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CHEBI:136449 - acetylseneciphylline N-oxide

ChEBI IDCHEBI:136449
ChEBI Nameacetylseneciphylline N-oxide
Stars
ASCII Nameacetylseneciphylline N-oxide
DefinitionA pyrrolizine alkaloid that is seneciphylline in which the hydroxy hydrogen has been replaced by an acetyl group and the tertiary amino function has been oxidised to the corresponding N-oxide.
Last Modified8 February 2018
SubmitterKeeva
DownloadsMolfile
FormulaC20H25NO7
Net Charge0
Average Mass391.420
Monoisotopic Mass391.16310
SMILES[H][C@]12C3=CC[N+]1([O-])CC[C@H]2OC(=O)/C(=C\C)CC(=C)[C@@](C)(OC(C)=O)C(=O)OC3
InChIInChI=1S/C20H25NO7/c1-5-14-10-12(2)20(4,28-13(3)22)19(24)26-11-15-6-8-21(25)9-7-16(17(15)21)27-18(14)23/h5-6,16-17H,2,7-11H2,1,3-4H3/b14-5-/t16-,17-,20-,21?/m1/s1
InChIKeyVUEKZTPMPCTKDK-NZQWTBGOSA-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.
ChEBI Ontology
Outgoing Relation(s)
acetylseneciphylline N-oxide (CHEBI:136449) has functional parent seneciphylline (CHEBI:9108)
acetylseneciphylline N-oxide (CHEBI:136449) has role Jacobaea metabolite (CHEBI:139566)
acetylseneciphylline N-oxide (CHEBI:136449) is a acetate ester (CHEBI:47622)
acetylseneciphylline N-oxide (CHEBI:136449) is a macrocyclic lactone (CHEBI:63944)
acetylseneciphylline N-oxide (CHEBI:136449) is a olefinic compound (CHEBI:78840)
acetylseneciphylline N-oxide (CHEBI:136449) is a organic heterotricyclic compound (CHEBI:26979)
acetylseneciphylline N-oxide (CHEBI:136449) is a pyrrolizine alkaloid (CHEBI:38521)
acetylseneciphylline N-oxide (CHEBI:136449) is a tertiary amine oxide (CHEBI:134363)
IUPAC Name 
(3Z,6R,14aR,14bR)-3-ethylidene-6-methyl-5-methylidene-2,7,12-trioxo-2,3,4,5,6,7,11,12,13,14,14a,14b-dodecahydro-9H-12λ5-[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizin-6-yl acetate
Synonyms  Source
(15Z)-12-acetoxy-11,16-dioxo-13,19-didehydrosenecionane N-oxideChEBI
(15Z)-12-acetoxy-11,16-dioxo-13,19-didehydrosenecionane 4-oxideChEBI
acetylseneciphylline oxideChEBI
Registry NumbersSources
Reaxys:21894091Reaxys
Citations