Structure via PubChem · Public domain (PubChem)
Rhaponticin
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Rhaponticin is a stilbenoid glucoside compound. Its aglycone is called rhapontigenin. It can be found in rhubarb rhizomes.
Chemical data
- Formula
- C21H24O9
- Molecular weight
- 420.4 g/mol
- IUPAC name
- (2S,3R,4S,5S,6R)-2-[3-hydroxy-5-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
- SMILES
- COC1=C(C=C(C=C1)/C=C/C2=CC(=CC(=C2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O
- InChIKey
- GKAJCVFOJGXVIA-DXKBKAGUSA-N
- XLogP
- 0.5
- Polar surface area
- 149 Ų
- H-bond donors
- 6
- H-bond acceptors
- 9
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Mass
- 420.142032
Show 4 more facts
- found in taxon
- Rheum webbianum
- canonical SMILES
- COC1=C(C=C(C=C1)C=CC2=CC(=CC(=C2)OC3C(C(C(C(O3)CO)O)O)O)O)O
- chemical formula
- C₂₁H₂₄O₉
- isomeric SMILES
- COC1=C(C=C(C=C1)/C=C/C2=CC(=CC(=C2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
{{Chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 429837892 | Name = Rhaponticin | ImageFile = Rhaponticin.svg | ImageName = Chemical structure of rhaponticin | ImageAlt = Chemical structure of rhaponticin | ImageSize = 250px | IUPACName = 3-Hydroxy-5-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethen-1-yl]phenyl β-D-glucopyranoside | SystematicName = (2S,3R,4S,5S,6R)-2-{3-Hydroxy-5-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethen-1-yl]phenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol | OtherNames = 3',5-Dihydroxy-4'-methoxystilbene 3-O-beta-D-glucopyranosidePonticinRhapontinRhapontigenin glucoside |Section1= |Section2= |Section3= }} Rhaponticin is a stilbenoid glucoside compound. Its aglycone is called rhapontigenin. It can be found in rhubarb rhizomes.
It 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. It is a phytoestrogen and has estrogenic activity.
Excerpted from Wikipedia’s “Rhaponticin” article, available under the CC BY-SA 4.0 licence.