CHEBI:136495 - dehydrojacoline

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ChEBI Name dehydrojacoline
ChEBI ID CHEBI:136495
Definition A pyrrolizine alkaloid that is jacoline in which the 5-methyl group has been replaced by methylene.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C18H25NO7
Net Charge 0
Average Mass 367.394
Monoisotopic Mass 367.16310
InChI InChI=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
InChIKey GHOAQISTXDNQLM-LBTDBDNISA-N
SMILES [C@@]1([C@@H](C)O)(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:txidtxid405757) Found in leaf (BTO:0000713). See: DOI
Jacobaea (NCBI:txidtxid405757) Found in leaf (BTO:0000713). See: MetaboLights Study
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 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
Citation Waiting for Citations Type Source
28829252 PubMed citation Europe PMC
Last Modified
09 February 2018