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CHEBI:66172 - sappanchalcone

ChEBI IDCHEBI:66172
ChEBI Namesappanchalcone
Stars
DefinitionA member of the class of chalcones that consists of trans-chalcone substituted by hydroxy groups at positions 3, 4 and 4' and a methoxy group at position 2'. Isolated from Caesalpinia sappan, it exhibits neuroprotective and cytoprotective activity.
Last Modified25 April 2013
DownloadsMolfile
FormulaC16H14O5
Net Charge0
Average Mass286.283
Monoisotopic Mass286.08412
SMILESCOc1cc(O)ccc1C(=O)/C=C/c1ccc(O)c(O)c1
InChIInChI=1S/C16H14O5/c1-21-16-9-11(17)4-5-12(16)13(18)6-2-10-3-7-14(19)15(20)8-10/h2-9,17,19-20H,1H3/b6-2+
InChIKeyJVGNTXGHBHMJDO-QHHAFSJGSA-N
Species of MetaboliteComponentSourceComments
Caesalpinia sappan (ncbitaxon:483143) heartwood (PO:0004512) PubMed (19420770)
Roles Classification
Chemical Role:
antioxidant  A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Role:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Applications:
anti-allergic agent  A drug used to treat allergic reactions.
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
ChEBI Ontology
Outgoing Relation(s)
sappanchalcone (CHEBI:66172) has functional parent trans-chalcone (CHEBI:48965)
sappanchalcone (CHEBI:66172) has role anti-allergic agent (CHEBI:50857)
sappanchalcone (CHEBI:66172) has role anti-inflammatory agent (CHEBI:67079)
sappanchalcone (CHEBI:66172) has role antioxidant (CHEBI:22586)
sappanchalcone (CHEBI:66172) has role metabolite (CHEBI:25212)
sappanchalcone (CHEBI:66172) is a catechols (CHEBI:33566)
sappanchalcone (CHEBI:66172) is a chalcones (CHEBI:23086)
sappanchalcone (CHEBI:66172) is a monomethoxybenzene (CHEBI:25235)
IUPAC Name 
(2E)-3-(3,4-dihydroxyphenyl)-1-(4-hydroxy-2-methoxyphenyl)prop-2-en-1-one
Synonym  Source
3,4,4'-trihydroxy-2'-methoxychalconeChEBI
Manual XrefsDatabases
KR20120007809Patent
KR20070060715Patent
WO2007066928Patent
LMPK12120114LIPID MAPS
Registry NumbersSources
Reaxys:5968372Reaxys
CAS:94344-54-4ChemIDplus
Citations