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beta-Sitosterol 3-O-beta-D-Glucuronopyranoside (FDB021626)

Record Information
Version1.0
Creation date2011-03-17 23:25:00 UTC
Update date2019-11-26 03:20:36 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
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot 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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC35H58O7
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
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
Isomeric SMILESCCC(CCC(C)C1CCC2C3CC=C4CC(CCC4(C)C3CCC12C)OC1OC(C(O)C(O)C1O)C(O)=O)C(C)C
Average Molecular Weight590.8308
Monoisotopic Molecular Weight590.41825421
Classification
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
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
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
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01bd-0105590000-0202658cf68b33b6b2ce2018-04-05View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-3219610000-a456c3e3c020b51f8b922018-04-05View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kb-5329100000-8993f8f563688e699cba2018-04-05View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01pa-1101490000-c455b52705d690bad9312018-04-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-2202930000-a1c7fc688278da5c10582018-04-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-7107900000-77a78be39fd2ae964ecd2018-04-06View Spectrum
NMRNot Available
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
Dr. Duke IDBETA-SITOSTEROL-GLUCOSIDE|BETA-SITOSTEROL-D-GLUCOSIDE|BETA-SITOSTEROL-BETA-D-GLUCOPYRANOSIDE
BIGG IDNot Available
KNApSAcK IDNot Available
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 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
convulsantDUKE
hypoglycemic35526 A drug which lowers the blood glucose level.DUKE
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).