CHEBI:136490 - florosenine

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ChEBI Name florosenine
ChEBI ID CHEBI:136490
Definition A pyrrolizine alkaloid that is otosenine in which the hydroxy hydrogen has been replaced by an acetyl group.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C21H29NO8
Net Charge 0
Average Mass 423.458
Monoisotopic Mass 423.18932
InChI InChI=1S/C21H29NO8/c1-12-10-21(13(2)29-21)19(26)28-16-7-9-22(5)8-6-15(17(16)24)11-27-18(25)20(12,4)30-14(3)23/h6,12-13,16H,7-11H2,1-5H3/b15-6-/t12-,13+,16-,20-,21+/m1/s1
InChIKey RNNVXCSFOWGBQP-DIOQTCHZSA-N
SMILES [C@@]12([C@H](C)O1)C(O[C@H]3C(C(=CCN(CC3)C)COC([C@@]([C@@H](C2)C)(OC(=O)C)C)=O)=O)=O
Metabolite of Species Details
Jacobaea gibbosa (NCBI:txid1211485) See: PubMed
Jacobaea ambigua (NCBI:txid189228) See: PubMed
Jacobaea ambigua subsp. nebrodensis (NCBI:txid248815) See: PubMed
Jacobaea (NCBI:txid405757) Found in leaf (BTO:0000713). See: MetaboLights Study
Jacobaea (NCBI:txid405757) Found in leaf (BTO:0000713). See: DOI
Senecio flaccidus var. douglasii (NCBI:txid98720) 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 florosenine (CHEBI:136490) has functional parent otosenine (CHEBI:136467)
florosenine (CHEBI:136490) has role Jacobaea metabolite (CHEBI:139566)
florosenine (CHEBI:136490) is a acetate ester (CHEBI:47622)
florosenine (CHEBI:136490) is a enone (CHEBI:51689)
florosenine (CHEBI:136490) is a macrocyclic lactone (CHEBI:63944)
florosenine (CHEBI:136490) is a organic heterobicyclic compound (CHEBI:27171)
florosenine (CHEBI:136490) is a pyrrolizine alkaloid (CHEBI:38521)
florosenine (CHEBI:136490) is a spiro-epoxide (CHEBI:133131)
florosenine (CHEBI:136490) is a tertiary amino compound (CHEBI:50996)
IUPAC Name
(1R,3'S,4S,6R,7R,11Z)-3',6,7,14-tetramethyl-3,8,17-trioxospiro[2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-ene-4,2'-oxiran]-7-yl acetate
Synonyms Sources
Acetylfukinotoxin ChemIDplus
acetylotosenine ChEBI
O-acetylotosenine ChEBI
Otosenine 12-acetate KNApSAcK
Manual Xrefs Databases
30772353 ChemSpider
C00026194 KNApSAcK
View more database links
Registry Numbers Types Sources
16958-30-8 CAS Registry Number ChemIDplus
16958-30-8 CAS Registry Number NIST Chemistry WebBook
5413520 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
17913058 PubMed citation Europe PMC
21819407 PubMed citation Europe PMC
3394160 PubMed citation Europe PMC
4005849 PubMed citation Europe PMC
8646334 PubMed citation Europe PMC
Last Modified
09 February 2018