CHEBI:136455 - jaconine

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ChEBI Name jaconine
Definition A pyrrolizine alkaloid that is jacoline in which the secondary hydroxy group has been replaced by a chlorine.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C18H26ClNO6
Net Charge 0
Average Mass 387.856
Monoisotopic Mass 387.14487
InChI InChI=1S/C18H26ClNO6/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/h4,10-11,13-14,23-24H,5-9H2,1-3H3/t10-,11-,13-,14-,17-,18+/m1/s1
SMILES [C@@]1([C@@H](C)Cl)(O)C(O[C@H]2[C@@]3(N(CC=C3COC([C@]([C@@H](C1)C)(C)O)=O)CC2)[H])=O
Metabolite of Species Details
Jacobaea aquatica (NCBI:txid189230) See: PubMed
Jacobaea cannabifolia var. integrifolia (NCBI:txid189233) See: PubMed
Senecio bicolor subsp. cineraria (NCBI:txid252537) See: PubMed
Jacobaea (NCBI:txid405757) Found in leaf (BTO:0000713). See: MetaboLights Study
Jacobaea (NCBI:txid405757) Found in leaf (BTO:0000713). See: DOI
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.
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 jaconine (CHEBI:136455) has functional parent jacoline (CHEBI:136452)
jaconine (CHEBI:136455) has role Jacobaea metabolite (CHEBI:139566)
jaconine (CHEBI:136455) is a diol (CHEBI:23824)
jaconine (CHEBI:136455) is a macrocyclic lactone (CHEBI:63944)
jaconine (CHEBI:136455) is a organic heterotricyclic compound (CHEBI:26979)
jaconine (CHEBI:136455) is a organochlorine compound (CHEBI:36683)
jaconine (CHEBI:136455) is a pyrrolizine alkaloid (CHEBI:38521)
jaconine (CHEBI:136455) is a tertiary amino compound (CHEBI:50996)
Incoming jaconine N-oxide (CHEBI:136457) has functional parent jaconine (CHEBI:136455)
Synonym Source
(15alpha,20R)-20-Chloro-15,20-dihydro-12,15-dihydroxysenecionan-11,16-dione ChemIDplus
Manual Xref Database
106487 ChemSpider
View more database links
Registry Numbers Types Sources
480-75-1 CAS Registry Number ChemIDplus
480-75-1 CAS Registry Number NIST Chemistry WebBook
56049 Beilstein Registry Number ChemIDplus
56049 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
16826978 PubMed citation Europe PMC
17913058 PubMed citation Europe PMC
19169751 PubMed citation Europe PMC
21159354 PubMed citation Europe PMC
21506416 PubMed citation Europe PMC
21969251 PubMed citation Europe PMC
22516740 PubMed citation Europe PMC
835011 PubMed citation Europe PMC
9328525 PubMed citation Europe PMC
IND44598050 Agricola citation Europe PMC
Last Modified
08 February 2018