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CHEBI:90272 - lactucin 15-oxalate

ChEBI IDCHEBI:90272
ChEBI Namelactucin 15-oxalate
Stars
DefinitionA sesquiterpene lactone obtained by formal condensation of one of the carboxy groups of oxalic acid with the 15-hydroxy group of lactucin. Found in chicory.
Last Modified15 June 2016
Submittermwilliams
DownloadsMolfile
FormulaC17H16O8
Net Charge0
Average Mass348.307
Monoisotopic Mass348.08452
SMILES[H][C@]12C(COC(=O)C(=O)O)=CC(=O)C1=C(C)C[C@H](O)[C@@]1([H])C(=C)C(=O)O[C@]21[H]
InChIInChI=1S/C17H16O8/c1-6-3-9(18)12-7(2)16(22)25-14(12)13-8(4-10(19)11(6)13)5-24-17(23)15(20)21/h4,9,12-14,18H,2-3,5H2,1H3,(H,20,21)/t9-,12+,13-,14-/m0/s1
InChIKeyLMOXWYJMYLUOMS-VZLIPTOUSA-N
Species of MetaboliteComponentSourceComments
Cichorium intybus (ncbitaxon:13427) - MetaboLights (MTBLS270)
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Role:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
ChEBI Ontology
Outgoing Relation(s)
lactucin 15-oxalate (CHEBI:90272) has functional parent lactucin (CHEBI:6358)
lactucin 15-oxalate (CHEBI:90272) has functional parent oxalic acid (CHEBI:16995)
lactucin 15-oxalate (CHEBI:90272) has role plant metabolite (CHEBI:76924)
lactucin 15-oxalate (CHEBI:90272) is a azulenofuran (CHEBI:39433)
lactucin 15-oxalate (CHEBI:90272) is a cyclic terpene ketone (CHEBI:36130)
lactucin 15-oxalate (CHEBI:90272) is a enone (CHEBI:51689)
lactucin 15-oxalate (CHEBI:90272) is a oxo monocarboxylic acid (CHEBI:35871)
lactucin 15-oxalate (CHEBI:90272) is a secondary alcohol (CHEBI:35681)
lactucin 15-oxalate (CHEBI:90272) is a sesquiterpene lactone (CHEBI:37667)
IUPAC Name 
{[(3aR,4S,9aS,9bR)-4-hydroxy-6-methyl-3-methylidene-2,7-dioxo-2,3,3a,4,5,7,9a,9b-octahydroazuleno[4,5-b]furan-9-yl]methoxy}(oxo)acetic acid
Manual XrefsDatabases
C00034017KNApSAcK
Registry NumbersSources
CAS:303130-76-9KNApSAcK