cholesterol

Three steps

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

  Catalysed by SOAT1, CEL, LIPA, ALDH3A2lysosome

• L-isoleucineReach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. transport of cysteine and isoleucine (cytosol to extracellular)

  Catalysed by CH25H, MOCOS, SLC7A5extracellular space, cytosolOne of 4 routes

• CHEBI:17203Reach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. transport of cysteine and proline (cytosol to extracellular)

  Catalysed by CH25H, MOCOS, SLC7A5extracellular space, cytosolOne of 3 routes

• 17alpha-hydroxyprogesteroneReach from here →
  1. 6 reduced [adrenodoxin] + cholesterol + 3 O2 + 6 H(+) = 4-methylpentanal + pregnenolone + 6 oxidized [adrenodoxin] + 4 H2O
  2. cytochrome P450 (pregnenolone)
  3. 17alpha-Hydroxypregnenolone:NAD+ 3-oxidoreductase

  Catalysed by CYP11A1, CYP17A1, HSD3B1, HSD3B2cytosol, endoplasmic reticulumOne of 5 routes

• myo-inositolReach from here →
  1. 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)
  2. ATP:1-Phosphatidyl-1D-myo-inositol 4-phosphotransferase
  3. Phospholipase D

  Catalysed by OSBP, PTPRQ, INPPL1, CTDSPL2 and 11 moreinner side of the membrane, outer side of the membrane, cytosolOne of 4 routes

• 5'-deoxyadenosineReach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. N(6)-dimethylallyladenosine(37) in tRNA + (sulfur carrier)-SH + AH2 + 2 S-adenosyl-L-methionine = 2-methylsulfanyl-N(6)-dimethylallyladenosine(37) in tRNA + (sulfur carrier)-H + 5'-deoxyadenosine + L-methionine + A + S-adenosyl-L-homocysteine + 2 H(+)

  Catalysed by CH25H, AIFM1, PYROXD1, CDK5RAP1One of 4 routes

• sulfiteReach from here →
  1. cholesterol + 3'-phosphoadenylyl sulfate = cholesterol sulfate + adenosine 3',5'-bisphosphate + H(+)
  2. Cholesterol-sulfate sulfohydrolase
  3. sulfite(in) + sulfate(out) = sulfite(out) + sulfate(in)

  Catalysed by SULT2B1, SULT1C2, STS, SLC25A14 and 1 morecytosol, inner side of the membrane, outer side of the membraneOne of 2 routes

• a 2-acylglycerolReach from here →
  1. a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + an N-acylsphing-4-enine
  2. ceramide:phosphatidylcholine cholinephosphotransferase
  3. a 1,2-diacyl-sn-glycerol + H2O = a 2-acylglycerol + a fatty acid + H(+)

  Catalysed by GBA1, GBA2, SGMS1, SGMS2 and 3 moreGolgi apparatus

• a monoacylglycerolReach from here →
  1. an acyl-CoA + cholesterol = a cholesterol ester + CoA
  2. a cholesterol ester + H2O = cholesterol + a fatty acid + H(+)
  3. a monoacylglycerol + H2O = glycerol + a fatty acid + H(+)

  Catalysed by SOAT2, SOAT1, CES1, LIPN and 3 moreOne of 9 routes

• 1-(alk-1-enyl)-2-acyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + an N-acylsphing-4-enine
  2. acyl-CoA:sphingosine N-acyltransferase
  3. Acyl-CoA:1-alkenylglycerophosphoethanolamine O-acyltransferase

  Catalysed by GBA1, GBA2, ASAH1, ACER2 and 6 moreGolgi apparatus, cytosol

• 1-O-acyl-sn-glycero-3-phosphocholine(1+)Reach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. all-trans-13,14-dihydroretinol + A = all-trans-retinol + AH2
  3. Lecithin Retinol Acyltransferase

  Catalysed by CH25H, RETSAT, LRATcytosolOne of 3 routes

• hexadecanalReach from here →
  1. cholesterol + hexadecanoyl-CoA = cholesteryl hexadecanoate + CoA
  2. Steryl-ester acylhydrolase
  3. 2 H+[c] + NADH[c] + palmitate[c] = H2O[c] + hexadecanal[c] + NAD+[c]

  Catalysed by SOAT1, CEL, LIPA, ALDH3B1 and 2 morelysosome, cytosolOne of 3 routes

• all-trans-retinyl hexadecanoateReach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. all-trans-13,14-dihydroretinol + A = all-trans-retinol + AH2
  3. all-trans-retinol + hexadecanoyl-CoA = all-trans-retinyl hexadecanoate + CoA

  Catalysed by CH25H, RETSAT, DGAT1, PNPLA4 and 3 moreOne of 5 routes

• 3,3',5'-triiodo-L-thyronine sulfateReach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. 3,3',5'-triiodo-L-thyronine sulfate + iodide + A + H(+) = L-thyroxine sulfate + AH2

  Catalysed by CH25H, AIFM1, PYROXD1, DIO1

• 3,3'-diiodo-L-thyronineReach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. 3,3'-diiodo-L-thyronine + iodide + A + H(+) = 3,3',5-triiodo-L-thyronine + AH2

  Catalysed by CH25H, AIFM1, PYROXD1, DIO1 and 1 moreOne of 2 routes

• 3,3'-diiodo-L-thyronine sulfateReach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. 3,3'-diiodo-L-thyronine sulfate + iodide + A + H(+) = 3,3',5-triiodo-L-thyronine sulfate + AH2

  Catalysed by CH25H, AIFM1, PYROXD1, DIO1One of 4 routes

• lactoseReach from here →
  1. a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + an N-acylsphing-4-enine
  2. cholesteryl 3-beta-D-glucoside + H2O = cholesterol + D-glucose
  3. D-glucose + UDP-alpha-D-galactose = lactose + UDP + H(+)

  Catalysed by GBA1, GBA2, B4GALT2, B4GALT1

• CHEBI:17724Reach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. N(6),N(6)-dimethyl-L-lysyl(4)-[histone H3] + 2 A + 2 H2O = L-lysyl(4)-[histone H3] + 2 formaldehyde + 2 AH2
  3. dimethylglycine dehydrogenase (formaldehyde)

  Catalysed by CH25H, KDM1A, KDM1B, PDPR and 1 morecytosol

• desmosterolReach from here →
  1. cholesterol + (9Z)-octadecenoyl-CoA = cholesteryl (9Z-octadecenoate) + CoA
  2. Steryl-ester acylhydrolase
  3. 3-hydroxyacyl-CoA dehydrogenase (desmosterol)

  Catalysed by SOAT2, SOAT1, CEL, LIPAlysosome, nucleus

• glycine betaineReach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. choline + A = betaine aldehyde + AH2
  3. p-cumic alcohol:NAD+ oxidoreductase

  Catalysed by CH25H, CHDH, ALDH7A1cytosolOne of 4 routes

• glycerolReach from here →
  1. 1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + cholesterol = cholesteryl (5Z,8Z,11Z,14Z)-eicosatetraenoate + 1-hexadecanoyl-sn-glycero-3-phosphocholine
  2. 1-hexadecanoyl-sn-glycero-3-phosphocholine + H2O = sn-glycerol 3-phosphocholine + hexadecanoate + H(+)
  3. sn-glycerol 3-phosphocholine + H2O = phosphocholine + glycerol + H(+)

  Catalysed by LCAT, PLA2G6, LYPLA1, LYPLA2 and 15 more

• CHEBI:17808Reach from here →
  1. a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + an N-acylsphing-4-enine
  2. cholesteryl 3-beta-D-glucoside + H2O = cholesterol + D-glucose
  3. ITP:D-glucose 6-phosphotransferase

  Catalysed by GBA1, GBA2, HK1, HK2 and 2 morecytosol

• a triacylglycerolReach from here →
  1. a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + an N-acylsphing-4-enine
  2. acyl-CoA:sphingosine N-acyltransferase
  3. acyl-CoA:1,2-diacyl-sn-glycerol O-acyltransferase

  Catalysed by GBA1, GBA2, ASAH1, ACER2 and 7 moreGolgi apparatus, cytosolOne of 3 routes

• CHEBI:17895Reach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. transport of cysteine and tyrosine (cytosol to extracellular)

  Catalysed by CH25H, MOCOS, SLC7A5extracellular space, cytosolOne of 4 routes

• all-trans-retinalReach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. all-trans-13,14-dihydroretinol + A = all-trans-retinol + AH2
  3. retinol: NADP+ oxidoreductase

  Catalysed by CH25H, RETSAT, DHRS3, RDH10 and 4 morecytosolOne of 6 routes

• D-glucitolReach from here →
  1. a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + an N-acylsphing-4-enine
  2. cholesteryl 3-beta-D-glucoside + H2O = cholesterol + D-glucose
  3. Aldehyde Reductase

  Catalysed by GBA1, GBA2cytosolOne of 3 routes

• a beta-D-Gal-(1->4)-beta-D-Glc-(1<->1)-Cer(d18:1(4E))Reach from here →
  1. a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + an N-acylsphing-4-enine
  2. a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + an N-acylsphing-4-enine
  3. a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + UDP-alpha-D-galactose = a beta-D-Gal-(1->4)-beta-D-Glc-(1<->1)-Cer(d18:1(4E)) + UDP + H(+)

  Catalysed by GBA1, GBA2, B4GALT5, B4GALT6One of 5 routes

• fumaric acidReach from here →
  1. cholesterol + 3'-phosphoadenylyl sulfate = cholesterol sulfate + adenosine 3',5'-bisphosphate + H(+)
  2. Cholesterol-sulfate sulfohydrolase
  3. transport of fumarate and sulfate (cytosol to mitochondria)

  Catalysed by SULT2B1, SULT1C2, STS, SLC25A10cytosol, mitochondrial matrixOne of 2 routes

• CHEBI:18019Reach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. transport of cysteine and lysine (cytosol to extracellular)

  Catalysed by CH25H, MOCOS, SLC7A6extracellular space, cytosolOne of 2 routes

• a diacylglycerolReach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. all-trans-13,14-dihydroretinol + A = all-trans-retinol + AH2
  3. a triacylglycerol + all-trans-retinol = an all-trans-retinyl ester + a diacylglycerol

  Catalysed by CH25H, RETSAT, PNPLA4, PNPLA2

• L-glutamineReach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. transport of cysteine and glutamine (cytosol to extracellular)

  Catalysed by CH25H, MOCOS, SLC3A2, SLC7A5 and 1 moreextracellular space, cytosolOne of 4 routes

• CHEBI:18132Reach from here →
  1. 1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine + cholesterol = cholesteryl (5Z,8Z,11Z,14Z)-eicosatetraenoate + 1-hexadecanoyl-sn-glycero-3-phosphocholine
  2. 1-hexadecanoyl-sn-glycero-3-phosphocholine + H2O = 1-hexadecanoyl-sn-glycero-3-phosphate + choline + H(+)
  3. ATP:choline phosphotransferase

  Catalysed by LCAT, ENPP2, GDPD3, GDPD1 and 2 morecytosolOne of 6 routes

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

  Catalysed by SOAT2, CEL, LIPA, ALOX5lysosome

• 3',5'-diiodo-L-thyronineReach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. 3',5'-diiodo-L-thyronine + iodide + A + H(+) = 3,3',5'-triiodo-L-thyronine + AH2

  Catalysed by CH25H, AIFM1, PYROXD1, DIO3

• 5-(3,3-dimethylguanidino)-2-oxopentanoateReach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. (R)-malate + A = oxaloacetate + AH2
  3. N(omega),N(omega)-dimethyl-L-arginine + oxaloacetate = 5-(3,3-dimethylguanidino)-2-oxopentanoate + L-aspartate

  Catalysed by CH25H, D2HGDH, AGXT2

• (6R)-5,10-methylenetetrahydrofolic acidReach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. N(6),N(6)-dimethyl-L-lysyl(4)-[histone H3] + 2 A + 2 H2O = L-lysyl(4)-[histone H3] + 2 formaldehyde + 2 AH2
  3. formaldehyde to 5,10-methylene-THF conversion

  Catalysed by CH25H, KDM1A, KDM1Bcytosol

• 5,6,7,8-tetrahydrofolic acidReach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. uridine(34) in tRNA + 5,10-methylenetetrahydrofolate + taurine + GTP + A + H2O = 5-taurinomethyluridine(34) in tRNA + 7,8-dihydrofolate + GDP + AH2 + phosphate + H(+)
  3. 5,6,7,8-tetrahydrofolate:NAD+ oxidoreductase

  Catalysed by CH25H, MTO1, DHFR, DHFR2cytosolOne of 3 routes

• S-disulfanyl-L-cysteineReach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. S-sulfanyl-L-cysteine + L-cysteine = S-disulfanyl-L-cysteine + L-alanine

  Catalysed by CH25H, MOCOS, CARS2

• O-[(5Z),(8Z),(11Z),(14Z)-eicosatetraenoyl]-beta-D-glucuronateReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + cholesterol = cholesteryl (5Z,8Z,11Z,14Z)-eicosatetraenoate + CoA
  2. sterol esterase (Cholesteryl Arachidonate)
  3. (5Z,8Z,11Z,14Z)-eicosatetraenoate + UDP-alpha-D-glucuronate = O-[(5Z),(8Z),(11Z),(14Z)-eicosatetraenoyl]-beta-D-glucuronate + UDP

  Catalysed by SOAT2, SOAT1, CEL, LIPA and 6 morelysosome

• 3-iodothyronamineReach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. 3-iodothyronamine + iodide + A + H(+) = 3,5-diiodothyronamine + AH2

  Catalysed by CH25H, AIFM1, PYROXD1, DIO1 and 1 moreOne of 2 routes

• (11Z)-docosenoyl-CoA(4-)Reach from here →
  1. a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + an N-acylsphing-4-enine
  2. acyl-CoA:sphingosine N-acyltransferase
  3. acyl-CoA pool formation and breakdown

  Catalysed by GBA1, GBA2, ASAH1, ACER2 and 2 moreGolgi apparatus, cytosol

• 3-iodo-L-thyronineReach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. 3-iodo-L-thyronine + iodide + A + H(+) = 3,5-diiodo-L-thyronine + AH2

  Catalysed by CH25H, AIFM1, PYROXD1, DIO1 and 1 moreOne of 2 routes

• (7Z)-tetradecenoyl-CoAReach from here →
  1. a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-glucoside + an N-acylsphing-4-enine
  2. acyl-CoA:sphingosine N-acyltransferase
  3. acyl-CoA pool formation and breakdown

  Catalysed by GBA1, GBA2, ASAH1, ACER2 and 2 moreGolgi apparatus, cytosol

• 3'-iodo-L-thyronineReach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. 3'-iodo-L-thyronine + iodide + A + H(+) = 3',5'-diiodo-L-thyronine + AH2

  Catalysed by CH25H, AIFM1, PYROXD1, DIO1 and 1 moreOne of 2 routes

• L-thyronineReach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. L-thyronine + iodide + A + H(+) = 3-iodo-L-thyronine + AH2

  Catalysed by CH25H, AIFM1, PYROXD1, DIO3

• thyronamineReach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. thyronamine + iodide + A + H(+) = 3-iodothyronamine + AH2

  Catalysed by CH25H, AIFM1, PYROXD1, DIO3

• 3'-iodothyronamineReach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. 3'-iodothyronamine + iodide + A + H(+) = 3',5'-diiodothyronamine + AH2

  Catalysed by CH25H, AIFM1, PYROXD1, DIO1 and 1 moreOne of 2 routes

• 3,3'-diiodothyronamineReach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. 3,3'-diiodothyronamine + iodide + A + H(+) = 3,3',5'-triiodothyronamine + AH2

  Catalysed by CH25H, AIFM1, PYROXD1, DIO1 and 1 moreOne of 2 routes

• 3',5'-diiodothyronamineReach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. 3',5'-diiodothyronamine + iodide + A + H(+) = 3,3',5'-triiodothyronamine + AH2

  Catalysed by CH25H, AIFM1, PYROXD1, DIO3

• 3,3',5'-triiodothyronamineReach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. 3,3',5'-triiodothyronamine + iodide + A + H(+) = 3,3',5,5'-tetraiodothyronamine + AH2

  Catalysed by CH25H, AIFM1, PYROXD1, DIO3