesterol sulfotransferase
  2. Cholesterol-sulfate sulfohydrolase
  3. N-sulfo-D-glucosamine + H2O = D-glucosamine + sulfate

  Catalysed by SULT2B1, SULT1A3, STS, SGSHcytosol

• a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol)Reach from here →
  1. Sterol O-Acyltransferase
  2. acyl-CoA:sphingosine N-acyltransferase
  3. a 1-acyl-sn-glycero-3-phospho-(1D-myo-inositol) + an acyl-CoA = a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol) + CoA

  Catalysed by SOAT2, SOAT1, ASAH1, ACER2 and 4 moreendoplasmic reticulum, Golgi apparatus

• dehydroepiandrosterone 3-sulfateReach from here →
  1. 3'-phosphoadenylyl-sulfate:cholesterol sulfotransferase
  2. Cholesterol-sulfate sulfohydrolase
  3. dehydroepiandrosterone 3-sulfate + H2O = 3beta-hydroxyandrost-5-en-17-one + sulfate + H(+)

  Catalysed by SULT2B1, SULT1A3, STScytosol