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CHEBI:16112 - chlorogenic acid

ChEBI IDCHEBI:16112
ChEBI Namechlorogenic acid
Stars
DefinitionA 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.
Secondary ChEBI IDsCHEBI:3625, CHEBI:13972, CHEBI:23145
Last Modified8 January 2016
DownloadsMolfile
FormulaC16H18O9
Net Charge0
Average Mass354.311
Monoisotopic Mass354.09508
SMILESO=C(/C=C/c1ccc(O)c(O)c1)O[C@@H]1C[C@](O)(C(=O)O)C[C@@H](O)[C@H]1O
InChIInChI=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
InChIKeyCWVRJTMFETXNAD-JUHZACGLSA-N
Wikipedia
Roles Classification
Biological Roles:
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.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application:
astringent  A compound that causes the contraction of body tissues, typically used to reduce bleeding from minor abrasions.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
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  Source
ChlorogenateKEGG COMPOUND
Chlorogenic acidKEGG COMPOUND
[1S-(1alpha,3beta,4alpha,5alpha)]3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acidChEBI
3-(3,4-Dihydroxycinnamoyl)quinic acidChemIDplus
3-Caffeoylquinic acidChemIDplus
3-O-Caffeoylquinic acidChemIDplus
Manual XrefsDatabases
C00852KEGG COMPOUND
C00852KEGG COMPOUND
CAFFEOYLQUINATEMetaCyc
HMDB0003164HMDB
Chlorogenic_acidWikipedia
C00002724KNApSAcK
Registry NumbersSources
Reaxys:2017157Reaxys
CAS:327-97-9KEGG COMPOUND
Citations