Dehydrosecodine
Names
Preferred IUPAC name
Methyl 2-{3-[2-(5-ethylpyridin-1(2H)-yl)ethyl]-1H-indol-2-yl}prop-2-enoate
Other names
Methyl 2-{3-[2-(5-ethyl-1(2H)-pyridinyl)ethyl]-1H-indol-2-yl}acrylate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
  • InChI=1S/C21H24N2O2/c1-4-16-8-7-12-23(14-16)13-11-18-17-9-5-6-10-19(17)22-20(18)15(2)21(24)25-3/h5-10,14,22H,2,4,11-13H2,1,3H3
    Key: FGHJSNGBTCVANJ-UHFFFAOYSA-N
  • InChI=1/C21H24N2O2/c1-4-16-8-7-12-23(14-16)13-11-18-17-9-5-6-10-19(17)22-20(18)15(2)21(24)25-3/h5-10,14,22H,2,4,11-13H2,1,3H3
    Key: FGHJSNGBTCVANJ-UHFFFAOYAS
  • CCC1=CN(CC=C1)CCc2c3ccccc3[nH]c2C(=C)C(=O)OC
Properties
C21H24N2O2
Molar mass 336.435 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Dehydrosecodine is a terpene indole alkaloid. The compound is believed to be an unstable O-acetylated secodine type intermediate in the formation of catharanthine and tabersonine from stemmadenine.[1] The enzymes involved forming dehydrosecodine or utilizing it as a substrate for further chemical reactions are currently unknown.

References

  1. ↑ Qu, Y., Easson, M. E., Simionescu, R., Hajicek, J., Thamm, A. M., Salim, V., & De Luca, V. (2018). Solution of the multistep pathway for assembly of corynanthean, strychnos, iboga, and aspidosperma monoterpenoid indole alkaloids from 19E-geissoschizine. Proceedings of the National Academy of Sciences, 115(12), 3180-3185.


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