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InChI=1S/CH4O/c1-2/h2H,1H3
,
caffeine
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ChEBI
> Main
CHEBI:16384 -
trans
-5-
O
-caffeoyl-
D
-quinic acid
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ChEBI Name
trans
-5-
O
-caffeoyl-
D
-quinic acid
ChEBI ID
CHEBI:16384
ChEBI ASCII Name
trans-5-O-caffeoyl-D-quinic acid
Definition
A cinnamate ester obtained by formal condensation of the carboxy group of trans-caffeic acid with the 5-hydroxy group of quinic acid.
Stars
This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs
CHEBI:10717, CHEBI:12867, CHEBI:27064, CHEBI:31333
Supplier Information
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Formula
C16H18O9
Net Charge
0
Average Mass
354.30870
Monoisotopic Mass
354.09508
InChI
InChI=1S/C16H18O9/c17-
9-
3-
1-
8(5-
10(9)
18)
2-
4-
13(20)
25-
12-
7-
16(24,15(22)
23)
6-
11(19)
14(12)
21/h1-
5,11-
12,14,17-
19,21,24H,6-
7H2,(H,22,23)
/b4-
2+/t11-
,12-
,14+,16-
/m1/s1
InChIKey
CWVRJTMFETXNAD-NXLLHMKUSA-N
SMILES
[H][C@]1(O)[C@H](O)C[C@@](O)(C[C@H]1OC(=O)\C=C\c1ccc(O)c(O)c1)C(O)=O
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing
trans
-5-
O
-caffeoyl-
D
-quinic acid (
CHEBI:16384
)
has functional parent
(−)-quinic acid (
CHEBI:17521
)
trans
-5-
O
-caffeoyl-
D
-quinic acid (
CHEBI:16384
)
has functional parent
trans
-caffeic acid (
CHEBI:16433
)
trans
-5-
O
-caffeoyl-
D
-quinic acid (
CHEBI:16384
)
has role
plant metabolite (
CHEBI:76924
)
trans
-5-
O
-caffeoyl-
D
-quinic acid (
CHEBI:16384
)
is a
cinnamate ester (
CHEBI:36087
)
trans
-5-
O
-caffeoyl-
D
-quinic acid (
CHEBI:16384
)
is a
cyclitol carboxylic acid (
CHEBI:36123
)
trans
-5-
O
-caffeoyl-
D
-quinic acid (
CHEBI:16384
)
is conjugate acid of
trans
-5-
O
-caffeoyl-
D
-quinate (
CHEBI:57754
)
Incoming
trans
-5-
O
-caffeoyl-
D
-quinate (
CHEBI:57754
)
is conjugate base of
trans
-5-
O
-caffeoyl-
D
-quinic acid (
CHEBI:16384
)
IUPAC Name
1
D
-
[1(OH),3,4/5]-
3-
[(2
E
)-
3-
(3,4-
dihydroxyphenyl)prop-
2-
enoyloxy]-
1,4,5-
trihydroxycyclohexanecarboxylic acid
Synonyms
Sources
(1
R
,3
R
,4
S
,5
R
)-
3-
[(2
E
)-
3-
(3,4-
dihydroxyphenyl)prop-
2-
enoyloxy]-
1,4,5-
trihydroxycyclohexanecarboxylic acid
IUPAC
Caffeoyl quinic acid
KEGG COMPOUND
Neochlorogenate
KEGG COMPOUND
Neochlorogenic acid
KEGG COMPOUND
trans-5-O-Caffeoyl-D-quinate
KEGG COMPOUND
trans-Neochlorogenic acid
KEGG COMPOUND
Manual Xref
Database
C17147
KEGG COMPOUND
View more database links
Registry Numbers
Types
Sources
202650-88-2
CAS Registry Number
KEGG COMPOUND
3039251
Reaxys Registry Number
Reaxys
906-33-2
CAS Registry Number
KEGG COMPOUND
Citations
Types
Sources
19022950
PubMed citation
Europe PMC
24079179
PubMed citation
Europe PMC
24619353
PubMed citation
Europe PMC
24842397
PubMed citation
Europe PMC
Last Modified
28 July 2014