CHEBI:1307929

Three steps

• 21-hydroxyprogesteroneReach from here →
  1. cytochrome P450 (cholesterol)
  2. Pregnenolone:NAD+ 3-oxidoreductase
  3. cytochrome P450 (progesterone)

  Catalysed by CYP11A1, HSD3B1, HSD3B2, CYP21A2mitochondrial matrix, cytosolOne of 3 routes

• 1-acyl-sn-glycerol 3-phosphateReach from here →
  1. Sterol O-Acyltransferase
  2. acyl-CoA:sphingosine N-acyltransferase
  3. acyl-CoA:sn-glycerol-3-phosphate 1-O-acyltransferase

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

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

  Catalysed by SULT2B1, SULT1A3, STS, SLC26A6cytosol, extracellular space

• octadecanalReach from here →
  1. Acyl-CoA:cholesterol O-acyltransferase
  2. Steryl-ester acylhydrolase
  3. octadecanal + NAD(+) + H2O = octadecanoate + NADH + 2 H(+)

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

• taurolithocholateReach from here →
  1. Sterol O-Acyltransferase
  2. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)
  3. bile acid-CoA:amino acid N-acyltransferase (lithocholate)

  Catalysed by SOAT2, SOAT1, BAATendoplasmic reticulum, cytosolOne of 2 routes

• L-isoleucineReach from here →
  1. Sterol O-Acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. transport of glycine and isoleucine (cytosol to extracellular)

  Catalysed by SOAT2, SOAT1, GLYAT, GLYATL2 and 2 moreendoplasmic reticulum, mitochondrial matrix, extracellular space, cytosolOne of 18 routes

• CHEBI:17203Reach from here →
  1. Sterol O-Acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. transport of glycine and proline (cytosol to extracellular)

  Catalysed by SOAT2, SOAT1, GLYAT, GLYATL2 and 3 moreendoplasmic reticulum, mitochondrial matrix, extracellular space, cytosolOne of 15 routes

• S-(4,8-dimethylnonanoyl)-4'-phosphopantetheineReach from here →
  1. Sterol O-Acyltransferase
  2. Carnitine Dimethyl Nonanoyl Transferase, Revsible, Peroxisomal
  3. 4,8-dimethylnonanoyl-CoA + H2O = S-(4,8-dimethylnonanoyl)-4'-phosphopantetheine + adenosine 3',5'-bisphosphate + 2 H(+)

  Catalysed by SOAT2, SOAT1, CRAT, CROT and 1 moreendoplasmic reticulum, peroxisome

• S-(9Z,12Z,15Z-octadecatrienoyl)-4'-phosphopantetheineReach from here →
  1. Sterol O-Acyltransferase
  2. long-chain-fatty-acid-CoA ligase (linolenate)
  3. (9Z,12Z,15Z)-octadecatrienoyl-CoA + H2O = S-(9Z,12Z,15Z-octadecatrienoyl)-4'-phosphopantetheine + adenosine 3',5'-bisphosphate + 2 H(+)

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

• S-(9Z,12Z-octadecadienoyl)-4'-phosphopantetheineReach from here →
  1. Sterol O-Acyltransferase
  2. long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)
  3. (9Z,12Z)-octadecadienoyl-CoA + H2O = S-(9Z,12Z-octadecadienoyl)-4'-phosphopantetheine + adenosine 3',5'-bisphosphate + 2 H(+)

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

• S-(9Z-hexadecenoyl)-4'-phosphopantetheineReach from here →
  1. Sterol O-Acyltransferase
  2. long-chain-fatty-acid-CoA ligase (palmitolate)
  3. (9Z)-hexadecenoyl-CoA + H2O = S-(9Z-hexadecenoyl)-4'-phosphopantetheine + adenosine 3',5'-bisphosphate + 2 H(+)

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

• itaconateReach from here →
  1. Sterol O-Acyltransferase
  2. Itaconate:CoA ligase (GDP-forming)
  3. Itaconate:CoA ligase (GDP-forming)

  Catalysed by SOAT2, SOAT1, SUCLG1, SUCLG2 and 1 moreendoplasmic reticulum, mitochondrial matrixOne of 4 routes

• N-octadecanoyl-heptadecasphing-4-enineReach from here →
  1. Sterol O-Acyltransferase
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. heptadecasphing-4-enine + octadecanoyl-CoA = N-octadecanoyl-heptadecasphing-4-enine + CoA + H(+)

  Catalysed by SOAT2, SOAT1, SLC27A2, ACSL4 and 6 moreendoplasmic reticulum, cytosol

• 17alpha-hydroxyprogesteroneReach from here →
  1. cytochrome P450 (cholesterol)
  2. cytochrome P450 (pregnenolone)
  3. 17alpha-Hydroxypregnenolone:NAD+ 3-oxidoreductase

  Catalysed by CYP11A1, CYP17A1, HSD3B1, HSD3B2mitochondrial matrix, cytosol, endoplasmic reticulumOne of 5 routes

• all-trans-retinolReach from here →
  1. Sterol O-Acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. all-trans-Retinol 11-cis-trans-isomerase

  Catalysed by SOAT2, SOAT1, DGAT1, LRAT and 3 moreendoplasmic reticulum, cytosolOne of 2 routes

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

• a monoacylglycerolReach from here →
  1. Phosphatidylcholine:sterol O-acyltransferase
  2. a cholesterol ester + H2O = cholesterol + a fatty acid + H(+)
  3. a monoacylglycerol + H2O = glycerol + a fatty acid + H(+)

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

• 1-(alk-1-enyl)-2-acyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. Sterol O-Acyltransferase
  2. acyl-CoA:sphingosine N-acyltransferase
  3. Acyl-CoA:1-alkenylglycerophosphoethanolamine O-acyltransferase

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

• O-hexadecanoyl-(R)-carnitineReach from here →
  1. Sterol O-Acyltransferase
  2. Carnitine O-Palmitoyltransferase
  3. palmitoyl-CoA:L-carnitine O-palmitoyltransferase

  Catalysed by SOAT2, SOAT1, CPT1A, CPT1C and 2 moreendoplasmic reticulum, cytosol, peroxisomeOne of 14 routes

• cholesteryl 3-beta-D-glucosideReach 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 7 routes

• AH2Reach 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, cytosolOne of 6 routes

• S-methyl-5'-thioadenosineReach from here →
  1. Sterol O-Acyltransferase
  2. diamine N-acetyltransferase (N1-acetylspermidine)
  3. S-adenosylmethioninamine:spermidine 3-aminopropyltransferase

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

• 5-aminolevulinic acidReach from here →
  1. Sterol O-Acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. succinyl-CoA:glycine C-succinyltransferase (decarboxylating)

  Catalysed by SOAT2, SOAT1, GLYAT, GLYATL2 and 4 moreendoplasmic reticulum, mitochondrial matrixOne of 2 routes

• hexadecanalReach from here →
  1. Acyl-CoA:cholesterol O-acyltransferase
  2. Steryl-ester acylhydrolase
  3. 2 H+[c] + NADH[c] + palmitate[c] = H2O[c] + hexadecanal[c] + NAD+[c]

  Catalysed by SOAT2, SOAT1, CEL, LIPA and 3 moreendoplasmic reticulum, lysosome, cytosolOne of 2 routes

• all-trans-retinyl hexadecanoateReach from here →
  1. Sterol O-Acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. all-trans-retinyl hexadecanoate + H2O = 11-cis-retinol + hexadecanoate + H(+)

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

• a sphingomyelinReach from here →
  1. Phosphatidylcholine:sterol O-acyltransferase
  2. Acyl-CoA:1-acyl-sn-glycero-3-phosphocholine O-acyltransferase
  3. ceramide:phosphatidylcholine cholinephosphotransferase

  Catalysed by LCAT, LPCAT4, LPCAT3, LPCAT2 and 3 morecytosol, Golgi apparatusOne of 4 routes

• 3,3'-diiodo-L-thyronine sulfateReach from here →
  1. 3'-phosphoadenylyl-sulfate:cholesterol sulfotransferase
  2. Cholesterol-sulfate sulfohydrolase
  3. Steryl-Sulfatase

  Catalysed by SULT2B1, SULT1A3, STScytosol, Golgi apparatusOne of 2 routes

• 26-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 = 26-hydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

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

• Ala-tRNA(Ala)Reach from here →
  1. Sterol O-Acyltransferase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. L-Alanine:tRNA(Ala) ligase (AMP-forming)

  Catalysed by SOAT2, SOAT1, AARS1endoplasmic reticulum, mitochondrial matrix, cytosol

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

  Catalysed by LCAT, LYPLA1, LYPLA2, PLA2G4A and 8 morecytosol

• CHEBI:17769Reach from here →
  1. Sterol O-Acyltransferase
  2. diamine N-acetyltransferase (N1-acetylspermidine)
  3. spermidine:(acceptor) oxidoreductase

  Catalysed by SOAT2, SOAT1, SAT1, SAT2endoplasmic reticulum, cytosol

• a 1,2-diacyl-sn-glycerolReach from here →
  1. Phosphatidylcholine:sterol O-acyltransferase
  2. Acyl-CoA:1-acyl-sn-glycero-3-phosphocholine O-acyltransferase
  3. ceramide:phosphatidylcholine cholinephosphotransferase

  Catalysed by LCAT, LPCAT4, LPCAT3, LPCAT2 and 3 morecytosol, Golgi apparatusOne of 5 routes

• a triacylglycerolReach from here →
  1. Sterol O-Acyltransferase
  2. acyl-CoA:sphingosine N-acyltransferase
  3. acyl-CoA:1,2-diacyl-sn-glycerol O-acyltransferase

  Catalysed by SOAT2, SOAT1, ASAH1, ACER2 and 7 moreendoplasmic reticulum, Golgi apparatus, cytosol

• CHEBI:17895Reach from here →
  1. Sterol O-Acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. transport of glycine and tyrosine (cytosol to extracellular)

  Catalysed by SOAT2, SOAT1, GLYAT, GLYATL2 and 2 moreendoplasmic reticulum, mitochondrial matrix, extracellular space, cytosolOne of 19 routes

• butanoateReach from here →
  1. Sterol O-Acyltransferase
  2. Butanoate:CoA ligase (AMP-forming)
  3. butanoyl-CoA + H2O = butanoate + CoA + H(+)

  Catalysed by SOAT2, SOAT1, ACSM4, ACSM1 and 10 moreendoplasmic reticulum, cytosol

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

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

• CHEBI:18019Reach from here →
  1. Sterol O-Acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. transport of glycine and lysine (cytosol to extracellular)

  Catalysed by SOAT2, SOAT1, GLYAT, GLYATL2 and 2 moreendoplasmic reticulum, mitochondrial matrix, extracellular space, cytosolOne of 10 routes

• L-glutamineReach from here →
  1. Sterol O-Acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. transport of glutamine and glycine (cytosol to extracellular)

  Catalysed by SOAT2, SOAT1, GLYAT, GLYATL2 and 2 moreendoplasmic reticulum, mitochondrial matrix, extracellular space, cytosolOne of 29 routes

• spermine monoaldehydeReach from here →
  1. Sterol O-Acyltransferase
  2. diamine N-acetyltransferase (N1-acetylspermine)
  3. primary-amine oxidase (spermine)

  Catalysed by SOAT2, SOAT1, SAT1, SAT2 and 3 moreendoplasmic reticulum, cytosolOne of 3 routes

• CHEBI:18095Reach from here →
  1. Sterol O-Acyltransferase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. Transport of Hydroxy-Proline

  Catalysed by SOAT2, SOAT1, SLC1A4endoplasmic reticulum, mitochondrial matrix, extracellular space, cytosol

• O-octanoyl-(R)-carnitineReach from here →
  1. Sterol O-Acyltransferase
  2. Carnitine O-Palmitoyltransferase
  3. solute carrier (L-carnitine)

  Catalysed by SOAT2, SOAT1, CPT1A, CPT1C and 2 moreendoplasmic reticulum, cytosol, mitochondrial matrixOne of 11 routes

• CHEBI:18132Reach from here →
  1. Phosphatidylcholine:sterol O-acyltransferase
  2. 1-Acyl-sn-glycero-3-phosphocholine acylhydrolase
  3. sn-Glycero-3-phosphocholine cholinephosphohydrolase

  Catalysed by LCAT, LYPLA1, LYPLA2, PLA2G4A and 8 morecytosolOne of 2 routes

• dodecanoateReach 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

• phosphatidyl-L-serineReach from here →
  1. Phosphatidylcholine:sterol O-acyltransferase
  2. Acyl-CoA:1-acyl-sn-glycero-3-phosphocholine O-acyltransferase
  3. phosphatidylserine synthase (PC-LD pool)

  Catalysed by LCAT, LPCAT4, LPCAT3, LPCAT2 and 2 morecytosol

• N(1)-(5-phospho-D-ribosyl)glycinamideReach from here →
  1. Sterol O-Acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. 5-Phospho-D-ribosylamine:glycine ligase (ADP-forming)

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

• N-(4-aminobutyl)-3-aminopropanalReach from here →
  1. Sterol O-Acyltransferase
  2. diamine N-acetyltransferase (N1-acetylspermidine)
  3. primary-amine oxidase (spermidine)

  Catalysed by SOAT2, SOAT1, SAT1, SAT2 and 3 moreendoplasmic reticulum, cytosolOne of 3 routes

• (2E,5Z,8Z,11Z,14Z,17Z)-eicosahexaenoyl-CoAReach from here →
  1. Sterol O-Acyltransferase
  2. long-chain-fatty-acid-CoA ligase (EPA)
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoyl-CoA + O2 = (2E,5Z,8Z,11Z,14Z,17Z)-eicosahexaenoyl-CoA + H2O2

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

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

  Catalysed by LCAT, CES1, LIPN, NCEH1 and 3 morecytosolOne of 2 routes

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

  Catalysed by LCAT, CES1, LIPN, NCEH1 and 3 morecytosolOne of 2 routes

• 1-octadecanoyl-2-acyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. Sterol O-Acyltransferase
  2. long-chain-fatty-acid-CoA ligase (stearate)
  3. a 2-acyl-sn-glycero-3-phosphoethanolamine + octadecanoyl-CoA = 1-octadecanoyl-2-acyl-sn-glycero-3-phosphoethanolamine + CoA

  Catalysed by SOAT2, SOAT1, SLC27A2, ACSL4 and 6 moreendoplasmic reticulum, cytosol