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Record Information
Version3.6
Creation Date2006-05-22 14:17:45 UTC
Update Date2016-02-11 01:05:30 UTC
HMDB IDHMDB02262
Secondary Accession Numbers
  • HMDB06739
Metabolite Identification
Common NameCE(12:0)
DescriptionCholesteryl lauric acid is a cholesteryl ester. A cholesteryl ester is an ester of cholesterol. Fatty acid esters of cholesterol constitute about two-thirds of the cholesterol in the plasma. 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 accumulation of cholesterol esters in the arterial intima (the innermost layer of an artery, in direct contact with the flowing blood) is a characteristic feature of atherosclerosis. Atherosclerosis is a disease affecting arterial blood vessels. It is a chronic inflammatory response in the walls of arteries, in large part to the deposition of lipoproteins (plasma proteins that carry cholesterol and triglycerides). Lauric acid greatly increases total cholesterol, but much of its effect is on HDL cholesterol. Consequently, oils rich in lauric acid decrease the ratio of total to HDL cholesterol. (PMID: 12716665 , 8644684 , 10030391 ).
Structure
Thumb
Synonyms
ValueSource
(3beta)-Cholest-5-en-3-ol dodecanoateHMDB
(3beta)-Cholest-5-en-3-ol dodecanoic acidHMDB
12:0 Cholesterol esterHMDB
Cholest-5-en-3-beta-yl laurateHMDB
Cholest-5-en-3-yl laurateHMDB
Cholest-5-en-3b-ol dodecanoateHMDB
Cholest-5-en-3b-ol dodecanoic acidHMDB
Cholest-5-en-3beta-ol dodecanoateHMDB
Cholest-5-en-3beta-ol dodecanoic acidHMDB
Cholest-5-en-3beta-yl dodecanoateHMDB
Cholest-5-en-3beta-yl dodecanoic acidHMDB
Cholesterol laurateHMDB
Cholesteryl dodecanoateHMDB
Cholesteryl dodecanoic acidHMDB
Cholesteryl laurateHMDB
Cholesteryl lauric acidHMDB
DodecanoateHMDB
Dodecanoic acidHMDB
Dodecanoic acid cholesteryl esterHMDB
Chemical FormulaC39H68O2
Average Molecular Weight568.956
Monoisotopic Molecular Weight568.52193142
IUPAC Name(1S,2R,5S,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-yl dodecanoate
Traditional Namecholesteryl laurate
CAS Registry Number1908-11-8
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)OC(=O)CCCCCCCCCCC)[C@H](C)CCCC(C)C
InChI Identifier
InChI=1S/C39H68O2/c1-7-8-9-10-11-12-13-14-15-19-37(40)41-32-24-26-38(5)31(28-32)20-21-33-35-23-22-34(30(4)18-16-17-29(2)3)39(35,6)27-25-36(33)38/h20,29-30,32-36H,7-19,21-28H2,1-6H3/t30-,32+,33+,34-,35+,36+,38+,39-/m1/s1
InChI KeyInChIKey=RMLFYKFCGMSLTB-ZBDFTZOCSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as cholesteryl esters. These are compounds containing an esterified cholestane moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid esters
Direct ParentCholesteryl esters
Alternative Parents
Substituents
  • Cholesteryl ester
  • Cholesterol
  • Cholestane-skeleton
  • Delta-5-steroid
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility7.3e-06 mg/mLALOGPS
logP9.93ALOGPS
logP12.26ChemAxon
logS-7.9ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 Å2ChemAxon
Rotatable Bond Count17ChemAxon
Refractivity175.8 m3·mol-1ChemAxon
Polarizability76.62 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022932
KNApSAcK IDNot Available
Chemspider ID92314
KEGG Compound IDC02530
BioCyc IDCholesterol-esters
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB02262
Metagene LinkHMDB02262
METLIN IDNot Available
PubChem Compound102182
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Mensink RP, Zock PL, Kester AD, Katan MB: Effects of dietary fatty acids and carbohydrates on the ratio of serum total to HDL cholesterol and on serum lipids and apolipoproteins: a meta-analysis of 60 controlled trials. Am J Clin Nutr. 2003 May;77(5):1146-55. [12716665 ]
  2. Temme EH, Mensink RP, Hornstra G: Comparison of the effects of diets enriched in lauric, palmitic, or oleic acids on serum lipids and lipoproteins in healthy women and men. Am J Clin Nutr. 1996 Jun;63(6):897-903. [8644684 ]
  3. Lagrost L, Mensink RP, Guyard-Dangremont V, Temme EH, Desrumaux C, Athias A, Hornstra G, Gambert P: Variations in serum cholesteryl ester transfer and phospholipid transfer activities in healthy women and men consuming diets enriched in lauric, palmitic or oleic acids. Atherosclerosis. 1999 Feb;142(2):395-402. [10030391 ]

Enzymes

General function:
Involved in phosphatidylcholine-sterol O-acyltransferase activity
Specific function:
Central enzyme in the extracellular metabolism of plasma lipoproteins. Synthesized mainly in the liver and secreted into plasma where it converts cholesterol and phosphatidylcholines (lecithins) to cholesteryl esters and lysophosphatidylcholines on the surface of high and low density lipoproteins (HDLs and LDLs). The cholesterol ester is then transported back to the liver. Has a preference for plasma 16:0-18:2 or 18:O-18:2 phosphatidylcholines. Also produced in the brain by primary astrocytes, and esterifies free cholesterol on nascent APOE-containing lipoproteins secreted from glia and influences cerebral spinal fluid (CSF) APOE- and APOA1 levels. Together with APOE and the cholesterol transporter ABCA1, plays a key role in the maturation of glial-derived, nascent lipoproteins. Required for remodeling high-density lipoprotein particles into their spherical forms.
Gene Name:
LCAT
Uniprot ID:
P04180
Molecular weight:
49577.545
General function:
Involved in lipid metabolic process
Specific function:
Crucial for the intracellular hydrolysis of cholesteryl esters and triglycerides that have been internalized via receptor-mediated endocytosis of lipoprotein particles. Important in mediating the effect of LDL (low density lipoprotein) uptake on suppression of hydroxymethylglutaryl-CoA reductase and activation of endogenous cellular cholesteryl ester formation.
Gene Name:
LIPA
Uniprot ID:
P38571
Molecular weight:
45418.71
General function:
Lipid transport and metabolism
Specific function:
Catalyzes fat and vitamin absorption. Acts in concert with pancreatic lipase and colipase for the complete digestion of dietary triglycerides.
Gene Name:
CEL
Uniprot ID:
P19835
Molecular weight:
79666.385
General function:
Lipid transport and metabolism
Specific function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
Gene Name:
CES1
Uniprot ID:
P23141
Molecular weight:
62520.62
General function:
Involved in acyl-CoA binding
Specific function:
Plays a role in lipoprotein assembly and dietary cholesterol absorption. In addition to its acyltransferase activity, it may act as a ligase. May provide cholesteryl esters for lipoprotein secretion from hepatocytes and intestinal mucosa.
Gene Name:
SOAT2
Uniprot ID:
O75908
Molecular weight:
59895.735
General function:
Involved in acyl-CoA binding
Specific function:
Catalyzes the formation of fatty acid-cholesterol esters. Plays a role in lipoprotein assembly and dietary cholesterol absorption. In addition to its acyltransferase activity, it may act as a ligase.
Gene Name:
SOAT1
Uniprot ID:
P35610
Molecular weight:
58130.665
General function:
Involved in cell adhesion
Specific function:
Receptor for different ligands such as phospholipids, cholesterol ester, lipoproteins, phosphatidylserine and apoptotic cells. Probable receptor for HDL, located in particular region of the plasma membrane, called caveolae. Facilitates the flux of free and esterified cholesterol between the cell surface and extracellular donors and acceptors, such as HDL and to a lesser extent, apoB-containing lipoproteins and modified lipoproteins. Probably involved in the phagocytosis of apoptotic cells, via its phosphatidylserine binding activity. Receptor for hepatitis C virus glycoprotein E2. Binding between SCARB1 and E2 was found to be independent of the genotype of the viral isolate. Plays an important role in the uptake of HDL cholesteryl ester
Gene Name:
SCARB1
Uniprot ID:
Q8WTV0
Molecular weight:
60877.4
General function:
Involved in hydrolase activity
Specific function:
Hydrolyzes 2-acetyl monoalkylglycerol ether, the penultimate precursor of the pathway for de novo synthesis of platelet-activating factor. May be responsible for cholesterol ester hydrolysis in macrophages, thereby contributing to the development of atherosclerosis. Also involved in organ detoxification by hydrolyzing exogenous organophosphorus compounds. May contribute to cancer pathogenesis by promoting tumor cell migration
Gene Name:
NCEH1
Uniprot ID:
Q6PIU2
Molecular weight:
45807.4