1,4-NAPHTHOQUINONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C10H6O2
Molecular Weight	158.1534
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

O=C1C=CC(=O)C2=C1C=CC=C2

InChI

InChIKey=FRASJONUBLZVQX-UHFFFAOYSA-N

InChI=1S/C10H6O2/c11-9-5-6-10(12)8-4-2-1-3-7(8)9/h1-6H

HIDE SMILES / InChI

Description

1,4-naphthoquinone is a chemical studied as a potential inhibitor of monoamine oxidase and DNA topoisomerase activities as well as acetyltransferase activity. 1,4-Naphthoquinone is a potent inhibitor of human cancer cell growth and angiogenesis.

Approval Year

Targets

Primary Target	Pharmacology	Potency
DNA topoisomerase II alpha 37	Inhibitor 8,297	10.8 µM [IC50]
Monoamine oxidase B 72	Inhibitor 8,297	1.5 µM [Ki]
Monoamine oxidase A 49	Inhibitor 8,297	7.7 µM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Alzheimer’s disease 272	Primary	Basic research	Unknown
Melanoma 88	Primary	Basic research	Unknown
Cancer 592	Primary	Basic research	Unknown

PubMed

Show entries

Title	Date	PubMed
[Cytotoxicity of beta-lapachone, an naphthoquinone with possible therapeutic use].	2001	11474885
Bromination studies of the 2,3-dimethylnaphthazarin core allowing easy access to naphthazarin derivatives.	2001 Aug 10	11485493
In vitro and in vivo Leishmanicidal activity of 2-hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthoquinone (lapachol).	2001 Feb	11180522
2- and 3-substituted 1,4-naphthoquinone derivatives as subversive substrates of trypanothione reductase and lipoamide dehydrogenase from Trypanosoma cruzi: synthesis and correlation between redox cycling activities and in vitro cytotoxicity.	2001 Feb 15	11170645
NAD(P)H:menadione oxidoreductase of the amitochondriate eukaryote Giardia lamblia: a simpler homologue of the vertebrate enzyme.	2001 Mar	11238963

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Patents

Sample Use Guides

In Vivo Use Guide

Rat LD50 (oral) 190mg/kg

Route of Administration: Oral

In Vitro Use Guide

1,4-naphthoquinone exhibited cytotoxic activity against HepG2 cell line with the IC50 value of 13.75±0.74 uM. It exhibited very potent ABTS+ cation radical scavenging activity with IC50 value of 7.97 uM.

Show entries

Name

Type

Language

1,4-NAPHTHOQUINONE

Systematic Name

English

1,4-NAPHTHOQUINONE [HSDB]

Common Name

English

NAPHTHOQUINONE, 1,4-

Systematic Name

English

1,4-NAPHTHOQUINONE [MI]

Common Name

English

.ALPHA.-NAPHTHOQUINONE

Common Name

English

Showing 1 to 5 of 8 entries

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Show entries

Code System

Code

Type

Description

EPA CompTox

DTXSID5040704

PRIMARY

PUBCHEM

8530

PRIMARY

HSDB

2037

PRIMARY

NSC

9583

PRIMARY

DAILYMED

RBF5ZU7R7K

PRIMARY

Showing 1 to 5 of 12 entries

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PARENT (METABOLITE)


					2166IN72UN

NAPHTHALENE

SUBSTANCE RECORD


					RBF5ZU7R7K

1,4-NAPHTHOQUINONE