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CHEBI:16112 - chlorogenic acid

Default Structure
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:
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:
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
[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
5-O-(3,4-Dihydroxycinnamoyl)-L-quinic acidChemIDplus
Caffeoyl quinic acidKEGG COMPOUND
Manual XrefsDatabases
C00002724KNApSAcK
C00852KEGG COMPOUND
C00852KEGG COMPOUND
CAFFEOYLQUINATEMetaCyc
Chlorogenic_acidWikipedia
HMDB0003164HMDB
Registry NumbersSources
Reaxys:2017157Reaxys
CAS:327-97-9KEGG COMPOUND
Citations