CHEBI:65751 - 3,5-di-O-caffeoyl quinic acid

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ChEBI Name 3,5-di-O-caffeoyl quinic acid
ChEBI ASCII Name 3,5-di-O-caffeoyl quinic acid
Definition A carboxylic ester that is the diester obtained by the condensation of the hydroxy groups at positions 3 and 5 of (−)-quinic acid with the carboxy group of trans-caffeic acid. Isolated from Brazilian propolis and Suaeda glauca, it exhibits hepatoprotective and cytotoxic activities.
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 516.12678
InChI InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(30)36-19-11-25(35,24(33)34)12-20(23(19)32)37-22(31)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-29,32,35H,11-12H2,(H,33,34)/b7-3+,8-4+/t19-,20-,23-,25+/m1/s1
SMILES O[C@H]1[C@@H](C[C@@](O)(C[C@H]1OC(=O)\C=C\c1ccc(O)c(O)c1)C(O)=O)OC(=O)\C=C\c1ccc(O)c(O)c1
Metabolite of Species Details
Dichrocephala bicolor (IPNI:201282-1) Found in whole plant (BTO:0001461). See: DOI
Suaeda glauca (NCBI:txid397272) Found in whole plant (BTO:0001461). See: PubMed
Solidago virgaaurea var. gigantea (NCBI:txid462879) Found in aerial part (BTO:0001658). See: PubMed
Phagnalon rupestre (NCBI:txid943712) Found in aerial part (BTO:0001658). Ethyl acetate soluble fraction from methanolic extract of aerial parts See: PubMed
Brazilian propolis 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): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application(s): hepatoprotective agent
Any compound that is able to prevent damage to the liver.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 3,5-di-O-caffeoyl quinic acid (CHEBI:65751) has functional parent (−)-quinic acid (CHEBI:17521)
3,5-di-O-caffeoyl quinic acid (CHEBI:65751) has functional parent trans-caffeic acid (CHEBI:16433)
3,5-di-O-caffeoyl quinic acid (CHEBI:65751) has role antineoplastic agent (CHEBI:35610)
3,5-di-O-caffeoyl quinic acid (CHEBI:65751) has role hepatoprotective agent (CHEBI:62868)
3,5-di-O-caffeoyl quinic acid (CHEBI:65751) has role metabolite (CHEBI:25212)
3,5-di-O-caffeoyl quinic acid (CHEBI:65751) is a carboxylic ester (CHEBI:33308)
3,5-di-O-caffeoyl quinic acid (CHEBI:65751) is a cyclitol carboxylic acid (CHEBI:36123)
Incoming methyl 3,5-di-O-caffeoyl quinate (CHEBI:66708) has functional parent 3,5-di-O-caffeoyl quinic acid (CHEBI:65751)
(3R,5R)-3,5-bis{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4-dihydroxycyclohexanecarboxylic acid
Synonyms Sources
(1S,3R,4S,5R)-1,3,4,5-tetrahydroxy-1-carboxycyclohexane3,5-di-3-(3,4-dihydroxyphenyl)propenoate ChEBI
3,5-Dicaffeoylquinic acid HMDB
Isochlorogenic acid a HMDB
Quinic acid 3,5-di-O-caffeate HMDB
Manual Xref Database
HMDB0030706 HMDB
View more database links
Registry Number Type Source
4895191 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
15022716 PubMed citation Europe PMC
18481014 PubMed citation Europe PMC
21469692 PubMed citation Europe PMC
8951168 PubMed citation Europe PMC
Last Modified
09 April 2013