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CHEBI:233498 - 3,4,5-tricaffeoylquinic acid

ChEBI IDCHEBI:233498
ChEBI Name3,4,5-tricaffeoylquinic acid
Stars
DefinitionA carboxylic ester that is the triester obtained by the condensation of the hydroxy groups at positions 3, 4, and 5 of (−)-quinic acid with the carboxy group of caffeic acid.
Last Modified13 February 2025
SubmitterAdnan
DownloadsMolfile
FormulaC34H30O15
Net Charge0
Average Mass678.599
Monoisotopic Mass678.15847
SMILES[H]C(=Cc1ccc(O)c(O)c1)C(=O)O[C@@H]1C[C@](O)(C(=O)O)C[C@@H](OC(=O)C([H])=Cc2ccc(O)c(O)c2)[C@H]1OC(=O)C([H])=Cc1ccc(O)c(O)c1
InChIInChI=1S/C34H30O15/c35-21-7-1-18(13-24(21)38)4-10-29(41)47-27-16-34(46,33(44)45)17-28(48-30(42)11-5-19-2-8-22(36)25(39)14-19)32(27)49-31(43)12-6-20-3-9-23(37)26(40)15-20/h1-15,27-28,32,35-40,46H,16-17H2,(H,44,45)/t27-,28-,32-,34+/m1/s1
InChIKeyOAFXTKGAKYAFSI-UPHZGLEOSA-N
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
antiviral agent  A substance that destroys or inhibits replication of viruses.
anti-HIV agent  An antiviral agent that destroys or inhibits the replication of the human immunodeficiency virus.
Applications:
nootropic agent  Any compound that improves mental functions such as cognition, memory, intelligence, motivation, attention, and concentration.
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
ChEBI Ontology
Outgoing Relation(s)
3,4,5-tricaffeoylquinic acid (CHEBI:233498) has functional parent (−)-quinic acid (CHEBI:17521)
3,4,5-tricaffeoylquinic acid (CHEBI:233498) has functional parent caffeic acid (CHEBI:36281)
3,4,5-tricaffeoylquinic acid (CHEBI:233498) has role anti-HIV agent (CHEBI:64946)
3,4,5-tricaffeoylquinic acid (CHEBI:233498) has role anti-inflammatory agent (CHEBI:67079)
3,4,5-tricaffeoylquinic acid (CHEBI:233498) has role antiviral agent (CHEBI:22587)
3,4,5-tricaffeoylquinic acid (CHEBI:233498) has role nootropic agent (CHEBI:66980)
3,4,5-tricaffeoylquinic acid (CHEBI:233498) is a catechols (CHEBI:33566)
3,4,5-tricaffeoylquinic acid (CHEBI:233498) is a cinnamate ester (CHEBI:36087)
3,4,5-tricaffeoylquinic acid (CHEBI:233498) is a cyclitol carboxylic acid (CHEBI:36123)
Incoming Relation(s)
3,4,5-tri-(E)-caffeoylquinic acid (CHEBI:233499) is a 3,4,5-tricaffeoylquinic acid (CHEBI:233498)
IUPAC Name 
(1S,3R,4S,5R)-3,4,5-tris{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1-hydroxycyclohexanecarboxylic acid
Synonyms  Source
3,4,5-triCQAChEBI
3,4,5-TCQAChEBI
3,4,5-tri-O-caffeoylquinic acidChEBI
Citations