(2S,3R,4R,5R,6S)-2-{[(2R,3S,4S,5R,6R)-4-hydroxy-2-(hydroxymethyl)-6-[(1'S,2R,2'S,4'S,5R,7'S,8'R,9'S,12'S,13'R,16'S)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosan]-18'-eneoxy]-5-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol

• ChemBase ID: 73003
• Molecular Formular: C45H72O16
• Molecular Mass: 869.04358
• Monoisotopic Mass: 868.48203622
• SMILES: [C@H]1([C@H]([C@@H](O[C@H]([C@@H]1O)O[C@H]1[C@H](O)[C@H]([C@@H](O[C@@H]1CO)O[C@@H]1CC2=CC[C@@H]3[C@@H]([C@]2(CC1)C)CC[C@]1([C@H]3C[C@H]2[C@@H]1[C@@H]([C@@]1(O2)OC[C@@H](CC1)C)C)C)O[C@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)C)O)O)O)C)O)O
• Canonical SMILES: OC[C@H]1O[C@@H](O[C@H]2CC[C@]3(C(=CC[C@@H]4[C@@H]3CC[C@]3([C@H]4C[C@H]4[C@@H]3[C@H](C)[C@]3(O4)CC[C@H](CO3)C)C)C2)C)[C@@H]([C@H]([C@@H]1O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O
• InChI: InChI=1S/C45H72O16/c1-19-9-14-45(54-18-19)20(2)30-28(61-45)16-27-25-8-7-23-15-24(10-12-43(23,5)26(25)11-13-44(27,30)6)57-42-39(60-41-36(52)34(50)32(48)22(4)56-41)37(53)38(29(17-46)58-42)59-40-35(51)33(49)31(47)21(3)55-40/h7,19-22,24-42,46-53H,8-18H2,1-6H3/t19-,20+,21+,22+,24+,25-,26+,27+,28+,29-,30+,31+,32+,33-,34-,35-,36-,37+,38-,39-,40+,41+,42-,43+,44+,45-/m1/s1
• InChIKey: VNONINPVFQTJOC-ZGXDEBHDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4R,5R,6S)-2-{[(2R,3S,4S,5R,6R)-4-hydroxy-2-(hydroxymethyl)-6-[(1'S,2R,2'S,4'S,5R,7'S,8'R,9'S,12'S,13'R,16'S)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosan]-18'-eneoxy]-5-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol
• IUPAC Traditional name: dioscin
• Synonyms: Collettiside III; CCRIS 4123; Dioscin(Collettiside III)

Database IDs

• CAS Number: 19057-60-4
• PubChem SID: 162037923
• PubChem CID: 119245

CALCULATED PROPERTIES

• Acid pKa: 11.883741
• H Acceptors: 16
• H Donor: 8
• LogD (pH = 5.5): 1.7086183
• LogD (pH = 7.4): 1.7086042
• Log P: 1.7086184
• Molar Refractivity: 214.4184 cm^3
• Polarizability: 87.55093 Å^3
• Polar Surface Area: 235.68 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: -20°C

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S2379

Research Area: Cancer
Biological Activity:
Dioscin(Collettiside III) is extracted and isolated from Polygonatum Zanlanscianense Pamp with  IC50 of 2.6, 0.8, 7.5, and 4.5 μM for the inhibition of the growth of the MDA-MB-435, H14, HL60, and HeLa cell lines, respectively. Hela cells underwent apoptosis in dose- and time-dependent manners when treated with Dioscin. Caspase-3, -8 and -9 activities were also detected. The low enzymatic activity of caspase-8 and high activity of caspase-9 showed that the mitochondrial pathway was activated in apoptosis. [1] [2]

REFERENCES

• Cai J et al. Biol Pharm Bull. 2002 Feb;25(2):193-6.