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CHEBI:65784 - 3,4-dihydroxy-5-prenylcinnamic acid

ChEBI IDCHEBI:65784
ChEBI Name3,4-dihydroxy-5-prenylcinnamic acid
Stars
DefinitionA hydroxycinnamic acid that is trans-caffeic acid substituted by a prenyl group at position 5. Isolated from Brazilian propolis, it exhibits antioxidant activity.
Last Modified22 February 2013
DownloadsMolfile
FormulaC14H16O4
Net Charge0
Average Mass248.278
Monoisotopic Mass248.10486
SMILESCC(C)=CCc1cc(/C=C/C(=O)O)cc(O)c1O
InChIInChI=1S/C14H16O4/c1-9(2)3-5-11-7-10(4-6-13(16)17)8-12(15)14(11)18/h3-4,6-8,15,18H,5H2,1-2H3,(H,16,17)/b6-4+
InChIKeyJVQIELYQOZIVPK-GQCTYLIASA-N
Species of MetaboliteComponentSourceComments
Brazilian propolis- DOI (10.1248/cpb.47.1521)
Roles Classification
Chemical Roles:
antioxidant  A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Role:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
3,4-dihydroxy-5-prenylcinnamic acid (CHEBI:65784) has functional parent trans-caffeic acid (CHEBI:16433)
3,4-dihydroxy-5-prenylcinnamic acid (CHEBI:65784) has role antioxidant (CHEBI:22586)
3,4-dihydroxy-5-prenylcinnamic acid (CHEBI:65784) has role metabolite (CHEBI:25212)
3,4-dihydroxy-5-prenylcinnamic acid (CHEBI:65784) is a hydroxycinnamic acid (CHEBI:24689)
IUPAC Name 
(2E)-3-[3,4-dihydroxy-5-(3-methylbut-2-en-1-yl)phenyl]prop-2-enoic acid
Registry NumbersSources
Reaxys:8495042Reaxys