| Stereochemistry | ABSOLUTE |
| Molecular Formula | C16H16O8 |
| Molecular Weight | 336.2934 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O[C@@H]1C=C(C[C@@H](OC(=O)\C=C\C2=CC=C(O)C(O)=C2)[C@@H]1O)C(O)=O
InChI
InChIKey=QMPHZIPNNJOWQI-GDDAOPKQSA-N
InChI=1S/C16H16O8/c17-10-3-1-8(5-11(10)18)2-4-14(20)24-13-7-9(16(22)23)6-12(19)15(13)21/h1-6,12-13,15,17-19,21H,7H2,(H,22,23)/b4-2+/t12-,13-,15-/m1/s1
5-O-Caffeoylshikimic acid is a characteristic phenolic compound mainly found in the Palmae family. 5-O-Caffeoylshikimic acid was isolated from such plants as Vaccinium corymbosum, Livistona chinensis to name a few. The drug demonstrated the antiproliferative activity against different cancer cell lines. 5-O-Caffeoylshikimic acid could promote cancer cell apoptosis and block cancer cell adhesion, invasion and migration by inhibiting transforming growth factor beta 1 (TGF-beta1) signaling pathway.
Approval Year
PubMed
Sample Use Guides
In a macrophages migration and adhesion assay, HUVEC were cultured in DMEM supplemented with 10% FBS, 1% penicillin-streptomycin, at 37C in a 5% CO2 incubator. Then HUVEC were seeded on the coverslips in 24-well plates at 80–90% confluence, starved and incubated with 5-O-Caffeoylshikimic acid (5 uM; 500 nM; 50 nM) + advanced glycation end-products (200 ug/mL) for 24 h.
SUBSTANCE RECORD
