CHEBI:16433 - trans-caffeic acid

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ChEBI Name trans-caffeic acid
ChEBI ID CHEBI:16433
ChEBI ASCII Name trans-caffeic acid
Definition The trans-isomer of caffeic acid.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:12870, CHEBI:41964, CHEBI:1379, CHEBI:11691, CHEBI:11692, CHEBI:19877
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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-DUXPYHPUSA-N
SMILES OC(=O)\C=C\c1ccc(O)c(O)c1
Metabolite of Species Details
Solanum campaniforme (IPNI:818569-1) Found in leaf (BTO:0000713). Dried leaves were extracted with ethyl alcohol. See: PubMed
Mus musculus (NCBI:10090) Source: BioModels - MODEL1507180067 See: PubMed
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): mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
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 )
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 trans-caffeic acid (CHEBI:16433) has role mouse metabolite (CHEBI:75771)
trans-caffeic acid (CHEBI:16433) is a caffeic acid (CHEBI:36281)
trans-caffeic acid (CHEBI:16433) is conjugate acid of trans-caffeate (CHEBI:57770)
Incoming (2S,3R)-trans-caftaric acid (CHEBI:76075) has functional parent trans-caffeic acid (CHEBI:16433)
1,3,4,5-tetracaffeoylquinic acid (CHEBI:512) has functional parent trans-caffeic acid (CHEBI:16433)
1,3-dicaffeoylquinic acid (CHEBI:520) has functional parent trans-caffeic acid (CHEBI:16433)
1-caffeoyl-β-D-glucose (CHEBI:614) has functional parent trans-caffeic acid (CHEBI:16433)
1-caffeoyl-5-feruloylquinic acid (CHEBI:88343) has functional parent trans-caffeic acid (CHEBI:16433)
2-O-caffeoyl maslinic acid (CHEBI:65547) has functional parent trans-caffeic acid (CHEBI:16433)
3,4-dihydroxy-5-prenylcinnamic acid (CHEBI:65784) has functional parent trans-caffeic acid (CHEBI:16433)
3,5-di-O-caffeoyl quinic acid (CHEBI:65751) has functional parent trans-caffeic acid (CHEBI:16433)
4-O-trans-caffeoylquinic acid (CHEBI:75491) has functional parent trans-caffeic acid (CHEBI:16433)
5-[(E)-caffeoyl]shikimic acid (CHEBI:2106) has functional parent trans-caffeic acid (CHEBI:16433)
7-O-[6-(6-methoxycaffeoyl)glucosyl]isovitexin (CHEBI:75420) has functional parent trans-caffeic acid (CHEBI:16433)
Cuscuta propenamide 1 (CHEBI:65700) has functional parent trans-caffeic acid (CHEBI:16433)
trans-5-O-caffeoyl-D-quinic acid (CHEBI:16384) has functional parent trans-caffeic acid (CHEBI:16433)
trans-caffeoyl-CoA (CHEBI:87449) has functional parent trans-caffeic acid (CHEBI:16433)
acteoside (CHEBI:132853) has functional parent trans-caffeic acid (CHEBI:16433)
caffeic acid 3-glucoside (CHEBI:3293) has functional parent trans-caffeic acid (CHEBI:16433)
caffeic acid 3-sulfate (CHEBI:90242) has functional parent trans-caffeic acid (CHEBI:16433)
caffeic acid 3-sulfate(2−) (CHEBI:133740) has functional parent trans-caffeic acid (CHEBI:16433)
caffeoylglycolic acid methyl ester (CHEBI:65548) has functional parent trans-caffeic acid (CHEBI:16433)
calabricoside B (CHEBI:65551) has functional parent trans-caffeic acid (CHEBI:16433)
chlorogenic acid (CHEBI:16112) has functional parent trans-caffeic acid (CHEBI:16433)
ethyl trans-caffeate (CHEBI:132714) has functional parent trans-caffeic acid (CHEBI:16433)
evolvoid A (CHEBI:65890) has functional parent trans-caffeic acid (CHEBI:16433)
gelsemiol-6'-trans-caffeoyl-1-glucoside (CHEBI:65957) has functional parent trans-caffeic acid (CHEBI:16433)
litseaefoloside C (CHEBI:66582) has functional parent trans-caffeic acid (CHEBI:16433)
malvidin 3-O-{6-O-[(E)-caffeoyl]-β-D-glucoside} (CHEBI:131453) has functional parent trans-caffeic acid (CHEBI:16433)
methyl 3,4-dicaffeoylquinate (CHEBI:85153) has functional parent trans-caffeic acid (CHEBI:16433)
quercetin 3-O-α-(6'''-caffeoylglucosyl-β-1,2-rhamnoside) (CHEBI:66284) has functional parent trans-caffeic acid (CHEBI:16433)
rosmarinic acid (CHEBI:17226) has functional parent trans-caffeic acid (CHEBI:16433)
subulatin (CHEBI:66533) has functional parent trans-caffeic acid (CHEBI:16433)
trans-caffeate (CHEBI:57770) is conjugate base of trans-caffeic acid (CHEBI:16433)
IUPAC Name
(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
Synonyms Sources
3,4-dihydroxy-trans-cinnamate ChEBI
3,4-Dihydroxy-trans-cinnamate KEGG COMPOUND
3,4-Dihydroxy-trans-cinnamate KEGG COMPOUND
3,4-Dihydroxycinnamic acid KEGG COMPOUND
CAFFEIC ACID PDBeChem
Caffeic acid KEGG COMPOUND
trans-caffeate ChEBI
trans-Caffeate KEGG COMPOUND
Database Links Databases
C00000615 KNApSAcK
C01197 KEGG COMPOUND
C01481 KEGG COMPOUND
Caffeic_acid Wikipedia
DHC PDBeChem
HMDB0001964 HMDB
View more database links
Registry Numbers Types Sources
1954563 Reaxys Registry Number Reaxys
1954563 Beilstein Registry Number Beilstein
331-39-5 CAS Registry Number KEGG COMPOUND
501-16-6 CAS Registry Number ChemIDplus
Last Modified
13 October 2016