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CHEBI:136451 - jacobine N-oxide

ChEBI IDCHEBI:136451
ChEBI Namejacobine N-oxide
Stars
ASCII Namejacobine N-oxide
DefinitionA pyrrolizine alkaloid that is jacobine in which the tertiary amino function has been oxidised to the corresponding N-oxide.
Last Modified8 February 2018
SubmitterKeeva
DownloadsMolfile
FormulaC18H25NO7
Net Charge0
Average Mass367.398
Monoisotopic Mass367.16310
SMILES[H][C@]12C3=CC[N+]1([O-])CC[C@H]2OC(=O)[C@@]1(C[C@@H](C)[C@@](C)(O)C(=O)OC3)O[C@H]1C
InChIInChI=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
InChIKeyNKRQJWQYBNTAEV-SAJQNFQWSA-N
Species of MetaboliteComponentSourceComments
Jacobaea (ncbitaxon:405757)
leaf (BTO:0000713) MetaboLights (MTBLS429)
leaf (BTO:0000713) DOI (10.1007/s11306-017-1184-0)
Roles Classification
Biological Roles:
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.
Application:
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.
ChEBI Ontology
Outgoing Relation(s)
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 NumbersSources
Reaxys:20340584Reaxys
Citations