K-Strophanthidin

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k-Strophanthidin

Names
IUPAC name 3β,5,14-Trihydroxy-5β-card-20(22)-enolid-19-al
Systematic IUPAC name (1R,3aS,3bR,5aS,7S,9aS,9bS,11aR)-3a,5a,7-Trihydroxy-11a-methyl-1-(5-oxo-2,5-dihydrofuran-3-yl)hexadecahydro-9aH-cyclopenta[a]phenanthrene-9a-carbaldehyde
Other names 3β,5,14-Trihydroxy-19-oxo-5β,20(22)-cardenolide, Cymarigenen, Strophanthidin
Identifiers
CAS Number	66-28-4 [1] Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL111743 N
ChemSpider	5950 N
ECHA InfoCard	100.000.569
MeSH	Strophanthidin
PubChem CID	6185
UNII	W5O632DN33 N
CompTox Dashboard (EPA)	DTXSID00903966
InChI InChI=1S/C23H32O6/c1-20-6-3-17-18(4-8-22(27)11-15(25)2-7-21(17,22)13-24)23(20,28)9-5-16(20)14-10-19(26)29-12-14/h10,13,15-18,25,27-28H,2-9,11-12H2,1H3/t15-,16+,17-,18+,20+,21-,22-,23-/m0/s1 N Key: ODJLBQGVINUMMR-HZXDTFASSA-N N InChI=1/C23H32O6/c1-20-6-3-17-18(4-8-22(27)11-15(25)2-7-21(17,22)13-24)23(20,28)9-5-16(20)14-10-19(26)29-12-14/h10,13,15-18,25,27-28H,2-9,11-12H2,1H3/t15-,16+,17-,18+,20+,21-,22-,23-/m0/s1 Key: ODJLBQGVINUMMR-HZXDTFASBJ
SMILES C[C@]12CC[C@H]3[C@H]([C@]1(CC[C@@H]2C4=CC(=O)OC4)O)CC[C@]5([C@@]3(CC[C@@H](C5)O)C=O)O
Properties
Chemical formula	C23H32O6
Molar mass	404.5 g/mol
Density	1.43 g/mL
Melting point	169 °C (336 °F; 442 K)
Boiling point	620.7 °C (1,149.3 °F; 893.9 K)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Toxic
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

k-Strophanthidin is a cardenolide found in species of the genus Strophanthus. It is the aglycone of k-strophanthin, an analogue of ouabain. k-strophanthin is found in the ripe seeds of Strophanthus kombé and in the lily Convallaria.

K-Strophantidin can be differentiated into^{[citation needed]}:

• k-Strophanthin-α, h-Strophanthin, Cymarin, Strophanthidin-D-cymarosid (CAS: 508-77-0)
• k-Strophanthin-β, k-Strophanthin, Strophosid, Strophanthidin-glucocymarosid (CAS: 560-53-2)
• k-Strophanthin-γ,k-Strophanthosid, Strophanthidin-diglucocymarosid (CAS: 33279-57-1)
• Convallatoxin or Strophanthidin-L-rhamnosid (CAS: 508-75-8)
• Convallosid or Strophanthidin-glucorhamnosid (CAS: 13473-51-3)

Strophantidin is a cardiac glycoside which mechanism of action is similar to Digitalis, Ouabain and digitoxin. It specifically inhibits the membrane protein Na+/ K+ ATPase in muscle tissue (heart) which can lead to Ca2+ overload, diastolic dysfunction, arrythmias and ultimately to heart failure and death. Native African tribes used Strophantidin among other toxins as arrow poison.