CHEBI:136451 - jacobine N-oxide

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ChEBI Name jacobine N-oxide
ChEBI ID CHEBI:136451
ChEBI ASCII Name jacobine N-oxide
Definition A pyrrolizine alkaloid that is jacobine in which the tertiary amino function has been oxidised to the corresponding N-oxide.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C18H25NO7
Net Charge 0
Average Mass 367.394
Monoisotopic Mass 367.16310
InChI InChI=1S/C18H25NO7/c1-10-8-18(11(2)26-18)16(21)25-13-5-7-19(23)6-4-12(14(13)19)9-24-15(20)17(10,3)22/h4,10-11,13-14,22H,5-9H2,1-3H3/t10-,11+,13-,14-,17-,18+,19?/m1/s1
InChIKey NKRQJWQYBNTAEV-SAJQNFQWSA-N
SMILES [C@@]12([C@H](C)O1)C(O[C@H]3[C@@]4([N+](CC=C4COC([C@]([C@@H](C2)C)(C)O)=O)(CC3)[O-])[H])=O
Metabolite of Species Details
Jacobaea (NCBI:txidtxid405757) Found in leaf (BTO:0000713). See: DOI
Jacobaea (NCBI:txidtxid405757) Found in leaf (BTO:0000713). See: MetaboLights Study
Roles Classification
Biological Role(s): Jacobaea metabolite
Any plant metabolite that is produced by the genus Jacobaea.
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing jacobine N-oxide (CHEBI:136451) has functional parent jacobine (CHEBI:6080)
jacobine N-oxide (CHEBI:136451) has role Jacobaea metabolite (CHEBI:139566)
jacobine N-oxide (CHEBI:136451) has role insecticide (CHEBI:24852)
jacobine N-oxide (CHEBI:136451) is a macrocyclic lactone (CHEBI:63944)
jacobine N-oxide (CHEBI:136451) is a organic heterotricyclic compound (CHEBI:26979)
jacobine N-oxide (CHEBI:136451) is a pyrrolizine alkaloid (CHEBI:38521)
jacobine N-oxide (CHEBI:136451) is a spiro-epoxide (CHEBI:133131)
jacobine N-oxide (CHEBI:136451) is a tertiary alcohol (CHEBI:26878)
jacobine N-oxide (CHEBI:136451) is a tertiary amine oxide (CHEBI:134363)
IUPAC Name
(3S,3'S,5R,6R,14aR,14bR)-6-hydroxy-3',5,6-trimethyl-12-oxo-5,6,11,12,13,14,14a,14b-octahydro-2H,9H-spiro[1,6-dioxacyclododecino[2,3,4-gh]pyrrolizine-3,2'-oxirane]-2,7(4H)-dione
Registry Number Type Source
20340584 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
28267991 PubMed citation Europe PMC
Last Modified
08 February 2018