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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:34:14 UTC
Update Date2022-03-07 02:52:24 UTC
HMDB IDHMDB0030022
Secondary Accession Numbers
  • HMDB30022
Metabolite Identification
Common 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.
Structure
Data?1563861925
Synonyms
ValueSource
(-)-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
Chemical FormulaC29H50O2
Average Molecular Weight430.7061
Monoisotopic Molecular Weight430.381080844
IUPAC Name14-(5-ethyl-6-methylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,9-diol
Traditional Name14-(5-ethyl-6-methylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,9-diol
CAS Registry Number34427-61-7
SMILES
CCC(CCC(C)C1CCC2C3C(O)C=C4CC(O)CCC4(C)C3CCC12C)C(C)C
InChI Identifier
InChI=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
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
  • 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
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point129 - 133 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00017 g/LALOGPS
logP5.96ALOGPS
logP6.69ChemAxon
logS-6.4ALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-0.83ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity131.2 m³·mol⁻¹ChemAxon
Polarizability54.52 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+202.9931661259
DarkChem[M-H]-197.62831661259
DeepCCS[M-2H]-244.16530932474
DeepCCS[M+Na]+219.39330932474
AllCCS[M+H]+212.132859911
AllCCS[M+H-H2O]+210.332859911
AllCCS[M+NH4]+213.932859911
AllCCS[M+Na]+214.332859911
AllCCS[M-H]-206.032859911
AllCCS[M+Na-2H]-208.432859911
AllCCS[M+HCOO]-211.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
IkshusterolCCC(CCC(C)C1CCC2C3C(O)C=C4CC(O)CCC4(C)C3CCC12C)C(C)C2715.8Standard polar33892256
IkshusterolCCC(CCC(C)C1CCC2C3C(O)C=C4CC(O)CCC4(C)C3CCC12C)C(C)C2998.8Standard non polar33892256
IkshusterolCCC(CCC(C)C1CCC2C3C(O)C=C4CC(O)CCC4(C)C3CCC12C)C(C)C3394.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Ikshusterol,1TMS,isomer #1CCC(CCC(C)C1CCC2C3C(O[Si](C)(C)C)C=C4CC(O)CCC4(C)C3CCC12C)C(C)C3543.1Semi standard non polar33892256
Ikshusterol,1TMS,isomer #2CCC(CCC(C)C1CCC2C3C(O)C=C4CC(O[Si](C)(C)C)CCC4(C)C3CCC12C)C(C)C3523.5Semi standard non polar33892256
Ikshusterol,2TMS,isomer #1CCC(CCC(C)C1CCC2C3C(O[Si](C)(C)C)C=C4CC(O[Si](C)(C)C)CCC4(C)C3CCC12C)C(C)C3525.8Semi standard non polar33892256
Ikshusterol,1TBDMS,isomer #1CCC(CCC(C)C1CCC2C3C(O[Si](C)(C)C(C)(C)C)C=C4CC(O)CCC4(C)C3CCC12C)C(C)C3770.8Semi standard non polar33892256
Ikshusterol,1TBDMS,isomer #2CCC(CCC(C)C1CCC2C3C(O)C=C4CC(O[Si](C)(C)C(C)(C)C)CCC4(C)C3CCC12C)C(C)C3740.6Semi standard non polar33892256
Ikshusterol,2TBDMS,isomer #1CCC(CCC(C)C1CCC2C3C(O[Si](C)(C)C(C)(C)C)C=C4CC(O[Si](C)(C)C(C)(C)C)CCC4(C)C3CCC12C)C(C)C3955.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Ikshusterol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uxr-2225900000-0510eae09f2b875cac1d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ikshusterol GC-MS (2 TMS) - 70eV, Positivesplash10-0a4i-6110390000-8479cd72fdba02cd060d2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ikshusterol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ikshusterol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ikshusterol GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ikshusterol GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ikshusterol GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ikshusterol GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ikshusterol GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ikshusterol 10V, Positive-QTOFsplash10-03e9-0004900000-89081fd83f08f3182b612015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ikshusterol 20V, Positive-QTOFsplash10-03dj-5239500000-c1f96ded361455520a2b2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ikshusterol 40V, Positive-QTOFsplash10-00l2-9225000000-7111aef58b1509bc3fad2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ikshusterol 10V, Positive-QTOFsplash10-03e9-0004900000-89081fd83f08f3182b612015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ikshusterol 20V, Positive-QTOFsplash10-03dj-5239500000-c1f96ded361455520a2b2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ikshusterol 40V, Positive-QTOFsplash10-00l2-9225000000-7111aef58b1509bc3fad2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ikshusterol 10V, Negative-QTOFsplash10-004i-0000900000-aaae8dcf6c9d8a7432e72015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ikshusterol 20V, Negative-QTOFsplash10-01t9-0001900000-dce71605f3e85fe8384d2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ikshusterol 40V, Negative-QTOFsplash10-01ot-4019600000-6a3576bec055c92c5c972015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ikshusterol 10V, Negative-QTOFsplash10-004i-0000900000-aaae8dcf6c9d8a7432e72015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ikshusterol 20V, Negative-QTOFsplash10-01t9-0001900000-dce71605f3e85fe8384d2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ikshusterol 40V, Negative-QTOFsplash10-01ot-4019600000-6a3576bec055c92c5c972015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ikshusterol 10V, Negative-QTOFsplash10-004i-0000900000-d3ddef81c134412455e12021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ikshusterol 20V, Negative-QTOFsplash10-004i-0000900000-4595a9c13c1a7d4c015c2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ikshusterol 40V, Negative-QTOFsplash10-03fr-0002900000-429f896c1559551d6bbb2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ikshusterol 10V, Positive-QTOFsplash10-001i-3102900000-bff2cab376ddcf3448212021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ikshusterol 20V, Positive-QTOFsplash10-004l-9116300000-e58251d574117cbc8cfc2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ikshusterol 40V, Positive-QTOFsplash10-0a4i-9320000000-77db897b274ed99d63f12021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • 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 IDFDB001317
KNApSAcK IDC00032207
Chemspider ID4477002
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5318414
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.