Human Metabolome Database Version 3.5

Showing metabocard for Cholesterol (HMDB00067)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:07:50 -0700
HMDB ID HMDB00067
Secondary Accession Numbers
  • HMDB00507
Metabolite Identification
Common Name Cholesterol
Description Cholesterol is a sterol (a combination steroid and alcohol) and a lipid found in the cell membranes of all body tissues, and transported in the blood plasma of all animals. The name originates from the Greek chole- (bile) and stereos (solid), and the chemical suffix -ol for an alcohol, as researchers first identified cholesterol (C27H45OH) in solid form in gallstones in 1784. Cholesterol is transported throughout the body via lipoprotein particles. The largest lipoproteins, which primarily transport fats from the intestinal mucosa to the liver, are called chylomicrons. They carry mostly triglyceride fats and cholesterol (that are from food and especially internal cholesterol secreted by the liver into the bile). In the liver, chylomicron particles give up triglycerides and some cholesterol, and are converted into low-density lipoprotein (LDL) particles, which carry triglycerides and cholesterol on to other body cells. In healthy individuals the LDL particles are large and relatively few in number. In contrast, large numbers of small LDL particles are strongly associated with promoting atheromatous disease within the arteries. (Lack of information on LDL particle number and size is one of the major problems of conventional lipid tests.). In conditions with elevated concentrations of oxidized LDL particles, especially small LDL particles, cholesterol promotes atheroma plaque deposits in the walls of arteries, a condition known as atherosclerosis, which is a major contributor to coronary heart disease and other forms of cardiovascular disease. (In contrast, HDL particles have been the only identified mechanism by which cholesterol can be removed from atheroma. Increased concentrations of large HDL particles, not total HDL particles, correlate with lower rates of atheroma progressions, even regression.). There is a world-wide trend to believe that lower total cholesterol levels tend to correlate with lower atherosclerosis event rates (though many studies refute this idea). Due to this reason, cholesterol has become a very large focus for scientific researchers trying to determine the proper amount of cholesterol needed in a healthy diet. However, the primary association of atherosclerosis with cholesterol has always been specifically with cholesterol transport patterns, not total cholesterol per se. For example, total cholesterol can be low, yet made up primarily of small LDL and small HDL particles and atheroma growth rates are high. In contrast, however, if LDL particle number is low (mostly large particles) and a large percentage of the HDL particles are large (HDL is actively reverse transporting cholesterol), then atheroma growth rates are usually low, even negative, for any given total cholesterol concentration. These effects are further complicated by the relative concentration of asymmetric dimethylarginin (ADMA) in the endothelium, since ADMA down-regulates production of nitric oxide, a relaxant of the endothelium. Thus, high levels of ADMA, associated with high oxidized levels of LDL pose a heightened risk factor for vascular disease. -- Wikipedia.
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (+)-ent-Cholesterol
  2. (-)-Cholesterol
  3. (20bFH)-cholest-5-en-3b-ol
  4. (3b)-cholest-5-en-3-ol
  5. (3beta)-Cholest-5-en-3-ol
  6. 20-Epi-cholesterol
  7. 20-Iso-cholesterol
  8. 20bFH-cholest-5-en-3b-ol
  9. 3beta-Hydroxycholest-5-ene
  10. 5-Cholesten-3B-ol
  11. 5-Cholesten-3beta-ol
  12. 5:6-Cholesten-3-ol
  13. 5:6-Cholesten-3beta-ol
  14. Cholest-5-en-3-ol
  15. Cholest-5-en-3b-ol
  16. Cholest-5-en-3beta-ol
  17. Cholesterin
  18. Cholesterine
  19. Cholesterol
  20. Cholesterol base H
  21. Cholesteryl alcohol
  22. Cholestrin
  23. Cholestrol
  24. Cordulan
  25. Dastar
  26. Dusoline
  27. Dusoran
  28. Dythol
  29. Epicholesterin
  30. Epicholesterol
  31. Fancol CH
  32. Hydrocerin
  33. Kathro
  34. Lanol
  35. Liquid crystal CN/9
  36. Nimco cholesterol base H
  37. Nimco cholesterol base No. 712
  38. Super hartolan
  39. Tegolan
Chemical Formula C27H46O
Average Molecular Weight 386.6535
Monoisotopic Molecular Weight 386.354866094
IUPAC Name (1S,2R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol
Traditional IUPAC Name (1S,2R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol
CAS Registry Number 57-88-5
SMILES [H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2CC(O)CC[C@]12C
InChI Identifier InChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25,28H,6-8,10-17H2,1-5H3/t19-,21?,22+,23-,24+,25+,26+,27-/m1/s1
InChI Key HVYWMOMLDIMFJA-FNOPAARDSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Steroids and Steroid Derivatives
Sub Class Cholesterols and Derivatives
Other Descriptors
  • Aliphatic Homopolycyclic Compounds
  • a 3-β-hydroxysterol(Cyc)
Substituents
  • 3 Hydroxy Steroid
  • Bicyclohexane
  • Cyclic Alcohol
  • Cyclohexane
  • Cyclohexene
  • Secondary Alcohol
  • Sesterterpene
Direct Parent Cholesterols and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Component of Bile acid biosynthesis
  • Component of C21-Steroid hormone metabolism
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
  • Lysosome
  • Endoplasmic reticulum
  • Golgi apparatus
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 148 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 9.5e-05 mg/mL Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 2.790E-05 g/L ALOGPS
LogP 7.02 ALOGPS
LogP 7.11 ChemAxon
LogS -7.14 ALOGPS
pKa (strongest acidic) 18.2 ChemAxon
pKa (strongest basic) -1.4 ChemAxon
Hydrogen Acceptor Count 1 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 20.23 A2 ChemAxon
Rotatable Bond Count 5 ChemAxon
Refractivity 120.62 ChemAxon
Polarizability 50.7 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Gas-MS Spectrum
1H NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
  • Lysosome
  • Endoplasmic reticulum
  • Golgi apparatus
Biofluid Locations
  • Bile
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Saliva
Tissue Location
  • All Tissues
  • Prostate
Pathways
Name SMPDB Link KEGG Link
Steroidogenesis SMP00130 map00140 Link_out
Bile Acid Biosynthesis SMP00035 map00120 Link_out
Steroid Biosynthesis SMP00023 map00100 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Bile Detected and Quantified
11500(10000-13000) uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
4141.0 (3105.0-5176.0) uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
5700.0 (4500.0-6700.0) uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
3.76 +/- 0.098 uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
0.82 +/- 0.009 uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
33.0 +/- 79.0 uM Adult (>18 years old) Male Normal
Blood Detected and Quantified
32.0 +/- 82.0 uM Adult (>18 years old) Female Normal
Blood Detected and Quantified
5000.0 (4500.0-5500.0) uM Adult (>18 years old) Both Normal
  • Geigy Scient...
Cerebrospinal Fluid (CSF) Detected and Quantified
4.30 (3.90-4.70) uM Adult (>18 years old) Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
8.32 (7.88-8.76) uM Adult (>18 years old) Both Normal
Saliva Detected and Quantified
<1.00 uM Adult (>18 years old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Bile Detected and Quantified 13100 (10900-15300) uM Adult (>18 years old) Both Gallstone disease
Bile Detected and Quantified 13900 (13100-14700) uM Adult (>18 years old) Both Cholesterol stones
Bile Detected and Quantified 15110 (9860-20360) uM Adult (>18 years old) Both Gastric cancer
Bile Detected and Quantified 16700 (14100-19300) uM Adult (>18 years old) Both Gallstone disease
Blood Detected and Quantified 5700.0 (5200.0-6200.0) uM Adult (>18 years old) Both Comment Hypercholesterolemia
Blood Detected and Quantified 9317.8 (7764.8-10870.8) uM Children (1-13 year old) Both Cholesteryl ester storage disease
Blood Detected and Quantified 8000.0 (6000.0-10000.0) uM Children (1-13 year old) Both Cystinosis
Blood Detected and Quantified 3200.0 (2600.0-4100.0) uM Adult (>18 years old) Both Acute myelogenous leukemia (AML)
Blood Detected and Quantified 400 uM Infant (0-1 year old) Both Smith-Lemli-Opitz syndrome
Cerebrospinal Fluid (CSF) Detected and Quantified 1.1 uM Infant (0-1 year old) Both Smith-Lemli-Opitz syndrome
Cerebrospinal Fluid (CSF) Detected and Quantified 10.9 +/- 2.7 uM Adult (>18 years old) Both Multiple Sclerosis
Associated Disorders and Diseases
Disease References
Gallbladder disease
  • Miettinen TE, Kesaniemi YA, Gylling H, Jarvinen H, Silvennoinen E, Miettinen TA: Noncholesterol sterols in bile and stones of patients with cholesterol and pigment stones. Hepatology. 1996 Feb;23(2):274-80. Pubmed: 8591852 Link_out
  • Mizuno S, Tazuma S, Kajiyama G: Stabilization of biliary lipid particles by ursodeoxycholic acid. Prolonged nucleation time in human gallbladder bile. Dig Dis Sci. 1993 Apr;38(4):684-93. Pubmed: 8462368 Link_out
      Cholelithiasis
      • Miettinen TE, Kesaniemi YA, Gylling H, Jarvinen H, Silvennoinen E, Miettinen TA: Noncholesterol sterols in bile and stones of patients with cholesterol and pigment stones. Hepatology. 1996 Feb;23(2):274-80. Pubmed: 8591852 Link_out
          Stomach cancer
          • Higashijima H, Ichimiya H, Nakano T, Yamashita H, Kuroki S, Satoh H, Chijiiwa K, Tanaka M: Deconjugation of bilirubin accelerates coprecipitation of cholesterol, fatty acids, and mucin in human bile--in vitro study. J Gastroenterol. 1996 Dec;31(6):828-35. Pubmed: 9027647 Link_out
              Multiple sclerosis
              • Leoni V, Lutjohann D, Masterman T: Levels of 7-oxocholesterol in cerebrospinal fluid are more than one thousand times lower than reported in multiple sclerosis. J Lipid Res. 2005 Feb;46(2):191-5. Epub 2004 Dec 1. Pubmed: 15576852 Link_out
                  Acute myelogenous leukemia
                  • Tatidis L, Vitols S, Gruber A, Paul C, Axelson M: Cholesterol catabolism in patients with acute myelogenous leukemia and hypocholesterolemia: suppressed levels of a circulating marker for bile acid synthesis. Cancer Lett. 2001 Sep 20;170(2):169-75. Pubmed: 11463495 Link_out
                      Hypercholesterolemia
                      • [No authors listed]Report of the National Cholesterol Education Program Expert Panel on Detection, Evaluation, and Treatment of High Blood Cholesterol in Adults. The Expert Panel. Arch Intern Med. 1988 Jan;148(1):36-69. Pubmed: 3422148 Link_out
                          Cholesteryl ester storage disease
                              Cystinosis
                                  Associated OMIM IDs
                                  DrugBank ID DB04540 Link_out
                                  DrugBank Metabolite ID Not Available
                                  Phenol Explorer Compound ID Not Available
                                  Phenol Explorer Metabolite ID Not Available
                                  FoodDB ID FDB013269
                                  KNApSAcK ID C00003648 Link_out
                                  Chemspider ID 9200676 Link_out
                                  KEGG Compound ID C00187 Link_out
                                  BioCyc ID CHOLESTEROL Link_out
                                  BiGG ID 34183 Link_out
                                  Wikipedia Link Cholesterol Link_out
                                  NuGOwiki Link HMDB00067 Link_out
                                  Metagene Link HMDB00067 Link_out
                                  METLIN ID 163 Link_out
                                  PubChem Compound 11025495 Link_out
                                  PDB ID 1LRI Link_out
                                  ChEBI ID 1307929 Link_out
                                  References
                                  Synthesis Reference Zhu, Yongming; Qin, Liena; Liu, Rui. Simple method for synthesis cholesterol from Diosgenin. Faming Zhuanli Shenqing Gongkai Shuomingshu (2006), 9 pp.
                                  Material Safety Data Sheet (MSDS) Download (PDF)
                                  General References
                                  1. Bjorkhem I, Heverin M, Leoni V, Meaney S, Diczfalusy U: Oxysterols and Alzheimer's disease. Acta Neurol Scand Suppl. 2006;185:43-9. Pubmed: 16866910 Link_out
                                  2. Ellis D, Lloyd C, Becker DJ, Forrest KY, Orchard TJ: The changing course of diabetic nephropathy: low-density lipoprotein cholesterol and blood pressure correlate with regression of proteinuria. Am J Kidney Dis. 1996 Jun;27(6):809-18. Pubmed: 8651245 Link_out
                                  3. Gil'miiarova FN, Pervova IuV, Radomskaia VM, Gergel' NI, Tarasova SV: [Levels of unified metabolites and thyroid hormones in blood and oral fluid of children with minimal brain dysfunction] Biomed Khim. 2004 Mar-Apr;50(2):204-10. Pubmed: 15179829 Link_out
                                  4. Thelen KM, Falkai P, Bayer TA, Lutjohann D: Cholesterol synthesis rate in human hippocampus declines with aging. Neurosci Lett. 2006 Jul 31;403(1-2):15-9. Epub 2006 May 15. Pubmed: 16701946 Link_out
                                  5. Schillaci G, Pirro M, Ronti T, Gemelli F, Pucci G, Innocente S, Porcellati C, Mannarino E: Prognostic impact of prolonged ventricular repolarization in hypertension. Arch Intern Med. 2006 Apr 24;166(8):909-13. Pubmed: 16636218 Link_out
                                  6. Higashijima H, Ichimiya H, Nakano T, Yamashita H, Kuroki S, Satoh H, Chijiiwa K, Tanaka M: Deconjugation of bilirubin accelerates coprecipitation of cholesterol, fatty acids, and mucin in human bile--in vitro study. J Gastroenterol. 1996 Dec;31(6):828-35. Pubmed: 9027647 Link_out
                                  7. Proksch GJ, Bonderman DP: Use of a cholesterol-rich bovine lipoprotein to enhance cholesterol concentrations in the preparation of serum control materials. Clin Chem. 1976 Aug;22(8):1302-5. Pubmed: 985740 Link_out
                                  8. van Rooij A, Nijenhuis AA, Wijburg FA, Schutgens RB: Highly increased CSF concentrations of cholesterol precursors in Smith-Lemli-Opitz syndrome. J Inherit Metab Dis. 1997 Aug;20(4):578-80. Pubmed: 9266395 Link_out
                                  9. Sanchez E, Fernandez-D'Pool J: [Liver function in patients exposed to a toluene in a hydrocarbon processing plant] Invest Clin. 1996 Dec;37(4):255-70. Pubmed: 9004852 Link_out
                                  10. Mizuno S, Tazuma S, Kajiyama G: Stabilization of biliary lipid particles by ursodeoxycholic acid. Prolonged nucleation time in human gallbladder bile. Dig Dis Sci. 1993 Apr;38(4):684-93. Pubmed: 8462368 Link_out
                                  11. Bookman ID, Pham J, Guindi M, Heathcote EJ: Distinguishing nonalcoholic steatohepatitis from fatty liver: serum-free fatty acids, insulin resistance, and serum lipoproteins. Liver Int. 2006 Jun;26(5):566-71. Pubmed: 16762001 Link_out
                                  12. Nigg C, Gutzwiller F: [Cholesterol: blood level and control by Swiss physicians] Schweiz Med Wochenschr. 1995 Feb 25;125(8):355-60. Pubmed: 7709184 Link_out
                                  13. Winocour PH, Durrington PN, Bhatnagar D, Ishola M, Mackness M, Arrol S: Influence of early diabetic nephropathy on very low density lipoprotein (VLDL), intermediate density lipoprotein (IDL), and low density lipoprotein (LDL) composition. Atherosclerosis. 1991 Jul;89(1):49-57. Pubmed: 1772471 Link_out
                                  14. Hoffmann G, Gibson KM, Brandt IK, Bader PI, Wappner RS, Sweetman L: Mevalonic aciduria--an inborn error of cholesterol and nonsterol isoprene biosynthesis. N Engl J Med. 1986 Jun 19;314(25):1610-4. Pubmed: 3012338 Link_out
                                  15. Markuszewski L, Rosiak M, Golanski J, Rysz J, Spychalska M, Watala C: Reduced blood platelet sensitivity to aspirin in coronary artery disease: are dyslipidaemia and inflammatory states possible factors predisposing to sub-optimal platelet response to aspirin? Basic Clin Pharmacol Toxicol. 2006 May;98(5):503-9. Pubmed: 16635110 Link_out
                                  16. Miettinen TE, Kesaniemi YA, Gylling H, Jarvinen H, Silvennoinen E, Miettinen TA: Noncholesterol sterols in bile and stones of patients with cholesterol and pigment stones. Hepatology. 1996 Feb;23(2):274-80. Pubmed: 8591852 Link_out
                                  17. Leoni V, Lutjohann D, Masterman T: Levels of 7-oxocholesterol in cerebrospinal fluid are more than one thousand times lower than reported in multiple sclerosis. J Lipid Res. 2005 Feb;46(2):191-5. Epub 2004 Dec 1. Pubmed: 15576852 Link_out
                                  18. D'Amico G, Gentile MG: Effect of dietary manipulation on the lipid abnormalities and urinary protein loss in nephrotic patients. Miner Electrolyte Metab. 1992;18(2-5):203-6. Pubmed: 1465059 Link_out
                                  19. Pak CH, Oleneva VA, Agadzhanov SA: [Dietetic aspects of preventing urolithiasis in patients with gout and uric acid diathesis] Vopr Pitan. 1985 Jan-Feb;(1):21-4. Pubmed: 3885567 Link_out
                                  20. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411 Link_out

                                  Enzymes
                                  Name: Phosphatidylcholine-sterol acyltransferase
                                  Reactions: Not Available
                                  Gene Name: LCAT
                                  Uniprot ID: P04180 Link_out
                                  Protein Sequence: FASTA
                                  Gene Sequence: FASTA
                                  Name: Lysosomal acid lipase/cholesteryl ester hydrolase
                                  Reactions:
                                  Cholesterol ester + Water unknown Cholesterol + Fatty acid details
                                  Gene Name: LIPA
                                  Uniprot ID: P38571 Link_out
                                  Protein Sequence: FASTA
                                  Gene Sequence: FASTA
                                  Name: Bile salt-activated lipase
                                  Reactions:
                                  Cholesterol ester + Water unknown Cholesterol + Fatty acid details
                                  Gene Name: CEL
                                  Uniprot ID: P19835 Link_out
                                  Protein Sequence: FASTA
                                  Gene Sequence: FASTA
                                  Name: Sulfotransferase family cytosolic 2B member 1
                                  Reactions:
                                  Cholesterol + Phosphoadenosine phosphosulfate unknown Cholesterol sulfate + Adenosine 3',5'-diphosphate details
                                  Gene Name: SULT2B1
                                  Uniprot ID: O00204 Link_out
                                  Protein Sequence: FASTA
                                  Gene Sequence: FASTA
                                  Name: Steryl-sulfatase
                                  Reactions:
                                  Cholesterol + Oat gum unknown Cholesterol sulfate + Water details
                                  Gene Name: STS
                                  Uniprot ID: P08842 Link_out
                                  Protein Sequence: FASTA
                                  Gene Sequence: FASTA
                                  Name: Sterol O-acyltransferase 2
                                  Reactions:
                                  Acyl-CoA + Cholesterol unknown Coenzyme A + cholesterol ester details
                                  Gene Name: SOAT2
                                  Uniprot ID: O75908 Link_out
                                  Protein Sequence: FASTA
                                  Gene Sequence: FASTA
                                  Name: Cholesterol 7-alpha-monooxygenase
                                  Reactions:
                                  Cholesterol + NADPH + Oxygen unknown 7a-Hydroxycholesterol + NADP + Water details
                                  Cholesterol + Oxygen + NADPH + Hydrogen Ion unknown 7a-Hydroxycholesterol + NADP + Water details
                                  Gene Name: CYP7A1
                                  Uniprot ID: P22680 Link_out
                                  Protein Sequence: FASTA
                                  Gene Sequence: FASTA
                                  Name: Sterol O-acyltransferase 1
                                  Reactions:
                                  Acyl-CoA + Cholesterol unknown Coenzyme A + cholesterol ester details
                                  Gene Name: SOAT1
                                  Uniprot ID: P35610 Link_out
                                  Protein Sequence: FASTA
                                  Gene Sequence: FASTA
                                  Name: 7-dehydrocholesterol reductase
                                  Reactions:
                                  Cholesterol + NADP unknown 7-Dehydrocholesterol + NADPH details
                                  Cholesterol + NAD unknown 7-Dehydrocholesterol + NADH + Hydrogen Ion details
                                  Cholesterol + NADP unknown 7-Dehydrocholesterol + NADPH + Hydrogen Ion details
                                  Gene Name: DHCR7
                                  Uniprot ID: Q9UBM7 Link_out
                                  Protein Sequence: FASTA
                                  Gene Sequence: FASTA
                                  Name: Cholesterol side-chain cleavage enzyme, mitochondrial
                                  Reactions:
                                  Cholesterol + reduced adrenal ferredoxin + Oxygen unknown Pregnenolone + 4-Methylpentanal + oxidized adrenal ferredoxin + Water details
                                  Cholesterol + Oxygen + Hydrogen Ion + Reduced adrenal ferredoxin unknown 20alpha-Hydroxycholesterol + Water + Oxidized adrenal ferredoxin details
                                  Cholesterol + Oxygen + Reduced adrenal ferredoxin + Hydrogen Ion unknown 22b-Hydroxycholesterol + Water + Oxidized adrenal ferredoxin details
                                  Gene Name: CYP11A1
                                  Uniprot ID: P05108 Link_out
                                  Protein Sequence: FASTA
                                  Gene Sequence: FASTA
                                  Name: Sterol 26-hydroxylase, mitochondrial
                                  Reactions:
                                  Cholesterol + Oxygen + NADPH + Hydrogen Ion unknown 27-Hydroxycholesterol + NADP + Water details
                                  Gene Name: CYP27A1
                                  Uniprot ID: Q02318 Link_out
                                  Protein Sequence: FASTA
                                  Gene Sequence: FASTA
                                  Name: ATP-binding cassette sub-family A member 1
                                  Reactions: Not Available
                                  Gene Name: ABCA1
                                  Uniprot ID: O95477 Link_out
                                  Protein Sequence: FASTA
                                  Gene Sequence: FASTA
                                  Name: Apolipoprotein A-I
                                  Reactions: Not Available
                                  Gene Name: APOA1
                                  Uniprot ID: P02647 Link_out
                                  Protein Sequence: FASTA
                                  Gene Sequence: FASTA
                                  Name: Delta(24)-sterol reductase
                                  Reactions:
                                  Cholesterol + NADP unknown Desmosterol + Hydrogen Ion + NADPH details
                                  Gene Name: DHCR24
                                  Uniprot ID: Q15392 Link_out
                                  Protein Sequence: FASTA
                                  Gene Sequence: FASTA
                                  Name: Nuclear receptor ROR-alpha
                                  Reactions: Not Available
                                  Gene Name: RORA
                                  Uniprot ID: P35398 Link_out
                                  Protein Sequence: FASTA
                                  Gene Sequence: FASTA
                                  Name: Cholesterol 25-hydroxylase
                                  Reactions:
                                  Cholesterol + AH(2) + Oxygen unknown 25-Hydroxycholesterol + A + Water details
                                  Cholesterol + Reduced acceptor + Oxygen unknown 25-Hydroxycholesterol + Acceptor + Water details
                                  Gene Name: CH25H
                                  Uniprot ID: O95992 Link_out
                                  Protein Sequence: FASTA
                                  Gene Sequence: FASTA
                                  Name: Cholesterol 24-hydroxylase
                                  Reactions:
                                  Cholesterol + NADPH + Oxygen unknown 24-Hydroxycholesterol + NADP + Water details
                                  Gene Name: CYP46A1
                                  Uniprot ID: Q9Y6A2 Link_out
                                  Protein Sequence: FASTA
                                  Gene Sequence: FASTA
                                  Transporters
                                  Name: Multidrug resistance protein 1
                                  Reactions: Not Available
                                  Gene Name: ABCB1
                                  Uniprot ID: P08183 Link_out
                                  Protein Sequence: FASTA
                                  Gene Sequence: FASTA
                                  Name: ATP-binding cassette sub-family G member 2
                                  Reactions: Not Available
                                  Gene Name: ABCG2
                                  Uniprot ID: Q9UNQ0 Link_out
                                  Protein Sequence: FASTA
                                  Gene Sequence: FASTA