gamma-Sitosterol (CHEM028055)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 00:11:19 UTC
Update Date2016-11-09 01:18:35 UTC
Accession NumberCHEM028055
Identification
Common Namegamma-Sitosterol
ClassSmall Molecule
DescriptionA member of the class of phytosterols that is poriferast-5-ene carrying a beta-hydroxy substituent at position 3.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(3beta,24S)-Stigmast-5-en-3-olChEBI
22,23-DihydroporiferasterolChEBI
24-Ethylcholest-5-en-3 beta-olChEBI
24beta-Ethyl-5-cholesten-3beta-olChEBI
24beta-EthylcholesterolChEBI
24S-Ethylcholest-5-en-3beta-olChEBI
beta-DihydrofucosterolChEBI
gamma-SitosterolChEBI
Poriferast-5-en-3beta-olChEBI
(3b,24S)-Stigmast-5-en-3-olGenerator
(3Β,24S)-stigmast-5-en-3-olGenerator
24-Ethylcholest-5-en-3 b-olGenerator
24-Ethylcholest-5-en-3 β-olGenerator
24b-Ethyl-5-cholesten-3b-olGenerator
24Β-ethyl-5-cholesten-3β-olGenerator
24b-EthylcholesterolGenerator
24Β-ethylcholesterolGenerator
24S-Ethylcholest-5-en-3b-olGenerator
24S-Ethylcholest-5-en-3β-olGenerator
b-DihydrofucosterolGenerator
Β-dihydrofucosterolGenerator
g-SitosterolGenerator
Γ-sitosterolGenerator
Poriferast-5-en-3b-olGenerator
Poriferast-5-en-3β-olGenerator
24b-Ethylcholest-5-en-3b-olHMDB
24-EthylcholesterolHMDB
3beta-Stigmast-5-en-3-olHMDB
SitosterolHMDB
Sitosterol, (3beta,24xi)-isomerHMDB
Sitosterol, 26-(14)C-labeledHMDB
3beta-SitosterolHMDB
HarzolHMDB
beta-SitosterolHMDB
Sitosterol, (3beta)-isomerHMDB
Chemical FormulaC29H50O
Average Molecular Mass414.707 g/mol
Monoisotopic Mass414.386 g/mol
CAS Registry Number83-47-6
IUPAC Name(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5S)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol
Traditional Name(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5S)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol
SMILESCCC(CCC(C)C1CCC2C3CC=C4CC(O)CCC4(C)C3CCC12C)C(C)C
InChI IdentifierInChI=1S/C29H50O/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/h10,19-21,23-27,30H,7-9,11-18H2,1-6H3
InChI KeyKZJWDPNRJALLNS-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
  • C24-propyl-sterol-skeleton
  • Stigmastane-skeleton
  • Triterpenoid
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • Hydroxysteroid
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • 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 Solubility1.8e-05 g/LALOGPS
logP7.27ALOGPS
logP7.84ChemAxon
logS-7.4ALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity129.77 m³·mol⁻¹ChemAxon
Polarizability54.39 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052v-1109000000-ae76f369c8c1b1b4fe0aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-4103900000-a09c1c265657e57bd096Spectrum
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 GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0019500000-b9eddfa8d56747167adaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-5139100000-42d184a108f9e994dc01Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9076000000-54ef98673160128cbacdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0002900000-158617c2e43f1a46b58aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0004900000-632250471791929b07e3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-2019000000-717c6229722cf73f3faaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-1118900000-620dc34d093f424c1d89Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014l-9163100000-4a80c636d0cb9659262fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-9521000000-76b9e6176a167e0b61b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000900000-eda302082c5114b2ab3aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0001900000-c37ac1577c1ddfa75134Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06r2-4016900000-e870c8bbee027c7c3a5aSpectrum
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 IDHMDB0000649
FooDB IDFDB112200
Phenol Explorer IDNot Available
KNApSAcK IDC00023769
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID5621
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID402901
ChEBI ID132823
PubChem Compound ID457801
Kegg Compound IDC19654
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=22863942
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24417147
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=24831420
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=26710827
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=27694009
6. Kind, C. Albert; Bergmann, Werner. Marine products. X. Clionasterol. Journal of Organic Chemistry (1942), 7 341-5.
7. Cerqueira F, Watanadilok R, Sonchaeng P, Kijjoa A, Pinto M, Quarles van Ufford H, Kroes B, Beukelman C, Nascimento MS: Clionasterol: a potent inhibitor of complement component C1. Planta Med. 2003 Feb;69(2):174-6.