EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:90275 - lactucopicrin

Default Structure
ChEBI IDCHEBI:90275
ChEBI Namelactucopicrin
Stars
DefinitionA sesquiterpene lactone obtained by formal condensation of the carboxy group of 4-hydroxyphenylacetic acid with the 8-hydroxy group of lactucin. Found in chicory.
Last Modified16 June 2016
Submittermwilliams
DownloadsMolfile
FormulaC23H22O7
Net Charge0
Average Mass410.422
Monoisotopic Mass410.13655
SMILES[H][C@]12C(CO)=CC(=O)C1=C(C)C[C@H](OC(=O)Cc1ccc(O)cc1)[C@@]1([H])C(=C)C(=O)O[C@]21[H]
InChIInChI=1S/C23H22O7/c1-11-7-17(29-18(27)8-13-3-5-15(25)6-4-13)20-12(2)23(28)30-22(20)21-14(10-24)9-16(26)19(11)21/h3-6,9,17,20-22,24-25H,2,7-8,10H2,1H3/t17-,20+,21-,22-/m0/s1
InChIKeyUMVSOHBRAQTGQI-XGARDCMYSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Cichorium intybus (ncbitaxon:13427) - MetaboLights (MTBLS270)
Roles Classification
Biological Roles:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
antimalarial  A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
Applications:
sedative  A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.
antimalarial  A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
ChEBI Ontology
Outgoing Relation(s)
lactucopicrin (CHEBI:90275) has functional parent 4-hydroxyphenylacetic acid (CHEBI:18101)
lactucopicrin (CHEBI:90275) has functional parent lactucin (CHEBI:6358)
lactucopicrin (CHEBI:90275) has role antimalarial (CHEBI:38068)
lactucopicrin (CHEBI:90275) has role plant metabolite (CHEBI:76924)
lactucopicrin (CHEBI:90275) has role sedative (CHEBI:35717)
lactucopicrin (CHEBI:90275) is a azulenofuran (CHEBI:39433)
lactucopicrin (CHEBI:90275) is a cyclic terpene ketone (CHEBI:36130)
lactucopicrin (CHEBI:90275) is a enone (CHEBI:51689)
lactucopicrin (CHEBI:90275) is a phenols (CHEBI:33853)
lactucopicrin (CHEBI:90275) is a primary alcohol (CHEBI:15734)
lactucopicrin (CHEBI:90275) is a sesquiterpene lactone (CHEBI:37667)
IUPAC Name 
(3aR,4S,9aS,9bR)-9-(hydroxymethyl)-6-methyl-3-methylidene-2,7-dioxo-2,3,3a,4,5,7,9a,9b-octahydroazuleno[4,5-b]furan-4-yl (4-hydroxyphenyl)acetate
Synonyms  Source
LactopicrinChemIDplus
(+)-LactucopicrinKNApSAcK
LactupicrinKNApSAcK
Manual XrefsDatabases
C00003312KNApSAcK
HMDB0035828HMDB
LactucopicrinWikipedia
Registry NumbersSources
Reaxys:1358541Reaxys
CAS:65725-11-3ChemIDplus
CAS:65725-11-3KNApSAcK
Citations