CHEBI:136462 - erucifoline

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ChEBI Name erucifoline
Definition A pyrrolizine alkaloid that is produced by several Jacobaea species and displays toxicity towards insect herbivores.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C18H23NO6
Net Charge 0
Average Mass 349.379
Monoisotopic Mass 349.15254
InChI InChI=1S/C18H23NO6/c1-3-11-8-18(10-20)17(2,25-18)16(22)23-9-12-4-6-19-7-5-13(14(12)19)24-15(11)21/h3-4,13-14,20H,5-10H2,1-2H3/b11-3-/t13-,14-,17+,18+/m1/s1
SMILES C/1(\C[C@]2(O[C@]2(C(=O)OCC3=CCN4CC[C@@H](OC1=O)[C@@]34[H])C)CO)=C/C
Metabolite of Species Details
Jacobaea aquatica (NCBI:txid189230) See: PubMed
Jacobaea (NCBI:txid405757) Found in leaf (BTO:0000713). See: MetaboLights Study
Jacobaea (NCBI:txid405757) Found in leaf (BTO:0000713). See: DOI
Jacobaea vulgaris (NCBI:txid98722) 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): Jacobaea metabolite
Any plant metabolite that is produced by the genus Jacobaea.
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing erucifoline (CHEBI:136462) has functional parent senecionan (CHEBI:36330)
erucifoline (CHEBI:136462) has role Jacobaea metabolite (CHEBI:139566)
erucifoline (CHEBI:136462) has role insecticide (CHEBI:24852)
erucifoline (CHEBI:136462) is a epoxide (CHEBI:32955)
erucifoline (CHEBI:136462) is a macrocyclic lactone (CHEBI:63944)
erucifoline (CHEBI:136462) is a olefinic compound (CHEBI:78840)
erucifoline (CHEBI:136462) is a organic heteropentacyclic compound (CHEBI:38164)
erucifoline (CHEBI:136462) is a primary alcohol (CHEBI:15734)
erucifoline (CHEBI:136462) is a pyrrolizine alkaloid (CHEBI:38521)
erucifoline (CHEBI:136462) is a tertiary amino compound (CHEBI:50996)
Incoming acetylerucifoline (CHEBI:136464) has functional parent erucifoline (CHEBI:136462)
acetylerucifoline N-oxide (CHEBI:136465) has functional parent erucifoline (CHEBI:136462)
erucifoline N-oxide (CHEBI:136463) has functional parent erucifoline (CHEBI:136462)
Manual Xref Database
57579891 ChemSpider
View more database links
Registry Numbers Types Sources
40158-95-0 CAS Registry Number ChemIDplus
5456751 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11978435 PubMed citation Europe PMC
15081286 PubMed citation Europe PMC
21819407 PubMed citation Europe PMC
21969251 PubMed citation Europe PMC
24981118 PubMed citation Europe PMC
25607464 PubMed citation Europe PMC
28267991 PubMed citation Europe PMC
29377789 PubMed citation Europe PMC
IND22014228 Agricola citation Europe PMC
Last Modified
09 February 2018