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

ChEBI IDCHEBI:75491
ChEBI Name4-O-trans-caffeoylquinic acid
Stars
ASCII Name4-O-trans-caffeoylquinic acid
DefinitionA cinnamate ester obtained by formal condensation of the carboxy group of trans-caffeic acid with the 4-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]1[C@H](O)C[C@](O)(C(=O)O)C[C@H]1O
InChIInChI=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
InChIKeyGYFFKZTYYAFCTR-JUHZACGLSA-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.
Application:
hepatoprotective agent  Any compound that is able to prevent damage to the liver.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
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  Source
Cryptochlorogenic acidHMDB
4-(3,4-Dihydroxycinnamoyl)quinic acidHMDB
4-O-caffeoylquinic acidChEBI
4-Caffeoylquinic acidHMDB
4-O-(E)-caffeoylquinic acidChEBI
Manual XrefsDatabases
HMDB0030653HMDB
Registry NumbersSources
Reaxys:2708415Reaxys
CAS:905-99-7HMDB
Citations