CHEBI:520 - 1,3-dicaffeoylquinic acid

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ChEBI Name 1,3-dicaffeoylquinic acid
ChEBI ID CHEBI:520
Definition An 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C25H24O12
Net Charge 0
Average Mass 516.45090
Monoisotopic Mass 516.127
InChI InChI=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
InChIKey YDDUMTOHNYZQPO-RVXRWRFUSA-N
SMILES O[C@@H]1C[C@](C[C@@H](OC(=O)\C=C\c2ccc(O)c(O)c2)[C@H]1O)(OC(=O)\C=C\c1ccc(O)c(O)c1)C(O)=O
Metabolite of Species Details
Centella asiatica (NCBI:txid48106) See: MetaboLights Study
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.
(via quinic acid )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 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 Sources
1,5-Dicaffeoylquinic acid ChEBI
Cynarin KEGG COMPOUND
Manual Xrefs Databases
3124 DrugCentral
C00002733 KNApSAcK
C10445 KEGG COMPOUND
HMDB0030093 HMDB
View more database links
Registry Numbers Types Sources
30964-13-7 CAS Registry Number KEGG COMPOUND
3189399 Reaxys Registry Number Reaxys
Last Modified
22 October 2018