Record Information
Creation date2011-03-17 23:25:00 UTC
Update date2018-01-25 19:44:12 UTC
Primary IDFDB021626
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namebeta-Sitosterol 3-O-beta-D-Glucuronopyranoside
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.
CAS Number126251-01-2
Stigmast-5-en-3-ol; (3b,24R)-form, O-b-D-Glucuronopyranosidedb_source
Predicted Properties
Water Solubility0.003 g/LALOGPS
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
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC35H58O7
IUPAC name6-{[14-(5-ethyl-6-methylheptan-2-yl)-2,15-dimethyltetracyclo[^{2,7}.0^{11,15}]heptadec-7-en-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
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)
Average Molecular Weight590.8308
Monoisotopic Molecular Weight590.41825421
DescriptionThis compound 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
  • Polycyclic triterpenoid
  • Triterpenoid
  • Stigmastane-skeleton
  • Steroid-glucuronide-skeleton
  • C24-propyl-sterol-skeleton
  • Delta-5-steroid
  • O-glucuronide
  • 1-o-glucuronide
  • Glucuronic acid or derivatives
  • O-glycosyl compound
  • Glycosyl compound
  • Pyran carboxylic acid
  • Pyran carboxylic acid or derivatives
  • Beta-hydroxy acid
  • Pyran
  • Oxane
  • Monosaccharide
  • Hydroxy acid
  • Saccharide
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Acetal
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 71.15%; H 9.89%; O 18.96%DFC
Melting PointMp 280-290?DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D -30.2 (Py)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectrum TypeDescriptionSplash Key
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDCBR05-M:HGN94-E
EAFUS IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET 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
Biological Effects and Interactions
Health Effects / Bioactivities
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
central nervous system depressant35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
central nervous system stimulant35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
hypoglycemic35526 A drug which lowers the blood glucose level.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
MSDSNot Available
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).