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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:47:59 UTC
Update Date2022-03-07 02:56:54 UTC
HMDB IDHMDB0041146
Secondary Accession Numbers
  • HMDB41146
Metabolite Identification
Common NameFeruloyl-beta-sitosterol
Description7-Pentacosanone belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. 7-Pentacosanone is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563863629
Synonyms
ValueSource
3-(4-Hydroxy-3-methoxyphenyl)-2-propenoate(3beta)-stigmast-5-en-3-olHMDB
beta-Sitosterol ferulateHMDB
beta-Sitosterol, 4-hydroxy-3-methoxycinnamate (7ci)HMDB
beta-Sitosteryl ferulateHMDB
Ferulic acid beta-sitosterol esterHMDB
Feruloyl-b-sitosterolHMDB, Generator
Sitosterol ferulateHMDB
(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5-Ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acidGenerator
Feruloyl-β-sitosterolGenerator
Chemical FormulaC39H58O4
Average Molecular Weight590.8754
Monoisotopic Molecular Weight590.433510344
IUPAC Name(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Traditional Name(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
CAS Registry Number4952-28-7
SMILES
CC[C@H](CC[C@@H](C)[C@@]1([H])CC[C@@]2([H])[C@]3([H])CC=C4C[C@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)OC(=O)\C=C\C1=CC=C(O)C(OC)=C1)C(C)C
InChI Identifier
InChI=1S/C39H58O4/c1-8-28(25(2)3)12-9-26(4)32-15-16-33-31-14-13-29-24-30(19-21-38(29,5)34(31)20-22-39(32,33)6)43-37(41)18-11-27-10-17-35(40)36(23-27)42-7/h10-11,13,17-18,23,25-26,28,30-34,40H,8-9,12,14-16,19-22,24H2,1-7H3/b18-11+/t26-,28-,30+,31+,32-,33+,34+,38+,39-/m1/s1
InChI KeyROUSJNZGMHNWOS-OJJOFZOASA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentKetones
Alternative Parents
Substituents
  • Ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point131 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility7.3e-06 g/LALOGPS
logP8.42ALOGPS
logP10.42ChemAxon
logS-7.9ALOGPS
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 Count11ChemAxon
Refractivity177.78 m³·mol⁻¹ChemAxon
Polarizability73.28 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-2H]-272.43330932474
DeepCCS[M+Na]+246.2430932474
AllCCS[M+H]+249.832859911
AllCCS[M+H-H2O]+248.832859911
AllCCS[M+NH4]+250.732859911
AllCCS[M+Na]+250.932859911
AllCCS[M-H]-227.132859911
AllCCS[M+Na-2H]-231.232859911
AllCCS[M+HCOO]-235.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Feruloyl-beta-sitosterolCC[C@H](CC[C@@H](C)[C@@]1([H])CC[C@@]2([H])[C@]3([H])CC=C4C[C@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)OC(=O)\C=C\C1=CC=C(O)C(OC)=C1)C(C)C4744.8Standard polar33892256
Feruloyl-beta-sitosterolCC[C@H](CC[C@@H](C)[C@@]1([H])CC[C@@]2([H])[C@]3([H])CC=C4C[C@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)OC(=O)\C=C\C1=CC=C(O)C(OC)=C1)C(C)C4499.0Standard non polar33892256
Feruloyl-beta-sitosterolCC[C@H](CC[C@@H](C)[C@@]1([H])CC[C@@]2([H])[C@]3([H])CC=C4C[C@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)OC(=O)\C=C\C1=CC=C(O)C(OC)=C1)C(C)C4877.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Feruloyl-beta-sitosterol,1TMS,isomer #1CC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](OC(=O)/C=C/C5=CC=C(O[Si](C)(C)C)C(OC)=C5)CC[C@]4(C)[C@H]3CC[C@@]21C)C(C)C4716.5Semi standard non polar33892256
Feruloyl-beta-sitosterol,1TBDMS,isomer #1CC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](OC(=O)/C=C/C5=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C5)CC[C@]4(C)[C@H]3CC[C@@]21C)C(C)C4963.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Feruloyl-beta-sitosterol GC-MS (Non-derivatized) - 70eV, Positivesplash10-01ta-3409180000-4214b2ad9cd6070699bf2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Feruloyl-beta-sitosterol GC-MS (1 TMS) - 70eV, Positivesplash10-0002-4127019000-64981a2f9965ffb3dd822017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Feruloyl-beta-sitosterol GC-MS ("Feruloyl-beta-sitosterol,1TMS,#1" TMS) - 70eV, PositiveNot Available2021-10-14Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Feruloyl-beta-sitosterol 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 - Feruloyl-beta-sitosterol 10V, Positive-QTOFsplash10-002g-0702390000-990b833717748ff767632017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Feruloyl-beta-sitosterol 20V, Positive-QTOFsplash10-000b-4916320000-656f22377af96a40e63d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Feruloyl-beta-sitosterol 40V, Positive-QTOFsplash10-05a2-7529110000-1c5c17cbb758934fe34a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Feruloyl-beta-sitosterol 10V, Negative-QTOFsplash10-000i-0100390000-cf4c910ea4692ab94eaf2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Feruloyl-beta-sitosterol 20V, Negative-QTOFsplash10-03dr-0601930000-86ee614465d16dd4a1732017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Feruloyl-beta-sitosterol 40V, Negative-QTOFsplash10-03dj-3509700000-6b94d0c64ef79d89f8402017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Feruloyl-beta-sitosterol 10V, Negative-QTOFsplash10-000i-0000090000-8a5848173126c99a2a452021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Feruloyl-beta-sitosterol 20V, Negative-QTOFsplash10-000i-0900150000-b2f99abbb951a011dca72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Feruloyl-beta-sitosterol 40V, Negative-QTOFsplash10-001j-0900110000-1049bb1da9bde22a55192021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Feruloyl-beta-sitosterol 10V, Positive-QTOFsplash10-02td-0315290000-74f26b16e76593df853f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Feruloyl-beta-sitosterol 20V, Positive-QTOFsplash10-0301-2425390000-bed9bdd72a17d2b1592c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Feruloyl-beta-sitosterol 40V, Positive-QTOFsplash10-0002-6932010000-8e71b6f106239c3236e82021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • 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 IDFDB020744
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound54551687
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.