cis-caffeic acid (CHEBI:17395)

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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

Average Mass

180.15740

Monoisotopic Mass

180.04226

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 )

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

Last Modified

10 January 2019