CHEBI:131631 - biliatresone

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ChEBI Name biliatresone
ChEBI ID CHEBI:131631
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C18H16O6
Net Charge 0
Average Mass 328.317
Monoisotopic Mass 328.09469
InChI InChI=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
InChIKey SIKIIXNKUAAGAM-UHFFFAOYSA-N
SMILES C1(=CC2=C(C(=C1C(=O)C(=C)C=3C=CC=CC3O)OC)OCO2)OC
Metabolite of Species Details
Dysphania glomulifera (NCBI:txid240059) See: PubMed
Roles Classification
Biological Role(s): 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.
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ChEBI Ontology
Outgoing 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-methylenedioxybenzene ChEBI
Manual Xref Database
Biliatresone Wikipedia
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Citations Waiting for Citations Types Sources
25947162 PubMed citation Europe PMC
26008130 PubMed citation Europe PMC
26175131 PubMed citation Europe PMC
26653951 PubMed citation Europe PMC
26713899 PubMed citation Europe PMC
Last Modified
04 January 2017