cholesterol

Two steps

• cholineReach 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(+)

  Catalysed by LCAT, ENPP2, GDPD3, GDPD1

• betaine aldehydeReach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. choline + A = betaine aldehyde + AH2

  Catalysed by CH25H, CHDH

• hexadecanoic acidReach from here →
  1. cholesterol + hexadecanoyl-CoA = cholesteryl hexadecanoate + CoA
  2. Steryl-ester acylhydrolase

  Catalysed by SOAT1, CEL, LIPAlysosomeOne of 3 routes

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

  Catalysed by SULT2B1, SULT1C2, STScytosolOne of 4 routes

• oxaloacetateReach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. (R)-malate + A = oxaloacetate + AH2

  Catalysed by CH25H, D2HGDH

• 1-phosphatidyl-1D-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

  Catalysed by OSBP, PTPRQ, INPPL1, CTDSPL2 and 10 moreinner side of the membrane, outer side of the membrane, cytosolOne of 2 routes

• formaldehydeReach 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

  Catalysed by CH25H, KDM1A, KDM1BOne of 3 routes

• sn-glycerol 3-phosphocholineReach 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(+)

  Catalysed by LCAT, PLA2G6, LYPLA1, LYPLA2 and 14 moreOne of 6 routes

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

  Catalysed by CYP11A1, HSD3B1, HSD3B2cytosolOne of 2 routes

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

  Catalysed by CH25H, RETSAT

• linoleic acidReach from here →
  1. (9Z,12Z)-octadecadienoyl-CoA + cholesterol = cholesteryl (9Z,12Z)-octadecadienoate + CoA
  2. Steryl-ester acylhydrolase

  Catalysed by SOAT1, CEL, LIPAlysosomeOne of 2 routes

• AH2Reach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. A + NADH + H(+) = AH2 + NAD(+)

  Catalysed by CH25H, AIFM1, PYROXD1One of 19 routes

• 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

  Catalysed by CH25H, MOCOS

• a sphingomyelinReach 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

  Catalysed by GBA1, GBA2, SGMS1, SGMS2Golgi apparatusOne of 8 routes

• a 1,2-diacyl-sn-glycerolReach 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

  Catalysed by GBA1, GBA2, SGMS1, SGMS2Golgi apparatusOne of 9 routes

• 7alpha-hydroxycholest-4-en-3-oneReach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. Cholest-5-Ene-3Beta, 7Alpha-Diol:NAD+ 3-Oxidoreductase Bile Acid Biosynthesis

  Catalysed by CH25H, HSD3B7endoplasmic reticulumOne of 5 routes

• dodecanoateReach 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]

  Catalysed by GBA1, GBA2, NAAAcytosolOne of 2 routes

• D-glucosyl-N-acylsphingosineReach 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. UDP-glucose:N-acylsphingosine D-glucosyltransferase

  Catalysed by GBA1, GBA2, UGCGcytosolOne of 2 routes

• a beta-D-galactosyl-(1<->1')-N-acylsphing-4-enineReach 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. an N-acylsphing-4-enine + UDP-alpha-D-galactose = a beta-D-galactosyl-(1<->1')-N-acylsphing-4-enine + UDP + H(+)

  Catalysed by GBA1, GBA2, UGT8One of 3 routes

• a beta-D-xylosyl-(1<->1')-N-acylsphing-4-enineReach 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-xylosyl-(1<->1')-N-acylsphing-4-enine + cholesterol = cholesteryl 3-beta-D-xyloside + an N-acylsphing-4-enine

  Catalysed by GBA1, GBA2, GBA3One of 3 routes

• beta-D-xylosyl-(1<->1')-N-(9Z-octadecenoyl)-sphing-4-enineReach from here →
  1. beta-D-glucosyl-N-(9Z-octadecenoyl)-sphing-4E-enine + cholesterol = N-(9Z-octadecenoyl)-sphing-4-enine + cholesteryl 3-beta-D-glucoside
  2. N-(9Z-octadecenoyl)-sphing-4-enine + UDP-alpha-D-xylose = beta-D-xylosyl-(1<->1')-N-(9Z-octadecenoyl)-sphing-4-enine + UDP + H(+)

  Catalysed by GBA1, GBA2, UGCG

• 1D-myo-inositol 1,4,5-trisphosphateReach from here →
  1. 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)
  2. a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol-4,5-bisphosphate) + H2O = 1D-myo-inositol 1,4,5-trisphosphate + a 1,2-diacyl-sn-glycerol + H(+)

  Catalysed by OSBP2, OSBPL2, PLCH2, PLCG2 and 11 moreinner side of the membrane, outer side of the membrane

• a beta-D-glucosyl-(1<->1')-N-acylsphing-4-enineReach 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

  Catalysed by GBA1, GBA2One of 3 routes

• octadecanoateReach from here →
  1. octadecanoyl-CoA + cholesterol = cholesteryl octadecanoate + CoA
  2. Steryl-ester acylhydrolase

  Catalysed by SOAT1, CEL, LIPAlysosomeOne of 3 routes

• octanoateReach from here →
  1. beta-D-glucosyl-N-octanoylsphing-4E-enine + cholesterol = N-octanoylsphing-4-enine + cholesteryl 3-beta-D-glucoside
  2. N-octanoylsphing-4-enine + H2O = octanoate + sphing-4-enine

  Catalysed by GBA1, ASAH1, ASAH2

• elaidic acidReach from here →
  1. beta-D-glucosyl-N-(9Z-octadecenoyl)-sphing-4E-enine + cholesterol = N-(9Z-octadecenoyl)-sphing-4-enine + cholesteryl 3-beta-D-glucoside
  2. H2O[g] + N-(9Z-octadecenoyl)-sphing-4-enine[g] = elaidate[g] + sphingosine[g]

  Catalysed by GBA1, GBA2, ACER3Golgi apparatus

• 1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholineReach 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. 1,2-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 LCAT, TAFAZZIN

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

  Catalysed by CYP11A1, CYP17A1cytosolOne of 3 routes

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

  Catalysed by SOAT2, SOAT1, CES1, LIPN and 2 moreOne of 2 routes

• phosphocholineReach 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-glycerol + phosphocholine + H(+)

  Catalysed by LCAT, SMPD2, ENPP6, ENPP7 and 1 more

• (9Z)-octadecenoateReach from here →
  1. cholesterol + (9Z)-octadecenoyl-CoA = cholesteryl (9Z-octadecenoate) + CoA
  2. Steryl-ester acylhydrolase

  Catalysed by SOAT2, SOAT1, CEL, LIPAlysosomeOne of 5 routes

• a 1-O-alkyl-sn-glycero-3-phosphocholineReach 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

  Catalysed by LCAT

• (15Z)-tetracosenoateReach from here →
  1. beta-D-glucosyl-(1<->1')-N-(15Z-tetracosenoyl)-sphing-4-enine + cholesterol = N-(15Z-tetracosenoyl)-sphing-4-enine + cholesteryl 3-beta-D-glucoside
  2. N-(15Z-tetracosenoyl)-sphing-4-enine + H2O = (15Z)-tetracosenoate + sphing-4-enine

  Catalysed by GBA1, ACER2, ACER1, ASAH2

• (5Z,8Z,11Z,14Z)-eicosatetraenoateReach from here →
  1. (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA + cholesterol = cholesteryl (5Z,8Z,11Z,14Z)-eicosatetraenoate + CoA
  2. sterol esterase (Cholesteryl Arachidonate)

  Catalysed by SOAT2, SOAT1, CEL, LIPAlysosome

• fatty 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. N-Acylsphingosine amidohydrolase

  Catalysed by GBA1, GBA2, ASAH1lysosome

• 7alpha,25-dihydroxycholesterolReach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. cytochrome P450 (25-hydroxycholesterol)

  Catalysed by CH25H, CYP7B1endoplasmic reticulumOne of 2 routes

• (24S)-7alpha-dihydroxycholesterolReach from here →
  1. cholesterol + reduced [NADPH--hemoprotein reductase] + O2 = 7alpha-hydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)
  2. 7alpha-hydroxycholesterol + reduced [NADPH--hemoprotein reductase] + O2 = (24S)-7alpha-dihydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+)

  Catalysed by CYP7A1, CYP46A1One of 4 routes

• 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

  Catalysed by GBA1, GBA2

• a 1,2-diacyl-sn-glycero-3-phospho-L-serineReach 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. a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol 4-phosphate)(out) + a 1,2-diacyl-sn-glycero-3-phospho-L-serine(in) = a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol 4-phosphate)(in) + a 1,2-diacyl-sn-glycero-3-phospho-L-serine(out)

  Catalysed by OSBP, OSBPL9, OSBPL11, OSBPL10 and 3 moreinner side of the membrane, outer side of the membraneOne of 2 routes

• 7,8-dihydrofolateReach 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(+)

  Catalysed by CH25H, MTO1

• 1-hexadecanoyl-sn-glycero-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(+)

  Catalysed by LCAT, ENPP2, GDPD3, GDPD1

• a 1,2-diacyl-sn-glycero-3-phosphocholineReach 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. a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol 4-phosphate)(out) + a 1,2-diacyl-sn-glycero-3-phosphocholine(in) = a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol 4-phosphate)(in) + a 1,2-diacyl-sn-glycero-3-phosphocholine(out)

  Catalysed by OSBP, OSBPL3inner side of the membrane, outer side of the membraneOne of 2 routes

• an N-acylsphing-4-enine 1-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. an N-acylsphing-4-enine + ATP = an N-acylsphing-4-enine 1-phosphate + ADP + H(+)

  Catalysed by GBA1, GBA2, AGK, CERK

• sphing-4-enineReach 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

  Catalysed by GBA1, GBA2, ASAH1, ACER2 and 2 moreGolgi apparatusOne of 14 routes

• a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol-5-phosphate)Reach from here →
  1. 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)
  2. a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol-4,5-bisphosphate) + H2O = a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol-5-phosphate) + phosphate

  Catalysed by OSBP2, OSBPL2, PIP4P1, PIP4P2inner side of the membrane, outer side of the membrane

• a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol)Reach 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. a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol 4-phosphate) + H2O = a 1,2-diacyl-sn-glycero-3-phospho-(1D-myo-inositol) + phosphate

  Catalysed by OSBP, SYNJ2, SYNJ1, SACM1L and 1 moreinner side of the membrane, outer side of the membrane

• an acyl-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

  Catalysed by GBA1, GBA2, ASAH1, ACER2 and 2 moreGolgi apparatusOne of 2 routes

• (5Z,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

  Catalysed by SOAT2, CEL, LIPAlysosomeOne of 3 routes

• a 2,3-dehydroacyl-CoAReach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. a 2,3-saturated acyl-CoA + A = a 2,3-dehydroacyl-CoA + AH2

  Catalysed by CH25H, ACAD10

• Fe(II)-heme aReach from here →
  1. cholesterol + AH2 + O2 = 25-hydroxycholesterol + A + H2O
  2. Fe(II)-heme o + 2 A + H2O = Fe(II)-heme a + 2 AH2

  Catalysed by CH25H, COX15