CHEBI:1307929

Three steps

• acetateReach from here →
  1. cytochrome P450 (cholesterol)
  2. cytochrome P450 (pregnenolone)
  3. cytochrome P450 (17alpha-hydroxypregnenolone)

  Catalysed by CYP11A1, CYP17A1mitochondrial matrix, cytosolOne of 4 routes

• 5beta-pregnan-3,20-dioneReach from here →
  1. cytochrome P450 (cholesterol)
  2. Pregnenolone:NAD+ 3-oxidoreductase
  3. progesterone + NADPH + H(+) = 5beta-pregnan-3,20-dione + NADP(+)

  Catalysed by CYP11A1, HSD3B1, HSD3B2, AKR1D1mitochondrial matrix, cytosol

• (9Z,12Z)-octadecadienoateReach from here →
  1. Sterol O-Acyltransferase
  2. long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)
  3. (9Z,12Z)-octadecadienoyl-CoA + H2O = (9Z,12Z)-octadecadienoate + CoA + H(+)

  Catalysed by SOAT2, SOAT1, SLC27A2, ACSL4 and 10 moreendoplasmic reticulum, cytosol

• 3-acetamidopropanalReach from here →
  1. Sterol O-Acyltransferase
  2. N1,N12-diacetylspermine to N1-acetylspermine conversion
  3. N1-acetylspermine:oxygen oxidoreductase (3-acetamidopropanal-forming)

  Catalysed by SOAT2, SOAT1, PAOX, SMOXendoplasmic reticulum, cytosolOne of 4 routes

• oxalateReach from here →
  1. 3'-phosphoadenylyl-sulfate:cholesterol sulfotransferase
  2. Cholesterol-sulfate sulfohydrolase
  3. oxalate(in) + sulfate(out) = oxalate(out) + sulfate(in)

  Catalysed by SULT2B1, SULT1A3, STS, SLC25A14 and 4 morecytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• propionic acidReach from here →
  1. Sterol O-Acyltransferase
  2. Propanoate:CoA ligase (AMP-forming)
  3. Propanoyl-CoA hydrolase

  Catalysed by SOAT2, SOAT1, ACSS3, ACSS2 and 2 moreendoplasmic reticulum, cytosolOne of 3 routes

• citric acidReach from here →
  1. Sterol O-Acyltransferase
  2. ATP citrate lyase (citrate)
  3. acetyl-CoA:oxaloacetate C-acetyltransferase (thioester-hydrolysing)

  Catalysed by SOAT2, SOAT1, ACLY, CSendoplasmic reticulum, cytosol, mitochondrial matrixOne of 2 routes

• butyric acidReach from here →
  1. Sterol O-Acyltransferase
  2. Butanoate:CoA ligase (AMP-forming)
  3. Butyryl-CoA hydrolase

  Catalysed by SOAT2, SOAT1, ACSM4, ACSM1 and 5 moreendoplasmic reticulum, cytosol

• maleateReach from here →
  1. 3'-phosphoadenylyl-sulfate:cholesterol sulfotransferase
  2. Cholesterol-sulfate sulfohydrolase
  3. maleate(in) + sulfate(out) = maleate(out) + sulfate(in)

  Catalysed by SULT2B1, SULT1A3, STS, SLC25A14 and 1 morecytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• malonic acidReach from here →
  1. 3'-phosphoadenylyl-sulfate:cholesterol sulfotransferase
  2. Cholesterol-sulfate sulfohydrolase
  3. transport of malonate and sulfate (cytosol to mitochondria)

  Catalysed by SULT2B1, SULT1A3, STS, SLC25A10cytosol, mitochondrial matrixOne of 2 routes

• tetradecanoateReach from here →
  1. Phosphatidylcholine:sterol O-acyltransferase
  2. 1-Acyl-sn-glycero-3-phosphocholine acylhydrolase
  3. (10Z)-heptadecenoic acid formation

  Catalysed by LCAT, LYPLA1, LYPLA2, PLA2G4A and 7 morecytosol, extracellular spaceOne of 14 routes

• adipic acidReach from here →
  1. Sterol O-Acyltransferase
  2. Activation of adipic acid for Formation of Adipoyl Carnitine
  3. Thioesterification of adipoyl-CoA for Release into Cytosol

  Catalysed by SOAT2, SOAT1, ACOT8endoplasmic reticulum, cytosol, peroxisomeOne of 3 routes

• a 1-O-alkyl-sn-glycero-3-phosphocholineReach 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. 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 CYP46A1, LCATendoplasmic reticulum

• glutarateReach from here →
  1. Sterol O-Acyltransferase
  2. Production of Glutaryl Carnitine
  3. glutaryl-CoA + H2O = glutarate + CoA + H(+)

  Catalysed by SOAT2, SOAT1, CPT1A, CPT1C and 3 moreendoplasmic reticulum, cytosolOne of 5 routes

• 4-hydroxy-2-oxoglutaric acidReach from here →
  1. Sterol O-Acyltransferase
  2. ATP citrate lyase (citrate)
  3. D-aspartate:2-oxoglutarate aminotransferase

  Catalysed by SOAT2, SOAT1, ACLY, GOT2endoplasmic reticulum, cytosol, mitochondrial matrix

• (2R,3R)-tartrateReach from here →
  1. 3'-phosphoadenylyl-sulfate:cholesterol sulfotransferase
  2. Cholesterol-sulfate sulfohydrolase
  3. (2R,3R)-tartrate(in) + sulfate(out) = (2R,3R)-tartrate(out) + sulfate(in)

  Catalysed by SULT2B1, SULT1A3, STS, SLC25A14 and 1 morecytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• (S,S)-tartrateReach from here →
  1. 3'-phosphoadenylyl-sulfate:cholesterol sulfotransferase
  2. Cholesterol-sulfate sulfohydrolase
  3. (S,S)-tartrate(in) + sulfate(out) = (S,S)-tartrate(out) + sulfate(in)

  Catalysed by SULT2B1, SULT1A3, STS, SLC25A14 and 1 morecytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• (3R)-citramalateReach from here →
  1. 3'-phosphoadenylyl-sulfate:cholesterol sulfotransferase
  2. Cholesterol-sulfate sulfohydrolase
  3. (3R)-citramalate(in) + sulfate(out) = (3R)-citramalate(out) + sulfate(in)

  Catalysed by SULT2B1, SULT1A3, STS, SLC25A14 and 1 morecytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• (3S)-citramalateReach from here →
  1. 3'-phosphoadenylyl-sulfate:cholesterol sulfotransferase
  2. Cholesterol-sulfate sulfohydrolase
  3. (3S)-citramalate(in) + sulfate(out) = (3S)-citramalate(out) + sulfate(in)

  Catalysed by SULT2B1, SULT1A3, STS, SLC25A14 and 1 morecytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• docosan-1-olReach from here →
  1. Sterol O-Acyltransferase
  2. long-chain-fatty-acid-CoA ligase (behenic acid)
  3. docosanoyl-CoA + 2 NADPH + 2 H(+) = docosan-1-ol + 2 NADP(+) + CoA

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

• hexacosanoateReach from here →
  1. Phosphatidylcholine:sterol O-acyltransferase
  2. 1-Acyl-sn-glycero-3-phosphocholine acylhydrolase
  3. (10Z)-heptadecenoic acid formation

  Catalysed by LCAT, LYPLA1, LYPLA2, PLA2G4A and 7 morecytosol, extracellular spaceOne of 14 routes

• tetracosanoateReach from here →
  1. Phosphatidylcholine:sterol O-acyltransferase
  2. 1-Acyl-sn-glycero-3-phosphocholine acylhydrolase
  3. (10Z)-heptadecenoic acid formation

  Catalysed by LCAT, LYPLA1, LYPLA2, PLA2G4A and 7 morecytosol, extracellular spaceOne of 16 routes

• an N-acylsphinganineReach from here →
  1. Phosphatidylcholine:sterol O-acyltransferase
  2. 1-Acyl-sn-glycero-3-phosphocholine acylhydrolase
  3. N-acylsphingosine amidohydrolase

  Catalysed by LCAT, LYPLA1, LYPLA2, PLA2G4A and 12 morecytosolOne of 2 routes

• octadecan-1-olReach from here →
  1. Sterol O-Acyltransferase
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. octadecanoyl-CoA + 2 NADPH + 2 H(+) = octadecan-1-ol + 2 NADP(+) + CoA

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

• eicosanoateReach from here →
  1. Phosphatidylcholine:sterol O-acyltransferase
  2. 1-Acyl-sn-glycero-3-phosphocholine acylhydrolase
  3. (10Z)-heptadecenoic acid formation

  Catalysed by LCAT, LYPLA1, LYPLA2, PLA2G4A and 7 morecytosol, extracellular spaceOne of 16 routes

• (9Z)-hexadecenoateReach from here →
  1. Phosphatidylcholine:sterol O-acyltransferase
  2. 1-Acyl-sn-glycero-3-phosphocholine acylhydrolase
  3. (10Z)-heptadecenoic acid formation

  Catalysed by LCAT, LYPLA1, LYPLA2, PLA2G4A and 7 morecytosol, extracellular spaceOne of 20 routes

• (15Z)-tetracosenoateReach from here →
  1. Phosphatidylcholine:sterol O-acyltransferase
  2. 1-Acyl-sn-glycero-3-phosphocholine acylhydrolase
  3. (10Z)-heptadecenoic acid formation

  Catalysed by LCAT, LYPLA1, LYPLA2, PLA2G4A and 7 morecytosol, extracellular spaceOne of 13 routes

• (5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. Phosphatidylcholine:sterol O-acyltransferase
  2. 1-Acyl-sn-glycero-3-phosphocholine acylhydrolase
  3. (10Z)-heptadecenoic acid formation

  Catalysed by LCAT, LYPLA1, LYPLA2, PLA2G4A and 7 morecytosol, extracellular spaceOne of 16 routes

• (11Z)-eicosenoateReach from here →
  1. Phosphatidylcholine:sterol O-acyltransferase
  2. 1-Acyl-sn-glycero-3-phosphocholine acylhydrolase
  3. (10Z)-heptadecenoic acid formation

  Catalysed by LCAT, LYPLA1, LYPLA2, PLA2G4A and 7 morecytosol, extracellular spaceOne of 13 routes

• putrescineReach 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, cytosolOne of 3 routes

• thiosulfateReach from here →
  1. 3'-phosphoadenylyl-sulfate:cholesterol sulfotransferase
  2. Cholesterol-sulfate sulfohydrolase
  3. thiosulfate(in) + sulfate(out) = thiosulfate(out) + sulfate(in)

  Catalysed by SULT2B1, SULT1A3, STS, SLC25A14 and 3 morecytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• 4-methylthio-2-oxobutanoic acidReach from here →
  1. Sterol O-Acyltransferase
  2. N-acetylglutamate synthase (N-acetylmethionine)
  3. L-Methionine:oxygen oxidoreductase (deaminating)

  Catalysed by SOAT2, SOAT1, NAGS, IL4I1endoplasmic reticulum, mitochondrial matrix, cytosol

• di-mu-sulfido-diiron(2+)Reach from here →
  1. Sterol O-Acyltransferase
  2. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  3. De novo synthesis of 2Fe2S

  Catalysed by SOAT2, SOAT1, NAGS, NDUFAB1 and 6 moreendoplasmic reticulum, mitochondrial matrix

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

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

  Catalysed by SOAT2, SOAT1, SLC7A10endoplasmic reticulum, mitochondrial matrix, inner side of the membrane, outer side of the membraneOne of 6 routes

• an acylcholineReach from here →
  1. Sterol O-Acyltransferase
  2. Acetyl-CoA:choline O-acetyltransferase
  3. an acylcholine + H2O = a carboxylate + choline + H(+)

  Catalysed by SOAT2, SOAT1, CHAT, BCHEendoplasmic reticulum, nucleus

• 5-aminolevulinateReach from here →
  1. Sterol O-Acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. succinyl-CoA + glycine + H(+) = 5-aminolevulinate + CO2 + CoA

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

• a fatty aldehydeReach from here →
  1. Phosphatidylcholine:sterol O-acyltransferase
  2. a cholesterol ester + H2O = cholesterol + a fatty acid + H(+)
  3. a fatty aldehyde + NAD(+) + H2O = a fatty acid + NADH + 2 H(+)

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

• chenodeoxycholateReach from here →
  1. Sterol O-Acyltransferase
  2. Propanoyl-CoA:acetyl-CoA C-acyltransferase
  3. chenodeoxycholoyl-CoA hydrolase

  Catalysed by SOAT2, SOAT1, ACAA1, SCP2 and 4 moreendoplasmic reticulum, peroxisomeOne of 3 routes

• glycochenodeoxycholateReach from here →
  1. Sterol O-Acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. chenodeoxycholoyl-CoA + glycine = glycochenodeoxycholate + CoA + H(+)

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

• taurocholateReach from here →
  1. Sterol O-Acyltransferase
  2. propanoyl-CoA C-acyltransferase
  3. Choloyl-CoA:glycine N-choloyltransferase

  Catalysed by SOAT2, SOAT1, ACAA1, SCP2 and 2 moreendoplasmic reticulum, peroxisomeOne of 5 routes

• taurodeoxycholateReach from here →
  1. Sterol O-Acyltransferase
  2. cholate-CoA ligase (3alpha,12alpha-dihydroxy-5beta-cholanate)
  3. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)

  Catalysed by SOAT2, SOAT1, SLC27A2, SLC27A5 and 1 moreendoplasmic reticulum, cytosolOne of 4 routes

• glycochenodeoxycholic acidReach from here →
  1. Sterol O-Acyltransferase
  2. Propanoyl-CoA:acetyl-CoA C-acyltransferase
  3. bile acid-CoA: amino acid N-acyltransferase

  Catalysed by SOAT2, SOAT1, ACAA1, SCP2 and 2 moreendoplasmic reticulum, peroxisomeOne of 5 routes

• glyoxylateReach from here →
  1. Sterol O-Acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. glycine + 2-oxoglutarate = glyoxylate + L-glutamate

  Catalysed by SOAT2, SOAT1, GLYAT, GLYATL2 and 2 moreendoplasmic reticulum, mitochondrial matrixOne of 11 routes

• a 1-O-alkyl-2-acyl-sn-glycero-3-phosphocholineReach from here →
  1. Sterol O-Acyltransferase
  2. acyl-CoA:sphingosine N-acyltransferase
  3. Acyl-CoA:1-alkyl-sn-glycero-3-phosphocholine O-acyltransferase

  Catalysed by SOAT2, SOAT1, ASAH1, ACER2 and 6 moreendoplasmic reticulum, Golgi apparatus, cytosol

• (20R)-20-hydroxypregn-4-en-3-oneReach from here →
  1. cytochrome P450 (cholesterol)
  2. Pregnenolone:NAD+ 3-oxidoreductase
  3. 20alpha-Hydroxy-4-pregnen-3-one:NADP+ 20-oxidoreductase

  Catalysed by CYP11A1, HSD3B1, HSD3B2, AKR1C1mitochondrial matrix, cytosol

• CHEBI:36882Reach from here →
  1. Sterol O-Acyltransferase
  2. Itaconate:CoA ligase (GDP-forming)
  3. (3S)-citramalyl-CoA hydro-lyase (itaconyl-CoA-forming)

  Catalysed by SOAT2, SOAT1, SUCLG1, SUCLG2 and 2 moreendoplasmic reticulum, mitochondrial matrix

• 3-hydroxyisovaleric acidReach from here →
  1. Sterol O-Acyltransferase
  2. (3-Hydroxyisovalerylcoa->3-Hydroxyisovalerylcarnitine)
  3. Formation of 3-Hydroxy-Isovalerate

  Catalysed by SOAT2, SOAT1, CPT1A, CPT1Bendoplasmic reticulum, cytosol, mitochondrial matrix

• 3,7,11,15-tetramethylhexadecanoateReach from here →
  1. Sterol O-Acyltransferase
  2. phytanate-CoA ligase
  3. peroxisomal acyl-CoA thioesterase

  Catalysed by SOAT2, SOAT1, ACOT2endoplasmic reticulum, cytosol, peroxisomeOne of 3 routes

• sphingosine 1-phosphateReach from here →
  1. Sterol O-Acyltransferase
  2. acyl-CoA:sphingosine N-acyltransferase
  3. ATP:sphingosine 1-phosphotransferase

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