CHEBI:2909 - atisine

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ChEBI Name atisine
ChEBI ID CHEBI:2909
Definition A organic heterohexacyclic compound and diterpene alkaloid isolated from Aconitum anthora. In solution, it is a 2:1 mixture of readily interconvertible epimers at position 20 (the carbon attached to both the nitrogen and an oxygen atom).
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C22H33NO2
Net Charge 0
Average Mass 343.504
Monoisotopic Mass 343.25113
InChI InChI=1S/C22H33NO2/c1-14-15-4-8-21(18(14)24)9-5-16-20(2)6-3-7-22(16,17(21)12-15)19-23(13-20)10-11-25-19/h15-19,24H,1,3-13H2,2H3/t15-,16+,17+,18+,19?,20-,21-,22-/m0/s1
InChIKey KWVIBDAKHDJCNY-LHCLZMBSSA-N
SMILES C1CC[C@]2(CN3CCOC3([C@]41[C@]5([C@@]6(CC[C@@]42[H])CC[C@@H](C5)C([C@H]6O)=C)[H])[H])C
Roles Classification
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
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ChEBI Ontology
Outgoing atisine (CHEBI:2909) has role plant metabolite (CHEBI:76924)
atisine (CHEBI:2909) is a diterpene alkaloid (CHEBI:23847)
atisine (CHEBI:2909) is a organic heterohexacyclic compound (CHEBI:51914)
atisine (CHEBI:2909) is a secondary alcohol (CHEBI:35681)
atisine (CHEBI:2909) is a terpene alkaloid fundamental parent (CHEBI:38525)
IUPAC Name
atisine
Synonyms Sources
Anthorine ChemIDplus
Atisine KEGG COMPOUND
Manual Xrefs Databases
C00001616 KNApSAcK
C08660 KEGG COMPOUND
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Registry Numbers Types Sources
1085811 Reaxys Registry Number Reaxys
466-43-3 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
22193953 PubMed citation Europe PMC
25004408 PubMed citation Europe PMC
25153874 PubMed citation Europe PMC
25159015 PubMed citation Europe PMC
25239552 PubMed citation Europe PMC
Last Modified
04 January 2016
General Comment
2016-01-04 For details of the epimeric mixture, see J. Chem. Soc. D, 1970, 644-645 (An exceptionally ready interconversion of configurational isomers in atisine; S. K. Pradhan and V. M. Girijavallabhan) DOI: 10.1039/C29700000644 and J. Am. Chem. Soc., 1977, 99 (1), 284-286 (The conformational analysis of the E and F rings of atisine, veatchine, and related alkaloids. The existence of C-20 epimers; S. W. Pelletier and N. V. Mody) DOI: 10.1021/ja00443a069