CHEBI:6358 - lactucin

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ChEBI Name lactucin
ChEBI ID CHEBI:6358
Definition An azulenofuran that is 3-methylidene-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-2,7-dione carrying additional hydroxy, methyl and hydroxymethyl substituents at positions 4, 6 and 9 respectively (the 3aR,4S,9aS,9bR-diastereomer). Found in chicory.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C15H16O5
Net Charge 0
Average Mass 276.285
Monoisotopic Mass 276.09977
InChI InChI=1S/C15H16O5/c1-6-3-9(17)12-7(2)15(19)20-14(12)13-8(5-16)4-10(18)11(6)13/h4,9,12-14,16-17H,2-3,5H2,1H3/t9-,12+,13-,14-/m0/s1
InChIKey VJQAFLAZRVKAKM-VZLIPTOUSA-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])O
Metabolite of Species Details
Cichorium intybus (NCBI:txid13427) See: MetaboLights Study
Roles Classification
Biological Role(s): 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.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application(s): 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.
sedative
A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.
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ChEBI Ontology
Outgoing lactucin (CHEBI:6358) has role antimalarial (CHEBI:38068)
lactucin (CHEBI:6358) has role plant metabolite (CHEBI:76924)
lactucin (CHEBI:6358) has role sedative (CHEBI:35717)
lactucin (CHEBI:6358) is a azulenofuran (CHEBI:39433)
lactucin (CHEBI:6358) is a cyclic terpene ketone (CHEBI:36130)
lactucin (CHEBI:6358) is a enone (CHEBI:51689)
lactucin (CHEBI:6358) is a primary alcohol (CHEBI:15734)
lactucin (CHEBI:6358) is a secondary alcohol (CHEBI:35681)
lactucin (CHEBI:6358) is a sesquiterpene lactone (CHEBI:37667)
Incoming 11β,13-dihydro-8-deoxylactucin (CHEBI:90279) has functional parent lactucin (CHEBI:6358)
11β,13-dihydrolactucin (CHEBI:90267) has functional parent lactucin (CHEBI:6358)
11β,13-dihydrolactucin 15-glycoside (CHEBI:90268) has functional parent lactucin (CHEBI:6358)
11β,13-dihydrolactucin 15-oxalate (CHEBI:90270) has functional parent lactucin (CHEBI:6358)
11β,13-dihydrolactucopicrin (CHEBI:90283) has functional parent lactucin (CHEBI:6358)
11β,13-dihydrolactucopicrin 15-oxalate (CHEBI:90281) has functional parent lactucin (CHEBI:6358)
11,13-dihydro-8-deoxylactucin 15-glycoside (CHEBI:90274) has functional parent lactucin (CHEBI:6358)
8-deoxylactucin-15-glycoside (CHEBI:90273) has functional parent lactucin (CHEBI:6358)
lactucin 15-glycoside (CHEBI:90271) has functional parent lactucin (CHEBI:6358)
lactucin 15-oxalate (CHEBI:90272) has functional parent lactucin (CHEBI:6358)
lactucopicrin (CHEBI:90275) has functional parent lactucin (CHEBI:6358)
lactucopicrin 15-oxalate (CHEBI:90280) has functional parent lactucin (CHEBI:6358)
IUPAC Name
(3aR,4S,9aS,9bR)-4-hydroxy-9-(hydroxymethyl)-6-methyl-3-methylidene-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-2,7-dione
Synonym Source
Lactucine ChemIDplus
Manual Xrefs Databases
C00003311 KNApSAcK
C09489 KEGG COMPOUND
HMDB0035814 HMDB
Lactucin Wikipedia
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Registry Numbers Types Sources
1891-29-8 CAS Registry Number ChemIDplus
40523 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
10858433 PubMed citation Europe PMC
15507374 PubMed citation Europe PMC
16621374 PubMed citation Europe PMC
24176340 PubMed citation Europe PMC
24333270 PubMed citation Europe PMC
IND601214396 Agricola citation Europe PMC
Last Modified
16 June 2016