2-METHOXYNAPHTHOQUINONE

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

Structure Search

SMILES

COC1=CC(=O)C2=C(C=CC=C2)C1=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

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18914090 | https://www.ncbi.nlm.nih.gov/pubmed/22516543

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

Targets

Primary Target	Pharmacology	Condition	Potency
Wnt signaling pathway 13 Target ID: map04310 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20886301	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Breast cancer 434 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24291160	Palliative	Basic research	Unknown Approved Use Unknown
Gastric adenocarcinoma 12 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22516543	Primary	Basic research	Unknown Approved Use Unknown
Fungal infection 21 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18914090	Primary	Basic research	Unknown Approved Use Unknown
Helicobacter infection 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19773391	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Isolation of an antimicrobial compound from Impatiens balsamina L. using bioassay-guided fractionation.	2001 Dec	11746859
Discovery, total synthesis, HRV 3C-protease inhibitory activity, and structure-activity relationships of 2-methoxystypandrone and its analogues.	2001 Dec 17	11720861
Role of oxidant stress in lawsone-induced hemolytic anemia.	2004 Dec	15456924
Photoreactions of 1,4-Naphthoquinones: effects of substituents and water on the intermediates and reactivity.	2005 Mar-Apr	15560739
Effects of the compounds 2-methoxynaphthoquinone, 2-propoxynaphthoquinone, and 2-isopropoxynaphthoquinone on ecdysone 20-monooxygenase activity.	2007 Sep	17694563
Isolation and identification of an anti-tumor component from leaves of Impatiens balsamina.	2008 Jan 31	18305414
Naphthoquinones and anthraquinones from scent glands of a dyspnoid Harvestman, Paranemastoma quadripunctatum.	2010 Feb	20127150
Substituted naphthoquinones as novel amino acid sensitive reagents for the detection of latent fingermarks on paper surfaces.	2010 Oct 15	20875568
2-Methoxy-1,4-Naphthoquinone (MNQ) suppresses the invasion and migration of a human metastatic breast cancer cell line (MDA-MB-231).	2014 Apr	24291160

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

Antifungal activity of 2-methoxynaphthoquinone was tested by the cylinder plate method with agar medium. The LD50 value against Monilia fructicola was 3.1 ug/ml.

Name

Type

Language

2-METHOXYNAPHTHOQUINONE

Systematic Name

English

O-METHYLLAWSONE

Common Name

English

1,4-NAPHTHALENEDIONE, 2-METHOXY-

Systematic Name

English

1,4-NAPHTHOQUINONE, 2-METHOXY-

Systematic Name

English

NSC-31530

Code

English

LAWSONE METHYL ETHER

Common Name

English

2-METHOXY-1,4-NAPHTHOQUINONE

Systematic Name

English

Code System Code Type Description

PUBCHEM

16871