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

Structure Search

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

Molecular Formula	C10H6O2
Molecular Weight	158.1534
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	Potency
DNA topoisomerase II alpha 37 Target ID: CHEMBL1806 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22218491	Inhibitor 8297	10.8 µM [IC50]
Monoamine oxidase B 72 Target ID: CHEMBL2039 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22071524	Inhibitor 8297	1.5 µM [Ki]
Monoamine oxidase A 49 Target ID: CHEMBL1951 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22071524	Inhibitor 8297	7.7 µM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Alzheimer’s disease 272 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20709023	Primary	Basic research	Unknown Approved Use Unknown
Melanoma 88 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19121382	Primary	Basic research	Unknown Approved Use Unknown
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19168278	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Molecular modeling and 3D-QSAR studies in 2-aziridinyl-and 2,3-bis(aziridinyl)-1,4-naphthoquinonyl sulfonate and acylate derivatives as potential antimalarial agents.	2001	11813805
[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
A new naphthoquinone from Pyrola japonica.	2001 Dec	11794527
Association of quinone-induced platelet anti-aggregation with cytotoxicity.	2001 Jul	11399805
Quinone isomers of the WS-5995 antibiotics: synthetic antitumor agents that inhibit macromolecule synthesis, block nucleoside transport, induce DNA fragmentation, and decrease the growth and viability of L1210 leukemic cells more effectively than ellagic acid and genistein in vitro.	2001 Jun	11395569
Recruitment of a foreign quinone into the A1 site of photosystem I. In vivo replacement of plastoquinone-9 by media-supplemented naphthoquinones in phylloquinone biosynthetic pathway mutants of Synechocystis sp. PCC 6803.	2001 Oct 26	11470786
Inactivation of rat cytochrome P450 2D enzyme by a further metabolite of 4-hydroxypropranolol, the major and active metabolite of propranolol.	2001 Sep	11558582
[Studies on the inhibition of polyhydroxylated aromatic compounds against HIV-1 integrase].	2002 Apr	12579818
A new naphthoquinone from Polygonum aviculare.	2002 Apr	11990427
Lindbladione and related naphthoquinone pigments from a myxomycete Lindbladia tubulina.	2002 Aug	12192152
Chloroquinocin, a novel chlorinated naphthoquinone antibiotic from Streptomyces sp., LL-A9227.	2002 Dec	12617517
2-(Pyrrolidin-1-yl)-1,4-naphthoquinone and 2-phenylsulfanyl-3-(pyrrolidin-1-yl)-1,4-naphthoquinone.	2002 Dec	12466620
Placement and characterization of pairs of luminescent molecules in spatially separated regions of nanostructured thin films.	2002 Dec 4	12452713
Geranyl diphosphate:4-hydroxybenzoate geranyltransferase from Lithospermum erythrorhizon. Cloning and characterization of a ket enzyme in shikonin biosynthesis.	2002 Feb 22	11744717
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
[Respiratory activity and naphthoquinone synthesis in the fungus Fusarium decemcellulare exposed to oxidative stress].	2002 Mar-Apr	12024815
Synthesis of 2-alkoxy 1,4-naphthoquinone derivatives as antiplatelet, antiinflammatory, and antiallergic agents.	2002 May	12036028
Three new naphthoquinone derivatives from Diospyros maritima Blume.	2002 May	12036010
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
Synthesis of monocarbenepalladium(0) complexes and their catalytic behavior in cross-coupling reactions of aryldiazonium salts.	2002 Sep 2	12360931
Feasibility of atmospheric pressure desorption/ionization on silicon mass spectrometry in analysis of drugs.	2003	12811757
Mechanisms for naphthalene removal during electrolytic aeration.	2003 Feb	12531271
Synthesis and biological evaluation of some new substituted naphthoquinones.	2003 Jun	14526658
Discriminating redox cycling and arylation pathways of reactive chemical toxicity in trout hepatocytes.	2003 Mar	12604835
Total syntheses of furaquinocin A, B, and E.	2003 Oct 29	14570490
Cytotoxicity and DNA topoisomerase inhibitory activity of benz[f]indole-4,9-dione analogs.	2003 Sep	14519980
A new naphthoquinone from Ceiba pentandra.	2003 Sep	12931857
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 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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:02:36 GMT 2023` Edited by `admin` on `Fri Dec 15 19:02:36 GMT 2023`
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

DTXSID5040704