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CHEBI:16384 - trans-5-O-caffeoyl-D-quinic acid

ChEBI IDCHEBI:16384
ChEBI Nametrans-5-O-caffeoyl-D-quinic acid
Stars
ASCII Nametrans-5-O-caffeoyl-D-quinic acid
DefinitionA cinnamate ester obtained by formal condensation of the carboxy group of trans-caffeic acid with the 5-hydroxy group of quinic acid.
Secondary ChEBI IDsCHEBI:10717, CHEBI:12867, CHEBI:27064, CHEBI:31333
Last Modified28 July 2014
DownloadsMolfile
FormulaC16H18O9
Net Charge0
Average Mass354.311
Monoisotopic Mass354.09508
SMILES[H][C@]1(O)[C@H](O)C[C@](O)(C(=O)O)C[C@H]1OC(=O)/C=C/c1ccc(O)c(O)c1
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-NXLLHMKUSA-N
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Role:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
ChEBI Ontology
Outgoing Relation(s)
trans-5-O-caffeoyl-D-quinic acid (CHEBI:16384) has functional parent (−)-quinic acid (CHEBI:17521)
trans-5-O-caffeoyl-D-quinic acid (CHEBI:16384) has functional parent trans-caffeic acid (CHEBI:16433)
trans-5-O-caffeoyl-D-quinic acid (CHEBI:16384) has role plant metabolite (CHEBI:76924)
trans-5-O-caffeoyl-D-quinic acid (CHEBI:16384) is a cinnamate ester (CHEBI:36087)
trans-5-O-caffeoyl-D-quinic acid (CHEBI:16384) is a cyclitol carboxylic acid (CHEBI:36123)
trans-5-O-caffeoyl-D-quinic acid (CHEBI:16384) is conjugate acid of trans-5-O-caffeoyl-D-quinate (CHEBI:57754)
Incoming Relation(s)
trans-5-O-caffeoyl-D-quinate (CHEBI:57754) is conjugate base of trans-5-O-caffeoyl-D-quinic acid (CHEBI:16384)
IUPAC Name 
1D-[1(OH),3,4/5]-3-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-1,4,5-trihydroxycyclohexanecarboxylic acid
Synonyms  Source
(1R,3R,4S,5R)-3-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-1,4,5-trihydroxycyclohexanecarboxylic acidIUPAC
Caffeoyl quinic acidKEGG COMPOUND
trans-5-O-Caffeoyl-D-quinateKEGG COMPOUND
Neochlorogenic acidKEGG COMPOUND
trans-Neochlorogenic acidKEGG COMPOUND
NeochlorogenateKEGG COMPOUND
Manual XrefsDatabases
C17147KEGG COMPOUND
Registry NumbersSources
Reaxys:3039251Reaxys
CAS:202650-88-2KEGG COMPOUND
CAS:906-33-2KEGG COMPOUND
Citations