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Record Information
Version4.0
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-09-27 07:47:58 UTC
HMDB IDHMDB0000658
Secondary Accession Numbers
  • HMDB00658
  • HMDB05197
Metabolite Identification
Common NameCE(16:1(9Z))
DescriptionCE(16:1(9Z)) 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. (PMID 2770299 , 8943795 ).
Structure
Thumb
Synonyms
ValueSource
(Z)-Cholesterol 9-hexadecenoateHMDB
(Z)-Cholesterol 9-hexadecenoic acidHMDB
1-Palmitoleoyl-cholesterolHMDB
16:1(9Z) Cholesterol esterHMDB
CE(16:1)HMDB
CE(16:1/0:0)HMDB
CE(16:1n7/0:0)HMDB
CE(16:1W7/0:0)HMDB
Cholest-5-en-3beta-yl (9Z hexadecenoateHMDB
Cholest-5-en-3beta-yl (9Z hexadecenoate)HMDB
Cholest-5-en-3beta-yl (9Z hexadecenoic acidHMDB
Cholesterol 1-(9Z-hexadecenoateHMDB
Cholesterol 1-(9Z-hexadecenoate)HMDB
Cholesterol 1-(9Z-hexadecenoic acidHMDB
Cholesterol 1-(9Z-hexadecenoic acid)HMDB
Cholesterol 1-palmitoleoateHMDB
Cholesterol 1-palmitoleoic acidHMDB
Cholesterol ester(16:1)HMDB
Cholesterol ester(16:1/0:0)HMDB
Cholesterol ester(16:1n7/0:0)HMDB
Cholesterol ester(16:1W7/0:0)HMDB
Cholesterol palmitoleateHMDB
Cholesteryl 1-(9Z-hexadecenoateHMDB
Cholesteryl 1-(9Z-hexadecenoate)HMDB
Cholesteryl 1-(9Z-hexadecenoic acidHMDB
Cholesteryl 1-(9Z-hexadecenoic acid)HMDB
Cholesteryl 1-palmitoleoateHMDB
Cholesteryl 1-palmitoleoic acidHMDB
Cholesteryl cis-hexadecenoateHMDB
Cholesteryl cis-hexadecenoic acidHMDB
Cholesteryl palmitoleatHMDB
Cholesteryl palmitoleateHMDB
Cholesteryl palmitoleic acidHMDB
1-(9Z-hexadecenoyl)-cholesterol; cholesteryl 1-palmitoleoic acidLipid Annotator
CE(16:1(9Z))Lipid Annotator
1-(9Z-hexadecenoyl)-cholesterolLipid Annotator
Chemical FormulaC43H74O2
Average Molecular Weight623.063
Monoisotopic Molecular Weight622.568881623
IUPAC Name(2R,5S,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl (9Z)-hexadec-9-enoate
Traditional Name(2R,5S,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl (9Z)-hexadec-9-enoate
CAS Registry Number16711-66-3
SMILES
CCCCCC\C=C/CCCCCCCC(=O)O[C@H]1CC[C@]2(C)C3CC[C@]4(C)C(CCC4C3CC=C2C1)[C@H](C)CCCC(C)C
InChI Identifier
InChI=1S/C43H74O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-23-41(44)45-36-28-30-42(5)35(32-36)24-25-37-39-27-26-38(34(4)22-20-21-33(2)3)43(39,6)31-29-40(37)42/h12-13,24,33-34,36-40H,7-11,14-23,25-32H2,1-6H3/b13-12-/t34-,36+,37?,38?,39?,40?,42+,43-/m1/s1
InChI KeyHODJWNWCVNUPAQ-XLUROLQISA-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
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

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 Properties
PropertyValueSource
Water Solubility5.8e-06 g/LALOGPS
logP10.44ALOGPS
logP13.67ChemAxon
logS-8ALOGPS
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
Polarizability83.26 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00dr-0024009000-69f58d56b9aab51b71eaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0049003000-e8baef11f1d1279c69acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ku-2029000000-940b494f7a9dcf0e372cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-1255039000-31eda8d2e0d85c9d0306View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05n0-5449030000-a600e4e0cfe381e9f7a7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-5719230000-9c5803bd30c50c2ab1fdView 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 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
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022167
KNApSAcK IDNot Available
Chemspider ID17215988
KEGG Compound IDC02530
BioCyc IDCholesterol-esters
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5629
PubChem Compound22833543
PDB IDNot Available
ChEBI IDNot Available
References
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 ]

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