Record Information
Version1.0
Creation date2010-04-08 22:10:37 UTC
Update date2018-05-29 01:04:10 UTC
Primary IDFDB013269
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCholesterol
DescriptionConstituent either free or as esters, of fish liver oils, lard, dairy fats, egg yolk and bran About 20?25% of total daily cholesterol production occurs in the liver; other sites of high synthesis rates include the intestines, adrenal glands and reproductive organs. Synthesis within the body starts with one molecule of acetyl CoA and one molecule of acetoacetyl-CoA, which are dehydrated to form 3-hydroxy-3-methylglutaryl CoA (HMG-CoA). This molecule is then reduced to mevalonate by the enzyme HMG-CoA reductase. This step is an irreversible step in cholesterol synthesis and is the site of action for the statins (HMG-CoA Reductase Inhibitors).; Cholesterol is a lipidic, waxy steroid found in the cell membranes and transported in the blood plasma of all animals. It is an essential component of mammalian cell membranes where it is required to establish proper membrane permeability and fluidity. In addition, cholesterol is an important precursor molecule for the biosynthesis of bile acids, steroid hormones, and several fat soluble vitamins. Cholesterol is the principal sterol synthesized by animals, but small quantities are synthesized in other eukaryotes, such as plants and fungi. It is almost completely absent among prokaryotes, which include bacteria.; 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; Given the well-recognized role of cholesterol in cardiovascular disease, it is surprising that some studies have shown an inverse correlation between cholesterol levels and mortality in subjects over 50 years of age?an 11% increase overall and 14% increase in CVD mortality per 1 mg/dL per year drop in cholesterol levels. In the Framingham Heart Study, the researchers attributed this phenomenon to the fact that people with severe chronic diseases or cancer tend to have below-normal cholesterol levels. This explanation is not supported by the Vorarlberg Health Monitoring and Promotion Programme, in which men of all ages and women over 50 with very low cholesterol were increasingly likely to die of cancer, liver diseases, and mental diseases. This result indicates that the low cholesterol effect occurs even among younger respondents, contradicting the previous assessment among cohorts of older people that this is a proxy or marker for frailty occurring with age.; Mevalonate is then converted to 3-isopentenyl pyrophosphate in three reactions which require ATP. This molecule is decarboxylated to isopentenyl pyrophosphate, which is a key metabolite for various biological reactions. Three molecules of isopentenyl pyrophosphate condense to form farnesyl pyrophosphate through the action of geranyl transferase. Two molecules of farnesyl pyrophosphate then condense to form squalene by the action of squalene synthase in the endoplasmic reticulum. Oxidosqualene cyclase then cyclizes squalene to form lanosterol. Finally, lanosterol is then converted to cholesterol.; Within cells, cholesterol is the precursor molecule in several biochemical pathways. In the liver, cholesterol is converted to bile, which is then stored in the gallbladder. Bile contains bile salts, which solubilize fats in the digestive tract and aid in the intestinal absorption of fat molecules as well as the fat soluble vitamins, Vitamin A, Vitamin D, Vitamin E and Vitamin K. Cholesterol is an important precursor molecule for the synthesis of Vitamin D and the steroid hormones, including the adrenal gland hormones cortisol and aldosterone as well as the sex hormones progesterone, estrogens, and testosterone and their derivatives.
CAS Number57-88-5
Structure
Thumb
Synonyms
SynonymSource
(-)-cholesterolbiospider
(+)-ent-cholesterolbiospider
(20bFH)-cholest-5-en-3b-olbiospider
(3β)-Cholest-5-en-3-olbiospider
(3b)-cholest-5-en-3-olbiospider
(3beta)-Cholest-5-en-3-olbiospider
(3H)-Cholesterolbiospider
«delta»5-Cholesten-3-β-olbiospider
1zhybiospider
20-epi-cholesterolbiospider
20-iso-cholesterolbiospider
20bFH-cholest-5-en-3b-olbiospider
3-beta-Hydroxycholest-5-enebiospider
3β-Hydroxycholest-5-enebiospider
3beta-Hydroxy-5-cholestenebiospider
3beta-Hydroxycholest-5-enebiospider
5-Cholesten-3β-olbiospider
5-Cholesten-3B-olbiospider
5-Cholesten-3beta-olbiospider
5, 6-Cholesten-3β-olbiospider
5,6-Cholesten-3β-olbiospider
5:6-Cholesten-3-olbiospider
5:6-Cholesten-3β-olbiospider
5:6-Cholesten-3beta-olbiospider
Cholest-5-en-3-beta-olbiospider
Cholest-5-en-3-olbiospider
Cholest-5-en-3-ol (3β)-biospider
Cholest-5-en-3-ol (3beta)-biospider
Cholest-5-en-3-ol (3beta)-, labeled with tritiumbiospider
Cholest-5-en-3-ol, (3β)-biospider
Cholest-5-en-3-ol, (3beta)-biospider
Cholest-5-en-3β-olbiospider
cholest-5-en-3b-olbiospider
cholest-5-en-3beta-olbiospider
Cholesterindb_source
Cholesterinebiospider
Cholesterinumbiospider
Cholesterinum Dps (D3-C1000)biospider
Cholesterinum Dps 4ch-30chbiospider
Cholesterinum-Injeel Forte Liq (6d,12d,30d,200d/1.1ml)biospider
Cholesterol (JP15/NF)biospider
Cholesterol (TN)biospider
Cholesterol [usan:jan]biospider
Cholesterol base hbiospider
Cholesterol, BAN, USANdb_source
Cholesterolumbiospider
Cholesteryl alcoholbiospider
Cholestrinbiospider
Cholestrolbiospider
CLRbiospider
Cordulanbiospider
Dastarbiospider
delta(sup 5)-Cholesten-3-beta-olbiospider
Delta5-Cholesten-3beta-olbiospider
Dusolinebiospider
Dusoranbiospider
Dytholbiospider
Epicholesterinbiospider
Epicholesterolbiospider
Fancol CHbiospider
Hydrocerinbiospider
Kathrobiospider
Lanolbiospider
Lidinitbiospider
Lidinitebiospider
Liquid crystal CN/9biospider
Nimco cholesterol base hbiospider
Nimco cholesterol base No. 712biospider
NSC 8798db_source
Phospholipon & cholesterolbiospider
Provitamin d (van)biospider
Soya phospholipon & Cholesterol (2:1 molar ratio)biospider
Super hartolanbiospider
Synthechol(r)biospider
SyntheChol(R) NS0 Supplementbiospider
Synthetic cholesterolbiospider
Tegolanbiospider
Tegolan (van)biospider
Wool alcohols b. pbiospider
Wool alcohols b. p.biospider
Predicted Properties
PropertyValueSource
Water Solubility2.8e-05 g/LALOGPS
logP7.02ALOGPS
logP7.11ChemAxon
logS-7.1ALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity120.62 m³·mol⁻¹ChemAxon
Polarizability50.18 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC27H46O
IUPAC name2,15-dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol
InChI IdentifierInChI=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
InChI KeyHVYWMOMLDIMFJA-UHFFFAOYSA-N
Isomeric SMILESCC(C)CCCC(C)C1CCC2C3CC=C4CC(O)CCC4(C)C3CCC12C
Average Molecular Weight386.6535
Monoisotopic Molecular Weight386.354866094
Classification
DescriptionThis compound belongs to the class of organic compounds known as cholesterols and derivatives. These are compounds containing a 3-hydroxylated cholestane core.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassCholestane steroids
Direct ParentCholesterols and derivatives
Alternative Parents
Substituents
  • Cholesterol-skeleton
  • Cholesterol
  • Hydroxysteroid
  • 3-hydroxysteroid
  • 3-hydroxy-delta-5-steroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 83.87%; H 11.99%; O 4.14%DFC
Melting PointMp 148.5° (anhyd.)DFC
Boiling PointNot Available
Experimental Water Solubility9.5e-05 mg/mL at 30 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
Charge0
Optical Rotation[a]D -31.12 (Et2O)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05i3-1109000000-8cd386b595bd5151c5a2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0009000000-91a2d07a2ae578ce1331JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05p9-3139000000-fefcd46ea3ac49633e6cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0c00-5159000000-84415da5c4b1353f88d7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-57deba99fbfb399fdaa9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0009000000-92b195d86bf5a087667fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ldi-2009000000-59339acd74eacce981fdJSpectraViewer
ChemSpider ID9200676
ChEMBL IDCHEMBL1867358
KEGG Compound IDC00187
Pubchem Compound ID11025495
Pubchem Substance IDNot Available
ChEBI ID16113
Phenol-Explorer IDNot Available
DrugBank IDDB04540
HMDB IDHMDB00067
CRC / DFC (Dictionary of Food Compounds) IDHKC02-A:HQO24-G
EAFUS IDNot Available
Dr. Duke IDCHOLESTEROL
BIGG ID34183
KNApSAcK IDC00003648
HET ID1LRI
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDCholesterol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
Enzymes
NameGene NameUniProt ID
Lysosomal acid lipase/cholesteryl ester hydrolaseLIPAP38571
Apolipoprotein A-IAPOA1P02647
Sulfotransferase family cytosolic 2B member 1SULT2B1O00204
7-dehydrocholesterol reductaseDHCR7Q9UBM7
Sterol O-acyltransferase 1SOAT1P35610
Phosphatidylcholine-sterol acyltransferaseLCATP04180
Sterol O-acyltransferase 2SOAT2O75908
Nuclear receptor ROR-alphaRORAP35398
Pathways
NameSMPDB LinkKEGG Link
Bile Acid BiosynthesisSMP00035 map00120
Steroid BiosynthesisSMP00023 map00100
SteroidogenesisSMP00130 map00140
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.