cholesterol

Three steps

• (7Z)-octadecenoyl-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

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

  Catalysed by CYP11A1, CYP17A1cytosolOne of 2 routes

• acetylcholineReach 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. Acetyl-CoA:choline O-acetyltransferase

  Catalysed by LCAT, ENPP2, GDPD3, GDPD1 and 1 morecytosolOne of 3 routes

• pyruvateReach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. L-cysteine hydrogen-sulfide-lyase (deaminating

  Catalysed by CH25H, MOCOS, CTHcytosolOne of 6 routes

• arachidonoyl-CoAReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + cholesterol = cholesteryl (5Z,8Z,11Z,14Z)-eicosatetraenoate + CoA
  2. sterol esterase (Cholesteryl Arachidonate)
  3. Arachidonate:CoA ligase (AMP-forming)

  Catalysed by SOAT2, SOAT1, CEL, LIPA and 8 morelysosome, cytosolOne of 4 routes

• palmitoyl-CoAReach from here →
  1. cholesterol + hexadecanoyl-CoA = cholesteryl hexadecanoate + CoA
  2. Steryl-ester acylhydrolase
  3. Palmitate:CoA ligase (AMP-forming)

  Catalysed by SOAT1, CEL, LIPA, SLC27A2 and 7 morelysosome, cytosolOne of 4 routes

• oleoyl-CoAReach from here →
  1. cholesterol + (9Z)-octadecenoyl-CoA = cholesteryl (9Z-octadecenoate) + CoA
  2. Steryl-ester acylhydrolase
  3. long-chain-fatty-acid-CoA ligase (oleate)

  Catalysed by SOAT2, SOAT1, CEL, LIPA and 8 morelysosome, cytosolOne of 4 routes

• (S)-malateReach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. (R)-malate + A = oxaloacetate + AH2
  3. transport of malate and OAA (cytosol to mitochondria)

  Catalysed by CH25H, D2HGDHmitochondrial matrix, cytosolOne of 9 routes

• L-leucineReach 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 leucine (cytosol to extracellular)

  Catalysed by CH25H, MOCOS, SLC7A9, SLC3A1extracellular space, cytosolOne of 3 routes

• 12(S)-HPETEReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + cholesterol = cholesteryl (5Z,8Z,11Z,14Z)-eicosatetraenoate + CoA
  2. sterol esterase (Cholesteryl Arachidonate)
  3. arachidonate:oxygen 12-oxidoreductase

  Catalysed by SOAT2, SOAT1, CEL, LIPA and 1 morelysosome, cytosolOne of 4 routes

• 15(S)-HPETEReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + cholesterol = cholesteryl (5Z,8Z,11Z,14Z)-eicosatetraenoate + CoA
  2. sterol esterase (Cholesteryl Arachidonate)
  3. arachidonate:oxygen 15-oxidoreductase

  Catalysed by SOAT2, SOAT1, CEL, LIPA and 2 morelysosome, cytosolOne of 4 routes

• 5(S)-HPETEReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + cholesterol = cholesteryl (5Z,8Z,11Z,14Z)-eicosatetraenoate + CoA
  2. sterol esterase (Cholesteryl Arachidonate)
  3. Arachidonate:oxygen 5-oxidoreductase

  Catalysed by SOAT2, SOAT1, CEL, LIPA and 1 morelysosome, cytosol

• all-trans-3-hydroxyretinolReach 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 + 2 reduced [adrenodoxin] + O2 + 2 H(+) = all-trans-3-hydroxyretinol + 2 oxidized [adrenodoxin] + H2O

  Catalysed by CH25H, RETSAT, CYP27C1

• CHEBI:15699Reach 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 homoserine (cytosol to extracellular)

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

• formateReach 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 + NAD(+) + H2O = formate + NADH + 2 H(+)

  Catalysed by CH25H, KDM1A, KDM1B, ALDH9A1

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

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

• 16alpha-hydroxyprogesteroneReach from here →
  1. 6 reduced [adrenodoxin] + cholesterol + 3 O2 + 6 H(+) = 4-methylpentanal + pregnenolone + 6 oxidized [adrenodoxin] + 4 H2O
  2. Pregnenolone:NAD+ 3-oxidoreductase
  3. progesterone + reduced [NADPH--hemoprotein reductase] + O2 = 16alpha-hydroxyprogesterone + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CYP11A1, HSD3B1, HSD3B2, CYP3A4 and 1 morecytosol

• 1-acylglycerone 3-phosphateReach 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:glycerone-phosphate O-acyltransferase

  Catalysed by GBA1, GBA2, ASAH1, ACER2 and 3 moreGolgi apparatus, cytosol

• a 1-O-alkyl-sn-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. 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
  3. a 1-O-alkyl-sn-glycero-3-phosphocholine + H2O = a 1-O-alkyl-sn-glycerol + phosphocholine + H(+)

  Catalysed by LCAT, ENPP6

• beta-D-glucoseReach 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 1-epimerase

  Catalysed by GBA1, GBA2, GALMcytosolOne of 2 routes

• CHEBI:15971Reach 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 histidine (cytosol to extracellular)

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

• CHEBI:15978Reach 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-Glycero-3-phosphocholine glycerophosphohydrolase

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

• methanethiolReach 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. methanethiol + O2 + H2O = hydrogen sulfide + formaldehyde + H2O2 + H(+)

  Catalysed by CH25H, KDM1A, KDM1B, SELENBP1

• phosphatidylethanolamineReach 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-acyl-sn-glycero-3-phosphoethanolamine O-acyltransferase

  Catalysed by GBA1, GBA2, ASAH1, ACER2 and 7 moreGolgi apparatus, cytosolOne of 2 routes

• 1,2-diacyl-sn-glycero-3-phosphocholine(1+)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:1-acyl-sn-glycero-3-phosphocholine O-acyltransferase

  Catalysed by GBA1, GBA2, ASAH1, ACER2 and 6 moreGolgi apparatus, cytosolOne of 2 routes

• CHEBI:16174Reach 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. dATP:D-glucose 6-phosphotransferase

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

• D-glucono-1,5-lactoneReach 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 + NAD(+) = D-glucono-1,5-lactone + NADH + H(+)

  Catalysed by GBA1, GBA2, H6PDOne of 2 routes

• L-cystineReach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. thioredoxin-disulfide reductase (NADPH) (cystine)

  Catalysed by CH25H, MOCOS, TXNRD1, TXNRD3 and 1 morecytosolOne of 4 routes

• 11-cis-retinolReach 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 11-cis-trans-isomerase

  Catalysed by CH25H, RETSATcytosolOne of 2 routes

• cob(II)alaminReach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. 2 cob(II)alamin + A + 2 H2O + 2 H(+) = 2 aquacob(III)alamin + AH2

  Catalysed by CH25H, AIFM1, PYROXD1, MTRR

• phosphatidic acidReach 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-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase

  Catalysed by GBA1, GBA2, ASAH1, ACER2 and 11 moreGolgi apparatus, mitochondrial matrixOne of 12 routes

• L-citrullineReach 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 citrulline and cysteine (cytosol to extracellular)

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

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

  Catalysed by CH25H, AIFM1, PYROXD1, DIO1 and 1 moreOne of 22 routes

• L-valineReach 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 valine (cytosol to extracellular)

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

• CHEBI:16436Reach 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. ceramide cholinephosphotransferase (CDP-choline)

  Catalysed by GBA1, GBA2, SGMS1, SGMS2Golgi apparatus, endoplasmic reticulum

• L-arginineReach 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 arginine and cysteine (cytosol to extracellular)

  Catalysed by CH25H, MOCOS, SLC7A6extracellular space, cytosolOne of 5 routes

• nitric oxideReach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. 2 nitrite + AH2 + 2 H(+) = 2 nitric oxide + A + 2 H2O

  Catalysed by CH25H, AIFM1, PYROXD1, SUOX

• protein polypeptide chainReach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. PROTEIN_BS

  Catalysed by CH25H, MOCOScytosol

• quinolinic acidReach from here →
  1. cholesterol + 3'-phosphoadenylyl sulfate = cholesterol sulfate + adenosine 3',5'-bisphosphate + H(+)
  2. Cholesterol-sulfate sulfohydrolase
  3. Transport of Quinolinic Acid

  Catalysed by SULT2B1, SULT1C2, STS, SLC22A6cytosol, extracellular spaceOne of 2 routes

• 3'-deoxy-3',4'-didehydro-CTPReach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. CTP + AH2 + S-adenosyl-L-methionine = 3'-deoxy-3',4'-didehydro-CTP + 5'-deoxyadenosine + L-methionine + A + H2O + H(+)

  Catalysed by CH25H, AIFM1, PYROXD1, RSAD2

• 8-hydroxydodecanoateReach from here →
  1. 1-(beta-D-galactosyl)-N-dodecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-galactoside + N-dodecanoylsphing-4-enine
  2. H2O[c] + N-dodecanoylsphing-4-enine[c] = lauric acid[c] + sphingosine[c]
  3. dodecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 8-hydroxydodecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by GBA1, GBA2, NAAA, CYP4Z1cytosol

• 10-hydroxydodecanoateReach from here →
  1. 1-(beta-D-galactosyl)-N-dodecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-galactoside + N-dodecanoylsphing-4-enine
  2. H2O[c] + N-dodecanoylsphing-4-enine[c] = lauric acid[c] + sphingosine[c]
  3. dodecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 10-hydroxydodecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by GBA1, GBA2, NAAA, CYP4Z1cytosol

• 9-hydroxydodecanoateReach from here →
  1. 1-(beta-D-galactosyl)-N-dodecanoylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-galactoside + N-dodecanoylsphing-4-enine
  2. H2O[c] + N-dodecanoylsphing-4-enine[c] = lauric acid[c] + sphingosine[c]
  3. dodecanoate + reduced [NADPH--hemoprotein reductase] + O2 = 9-hydroxydodecanoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by GBA1, GBA2, NAAA, CYP4Z1cytosol

• (S)-2-hydroxyglutarateReach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)
  3. (S)-2-hydroxyglutarate + A = 2-oxoglutarate + AH2

  Catalysed by CH25H, AIFM1, PYROXD1, L2HGDH

• CHEBI:16856Reach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. Mo-molybdopterin + L-cysteine + AH2 = thio-Mo-molybdopterin + L-alanine + A + H2O
  3. cystine to cysteine conversion

  Catalysed by CH25H, MOCOScytosolOne of 3 routes

• CHEBI:16857Reach 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 threonine (cytosol to extracellular)

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

• psychosineReach 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. UDP-alpha-D-galactose:sphingosine 1-beta-galactosyltransferase

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

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

  Catalysed by CYP11A1, HSD3B1, HSD3B2, CYP21A2cytosolOne of 3 routes

• 1-acyl-sn-glycerol 3-phosphateReach 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. 1-acylglycerol-3P-LD-TG1 pool (liver tissue) formation

  Catalysed by LCAT, ENPP2, GDPD3, GDPD1cytosolOne of 9 routes

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

  Catalysed by SULT2B1, SULT1C2, STS, SLC26A6cytosol, extracellular space