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CHEBI:66803 - obolactone

ChEBI IDCHEBI:66803
ChEBI Nameobolactone
Stars
DefinitionA pyranone isolated from the trunk barks of Cryptocarya obovata and has been shown to exhibit cytotoxicity against the KB cell line.
Last Modified11 May 2016
DownloadsMolfile
FormulaC19H18O4
Net Charge0
Average Mass310.349
Monoisotopic Mass310.12051
SMILES[H][C@@]1(C[C@H]2CC=CC(=O)O2)CC(=O)C=C(/C=C/c2ccccc2)O1
InChIInChI=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
InChIKeyNZGGCMIUTMKVIG-WADNSWHXSA-N
Species of MetaboliteComponentSourceComments
Cryptocarya obovata (ncbitaxon:29743)
trunk bark (BTO:0001494) PubMed (15165150)
fruit (BTO:0000486) PubMed (15165150)
Roles Classification
Biological Role:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
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-oneChEBI
Registry NumbersSources
Reaxys:10689895Reaxys
Citations