CHEBI:136452 - jacoline

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ChEBI Name jacoline
ChEBI ID CHEBI:136452
Definition A pyrrolizine alkaloid obtained from senecionine by formal addition of hydrogen peroxide across the ethylidene double bond.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C18H27NO7
Net Charge 0
Average Mass 369.410
Monoisotopic Mass 369.17875
InChI InChI=1S/C18H27NO7/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/h4,10-11,13-14,20,23-24H,5-9H2,1-3H3/t10-,11-,13-,14-,17-,18+/m1/s1
InChIKey FMWJEBGSMAOQNN-YLFNNMARSA-N
SMILES [C@@]1([C@@H](C)O)(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 (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 jacoline (CHEBI:136452) has functional parent senecionine (CHEBI:9107)
jacoline (CHEBI:136452) has role Jacobaea metabolite (CHEBI:139566)
jacoline (CHEBI:136452) is a macrocyclic lactone (CHEBI:63944)
jacoline (CHEBI:136452) is a organic heterotricyclic compound (CHEBI:26979)
jacoline (CHEBI:136452) is a pyrrolizine alkaloid (CHEBI:38521)
jacoline (CHEBI:136452) is a tertiary amino compound (CHEBI:50996)
jacoline (CHEBI:136452) is a triol (CHEBI:27136)
Incoming dehydrojaconine (CHEBI:136460) has functional parent jacoline (CHEBI:136452)
jacoline N-oxide (CHEBI:136454) has functional parent jacoline (CHEBI:136452)
jaconine (CHEBI:136455) has functional parent jacoline (CHEBI:136452)
IUPAC Name
(3S,5R,6R,14aR,14bR)-3,6-dihydroxy-3-[(1R)-1-hydroxyethyl]-5,6-dimethyl-3,4,5,6,9,11,13,14,14a,14b-decahydro[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione
Synonym Source
(15alpha,20R)-12,15,20-Trihydroxy-15,20-dihydrosenecionan-11,16-dione ChemIDplus
Manual Xref Database
C00026209 KNApSAcK
View more database links
Registry Numbers Types Sources
480-76-2 CAS Registry Number NIST Chemistry WebBook
480-76-2 CAS Registry Number ChemIDplus
56051 Reaxys Registry Number Reaxys
Last Modified
09 February 2018