CHEBI:90275 - lactucopicrin

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ChEBI Name lactucopicrin
ChEBI ID CHEBI:90275
Definition A sesquiterpene lactone obtained by formal condensation of the carboxy group of 4-hydroxyphenylacetic acid with the 8-hydroxy group of lactucin. Found in chicory.
Stars This entity has been manually annotated by a third party.
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Formula C23H22O7
Net Charge 0
Average Mass 410.417
Monoisotopic Mass 410.13655
InChI InChI=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
InChIKey UMVSOHBRAQTGQI-XGARDCMYSA-N
SMILES OCC1=CC(=O)C2=C(C)C[C@@H]([C@]3(C(=C)C(=O)O[C@@]3([C@@]12[H])[H])[H])OC(=O)CC=4C=CC(O)=CC4
Metabolite of Species Details
Cichorium intybus (NCBI:txid13427) See: MetaboLights Study
Roles Classification
Biological Role(s): 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.
Application(s): 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.
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ChEBI Ontology
Outgoing 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 Sources
(+)-Lactucopicrin KNApSAcK
Lactopicrin ChemIDplus
Lactupicrin KNApSAcK
Manual Xrefs Databases
C00003312 KNApSAcK
HMDB0035828 HMDB
Lactucopicrin Wikipedia
View more database links
Registry Numbers Types Sources
1358541 Reaxys Registry Number Reaxys
65725-11-3 CAS Registry Number ChemIDplus
65725-11-3 CAS Registry Number KNApSAcK
Citations Waiting for Citations Types Sources
10858433 PubMed citation Europe PMC
15507374 PubMed citation Europe PMC
16621374 PubMed citation Europe PMC
Last Modified
16 June 2016