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CHEBI:136460 - dehydrojaconine

ChEBI IDCHEBI:136460
ChEBI Namedehydrojaconine
Stars
DefinitionA pyrrolizine alkaloid that is jacoline in which the secondary hydroxy group has been replaced by a chlorine and the 5-methyl group has been replaced by methylene.
Last Modified9 February 2018
SubmitterKeeva
DownloadsMolfile
FormulaC18H24ClNO6
Net Charge0
Average Mass385.844
Monoisotopic Mass385.12922
SMILES[H][C@]12C3=CCN1CC[C@H]2OC(=O)[C@@](O)([C@@H](C)Cl)CC(=C)[C@@](C)(O)C(=O)OC3
InChIInChI=1S/C18H24ClNO6/c1-10-8-18(24,11(2)19)16(22)26-13-5-7-20-6-4-12(14(13)20)9-25-15(21)17(10,3)23/h4,11,13-14,23-24H,1,5-9H2,2-3H3/t11-,13-,14-,17-,18+/m1/s1
InChIKeyNAORWVQLZFUIRD-LBTDBDNISA-N
Species of MetaboliteComponentSourceComments
Jacobaea (ncbitaxon:405757)
leaf (BTO:0000713) MetaboLights (MTBLS429)
leaf (BTO:0000713) DOI (10.1007/s11306-017-1184-0)
Jacobaea vulgaris (ncbitaxon:98722) - PubMed (21159354)
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)
dehydrojaconine (CHEBI:136460) has functional parent jacoline (CHEBI:136452)
dehydrojaconine (CHEBI:136460) has role Jacobaea metabolite (CHEBI:139566)
dehydrojaconine (CHEBI:136460) is a diol (CHEBI:23824)
dehydrojaconine (CHEBI:136460) is a macrocyclic lactone (CHEBI:63944)
dehydrojaconine (CHEBI:136460) is a organic heterotricyclic compound (CHEBI:26979)
dehydrojaconine (CHEBI:136460) is a organochlorine compound (CHEBI:36683)
dehydrojaconine (CHEBI:136460) is a pyrrolizine alkaloid (CHEBI:38521)
dehydrojaconine (CHEBI:136460) is a tertiary amino compound (CHEBI:50996)
IUPAC Name 
(3R,6R,14aR,14bR)-3-[(1R)-1-chloroethyl]-3,6-dihydroxy-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