Hmdb loader
Survey
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-09-08 16:45:59 UTC
Update Date2022-11-30 19:24:26 UTC
HMDB IDHMDB0112229
Secondary Accession NumbersNone
Metabolite Identification
Common NameCE(9D4)
DescriptionCE(9D4) is a furan fatty acid ester of cholesterol or simply a cholesteryl ester (CE). Cholesteryl esters are much less polar than free cholesterol and appear to be the preferred form for transport in plasma and for storage. Cholesteryl esters do not contribute to membranes but are packed into intracellular lipid particles or lipoprotein particles. Because of the mechanism of synthesis, plasma cholesteryl esters tend to contain relatively high proportions of C18 fatty acids. Cholesteryl esters are major constituents of the adrenal glands and they also accumulate in the fatty lesions of atherosclerotic plaques. Cholesteryl esters are also major constituents of the lipoprotein particles carried in blood (HDL, LDL, VLDL). The cholesteryl esters in high-density lipoproteins (HDL) are synthesized largely by transfer of fatty acids to cholesterol from position sn-2 (or C-2) of phosphatidylcholine catalyzed by the enzyme lecithin cholesterol acyl transferase (LCAT). The enzyme also promotes the transfer of cholesterol from cells to HDL. As cholesteryl esters accumulate in the lipoprotein core, cholesterol is removed from its surface thus promoting the flow of cholesterol from cell membranes into HDL. This in turn leads to morphological changes in HDL, which grow and become spherical. Subsequently, cholesteryl esters are transferred to the other lipoprotein fractions LDL and VLDL, a reaction catalyzed by cholesteryl ester transfer protein. Another enzyme, acyl-CoA:cholesterol acyltransferase (ACAT) synthesizes cholesteryl esters from CoA esters of fatty acids and cholesterol. Cholesteryl ester hydrolases liberate cholesterol and free fatty acids when required for membrane and lipoprotein formation, and they also provide cholesterol for hormone synthesis in adrenal cells. The shorthand notation for CE(9D4) refers to the furan fatty acid's 9-carbon carboxyalkyl moiety, the dimethyl substitutions in the 3- and 4-positions of its furan moiety, and its 4-carbon alkyl moiety.
Structure
Data?1563873231
Synonyms
ValueSource
CE(DiMe(9,4))SMPDB, HMDB
9D4 cholesteryl esterSMPDB, HMDB
DiMe(9,4) cholesteryl esterSMPDB, HMDB
CE(9D4)SMPDB
2,15-Dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl 9-(5-butyl-3,4-dimethylfuran-2-yl)nonanoic acidGenerator, HMDB
2,15-Dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0,.0,]heptadec-7-en-5-yl 9-(5-butyl-3,4-dimethylfuran-2-yl)nonanoic acidGenerator
Chemical FormulaC46H76O3
Average Molecular Weight677.111
Monoisotopic Molecular Weight676.579446307
IUPAC Name2,15-dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl 9-(5-butyl-3,4-dimethylfuran-2-yl)nonanoate
Traditional Name2,15-dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl 9-(5-butyl-3,4-dimethylfuran-2-yl)nonanoate
CAS Registry NumberNot Available
SMILES
CCCCC1=C(C)C(C)=C(CCCCCCCCC(=O)OC2CCC3(C)C4CCC5(C)C(CCC5C4CC=C3C2)C(C)CCCC(C)C)O1
InChI Identifier
InChI=1S/C46H76O3/c1-9-10-20-42-34(5)35(6)43(49-42)21-15-13-11-12-14-16-22-44(47)48-37-27-29-45(7)36(31-37)23-24-38-40-26-25-39(33(4)19-17-18-32(2)3)46(40,8)30-28-41(38)45/h23,32-33,37-41H,9-22,24-31H2,1-8H3
InChI KeyQKCKJTMSKBRULS-UHFFFAOYSA-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
  • Furanoid fatty acid
  • Fatty acyl
  • Furan
  • Heteroaromatic compound
  • Carboxylic acid ester
  • Organoheterocyclic compound
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
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
logP9.87ALOGPS
logP14.04ChemAxon
logS-5.8ALOGPS
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area39.44 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity208.2 m³·mol⁻¹ChemAxon
Polarizability88.62 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+256.30431661259
DarkChem[M-H]-253.04231661259
DeepCCS[M+H]+279.17530932474
DeepCCS[M-H]-276.7830932474
DeepCCS[M-2H]-309.66630932474
DeepCCS[M+Na]+285.08830932474
AllCCS[M+H]+271.732859911
AllCCS[M+H-H2O]+271.332859911
AllCCS[M+NH4]+272.032859911
AllCCS[M+Na]+272.132859911
AllCCS[M-H]-218.532859911
AllCCS[M+Na-2H]-224.732859911
AllCCS[M+HCOO]-231.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CE(9D4)CCCCC1=C(C)C(C)=C(CCCCCCCCC(=O)OC2CCC3(C)C4CCC5(C)C(CCC5C4CC=C3C2)C(C)CCCC(C)C)O14659.3Standard polar33892256
CE(9D4)CCCCC1=C(C)C(C)=C(CCCCCCCCC(=O)OC2CCC3(C)C4CCC5(C)C(CCC5C4CC=C3C2)C(C)CCCC(C)C)O14827.0Standard non polar33892256
CE(9D4)CCCCC1=C(C)C(C)=C(CCCCCCCCC(=O)OC2CCC3(C)C4CCC5(C)C(CCC5C4CC=C3C2)C(C)CCCC(C)C)O14856.3Semi standard non polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(9D4) 10V, Positive-QTOFsplash10-00or-1044009000-e4e5f73d7f444e0dceb32019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(9D4) 20V, Positive-QTOFsplash10-014u-4239002000-c9412a6ced32bdd3baed2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(9D4) 40V, Positive-QTOFsplash10-0a6r-5119001000-d194aa79d57571ff1d5e2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(9D4) 10V, Negative-QTOFsplash10-004r-0015009000-3bdec81f9e8cfeaabfa62019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(9D4) 20V, Negative-QTOFsplash10-000i-0129003000-3a193c2bd16df684f4e52019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(9D4) 40V, Negative-QTOFsplash10-00kr-1119000000-d4bc8c5265273f1cb9052019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(9D4) 10V, Positive-QTOFsplash10-0170-1139007000-ebcec474678f3141c0412021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(9D4) 20V, Positive-QTOFsplash10-0aba-9561012000-c5b5d0aa2e8d13a8d5a62021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(9D4) 40V, Positive-QTOFsplash10-0abl-3910010000-f117ec3baa8e7f1edbb62021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(9D4) 10V, Negative-QTOFsplash10-004i-0002009000-6c2dac893b423dc8fe3c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(9D4) 20V, Negative-QTOFsplash10-004i-0003009000-3494dec88a6393505da42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CE(9D4) 40V, Negative-QTOFsplash10-000i-2910104000-039fe627c92edb2be6052021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131819672
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)Not Available
General References
  1. Vetter W, Wendlinger C (2013). Furan fatty acids – valuable minor fatty acids in food. Lipid Technology.
  2. Wendlinger C, Hammann S, Vetter W (2016). Detailed Study of Furan Fatty Acids in Total Lipids and the Cholesteryl Ester Fraction of Fish Liver. Food Analytical Methods.