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CHEBI:136454 - jacoline N-oxide

ChEBI IDCHEBI:136454
ChEBI Namejacoline N-oxide
Stars
ASCII Namejacoline N-oxide
DefinitionA pyrrolizine alkaloid that is jacoline in which the tertiary amino function has been oxidised to the corresponding N-oxide.
Last Modified8 February 2018
SubmitterKeeva
DownloadsMolfile
FormulaC18H27NO8
Net Charge0
Average Mass385.413
Monoisotopic Mass385.17367
SMILES[H][C@]12C3=CC[N+]1([O-])CC[C@H]2OC(=O)[C@@](O)([C@@H](C)O)C[C@@H](C)[C@@](C)(O)C(=O)OC3
InChIInChI=1S/C18H27NO8/c1-10-8-18(24,11(2)20)16(22)27-13-5-7-19(25)6-4-12(14(13)19)9-26-15(21)17(10,3)23/h4,10-11,13-14,20,23-24H,5-9H2,1-3H3/t10-,11-,13-,14-,17-,18+,19?/m1/s1
InChIKeyGIQXQZKTWHFVAB-YVLLADMLSA-N
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.
ChEBI Ontology
Outgoing Relation(s)
jacoline N-oxide (CHEBI:136454) has functional parent jacoline (CHEBI:136452)
jacoline N-oxide (CHEBI:136454) has role Jacobaea metabolite (CHEBI:139566)
jacoline N-oxide (CHEBI:136454) is a macrocyclic lactone (CHEBI:63944)
jacoline N-oxide (CHEBI:136454) is a organic heterotricyclic compound (CHEBI:26979)
jacoline N-oxide (CHEBI:136454) is a pyrrolizine alkaloid (CHEBI:38521)
jacoline N-oxide (CHEBI:136454) is a tertiary amine oxide (CHEBI:134363)
jacoline N-oxide (CHEBI:136454) is a triol (CHEBI:27136)
IUPAC Name 
(3S,5R,6R,14aR,14bR)-3,6-dihydroxy-3-[(1R)-1-hydroxyethyl]-5,6-dimethyl-12-oxo-3,4,5,6,11,12,13,14,14a,14b-decahydro-9H-12λ5-[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione