| 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 |
|
| 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 |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- (+)-ent-Cholesterol
- (-)-Cholesterol
- (20bFH)-cholest-5-en-3b-ol
- (3b)-cholest-5-en-3-ol
- (3beta)-Cholest-5-en-3-ol
- 20-Epi-cholesterol
- 20-Iso-cholesterol
- 20bFH-cholest-5-en-3b-ol
- 3beta-Hydroxycholest-5-ene
- 5-Cholesten-3B-ol
- 5-Cholesten-3beta-ol
- 5:6-Cholesten-3-ol
- 5:6-Cholesten-3beta-ol
- Cholest-5-en-3-ol
- Cholest-5-en-3b-ol
- Cholest-5-en-3beta-ol
- Cholesterin
- Cholesterine
- Cholesterol
- Cholesterol base H
- Cholesteryl alcohol
- Cholestrin
- Cholestrol
- Cordulan
- Dastar
- Dusoline
- Dusoran
- Dythol
- Epicholesterin
- Epicholesterol
- Fancol CH
- Hydrocerin
- Kathro
- Lanol
- Liquid crystal CN/9
- Nimco cholesterol base H
- Nimco cholesterol base No. 712
- Super hartolan
- 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 |
|
| 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 |
|
| Spectra |
|---|
|
|
| Biological Properties |
|---|
| Cellular Locations |
- Cytoplasm
- Extracellular
- Membrane
- Mitochondria
- Lysosome
- Endoplasmic reticulum
- Golgi apparatus
|
| Biofluid Locations |
- Bile
- Blood
- Cerebrospinal Fluid (CSF)
- Saliva
|
| Tissue Location |
|
| Pathways |
|
| Normal Concentrations |
|---|
|
| Bile |
Detected and Quantified |
|
11500(10000-13000) uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
5700.0 (4500.0-6700.0) uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
3.76 +/- 0.098 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
0.82 +/- 0.009 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
33.0 +/- 79.0 uM |
Adult (>18 years old) |
Male |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
32.0 +/- 82.0 uM |
Adult (>18 years old) |
Female |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
5000.0 (4500.0-5500.0) uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
4.30 (3.90-4.70) uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
8.32 (7.88-8.76) uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Saliva |
Detected and Quantified |
|
<1.00 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
|
| Abnormal Concentrations |
|---|
|
| Bile |
Detected and Quantified |
|
13100 (10900-15300) uM |
Adult (>18 years old) |
Both |
Gallstone disease |
Not Available |
| Bile |
Detected and Quantified |
|
13900 (13100-14700) uM |
Adult (>18 years old) |
Both |
Cholesterol stones |
Not Available |
| Bile |
Detected and Quantified |
|
15110 (9860-20360) uM |
Adult (>18 years old) |
Both |
Gastric cancer |
Not Available |
| Bile |
Detected and Quantified |
|
16700 (14100-19300) uM |
Adult (>18 years old) |
Both |
Gallstone disease |
Not Available |
| Blood |
Detected and Quantified |
|
5700.0 (5200.0-6200.0) uM |
Adult (>18 years old) |
Both |
Hypercholesterolemia |
Borderline-high blood cholesterol
|
| Blood |
Detected and Quantified |
|
4141.0 (3105.0-5176.0) uM |
Adult (>18 years old) |
Both |
Cholesteryl ester storage disease |
Not Available |
| Blood |
Detected and Quantified |
|
9317.8 (7764.8-10870.8) uM |
Adult (>18 years old) |
Both |
Cholesteryl ester storage disease |
Not Available |
| Blood |
Detected and Quantified |
|
8000.0 (6000.0-10000.0) uM |
Adult (>18 years old) |
Both |
Cystinosis |
Not Available |
| Blood |
Detected and Quantified |
|
3200.0 (2600.0-4100.0) uM |
Adult (>18 years old) |
Both |
Acute myelogenous leukemia (AML) |
Not Available |
| Blood |
Detected and Quantified |
|
400 uM |
Infant (0-1 year old) |
Both |
Smith-Lemli-Opitz syndrome |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
1.1 uM |
Infant (0-1 year old) |
Both |
Smith-Lemli-Opitz syndrome |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
10.9 +/- 2.7 uM |
Adult (>18 years old) |
Both |
Multiple Sclerosis |
Not Available |
|
| 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
- 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
|
| 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
|
| 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
|
| 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
|
| 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
|
| 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
|
| Cholesteryl ester storage disease |
|---|
- http://www.metagene.de/program/d.prg?mp=CHOLESTERYL%20ESTER%20STORAGE%20DISEASE
|
| Cystinosis |
|---|
- http://www.metagene.de/program/d.prg?mp=CYSTINOSIS
|
|
| Associated OMIM IDs |
|
| External Links |
|---|
| DrugBank ID |
DB04540 |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB013269 |
| KNApSAcK ID |
C00003648 |
| Chemspider ID |
9200676 |
| KEGG Compound ID |
C00187 |
| BioCyc ID |
CHOLESTEROL |
| BiGG ID |
34183 |
| Wikipedia Link |
Cholesterol |
| NuGOwiki Link |
HMDB00067 |
| Metagene Link |
HMDB00067 |
| METLIN ID |
163 |
| PubChem Compound |
11025495 |
| PDB ID |
1LRI |
| ChEBI ID |
1307929 |
| 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 |
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- Nigg C, Gutzwiller F: [Cholesterol: blood level and control by Swiss physicians] Schweiz Med Wochenschr. 1995 Feb 25;125(8):355-60.
Pubmed: 7709184
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
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