beta-Sitosterol 3-O-beta-D-Glucuronopyranoside (CHEM034674)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:06:53 UTC
Update Date2016-11-09 01:21:10 UTC
Accession NumberCHEM034674
Identification
Common Namebeta-Sitosterol 3-O-beta-D-Glucuronopyranoside
ClassSmall Molecule
DescriptionBeta-sitosterol 3-o-beta-d-glucuronopyranoside is a member of the class of compounds known as steroid glucuronide conjugates. Steroid glucuronide conjugates are sterol lipids containing a glucuronide moiety linked to the steroid skeleton. Beta-sitosterol 3-o-beta-d-glucuronopyranoside is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Beta-sitosterol 3-o-beta-d-glucuronopyranoside can be found in a number of food items such as dill, bitter gourd, dandelion, and german camomile, which makes beta-sitosterol 3-o-beta-d-glucuronopyranoside a potential biomarker for the consumption of these food products.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
b-Sitosterol 3-O-b-D-glucuronopyranosideGenerator
Β-sitosterol 3-O-β-D-glucuronopyranosideGenerator
Chemical FormulaC35H58O7
Average Molecular Mass590.831 g/mol
Monoisotopic Mass590.418 g/mol
CAS Registry Number126251-01-2
IUPAC Name6-{[14-(5-ethyl-6-methylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name6-{[14-(5-ethyl-6-methylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
SMILESCCC(CCC(C)C1CCC2C3CC=C4CC(CCC4(C)C3CCC12C)OC1OC(C(O)C(O)C1O)C(O)=O)C(C)C
InChI IdentifierInChI=1S/C35H58O7/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(14-16-34(22,5)27(24)15-17-35(25,26)6)41-33-30(38)28(36)29(37)31(42-33)32(39)40/h10,19-21,23-31,33,36-38H,7-9,11-18H2,1-6H3,(H,39,40)
InChI KeyREARGUUVUPUXPW-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as steroid glucuronide conjugates. These are sterol lipids containing a glucuronide moiety linked to the steroid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroidal glycosides
Direct ParentSteroid glucuronide conjugates
Alternative Parents
Substituents
  • C24-propyl-sterol-skeleton
  • Steroid-glucuronide-skeleton
  • Stigmastane-skeleton
  • Triterpenoid
  • Delta-5-steroid
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Beta-hydroxy acid
  • Pyran
  • Oxane
  • Hydroxy acid
  • Monosaccharide
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Polyol
  • Acetal
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
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 Solubility0.003 g/LALOGPS
logP6.05ALOGPS
logP6.39ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)3.43ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area116.45 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity162.05 m³·mol⁻¹ChemAxon
Polarizability69.95 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, Positivesplash10-01bd-0105590000-0202658cf68b33b6b2ceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-3219610000-a456c3e3c020b51f8b92Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kb-5329100000-8993f8f563688e699cbaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01pa-1101490000-c455b52705d690bad931Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-2202930000-a1c7fc688278da5c1058Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-7107900000-77a78be39fd2ae964ecdSpectrum
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 IDHMDB0168484
FooDB IDFDB021626
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 ID4447509
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available