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CHEBI:136495 - dehydrojacoline

ChEBI IDCHEBI:136495
ChEBI Namedehydrojacoline
Stars
DefinitionA pyrrolizine alkaloid that is jacoline in which the 5-methyl group has been replaced by methylene.
Last Modified9 February 2018
SubmitterKeeva
DownloadsMolfile
FormulaC18H25NO7
Net Charge0
Average Mass367.398
Monoisotopic Mass367.16310
SMILES[H][C@]12C3=CCN1CC[C@H]2OC(=O)[C@@](O)([C@@H](C)O)CC(=C)[C@@](C)(O)C(=O)OC3
InChIInChI=1S/C18H25NO7/c1-10-8-18(24,11(2)20)16(22)26-13-5-7-19-6-4-12(14(13)19)9-25-15(21)17(10,3)23/h4,11,13-14,20,23-24H,1,5-9H2,2-3H3/t11-,13-,14-,17-,18+/m1/s1
InChIKeyGHOAQISTXDNQLM-LBTDBDNISA-N
Species of MetaboliteComponentSourceComments
Jacobaea (ncbitaxon:405757)
leaf (BTO:0000713) MetaboLights (MTBLS429)
leaf (BTO:0000713) DOI (10.1007/s11306-017-1184-0)
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
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)
dehydrojacoline (CHEBI:136495) has functional parent senecionine (CHEBI:9107)
dehydrojacoline (CHEBI:136495) has role Jacobaea metabolite (CHEBI:139566)
dehydrojacoline (CHEBI:136495) is a macrocyclic lactone (CHEBI:63944)
dehydrojacoline (CHEBI:136495) is a organic heterotricyclic compound (CHEBI:26979)
dehydrojacoline (CHEBI:136495) is a pyrrolizine alkaloid (CHEBI:38521)
dehydrojacoline (CHEBI:136495) is a tertiary amino compound (CHEBI:50996)
dehydrojacoline (CHEBI:136495) is a triol (CHEBI:27136)
IUPAC Name 
(3R,6R,14aR,14bR)-3,6-dihydroxy-3-[(1R)-1-hydroxyethyl]-6-methyl-5-methylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione
Citations