5-dehydro episterol (CHEM042065)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:48:48 UTC
Update Date2016-11-09 01:22:36 UTC
Accession NumberCHEM042065
Identification
Common Name5-dehydro episterol
ClassSmall Molecule
DescriptionThis compound belongs to the family of Ergosterols and Derivatives. These are steroids containing ergosta-5,7,22-trien-3β-ol or a derivative thereof, which is based on the 3β-hydroxylated ergostane skeleton
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Ergosta-5,7,24(28)-trien-3beta-olHMDB
Ergosta-5,7,24(28)-trien-3b-olHMDB
Ergosta-5,7,24(28)-trien-3β-olHMDB
Chemical FormulaC28H44O
Average Molecular Mass396.648 g/mol
Monoisotopic Mass396.339 g/mol
CAS Registry NumberNot Available
IUPAC Name(2R,5S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-7,9-dien-5-ol
Traditional Name(2R,5S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-7,9-dien-5-ol
SMILESCC(C)C(=C)CC[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]12C
InChI IdentifierInChI=1S/C28H44O/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/h9-10,18,20,22,24-26,29H,3,7-8,11-17H2,1-2,4-6H3/t20-,22+,24-,25+,26?,27+,28-/m1/s1
InChI KeyZEPNVCGPJXYABB-CPGDAPNVSA-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
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxy-delta-7-steroid
  • 3-hydroxysteroid
  • Hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • 3-beta-hydroxysteroid
  • Delta-7-steroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0006 g/LALOGPS
logP7.64ALOGPS
logP6.65ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)18.27ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity125.79 m³·mol⁻¹ChemAxon
Polarizability50.59 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00lr-1019000000-03ea14fa853821e4638aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0udi-2005900000-497de544ef5aa67f52beSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-0019000000-ec4a863acd6783c7db80Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0032-6159000000-2fa2d066e8ea1504f297Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-8094000000-e86c8d11fb643c8a6bd4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-03506c1fb18d95fe82baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0009000000-d3d2383799c5587a29c9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-2019000000-180b0828fbb1ad3d49d9Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0060404
FooDB IDFDB030564
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID30792038
ChEBI ID80095
PubChem Compound ID46173808
Kegg Compound IDC15778
YMDB IDYMDB16321
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011.
2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
3. 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.
4. 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.
5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
6. The lipid handbook with CD-ROM