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

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name 3,4-dihydroxy-5-prenylcinnamic acid
ChEBI ID CHEBI:65784
Definition A hydroxycinnamic acid that is trans-caffeic acid substituted by a prenyl group at position 5. Isolated from Brazilian propolis, it exhibits antioxidant activity.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C14H16O4
Net Charge 0
Average Mass 248.27440
Monoisotopic Mass 248.10486
InChI InChI=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+
InChIKey JVQIELYQOZIVPK-GQCTYLIASA-N
SMILES CC(C)=CCc1cc(cc(O)c1O)\C=C\C(O)=O
Metabolite of Species Details
Brazilian propolis See: DOI
Roles Classification
Chemical Role(s): 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 (Bronsted base).
(via oxoacid )
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Number Type Source
8495042 Reaxys Registry Number Reaxys
Last Modified
22 February 2013
General Comment
2013-01-11 Chem. Pharm. Bull., 1999, 47, 1521-24.