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CHEBI:1945 - 4-p-coumaroylquinic acid

ChEBI IDCHEBI:1945
ChEBI Name4-p-coumaroylquinic acid
Stars
ASCII Name4-p-coumaroylquinic acid
DefinitionA cinnamate ester obtained by formal condensation of the carboxy group of 4-coumaric acid with the 4-hydroxy group of (−)-quinic acid.
Last Modified9 August 2021
DownloadsMolfile
FormulaC16H18O8
Net Charge0
Average Mass338.312
Monoisotopic Mass338.10017
SMILES[H]C(=CC(=O)O[C@H]1[C@H](O)C[C@](O)(C(=O)O)C[C@H]1O)c1ccc(O)cc1
InChIInChI=1S/C16H18O8/c17-10-4-1-9(2-5-10)3-6-13(20)24-14-11(18)7-16(23,15(21)22)8-12(14)19/h1-6,11-12,14,17-19,23H,7-8H2,(H,21,22)/t11-,12-,14-,16+/m1/s1
InChIKeyXWRHBGVVCOSNKO-NCZKRNLISA-N
Species of MetaboliteComponentSourceComments
Camellia sinensis (ncbitaxon:4442) - PubMed (26988497)
Cydonia oblonga (ncbitaxon:36610) - PubMed (28490099) Isolated from peel and pulp.
Lophatherum gracile (ncbitaxon:29683) - PubMed (25527702)
Nicotiana tabacum (ncbitaxon:4097) - DOI (10.1016/j.plantsci.2011.02.009)
Brassica oleracea var. costata (ncbitaxon:416546) leaf (BTO:0000713) DOI (10.1007/s00217-005-0104-0)
Juglans regia (ncbitaxon:51240) leaf (BTO:0000713) DOI (10.1016/j.foodchem.2004.01.055)
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)
4-p-coumaroylquinic acid (CHEBI:1945) has functional parent (−)-quinic acid (CHEBI:17521)
4-p-coumaroylquinic acid (CHEBI:1945) has functional parent 4-coumaric acid (CHEBI:36090)
4-p-coumaroylquinic acid (CHEBI:1945) has role plant metabolite (CHEBI:76924)
4-p-coumaroylquinic acid (CHEBI:1945) is a cinnamate ester (CHEBI:36087)
4-p-coumaroylquinic acid (CHEBI:1945) is a cyclitol carboxylic acid (CHEBI:36123)
Incoming Relation(s)
trans-4-p-coumaroylquinic acid (CHEBI:176887) is a 4-p-coumaroylquinic acid (CHEBI:1945)
IUPAC Name 
(1S,3R,4S,5R)-1,3,5-trihydroxy-4-{[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohexanecarboxylic acid
Synonyms  Source
4-coumaroylquinic acidChEBI
4-O-coumaroylquinic acidChEBI
4-O-p-coumaroylquinic acidChEBI
Manual XrefsDatabases
C10441KEGG COMPOUND
C00002730KNApSAcK
FDB000237FooDB
30785511ChemSpider
Registry NumbersSources
Reaxys:2706509Reaxys
CAS:93451-44-6KEGG COMPOUND
CAS:93451-44-6ChemIDplus
Citations