(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[2-(4-hydroxyphenyl)ethoxy]oxane-3,4,5-triol

• ChemBase ID: 73016
• Molecular Formular: C14H20O7
• Molecular Mass: 300.3044
• Monoisotopic Mass: 300.12090298
• SMILES: [C@H]1([C@H]([C@@H]([C@H]([C@@H](O1)OCCc1ccc(cc1)O)O)O)O)CO
• Canonical SMILES: OC[C@H]1O[C@@H](OCCc2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C14H20O7/c15-7-10-11(17)12(18)13(19)14(21-10)20-6-5-8-1-3-9(16)4-2-8/h1-4,10-19H,5-7H2/t10-,11-,12+,13-,14-/m1/s1
• InChIKey: ILRCGYURZSFMEG-RKQHYHRCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[2-(4-hydroxyphenyl)ethoxy]oxane-3,4,5-triol
• IUPAC Traditional name: salidroside
• Synonyms: Rhodioloside; Salidroside(Rhodioloside)

Database IDs

• CAS Number: 10338-51-9
• PubChem SID: 162037936
• PubChem CID: 159278

CALCULATED PROPERTIES

• Acid pKa: 10.198019
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -0.57985234
• LogD (pH = 7.4): -0.5805308
• Log P: -0.5798437
• Molar Refractivity: 72.0231 cm^3
• Polarizability: 28.860756 Å^3
• Polar Surface Area: 119.61 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: -20°C

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S2396

Research Area: Cancer
Biological Activity:
Salidroside (Rhodioloside; Rhodosin) is a glucoside compound with an IC50 of 4.99 ± 0.23 μg/mL for the proliferation of SACC-2. Salidroside (Rhodioloside; Rhodosin) could inhibit the proliferation of SACC-2 cells and induce SACC-2 cell apoptosis in vitro, which could be a kind of antitumor medicine in the future. Growing curve showed that SACC-2 cells of salidroside groups decreased with extending cell culture time. Immunohistochemistry staining showed that Caspase 3 and Caspase 8 were both strong positive expression in SACC-2 cells of salidroside groups, and poor positive expression in SACC-2 cells of control group, the difference was significant (P<0.01).Salidroside (Rhodioloside; Rhodosin) induces cell-cycle arrest and apoptosis in human breast cancer cells and may be a promising candidate for breast cancer treatment. [1][2][3]

REFERENCES

• Hu X et al. Biochem Biophys Res Commun. 2010 Jul 16;398(1):62-7.