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CHEBI:136465 - acetylerucifoline N-oxide

ChEBI IDCHEBI:136465
ChEBI Nameacetylerucifoline N-oxide
Stars
ASCII Nameacetylerucifoline N-oxide
DefinitionA pyrrolizine alkaloid that is erucifoline in which the primary hydroxy hydrogen has been replaced by an acetyl group and the tertiary amino function has been oxidised to the corresponding N-oxide.
Last Modified9 February 2018
SubmitterKeeva
DownloadsMolfile
FormulaC20H25NO8
Net Charge0
Average Mass407.419
Monoisotopic Mass407.15802
SMILES[H][C@]12C3=CC[N+]1([O-])CC[C@H]2OC(=O)/C(=C\C)C[C@@]1(COC(C)=O)O[C@@]1(C)C(=O)OC3
InChIInChI=1S/C20H25NO8/c1-4-13-9-20(11-27-12(2)22)19(3,29-20)18(24)26-10-14-5-7-21(25)8-6-15(16(14)21)28-17(13)23/h4-5,15-16H,6-11H2,1-3H3/b13-4-/t15-,16-,19+,20+,21?/m1/s1
InChIKeyWLZGBUHDZWPQMM-NBDNSDISSA-N
Species of MetaboliteComponentSourceComments
Jacobaea (ncbitaxon:405757)
leaf (BTO:0000713) DOI (10.1007/s11306-017-1184-0)
leaf (BTO:0000713) MetaboLights (MTBLS429)
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)
acetylerucifoline N-oxide (CHEBI:136465) has functional parent erucifoline (CHEBI:136462)
acetylerucifoline N-oxide (CHEBI:136465) has role Jacobaea metabolite (CHEBI:139566)
acetylerucifoline N-oxide (CHEBI:136465) is a acetate ester (CHEBI:47622)
acetylerucifoline N-oxide (CHEBI:136465) is a epoxide (CHEBI:32955)
acetylerucifoline N-oxide (CHEBI:136465) is a macrocyclic lactone (CHEBI:63944)
acetylerucifoline N-oxide (CHEBI:136465) is a olefinic compound (CHEBI:78840)
acetylerucifoline N-oxide (CHEBI:136465) is a organic heteropentacyclic compound (CHEBI:38164)
acetylerucifoline N-oxide (CHEBI:136465) is a pyrrolizine alkaloid (CHEBI:38521)
acetylerucifoline N-oxide (CHEBI:136465) is a tertiary amine oxide (CHEBI:134363)
IUPAC Name 
[(5aR,8Z,9aS,10aR,13bR)-8-ethylidene-10a-methyl-3,7,11-trioxo-2,4,5,5a,8,9,10a,11,13,13b-decahydro-3H-3λ5-oxireno[8,9][1,6]dioxacyclododecino[2,3,4-gh]pyrrolizin-9a(7H)-yl]methyl acetate
Synonym  Source
O-acetylerucifoline N-oxideChEBI