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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-09-05 15:23:44 UTC
Update Date2022-03-07 02:49:32 UTC
HMDB IDHMDB0006728
Secondary Accession Numbers
  • HMDB06728
Metabolite Identification
Common NameCE(24:1(15Z))
DescriptionCholesteryl nervonic 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). Placental membrane changes in permeability to water, urea and mannitol in intrauterine growth restriction are related to changes in cholesterol fatty acid content of the membranes with a predominance of saturated fatty acid species such as nervonic acid. Nervonic acid may have preventive effects on obesity-related metabolic disorders. Lower levels of nervonic acid are found in all plasma lipid fractions from infants fed formula compared with those in the human milk-fed infants, irrespective of the source of the formula supplement. (PMID: 16394593 , 10446293 , 15051839 ).
Structure
Data?1582752402
Synonyms
ValueSource
24:1 Cholesterol esterHMDB
Cholest-5-en-3beta-yl (15Z-tetracosenoateHMDB
Cholest-5-en-3beta-yl (15Z-tetracosenoate)HMDB
Cholest-5-en-3beta-yl (15Z-tetracosenoic acidHMDB
Cholesteryl nervonic acidHMDB
Cholesterol 1-nervonoateHMDB
24:1(15Z) Cholesterol esterHMDB
Cholesterol ester(24:1/0:0)HMDB
Cholesteryl 1-nervonoateHMDB
CE(24:1)HMDB
CE(24:1/0:0)HMDB
Cholesterol ester(24:1)HMDB
Cholesteryl 1-(15Z-tetracosanoate)HMDB
1-Nervonoyl-cholesterolHMDB
Cholesterol 1-nervonoic acidHMDB
Cholesterol 1-(15Z-tetracosanoic acid)HMDB
Cholesterol 1-(15Z-tetracosanoate)HMDB
Cholesteryl 1-(15Z-tetracosanoic acid)HMDB
1-(15Z-Tetracosanoyl)-cholesterolHMDB
Cholesteryl 1-nervonoic acidHMDB
CE(24:1(15Z))Lipid Annotator
(1S,2R,5S,10S,11S,14R,15R)-2,15-Dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl (15Z)-tetracos-15-enoic acidGenerator
Cholesteryl 15-tetracosenoateMeSH
Cholesteryl nervonateMeSH
Chemical FormulaC51H90O2
Average Molecular Weight735.2591
Monoisotopic Molecular Weight734.694082124
IUPAC Name(1S,2R,5S,10S,11S,14R,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 (15Z)-tetracos-15-enoate
Traditional Name(1S,2R,5S,10S,11S,14R,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 (15Z)-tetracos-15-enoate
CAS Registry Number60758-73-8
SMILES
CCCCCCCC\C=C/CCCCCCCCCCCCCC(=O)O[C@H]1CC[C@@]2(C)C(=CC[C@@]3([H])[C@]4([H])CC[C@]([H])([C@H](C)CCCC(C)C)[C@@]4(C)CC[C@]23[H])C1
InChI Identifier
InChI=1S/C51H90O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27-31-49(52)53-44-36-38-50(5)43(40-44)32-33-45-47-35-34-46(42(4)30-28-29-41(2)3)51(47,6)39-37-48(45)50/h14-15,32,41-42,44-48H,7-13,16-31,33-40H2,1-6H3/b15-14-/t42-,44+,45+,46-,47+,48+,50+,51-/m1/s1
InChI KeyPUKCXSHDVCMMAN-FYGHJIOESA-N
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
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

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility7.1e-06 g/LALOGPS
logP11.19ALOGPS
logP17.23ChemAxon
logS-8ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count28ChemAxon
Refractivity232.13 m³·mol⁻¹ChemAxon
Polarizability100.63 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-319.23730932474
DeepCCS[M+Na]+293.00930932474
AllCCS[M+H]+274.232859911
AllCCS[M+H-H2O]+274.132859911
AllCCS[M+NH4]+274.432859911
AllCCS[M+Na]+274.432859911
AllCCS[M-H]-235.332859911
AllCCS[M+Na-2H]-242.832859911
AllCCS[M+HCOO]-250.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CE(24:1(15Z))CCCCCCCC\C=C/CCCCCCCCCCCCCC(=O)O[C@H]1CC[C@@]2(C)C(=CC[C@@]3([H])[C@]4([H])CC[C@]([H])([C@H](C)CCCC(C)C)[C@@]4(C)CC[C@]23[H])C14598.4Standard polar33892256
CE(24:1(15Z))CCCCCCCC\C=C/CCCCCCCCCCCCCC(=O)O[C@H]1CC[C@@]2(C)C(=CC[C@@]3([H])[C@]4([H])CC[C@]([H])([C@H](C)CCCC(C)C)[C@@]4(C)CC[C@]23[H])C15512.7Standard non polar33892256
CE(24:1(15Z))CCCCCCCC\C=C/CCCCCCCCCCCCCC(=O)O[C@H]1CC[C@@]2(C)C(=CC[C@@]3([H])[C@]4([H])CC[C@]([H])([C@H](C)CCCC(C)C)[C@@]4(C)CC[C@]23[H])C15324.3Semi standard non polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(24:1(15Z)) 10V, Positive-QTOFsplash10-000i-1009002600-9d682dff9878edb14b072017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(24:1(15Z)) 20V, Positive-QTOFsplash10-05ts-2109002000-75ce5a7114200ce9a9212017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(24:1(15Z)) 40V, Positive-QTOFsplash10-0adi-3109011000-32a423e507a1e9bacc8b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(24:1(15Z)) 10V, Negative-QTOFsplash10-001i-0006000900-ee0f4056fa6d713a07b12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(24:1(15Z)) 20V, Negative-QTOFsplash10-000i-0009000200-4a7223d49d992c772e612017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(24:1(15Z)) 40V, Negative-QTOFsplash10-014u-2009000000-1cd08d987b36c5f423df2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(24:1(15Z)) 10V, Positive-QTOFsplash10-00kr-4019003700-1d207d43b691ddc29b702021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(24:1(15Z)) 20V, Positive-QTOFsplash10-0a5c-9112011100-ec555fcbb57b597d15052021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(24:1(15Z)) 40V, Positive-QTOFsplash10-0a5c-9100000000-09662d0bbaf6e15585b92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(24:1(15Z)) 10V, Negative-QTOFsplash10-001i-0001000900-4166e9b914301c1ff4ef2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(24:1(15Z)) 20V, Negative-QTOFsplash10-001i-0007000900-cef6799a5d47b1b0bdcd2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(24:1(15Z)) 40V, Negative-QTOFsplash10-0541-6209303400-ffee5e8dccf09b719fcd2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
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 IDFDB024044
KNApSAcK IDNot Available
Chemspider ID23621210
KEGG Compound IDC02530
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53477888
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Oda E, Hatada K, Kimura J, Aizawa Y, Thanikachalam PV, Watanabe K: Relationships between serum unsaturated fatty acids and coronary risk factors: negative relations between nervonic acid and obesity-related risk factors. Int Heart J. 2005 Nov;46(6):975-85. [PubMed:16394593 ]
  2. Sala-Vila A, Castellote AI, Campoy C, Rivero M, Rodriguez-Palmero M, Lopez-Sabater MC: The source of long-chain PUFA in formula supplements does not affect the fatty acid composition of plasma lipids in full-term infants. J Nutr. 2004 Apr;134(4):868-73. [PubMed:15051839 ]
  3. Powell TL, Jansson T, Illsley NP, Wennergren M, Korotkova M, Strandvik B: Composition and permeability of syncytiotrophoblast plasma membranes in pregnancies complicated by intrauterine growth restriction. Biochim Biophys Acta. 1999 Aug 20;1420(1-2):86-94. [PubMed:10446293 ]

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