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Record Information
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:33 UTC
Secondary Accession Numbers
  • HMDB05191
Metabolite Identification
Common NameCE(18:1(9Z))
DescriptionCholesteryl oleate 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 esters, formed by the esterification of cholesterol with long-chain fatty acids, on one hand, are the means by which cholesterol is transported through the blood by lipoproteins, on the other, the way cholesterol itself can be accumulated in the cells. (PMID: 15939411 ).
(3beta)-Cholest-5-en-3-ol, (Z)-9-octadecenoateChEBI
18:1 Cholesteryl esterChEBI
Cholest-5-en-3-beta-yl oleateChEBI
Cholest-5-en-3-yl (9Z)-9-octadecenoateChEBI
Cholesteryl (9Z-octadecenoate)ChEBI
Cholesteryl cis-9-octadecenoateChEBI
(3b)-Cholest-5-en-3-ol, (Z)-9-octadecenoateGenerator
(3b)-Cholest-5-en-3-ol, (Z)-9-octadecenoic acidGenerator
(3beta)-Cholest-5-en-3-ol, (Z)-9-octadecenoic acidGenerator
(3β)-cholest-5-en-3-ol, (Z)-9-octadecenoateGenerator
(3β)-cholest-5-en-3-ol, (Z)-9-octadecenoic acidGenerator
Cholesteryl oleic acidGenerator
Cholest-5-en-3-b-yl oleateGenerator
Cholest-5-en-3-b-yl oleic acidGenerator
Cholest-5-en-3-beta-yl oleic acidGenerator
Cholest-5-en-3-β-yl oleateGenerator
Cholest-5-en-3-β-yl oleic acidGenerator
Cholest-5-en-3-yl (9Z)-9-octadecenoic acidGenerator
Cholesteryl (9Z-octadecenoic acid)Generator
Cholesteryl cis-9-octadecenoic acidGenerator
18:1(9Z) Cholesterol esterHMDB
3beta-Hydroxy-5-cholestene 3-oleateHMDB
5-Cholesten-3b-ol 3-oleateHMDB
Cholest-5-en-3-ol (3b)-(Z)-9-octadecenoateHMDB
Cholest-5-en-3-ol (3b)-(Z)-9-octadecenoic acidHMDB
Cholesterol 1-(9Z-octadecenoateHMDB
Cholesterol 1-(9Z-octadecenoate)HMDB
Cholesterol 1-(9Z-octadecenoic acidHMDB
Cholesterol 1-(9Z-octadecenoic acid)HMDB
Cholesterol 3beta-oleateHMDB
Cholesterol ester(18:1)HMDB
Cholesterol ester(18:1/0:0)HMDB
Cholesterol ester(18:1n9/0:0)HMDB
Cholesterol ester(18:1W9/0:0)HMDB
Cholesteryl 1-oleoateHMDB
Cholesteryl 1-oleoic acidHMDB
Cholesteryl oleate-9,10-3HHMDB
Cholesteryl oleate-9,10-t2HMDB
Cholesteryl oleic esterHMDB
Cholesteryl [9,10-3H]oleateHMDB
Oleic acid cholesteryl esterHMDB
Chemical FormulaC45H78O2
Average Molecular Weight651.0996
Monoisotopic Molecular Weight650.60018174
IUPAC Name(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl (9Z)-octadec-9-enoate
Traditional Namecholesteryl oleate
CAS Registry Number303-43-5
InChI Identifier
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
  • 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
StatusDetected and Quantified
  • Endogenous
  • Food
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
Experimental Properties
Melting Point94 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility6.33e-06 mg/mLALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 Å2ChemAxon
Rotatable Bond Count22ChemAxon
Refractivity204.53 m3·mol-1ChemAxon
Polarizability86.5 Å3ChemAxon
Number of Rings4ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-0000009000-21a92605782172dbfd15View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0udi-0000009000-06ae92b73dd60f6a7e36View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-002o-0800980000-fc08d63d7e4e8b45f921View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location
  • Adipose Tissue
  • Adrenal Cortex
  • Adrenal Gland
  • Fibroblasts
  • Intestine
  • Liver
  • Myelin
  • Platelet
  • Spleen
  • Stratum Corneum
  • Testes
PathwaysNot Available
Normal Concentrations
BloodDetected and Quantified704.47 +/- 129.59 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified533 +/- 13 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 IDFDB022317
KNApSAcK IDNot Available
Chemspider ID4446726
KEGG Compound IDC14641
BioCyc IDCholesterol-esters
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00918
Metagene LinkHMDB00918
PubChem Compound5283632
ChEBI ID46898
Synthesis ReferenceSripada P K Synthesis of single- and double-13C-labeled cholesterol oleate. Chemistry and physics of lipids (1988), 48(1-2), 147-51.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Tall A, Granot E, Brocia R, Tabas I, Hesler C, Williams K, Denke M: Accelerated transfer of cholesteryl esters in dyslipidemic plasma. Role of cholesteryl ester transfer protein. J Clin Invest. 1987 Apr;79(4):1217-25. [3558822 ]
  2. Busch SJ, Stuart WD, Hug B, Mao SJ, Harmony JA: Plasma cholesteryl ester-triglyceride transfer protein. The catalytic domain is a low molecular weight proteolipid. J Biol Chem. 1987 Dec 25;262(36):17563-71. [3693366 ]
  3. Adam O, Wolfram G, Zollner N: Influence of dietary linoleic acid intake with different fat intakes on arachidonic acid concentrations in plasma and platelet lipids and eicosanoid biosynthesis in female volunteers. Ann Nutr Metab. 2003;47(1):31-6. [12624485 ]
  4. Hui SP, Murai T, Yoshimura T, Chiba H, Nagasaka H, Kurosawa T: Improved HPLC assay for lipid peroxides in human plasma using the internal standard of hydroperoxide. Lipids. 2005 May;40(5):515-22. [16094862 ]
  5. Benoist F, Lau P, McDonnell M, Doelle H, Milne R, McPherson R: Cholesteryl ester transfer protein mediates selective uptake of high density lipoprotein cholesteryl esters by human adipose tissue. J Biol Chem. 1997 Sep 19;272(38):23572-7. [9295295 ]
  6. Sklar LA, Craig IF, Pownall HJ: Induced circular dichroism of incorporated fluorescent cholesteryl esters and polar lipids as a probe of human serum low density lipoprotein structure and melting. J Biol Chem. 1981 May 10;256(9):4286-92. [7217083 ]
  7. Seo T, Qi K, Chang C, Liu Y, Worgall TS, Ramakrishnan R, Deckelbaum RJ: Saturated fat-rich diet enhances selective uptake of LDL cholesteryl esters in the arterial wall. J Clin Invest. 2005 Aug;115(8):2214-22. Epub 2005 Jul 21. [16041409 ]
  8. Ceryak S, Bouscarel B, Malavolti M, Robins SJ, Caslow KL, Fromm H: Effect of ursodeoxycholic acid on hepatic LDL binding and uptake in dietary hypercholesterolemic hamsters. Atherosclerosis. 2000 Nov;153(1):59-67. [11058700 ]
  9. Gwynne JT, Mahaffee DD: Rat adrenal uptake and metabolism of high density lipoprotein cholesteryl ester. J Biol Chem. 1989 May 15;264(14):8141-50. [2542267 ]
  10. Albers JJ, Marcovina SM, Christenson RH: Lecithin cholesterol acyltransferase in human cerebrospinal fluid: reduced level in patients with multiple sclerosis and evidence of direct synthesis in the brain. Int J Clin Lab Res. 1992;22(3):169-72. [1387817 ]
  11. Matsuda K: ACAT inhibitors as antiatherosclerotic agents: compounds and mechanisms. Med Res Rev. 1994 May;14(3):271-305. [8007738 ]
  12. Katan MB, Deslypere JP, van Birgelen AP, Penders M, Zegwaard M: Kinetics of the incorporation of dietary fatty acids into serum cholesteryl esters, erythrocyte membranes, and adipose tissue: an 18-month controlled study. J Lipid Res. 1997 Oct;38(10):2012-22. [9374124 ]
  13. Kuipers F, Nagelkerke JF, Bakkeren H, Havinga R, Van Berkel TJ, Vonk RJ: Processing of cholesteryl ester from low-density lipoproteins in the rat. Hepatic metabolism and biliary secretion after uptake by different hepatic cell types. Biochem J. 1989 Feb 1;257(3):699-704. [2930479 ]
  14. Oliveira HC, Nilausen K, Meinertz H, Quintao EC: Cholesteryl esters in lymph chylomicrons: contribution from high density lipoprotein transferred from plasma into intestinal lymph. J Lipid Res. 1993 Oct;34(10):1729-36. [8245723 ]
  15. Tosi MR, Tugnoli V: Cholesteryl esters in malignancy. Clin Chim Acta. 2005 Sep;359(1-2):27-45. [15939411 ]


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:
Uniprot ID:
Molecular weight:
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:
Uniprot ID:
Molecular weight:
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:
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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:
Uniprot ID:
Molecular weight:
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:
Uniprot ID:
Molecular weight:
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:
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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:
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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
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