CHEBI:136458 - jacozine

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ChEBI Name jacozine
ChEBI ID CHEBI:136458
Definition A pyrrolizine alkaloid that is seneciphylline in which the exocyclic double bond has been converted to the corresponding epoxide.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C18H23NO6
Net Charge 0
Average Mass 349.379
Monoisotopic Mass 349.15254
InChI InChI=1S/C18H23NO6/c1-10-8-18(11(2)25-18)16(21)24-13-5-7-19-6-4-12(14(13)19)9-23-15(20)17(10,3)22/h4,11,13-14,22H,1,5-9H2,2-3H3/t11-,13+,14+,17+,18-/m0/s1
InChIKey XCEPKQNOWNOSFH-CGPXFRKCSA-N
SMILES [C@@]12([C@H](C)O1)C(O[C@H]3[C@@]4(N(CC=C4COC([C@](C(C2)=C)(C)O)=O)CC3)[H])=O
Metabolite of Species Details
Jacobaea ambigua (NCBI:txid189228) See: PubMed
Senecio aquaticus (NCBI:txid189230) See: PubMed
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 jacozine (CHEBI:136458) has functional parent seneciphylline (CHEBI:9108)
jacozine (CHEBI:136458) has role Jacobaea metabolite (CHEBI:139566)
jacozine (CHEBI:136458) is a macrocyclic lactone (CHEBI:63944)
jacozine (CHEBI:136458) is a organic heterotricyclic compound (CHEBI:26979)
jacozine (CHEBI:136458) is a pyrrolizine alkaloid (CHEBI:38521)
jacozine (CHEBI:136458) is a spiro-epoxide (CHEBI:133131)
jacozine (CHEBI:136458) is a tertiary alcohol (CHEBI:26878)
jacozine (CHEBI:136458) is a tertiary amino compound (CHEBI:50996)
Incoming jacozine N-oxide (CHEBI:136459) has functional parent jacozine (CHEBI:136458)
IUPAC Name
(3S,3'S,6R,14aR,14bR)-6-hydroxy-3',6-dimethyl-5-methylidene-5,6,9,11,13,14,14a,14b-octahydro-2H-spiro[1,6-dioxacyclododecino[2,3,4-gh]pyrrolizine-3,2'-oxirane]-2,7(4H)-dione
Synonyms Sources
12-hydroxy-13,19-didehydro-15,20-dihydro-15,20-epoxysenecionan-11,16-dione ChEBI
13,19-didehydrojacobine ChEBI
Manual Xref Database
455001 ChemSpider
View more database links
Registry Numbers Types Sources
5532-23-0 CAS Registry Number NIST Chemistry WebBook
5532-23-0 CAS Registry Number ChemIDplus
56906 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11978435 PubMed citation Europe PMC
17913058 PubMed citation Europe PMC
21159354 PubMed citation Europe PMC
6836586 PubMed citation Europe PMC
835011 PubMed citation Europe PMC
8572933 PubMed citation Europe PMC
9328525 PubMed citation Europe PMC
IND44598050 Agricola citation Europe PMC
Last Modified
09 February 2018