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Record Information
Version1.0
Creation Date2016-07-13 19:40:50 UTC
Update Date2016-07-20 20:48:52 UTC
LmdbLMDB00030
Secondary Accession NumbersNone
Metabolite Identification
Common NameCholesterol
DescriptionCholesterol 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
Synonyms
ValueSource
(3beta,14beta,17alpha)-Cholest-5-en-3-olChEBI
Cholest-5-en-3beta-olChEBI
CholesterinChEBI
(3b,14b,17a)-Cholest-5-en-3-olGenerator
(3β,14β,17α)-cholest-5-en-3-olGenerator
Cholest-5-en-3b-olGenerator
Cholest-5-en-3β-olGenerator
(3β)-Cholest-5-en-3-olHMDB
(3beta)-Cholest-5-en-3-olHMDB
3β-Hydroxycholest-5-eneHMDB
3beta-Hydroxycholest-5-eneHMDB
5:6-Cholesten-3β-olHMDB
5:6-Cholesten-3beta-olHMDB
(-)-CholesterolHMDB
CholesterineHMDB
Cholesterol base HHMDB
Cholesteryl alcoholHMDB
CholestrinHMDB
CholestrolHMDB
CordulanHMDB
DastarHMDB
DusolineHMDB
DusoranHMDB
DytholHMDB
Fancol CHHMDB
HydrocerinHMDB
KathroHMDB
LanolHMDB
Super hartolanHMDB
TegolanHMDB
CholesterolHMDB
Chemical FormulaC27H46O
Average Molecular Weight386.6535
Monoisotopic Molecular Weight386.354866094
IUPAC Name(1S,2R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol
Traditional Namecholest-5-en-3-ol
CAS Registry Number57-88-5
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 KeyHVYWMOMLDIMFJA-FNOPAARDSA-N
Chemical Taxonomy
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
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • 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
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Polarizability50.7 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-004i-3911000000-52f5261007adc218f8f8View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052b-2932000000-1667c83d002043a59fffView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000l-9527000000-5529a262047f5369c9c1View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0mkr-2954000000-60e7d1f5973e4de33decView in MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-014i-1009000000-e82b8e23dedb45ce70e6View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-056v-2900000000-04687c9f19ff52ba4654View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05i3-1109000000-8cd386b595bd5151c5a2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-3104900000-698223f49da0b0c1cf81View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0009000000-dccd68f70545aeac4fabView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05p9-3149000000-7f25daf2b709c7e0d177View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0c00-6269000000-5333d0216e01a3e43367View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-dc853b29b9e884bbb03bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0009000000-09d9608700564a6fef78View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ldi-1009000000-96f6e67651380e1c959eView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0a4l-7922000000-36e8a5e1a77d2e71d1d1View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Bile acid
  • Follicular Fluid
  • Milk
  • Plasma
  • Rumen
  • Serum
  • Skim milk
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
Bile acidDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
Follicular FluidDetected and Quantified687.954 uMNot AvailableBovine
    • C. Lutwak-Mann. N...
details
MilkDetected and Quantified140 mg/kgNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableOvine
    • Park, Y. W; Juáre...
details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine
    • Kurt J. Boudonck,...
details
MilkDetected and Quantified341.8+/-15.6 mg/100g fatNot AvailableCaprine
    • Park, Y. W; Juáre...
details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
PlasmaDetected and Quantified2010 +/- 50 uMNot AvailablePorcine details
PlasmaDetected and Quantified1815.838 +/- 142.505 uMNot AvailableBovine
    • Abdullah BAŞOĞLU,...
details
PlasmaDetected and Quantified2317.320 +/- 236.387 uMNot AvailableBovine
    • Abdullah BAŞOĞLU,...
details
PlasmaDetected and Quantified3341.493 +/- 370.616 uMNot AvailableBovine
    • Abdullah BAŞOĞLU,...
details
PlasmaDetected and Quantified2000-15800 uMNot AvailablePorcine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableBovine
    • Trabi M, Keller M...
details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableEquine
    • E. E. Escalona, J...
details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
PlasmaDetected and Quantified1940-2330 uMNot AvailablePorcine
    • Jianxiang XU,Deng...
details
RumenDetected but not QuantifiedNot ApplicableNot AvailableBovine
    • Hanne Christine B...
details
SerumDetected and Quantified1380.0470-1382.633 uMNot AvailableOvine
    • Edson Ferraz Evar...
details
SerumDetected and Quantified2940 +/- 430 uMNot AvailablePorcine details
SerumDetected and Quantified3790 +/- 420 uMNot AvailablePorcine details
SerumDetected and Quantified4138071.943 uMNot AvailableBovine
    • M.J. Abarghuei, Y...
details
SerumDetected and Quantified4189797.842 uMNot AvailableBovine
    • M.J. Abarghuei, Y...
details
SerumDetected and Quantified5431219.425 uMNot AvailableBovine
    • M.J. Abarghuei, Y...
details
SerumDetected and Quantified5560534.173 uMNot AvailableBovine
    • M.J. Abarghuei, Y...
details
SerumDetected and Quantified2910 uMNot AvailableBovine details
SerumDetected and Quantified3290 uMNot AvailableBovine details
SerumDetected and Quantified1600 uMNot AvailablePorcine
    • Barbara U. Metzle...
details
SerumDetected and Quantified1700 uMNot AvailablePorcine
    • Barbara U. Metzle...
details
SerumDetected and Quantified1600 uMNot AvailablePorcine
    • Barbara U. Metzle...
details
SerumDetected and Quantified2000 uMNot AvailablePorcine
    • Barbara U. Metzle...
details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected and Quantified775.888 uMNot AvailableBovine
    • Arthur K. Anderso...
details
Skim milkDetected and Quantified20 mg/kgNot AvailableBovine details
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00003648
BiGG IDNot Available
BioCyc IDCHOLESTEROL
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCholesterol
Chemspider IDNot Available
ChEBI ID16113
PubChem Compound ID5997
Kegg Compound IDC00187
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available