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CHEBI:136430 - acetylseneciphylline

ChEBI IDCHEBI:136430
ChEBI Nameacetylseneciphylline
Stars
DefinitionA pyrrolizine alkaloid that is seneciphylline in which the hydroxy hydrogen has been replaced by an acetyl group.
Last Modified8 February 2018
SubmitterKeeva
DownloadsMolfile
FormulaC20H25NO6
Net Charge0
Average Mass375.421
Monoisotopic Mass375.16819
SMILES[H][C@]12C3=CCN1CC[C@H]2OC(=O)/C(=C\C)CC(=C)[C@@](C)(OC(C)=O)C(=O)OC3
InChIInChI=1S/C20H25NO6/c1-5-14-10-12(2)20(4,27-13(3)22)19(24)25-11-15-6-8-21-9-7-16(17(15)21)26-18(14)23/h5-6,16-17H,2,7-11H2,1,3-4H3/b14-5-/t16-,17-,20-/m1/s1
InChIKeyCTCKXBIRQMSUIU-BYVYPXNKSA-N
Species of MetaboliteComponentSourceComments
Jacobaea (ncbitaxon:405757)
leaf (BTO:0000713) MetaboLights (MTBLS429)
leaf (BTO:0000713) DOI (10.1007/s11306-017-1184-0)
Senecio pterophorus (ncbitaxon:82364) whole plant (BTO:0001461) PubMed (25269662)
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 (CHEBI:136430) has functional parent seneciphylline (CHEBI:9108)
acetylseneciphylline (CHEBI:136430) has role Jacobaea metabolite (CHEBI:139566)
acetylseneciphylline (CHEBI:136430) is a acetate ester (CHEBI:47622)
acetylseneciphylline (CHEBI:136430) is a macrocyclic lactone (CHEBI:63944)
acetylseneciphylline (CHEBI:136430) is a olefinic compound (CHEBI:78840)
acetylseneciphylline (CHEBI:136430) is a organic heterotricyclic compound (CHEBI:26979)
acetylseneciphylline (CHEBI:136430) is a pyrrolizine alkaloid (CHEBI:38521)
IUPAC Name 
(3Z,6R,14aR,14bR)-3-ethylidene-6-methyl-5-methylidene-2,7-dioxo-2,3,4,5,6,7,9,11,13,14,14a,14b-dodecahydro[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizin-6-yl acetate
Synonyms  Source
O-acetylseneciphyllineChEBI
Seneciphylline acetateKNApSAcK
(15Z)-11,16-dioxo-13,19-didehydrosenecionan-12-yl acetateChEBI
Manual XrefsDatabases
28424469ChemSpider
C00026182KNApSAcK
Registry NumbersSources
Reaxys:6668336Reaxys
CAS:90341-45-0ChemIDplus
Citations