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CHEBI:520 - 1,3-dicaffeoylquinic acid

ChEBI IDCHEBI:520
ChEBI Name1,3-dicaffeoylquinic acid
Stars
DefinitionAn alkyl caffeate ester obtained by the formal condensation of hydroxy groups at positions 1 and 3 of ()-quinic acid with two molecules of trans-caffeic acid.
Last Modified22 October 2018
DownloadsMolfile
FormulaC25H24O12
Net Charge0
Average Mass516.455
Monoisotopic Mass516.12678
SMILESO=C(/C=C/c1ccc(O)c(O)c1)O[C@@H]1C[C@@](OC(=O)/C=C/c2ccc(O)c(O)c2)(C(=O)O)C[C@@H](O)[C@@H]1O
InChIInChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(24(34)35,11-19(30)23(20)33)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,33H,11-12H2,(H,34,35)/b7-3+,8-4+/t19-,20-,23+,25-/m1/s1
InChIKeyYDDUMTOHNYZQPO-RVXRWRFUSA-N
Species of MetaboliteComponentSourceComments
Centella asiatica (ncbitaxon:48106) - MetaboLights (MTBLS175)
Roles Classification
Chemical Roles:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
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)
1,3-dicaffeoylquinic acid (CHEBI:520) has functional parent (−)-quinic acid (CHEBI:17521)
1,3-dicaffeoylquinic acid (CHEBI:520) has functional parent trans-caffeic acid (CHEBI:16433)
1,3-dicaffeoylquinic acid (CHEBI:520) has role plant metabolite (CHEBI:76924)
1,3-dicaffeoylquinic acid (CHEBI:520) is a alkyl caffeate ester (CHEBI:65331)
1,3-dicaffeoylquinic acid (CHEBI:520) is a quinic acid (CHEBI:26493)
1,3-dicaffeoylquinic acid (CHEBI:520) is conjugate acid of 1,3-dicaffeoylquinate (CHEBI:86332)
Incoming Relation(s)
1,3-dicaffeoylquinate (CHEBI:86332) is conjugate base of 1,3-dicaffeoylquinic acid (CHEBI:520)
IUPAC Name 
(1R,3R,4S,5R)-1,3-bis{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-4,5-dihydroxycyclohexane-1-carboxylic acid
Synonyms  Source
CynarinKEGG COMPOUND
1,5-Dicaffeoylquinic acidChEBI
Manual XrefsDatabases
C10445KEGG COMPOUND
C00002733KNApSAcK
HMDB0030093HMDB
3124DrugCentral
Registry NumbersSources
Reaxys:3189399Reaxys
CAS:30964-13-7KEGG COMPOUND