EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

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

ChEBI IDCHEBI:2106
ChEBI Name5-[(E)-caffeoyl]shikimic acid
Stars
ASCII Name5-[(E)-caffeoyl]shikimic acid
DefinitionA carboxylic ester obtained by formal condensation of the carboxy group of (E)-caffeic acid with the 5-hydroxy group of shikimic acid.
Last Modified11 March 2016
DownloadsMolfile
FormulaC16H16O8
Net Charge0
Average Mass336.296
Monoisotopic Mass336.08452
SMILESO=C(/C=C/c1ccc(O)c(O)c1)O[C@@H]1CC(C(=O)O)=C[C@@H](O)[C@H]1O
InChIInChI=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
InChIKeyQMPHZIPNNJOWQI-GDDAOPKQSA-N
Species of MetaboliteComponentSourceComments
Arabidopsis thaliana (ncbitaxon:3702) - PubMed (23950498)
Urceola huaitingii (ncbitaxon:1398147) - PubMed (19579182)
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)
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 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 a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
5-[(E)-caffeoyl]shikimic acid (CHEBI:2106) is conjugate acid of 5-[(E)-caffeoyl]shikimate (CHEBI:91005)
Incoming Relation(s)
5-[(E)-caffeoyl]shikimate (CHEBI:91005) is conjugate base of 5-[(E)-caffeoyl]shikimic acid (CHEBI:2106)
IUPAC Names 
(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 acidChEBI
Manual XrefsDatabases
C00002720KNApSAcK
C10434KEGG COMPOUND
CAFFEOYLSHIKIMATEMetaCyc
Registry NumbersSources
Reaxys:5610056Reaxys
CAS:73263-62-4KEGG COMPOUND
CAS:73263-62-4ChemIDplus
Citations