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Daigremontianin information


Daigremontianin
Names
IUPAC name
(1β,3β,5β,11α)-1,3,5-(ethylidynetris(oxy)-11,14-dihydroxy-12,19-dioxobufa-20,22-dienolide
Identifiers
CAS Number
  • 98205-50-6 checkY
3D model (JSmol)
  • Interactive image
  • Interactive image
ChemSpider
  • 112839 checkY
PubChem CID
  • 127105
UNII
  • N5SG3A9FLM checkY
CompTox Dashboard (EPA)
  • DTXSID40897532 Edit this at Wikidata
InChI
  • InChI=1S/C26H30O9/c1-22-15(13-3-4-18(28)32-11-13)6-8-26(22,31)16-5-7-24-10-14-9-17(34-23(2,33-14)35-24)25(24,12-27)19(16)20(29)21(22)30/h3-4,11-12,14-17,19-20,29,31H,5-10H2,1-2H3/t14-,15+,16+,17?,19+,20-,22-,23?,24?,25+,26-/m0/s1 checkY
    Key: PHOLEJIIASOWOL-SQBSQXRJSA-N checkY
  • InChI=1/C26H30O9/c1-22-15(13-3-4-18(28)32-11-13)6-8-26(22,31)16-5-7-24-10-14-9-17(34-23(2,33-14)35-24)25(24,12-27)19(16)20(29)21(22)30/h3-4,11-12,14-17,19-20,29,31H,5-10H2,1-2H3/t14-,15+,16+,17?,19+,20-,22-,23?,24?,25+,26-/m0/s1
    Key: PHOLEJIIASOWOL-SQBSQXRJBB
SMILES
  • C[C@@]12[C@@](CC[C@@H]2C(C=C3)=COC3=O)(O)[C@]4([H])CC[C@]5(OC6(C)O7)C[C@@H]7C[C@@H](O6)[C@]5(C=O)[C@@]4([H])[C@H](O)C1=O
  • O=C\1O\C=C(/C=C/1)[C@@H]6[C@]5(C(=O)[C@@H](O)[C@@H]7[C@]3(C=O)C4(OC2(O[C@@H](CC3O2)C4)C)CC[C@H]7[C@@]5(O)CC6)C
Properties
Chemical formula
 C26H30O9
Molar mass 486.517 g·mol−1
Density 1.49 g/mL
Boiling point 695.2 °C (1,283.4 °F; 968.4 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Daigremontianin is a bufadienolide. Bufadienolides are steroids and cardiac glycoside aglycones (meaning that they bind with carbohydrates to form cardiac glycosides) that are similar to cardenolides, differing only in the structure of the C-17 substituent on the D ring. This chemical has been found to be toxic in experiments on mice.[1][2] It is one of five bufadienolides that have been isolated from Kalanchoe daigremontiana.

  1. ^ Wagner, H.; Fischer, M.; Lotter, H. (1985). "Neue Bufadienolide von Kalanchoe daigremontiana Hamet et Perr. (Crassulaceae)" [New Bufadienolides from Kalanchoe daigremontiana Hamet et Perr. (Crassulaceae)]. Zeitschrift für Naturforschung B (in German). 40 (9): 1226–1227. doi:10.1515/znb-1985-0920. S2CID 95146056.
  2. ^ Wagner, H.; Lotter, H.; Fischer, M. (1986). "Die toxischen und sedierend wirkenden Bufadienolide von Kalanchoe daigremontiana Hamet et Perr" [The Toxic and Sedative Bufadienolides of Kalanchoe daigremontiana Hamet et Perr.]. Helvetica Chimica Acta (in German). 69 (2): 359–367. doi:10.1002/hlca.19860690215.

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Daigremontianin

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Daigremontianin is a bufadienolide. Bufadienolides are steroids and cardiac glycoside aglycones (meaning that they bind with carbohydrates to form cardiac...

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Kalanchoe

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bufadienolides have been isolated from Kalanchoe daigremontiana. Two of these, daigremontianin and bersaldegenin 1,3,5-orthoacetate, have been shown to have a pronounced...

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Cardiac glycoside

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eye): adonitoxin Kalanchoe daigremontiana and other Kalanchoe species: daigremontianin Erysimum cheiranthoides (wormseed wallflower) and other Erysimum species...

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Kalanchoe daigremontiana

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seeds. All parts of this species contain a very toxic steroid known as daigremontianin. It is often confused with Kalanchoe laetivirens, Kalanchoe delagoensis...

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Bufadienolide

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(includes bufenolides, bufadienolides, bufatrienolides) Proscillaridin Daigremontianin Cardenolides Mutschler, Ernst; Schäfer-Korting, Monika (2001). Arzneimittelwirkungen...

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