CHEBI:1307929

Three steps

• ophthalmateReach from here →
  1. Sterol O-Acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. gamma-L-glutamyl-(2S)-2-aminobutanoate + glycine + ATP = ophthalmate + ADP + phosphate + H(+)

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

• S-methylmercury-L-cysteineReach from here →
  1. Sterol O-Acyltransferase
  2. N-acetylglutamate synthase (N-acetylmethionine)
  3. S-methylmercury-L-cysteine(out) + L-methionine(in) = S-methylmercury-L-cysteine(in) + L-methionine(out)

  Catalysed by SOAT2, SOAT1, NAGS, SLC7A8endoplasmic reticulum, mitochondrial matrix, inner side of the membrane, outer side of the membraneOne of 2 routes

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

• 11-cis-retinyl esterReach from here →
  1. Sterol O-Acyltransferase
  2. Palmitoyl-CoA:retinol O-acyltransferase
  3. 11-cis-retinol + a fatty acyl-CoA = 11-cis-retinyl ester + CoA

  Catalysed by SOAT2, SOAT1, DGAT1, LRAT and 3 moreendoplasmic reticulum, cytosol

• (5S)-hydroperoxy-(6E,8Z,11Z,14Z,17Z)-eicosapentaenoateReach from here →
  1. Acyl-CoA:cholesterol O-acyltransferase
  2. Steryl-ester acylhydrolase
  3. (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + O2 = (5S)-hydroperoxy-(6E,8Z,11Z,14Z,17Z)-eicosapentaenoate

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

• 5-(3,3-dimethylguanidino)-2-oxopentanoateReach from here →
  1. Sterol O-Acyltransferase
  2. ATP citrate lyase (citrate)
  3. N(omega),N(omega)-dimethyl-L-arginine + oxaloacetate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + L-aspartate

  Catalysed by SOAT2, SOAT1, ACLY, AGXT2endoplasmic 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

• 1-butanoyl-2-(9Z-octadecenoyl)-glycerolReach from here →
  1. Sterol O-Acyltransferase
  2. Butanoate:CoA ligase (AMP-forming)
  3. 2-(9Z-octadecenoyl)-glycerol + butanoyl-CoA = 1-butanoyl-2-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by SOAT2, SOAT1, ACSM4, ACSM1 and 6 moreendoplasmic reticulum, cytosol

• 1-octanoyl-2-(9Z-octadecenoyl)-glycerolReach from here →
  1. Sterol O-Acyltransferase
  2. Octanoyl-CoA:L-carnitine O-octanoyltransferase
  3. 2-(9Z-octadecenoyl)-glycerol + octanoyl-CoA = 1-octanoyl-2-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by SOAT2, SOAT1, CROT, MOGAT2 and 1 moreendoplasmic reticulum, mitochondrial matrix

• 1-eicosanoyl-2-(9Z-octadecenoyl)-glycerolReach from here →
  1. Sterol O-Acyltransferase
  2. long-chain-fatty-acid-CoA ligase (eicosanoate)
  3. eicosanoyl-CoA + 2-(9Z-octadecenoyl)-glycerol = 1-eicosanoyl-2-(9Z-octadecenoyl)-glycerol + CoA

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

• 5,6,7,8-tetrahydrofolic acidReach from here →
  1. Sterol O-Acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. 5,10-Methylenetetrahydrofolate:glycine hydroxymethyltransferase

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

• O-butanoyl-(R)-carnitineReach from here →
  1. Sterol O-Acyltransferase
  2. Butanoate:CoA ligase (AMP-forming)
  3. butanoyl-CoA + (R)-carnitine = O-butanoyl-(R)-carnitine + CoA

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

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

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

• 3-oxo-(9Z)-eicosenoyl-CoAReach from here →
  1. Sterol O-Acyltransferase
  2. carnitine O-palmitoyltransferase ((7Z)-octadecenoyl-CoA)
  3. very-long-chain 3-oxoacyl-CoA synthase ((7Z)-octadecenoyl-CoA)

  Catalysed by SOAT2, SOAT1, CPT1A, CPT1C and 8 moreendoplasmic reticulum, cytosol

• (2E,6Z,9Z,12Z)-octadecatetraenoyl-CoAReach from here →
  1. Sterol O-Acyltransferase
  2. long-chain-fatty-acid-CoA ligase (gamma-linolenate)
  3. (6Z,9Z,12Z)-octadecatrienoyl-CoA + oxidized [electron-transfer flavoprotein] + H(+) = (2E,6Z,9Z,12Z)-octadecatetraenoyl-CoA + reduced [electron-transfer flavoprotein]

  Catalysed by SOAT2, SOAT1, SLC27A2, ACSL4 and 9 moreendoplasmic reticulum, cytosolOne of 2 routes

• (2E,7Z,10Z)-hexadecatrienoyl-CoAReach from here →
  1. Sterol O-Acyltransferase
  2. Fatty Acid Beta Oxidation Trans (C18:2->C16:2), Mitochondrial
  3. (7Z,10Z)-hexadecadienoyl-CoA + oxidized [electron-transfer flavoprotein] + H(+) = (2E,7Z,10Z)-hexadecatrienoyl-CoA + reduced [electron-transfer flavoprotein]

  Catalysed by SOAT2, SOAT1, HADHA, ACADVL and 3 moreendoplasmic reticulum, mitochondrial matrix

• (2E,4Z,7Z,10Z,13Z)-hexadecapentaenoyl-CoAReach from here →
  1. Sterol O-Acyltransferase
  2. Fatty Acid Beta Oxidation (C18:4->C16:4), Mitochondrial
  3. Fatty Acid Beta Oxidation (C16:4->C16:5), Mitochondrial

  Catalysed by SOAT2, SOAT1, HADHA, ACADVL and 1 moreendoplasmic reticulum, mitochondrial matrixOne of 4 routes

• (2E,7Z,10Z,13Z)-hexadecatetraenoyl-CoAReach from here →
  1. Sterol O-Acyltransferase
  2. Fatty Acid Beta Oxidation (C18:3->C16:3), Mitochondrial
  3. (7Z,10Z,13Z)-hexadecatrienoyl-CoA + oxidized [electron-transfer flavoprotein] + H(+) = (2E,7Z,10Z,13Z)-hexadecatetraenoyl-CoA + reduced [electron-transfer flavoprotein]

  Catalysed by SOAT2, SOAT1, HADHA, ACADVL and 3 moreendoplasmic reticulum, mitochondrial matrix

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

  Catalysed by SOAT2, SOAT1, ECHS1, ACAA2 and 2 moreendoplasmic reticulum, mitochondrial matrixOne of 3 routes

• docosanoateReach 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

• CHEBI:240943Reach from here →
  1. Sterol O-Acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. glycine N-acyltransferase (2-methylbutyryl-CoA)

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

• octanoateReach from here →
  1. Sterol O-Acyltransferase
  2. Octanoyl-CoA:L-carnitine O-octanoyltransferase
  3. Octanoyl-CoA hydrolase

  Catalysed by SOAT2, SOAT1, CROT, ACOT7endoplasmic reticulum, mitochondrial matrix, cytosolOne of 2 routes

• alpha-linolenic acidReach 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

• folic acidReach from here →
  1. 3'-phosphoadenylyl-sulfate:cholesterol sulfotransferase
  2. Cholesterol-sulfate sulfohydrolase
  3. Folate Transport by Oats

  Catalysed by SULT2B1, SULT1A3, STS, SLC22A8 and 1 morecytosol, extracellular spaceOne of 2 routes

• phenylacetylglycineReach from here →
  1. Sterol O-Acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. phenylacetyl-CoA:glycine N-phenylacetyltransferase

  Catalysed by SOAT2, SOAT1, GLYAT, GLYATL2 and 1 moreendoplasmic reticulum, mitochondrial matrix, cytosolOne of 6 routes

• decanoateReach from here →
  1. Sterol O-Acyltransferase
  2. medium-chain acyl-CoA ligase (decanoic acid)
  3. Decanoyl-CoA hydrolase

  Catalysed by SOAT2, SOAT1, ACSM4, ACSM1 and 5 moreendoplasmic reticulum, cytosolOne of 2 routes

• 17alpha,21-dihydroxypregnenoloneReach from here →
  1. cytochrome P450 (cholesterol)
  2. cytochrome P450 (pregnenolone)
  3. cytochrome P450

  Catalysed by CYP11A1, CYP17A1, CYP21A2mitochondrial matrix, cytosol

• all-cis-docosa-4,7,10,13,16,19-hexaenoic acidReach 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

• 11beta-hydroxyprogesteroneReach from here →
  1. cytochrome P450 (cholesterol)
  2. Pregnenolone:NAD+ 3-oxidoreductase
  3. progesterone,reduced ferredoxin:oxygen oxidoreductase (11-hydroxylating)

  Catalysed by CYP11A1, HSD3B1, HSD3B2, CYP11B1 and 1 moremitochondrial matrix, cytosolOne of 2 routes

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

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

• (20S)-hydroxypregn-4-en-3-oneReach from here →
  1. cytochrome P450 (cholesterol)
  2. Pregnenolone:NAD+ 3-oxidoreductase
  3. (20S)-hydroxypregn-4-en-3-one + NAD(+) = progesterone + NADH + H(+)

  Catalysed by CYP11A1, HSD3B1, HSD3B2, AKR1C4 and 4 moremitochondrial matrix, cytosolOne of 2 routes

• 1-(9Z-octadecenoyl)-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. 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 CYP46A1, LCAT, TAFAZZINendoplasmic reticulum

• CHEBI:28666Reach from here →
  1. Sterol O-Acyltransferase
  2. N-acetyl-LTE4 to leukotriene E4 conversion
  3. LTD4 hydrolysis

  Catalysed by SOAT2, SOAT1, ZDHHC11B, NAA10 and 30 moreendoplasmic reticulum, cytosolOne of 2 routes

• 3beta-hydroxyandrost-5-en-17-oneReach from here →
  1. cytochrome P450 (cholesterol)
  2. cytochrome P450 (pregnenolone)
  3. cytochrome P450 (17alpha-hydroxypregnenolone)

  Catalysed by CYP11A1, CYP17A1mitochondrial matrix, cytosolOne of 6 routes

• O-decanoyl-(R)-carnitineReach from here →
  1. Sterol O-Acyltransferase
  2. medium-chain acyl-CoA ligase (decanoic acid)
  3. decanoyl-CoA + (R)-carnitine = O-decanoyl-(R)-carnitine + CoA

  Catalysed by SOAT2, SOAT1, ACSM4, ACSM1 and 6 moreendoplasmic reticulum, cytosol

• pyridoxine 5'-phosphateReach from here →
  1. Sterol O-Acyltransferase
  2. amino-acid N-acetyltransferase (N-acetyl-L-alanine)
  3. L-selenocysteine selenide-lyase (L-alanine-forming)

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

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

  Catalysed by SOAT2, SOAT1, NAGSendoplasmic reticulum, mitochondrial matrix

• 5alpha-pregnane-3,20-dioneReach from here →
  1. cytochrome P450 (cholesterol)
  2. Pregnenolone:NAD+ 3-oxidoreductase
  3. 5alpha-pregnane-3,20-dione:NADP+ delta4-oxidoreductase

  Catalysed by CYP11A1, HSD3B1, HSD3B2, SRD5A1 and 2 moremitochondrial matrix, cytosolOne of 2 routes

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

  Catalysed by SULT2B1, SULT1A3, STS, SLC25A35 and 1 morecytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• K(+)Reach from here →
  1. Sterol O-Acyltransferase
  2. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  3. K(+)(in) + L-cysteine(out) + 3 Na(+)(out) + H(+)(out) = K(+)(out) + L-cysteine(in) + 3 Na(+)(in) + H(+)(in)

  Catalysed by SOAT2, SOAT1, NAGS, SLC1A1endoplasmic reticulum, mitochondrial matrix, inner side of the membrane, outer side of the membraneOne of 2 routes

• Cys-tRNA(Cys)Reach from here →
  1. Sterol O-Acyltransferase
  2. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  3. L-Cysteine:tRNA(Cys) ligase (AMP-forming)

  Catalysed by SOAT2, SOAT1, NAGS, CARS1endoplasmic reticulum, mitochondrial matrix, cytosol

• Gly-tRNA(Gly)Reach from here →
  1. Sterol O-Acyltransferase
  2. glycine N-acyltransferase (N-arachidonoylglycine)
  3. glycine:tRNA(Gly) ligase (AMP-forming)

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

• Asn-tRNA(Asn)Reach from here →
  1. Sterol O-Acyltransferase
  2. N-acetylglutamate synthase (N-acetyl-L-asparagine)
  3. L-Asparagine:tRNA(Asn) ligase (AMP-forming)

  Catalysed by SOAT2, SOAT1, NAGS, NARS1endoplasmic reticulum, mitochondrial matrix, cytosol

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

  Catalysed by SULT2B1, SULT1A3, STS, SLC26A6cytosol, extracellular spaceOne of 16 routes

• phosphocholineReach 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 morecytosolOne of 4 routes

• glycocholateReach from here →
  1. Sterol O-Acyltransferase
  2. propanoyl-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

• cholateReach from here →
  1. Sterol O-Acyltransferase
  2. propanoyl-CoA C-acyltransferase
  3. choloyl-CoA hydrolase

  Catalysed by SOAT2, SOAT1, ACAA1, SCP2 and 2 moreendoplasmic reticulum, peroxisome, cytosolOne of 2 routes

• hydrogen sulfideReach from here →
  1. Sterol O-Acyltransferase
  2. N-acetylglutamate synthase (N-acetyl-L-cysteine)
  3. L-cysteine hydrogen-sulfide-lyase (deaminating

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

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

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

  Catalysed by SULT2B1, SULT1A3, STS, SLC25A14 and 1 morecytosol, inner side of the membrane, outer side of the membraneOne of 14 routes