Bufadienolide

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Bufadienolide
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Names
IUPAC name
5-[(5R, 8R,9S,10S,13S,14S,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]pyran-2-one
Identifiers
ChEBI CHEBI:83977 N
ChemSpider 26286947 YesY
Jmol 3D model Interactive image
PubChem 3035030
  • InChI=1S/C24H34O2/c1-23-13-4-3-5-17(23)7-8-18-20-10-9-19(16-6-11-22(25)26-15-16)24(20,2)14-12-21(18)23/h6,11,15,17-21H,3-5,7-10,12-14H2,1-2H3/t17-,18-,19+,20+,21-,23-,24+/m0/s1 YesY
    Key: YBPMPRDOWHIVNA-JTSGVHQASA-N YesY
  • InChI=1S/C24H34O2/c1-23-13-4-3-5-17(23)7-8-18-20-10-9-19(16-6-11-22(25)26-15-16)24(20,2)14-12-21(18)23/h6,11,15,17-21H,3-5,7-10,12-14H2,1-2H3/t17-,18-,19+,20+,21-,23-,24+/m0/s1
    Key: YBPMPRDOWHIVNA-JTSGVHQASA-N
  • CC14CCC3C2(C)CCCCC2CCC3C1CCC4c5ccc(=O)oc5
Properties
C24H34O2
Molar mass 354.53 g·mol−1
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Bufadienolide is a chemical compound with steroid structure. Its derivatives are collectively known as bufadienolides, including many in the form of bufadienolide glycosides (bufadienolides that contain structural groups derived from sugars). These are a type of cardiac glycoside, the other being the cardenolide glycosides. Both bufadienolides and their glycosides are toxic; specifically, they can cause an atrioventricular block, bradycardia (slow heartbeat), ventricular tachycardia (a type of rapid heartbeat), and possibly lethal cardiac arrest.[1]

Etymology

The term derives from the toad genus Bufo that contains bufadienolide glycosides, the suffix -adien- that refers to the two double bonds in the lactone ring, and the ending -olide that denotes the lactone structure. Consequently, related structures with only one double bond are called bufenolides,[citation needed] and the saturated equivalent is bufanolide.[2]

File:Bufanolide structure.png
Bufanolide

Classification

According to MeSH, bufadienolides and bufanolides are classified as follows:[3][4]

Cardenolides have been classified under cardanolides as well as cardiac glycosides in this classification.

References

  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ IUPAC Recommendations 1999: Revised Section F: Natural Products and Related Compounds
  3. ↑ Bufadienolides at the US National Library of Medicine Medical Subject Headings (MeSH)
  4. ↑ Cardenolides at the US National Library of Medicine Medical Subject Headings (MeSH)


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