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InChI=1S/CH4O/c1-2/h2H,1H3
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CHEBI:520 - 1,3-dicaffeoylquinic acid
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ChEBI Name
1,3-dicaffeoylquinic acid
ChEBI ID
CHEBI:520
Definition
An alkyl caffeate ester obtained by the formal condensation of hydroxy groups at positions 1 and 3 of (
)-quinic acid with two molecules of
trans
-caffeic acid.
Stars
This entity has been manually annotated by the ChEBI Team.
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Formula
C25H24O12
Net Charge
0
Average Mass
516.45090
Monoisotopic Mass
516.12678
InChI
InChI=1S/C25H24O12/c26-
15-
5-
1-
13(9-
17(15)
28)
3-
7-
21(31)
36-
20-
12-
25(24(34)
35,11-
19(30)
23(20)
33)
37-
22(32)
8-
4-
14-
2-
6-
16(27)
18(29)
10-
14/h1-
10,19-
20,23,26-
30,33H,11-
12H2,(H,34,35)
/b7-
3+,8-
4+/t19-
,20-
,23+,25-
/m1/s1
InChIKey
YDDUMTOHNYZQPO-RVXRWRFUSA-N
SMILES
O[C@@H]1C[C@](C[C@@H](OC(=O)\C=C\c2ccc(O)c(O)c2)[C@H]1O)(OC(=O)\C=C\c1ccc(O)c(O)c1)C(O)=O
Metabolite of Species
Details
Centella asiatica
(NCBI:txid48106)
See:
MetaboLights Study
Roles Classification
Chemical Role
(s):
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
quinic acid
)
View more via ChEBI Ontology
ChEBI Ontology
Outgoing
1,3-dicaffeoylquinic acid (
CHEBI:520
)
has functional parent
(−)-quinic acid (
CHEBI:17521
)
1,3-dicaffeoylquinic acid (
CHEBI:520
)
has functional parent
trans
-caffeic acid (
CHEBI:16433
)
1,3-dicaffeoylquinic acid (
CHEBI:520
)
has role
plant metabolite (
CHEBI:76924
)
1,3-dicaffeoylquinic acid (
CHEBI:520
)
is a
alkyl caffeate ester (
CHEBI:65331
)
1,3-dicaffeoylquinic acid (
CHEBI:520
)
is a
quinic acid (
CHEBI:26493
)
1,3-dicaffeoylquinic acid (
CHEBI:520
)
is conjugate acid of
1,3-dicaffeoylquinate (
CHEBI:86332
)
Incoming
1,3-dicaffeoylquinate (
CHEBI:86332
)
is conjugate base of
1,3-dicaffeoylquinic acid (
CHEBI:520
)
IUPAC Name
(1
R
,3
R
,4
S
,5
R
)-
1,3-
bis{[(2
E
)-
3-
(3,4-
dihydroxyphenyl)prop-
2-
enoyl]oxy}-
4,5-
dihydroxycyclohexane-
1-
carboxylic acid
Synonyms
Sources
1,5-Dicaffeoylquinic acid
ChEBI
Cynarin
KEGG COMPOUND
Manual Xrefs
Databases
3124
DrugCentral
C00002733
KNApSAcK
C10445
KEGG COMPOUND
HMDB0030093
HMDB
View more database links
Registry Numbers
Types
Sources
30964-13-7
CAS Registry Number
KEGG COMPOUND
3189399
Reaxys Registry Number
Reaxys
Last Modified
22 October 2018