Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C11H8O3 |
| Molecular Weight | 188.1794 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC(=O)C2=CC=CC=C2C1=O
InChI
InChIKey=OBGBGHKYJAOXRR-UHFFFAOYSA-N
InChI=1S/C11H8O3/c1-14-10-6-9(12)7-4-2-3-5-8(7)11(10)13/h2-6H,1H3
| Molecular Formula | C11H8O3 |
| Molecular Weight | 188.1794 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
2-Methoxynaphthoquinone is a naturally occurring naphthalene derivative, first synthesized by L. Fieser in 1926, and afterward found in Impatiens balsamina (garden balsam). 2-Methoxynaphthoquinone possess antifungal activity. In vitro studies showed that compound inhibits Wnt signaling and suppresses the invasion of breast cancer cell lines, and is able to induce gastric adenocarcinoma necrosis.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| 2-Methoxy-1,4-Naphthoquinone (MNQ) suppresses the invasion and migration of a human metastatic breast cancer cell line (MDA-MB-231). | 2014-04 |
|
| Substituted naphthoquinones as novel amino acid sensitive reagents for the detection of latent fingermarks on paper surfaces. | 2010-10-15 |
|
| Naphthoquinones and anthraquinones from scent glands of a dyspnoid Harvestman, Paranemastoma quadripunctatum. | 2010-02 |
|
| Isolation and identification of an anti-tumor component from leaves of Impatiens balsamina. | 2008-01-31 |
|
| Effects of the compounds 2-methoxynaphthoquinone, 2-propoxynaphthoquinone, and 2-isopropoxynaphthoquinone on ecdysone 20-monooxygenase activity. | 2007-09 |
|
| Role of oxidant stress in lawsone-induced hemolytic anemia. | 2004-12 |
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| Photoreactions of 1,4-Naphthoquinones: effects of substituents and water on the intermediates and reactivity. | 2004-11-25 |
|
| Discovery, total synthesis, HRV 3C-protease inhibitory activity, and structure-activity relationships of 2-methoxystypandrone and its analogues. | 2001-12-17 |
|
| Isolation of an antimicrobial compound from Impatiens balsamina L. using bioassay-guided fractionation. | 2001-12 |
Patents
Sample Use Guides
In a toxicology study in rats, daily feeding with 0.35 mg/kg 2-methoxynaphthoquinone produced a marked fall of the erythrocyte count and hemoglobin.
Route of Administration:
Oral
| Substance Class |
Chemical
Created
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