Convallatoxin

Convallatoxin
Names
	IUPAC name (3S,5S,8R,9S,10S,13R,14S,17R)-5,14-dihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
	Other names Strophanthin 3alpha-1-rhamnoside ; Strophanthidin alpha-l-rhamnopyranoside; Strophanthidin a-l-rhamnopyranoside; Corglykon;20(22),5beta-cardenolid-19-al-3beta,5beta,14beta-triol-3beta-d-[a-1-rhamnopyranoside] ; 5Beta,20[22]-cardenolide-19-one-3beta,5alpha,14-triol-3-[6-deoxy-alpha-l-mannopyranosyl] ; 3Beta,5alpha,14-trihydroxy-19-oxo-5beta,20[22]-cardenolide-3-[6-deoxy-alpha-l-mannopyranosyl]
Identifiers
CAS Number	508-75-8 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:27663 ;
ChEMBL	ChEMBL399336 ;
ChemSpider	390428 ;
ECHA InfoCard	100.007.352
EC Number	208-086-3
PubChem CID	441852;
	InChI 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 Key: HULMNSIAKWANQO-JQKSAQOKSA-N ; InChI=1/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 Key: HULMNSIAKWANQO-JQKSAQOKBT;
	SMILES O=C\1OC/C(=C/1)[C@H]2CC[C@@]6(O)[C@]2(C)CC[C@H]4[C@H]6CC[C@]5(O)C[C@@H](O[C@@H]3O[C@H]([C@H](O)[C@@H](O)[C@H]3O)C)CC[C@]45C=O;
Properties
Chemical formula	C29H42O10
Molar mass	550.65 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

Convallatoxin is a glycoside extracted from Convallaria majalis.

Action and uses

Similar to digitalis, it is mainly used for acute and chronic heart failure.

Detection

Convallatoxin can be detected alongside digoxin using luminescent oxygen channelling technology–based digoxin assay LOCI which could possibly detect other glycosides present in plasma derived from Lily of the Valley plant.^[1]

References

↑ Welsh, K. J.; Huang, R. S. P.; Actor, J. K.; Dasgupta, A. (2014). "Rapid Detection of the Active Cardiac Glycoside Convallatoxin of Lily of the Valley Using LOCI Digoxin Assay". American Journal of Clinical Pathology. 142 (3): 307. doi:10.1309/AJCPCOXF0O5XXTKD. PMID 25125619.

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[1] Welsh, K. J.; Huang, R. S. P.; Actor, J. K.; Dasgupta, A. (2014). "Rapid Detection of the Active Cardiac Glycoside Convallatoxin of Lily of the Valley Using LOCI Digoxin Assay". American Journal of Clinical Pathology. 142 (3): 307. doi:10.1309/AJCPCOXF0O5XXTKD. PMID 25125619.