CHEBI:75491 - 4-O-trans-caffeoylquinic acid

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ChEBI Name 4-O-trans-caffeoylquinic acid
ChEBI ID CHEBI:75491
ChEBI ASCII Name 4-O-trans-caffeoylquinic acid
Definition A cinnamate ester obtained by formal condensation of the carboxy group of trans-caffeic acid with the 4-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(21)25-14-11(19)6-16(24,15(22)23)7-12(14)20/h1-5,11-12,14,17-20,24H,6-7H2,(H,22,23)/b4-2+/t11-,12-,14-,16+/m1/s1
InChIKey GYFFKZTYYAFCTR-JUHZACGLSA-N
SMILES O[C@@H]1C[C@@](O)(C[C@@H](O)[C@H]1OC(=O)\C=C\c1ccc(O)c(O)c1)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.
Application(s): hepatoprotective agent
Any compound that is able to prevent damage to the liver.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 4-O-trans-caffeoylquinic acid (CHEBI:75491) has functional parent (+)-quinic acid (CHEBI:36124)
4-O-trans-caffeoylquinic acid (CHEBI:75491) has functional parent trans-caffeic acid (CHEBI:16433)
4-O-trans-caffeoylquinic acid (CHEBI:75491) has role hepatoprotective agent (CHEBI:62868)
4-O-trans-caffeoylquinic acid (CHEBI:75491) has role metabolite (CHEBI:25212)
4-O-trans-caffeoylquinic acid (CHEBI:75491) is a cinnamate ester (CHEBI:36087)
4-O-trans-caffeoylquinic acid (CHEBI:75491) is a cyclitol carboxylic acid (CHEBI:36123)
Incoming 4-O-E-caffeoylquinic acid methyl ester (CHEBI:145092) has functional parent 4-O-trans-caffeoylquinic acid (CHEBI:75491)
IUPAC Name
(1S,3R,4S,5R)-4-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,3,5-trihydroxycyclohexanecarboxylic acid
Synonyms Sources
4-(3,4-Dihydroxycinnamoyl)quinic acid HMDB
4-Caffeoylquinic acid HMDB
4-O-(E)-caffeoylquinic acid ChEBI
4-O-caffeoylquinic acid ChEBI
Cryptochlorogenic acid HMDB
Manual Xref Database
HMDB0030653 HMDB
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Registry Numbers Types Sources
2708415 Reaxys Registry Number Reaxys
905-99-7 CAS Registry Number HMDB
Citations Waiting for Citations Types Sources
23798877 PubMed citation Europe PMC
23829630 PubMed citation Europe PMC
23973760 PubMed citation Europe PMC
24061869 PubMed citation Europe PMC
Last Modified
21 November 2013