CHEBI:1945 - 4-p-coumaroylquinic acid

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ChEBI Name 4-p-coumaroylquinic acid
ChEBI ID CHEBI:1945
ChEBI ASCII Name 4-p-coumaroylquinic acid
Definition A cinnamate ester obtained by formal condensation of the carboxy group of 4-coumaric 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 C16H18O8
Net Charge 0
Average Mass 338.312
Monoisotopic Mass 338.10017
InChI InChI=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
InChIKey XWRHBGVVCOSNKO-NCZKRNLISA-N
SMILES [H]C(=CC(=O)O[C@H]1[C@H](O)C[C@@](O)(C[C@H]1O)C(O)=O)C1=CC=C(O)C=C1
Metabolite of Species Details
Lophatherum gracile (NCBI:txid29683) See: PubMed
Cydonia oblonga (NCBI:txid36610) Isolated from peel and pulp. See: PubMed
Nicotiana tabacum (NCBI:txid4097) See: DOI
Brassica oleracea var. costata (NCBI:txid416546) Found in leaf (BTO:0000713). See: DOI
Camellia sinensis (NCBI:txid4442) See: PubMed
Juglans regia (NCBI:txid51240) Found in leaf (BTO:0000713). See: DOI
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): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 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 Sources
4-coumaroylquinic acid ChEBI
4-O-coumaroylquinic acid ChEBI
4-O-p-coumaroylquinic acid ChEBI
Manual Xrefs Databases
30785511 ChemSpider
C00002730 KNApSAcK
C10441 KEGG COMPOUND
FDB000237 FooDB
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Registry Numbers Types Sources
2706509 Reaxys Registry Number Reaxys
93451-44-6 CAS Registry Number KEGG COMPOUND
93451-44-6 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
20795622 PubMed citation Europe PMC
21184087 PubMed citation Europe PMC
22118617 PubMed citation Europe PMC
25527702 PubMed citation Europe PMC
26988497 PubMed citation Europe PMC
28490099 PubMed citation Europe PMC
29853055 PubMed citation Europe PMC
30827583 PubMed citation Europe PMC
IND43637997 Agricola citation Europe PMC
IND43643995 Agricola citation Europe PMC
IND43824488 Agricola citation Europe PMC
IND601139292 Agricola citation Europe PMC
Last Modified
09 August 2021