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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-10-23 18:07:11 UTC
HMDB IDHMDB0000610
Secondary Accession Numbers
  • HMDB00610
  • HMDB05192
Metabolite Identification
Common NameCE(18:2(9Z,12Z))
DescriptionCholesteryl linoleic 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). Cholesteryl linoleate is contained in low density lipoprotein and atherosclerotic lesions. The oxidation products of cholesteryl linoleate may cause chronic inflammatory processes. (PMID 9684755 , 11950694 ).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC45H76O2
Average Molecular Weight649.101
Monoisotopic Molecular Weight648.584531687
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number604-33-1
SMILESNot Available
InChI Identifier
InChI=1S/C45H76O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-25-43(46)47-38-30-32-44(5)37(34-38)26-27-39-41-29-28-40(36(4)24-22-23-35(2)3)45(41,6)33-31-42(39)44/h11-12,14-15,26,35-36,38-42H,7-10,13,16-25,27-34H2,1-6H3/b12-11-,15-14-/t36-,38+,39?,40?,41?,42?,44+,45-/m1/s1
InChI KeyNAACPBBQTFFYQB-XHDSEGDBSA-N
Chemical Taxonomy
ClassificationNot classified
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Tissue and substructures:

  Cell and elements:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

Role

Industrial application:

Biological role:

  Molecular messenger:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-02cu-2249036000-982a939d936e4145f409View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0024009000-cce26a76d81022551064View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0049003000-279ae0d99e8b8a89b4eaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ku-2029000000-286796af38311acd982dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-1055029000-278e2cdd4d844602dfe0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02g9-5279041000-8c335b2ffc97bdef290bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0axr-5359120000-7e557cfcdd9040140e0bView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1506.38 +/- 204.89 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified1820 +/- 85 uMAdult (>18 years old)BothNormal details
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 IDFDB022141
KNApSAcK IDNot Available
Chemspider ID4450205
KEGG Compound IDC15441
BioCyc IDCholesterol-esters
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5584
PubChem Compound5287939
PDB IDCLL
ChEBI ID41509
References
Synthesis ReferenceLundberg, Bo; Pellas, Lars. Preparation and characterization of cholesteryl linoleate. Acta Academiae Aboensis, Series B: Mathematica et Physica (1973), 33(4), 4 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Lima ES, Di Mascio P, Abdalla DS: Cholesteryl nitrolinoleate, a nitrated lipid present in human blood plasma and lipoproteins. J Lipid Res. 2003 Sep;44(9):1660-6. Epub 2003 Jul 1. [PubMed:12837858 ]
  2. Saito Y, Shiki Y, Shirai K, Yoshida S: Effect of a new synthetic 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitor on cholesterol synthesis and low density lipoprotein uptake by primary cultures of rat hepatocytes. Arzneimittelforschung. 1988 Feb;38(2):251-3. [PubMed:3130840 ]
  3. Yamakoshi J, Kataoka S, Koga T, Ariga T: Proanthocyanidin-rich extract from grape seeds attenuates the development of aortic atherosclerosis in cholesterol-fed rabbits. Atherosclerosis. 1999 Jan;142(1):139-49. [PubMed:9920515 ]
  4. Karten B, Boechzelt H, Abuja PM, Mittelbach M, Oettl K, Sattler W: Femtomole analysis of 9-oxononanoyl cholesterol by high performance liquid chromatography. J Lipid Res. 1998 Jul;39(7):1508-19. [PubMed:9684755 ]
  5. Huber J, Boechzelt H, Karten B, Surboeck M, Bochkov VN, Binder BR, Sattler W, Leitinger N: Oxidized cholesteryl linoleates stimulate endothelial cells to bind monocytes via the extracellular signal-regulated kinase 1/2 pathway. Arterioscler Thromb Vasc Biol. 2002 Apr 1;22(4):581-6. [PubMed:11950694 ]

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