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CHEBI:131631 - biliatresone

ChEBI IDCHEBI:131631
ChEBI Namebiliatresone
Stars
DefinitionA member of the class of benzodioxoles that is 1,3-benzodioxole which is substituted at positions 5 by a 2-(2-hydroxyphenyl)-3-oxoprop-1-en-3-yl group and at positions 4 and 6 by methoxy groups. A very rare type of isoflavonoid-related 1,2-diaryl-2-propenone found in Dysphania glomulifera (red crumbweed) and D. littoralis, the enone moiety is particularly reactive, undergoing ready Michael addition of water and methanol. Biliatresone has been found to cause extrahepatic biliary atresia (obliteration or discontinuity of the extrahepatic biliary system, resulting in obstruction to bile flow) in a zebrafish model.
Last Modified4 January 2017
SubmitterGareth Owen
DownloadsMolfile
FormulaC18H16O6
Net Charge0
Average Mass328.320
Monoisotopic Mass328.09469
SMILESC=C(C(=O)c1c(OC)cc2c(c1OC)OCO2)c1ccccc1O
InChIInChI=1S/C18H16O6/c1-10(11-6-4-5-7-12(11)19)16(20)15-13(21-2)8-14-17(18(15)22-3)24-9-23-14/h4-8,19H,1,9H2,2-3H3
InChIKeySIKIIXNKUAAGAM-UHFFFAOYSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Dysphania glomulifera (ncbitaxon:240059) - PubMed (26175131)
Roles Classification
Biological Roles:
toxin  Poisonous substance produced by a biological organism such as a microbe, animal or plant.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
ChEBI Ontology
Outgoing Relation(s)
biliatresone (CHEBI:131631) has role plant metabolite (CHEBI:76924)
biliatresone (CHEBI:131631) has role toxin (CHEBI:27026)
biliatresone (CHEBI:131631) is a aromatic ether (CHEBI:35618)
biliatresone (CHEBI:131631) is a aromatic ketone (CHEBI:76224)
biliatresone (CHEBI:131631) is a benzodioxoles (CHEBI:38298)
biliatresone (CHEBI:131631) is a enone (CHEBI:51689)
biliatresone (CHEBI:131631) is a phenols (CHEBI:33853)
IUPAC Name 
1-(4,6-dimethoxy-1,3-benzodioxol-5-yl)-2-(2-hydroxyphenyl)prop-2-en-1-one
Synonym  Source
2-[2-(2-hydroxyphenyl)-3-oxoprop-1-en-3-yl]-1,3-dimethoxy-4,5-methylenedioxybenzeneChEBI
Manual XrefsDatabases
BiliatresoneWikipedia
Citations