Bufadienolide

Bufadienolide
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
	PubChem	3035030
ChemSpider	26286947 Y
Jmol-3D images	Image 1
SMILES CC14CCC3C2(C)CCCCC2CCC3C1CCC4c5ccc(=O)oc5
InChI 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 Y Key: YBPMPRDOWHIVNA-JTSGVHQASA-N Y 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
Properties
Molecular formula	C24H34O2
Molar mass	354.53 g mol−1
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Bufadienolide is a type of steroid. 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 are heart-arresting.

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.

Classification

According to MeSH, bufadienolides and bufanolides are classified as follows:

• Polycyclic compounds
  • Steroids

• • Cardanolides

• • • • Cardenolides
      • Cardiac glycosides

• • • • Bufanolides

• • • • Bufenolides
      • Bufadienolides

• • • • • • • Proscillaridin
            • Daigremontianin

• • • • Cardenolides

Note that cardenolides have been classified under cardanolides as well as cardiac glycosides in this classification.