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

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

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

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:07:29 GMT 2023` Edited by `admin` on `Fri Dec 15 15:07:29 GMT 2023`
Record UNII	39020BUT1D
Record Status	`Validated (UNII)`
Record Version

Download

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