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
A novel dark-inducible protein, LeDI-2, and its involvement in root-specific secondary metabolism in Lithospermum erythrorhizon.	2001 Apr	11299363
New selective cytotoxic diterpenylquinones and diterpenylhydroquinones.	2001 Apr 12	11312925
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
Discovery, total synthesis, HRV 3C-protease inhibitory activity, and structure-activity relationships of 2-methoxystypandrone and its analogues.	2001 Dec 17	11720861
Synthesis and biological studies of novel nucleoside phosphoramidate prodrugs.	2001 Dec 6	11728193
Association of quinone-induced platelet anti-aggregation with cytotoxicity.	2001 Jul	11399805
Caspase-3-mediated cleavage of the NF-kappa B subunit p65 at the NH2 terminus potentiates naphthoquinone analog-induced apoptosis.	2001 Jul 6	11320092
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
Mutational analyses of cysteine residues of bovine dihydrodiol dehydrogenase 3.	2001 May 5	11343798
Combinatorial screening of heterogeneous catalysis in selective oxidation of naphthalene by laser-induced fluorescence imaging.	2001 Sep 15	11575790
[Studies on the inhibition of polyhydroxylated aromatic compounds against HIV-1 integrase].	2002 Apr	12579818
A new naphthoquinone from Polygonum aviculare.	2002 Apr	11990427
Identification of a potent and selective pharmacophore for Cdc25 dual specificity phosphatase inhibitors.	2002 Apr	11901209
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
Placement and characterization of pairs of luminescent molecules in spatially separated regions of nanostructured thin films.	2002 Dec 4	12452713
Exploring the primary electron acceptor (QA)-site of the bacterial reaction center from Rhodobacter sphaeroides. Binding mode of vitamin K derivatives.	2002 Feb	11856340
Antipruritic effects of 1,4-naphthoquinones and related compounds.	2002 Jan	11824545
Inhibition of Ca2+-activated and voltage-dependent K+ currents by 2-mercaptophenyl-1,4-naphthoquinone in pituitary GH3 cells: contribution to its antiproliferative effect.	2002 Jan 25	11848302
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
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
Naphthoquinone cataract in mice: mitochondrial change and protection by superoxide dismutase.	2002 Jun	12099544
Acute lethal toxicity of environmental pollutants to aquatic organisms.	2002 Jun	12061826
The function of photosystem I. Quantum chemical insight into the role of tryptophan-quinone interactions.	2002 Mar 5	11863427
[Respiratory activity and naphthoquinone synthesis in the fungus Fusarium decemcellulare exposed to oxidative stress].	2002 Mar-Apr	12024815
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
Fetal growth in rats treated with lapachol.	2002 Oct	12413627
The prolyl isomerase Pin1 in breast development and cancer.	2003	12631385
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
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
DNA topoisomerases I and II inhibitory activity of constituents isolated from Juglans mandshurica.	2003 Jun	12877556
Suzuki-Miyaura homocoupling of naphthyl triflates using bis(pinacolato)diboron: approaches to the biaryl skeleton of crisamicin A.	2003 Jun 21	12945899
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
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