CHEBI:2106 - 5-[(E)-caffeoyl]shikimic acid

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name 5-[(E)-caffeoyl]shikimic acid
ChEBI ASCII Name 5-[(E)-caffeoyl]shikimic acid
Definition A carboxylic ester obtained by formal condensation of the carboxy group of (E)-caffeic acid with the 5-hydroxy group of shikimic acid.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C16H16O8
Net Charge 0
Average Mass 336.294
Monoisotopic Mass 336.08452
InChI InChI=1S/C16H16O8/c17-10-3-1-8(5-11(10)18)2-4-14(20)24-13-7-9(16(22)23)6-12(19)15(13)21/h1-6,12-13,15,17-19,21H,7H2,(H,22,23)/b4-2+/t12-,13-,15-/m1/s1
SMILES C1(=CC=C(C(=C1)O)O)/C=C/C(O[C@H]2[C@@H]([C@@H](C=C(C2)C(=O)O)O)O)=O
Metabolite of Species Details
Urceola huaitingii (NCBI:txid1398147) See: PubMed
Arabidopsis thaliana (NCBI:txid3702) See: PubMed
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 5-[(E)-caffeoyl]shikimic acid (CHEBI:2106) has functional parent trans-caffeic acid (CHEBI:16433)
5-[(E)-caffeoyl]shikimic acid (CHEBI:2106) has functional parent shikimic acid (CHEBI:16119)
5-[(E)-caffeoyl]shikimic acid (CHEBI:2106) has role plant metabolite (CHEBI:76924)
5-[(E)-caffeoyl]shikimic acid (CHEBI:2106) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
5-[(E)-caffeoyl]shikimic acid (CHEBI:2106) is a carboxylic ester (CHEBI:33308)
5-[(E)-caffeoyl]shikimic acid (CHEBI:2106) is a catechols (CHEBI:33566)
5-[(E)-caffeoyl]shikimic acid (CHEBI:2106) is a cyclohexenecarboxylic acid (CHEBI:23483)
5-[(E)-caffeoyl]shikimic acid (CHEBI:2106) is conjugate acid of 5-[(E)-caffeoyl]shikimate (CHEBI:91005)
Incoming 5-[(E)-caffeoyl]shikimate (CHEBI:91005) is conjugate base of 5-[(E)-caffeoyl]shikimic acid (CHEBI:2106)
(3R,4R,5R)-5-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4-dihydroxycyclohex-1-ene-1-carboxylic acid
5-(trans-caffeoyl)shikimic acid
Synonym Source
5-caffeoylshikimic acid ChEBI
Manual Xrefs Databases
C00002720 KNApSAcK
View more database links
Registry Numbers Types Sources
5610056 Reaxys Registry Number Reaxys
73263-62-4 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
19579182 PubMed citation Europe PMC
23950498 PubMed citation Europe PMC
Last Modified
11 March 2016