Record Information
Version1.0
Creation date2010-04-08 22:08:07 UTC
Update date2019-11-26 03:02:42 UTC
Primary IDFDB008525
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameRhapontin
DescriptionRhapontin is a member of the class of compounds known as stilbene glycosides. Stilbene glycosides are compounds structurally characterized by the presence of a carbohydrate moiety glycosidically linked to the stilbene skeleton. Rhapontin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Rhapontin can be found in garden rhubarb, which makes rhapontin a potential biomarker for the consumption of this food product. Rhapontin has beneficial effects on diabetic mice, and in vitro results suggest it may be relevant to Alzheimer's disease with an action on beta amyloid .
CAS Number155-58-8
Structure
Thumb
Synonyms
SynonymSource
3,3',5-Trihydroxy-4'-methoxystilbene 3-O-beta-D-glucosidebiospider
4'-Methoxy-3,3',5-trihydroxystilbene 3-O-beta-D-glucopyranosidebiospider
Glucopyranoside, rhapontigenin-3, β-D-biospider
Glucopyranoside, rhapontigenin-3, beta-D-biospider
Ponticindb_source
Rhaponthinbiospider
Rhaponticindb_source
Rhaponticinebiospider
Rhapontigenin 3-O-beta-D-glucopyranosidebiospider
Rhapontigenin, 3-β-D-glucopyranosidebiospider
Rhapontigenin, 3-beta-D-glucopyranosidebiospider
Rhapontindb_source
Rhapontin (8CI)biospider
Predicted Properties
PropertyValueSource
Water Solubility0.58 g/LALOGPS
logP0.7ALOGPS
logP0.98ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)9.21ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area149.07 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity106.06 m³·mol⁻¹ChemAxon
Polarizability42.33 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC21H24O9
IUPAC name2-{3-hydroxy-5-[(Z)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]phenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol
InChI IdentifierInChI=1S/C21H24O9/c1-28-16-5-4-11(8-15(16)24)2-3-12-6-13(23)9-14(7-12)29-21-20(27)19(26)18(25)17(10-22)30-21/h2-9,17-27H,10H2,1H3/b3-2-
InChI KeyGKAJCVFOJGXVIA-IHWYPQMZSA-N
Isomeric SMILESCOC1=CC=C(\C=C/C2=CC(OC3OC(CO)C(O)C(O)C3O)=CC(O)=C2)C=C1O
Average Molecular Weight420.4099
Monoisotopic Molecular Weight420.142032366
Classification
Description Belongs to the class of organic compounds known as stilbene glycosides. Stilbene glycosides are compounds structurally characterized by the presence of a carbohydrate moiety glycosidically linked to the stilbene skeleton.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassStilbenes
Sub ClassStilbene glycosides
Direct ParentStilbene glycosides
Alternative Parents
Substituents
  • Stilbene glycoside
  • Phenolic glycoside
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Styrene
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Oxane
  • Monosaccharide
  • Monocyclic benzene moiety
  • Benzenoid
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Acetal
  • Ether
  • Polyol
  • Alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Primary alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 60.00%; H 5.75%; O 34.25%DFC
Melting PointMp 236-237° dec.DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]32D -59.5 (Me2CO)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, Positivesplash10-0ab9-0190500000-7abfc60e53bb5a1a83632016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-0290000000-5eec971a2ea361f59d992016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-2790000000-c523cfceff062b9f48002016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-066r-1261900000-2847d58d7c04bc5037582016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-1191100000-7f84c3037e5ebb69aabf2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-2090000000-130c4f0d5e71fa91d9ca2016-08-03View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC10288
Pubchem Compound ID637213
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDHFR82-M:DMZ66-D
EAFUS IDNot Available
Dr. Duke IDRHAPONTICIN
BIGG IDNot Available
KNApSAcK IDC00002904
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
estrogenicDUKE
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).