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InChI=1S/CH4O/c1-2/h2H,1H3
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ChEBI
> Main
CHEBI:136555 - 1-
O
-caffeoylquinic acid
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ChEBI Ontology
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ChEBI Name
1-
O
-caffeoylquinic acid
ChEBI ID
CHEBI:136555
ChEBI ASCII Name
1-O-caffeoylquinic acid
Definition
An alkyl caffeate ester obtained by the formal condensation of the carboxy group of
trans
-caffeic acid with the 1-hydroxy group of (−)-quinic acid.
Stars
This entity has been manually annotated by the ChEBI Team.
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Formula
C16H18O9
Net Charge
0
Average Mass
354.309
Monoisotopic Mass
354.09508
InChI
InChI=1S/C16H18O9/c17-
9-
3-
1-
8(5-
10(9)
18)
2-
4-
13(21)
25-
16(15(23)
24)
6-
11(19)
14(22)
12(20)
7-
16/h1-
5,11-
12,14,17-
20,22H,6-
7H2,(H,23,24)
/b4-
2+/t11-
,12-
,14-
,16+/m1/s1
InChIKey
GWTUHAXUUFROTF-JUHZACGLSA-N
SMILES
C(=O)(/C=C/C1=CC=C(O)C(O)=C1)O[C@@]2(C[C@@H](O)[C@@H]([C@@H](C2)O)O)C(O)=O
Metabolite of Species
Details
Tetrastigma hemsleyanum
(NCBI:txid1006121)
Found in leaf
(BTO:0000713)
. See:
PubMed
Lonicera japonica
(NCBI:txid105884)
Found in flower bud
(BTO:0000470)
. See:
PubMed
Cyclocarya paliurus
(NCBI:txid117167)
Found in leaf
(BTO:0000713)
. See:
DOI
Xanthium
(NCBI:txid36590)
Found in fruit
(BTO:0000486)
. See:
PubMed
Camellia sinensis
(NCBI:txid4442)
See:
MetaboLights Study
Canna edulis
(NCBI:txid4628)
Obtained from water-soluble extracts See:
DOI
Cynara cardunculus
var.
scolymus
(NCBI:txid59895)
See:
PubMed
Crepidiastrum sonchifolium
(NCBI:txid77563)
See:
PubMed
Roles Classification
Chemical Role
(s):
antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Br
o
nsted base).
(via
oxoacid
)
Biological Role
(s):
Camellia sinensis metabolite
Any plant metabolite that is produced by
Camellia sinensis
.
NF-kappaB inhibitor
An inhibitor of NF-
kappa
B (nuclear factor
kappa
-light-chain-enhancer of activated B cells), a protein complex involved in the transcription of DNA.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
(via
quinic acid
)
Application
(s):
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing
1-
O
-caffeoylquinic acid (
CHEBI:136555
)
has functional parent
trans
-caffeic acid (
CHEBI:16433
)
1-
O
-caffeoylquinic acid (
CHEBI:136555
)
has parent hydride
(−)-quinic acid (
CHEBI:17521
)
1-
O
-caffeoylquinic acid (
CHEBI:136555
)
has role
Camellia sinensis
metabolite (
CHEBI:140160
)
1-
O
-caffeoylquinic acid (
CHEBI:136555
)
has role
antineoplastic agent (
CHEBI:35610
)
1-
O
-caffeoylquinic acid (
CHEBI:136555
)
has role
antioxidant (
CHEBI:22586
)
1-
O
-caffeoylquinic acid (
CHEBI:136555
)
has role
NF-κB inhibitor (
CHEBI:73240
)
1-
O
-caffeoylquinic acid (
CHEBI:136555
)
is a
alkyl caffeate ester (
CHEBI:65331
)
1-
O
-caffeoylquinic acid (
CHEBI:136555
)
is a
quinic acid (
CHEBI:26493
)
IUPAC Name
(1
S
,3
R
,4
S
,5
R
)-
1-
{[(2
E
)-
3-
(3,4-
dihydroxyphenyl)prop-
2-
enoyl]oxy}-
3,4,5-
trihydroxycyclohexane-
1-
carboxylic acid
Synonyms
Sources
1-Caffeoylquinic acid
ChemIDplus
1-
O
-(
trans
-caffeoyl)quinic acid
ChEBI
trans-1-o-Caffeoylquinic acid
ChemIDplus
Registry Numbers
Types
Sources
3173163
Reaxys Registry Number
Reaxys
928005-87-2
CAS Registry Number
ChemIDplus
Citations
Types
Sources
15884803
PubMed citation
Europe PMC
18830958
PubMed citation
Europe PMC
19185132
PubMed citation
Europe PMC
23661994
PubMed citation
Europe PMC
24151872
PubMed citation
Europe PMC
24228586
PubMed citation
Europe PMC
28873750
PubMed citation
Europe PMC
IND44292559
Agricola citation
Europe PMC
IND44619880
Agricola citation
Europe PMC
Last Modified
15 February 2018