CHEBI:16112 - chlorogenic acid

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ChEBI Name chlorogenic acid
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
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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
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
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)
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
Chlorogenic_acid Wikipedia
HMDB0003164 HMDB
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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