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CHEBI:75489 - 5-O-cis-caffeoylquinic acid

ChEBI IDCHEBI:75489
ChEBI Name5-O-cis-caffeoylquinic acid
Stars
ASCII Name5-O-cis-caffeoylquinic acid
DefinitionA cinnamate ester obtained by formal condensation of the carboxy group of cis-caffeic acid with the 5-hydroxy group of (+)-quinic acid.
Last Modified21 November 2013
Submittermwilliams
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-XYXZIBEBSA-N
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Role:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
5-O-cis-caffeoylquinic acid (CHEBI:75489) has functional parent (+)-quinic acid (CHEBI:36124)
5-O-cis-caffeoylquinic acid (CHEBI:75489) has functional parent cis-caffeic acid (CHEBI:17395)
5-O-cis-caffeoylquinic acid (CHEBI:75489) has role metabolite (CHEBI:25212)
5-O-cis-caffeoylquinic acid (CHEBI:75489) is a cinnamate ester (CHEBI:36087)
5-O-cis-caffeoylquinic acid (CHEBI:75489) is a cyclitol carboxylic acid (CHEBI:36123)
IUPAC Name 
(1S,3R,4R,5R)-3-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexanecarboxylic acid
Synonyms  Source
cis-5-O-caffeoylquinic acidChEBI
cis-chlorogenic acidChEBI
5-O-(Z)-caffeoylquinic acidChEBI
Manual XrefsDatabases
HMDB0029278HMDB
Registry NumbersSources
Reaxys:9588915Reaxys