(2S,3R,4S,5S,6R)-2-{3-hydroxy-5-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]phenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

• ChemBase ID: 131685
• Molecular Formular: C21H24O9
• Molecular Mass: 420.40986
• Monoisotopic Mass: 420.14203235
• SMILES: COc1ccc(cc1O)/C=C/c1cc(cc(c1)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)O
• Canonical SMILES: OC[C@H]1O[C@@H](Oc2cc(/C=C/c3ccc(c(c3)O)OC)cc(c2)O)[C@@H]([C@H]([C@@H]1O)O)O
• 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+/t17-,18-,19+,20-,21-/m1/s1
• InChIKey: GKAJCVFOJGXVIA-DXKBKAGUSA-N

NAMES AND DATABASE IDS

Names

• 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
• IUPAC Traditional name: rhaponticin
• Synonyms: 3,3′,5-Trihydroxy-4′-methoxystilbene 3-O-β-D-glucoside; NSC 43321; Rhaponticin; Rhapontin

Database IDs

• CAS Number: 155-58-8
• EC Number: 205-845-0
• MDL Number: MFCD00010117
• PubChem SID: 24899400; 162225962
• PubChem CID: 637213

CALCULATED PROPERTIES

• Acid pKa: 9.210916
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): 0.97656757
• LogD (pH = 7.4): 0.97001487
• Log P: 0.97665155
• Molar Refractivity: 106.0631 cm^3
• Polarizability: 41.509747 Å^3
• Polar Surface Area: 149.07 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99% (HPLC)
• Biological Source: from rhubarb