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CHEBI:136490 - florosenine

ChEBI IDCHEBI:136490
ChEBI Nameflorosenine
Stars
DefinitionA pyrrolizine alkaloid that is otosenine in which the hydroxy hydrogen has been replaced by an acetyl group.
Last Modified9 February 2018
SubmitterKeeva
DownloadsMolfile
FormulaC21H29NO8
Net Charge0
Average Mass423.462
Monoisotopic Mass423.18932
SMILESCC(=O)O[C@@]1(C)C(=O)OC/C2=C/CN(C)CC[C@@H](OC(=O)[C@@]3(C[C@H]1C)O[C@H]3C)C2=O
InChIInChI=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
InChIKeyRNNVXCSFOWGBQP-DIOQTCHZSA-N
Species of MetaboliteComponentSourceComments
Jacobaea (ncbitaxon:405757)
leaf (BTO:0000713) MetaboLights (MTBLS429)
leaf (BTO:0000713) DOI (10.1007/s11306-017-1184-0)
Jacobaea gibbosa (ncbitaxon:1211485) - PubMed (17913058)
Jacobaea ambigua (ncbitaxon:189228) - PubMed (17913058)
Senecio flaccidus var. douglasii (ncbitaxon:98720) - PubMed (8646334)
Jacobaea ambigua subsp. nebrodensis (ncbitaxon:248815) - PubMed (17913058)
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
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.
ChEBI Ontology
Outgoing Relation(s)
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  Source
acetylotosenineChEBI
O-acetylotosenineChEBI
Otosenine 12-acetateKNApSAcK
AcetylfukinotoxinChemIDplus
Manual XrefsDatabases
30772353ChemSpider
C00026194KNApSAcK
Registry NumbersSources
Reaxys:5413520Reaxys
CAS:16958-30-8ChemIDplus
CAS:16958-30-8NIST Chemistry WebBook
Citations