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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:25:07 UTC
Update Date2022-03-07 02:54:51 UTC
HMDB IDHMDB0036293
Secondary Accession Numbers
  • HMDB36293
Metabolite Identification
Common NameCholesteryl ferulate
DescriptionCholesteryl ferulate belongs to the class of organic compounds known as cholesteryl esters. Cholesteryl esters are compounds containing an esterified cholestane moiety. Cholesteryl ferulate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862851
Synonyms
ValueSource
Cholesteryl ferulic acidGenerator
2,15-Dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acidGenerator
Chemical FormulaC37H54O4
Average Molecular Weight562.8223
Monoisotopic Molecular Weight562.402210216
IUPAC Name2,15-dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Traditional Name2,15-dimethyl-14-(6-methylheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
CAS Registry Number164453-91-2
SMILES
COC1=CC(\C=C\C(=O)OC2CCC3(C)C4CCC5(C)C(CCC5C4CC=C3C2)C(C)CCCC(C)C)=CC=C1O
InChI Identifier
InChI=1S/C37H54O4/c1-24(2)8-7-9-25(3)30-14-15-31-29-13-12-27-23-28(18-20-36(27,4)32(29)19-21-37(30,31)5)41-35(39)17-11-26-10-16-33(38)34(22-26)40-6/h10-12,16-17,22,24-25,28-32,38H,7-9,13-15,18-21,23H2,1-6H3/b17-11+
InChI KeyCPBQNAKTSMCPNH-GZTJUZNOSA-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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point165 - 166 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.0e-05 g/LALOGPS
logP8.27ALOGPS
logP9.69ChemAxon
logS-7.7ALOGPS
pKa (Strongest Acidic)9.87ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity168.63 m³·mol⁻¹ChemAxon
Polarizability69.24 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
DeepCCS[M+H]+236.4730932474
DeepCCS[M-H]-234.07430932474
DeepCCS[M-2H]-266.95830932474
DeepCCS[M+Na]+242.38330932474
AllCCS[M+H]+244.032859911
AllCCS[M+H-H2O]+242.932859911
AllCCS[M+NH4]+245.032859911
AllCCS[M+Na]+245.332859911
AllCCS[M-H]-225.632859911
AllCCS[M+Na-2H]-229.232859911
AllCCS[M+HCOO]-233.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Cholesteryl ferulateCOC1=CC(\C=C\C(=O)OC2CCC3(C)C4CCC5(C)C(CCC5C4CC=C3C2)C(C)CCCC(C)C)=CC=C1O4615.8Standard polar33892256
Cholesteryl ferulateCOC1=CC(\C=C\C(=O)OC2CCC3(C)C4CCC5(C)C(CCC5C4CC=C3C2)C(C)CCCC(C)C)=CC=C1O4204.6Standard non polar33892256
Cholesteryl ferulateCOC1=CC(\C=C\C(=O)OC2CCC3(C)C4CCC5(C)C(CCC5C4CC=C3C2)C(C)CCCC(C)C)=CC=C1O4587.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cholesteryl ferulate,1TMS,isomer #1COC1=CC(/C=C/C(=O)OC2CCC3(C)C(=CCC4C3CCC3(C)C(C(C)CCCC(C)C)CCC43)C2)=CC=C1O[Si](C)(C)C4576.6Semi standard non polar33892256
Cholesteryl ferulate,1TBDMS,isomer #1COC1=CC(/C=C/C(=O)OC2CCC3(C)C(=CCC4C3CCC3(C)C(C(C)CCCC(C)C)CCC43)C2)=CC=C1O[Si](C)(C)C(C)(C)C4814.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cholesteryl ferulate GC-MS (Non-derivatized) - 70eV, Positivesplash10-004m-1309150000-84e753ca0e0bb2b227932017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cholesteryl ferulate GC-MS (1 TMS) - 70eV, Positivesplash10-06fv-2019016000-c08e862c68501d52a4bb2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cholesteryl ferulate GC-MS ("Cholesteryl ferulate,1TMS,#1" TMS) - 70eV, PositiveNot Available2021-10-14Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cholesteryl ferulate GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholesteryl ferulate 10V, Positive-QTOFsplash10-03fr-0505190000-5030b3305d766d4ab37d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholesteryl ferulate 20V, Positive-QTOFsplash10-004r-2709110000-fb6e1196775143649feb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholesteryl ferulate 40V, Positive-QTOFsplash10-0a6r-2209000000-15cb14f282407bc0d4e62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholesteryl ferulate 10V, Negative-QTOFsplash10-03di-0204090000-55b49640eb7d5a53eb122016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholesteryl ferulate 20V, Negative-QTOFsplash10-000i-0709240000-2d4330c4248b6ae2a6f82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholesteryl ferulate 40V, Negative-QTOFsplash10-0170-1409000000-9d5839a90277ac432f722016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholesteryl ferulate 10V, Positive-QTOFsplash10-03di-1001190000-ed2c3d6eef859762a2322021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholesteryl ferulate 20V, Positive-QTOFsplash10-0nb9-9144420000-2c79e16b35fe65a1cc822021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholesteryl ferulate 40V, Positive-QTOFsplash10-0a4i-7953200000-35b5f3f0f6841f73c3cd2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholesteryl ferulate 10V, Negative-QTOFsplash10-03di-0000090000-665c37b4d9e659cc87dc2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholesteryl ferulate 20V, Negative-QTOFsplash10-000i-0904430000-223a8e5bf3d4131fdd182021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cholesteryl ferulate 40V, Negative-QTOFsplash10-0a4i-1701390000-45770c76d015b22ef5e12021-09-22Wishart 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 IDFDB015159
KNApSAcK IDNot Available
Chemspider ID15842133
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound22375086
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. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.