Livestock Metabolome Database: Showing metabocard for Cholesterol (LMDB00030)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:40:50 UTC

Update Date

2016-07-20 20:48:52 UTC

Lmdb

LMDB00030

Secondary Accession Numbers

None

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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(3beta,14beta,17alpha)-Cholest-5-en-3-ol	ChEBI
Cholest-5-en-3beta-ol	ChEBI
Cholesterin	ChEBI
(3b,14b,17a)-Cholest-5-en-3-ol	Generator
(3Β,14β,17α)-cholest-5-en-3-ol	Generator
Cholest-5-en-3b-ol	Generator
Cholest-5-en-3β-ol	Generator
(3Β)-cholest-5-en-3-ol	HMDB
(3beta)-Cholest-5-en-3-ol	HMDB
3Β-hydroxycholest-5-ene	HMDB
3beta-Hydroxycholest-5-ene	HMDB
5:6-Cholesten-3β-ol	HMDB
5:6-Cholesten-3beta-ol	HMDB
(-)-Cholesterol	HMDB
Cholesterine	HMDB
Cholesterol base H	HMDB
Cholesteryl alcohol	HMDB
Cholestrin	HMDB
Cholestrol	HMDB
Cordulan	HMDB
Dastar	HMDB
Dusoline	HMDB
Dusoran	HMDB
Dythol	HMDB
Fancol CH	HMDB
Hydrocerin	HMDB
Kathro	HMDB
Lanol	HMDB
Super hartolan	HMDB
Tegolan	HMDB
Cholesterol	HMDB
delta5-Cholesten-3beta-ol	PhytoBank
Δ5-Cholesten-3β-ol	PhytoBank

Chemical Formula

C₂₇H₄₆O

Average Molecular Weight

386.6535

Monoisotopic Molecular Weight

386.354866094

IUPAC Name

(1S,2R,5S,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 Name

(1S,2R,5S,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

Description

belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cholestane steroids

Direct Parent

Cholesterols 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 Framework

Aliphatic homopolycyclic compounds

External Descriptors

cholestanoid (CHEBI:16113 )
3beta-sterol (CHEBI:16113 )
cholestane (C00187 )
Cholesterol and derivatives (C00187 )
Cholestane and derivatives (C00187 )
Cholesterol and derivatives (LMST01010001 )

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	7.02	ALOGPS
logP	7.11	ChemAxon
logS	-7.1	ALOGPS
pKa (Strongest Acidic)	18.2	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	120.62 m³·mol⁻¹	ChemAxon
Polarizability	50.64 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-004i-3911000000-52f5261007adc218f8f8	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-052b-2932000000-1667c83d002043a59fff	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000l-9527000000-5529a262047f5369c9c1	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0mkr-2954000000-60e7d1f5973e4de33dec	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-014i-1009000000-e82b8e23dedb45ce70e6	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-056v-2900000000-04687c9f19ff52ba4654	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-05i3-1109000000-8cd386b595bd5151c5a2	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0006-3104900000-698223f49da0b0c1cf81	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 27V, positive	splash10-052u-0690000000-36b4aea6637bdf069b5d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 5V, positive	splash10-014i-3639000000-18a9275beb9bae48c1d7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 10V, positive	splash10-014j-4934000000-f755ada933cfcf53c303	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 15V, positive	splash10-0002-5921000000-e7d43c825b9f6d45e679	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 20V, positive	splash10-0532-5910000000-ce90c49b7429a03a65da	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 30V, positive	splash10-05nb-8900000000-2e8913fec7126b5b2a62	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 40V, positive	splash10-0apl-9600000000-3096c7a78c3dd2e6a538	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 50V, positive	splash10-067l-9400000000-1b57543b4cd0a05b9b3f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 60V, positive	splash10-0aru-9300000000-45a29b76dfefce3f01ca	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014r-0009000000-dccd68f70545aeac4fab	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05p9-3149000000-7f25daf2b709c7e0d177	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0c00-6269000000-5333d0216e01a3e43367	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-dc853b29b9e884bbb03b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0009000000-09d9608700564a6fef78	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ldi-1009000000-96f6e67651380e1c959e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0009000000-2d9cbc8b5b1fa392fb9b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0abj-9173000000-9086873e4b65db1ced63	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-8920000000-bd94fa538afb75d04765	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-c037f2d2f217e99b79ac	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0009000000-7de5154056e69e7319e1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-0009000000-96c53273291d4857bde4	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4l-7922000000-36e8a5e1a77d2e71d1d1	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Bile acid
Follicular Fluid
Milk
Plasma
Rumen
Serum
Skim milk

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Bile acid	Detected but not Quantified	Not Applicable	Not Available	Porcine	21859467	details
Follicular Fluid	Detected and Quantified	687.954 uM	Not Available	Bovine	C. Lutwak-Mann. N...	details
Milk	Detected and Quantified	140 mg/kg	Not Available	Bovine	11913692	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Ovine	Park, Y. W; Juáre...	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	Kurt J. Boudonck,...	details
Milk	Detected and Quantified	341.8+/-15.6 mg/100g fat	Not Available	Caprine	Park, Y. W; Juáre...	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	1779072	details
Plasma	Detected and Quantified	2010 +/- 50 uM	Not Available	Porcine	22612070	details
Plasma	Detected and Quantified	1815.838 +/- 142.505 uM	Not Available	Bovine	Abdullah BAŞOĞLU,...	details
Plasma	Detected and Quantified	2317.320 +/- 236.387 uM	Not Available	Bovine	Abdullah BAŞOĞLU,...	details
Plasma	Detected and Quantified	3341.493 +/- 370.616 uM	Not Available	Bovine	Abdullah BAŞOĞLU,...	details
Plasma	Detected and Quantified	2000-15800 uM	Not Available	Porcine	19603403	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	Trabi M, Keller M...	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Equine	E. E. Escalona, J...	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	19603403	details
Plasma	Detected and Quantified	1940-2330 uM	Not Available	Porcine	Jianxiang XU,Deng...	details
Rumen	Detected but not Quantified	Not Applicable	Not Available	Bovine	Hanne Christine B...	details
Serum	Detected and Quantified	1380.0470-1382.633 uM	Not Available	Ovine	Edson Ferraz Evar...	details
Serum	Detected and Quantified	2940 +/- 430 uM	Not Available	Porcine	21429726	details
Serum	Detected and Quantified	3790 +/- 420 uM	Not Available	Porcine	21429726	details
Serum	Detected and Quantified	4138071.943 uM	Not Available	Bovine	M.J. Abarghuei, Y...	details
Serum	Detected and Quantified	4189797.842 uM	Not Available	Bovine	M.J. Abarghuei, Y...	details
Serum	Detected and Quantified	5431219.425 uM	Not Available	Bovine	M.J. Abarghuei, Y...	details
Serum	Detected and Quantified	5560534.173 uM	Not Available	Bovine	M.J. Abarghuei, Y...	details
Serum	Detected and Quantified	2910 uM	Not Available	Bovine	2286555	details
Serum	Detected and Quantified	3290 uM	Not Available	Bovine	2286555	details
Serum	Detected and Quantified	1600 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	1700 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	1600 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	2000 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	24451218	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	23255817	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	22761248	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	21761043	details
Serum	Detected and Quantified	775.888 uM	Not Available	Bovine	Arthur K. Anderso...	details
Skim milk	Detected and Quantified	20 mg/kg	Not Available	Bovine	11913692	details