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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:02 UTC
HMDB IDHMDB00610
Secondary Accession Numbers
  • 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
Synonyms
ValueSource
(3beta)-Cholest-5-en-3-ol, (9Z,12Z)-9,12-octadecadienoateChEBI
(3beta)-Cholest-5-en-3-ol, (Z,Z)-9,12-octadecadienoateChEBI
(Z,Z)-(3beta)-Cholest-5-en-3-ol 9,12-octadecadienoateChEBI
18:2 Cholesteryl esterChEBI
CE(18:2(9Z,12Z))ChEBI
CE(18:2)ChEBI
Cholest-5-en-3beta-yl (Z,Z)-octadeca-9,12-dienoateChEBI
Cholesteryl (9Z,12Z-octadecadienoate)ChEBI
(3b)-Cholest-5-en-3-ol, (9Z,12Z)-9,12-octadecadienoateGenerator
(3b)-Cholest-5-en-3-ol, (9Z,12Z)-9,12-octadecadienoic acidGenerator
(3beta)-Cholest-5-en-3-ol, (9Z,12Z)-9,12-octadecadienoic acidGenerator
(3β)-cholest-5-en-3-ol, (9Z,12Z)-9,12-octadecadienoateGenerator
(3β)-cholest-5-en-3-ol, (9Z,12Z)-9,12-octadecadienoic acidGenerator
1-Linoleoyl-cholesterolHMDB
18:2(9Z,12Z) Cholesterol esterHMDB
CE(18:2/0:0)HMDB
CE(18:2n6/0:0)HMDB
CE(18:2W6/0:0)HMDB
Cholest-5-en-3beta-yl (9Z,12Z-octadecadienoateHMDB
Cholest-5-en-3beta-yl (9Z,12Z-octadecadienoate)HMDB
Cholest-5-en-3beta-yl (9Z,12Z-octadecadienoic acidHMDB
Cholesterol 1-(9Z,12Z-octadecadienoateHMDB
Cholesterol 1-(9Z,12Z-octadecadienoate)HMDB
Cholesterol 1-(9Z,12Z-octadecadienoic acidHMDB
Cholesterol 1-(9Z,12Z-octadecadienoic acid)HMDB
Cholesterol 1-linoleoateHMDB
Cholesterol 1-linoleoic acidHMDB
Cholesterol ester(18:2)HMDB
Cholesterol ester(18:2/0:0)HMDB
Cholesterol ester(18:2n6/0:0)HMDB
Cholesterol ester(18:2W6/0:0)HMDB
Cholesteryl 1-(9Z,12Z-octadecadienoateHMDB
Cholesteryl 1-(9Z,12Z-octadecadienoate)HMDB
Cholesteryl 1-(9Z,12Z-octadecadienoic acidHMDB
Cholesteryl 1-(9Z,12Z-octadecadienoic acid)HMDB
Cholesteryl 1-linoleoateHMDB
Cholesteryl 1-linoleoic acidHMDB
Chemical FormulaC45H76O2
Average Molecular Weight649.0837
Monoisotopic Molecular Weight648.584531676
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 (9Z,12Z)-octadeca-9,12-dienoate
Traditional Namecholesteryl linoleate
CAS Registry Number604-33-1
SMILES
CCCCC\C=C/C\C=C/CCCCCCCC(=O)O[C@H]1CC[C@@]2(C)C(=CC[C@@]3([H])[C@]4([H])CC[C@]([H])([C@H](C)CCCC(C)C)[C@@]4(C)CC[C@]23[H])C1
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 KeyInChIKey=NAACPBBQTFFYQB-LJAITQKLSA-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
  • Octadecanoid
  • 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
StatusDetected and 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 (predicted from logP)
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 Solubility5.79e-06 mg/mLALOGPS
logP10.5ALOGPS
logP14.2ChemAxon
logS-8.1ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 Å2ChemAxon
Rotatable Bond Count21ChemAxon
Refractivity205.64 m3·mol-1ChemAxon
Polarizability86.55 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0002-0000009000-be0d242fdc5dfce84520View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0002-0000009000-f746df3c4960ff441e25View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00kb-0380309000-9563a2875a28afc28571View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
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
NuGOwiki LinkHMDB00610
Metagene LinkHMDB00610
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. [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. [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. [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. [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. [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