stigmasterol 3-O-β-D-glucoside (CHEM042410)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 02:02:08 UTC
Update Date2016-11-09 01:22:40 UTC
Accession NumberCHEM042410
Identification
Common Namestigmasterol 3-O-β-D-glucoside
ClassSmall Molecule
DescriptionStigmasterol 3-o-β-d-glucoside, also known as poriferasterol monoglucoside or substance f, belongs to stigmastanes and derivatives class of compounds. Those 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. Stigmasterol 3-o-β-d-glucoside is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Stigmasterol 3-o-β-d-glucoside can be found in a number of food items such as feijoa, star anise, quinoa, and mentha (mint), which makes stigmasterol 3-o-β-d-glucoside a potential biomarker for the consumption of these food products.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Stigmasterol-beta-D-glucosideMeSH
Substance FMeSH
Poriferasterol monoglucosideMeSH
Chemical FormulaC35H58O6
Average Molecular Mass574.843 g/mol
Monoisotopic Mass574.423 g/mol
CAS Registry NumberNot Available
IUPAC Name2-{[14-(5-ethyl-6-methylhept-3-en-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
Traditional Name2-{[14-(5-ethyl-6-methylhept-3-en-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
SMILESCCC(C=CC(C)C1CCC2C3CC=C4CC(CCC4(C)C3CCC12C)OC1OC(CO)C(O)C(O)C1O)C(C)C
InChI IdentifierInChI=1S/C35H58O6/c1-7-22(20(2)3)9-8-21(4)26-12-13-27-25-11-10-23-18-24(14-16-34(23,5)28(25)15-17-35(26,27)6)40-33-32(39)31(38)30(37)29(19-36)41-33/h8-10,20-22,24-33,36-39H,7,11-19H2,1-6H3
InChI KeyVWDLOXMZIGUBKM-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
  • Triterpenoid
  • Stigmastane-skeleton
  • Steroidal glycoside
  • Delta-5-steroid
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Oxane
  • Monosaccharide
  • Secondary alcohol
  • Polyol
  • Oxacycle
  • Acetal
  • Organoheterocyclic compound
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic 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 Solubility0.0038 g/LALOGPS
logP5.3ALOGPS
logP5.71ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)12.21ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area99.38 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity163.3 m³·mol⁻¹ChemAxon
Polarizability69.1 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03fs-3207890000-5e6721b482386e8c41bcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ot-6319510000-cf094fc542208088502eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-7539200000-bcffdbcb33f3e3acc188Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0229-1202590000-9252d740b2abb5e9d0fcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-1203920000-a00efbfe3df2dabe68e2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03dj-7009800000-75aec862a53456621835Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1100290000-0a0f5518b6d17b42408cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-9236340000-44778a1f2edf66b61452Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0r9s-9501610000-3a9f1f275910607acfbeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000090000-ca4e1f5b8a7c489805afSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-4100490000-7f47d4f532ce40c313b1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9002420000-81dea6ffd800933a9a73Spectrum
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 IDNot Available
FooDB IDFDB031185
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID73072970
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available