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Examples:
iron*
,
InChI=1S/CH4O/c1-2/h2H,1H3
,
caffeine
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ChEBI
> Main
CHEBI:17395 -
cis
-caffeic acid
Main
ChEBI Ontology
Automatic Xrefs
Reactions
Pathways
Models
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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Molfile
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Molfile
Molfile
Formula
C9H8O4
Net Charge
0
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 (Br
o
nsted 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
(2
S
,3
R
)-
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
(2
Z
)-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
Manual Xrefs
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
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 January 2019