CHEBI:136460 - dehydrojaconine

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ChEBI Name dehydrojaconine
ChEBI ID CHEBI:136460
Definition A pyrrolizine alkaloid that is jacoline in which the secondary hydroxy group has been replaced by a chlorine and the 5-methyl group has been replaced by methylene.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C18H24ClNO6
Net Charge 0
Average Mass 385.840
Monoisotopic Mass 385.12922
InChI InChI=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
InChIKey NAORWVQLZFUIRD-LBTDBDNISA-N
SMILES [C@@]1([C@@H](C)Cl)(O)C(O[C@H]2[C@@]3(N(CC=C3COC([C@](C(C1)=C)(C)O)=O)CC2)[H])=O
Metabolite of Species Details
Jacobaea (NCBI:txid405757) Found in leaf (BTO:0000713). See: DOI
Jacobaea (NCBI:txid405757) Found in leaf (BTO:0000713). See: MetaboLights Study
Jacobaea vulgaris (NCBI:txid98722) See: PubMed
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): 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.
(via alkaloid )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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
Citation Waiting for Citations Type Source
21159354 PubMed citation Europe PMC
Last Modified
09 February 2018