Structure via PubChem · Public domain (PubChem)
akuammicine
Sign in to saveAlso known as Methyl (19E)-2,16,19,20-tetradehydrocuran-17-oate
Akuammicine is a monoterpene indole alkaloid of the Vinca sub-group. It is found in the Apocynaceae family of plants including Picralima nitida, Vinca minor and the Aspidosperma.
Chemical data
- Formula
- C20H22N2O2
- Molecular weight
- 322.4 g/mol
- IUPAC name
- methyl (1R,11S,12E,17S)-12-ethylidene-8,14-diazapentacyclo[9.5.2.01,9.02,7.014,17]octadeca-2,4,6,9-tetraene-10-carboxylate
- SMILES
- C/C=C\1/CN2CC[C@@]34[C@@H]2C[C@@H]1C(=C3NC5=CC=CC=C45)C(=O)OC
- InChIKey
- AGZMFTKKLPHOMT-DUJTVWLASA-N
- XLogP
- 2.4
- Polar surface area
- 41.6 Ų
- H-bond donors
- 1
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Mass
- 322.168128
Show 5 more facts
- found in taxon
- Tabernaemontana humblotii
- chemical formula
- C₂₀H₂₂N₂O₂
- canonical SMILES
- CC=C1CN2CCC34C2CC1C(=C3NC5=CC=CC=C45)C(=O)OC
- isomeric SMILES
- C/C=C\1/CN2CC[C@@]34[C@@H]2C[C@@H]1C(=C3NC5=CC=CC=C45)C(=O)OC
- Commons category
- Akuammicine
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
8 sectionsContents
- History
- Natural occurrence
- Synthesis
- Biosynthesis
- Chemical synthesis
- Research
- See also
- References
Akuammicine is a monoterpene indole alkaloid of the Vinca sub-group. It is found in the Apocynaceae family of plants including Picralima nitida, Vinca minor and the Aspidosperma.
==History== The alkaloids are a large group of natural products which are classified according to the part-structure which members of a particular group contain. Akuammicine is a monoterpene indole alkaloid of the Vinca sub-group which shares a common biosynthesis with other members, namely that they are derived from strictosidine. It was first isolated in 1927 and had been investigated by Sir Robert Robinson and others before its structure was correctly deduced. This was confirmed by X-ray crystallography in 2017.
Excerpted from Wikipedia’s “akuammicine” article, available under the CC BY-SA 4.0 licence.