Structure via PubChem · Public domain (PubChem)
Magellanine
Sign in to save(−)-Magellanine is a member of the Lycopodium alkaloid class of natural products. It was isolated from the club moss Lycopodium magellanicum in 1976. It has been synthesized five times, with the first synthesis having been completed by the Larry E. Overman group at the University of California, Irvine in 1993. It has also been synthesized by the Leo Paquette group in 1993 at Ohio State University, the Chun-Chen Liao group in 2002 at National Tsing Hua University, the Miyuki Ishikazi and Tamiko Takahashi groups in 2005 at the Josai International University and Tokyo University of Science, and t
Chemical data
- Formula
- C17H25NO2
- Molecular weight
- 275.4 g/mol
- IUPAC name
- (1S,3S,8S,9R,10S,12S)-10-hydroxy-5,14-dimethyl-5-azatetracyclo[7.7.0.01,12.03,8]hexadec-14-en-16-one
via PubChem
Wikidata facts
- Subclass of
- alkaloid
- Mass
- 275.188529
Show 4 more facts
- chemical formula
- C₁₇H₂₅NO₂
- isomeric SMILES
- CC1=CC(=O)[C@]23C[C@@H]4CN(CC[C@@H]4[C@H]2[C@H](C[C@@H]3C1)O)C
- canonical SMILES
- CC1=CC(=O)C23CC4CN(CCC4C2C(CC3C1)O)C
- found in taxon
- Maytenus magellanica
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
(−)-Magellanine is a member of the Lycopodium alkaloid class of natural products. It was isolated from the club moss Lycopodium magellanicum in 1976. It has been synthesized five times, with the first synthesis having been completed by the Larry E. Overman group at the University of California, Irvine in 1993. It has also been synthesized by the Leo Paquette group in 1993 at Ohio State University, the Chun-Chen Liao group in 2002 at National Tsing Hua University, the Miyuki Ishikazi and Tamiko Takahashi groups in 2005 at the Josai International University and Tokyo University of Science, and the Chisato Mukai group in 2007 at the Kanazawa University. One partial synthesis was completed by the A. I. Meyers group in 1995 at Colorado State University.
Biosynthetically, it is thought to have been derived from lysine. This was determined by conducting feeding studies of radiolabeled precursors.
Excerpted from Wikipedia’s “Magellanine” article, available under the CC BY-SA 4.0 licence.