CHEBI:17395 - cis-caffeic acid

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ChEBI Name cis-caffeic acid
ChEBI ID CHEBI:17395
ChEBI ASCII Name cis-caffeic acid
Definition The cis-isomer of caffeic acid.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:36089, CHEBI:13929, CHEBI:3292, CHEBI:19880, CHEBI:22979, CHEBI:19881
Supplier Information
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Formula C9H8O4
Net Charge 0
Average Mass 180.15740
Monoisotopic Mass 180.042
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)/b4-2-
InChIKey QAIPRVGONGVQAS-RQOWECAXSA-N
SMILES OC(=O)\C=C/c1ccc(O)c(O)c1
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
(via caffeic acid )
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.
(via caffeic acid )
human xenobiotic metabolite
Any human metabolite produced by metabolism of a xenobiotic compound in humans.
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).
(via caffeic acid )
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).
(via caffeic acid )
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).
(via caffeic acid )
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).
(via caffeic acid )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing cis-caffeic acid (CHEBI:17395) has role human xenobiotic metabolite (CHEBI:76967)
cis-caffeic acid (CHEBI:17395) has role plant metabolite (CHEBI:76924)
cis-caffeic acid (CHEBI:17395) is a caffeic acid (CHEBI:36281)
cis-caffeic acid (CHEBI:17395) is conjugate acid of cis-caffeate (CHEBI:58129)
Incoming (2S,3R)-cis-caftaric acid (CHEBI:76082) has functional parent cis-caffeic acid (CHEBI:17395)
3-(Z)-caffeoyllupeol (CHEBI:65549) has functional parent cis-caffeic acid (CHEBI:17395)
5-O-cis-caffeoylquinic acid (CHEBI:75489) has functional parent cis-caffeic acid (CHEBI:17395)
malvidin 3-O-{6-O-[(Z)-caffeoyl]-β-D-glucoside} (CHEBI:131452) has functional parent cis-caffeic acid (CHEBI:17395)
cis-caffeate (CHEBI:58129) is conjugate base of cis-caffeic acid (CHEBI:17395)
IUPAC Name
(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
Synonyms Sources
3,4-Dihydroxycinnamic acid KEGG COMPOUND
Caffeate KEGG COMPOUND
Caffeic acid KEGG COMPOUND
cis-Caffeic acid KEGG COMPOUND
cis-caffeic acid UniProt
Database Links Databases
C01481 KEGG COMPOUND
CPD-8098 MetaCyc
DB01880 DrugBank
HMDB0001964 HMDB
View more database links
Registry Numbers Types Sources
2210884 Reaxys Registry Number Reaxys
331-39-5 CAS Registry Number KEGG COMPOUND
331-39-5 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
19812218 PubMed citation Europe PMC
19952409 PubMed citation Europe PMC
24088646 PubMed citation Europe PMC
24138287 PubMed citation Europe PMC
24206679 PubMed citation Europe PMC
Last Modified
10 November 2016