Stereochemistry | ABSOLUTE |
Molecular Formula | C29H42O10 |
Molecular Weight | 550.6378 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 13 / 13 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]6(O[C@H]1CC[C@]2(C=O)[C@@]3([H])CC[C@]4(C)[C@H](CC[C@]4(O)[C@]3([H])CC[C@]2(O)C1)C5=CC(=O)OC5)O[C@@H](C)[C@H](O)[C@@H](O)[C@H]6O
InChI
InChIKey=HULMNSIAKWANQO-JQKSAQOKSA-N
InChI=1S/C29H42O10/c1-15-22(32)23(33)24(34)25(38-15)39-17-3-8-27(14-30)19-4-7-26(2)18(16-11-21(31)37-13-16)6-10-29(26,36)20(19)5-9-28(27,35)12-17/h11,14-15,17-20,22-25,32-36H,3-10,12-13H2,1-2H3/t15-,17-,18+,19-,20+,22-,23+,24+,25-,26+,27-,28-,29-/m0/s1
Molecular Formula | C29H42O10 |
Molecular Weight | 550.6378 |
Charge | 0 |
Count |
MOL RATIO
1 MOL RATIO (average) |
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 13 / 13 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Convallatoxin is a glycoside extracted from Convallaria majalis. Convallatoxin is also isolated from the trunk bark of Antiaris toxicaria. It is a cardenolide glycoside that consists of strophanthidin having a 6-deoxy-α-L-mannopyranosyl (L-rhamnosyl) group attached at position 3. Convallatoxin is widely used as a cardiac glycoside in acute and chronic congestive heart-failure and paroxysmal tachycardia, with many effects and underlying protective mechanisms on inflammation and cellular proliferation. It can inhibit the Na+,K+-ATPase in congestive heart failure or arrythmias. Convallatoxin has been shown to be a dual inducer of autophagy and apoptosis, it inhibits angiogenesis in vitro and in vivo. Convallatoxin, exhibits antiproliferative properties against a number of cancer types. Convallatoxin presents antiproliferative effects against colorectal cancer cells in culture and that the resulting cell death is independent of the p53 tumor suppressor. Thus convallatoxin may be useful in the treatment of cancers that harbor inactivating mutations in the p53 signaling pathway.
Approval Year
PubMed
Patents
Sample Use Guides
Anti-breast cancer effect of Convallatoxin against HER2 overexpressing BT-474, and estrogen and HER2 negative MDA-MB-231 breast cancer cell lines was evaluated. Convallatoxin showed the most potent activity with IC50 values of 0.63 ± 0.56, and 0.69 ± 0.08 uM against BT-474 and MDA-MB-231 cells.