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Details

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
Structure of CONVALLATOXIN

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

HIDE SMILES / InChI

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

Description

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

Sample Use Guides

In Vitro Use Guide
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.
Substance Class Chemical
Record UNII
JY264VIR1Y
Record Status Validated (UNII)
Record Version