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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
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

PubMed

TitleDatePubMed
The positive inotropic effect of the aqueous extract of Convallaria keiskei in beating rabbit atria.
2006 Aug 15
[Effects of digoxin and corglycon on ion currents in neuronal membrane of snail (Lymnaea stagnalis)].
2008 Sep-Oct
Cytotoxic effects of cardiac glycosides in colon cancer cells, alone and in combination with standard chemotherapeutic drugs.
2009 Nov
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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 01:37:39 UTC 2023
Edited
by admin
on Sat Dec 16 01:37:39 UTC 2023
Record UNII
JY264VIR1Y
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CONVALLATOXIN
MI   WHO-DD  
Common Name English
KORGLYKON
Common Name English
CONVALLATON
Common Name English
Convallatoxin [WHO-DD]
Common Name English
CARD-20(22)-ENOLIDE, 3-((6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)OXY)-5,14-DIHYDROXY-19-OXO-, (3.BETA.,5.BETA.)-
Common Name English
CONVALLATOXIN [MI]
Common Name English
CORGLYKON
Common Name English
NSC-407808
Code English
STROPHANTHIDIN .ALPHA.-L-RHAMNOSIDE
Common Name English
Code System Code Type Description
WIKIPEDIA
CONVALLATOXIN
Created by admin on Sat Dec 16 01:37:39 UTC 2023 , Edited by admin on Sat Dec 16 01:37:39 UTC 2023
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HSDB
3475
Created by admin on Sat Dec 16 01:37:39 UTC 2023 , Edited by admin on Sat Dec 16 01:37:39 UTC 2023
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SMS_ID
100000141225
Created by admin on Sat Dec 16 01:37:39 UTC 2023 , Edited by admin on Sat Dec 16 01:37:39 UTC 2023
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CHEBI
27663
Created by admin on Sat Dec 16 01:37:39 UTC 2023 , Edited by admin on Sat Dec 16 01:37:39 UTC 2023
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NSC
407808
Created by admin on Sat Dec 16 01:37:39 UTC 2023 , Edited by admin on Sat Dec 16 01:37:39 UTC 2023
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MERCK INDEX
m3767
Created by admin on Sat Dec 16 01:37:39 UTC 2023 , Edited by admin on Sat Dec 16 01:37:39 UTC 2023
PRIMARY Merck Index
PUBCHEM
441852
Created by admin on Sat Dec 16 01:37:39 UTC 2023 , Edited by admin on Sat Dec 16 01:37:39 UTC 2023
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MESH
C000505
Created by admin on Sat Dec 16 01:37:39 UTC 2023 , Edited by admin on Sat Dec 16 01:37:39 UTC 2023
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CAS
508-75-8
Created by admin on Sat Dec 16 01:37:39 UTC 2023 , Edited by admin on Sat Dec 16 01:37:39 UTC 2023
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EVMPD
SUB91169
Created by admin on Sat Dec 16 01:37:39 UTC 2023 , Edited by admin on Sat Dec 16 01:37:39 UTC 2023
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EPA CompTox
DTXSID90862073
Created by admin on Sat Dec 16 01:37:39 UTC 2023 , Edited by admin on Sat Dec 16 01:37:39 UTC 2023
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FDA UNII
JY264VIR1Y
Created by admin on Sat Dec 16 01:37:39 UTC 2023 , Edited by admin on Sat Dec 16 01:37:39 UTC 2023
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ECHA (EC/EINECS)
208-086-3
Created by admin on Sat Dec 16 01:37:39 UTC 2023 , Edited by admin on Sat Dec 16 01:37:39 UTC 2023
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