1.0 2010-04-08 22:08:07 UTC 2019-11-26 03:02:42 UTC FDB008525 Rhapontin Rhapontin 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 . 3,3',5-Trihydroxy-4'-methoxystilbene 3-O-beta-D-glucoside 4'-Methoxy-3,3',5-trihydroxystilbene 3-O-beta-D-glucopyranoside Glucopyranoside, rhapontigenin-3, β-D- Glucopyranoside, rhapontigenin-3, beta-D- Ponticin Rhaponthin Rhaponticin Rhaponticine Rhapontigenin 3-O-beta-D-glucopyranoside Rhapontigenin, 3-β-D-glucopyranoside Rhapontigenin, 3-beta-D-glucopyranoside Rhapontin Rhapontin (8CI) C21H24O9 420.4099 420.142032366 2-{3-hydroxy-5-[(Z)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]phenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol 2-{3-hydroxy-5-[(Z)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]phenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol 155-58-8 COC1=CC=C(\C=C/C2=CC(OC3OC(CO)C(O)C(O)C3O)=CC(O)=C2)C=C1O InChI=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- GKAJCVFOJGXVIA-IHWYPQMZSA-N 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. Stilbene glycosides Organic compounds Phenylpropanoids and polyketides Stilbenes Stilbene glycosides Aromatic heteromonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Acetals Alkyl aryl ethers Anisoles Hexoses Hydrocarbon derivatives Methoxybenzenes Methoxyphenols O-glycosyl compounds Oxacyclic compounds Oxanes Phenolic glycosides Phenoxy compounds Polyols Primary alcohols Secondary alcohols Styrenes 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Acetal Alcohol Alkyl aryl ether Anisole Aromatic heteromonocyclic compound Benzenoid Ether Glycosyl compound Hexose monosaccharide Hydrocarbon derivative Methoxybenzene Methoxyphenol Monocyclic benzene moiety Monosaccharide O-glycosyl compound Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxane Phenol Phenol ether Phenolic glycoside Phenoxy compound Polyol Primary alcohol Secondary alcohol Stilbene glycoside Styrene logp 0.70 ALOGPS logs -2.86 ALOGPS solubility 5.85e-01 g/l ALOGPS melting_point Mp 236-237° dec. logp 0.98 ChemAxon pka_strongest_acidic 9.21 ChemAxon pka_strongest_basic -3 ChemAxon iupac 2-{3-hydroxy-5-[(Z)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]phenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol ChemAxon average_mass 420.4099 ChemAxon mono_mass 420.142032366 ChemAxon smiles COC1=CC=C(\C=C/C2=CC(OC3OC(CO)C(O)C(O)C3O)=CC(O)=C2)C=C1O ChemAxon formula C21H24O9 ChemAxon inchi InChI=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- ChemAxon inchikey GKAJCVFOJGXVIA-IHWYPQMZSA-N ChemAxon polar_surface_area 149.07 ChemAxon refractivity 106.06 ChemAxon polarizability 42.33 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 9 ChemAxon donor_count 6 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 90633 Specdb::MsMs 90634 Specdb::MsMs 90635 Specdb::MsMs 153822 Specdb::MsMs 153823 Specdb::MsMs 153824 Garden rhubarb Type 1 specific Rheum rhabarbarum 3621 1420.0 1420.0 1420.0 mg/100 g Estrogenic 922