CHEBI:156448 - loline

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ChEBI Name loline
ChEBI ID CHEBI:156448
Definition A loline alkaloid with formula C8H14N2O.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Martin Larralde
Supplier Information
Download Molfile XML SDF
Formula C8H14N2O
Net Charge 0
Average Mass 154.213
Monoisotopic Mass 154.11061
InChI InChI=1S/C8H14N2O/c1-9-7-6-4-10-3-2-5(11-6)8(7)10/h5-9H,2-4H2,1H3/t5-,6+,7-,8+/m0/s1
InChIKey OPMNROCQHKJDAQ-FKSUSPILSA-N
SMILES [H][C@]12[C@@H]3CCN1C[C@@H](O3)[C@@H]2NC
Metabolite of Species Details
Epichloe uncinata (NCBI:txid5050) Cluster GenBank: AY723749.1 See: PubMed
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): fungal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
(via loline alkaloid )
mycotoxin
Poisonous substance produced by fungi.
(via loline alkaloid )
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
Application(s): insecticide
Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.
(via loline alkaloid )
antifeedant
A substance that prevents pests from feeding.
(via loline alkaloid )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing loline (CHEBI:156448) is a loline alkaloid (CHEBI:156445)
loline (CHEBI:156448) is a secondary amino compound (CHEBI:50995)
IUPAC Name
(1S,6R,7R,7aS)-N-methylhexahydro-1H-1,6-epoxypyrrolizin-7-amine
Synonyms Sources
(+)-loline KNApSAcK
(1R,3S,7S,8R)-N-methyl-2-oxa-6-azatricyclo[4.2.1.03,7]nonan-8-amine IUPAC
festucine ChemIDplus
lolina SUBMITTER
Manual Xrefs Databases
16735876 ChemSpider
C00023609 KNApSAcK
View more database links
Registry Number Type Source
25161-91-5 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
15654104 PubMed citation SUBMITTER
17346759 PubMed citation Europe PMC
18655839 PubMed citation Europe PMC
25611615 PubMed citation Europe PMC
26349576 PubMed citation Europe PMC
26688468 PubMed citation Europe PMC
2719386 PubMed citation Europe PMC
33557353 PubMed citation Europe PMC
8067623 PubMed citation Europe PMC
Last Modified
15 April 2021