CHEBI:16112 - chlorogenic acid

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ChEBI Name chlorogenic acid
ChEBI ID CHEBI:16112
Definition A cinnamate ester obtained by formal condensation of the carboxy group of trans-caffeic acid with the 3-hydroxy group of quinic acid. It is an intermediate metabolite in the biosynthesis of lignin.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:3625, CHEBI:13972, CHEBI:23145
Supplier Information ChemicalBook:CB2478906, eMolecules:492483, eMolecules:29541115, Selleckchem:Chlorogenic-acid, ZINC000002138728
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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-JUHZACGLSA-N
SMILES O[C@@H]1C[C@](O)(C[C@@H](OC(=O)\C=C\c2ccc(O)c(O)c2)[C@@H]1O)C(O)=O
Roles Classification
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.
food component
A physiological role played by any substance that is distributed in foodstuffs. It includes materials derived from plants or animals, such as vitamins or minerals, as well as environmental contaminants.
Application(s): astringent
A compound that causes the contraction of body tissues, typically used to reduce bleeding from minor abrasions.
(via tannin )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing chlorogenic acid (CHEBI:16112) has functional parent (−)-quinic acid (CHEBI:17521)
chlorogenic acid (CHEBI:16112) has functional parent trans-caffeic acid (CHEBI:16433)
chlorogenic acid (CHEBI:16112) has role food component (CHEBI:78295)
chlorogenic acid (CHEBI:16112) has role plant metabolite (CHEBI:76924)
chlorogenic acid (CHEBI:16112) is a cinnamate ester (CHEBI:36087)
chlorogenic acid (CHEBI:16112) is a tannin (CHEBI:26848)
chlorogenic acid (CHEBI:16112) is conjugate acid of chlorogenate (CHEBI:57644)
Incoming chlorogenate (CHEBI:57644) is conjugate base of chlorogenic acid (CHEBI:16112)
IUPAC Name
edit(1S,3R,4R,5R)-3-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid
Synonyms Sources
3-(3,4-Dihydroxycinnamoyl)quinic acid ChemIDplus
3-Caffeoylquinic acid ChemIDplus
3-O-Caffeoylquinic acid ChemIDplus
5-O-(3,4-Dihydroxycinnamoyl)-L-quinic acid ChemIDplus
[1S-(1alpha,3beta,4alpha,5alpha)]3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid ChEBI
Caffeoyl quinic acid KEGG COMPOUND
Chlorogenate KEGG COMPOUND
Chlorogenic acid KEGG COMPOUND
trans-5-O-Caffeoyl-D-quinate KEGG COMPOUND
Manual Xrefs Databases
C00002724 KNApSAcK
C00852 KEGG COMPOUND
CAFFEOYLQUINATE MetaCyc
Chlorogenic_acid Wikipedia
HMDB0003164 HMDB
View more database links
Registry Numbers Types Sources
2017157 Reaxys Registry Number Reaxys
327-97-9 CAS Registry Number KEGG COMPOUND
Citations Waiting for Citations Types Sources
16507475 PubMed citation Europe PMC
22770225 PubMed citation Europe PMC
Last Modified
08 January 2016