CHEBI:36281 - caffeic acid

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ChEBI Name caffeic acid
ChEBI ID CHEBI:36281
Definition A hydroxycinnamic acid that is cinnamic acid in which the phenyl ring is substituted by hydroxy groups at positions 3 and 4. It exists in cis and trans forms; the latter is the more common.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C9H8O4
Net Charge 0
Average Mass 180.15740
InChI InChI=1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)
InChIKey QAIPRVGONGVQAS-UHFFFAOYSA-N
SMILES OC(=O)C=Cc1ccc(O)c(O)c1
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor
A lipoxygenase inhibitor that interferes with the action of arachidonate 15-lipoxygenase (EC 1.13.11.33).
EC 2.5.1.18 (glutathione transferase) inhibitor
An EC 2.5.1.* (non-methyl-alkyl or aryl transferase) inhibitor that interferes with the action of a glutathione transferase (EC 2.5.1.18).
EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor
A lipoxygenase inhibitor that interferes with the action of arachidonate 5-lipoxygenase (EC 1.13.11.34).
EC 3.5.1.98 (histone deacetylase) inhibitor
An EC 3.5.1.* (non-peptide linear amide C-N hydrolase) inhibitor that interferes with the function of histone deacetylase (EC 3.5.1.98).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing caffeic acid (CHEBI:36281) has role antioxidant (CHEBI:22586)
caffeic acid (CHEBI:36281) has role EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor (CHEBI:64996)
caffeic acid (CHEBI:36281) has role EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor (CHEBI:64964)
caffeic acid (CHEBI:36281) has role EC 2.5.1.18 (glutathione transferase) inhibitor (CHEBI:76797)
caffeic acid (CHEBI:36281) has role EC 3.5.1.98 (histone deacetylase) inhibitor (CHEBI:61115)
caffeic acid (CHEBI:36281) has role plant metabolite (CHEBI:76924)
caffeic acid (CHEBI:36281) is a catechols (CHEBI:33566)
caffeic acid (CHEBI:36281) is a hydroxycinnamic acid (CHEBI:24689)
Incoming alkyl caffeate ester (CHEBI:65331) has functional parent caffeic acid (CHEBI:36281)
caffeoyl-CoA (CHEBI:15518) has functional parent caffeic acid (CHEBI:36281)
cis-caffeic acid (CHEBI:17395) is a caffeic acid (CHEBI:36281)
trans-caffeic acid (CHEBI:16433) is a caffeic acid (CHEBI:36281)
IUPAC Name
3-(3,4-dihydroxyphenyl)prop-2-enoic acid
Database Links Databases
C01481 KEGG COMPOUND
HMDB01964 HMDB
LSM-5272 LINCS
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Registry Numbers Types Sources
2210883 Reaxys Registry Number Reaxys
2210883 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
11373473 PubMed citation CiteXplore
15778121 PubMed citation CiteXplore
18061431 PubMed citation CiteXplore
18314336 PubMed citation CiteXplore
18482095 PubMed citation CiteXplore
20542693 PubMed citation CiteXplore
8340025 PubMed citation CiteXplore
Last Modified
25 February 2016