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Record Information
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-07-12 17:07:38 UTC
Secondary Accession Numbers
  • HMDB0005197
  • HMDB0062460
  • HMDB00658
  • HMDB05197
  • HMDB62460
Metabolite Identification
Common NameCE(16:1)
DescriptionCE(16:1(9Z)), also known as (Z)-cholesterol 9-hexadecenoate or 1-palmitoleoyl-cholesterol, is an important plasma 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 palmitoleate is one of the two more prevalent esters that are a component of dehydroepiandrosterone fatty acid esters (DHEA-FA). DHEA-FA is formed from DHEA by lecithin-cholesterol acyltransferase, localized on high-density lipoprotein (HDL). Once DHEA-FA is formed, it is subsequently transferred to very low-density lipoprotein (VLDL) and low-density lipoprotein (LDL), like cholesteryl esters. Cholesteryl palmitoleate constitutes 20% of the total lipoidal pregnenolone (an important precursor steroid) in follicular fluid. The fatty acid components of the resulting lipoidal pregnenolone derivatives resemble those of cholesteryl esters formed in plasma by the enzymatic activity of lecithin–cholesterol acyltransferase (LCAT) (PMID: 2770299 , 8943795 ). CE(16:1(9Z)) is considered to be practically insoluble (in water) and basic.
(Z)-Cholesterol 9-hexadecenoateChEBI
(Z)-Cholesterol 9-hexadecenoic acidChEBI
16:1(9Z) Cholesterol esterChEBI
Cholesterol cis-9-hexadecenoateChEBI
Cholesteryl (9Z)-hexadecenoateChEBI
Cholesterol cis-9-hexadecenoic acidGenerator
Cholesteryl (9Z)-hexadecenoic acidGenerator
Cholesteryl palmitoleic acidGenerator
Cholest-5-en-3b-yl (9Z-hexadecenoate)Generator, HMDB
Cholest-5-en-3b-yl (9Z-hexadecenoic acid)Generator, HMDB
Cholest-5-en-3beta-yl (9Z-hexadecenoic acid)Generator, HMDB
Cholest-5-en-3β-yl (9Z-hexadecenoate)Generator, HMDB
Cholest-5-en-3β-yl (9Z-hexadecenoic acid)Generator, HMDB
Cholesteryl 9-hexadecenoateHMDB
Cholesteryl 9-palmitelaidateHMDB
Cholesteryl 9-palmitoleateHMDB
Cholesteryl cis-9-hexadecenoateHMDB
Cholesterol palmitoleateHMDB
Cholesteryl cis-hexadecenoateHMDB
Cholesteryl palmitoleateHMDB
Cholest-5-en-3beta-yl (9Z-hexadecenoate)HMDB
Chemical FormulaC43H74O2
Average Molecular Weight623.063
Monoisotopic Molecular Weight622.568881623
IUPAC Name(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[^{2,7}.0^{11,15}]heptadec-7-en-5-yl (9Z)-hexadec-9-enoate
Traditional Name(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[^{2,7}.0^{11,15}]heptadec-7-en-5-yl (9Z)-hexadec-9-enoate
CAS Registry Number16711-66-3
InChI Identifier
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cholesteryl esters. Cholesteryl esters 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
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Physiological effect
Physical Properties
Experimental Molecular Properties
Melting PointNot AvailableNot Available
Boiling Point655.26 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility3.5e-20 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP17.265 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Water Solubility5.8e-06 g/LALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity195.32 m³·mol⁻¹ChemAxon
Polarizability82.59 ųChemAxon
Number of Rings4ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference

Predicted Kovats Retention Indices


MetaboliteSMILESKovats RI ValueColumn TypeReference
CE(16:1(9Z))[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)CCCCCCC\C=C/CCCCCC)[C@H](C)CCCC(C)C4052.1Standard polar33892256
CE(16:1(9Z))[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)CCCCCCC\C=C/CCCCCC)[C@H](C)CCCC(C)C4708.1Standard non polar33892256
CE(16:1(9Z))[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)CCCCCCC\C=C/CCCCCC)[C@H](C)CCCC(C)C4588.6Semi standard non polar33892256

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - CE(16:1) GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-4529073000-025ba6e44b9eae49618d2017-09-20Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(16:1) 10V, Positive-QTOFsplash10-00dr-1255039000-31eda8d2e0d85c9d03062017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(16:1) 20V, Positive-QTOFsplash10-05n0-5449030000-a600e4e0cfe381e9f7a72017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(16:1) 40V, Positive-QTOFsplash10-0a4l-5719230000-9c5803bd30c50c2ab1fd2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(16:1) 10V, Negative-QTOFsplash10-00dr-0024009000-69f58d56b9aab51b71ea2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(16:1) 20V, Negative-QTOFsplash10-000i-0049003000-e8baef11f1d1279c69ac2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(16:1) 40V, Negative-QTOFsplash10-00ku-2029000000-940b494f7a9dcf0e372c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(16:1) 10V, Negative-QTOFsplash10-00di-0000009000-a8b40f0a55b15e3e945a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(16:1) 20V, Negative-QTOFsplash10-0079-1092007000-7d857be6d28d2fb2dee32021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(16:1) 40V, Negative-QTOFsplash10-014i-4920005000-4432da2eefef12b90a882021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(16:1) 10V, Positive-QTOFsplash10-0600-9013026000-23fa50f7ff69b4b387102021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(16:1) 20V, Positive-QTOFsplash10-0a4i-9110000000-615e076cfa8f608fe3912021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(16:1) 40V, Positive-QTOFsplash10-0a4i-9210000000-77c635e834776fd35b8d2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Normal Concentrations
BloodDetected and Quantified118.74 +/- 45.54 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified111 +/- 4 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID20147342
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID84323
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1440091
Synthesis ReferenceWang, Stephen T.; Peter, Frank. Gas-liquid chromatographic determination of fatty acid composition of cholesteryl esters in human serum using silica Sep-Pak cartridges. Journal of Chromatography (1983), 276(2), 249-56.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Roy R, Belanger A: Formation of lipoidal steroids in follicular fluid. J Steroid Biochem. 1989 Aug;33(2):257-62. [PubMed:2770299 ]
  2. Lavallee B, Provost PR, Roy R, Gauthier MC, Belanger A: Dehydroepiandrosterone-fatty acid esters in human plasma: formation, transport and delivery to steroid target tissues. J Endocrinol. 1996 Sep;150 Suppl:S119-24. [PubMed:8943795 ]
  3. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  4. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  5. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  6. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.


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:
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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.
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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.
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General function:
Lipid transport and metabolism
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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:
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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.
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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.
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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
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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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