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Record Information
StatusExpected but not Quantified
Creation Date2007-09-06 12:15:09 UTC
Update Date2022-11-30 19:02:48 UTC
Secondary Accession Numbers
  • HMDB06738
Metabolite Identification
Common NameCE(19:0)
DescriptionCholesteryl nonadecanoic acid is a cholesteryl ester. Cholesteryl ester (CE) is the major transport and storage form of cholesterol in lipoprotein particles and most cell types. Molecular composition of CE species is of high interest for arteriosclerosis research, i.e., as components of lipoprotein subclasses or in studies investigating the mechanisms involved in the generation of lipid laden foam cells. Thus, it has been shown that CE species in circulating plasma are strongly correlated with development of coronary heart disease. This may be related to specific CE species profiles generated by enzymes involved in lipoprotein metabolism like lecithin:cholesterol acyltransferase (EC, LCAT), acyl-coenzyme A:cholesterol acyltransferase 2 (EC, ACAT2) or cholesteryl ester transfer protein (CETP). The cholesteryl ester transfer protein has a key role in the metabolism of high-density lipoprotein (HDL), mediating the exchange of lipids between lipoproteins, resulting in the net transfer of cholesteryl ester from HDL to other lipoproteins and in the subsequent uptake of cholesterol by hepatocytes. By increasing the cholesteryl ester content of low-density and very-low-density lipoproteins, CETP promotes the atherogenicity of these lipoproteins. In addition, high plasma concentrations of CETP are associated with reduced concentrations of HDL cholesterol. (PMID: 16458590 , 9420339 ).
19:0 Cholesterol esterChEBI
19:0 Cholesteryl esterChEBI
CE 19:0ChEBI
Cholest-5-en-3beta-yl nonadecanoateChEBI
Cholest-5-en-3b-yl nonadecanoateGenerator
Cholest-5-en-3b-yl nonadecanoic acidGenerator
Cholest-5-en-3beta-yl nonadecanoic acidGenerator
Cholest-5-en-3β-yl nonadecanoateGenerator
Cholest-5-en-3β-yl nonadecanoic acidGenerator
Cholesteryl nonadecanoateHMDB
Cholesteryl nonadecanoic acidHMDB
Cholesterol ester(19:0)HMDB
Cholesterol ester(19:0/0:0)HMDB
Cholesterol 1-nonadecanoic acidHMDB
Cholesteryl 1-nonadecanoateHMDB
Cholesteryl 1-nonadecanoic acidHMDB
Cholesterol 1-nonadecanoateHMDB
cholesterol 1-Lipid Annotator
cholesteryl 1-Lipid Annotator
CE(19:0)Lipid Annotator, ChEBI
Chemical FormulaC46H82O2
Average Molecular Weight667.1421
Monoisotopic Molecular Weight666.631481868
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 nonadecanoate
Traditional 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 nonadecanoate
CAS Registry Number25605-90-7
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 DescriptorsNot Available
Physiological effect
Physical Properties
Experimental Molecular Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Water Solubility7.2e-06 g/LALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count24ChemAxon
Refractivity208.01 m³·mol⁻¹ChemAxon
Polarizability91.55 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(19:0)[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)CCCCCCCCCCCCCCCCCC)[C@H](C)CCCC(C)C4238.3Standard polar33892256
CE(19:0)[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)CCCCCCCCCCCCCCCCCC)[C@H](C)CCCC(C)C5021.2Standard non polar33892256
CE(19:0)[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)CCCCCCCCCCCCCCCCCC)[C@H](C)CCCC(C)C4873.5Semi standard non polar33892256

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - CE(19:0) GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-5238059000-b2a05f7b79df6dcd873c2017-09-01Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(19:0) 10V, Positive-QTOFsplash10-014i-1154019000-539c67c40a7cc395ea212017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(19:0) 20V, Positive-QTOFsplash10-00kr-4259021000-e0cb646447bc356cce512017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(19:0) 40V, Positive-QTOFsplash10-0a6r-5249042000-840faa58726ba6947b952017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(19:0) 10V, Negative-QTOFsplash10-014i-0024009000-661629339377798cb5132017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(19:0) 20V, Negative-QTOFsplash10-00kr-0049003000-1f657b8507a159394a512017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(19:0) 40V, Negative-QTOFsplash10-014u-2029000000-bd4cd63c02ddb3af6f572017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(19:0) 10V, Positive-QTOFsplash10-014i-5044019000-3d121ab340b9511218b22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(19:0) 20V, Positive-QTOFsplash10-0a4i-9230011000-2a8f930a8bdf7040a4a62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(19:0) 40V, Positive-QTOFsplash10-0a4i-9310000000-54f1360730e57254185c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(19:0) 10V, Negative-QTOFsplash10-014i-0000009000-1d9f740c9f7491d8b13b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(19:0) 20V, Negative-QTOFsplash10-017i-0091006000-66f1910159c22893f0b12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(19:0) 40V, Negative-QTOFsplash10-056r-8491003000-fbb878092373520d70872021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024052
KNApSAcK IDNot Available
Chemspider ID20118443
KEGG Compound IDC02530
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14274981
PDB IDNot Available
ChEBI ID133745
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
Synthesis ReferenceRizvi, T. Z.; Adil, G. A.; Gondal, H. Y.; Sherazi, H. A. Synthesis and characterization of liquid crystalline cholesterol derivatives. Science International (Lahore) (1997), 9(1), 31-32.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Liebisch G, Binder M, Schifferer R, Langmann T, Schulz B, Schmitz G: High throughput quantification of cholesterol and cholesteryl ester by electrospray ionization tandem mass spectrometry (ESI-MS/MS). Biochim Biophys Acta. 2006 Jan;1761(1):121-8. Epub 2006 Jan 18. [PubMed:16458590 ]
  2. Kuivenhoven JA, Jukema JW, Zwinderman AH, de Knijff P, McPherson R, Bruschke AV, Lie KI, Kastelein JJ: The role of a common variant of the cholesteryl ester transfer protein gene in the progression of coronary atherosclerosis. The Regression Growth Evaluation Statin Study Group. N Engl J Med. 1998 Jan 8;338(2):86-93. [PubMed:9420339 ]


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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Molecular weight:
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:
Uniprot ID:
Molecular weight:
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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