Record Information
Version1.0
Creation date2010-04-08 22:04:55 UTC
Update date2019-11-26 02:56:18 UTC
Primary IDFDB001316
Secondary Accession Numbers
  • FDB001317
Chemical Information
FooDB NameIkshusterol
DescriptionIkshusterol, also known as hydroxysitosterol, 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, ikshusterol is considered to be a sterol lipid molecule. Ikshusterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
CAS Number34427-61-7
Structure
Thumb
Synonyms
SynonymSource
(-)-Stigmast-5-ene-3beta,7alpha-diolHMDB
(3beta,7alpha)-Stigmast-5-ene-3,7-diolHMDB
7a-HydroxysitosterolHMDB
HydroxysitosterolHMDB
Stigmast-5-ene-3beta,7alpha-diolHMDB
7-HydroxysitosterolMeSH
Ikshusteroldb_source
Stigmast-5-ene-3,7-diol, (3beta,7alpha)-biospider
Predicted PropertiesNot Available
Chemical FormulaC29H50O2
IUPAC name
InChI IdentifierInChI=1S/C29H50O2/c1-7-20(18(2)3)9-8-19(4)23-10-11-24-27-25(13-15-29(23,24)6)28(5)14-12-22(30)16-21(28)17-26(27)31/h17-20,22-27,30-31H,7-16H2,1-6H3
InChI KeySXJVFYZNUGGHRG-UHFFFAOYSA-N
Isomeric SMILESCCC(CCC(C)C1CCC2C3C(O)C=C4CC(O)CCC4(C)C3CCC12C)C(C)C
Average Molecular Weight430.7061
Monoisotopic Molecular Weight430.381080844
Classification
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
  • 7-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • 3-hydroxy-delta-5-steroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 80.87%; H 11.70%; O 7.43%DFC
Melting PointMp 129-133° (202-204°)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -27 (CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSIkshusterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0uxr-2225900000-0510eae09f2b875cac1dSpectrum
Predicted GC-MSIkshusterol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-6110390000-8479cd72fdba02cd060dSpectrum
Predicted GC-MSIkshusterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSIkshusterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSIkshusterol, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSIkshusterol, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSIkshusterol, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSIkshusterol, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSIkshusterol, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03e9-0004900000-89081fd83f08f3182b612015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dj-5239500000-c1f96ded361455520a2b2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00l2-9225000000-7111aef58b1509bc3fad2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03e9-0004900000-89081fd83f08f3182b612015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dj-5239500000-c1f96ded361455520a2b2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00l2-9225000000-7111aef58b1509bc3fad2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-aaae8dcf6c9d8a7432e72015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-0001900000-dce71605f3e85fe8384d2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ot-4019600000-6a3576bec055c92c5c972015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-aaae8dcf6c9d8a7432e72015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-0001900000-dce71605f3e85fe8384d2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ot-4019600000-6a3576bec055c92c5c972015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-d3ddef81c134412455e12021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0000900000-4595a9c13c1a7d4c015c2021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03fr-0002900000-429f896c1559551d6bbb2021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-3102900000-bff2cab376ddcf3448212021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004l-9116300000-e58251d574117cbc8cfc2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9320000000-77db897b274ed99d63f12021-09-25View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID161816
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDHKD05-I:BZL15-M
EAFUS IDNot Available
Dr. Duke IDSTIGMAST-5-ENE-3-BETA-7-ALPHA-DIOL
BIGG IDNot Available
KNApSAcK IDC00029585
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti fertilityDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.