CHEBI:66708 - methyl 3,5-di-O-caffeoyl quinate

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ChEBI Name methyl 3,5-di-O-caffeoyl quinate
ChEBI ID CHEBI:66708
ChEBI ASCII Name methyl 3,5-di-O-caffeoyl quinate
Definition A methyl ester resulting from the formal condensation of the carboxy group of 3,5-di-O-caffeoyl quinic acid with methanol. Isolated from Suaeda glauca and Dichrocephala bicolor, it exhibits hepatoprotective activity.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C26H26O12
Net Charge 0
Average Mass 530.47740
Monoisotopic Mass 530.14243
InChI InChI=1S/C26H26O12/c1-36-25(34)26(35)12-20(37-22(31)8-4-14-2-6-16(27)18(29)10-14)24(33)21(13-26)38-23(32)9-5-15-3-7-17(28)19(30)11-15/h2-11,20-21,24,27-30,33,35H,12-13H2,1H3/b8-4+,9-5+/t20-,21-,24-,26+/m1/s1
InChIKey VEBNYMXKXIIGFX-VOHNXBSUSA-N
SMILES COC(=O)[C@@]1(O)C[C@@H](OC(=O)\C=C\c2ccc(O)c(O)c2)[C@H](O)[C@@H](C1)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
Roles Classification
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing methyl 3,5-di-O-caffeoyl quinate (CHEBI:66708) has functional parent 3,5-di-O-caffeoyl quinic acid (CHEBI:65751)
methyl 3,5-di-O-caffeoyl quinate (CHEBI:66708) has role hepatoprotective agent (CHEBI:62868)
methyl 3,5-di-O-caffeoyl quinate (CHEBI:66708) has role metabolite (CHEBI:25212)
methyl 3,5-di-O-caffeoyl quinate (CHEBI:66708) is a catechols (CHEBI:33566)
methyl 3,5-di-O-caffeoyl quinate (CHEBI:66708) is a cinnamate ester (CHEBI:36087)
methyl 3,5-di-O-caffeoyl quinate (CHEBI:66708) is a methyl ester (CHEBI:25248)
methyl 3,5-di-O-caffeoyl quinate (CHEBI:66708) is a secondary alcohol (CHEBI:35681)
methyl 3,5-di-O-caffeoyl quinate (CHEBI:66708) is a tertiary alcohol (CHEBI:26878)
IUPAC Name
methyl (3R,5R)-3,5-bis{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4-dihydroxycyclohexanecarboxylate
Manual Xref Database
24692051 ChemSpider
View more database links
Registry Number Type Source
9172717 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
Last Modified
06 March 2015