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=CC=CC=C12

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 8504	10.8 µM [IC50]
Monoamine oxidase B 75 Target ID: CHEMBL2039 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22071524	Inhibitor 8504	1.5 µM [Ki]
Monoamine oxidase A 52 Target ID: CHEMBL1951 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22071524	Inhibitor 8504	7.7 µM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Alzheimer’s disease 278 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 609 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19168278	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Thermal analysis and spectroscopic characterization of interactions between a naphthoquinone derivative with HP-beta-CD or PVP.	2002	12229269
[Studies on the inhibition of polyhydroxylated aromatic compounds against HIV-1 integrase].	2002 Apr	12579818
High level expression of chorismate pyruvate-lyase (UbiC) and HMG-CoA reductase in hairy root cultures of Lithospermum erythrorhizon.	2002 Aug	12198192
Lindbladione and related naphthoquinone pigments from a myxomycete Lindbladia tubulina.	2002 Aug	12192152
Stability of hemoglobin and albumin adducts of naphthalene oxide, 1,2-naphthoquinone, and 1,4-naphthoquinone.	2002 Aug	12151627
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
Stimulatory effect of menaquinone-7 on bone formation in elderly female rat femoral tissues in vitro: prevention of bone deterioration with aging.	2002 Dec	12429999
K vitamins, PTP antagonism, and cell growth arrest.	2002 Dec	12384979
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
Direct reaction between shikonin and thiols induces apoptosis in HL60 cells.	2002 Jul	12132652
In vitro antimicrobial activity of a new series of 1,4-naphthoquinones.	2002 Jul	12131921
Induction of p73beta by a naphthoquinone analog is mediated by E2F-1 and triggers apoptosis in HeLa cells.	2002 Jul 3	12095638
[Synthesis of triads based on deuteroporphyrin IX, naphthoquinone, and aromatic amino acids].	2002 Jul-Aug	12197394
Naphthoquinone cataract in mice: mitochondrial change and protection by superoxide dismutase.	2002 Jun	12099544
Cellular pharmacology studies of shikonin derivatives.	2002 May	12164262
The anatomy and chemistry of the colour bands of grasstree stems (Xanthorrhoea preissii) used for plant age and fire history determination.	2002 May	12099535
Protective effect of aloe extract against the cytotoxicity of 1,4-naphthoquinone in isolated rat hepatocytes involves modulations in cellular thiol levels.	2002 May	12076309
Why do co-solvents enhance the solubility of solutes in supercritical fluids? New evidence and opinion.	2002 Nov 15	12613028
Fetal growth in rats treated with lapachol.	2002 Oct	12413627
DYKAT of Baylis-Hillman adducts: concise total synthesis of furaquinocin E.	2002 Oct 2	12296725
Measurement of hemoglobin and albumin adducts of naphthalene-1,2-oxide, 1,2-naphthoquinone and 1,4-naphthoquinone after administration of naphthalene to F344 rats.	2002 Oct 20	12385719
Cancer therapy with beta-lapachone.	2002 Sep	12188909
Magneto-switchable electrocatalytic and bioelectrocatalytic transformations.	2002 Sep 16	12298004
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
Protein targets of 1,4-benzoquinone and 1,4-naphthoquinone in human bronchial epithelial cells.	2003 Apr	12687615
1-Methyl anthraquinones and their biogenetic precursors from Stereospermum personatum.	2003 Aug	12895541
Involvement of Akt in mitochondria-dependent apoptosis induced by a cdc25 phosphatase inhibitor naphthoquinone analog.	2003 Dec 4	14644418
Kinetic and docking studies of the interaction of quinones with the quinone reductase active site.	2003 Feb 25	12590585
New strategies and building blocks for functionalised 9,10-bis(1,3-dithiol-2-ylidene)-9,10-dihydroanthracene derivatives, including pyrrolo-annelated derivatives and pi-extended systems with intramolecular charge-transfer.	2003 Feb 7	12926254
Effects of hydroxypropyl-beta-cyclodextrin on the chemical stability of a naphthoquinone in aqueous solutions.	2003 Jan	12622250
Dihydrolindbladiones, three new naphthoquinone pigments from a myxomycete Lindbladia tubulina.	2003 Jul	12880324
Perspective in antimalarial chemotherapy.	2003 Jul	12678807
[Succivil efficacy in endogenous intoxication].	2003 Jul-Aug	14558355
Naphthoquinone derivatives and lignans from the Paraguayan crude drug "tayï pytá" (Tabebuia heptaphylla, Bignoniaceae).	2003 Jul-Aug	12939034
Evidence for redox cycling of lawsone (2-hydroxy-1,4-naphthoquinone) in the presence of the hypoxanthine/xanthine oxidase system.	2003 Jul-Aug	12884402
Synthesis and biological evaluation of some new substituted naphthoquinones.	2003 Jun	14526658
DNA topoisomerases I and II inhibitory activity of constituents isolated from Juglans mandshurica.	2003 Jun	12877556
Metal ion-promoted intramolecular electron transfer in a ferrocene-naphthoquinone linked dyad. Continuous change in driving force and reorganization energy with metal ion concentration.	2003 Jun 11	12783556
Discriminating redox cycling and arylation pathways of reactive chemical toxicity in trout hepatocytes.	2003 Mar	12604835
A new approach to evaluating the extent of Michael adduct formation to PAH quinones: tetramethylammonium hydroxide (TMAH) thermochemolysis with GC/MS.	2003 Nov	14615976
Isodiospyrin as a novel human DNA topoisomerase I inhibitor.	2003 Nov 15	14599556
Phototransformation of 1,4-naphthoquinone in aqueous solution.	2003 Oct	14606760
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
The naphthoquinol oxidizing cytochrome bc1 complex of the hyperthermophilic knallgasbacterium Aquifex aeolicus: properties and phylogenetic relationships.	2003 Sep 16	12962505
Total synthesis of 12-methoxydihydrochelerythrine and anti-tumour activity of its quaternary base: toward an efficient synthetic route for 12-alkoxybenzo[c]phenanthridine bases via naphthoquinone monooxime from 2-benzofuranyl-1-tetralone derivative.	2003 Sep 7	14518124
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 `Mon Mar 31 19:31:21 GMT 2025` Edited by `admin` on `Mon Mar 31 19:31:21 GMT 2025`
Record UNII	RBF5ZU7R7K
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-9583

Preferred Name

English

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

1,4-NAPHTHALENEDIONE

Systematic Name

English

Code System Code Type Description

EPA CompTox

DTXSID5040704