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Record Information
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:29 UTC
Secondary Accession Numbers
  • HMDB05188
Metabolite Identification
Common NameCE(16:0)
DescriptionCholesteryl palmitic 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 palmitate is one of the four important lipids found in the tear film. Amniotic fluid cholesteryl palmitate, as measured by thin-layer chromatography, appears to be a very sensitive and specific predictor for the risk of respiratory distress syndrome (RDS) in newborns of normal pregnancies. (PMID: 3405552 , 16922549 ).
(3beta)-Cholest-5-en-3-ol hexadecanoateChEBI
16:0 Cholesterol esterChEBI
Cholesterol palmitateChEBI
Cholesteryl hexadecanoateChEBI
Hexadecanoic acid, cholesteryl esterChEBI
Palmitic acid cholesteryl esterChEBI
(3b)-Cholest-5-en-3-ol hexadecanoateGenerator
(3b)-Cholest-5-en-3-ol hexadecanoic acidGenerator
(3beta)-Cholest-5-en-3-ol hexadecanoic acidGenerator
(3β)-cholest-5-en-3-ol hexadecanoateGenerator
(3β)-cholest-5-en-3-ol hexadecanoic acidGenerator
Cholesteryl palmitic acidGenerator
Cholesterol palmitic acidGenerator
Cholesteryl hexadecanoic acidGenerator
Hexadecanoate, cholesteryl esterGenerator
Palmitate cholesteryl esterGenerator
Cholest-5-en-3-yl palmitateHMDB
Cholest-5-ene-3-beta-yl palmitateHMDB
Cholesterol 1-hexadecanoateHMDB
Cholesterol 1-hexadecanoic acidHMDB
Cholesterol 1-palmitoateHMDB
Cholesterol 1-palmitoic acidHMDB
Cholesterol ester(16:0)HMDB
Cholesterol ester(16:0/0:0)HMDB
Cholesteryl 1-hexadecanoateHMDB
Cholesteryl 1-hexadecanoic acidHMDB
Cholesteryl 1-palmitoateHMDB
Cholesteryl 1-palmitoic acidHMDB
Hexadecanoic acidHMDB
Hexadecanoic acid cholesteryl esterHMDB
Chemical FormulaC43H76O2
Average Molecular Weight625.0623
Monoisotopic Molecular Weight624.584531676
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 hexadecanoate
Traditional Namecholesteryl palmitate
CAS Registry Number601-34-3
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
Physical Properties
Experimental Properties
Melting Point75 - 77 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility6.89e-06 mg/mLALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 Å2ChemAxon
Rotatable Bond Count21ChemAxon
Refractivity194.21 m3·mol-1ChemAxon
Polarizability84.17 Å3ChemAxon
Number of Rings4ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BloodDetected and Quantified405.46 +/- 56.51 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified208 +/- 7.8 uMAdult (>18 years old)Both
BloodDetected and Quantified190 +/- 6 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified200 +/- 4.5 uMAdult (>18 years old)Both
Abnormal Concentrations
BloodDetected and Quantified857.0 +/- 14.0 uMAdult (>18 years old)BothHypercholesterolemia details
Associated Disorders and Diseases
Disease References
  1. Kim DH, Lee KJ, Heo GS: Analysis of cholesterol and cholesteryl esters in human serum using capillary supercritical fluid chromatography. J Chromatogr B Biomed Appl. 1994 Apr 22;655(1):1-8. [8061816 ]
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022299
KNApSAcK IDNot Available
Chemspider ID215725
KEGG Compound IDC11251
BioCyc IDCholesterol-esters
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00885
Metagene LinkHMDB00885
PubChem Compound246520
PDB IDNot Available
ChEBI ID3663
Synthesis ReferenceMahadevan, V.; Lundberg, W. O. Preparation of cholesteryl esters of long-chain fatty acids. Journal of the American Oil Chemists' Society (1960), 37 685.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Snow JW, Glick JM, Phillips MC: The phase behavior of cholesteryl esters in intracellular inclusions. J Biol Chem. 1992 Sep 15;267(26):18564-72. [1326528 ]
  2. Mudgil P, Dennis GR, Millar TJ: Interactions of poly(tert-butyl acrylate)-poly(styrene) diblock copolymers with lipids at the air-water interface. Langmuir. 2006 Aug 29;22(18):7672-7. [16922549 ]
  3. Ludmir J, Alvarez JG, Landon MB, Gabbe SG, Mennuti MT, Touchstone JC: Amniotic fluid cholesteryl palmitate in pregnancies complicated by diabetes mellitus. Obstet Gynecol. 1988 Sep;72(3 Pt 1):360-2. [3405552 ]
  4. Van Biervliet JP, Vinaimont N, Vercaemst R, Rosseneu M: Serum cholesterol, cholesteryl ester, and high-density lipoprotein development in newborn infants: response to formulas supplemented with cholesterol and gamma-linolenic acid. J Pediatr. 1992 Apr;120(4 Pt 2):S101-8. [1313864 ]
  5. Rosseneu M, Cambien F, Vinaimont N, Nicaud V, De Backer G: Biomarkers of dietary fat composition in young adults with a parental history of premature coronary heart disease compared with controls. The EARS Study. Atherosclerosis. 1994 Aug;108(2):127-36. [7980712 ]
  6. Alvarez JG, Ludmir J: Semiautomated multisample analysis of amniotic fluid lipids by high-performance thin-layer chromatography-reflectance spectrodensitometry. J Chromatogr. 1993 May 19;615(1):142-7. [8340452 ]
  7. Jachec W, Tomasik A, Ceglarek W, Wos S, Wodniecki J, Wojciechowska C, Skrzep-Poloczek B, Walichiewicz P, Widenka K: Lipid peroxidation and vitamin E in human coronary atherosclerotic lesions. Clin Chim Acta. 2003 Apr;330(1-2):121-9. [12636930 ]
  8. Ludmir J, Alvarez JG, Mennuti MT, Gabbe SG, Touchstone JC: Cholesteryl palmitate as a predictor of fetal lung maturity. Am J Obstet Gynecol. 1987 Jul;157(1):84-8. [3605272 ]


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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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.
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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
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:
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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.
Gene Name:
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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.
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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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