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

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ChEBI Name 5-O-cis-caffeoylquinic acid
ChEBI ID CHEBI:75489
ChEBI ASCII Name 5-O-cis-caffeoylquinic acid
Definition A cinnamate ester obtained by formal condensation of the carboxy group of cis-caffeic acid with the 5-hydroxy group of (+)-quinic acid.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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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-XYXZIBEBSA-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
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Sources
5-O-(Z)-caffeoylquinic acid ChEBI
cis-5-O-caffeoylquinic acid ChEBI
cis-chlorogenic acid ChEBI
Manual Xref Database
HMDB0029278 HMDB
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Registry Number Type Source
9588915 Reaxys Registry Number Reaxys
Last Modified
21 November 2013