U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C25H24O12
Molecular Weight 516.4509
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of 3,5-DI-O-CAFFEOYLQUINIC ACID

SMILES

O[C@H]1[C@@H](C[C@@](O)(C[C@H]1OC(=O)\C=C\C2=CC(O)=C(O)C=C2)C(O)=O)OC(=O)\C=C\C3=CC(O)=C(O)C=C3

InChI

InChIKey=KRZBCHWVBQOTNZ-PSEXTPKNSA-N
InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(30)36-19-11-25(35,24(33)34)12-20(23(19)32)37-22(31)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-29,32,35H,11-12H2,(H,33,34)/b7-3+,8-4+/t19-,20-,23-,25+/m1/s1

HIDE SMILES / InChI

Description

3,5-Dicaffeoylquinic acid is an active component naturally occurring in many plants such as Helichrysum populifolium, Ipomoea batatas, Centella asiatica, Aster scaber and green coffee beans to name a few. It is a selective inhibitor of human immunodeficiency virus type 1 integrase and can be a promising agent for the treatment of patients with HIV infection.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.66 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
In a preclinical model of Alzheimer’s disease, mice were orally administered with 3,5-dicaffeoylquinic acid mixed with drinking water (6.7 mg/kg/day) for 1 month using oral administration tube and syringe.
Route of Administration: Oral
In Vitro Use Guide
In a viability assay, SH-SY5Y cells were treated with 3,5-dicaffeoylquinic acid (20 uM) and exposed to 2 uM Abeta1-42 for 72 h. The drug was shown to protect the cells from death and the cell viability significantly increased to 106.5%.