Showing metabocard for Stigmastanol (BMDB0000494)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:31:34 UTC
Update Date2020-05-11 20:50:30 UTC
BMDB IDBMDB0000494
Secondary Accession Numbers
  • BMDB00494
Metabolite Identification
Common NameStigmastanol
DescriptionStigmastanol, also known as beta-sitostanol or dihydrositosterol, 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. Based on a literature review a significant number of articles have been published on Stigmastanol.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
DihydrositosterolMeSH
24 alpha-Ethyl-5 beta-cholestan-3 alpha-olMeSH
beta-SitostanolMeSH
SitostanolMeSH
Stigmastanol, (3beta,5beta,24S)-isomerMeSH
24 alpha-Ethyl-5 alpha-cholestan-3 beta-olMeSH
(3b)-Stigmastan-3-olHMDB
(3beta)-Stigmastan-3-olHMDB
(3beta,5alpha)-Stigmastan-3-olHMDB
24-alpha-EthylcholestanolHMDB
24a-EthylcholestanolHMDB
4a-Methyl-5a,14a-lumistan-3b-olHMDB
4a-MethylcampestanolHMDB
5,6-dihydro-b-SitosterolHMDB
5,6-dihydro-beta-SitosterolHMDB
5a-Stigmastan-3b-olHMDB
5alpha-Stigmastan-3beta-olHMDB
b-SitostanolHMDB
beta-dihydro-SitosterolHMDB
dihydro-b-SitosterolHMDB
dihydro-beta-SitosterolHMDB
DihydrositosterinHMDB
FucostanolHMDB
SpinastanolHMDB
Stigmastan-3-olHMDB
Stigmastane-3-beta-olHMDB
StigmastanolMeSH
Chemical FormulaC29H52O
Average Molecular Weight416.734
Monoisotopic Molecular Weight416.401816294
IUPAC Name(1S,2S,5S,10R,11S,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-ol
Traditional Namestigmastane-3-β-ol
CAS Registry Number83-45-4
SMILES
CC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C
InChI Identifier
InChI=1S/C29H52O/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/h19-27,30H,7-18H2,1-6H3/t20-,21-,22?,23+,24+,25-,26+,27+,28+,29-/m1/s1
InChI KeyLGJMUZUPVCAVPU-KZXGMYDKSA-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
  • C24-propyl-sterol-skeleton
  • 3-beta-hydroxysteroid
  • 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
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Golgi
  • Lysosome
  • Membrane
  • Mitochondria
  • Nucleus
  • Peroxisome
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point144 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP7.23ALOGPS
logP8.25ChemAxon
logS-7.6ALOGPS
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 Count6ChemAxon
Refractivity128.92 m³·mol⁻¹ChemAxon
Polarizability54.93 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-066u-4942100000-604c3357e69c5eff6d37View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-066u-4942100000-604c3357e69c5eff6d37View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f79-2109200000-a86730d94764ca5efe85View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-3103900000-2af97f9cf8a2adff3196View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0019600000-d66897ecdbe2fe845508View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-4149200000-b304e7e4678a4df85f02View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-8089100000-404a21c90ecdfcc88b6bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0002900000-5b14a67727dfd30debe9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0004900000-af8991b83701d4b9f081View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0012-1009000000-eebc7b9b36cf260dbcebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000900000-b5f23f2410b0642246b1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0000900000-bb6fb31d418e3fc0bd50View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02ta-0004900000-0b0cca9041a827eb2238View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-2125900000-88705afd06ff3d3ec277View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9022300000-71d6fc93ae624cc61e6cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9610000000-0304da0e562e0b20612fView in MoNA
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Golgi
  • Lysosome
  • Membrane
  • Mitochondria
  • Nucleus
  • Peroxisome
Biospecimen Locations
  • Skeletal Muscle
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Skeletal MuscleExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000494
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00025214
Chemspider IDNot Available
KEGG Compound IDC11682
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkStigmastanol
METLIN IDNot Available
PubChem Compound72340
PDB IDNot Available
ChEBI ID9479
References
Synthesis ReferenceBengtsson, B. E. A comparison between sitostanol and stigmastanol. Z. physiol. Chem. (1935), 237 46-51.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available