CHEBI:66803 - obolactone

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ChEBI Name obolactone
ChEBI ID CHEBI:66803
Definition A pyranone isolated from the trunk barks of Cryptocarya obovata and has been shown to exhibit cytotoxicity against the KB cell line.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C19H18O4
Net Charge 0
Average Mass 310.345
Monoisotopic Mass 310.12051
InChI InChI=1S/C19H18O4/c20-15-11-17(10-9-14-5-2-1-3-6-14)22-18(12-15)13-16-7-4-8-19(21)23-16/h1-6,8-11,16,18H,7,12-13H2/b10-9+/t16-,18+/m1/s1
InChIKey NZGGCMIUTMKVIG-WADNSWHXSA-N
SMILES C1=CC=CC(/C=C/C2=CC(C[C@](O2)(C[C@H]3CC=CC(O3)=O)[H])=O)=C1
Metabolite of Species Details
Cryptocarya obovata (NCBI:txid29743) Found in trunk bark (BTO:0001494). See: PubMed
Cryptocarya obovata (NCBI:txid29743) Found in fruit (BTO:0000486). See: PubMed
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.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing obolactone (CHEBI:66803) has role antineoplastic agent (CHEBI:35610)
obolactone (CHEBI:66803) has role plant metabolite (CHEBI:76924)
obolactone (CHEBI:66803) is a 2-pyranones (CHEBI:75885)
obolactone (CHEBI:66803) is a 4-pyranones (CHEBI:131906)
IUPAC Name
(6R)-6-({(2R)-4-oxo-6-[(E)-2-phenylethenyl]-3,4-dihydro-2H-pyran-2-yl}methyl)-5,6-dihydro-2H-pyran-2-one
Synonym Source
(2R)-2-[[(2R)-6-oxo-2,3-dihydropyran-2-yl]methyl]-6-[(E)-2-phenylethenyl]-2,3-dihydropyran-4-one ChEBI
Registry Number Type Source
10689895 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
15165150 PubMed citation Europe PMC
16555857 PubMed citation Europe PMC
23451721 PubMed citation Europe PMC
Last Modified
11 May 2016