CHEBI:1307929

Three steps

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

  Catalysed by SOAT2, SOAT1, GLYAT, GLYATL2 and 2 moreendoplasmic reticulum, mitochondrial matrix, extracellular space, cytosolOne of 20 routes

• glutathioneReach from here →
  1. Sterol O-Acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. gamma-L-glutamyl-L-cysteine + glycine + ATP = glutathione + ADP + phosphate + H(+)

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

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

  Catalysed by SOAT2, SOAT1, SLC7A10endoplasmic reticulum, mitochondrial matrix, inner side of the membrane, outer side of the membraneOne of 4 routes

• L-kynurenineReach from here →
  1. Sterol O-Acyltransferase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. L-kynurenine + H2O = anthranilate + L-alanine + H(+)

  Catalysed by SOAT2, SOAT1, KYNUendoplasmic reticulum, mitochondrial matrix

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

  Catalysed by SOAT2, SOAT1, SLC7A10endoplasmic reticulum, mitochondrial matrix, inner side of the membrane, outer side of the membraneOne of 3 routes

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

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

• leukotriene C4Reach from here →
  1. Sterol O-Acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. leukotriene C4 hydrolysis

  Catalysed by SOAT2, SOAT1, GLYAT, GLYATL2 and 1 moreendoplasmic reticulum, mitochondrial matrix, cytosol

• taurocyamineReach 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, cytosol

• glycerol 2-phosphateReach from here →
  1. Phosphatidylcholine:sterol O-acyltransferase
  2. 1-Acyl-sn-glycero-3-phosphocholine acylhydrolase
  3. Glycerophosphocholine Phosphodiesterase

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

• L-cysteateReach from here →
  1. Sterol O-Acyltransferase
  2. bile acid-CoA:amino acid N-acyltransferase (taurodeoxycholate)
  3. L-cysteate + H(+) = taurine + CO2

  Catalysed by SOAT2, SOAT1, BAAT, GADL1 and 1 moreendoplasmic reticulum, cytosol

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

  Catalysed by SOAT2, SOAT1, GLYAT, GLYATL2 and 2 moreendoplasmic reticulum, mitochondrial matrix, extracellular space, cytosolOne of 28 routes

• N(1)-acetylspermineReach from here →
  1. Sterol O-Acyltransferase
  2. diamine N-acetyltransferase (N1-acetylspermidine)
  3. N(1)-acetylspermine + O2 + H2O = 3-acetamidopropanal + spermidine + H2O2

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

• 3-hydroxy-L-kynurenineReach from here →
  1. Sterol O-Acyltransferase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. 3-hydroxy-L-kynurenine + H2O = 3-hydroxyanthranilate + L-alanine + H(+)

  Catalysed by SOAT2, SOAT1, KYNUendoplasmic reticulum, mitochondrial matrix

• gamma-L-glutamyl-L-cysteineReach from here →
  1. Sterol O-Acyltransferase
  2. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  3. L-glutamate:L-cysteine gamma-ligase (ADP-forming)

  Catalysed by SOAT2, SOAT1, NAGS, GCLC and 1 moreendoplasmic reticulum, mitochondrial matrix, cytosolOne of 2 routes

• a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol 4-phosphate)Reach from here →
  1. Phosphatidylcholine:sterol O-acyltransferase
  2. a cholesterol ester + H2O = cholesterol + a fatty acid + H(+)
  3. 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)

  Catalysed by LCAT, CES1, LIPN, NCEH1 and 2 morecytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• L-homocysteineReach from here →
  1. Sterol O-Acyltransferase
  2. N-acetylglutamate synthase (N-acetyl-L-cystathionine)
  3. L-homocysteine + L-serine = L,L-cystathionine + H2O

  Catalysed by SOAT2, SOAT1, NAGS, CBSendoplasmic reticulum, mitochondrial matrixOne of 2 routes

• adenosine 5'-phosphosulfateReach from here →
  1. 3'-phosphoadenylyl-sulfate:cholesterol sulfotransferase
  2. Cholesterol-sulfate sulfohydrolase
  3. ATP:sulfate adenylyltransferase

  Catalysed by SULT2B1, SULT1A3, STS, PAPSS1 and 1 morecytosolOne of 4 routes

• S-methyl-L-methionineReach from here →
  1. Sterol O-Acyltransferase
  2. N-acetylglutamate synthase (N-acetylmethionine)
  3. S-methyl-L-methionine + L-homocysteine = 2 L-methionine + H(+)

  Catalysed by SOAT2, SOAT1, NAGS, BHMT2endoplasmic reticulum, mitochondrial matrix

• 3-oxosphinganineReach from here →
  1. Sterol O-Acyltransferase
  2. Palmitate:CoA ligase (AMP-forming)
  3. Palmitoyl-CoA:L-serine C-palmitoyltransferase (decarboxylating)

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

• 1-hexadecanoylglycerone 3-phosphateReach from here →
  1. Sterol O-Acyltransferase
  2. Palmitate:CoA ligase (AMP-forming)
  3. glyceronephosphate O-acyltransferase (DHAP)

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

• L-tyrosineReach from here →
  1. Sterol O-Acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. L-tyrosine + glyoxylate = 3-(4-hydroxyphenyl)pyruvate + glycine

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

• N(1)-acetylspermidineReach from here →
  1. Sterol O-Acyltransferase
  2. diamine N-acetyltransferase (N1-acetylspermidine)
  3. spermidine + acetyl-CoA = N(1)-acetylspermidine + CoA + H(+)

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

• N(omega),N(omega)-dimethyl-L-arginineReach from here →
  1. Sterol O-Acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. N(omega),N(omega)-dimethyl-L-arginine + glyoxylate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + glycine

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

• 3-aminopropanalReach from here →
  1. Sterol O-Acyltransferase
  2. diamine N-acetyltransferase (N1-acetylspermine)
  3. spermidine:oxygen oxidoreductase (spermidine-forming)

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

• trans-4-hydroxy-L-prolineReach from here →
  1. Sterol O-Acyltransferase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. trans-4-hydroxy-L-proline(out) + L-alanine(in) + Na(+)(out) = trans-4-hydroxy-L-proline(in) + L-alanine(out) + Na(+)(in)

  Catalysed by SOAT2, SOAT1, SLC1A4endoplasmic reticulum, mitochondrial matrix, inner side of the membrane, outer side of the membraneOne of 2 routes

• a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol-4,5-bisphosphate)Reach from here →
  1. Phosphatidylcholine:sterol O-acyltransferase
  2. a cholesterol ester + H2O = cholesterol + a fatty acid + H(+)
  3. 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)

  Catalysed by LCAT, CES1, LIPN, NCEH1 and 3 morecytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• N(8)-acetylspermidineReach from here →
  1. Sterol O-Acyltransferase
  2. diamine N-acetyltransferase (N1-acetylspermidine)
  3. N8-acetylspermidine to spermidine conversion

  Catalysed by SOAT2, SOAT1, SAT1, SAT2endoplasmic reticulum, cytosolOne of 3 routes

• N(1),N(12)-diacetylspermineReach from here →
  1. Sterol O-Acyltransferase
  2. N1,N12-diacetylspermine to N1-acetylspermine conversion
  3. N1,N12-diacetylspermine to N1-acetylspermine conversion

  Catalysed by SOAT2, SOAT1endoplasmic reticulum, cytosolOne of 2 routes

• S-sulfanyl-L-cysteineReach from here →
  1. Sterol O-Acyltransferase
  2. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  3. 2 L-cysteine = S-sulfanyl-L-cysteine + L-alanine

  Catalysed by SOAT2, SOAT1, NAGS, CARS2endoplasmic reticulum, mitochondrial matrix

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

  Catalysed by SOAT2, SOAT1, ASAH1, ACER2 and 15 moreendoplasmic reticulum, Golgi apparatus

• (3S)-citramalyl-CoAReach from here →
  1. Sterol O-Acyltransferase
  2. Itaconate:CoA ligase (GDP-forming)
  3. (3S)-citramalyl-CoA = itaconyl-CoA + H2O

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

• phosphoenolpyruvateReach from here →
  1. Sterol O-Acyltransferase
  2. ATP citrate lyase (citrate)
  3. oxaloacetate + GTP = phosphoenolpyruvate + GDP + CO2

  Catalysed by SOAT2, SOAT1, ACLY, PCK1 and 1 moreendoplasmic reticulum, cytosol

• L-methionine (S)-S-oxideReach from here →
  1. Sterol O-Acyltransferase
  2. N-acetylglutamate synthase (N-acetylmethionine)
  3. [thioredoxin]-disulfide + L-methionine + H2O = L-methionine (S)-S-oxide + [thioredoxin]-dithiol

  Catalysed by SOAT2, SOAT1, NAGS, MSRAendoplasmic reticulum, mitochondrial matrix

• L-methionine (R)-S-oxideReach from here →
  1. Sterol O-Acyltransferase
  2. N-acetylglutamate synthase (N-acetylmethionine)
  3. [thioredoxin]-disulfide + L-methionine + H2O = L-methionine (R)-S-oxide + [thioredoxin]-dithiol

  Catalysed by SOAT2, SOAT1, NAGS, MSRB3 and 2 moreendoplasmic reticulum, mitochondrial matrix

• N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycineReach from here →
  1. Sterol O-Acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + glycine = N-(5Z,8Z,11Z,14Z)-eicosatetraenoyl-glycine + CoA + H(+)

  Catalysed by SOAT2, SOAT1, GLYAT, GLYATL2 and 1 moreendoplasmic reticulum, mitochondrial matrixOne of 2 routes

• N-[(R)-4-phosphopantothenoyl]-L-cysteineReach from here →
  1. Sterol O-Acyltransferase
  2. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  3. (R)-4'-phosphopantothenate:L-cysteine ligase

  Catalysed by SOAT2, SOAT1, NAGS, PPCSendoplasmic reticulum, mitochondrial matrix, cytosolOne of 4 routes

• 1-acyl-2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphocholineReach from here →
  1. Sterol O-Acyltransferase
  2. long-chain-fatty-acid-CoA ligase ((6Z,9Z)-octadecadienoic acid)
  3. (9Z,12Z)-octadecadienoyl-CoA + a 1-acyl-sn-glycero-3-phosphocholine = 1-acyl-2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphocholine + CoA

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

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

  Catalysed by SOAT2, SOAT1, SLC1A4endoplasmic reticulum, mitochondrial matrix, inner side of the membrane, outer side of the membraneOne of 2 routes

• estrone 3-sulfateReach from here →
  1. 3'-phosphoadenylyl-sulfate:cholesterol sulfotransferase
  2. Cholesterol-sulfate sulfohydrolase
  3. estrone 3-sulfate + H2O = estrone + sulfate + H(+)

  Catalysed by SULT2B1, SULT1A3, STScytosol

• sphing-4-enine 1-phosphateReach from here →
  1. Sterol O-Acyltransferase
  2. acyl-CoA:sphingosine N-acyltransferase
  3. sphing-4-enine + ATP = sphing-4-enine 1-phosphate + ADP + H(+)

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

• N-benzoylglycineReach from here →
  1. Sterol O-Acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. Hippurate (Benzoylglycinate) Formation

  Catalysed by SOAT2, SOAT1, GLYAT, GLYATL2 and 1 moreendoplasmic reticulum, mitochondrial matrixOne of 2 routes

• (9S)-hydroperoxy-(10E,12Z)-octadecadienoateReach from here →
  1. Acyl-CoA:cholesterol O-acyltransferase
  2. Steryl-ester acylhydrolase
  3. linoleate:oxygen 9-oxidoreductase

  Catalysed by SOAT2, SOAT1, CEL, LIPAendoplasmic reticulum, lysosome, cytosol

• 3-sulfino-L-alanineReach from here →
  1. Sterol O-Acyltransferase
  2. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  3. L-Cysteine:oxygen oxidoreductase

  Catalysed by SOAT2, SOAT1, NAGS, CDO1endoplasmic reticulum, mitochondrial matrix, cytosolOne of 2 routes

• (2E)-tetradecenoyl-CoAReach from here →
  1. Sterol O-Acyltransferase
  2. long-chain-fatty-acid-CoA ligase (myristic acid)
  3. trans-tetradec-2-enoyl-CoA reductase

  Catalysed by SOAT2, SOAT1, SLC27A2, ACSL4 and 7 moreendoplasmic reticulum, cytosol, mitochondrial matrixOne of 5 routes

• (2E)-decenoyl-CoAReach from here →
  1. Sterol O-Acyltransferase
  2. medium-chain acyl-CoA ligase (decanoic acid)
  3. trans-dec-2-enoyl-CoA reductase

  Catalysed by SOAT2, SOAT1, ACSM4, ACSM1 and 5 moreendoplasmic reticulum, cytosol, mitochondrial matrixOne of 8 routes

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

  Catalysed by SOAT2, SOAT1, GGTLC3, GGT1 and 4 moreendoplasmic reticulum, mitochondrial matrix, cytosolOne of 2 routes

• (2E)-hexenoyl-CoAReach from here →
  1. Sterol O-Acyltransferase
  2. medium-chain acyl-CoA ligase (hexanoic acid)
  3. trans-hex-2-enoyl-CoA reductase

  Catalysed by SOAT2, SOAT1, ACSM4, ACSM1 and 5 moreendoplasmic reticulum, cytosol, mitochondrial matrixOne of 3 routes

• 6beta-hydroxyprogesteroneReach from here →
  1. cytochrome P450 (cholesterol)
  2. Pregnenolone:NAD+ 3-oxidoreductase
  3. progesterone + reduced [NADPH--hemoprotein reductase] + O2 = 6beta-hydroxyprogesterone + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CYP11A1, HSD3B1, HSD3B2, CYP3A4 and 2 moremitochondrial matrix, cytosol

• a cardiolipinReach from here →
  1. Sterol O-Acyltransferase
  2. acyl-CoA:sphingosine N-acyltransferase
  3. 1'-[1,2-diacyl-sn-glycero-3-phospho],3'-[1-acyl-sn-glycero-3-phospho]-glycerol + an acyl-CoA = a cardiolipin + CoA

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

• (2E)-octenoyl-CoAReach from here →
  1. Sterol O-Acyltransferase
  2. Octanoyl-CoA:L-carnitine O-octanoyltransferase
  3. trans-oct-2-enoyl-CoA reductase

  Catalysed by SOAT2, SOAT1, CROT, MECRendoplasmic reticulum, mitochondrial matrixOne of 5 routes