1,4-NAPHTHOQUINONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C10H6O2
Molecular Weight	158.1538
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

c1ccc2c(c1)C(=O)C=CC2=O

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

Molecular Formula	C10H6O2
Molecular Weight	158.1538
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/24165164 | https://www.ncbi.nlm.nih.gov/pubmed/22218491 | https://www.ncbi.nlm.nih.gov/pubmed/19168278

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	Condition	Potency
DNA topoisomerase II alpha 34 Target ID: CHEMBL1806 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22218491	Inhibitor 7687	Cancer	10.8000000000000007 µM [IC50]
Monoamine oxidase B 66 Target ID: CHEMBL2039 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22071524	Inhibitor 7687		1.5 µM [Ki]
Monoamine oxidase A 48 Target ID: CHEMBL1951 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22071524	Inhibitor 7687		7.70000000000000018 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase
Alzheimer’s disease 261 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20709023	Primary		Basic research
Melanoma 81 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19121382	Primary		Basic research
Cancer 562 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19168278	Primary	DNA topoisomerase II alpha	Basic research

PubMed

Title	Date	PubMed
A new naphthoquinone from Pyrola japonica.	2001 Dec	11794527
Selective nonpeptidic inhibitors of herpes simplex virus type 1 and human cytomegalovirus proteases.	2001 Mar	11256477
Mutational analyses of cysteine residues of bovine dihydrodiol dehydrogenase 3.	2001 May 5	11343798
Irreversible photo-oxidation of propranolol triggered by self-photogenerated singlet molecular oxygen.	2002 Feb	12659130
Solubilization of a naphthoquinone derivative by hydroxypropyl-beta-cyclodextrin (HP-beta-CD) and polyvinylpyrrolidone (PVP-K30). The influence of PVP-K30 and pH on solubilizing effect of HP-beta-CD.	2002 Jan-Feb	12064060
Cellular pharmacology studies of shikonin derivatives.	2002 May	12164262
Synthesis of 2-alkoxy 1,4-naphthoquinone derivatives as antiplatelet, antiinflammatory, and antiallergic agents.	2002 May	12036028
Cyclooxygenase-2 inhibitory 1,4-naphthoquinones from Impatiens balsamina L.	2002 May	12033510
Why do co-solvents enhance the solubility of solutes in supercritical fluids? New evidence and opinion.	2002 Nov 15	12613028
Reactive quinones differentially regulate SAPK/JNK and p38/mHOG stress kinases.	2003 Feb	12626122
Kinetic and docking studies of the interaction of quinones with the quinone reductase active site.	2003 Feb 25	12590585
[Succivil efficacy in endogenous intoxication].	2003 Jul-Aug	14558355
Evidence for redox cycling of lawsone (2-hydroxy-1,4-naphthoquinone) in the presence of the hypoxanthine/xanthine oxidase system.	2003 Jul-Aug	12884402
A new approach to evaluating the extent of Michael adduct formation to PAH quinones: tetramethylammonium hydroxide (TMAH) thermochemolysis with GC/MS.	2003 Nov	14615976
Alternative quinone substrates and inhibitors of human electron-transfer flavoprotein-ubiquinone oxidoreductase.	2004 Mar 1	14640977

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

Substance Class	Chemical Created by `admin` on `Sat Jun 26 13:16:41 UTC 2021` Edited by `admin` on `Sat Jun 26 13:16:41 UTC 2021`
Record UNII	RBF5ZU7R7K
Record Status	`Validated (UNII)`
Record Version

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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

1,4-DIHYDRO-1,4-DIKETONAPHTHALENE

Systematic Name

English

NSC-9583

Code

English

1,4-NAPHTHALENEDIONE

Systematic Name

English

Code System Code Type Description

EPA CompTox

130-15-4