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

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ChEBI Name 3,4,5-tricaffeoylquinic acid
ChEBI ID CHEBI:233498
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information No supplier information found for this compound.
Download Molfile XML SDF
Formula C34H30O15
Net Charge 0
Average Mass 678.599
Monoisotopic Mass 678.15847
InChI InChI=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
InChIKey OAFXTKGAKYAFSI-UPHZGLEOSA-N
SMILES [H]C(=CC1=CC=C(O)C(O)=C1)C(=O)OC2CC(O)(C(=O)O)CC(OC(=O)C([H])=CC3=CC=C(O)C(O)=C3)C2OC(=O)C([H])=CC4=CC=C(O)C(O)=C4
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): anti-HIV agent
An antiviral agent that destroys or inhibits the replication of the human immunodeficiency virus.
antiviral agent
A substance that destroys or inhibits replication of viruses.
Application(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 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 Sources
3,4,5-TCQA ChEBI
3,4,5-tri-O-caffeoylquinic acid ChEBI
3,4,5-triCQA ChEBI
Citations Waiting for Citations
Last Modified
13 February 2025