EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:85153 - methyl 3,4-dicaffeoylquinate

ChEBI IDCHEBI:85153
ChEBI Namemethyl 3,4-dicaffeoylquinate
Stars
DefinitionAn 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.
Last Modified26 March 2020
Submitternamrata
DownloadsMolfile
FormulaC27H28O12
Net Charge0
Average Mass544.509
Monoisotopic Mass544.15808
SMILESCOC(=O)[C@@]1(O)C[C@@H](O)[C@H](OC(=O)/C=C/c2ccc(O)c(OC)c2)[C@H](OC(=O)/C=C/c2ccc(O)c(O)c2)C1
InChIInChI=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
InChIKeyRTLCSWCXZWROFK-XKHJDCLGSA-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)
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  Source
methyl 3-caffeoyl-4-feruloylquinateChEBI
methyl 3-O-caffeoyl-4-O-feruloylquinateChEBI
Manual XrefsDatabases
HMDB0037093HMDB
Registry NumbersSources
Reaxys:21817159Reaxys
Citations