| Stereochemistry | ACHIRAL |
| Molecular Formula | C19H18O8 |
| Molecular Weight | 374.3414 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC(=O)C1=C(O)C(C)=C(OC(=O)C2=C(O)C(C=O)=C(O)C=C2C)C=C1C
InChI
InChIKey=YLOYKYXNDHOHHT-UHFFFAOYSA-N
InChI=1S/C19H18O8/c1-8-5-12(21)11(7-20)17(23)15(8)19(25)27-13-6-9(2)14(18(24)26-4)16(22)10(13)3/h5-7,21-23H,1-4H3
| Molecular Formula | C19H18O8 |
| Molecular Weight | 374.3414 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Atranorin is the main compound of the lichen Cladina kalbii Ahti, which grows in the arid regions of northeastern Brazil. Atranorin possesses anticancer activity, experiments in vitro and in vivo have shown, that it may inhibit lung cancer cell motility and tumorigenesis by affecting AP-1, Wnt, and STAT signaling and suppressing RhoGTPase activity. In addition, experiments on animal have revealed, that Atranorin might be an important tool in the management and/or treatment of inflammatory disorders.
Approval Year
PubMed
Patents
Sample Use Guides
Xenograft mouse model: atranorin (10 mg/kg) mixed with 20% DMSO every 3 days by intraperitoneal injection for 2 weeks.
Anti-inflammatory study: acute hind paw edema was induced in male rats by injecting 0.1 mL of carrageenan into the subplantar region of the right hind paw. Atranorin (ATR) (50, 100, and 200 mg/kg, p.o.) was administered to three different groups, while two other groups served as negative and positive controls and received vehicle (0.9% saline with two drops of 0.2% Tween 80, a solvent for ATR) and standard drug (aspirin, 300 mg/kg, p.o.), respectively. ATR and aspirin were administered 1 h prior to the injection of carrageenan.
Route of Administration:
Other
The inhibitory activity of atranorin (5 μg/mL) in additional lung cancer cell lines was examined by performing invasion assays in H460, H1650, H1975, and LLC cells. Atranorin treatment significantly decreased the number of invaded H460, H1650, H1975, and LLC cells. Quantitative analysis showed that atranorin inhibited invasion by 50%, 24%, 30%, and 80% in H460, H1650, H1975, and LLC cells, respectively, compared with vehicle-treated cells.