seneciphyllinine Chemical Properties

Boiling point:

585.3±50.0 °C(Predicted)

Density 

1.25±0.1 g/cm3(Predicted)

pka

5.79±0.40(Predicted)

InChI

InChI=1S/C20H25NO6/c1-5-14-10-12(2)20(4,27-13(3)22)19(24)25-11-15-6-8-21-9-7-16(17(15)21)26-18(14)23/h5-6,16-17H,2,7-11H2,1,3-4H3/b14-5-/t16-,17-,20-/m1/s1

InChIKey

CTCKXBIRQMSUIU-BYVYPXNKSA-N

SMILES

N12CC=C3COC(=O)[C@@](OC(C)=O)(C)C(=C)C/C(=C/C)/C(=O)O[C@@]([H])([C@]13[H])CC2

seneciphyllinine Usage And Synthesis

Uses

Seneciphyllinine, a pyrrolizidine alkaloid, is isolated from the roots of Gynura japonica. Pyrrolizidine alkaloids are highly hepatotoxic natural chemicals that produce irreversible chronic and acute hepatotoxic effects on human beings[1].

Definition

ChEBI: Acetylseneciphylline is a pyrrolizine alkaloid that is seneciphylline in which the hydroxy hydrogen has been replaced by an acetyl group. It has a role as a Jacobaea metabolite. It is a macrocyclic lactone, an olefinic compound, an organic heterotricyclic compound, a pyrrolizine alkaloid and an acetate ester. It is functionally related to a seneciphylline.

References

[1] Fang L, et al. Mass-spectrometry-directed analysis and purification of pyrrolizidine alkaloid cis/trans isomers in Gynura japonica. J Sep Sci. 2014 Aug;37(15):2032-8. DOI:10.1002/jssc.201400314

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