Cardenolide

Cardenolide
Names
IUPAC name
3-[(8R,9S,10S,13S,14R,17S)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C23H34O 2/c1-22-11-4-3-5-16(22)6-7-17-19-9-8-18(15-13-21(24)25-14-15)23(19,2)12-10-20(17)22/h4,11,15-20H,3,5-10,12-14H2,1-2H3/t15-,16?,17-,18+,19+,20-,22-,23+/m0/s1 checkY
    Key: NMLOFHCUVXKTGV-OCYOQFCJSA-N checkY
  • InChI=1/C23H34O2/c1-22-11-4-3-5-16(22)6-7-17-19-9-8-18(15-13-21(24)25-14-15)23(19,2)12-10-20(17)22/h4,11,15-20H,3,5-10,12-14H2,1-2H3/t15-,16?,17-,18+,19+,20-,22-,23+/m0/s1
    Key: NMLOFHCUVXKTGV-OCYOQFCJBM
  • CC12CCCCC1CCC3C2CCC4(C3C=CC4C5CC(=O)OC5)C
  • C[C@]52/C=C\CCC5CC[C@H]1[C@H]3CC[C@@H]([C@@]3(C)CC[C@@H]12)[C@H]4CC(=O)OC4
Properties
C23H34O2
Molar mass 342.51486
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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A cardenolide is a type of steroid. Many plants contain derivatives, collectively known as cardenolides, including many in the form of cardenolide glycosides (cardenolides that contain structural groups derived from sugars). Cardenolide glycosides are often toxic; specifically, they are heart-arresting. Cardenolides are toxic to animals through inhibition of the enzyme Na+/K+-ATPase, which is responsible for maintaining the sodium and potassium ion gradients across the cell membranes.[1]

  1. ^ Cite error: The named reference :0 was invoked but never defined (see the help page).