Bufotalin

Bufotalin is a cardiotoxic bufanolide steroid, cardiac glycoside analogue, secreted by a number of toad species. Bufotalin can be extracted from the skin parotoid glands of several types of toad.

Bufotalin
Names
IUPAC name
3β,14-Dihydroxy-5β-bufa-20,22-dienolid-16β-yl acetate
Systematic IUPAC name
(1R,2S,3aS,3bR,5aR,7S,9aS,9bS,11aR)-3a,7-Dihydroxy-9a,11a-dimethyl-1-(1-oxo-1H-oxan-5-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-2-yl acetate
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
  • InChI=1S/C26H36O6/c1-15(27)32-21-13-26(30)20-6-5-17-12-18(28)8-10-24(17,2)19(20)9-11-25(26,3)23(21)16-4-7-22(29)31-14-16/h4,7,14,17-21,23,28,30H,5-6,8-13H2,1-3H3/t17-,18+,19+,20-,21+,23+,24+,25-,26+/m1/s1 Y
    Key: VOZHMAYHYHEWBW-NVOOAVKYSA-N Y
  • InChI=1/C26H36O6/c1-15(27)32-21-13-26(30)20-6-5-17-12-18(28)8-10-24(17,2)19(20)9-11-25(26,3)23(21)16-4-7-22(29)31-14-16/h4,7,14,17-21,23,28,30H,5-6,8-13H2,1-3H3/t17-,18+,19+,20-,21+,23+,24+,25-,26+/m1/s1
    Key: VOZHMAYHYHEWBW-NVOOAVKYBX
SMILES
  • CC(=O)O[C@H]1C[C@@]2(C3CC[C@@H]4C[C@H](CC[C@@]4(C3CC[C@@]2([C@H]1C5=COC(=O)C=C5)C)C)O)O
Properties
C26H36O6
Molar mass 444.568 g·mol−1
Appearance crystalline solid
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Toxic
Lethal dose or concentration (LD, LC):
LD50 (median dose)
 4.13 mg·kg−1 (mouse, IV)

0.4 mg·kg−1 (mouse, SC)
0.136 mg·kg−1 (cat, IV)

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references
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