CHEBI:85153 - methyl 3,4-dicaffeoylquinate

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ChEBI Name methyl 3,4-dicaffeoylquinate
ChEBI ID CHEBI:85153
Definition An alkyl caffeate ester obtained by the formal condensation of hydroxy groups at positions 3 and 4 of methylquinate with two molecules of trans-caffeic acid respectively.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB8922249
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Formula C27H28O12
Net Charge 0
Average Mass 544.50400
Monoisotopic Mass 544.15808
InChI InChI=1S/C27H28O12/c1-36-21-12-16(4-8-18(21)29)6-10-24(33)39-25-20(31)13-27(35,26(34)37-2)14-22(25)38-23(32)9-5-15-3-7-17(28)19(30)11-15/h3-12,20,22,25,28-31,35H,13-14H2,1-2H3/b9-5+,10-6+/t20-,22-,25+,27-/m1/s1
InChIKey RTLCSWCXZWROFK-XKHJDCLGSA-N
SMILES COC(=O)[C@@]1(O)C[C@@H](O)[C@H](OC(=O)\C=C\c2ccc(O)c(OC)c2)[C@@H](C1)OC(=O)\C=C\c1ccc(O)c(O)c1
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 methyl 3,4-dicaffeoylquinate (CHEBI:85153) has functional parent (−)-quinic acid (CHEBI:17521)
methyl 3,4-dicaffeoylquinate (CHEBI:85153) has functional parent trans-caffeic acid (CHEBI:16433)
methyl 3,4-dicaffeoylquinate (CHEBI:85153) has role plant metabolite (CHEBI:76924)
methyl 3,4-dicaffeoylquinate (CHEBI:85153) is a alkyl caffeate ester (CHEBI:65331)
methyl 3,4-dicaffeoylquinate (CHEBI:85153) is a methyl ester (CHEBI:25248)
methyl 3,4-dicaffeoylquinate (CHEBI:85153) is a quinic acid (CHEBI:26493)
IUPAC Name
methyl (1R,3R,4S,5R)-3-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxy-4-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylate
Synonyms Sources
methyl 3-caffeoyl-4-feruloylquinate ChEBI
methyl 3-O-caffeoyl-4-O-feruloylquinate ChEBI
Manual Xref Database
HMDB0037093 HMDB
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Registry Number Type Source
21817159 Reaxys Registry Number Reaxys
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Last Modified
26 March 2020