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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:14:51 UTC
Update Date2022-03-07 02:54:05 UTC
HMDB IDHMDB0034407
Secondary Accession Numbers
  • HMDB34407
Metabolite Identification
Common NamePeposterol
DescriptionPeposterol belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. Thus, peposterol is considered to be a sterol lipid molecule. Peposterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563862559
Synonyms
ValueSource
Peposterol (7,24-stigmastadienol) acetateHMDB
Chemical FormulaC29H48O
Average Molecular Weight412.6908
Monoisotopic Molecular Weight412.370516158
IUPAC Name14-(5-ethyl-6-methylhept-5-en-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-5-ol
Traditional Name14-(5-ethyl-6-methylhept-5-en-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-5-ol
CAS Registry Number50632-69-4
SMILES
CCC(CCC(C)C1CCC2C3=CCC4CC(O)CCC4(C)C3CCC12C)=C(C)C
InChI Identifier
InChI=1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h11,20,22-23,25-27,30H,7-10,12-18H2,1-6H3
InChI KeySTLJXSQSUAPXFX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassStigmastanes and derivatives
Direct ParentStigmastanes and derivatives
Alternative Parents
Substituents
  • Triterpenoid
  • Stigmastane-skeleton
  • Hydroxysteroid
  • 3-hydroxysteroid
  • 3-hydroxy-delta-7-steroid
  • Delta-7-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point130 - 131 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00039 g/LALOGPS
logP7.33ALOGPS
logP7.4ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)18.36ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity130.35 m³·mol⁻¹ChemAxon
Polarizability52.73 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+198.80431661259
DarkChem[M-H]-198.8131661259
DeepCCS[M-2H]-242.47330932474
DeepCCS[M+Na]+217.98130932474
AllCCS[M+H]+210.232859911
AllCCS[M+H-H2O]+208.232859911
AllCCS[M+NH4]+212.032859911
AllCCS[M+Na]+212.632859911
AllCCS[M-H]-208.532859911
AllCCS[M+Na-2H]-210.532859911
AllCCS[M+HCOO]-212.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PeposterolCCC(CCC(C)C1CCC2C3=CCC4CC(O)CCC4(C)C3CCC12C)=C(C)C2815.9Standard polar33892256
PeposterolCCC(CCC(C)C1CCC2C3=CCC4CC(O)CCC4(C)C3CCC12C)=C(C)C3327.4Standard non polar33892256
PeposterolCCC(CCC(C)C1CCC2C3=CCC4CC(O)CCC4(C)C3CCC12C)=C(C)C3402.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Peposterol,1TMS,isomer #1CCC(CCC(C)C1CCC2C3=CCC4CC(O[Si](C)(C)C)CCC4(C)C3CCC21C)=C(C)C3477.5Semi standard non polar33892256
Peposterol,1TBDMS,isomer #1CCC(CCC(C)C1CCC2C3=CCC4CC(O[Si](C)(C)C(C)(C)C)CCC4(C)C3CCC21C)=C(C)C3697.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Peposterol GC-MS (Non-derivatized) - 70eV, Positivesplash10-001j-1019000000-79ea4750d14bdb4e661b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Peposterol GC-MS (1 TMS) - 70eV, Positivesplash10-0avi-3104900000-ca6da4ea7163554f02c12017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Peposterol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Peposterol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Peposterol 10V, Positive-QTOFsplash10-01ot-1019500000-26e5b6444674339baff82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Peposterol 20V, Positive-QTOFsplash10-0002-4149100000-f910274f4ab4fb86d6542016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Peposterol 40V, Positive-QTOFsplash10-0002-8193000000-94b12839f431ddd07d562016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Peposterol 10V, Negative-QTOFsplash10-03di-0002900000-0ed8ac6a943cb547b3822016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Peposterol 20V, Negative-QTOFsplash10-03di-0006900000-6c846dd0831d3324de5a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Peposterol 40V, Negative-QTOFsplash10-0002-3009000000-6b1023c268745791be712016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Peposterol 10V, Negative-QTOFsplash10-03di-0000900000-363450e12a0ea926276e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Peposterol 20V, Negative-QTOFsplash10-03di-0000900000-48f4c12668657bee9e922021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Peposterol 40V, Negative-QTOFsplash10-08fu-0019600000-b8012ef4cec64b00a9912021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Peposterol 10V, Positive-QTOFsplash10-03di-3119700000-ffaa95ca3f90b1e797de2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Peposterol 20V, Positive-QTOFsplash10-02ai-9124100000-c785277e6675d906a3aa2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Peposterol 40V, Positive-QTOFsplash10-06rx-9511000000-bb17299ba4bc4142515d2021-09-22Wishart 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 IDFDB012797
KNApSAcK IDNot Available
Chemspider ID4479223
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5321504
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.