Stemmadenine

Stemmadenine
Names
	IUPAC name Methyl (1R,2S,16E)-16-ethylidene-2-(hydroxymethyl)-4,14-diazatetracyclo[12.2.2.03,11.05,10]octadeca-3(11),5,7,9-tetraene-2-carboxylate
Identifiers
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:9260;
ChemSpider	8242264;
PubChem CID	10066724;
	InChI InChI=1S/C21H26N2O3/c1-3-14-12-23-10-8-16-15-6-4-5-7-18(15)22-19(16)21(13-24,20(25)26-2)17(14)9-11-23/h3-7,17,22,24H,8-13H2,1-2H3/b14-3-/t17-,21+/m1/s1 Key: MBXJCHZRHROMQA-YVDMJPQFSA-N; InChI=1/C21H26N2O3/c1-3-14-12-23-10-8-16-15-6-4-5-7-18(15)22-19(16)21(13-24,20(25)26-2)17(14)9-11-23/h3-7,17,22,24H,8-13H2,1-2H3/b14-3-/t17-,21+/m1/s1 Key: MBXJCHZRHROMQA-YVDMJPQFBN;
	SMILES C/C=C\1/CN2CC[C@H]1[C@](C3=C(CC2)C4=CC=CC=C4N3)(CO)C(=O)OC;
Properties
Chemical formula	C21H26N2O3
Molar mass	354.450 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

Stemmadenine is a terpene indole alkaloid. Stemmadenine is believed to be formed from preakuammicine by a carbon-carbon bond cleavage. Cleavage of a second carbon-carbon bond is thought to form dehydrosecodine.[1] The enzymes forming stemmadenine and using it as a substrate remain unknown to date.

References

Scott, Alastair I; Qureshi, Asaf A (1969). "Biogenesis of Strychnos, Aspidosperma, and Iboga alkaloids. Structure and reactions of preakuammicine". Journal of the American Chemical Society. 91 (21): 5874. doi:10.1021/ja01049a032. PMID 5812148.

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.

[1] Scott, Alastair I; Qureshi, Asaf A (1969). "Biogenesis of Strychnos, Aspidosperma, and Iboga alkaloids. Structure and reactions of preakuammicine". Journal of the American Chemical Society. 91 (21): 5874. doi:10.1021/ja01049a032. PMID 5812148.