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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:34:55 UTC
Update Date2022-03-07 02:52:26 UTC
HMDB IDHMDB0030123
Secondary Accession Numbers
  • HMDB30123
Metabolite Identification
Common Name(3beta,5alpha,24S)-Ergost-8(14)-en-3-ol
Description.alpha.-Ergostenol belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. .alpha.-Ergostenol is possibly neutral.
Structure
Data?1563861940
Synonyms
ValueSource
(24S)-beta-Methyl cholest-8(14)-enolHMDB
5alpha-Ergost-8(14)-en-3beta-olHMDB
alpha-ErgostenolHMDB
(3b,5a,24S)-Ergost-8(14)-en-3-olGenerator
(3Β,5α,24S)-ergost-8(14)-en-3-olGenerator
Chemical FormulaC28H48O
Average Molecular Weight400.6801
Monoisotopic Molecular Weight400.370516158
IUPAC Name14-(5,6-dimethylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-10-en-5-ol
Traditional Nameα-ergostenol
CAS Registry Number632-32-6
SMILES
CC(C)C(C)CCC(C)C1CCC2=C3CCC4CC(O)CCC4(C)C3CCC12C
InChI Identifier
InChI=1S/C28H48O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h18-22,24,26,29H,7-17H2,1-6H3
InChI KeyAWYDNKRGSOPYQB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassErgostane steroids
Direct ParentErgosterols and derivatives
Alternative Parents
Substituents
  • Ergosterol-skeleton
  • Hydroxysteroid
  • 3-hydroxysteroid
  • 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
ProcessNot Available
RoleNot Available
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 Solubility0.00018 g/LALOGPS
logP6.68ALOGPS
logP7.36ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)18.3ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity124.9 m³·mol⁻¹ChemAxon
Polarizability50.87 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]+193.02231661259
DarkChem[M-H]-191.02631661259
DeepCCS[M-2H]-234.61230932474
DeepCCS[M+Na]+209.96530932474
AllCCS[M+H]+207.032859911
AllCCS[M+H-H2O]+204.932859911
AllCCS[M+NH4]+208.932859911
AllCCS[M+Na]+209.432859911
AllCCS[M-H]-204.832859911
AllCCS[M+Na-2H]-206.832859911
AllCCS[M+HCOO]-209.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(3beta,5alpha,24S)-Ergost-8(14)-en-3-olCC(C)C(C)CCC(C)C1CCC2=C3CCC4CC(O)CCC4(C)C3CCC12C2518.5Standard polar33892256
(3beta,5alpha,24S)-Ergost-8(14)-en-3-olCC(C)C(C)CCC(C)C1CCC2=C3CCC4CC(O)CCC4(C)C3CCC12C3185.6Standard non polar33892256
(3beta,5alpha,24S)-Ergost-8(14)-en-3-olCC(C)C(C)CCC(C)C1CCC2=C3CCC4CC(O)CCC4(C)C3CCC12C3238.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(3beta,5alpha,24S)-Ergost-8(14)-en-3-ol,1TMS,isomer #1CC(C)C(C)CCC(C)C1CCC2=C3CCC4CC(O[Si](C)(C)C)CCC4(C)C3CCC21C3283.9Semi standard non polar33892256
(3beta,5alpha,24S)-Ergost-8(14)-en-3-ol,1TBDMS,isomer #1CC(C)C(C)CCC(C)C1CCC2=C3CCC4CC(O[Si](C)(C)C(C)(C)C)CCC4(C)C3CCC21C3515.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (3beta,5alpha,24S)-Ergost-8(14)-en-3-ol GC-MS (Non-derivatized) - 70eV, Positivesplash10-007c-2019000000-fb6e1388226197a489672017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (3beta,5alpha,24S)-Ergost-8(14)-en-3-ol GC-MS (1 TMS) - 70eV, Positivesplash10-0a4l-4104900000-551ea4dad41d2e77fec32017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (3beta,5alpha,24S)-Ergost-8(14)-en-3-ol 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 - (3beta,5alpha,24S)-Ergost-8(14)-en-3-ol 10V, Positive-QTOFsplash10-0ue9-1019500000-5353284a7300983eea492015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3beta,5alpha,24S)-Ergost-8(14)-en-3-ol 20V, Positive-QTOFsplash10-00lj-7149100000-2880b60c07ccfea714fd2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3beta,5alpha,24S)-Ergost-8(14)-en-3-ol 40V, Positive-QTOFsplash10-000i-9174000000-e82757d064c3194864cd2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3beta,5alpha,24S)-Ergost-8(14)-en-3-ol 10V, Negative-QTOFsplash10-0002-0009000000-49c8b538af415d794fb62015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3beta,5alpha,24S)-Ergost-8(14)-en-3-ol 20V, Negative-QTOFsplash10-0002-0009000000-9e5bed1d26edaeebdeff2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3beta,5alpha,24S)-Ergost-8(14)-en-3-ol 40V, Negative-QTOFsplash10-00lr-3019000000-5f0717edf225f526e3882015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3beta,5alpha,24S)-Ergost-8(14)-en-3-ol 10V, Negative-QTOFsplash10-0002-0009000000-e5e9af9914ac05de1a5c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3beta,5alpha,24S)-Ergost-8(14)-en-3-ol 20V, Negative-QTOFsplash10-0002-0009000000-e5e9af9914ac05de1a5c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3beta,5alpha,24S)-Ergost-8(14)-en-3-ol 40V, Negative-QTOFsplash10-0002-0009000000-bbd1f9088923fde32d112021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3beta,5alpha,24S)-Ergost-8(14)-en-3-ol 10V, Positive-QTOFsplash10-0udi-2014900000-8b7da0d52a5e1e6d3d412021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3beta,5alpha,24S)-Ergost-8(14)-en-3-ol 20V, Positive-QTOFsplash10-0a4i-9132000000-f867717e6830be585ef92021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (3beta,5alpha,24S)-Ergost-8(14)-en-3-ol 40V, Positive-QTOFsplash10-0a4l-9610000000-9a4ebd4aac962a1a28472021-09-25Wishart 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 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 Compound312796
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.