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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 of 1,4-NAPHTHOQUINONE

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

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

Targets

Primary TargetPharmacologyConditionPotency
10.8 µM [IC50]
1.5 µM [Ki]
7.7 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
[Cytotoxicity of beta-lapachone, an naphthoquinone with possible therapeutic use].
2001
Concerted action of DT-diaphorase and superoxide dismutase in preventing redox cycling of naphthoquinones: an evaluation.
2001 Aug
Selective nonpeptidic inhibitors of herpes simplex virus type 1 and human cytomegalovirus proteases.
2001 Mar
Mutational analyses of cysteine residues of bovine dihydrodiol dehydrogenase 3.
2001 May 5
Interaction of camel lens zeta-crystallin with quinones: portrait of a substrate by fluorescence spectroscopy.
2001 Nov 15
Abiotic transformation of catechol and 1-naphthol in aqueous solution-influence of environmental factors.
2001 Oct
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
A new naphthoquinone from Polygonum aviculare.
2002 Apr
Geranyl diphosphate:4-hydroxybenzoate geranyltransferase from Lithospermum erythrorhizon. Cloning and characterization of a ket enzyme in shikonin biosynthesis.
2002 Feb 22
Antipruritic effects of 1,4-naphthoquinones and related compounds.
2002 Jan
Direct reaction between shikonin and thiols induces apoptosis in HL60 cells.
2002 Jul
[Synthesis of triads based on deuteroporphyrin IX, naphthoquinone, and aromatic amino acids].
2002 Jul-Aug
Naphthoquinone cataract in mice: mitochondrial change and protection by superoxide dismutase.
2002 Jun
Acute lethal toxicity of environmental pollutants to aquatic organisms.
2002 Jun
Inhibitory effects of quinones on RNase H activity associated with HIV-1 reverse transcriptase.
2002 Mar
The anatomy and chemistry of the colour bands of grasstree stems (Xanthorrhoea preissii) used for plant age and fire history determination.
2002 May
Synthesis of 2-alkoxy 1,4-naphthoquinone derivatives as antiplatelet, antiinflammatory, and antiallergic agents.
2002 May
Three new naphthoquinone derivatives from Diospyros maritima Blume.
2002 May
In vitro antifungal activity of naphthoquinone derivatives.
2002 May
Why do co-solvents enhance the solubility of solutes in supercritical fluids? New evidence and opinion.
2002 Nov 15
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
Magneto-switchable electrocatalytic and bioelectrocatalytic transformations.
2002 Sep 16
Synthesis of monocarbenepalladium(0) complexes and their catalytic behavior in cross-coupling reactions of aryldiazonium salts.
2002 Sep 2
The prolyl isomerase Pin1 in breast development and cancer.
2003
Protein targets of 1,4-benzoquinone and 1,4-naphthoquinone in human bronchial epithelial cells.
2003 Apr
1-Methyl anthraquinones and their biogenetic precursors from Stereospermum personatum.
2003 Aug
Involvement of Akt in mitochondria-dependent apoptosis induced by a cdc25 phosphatase inhibitor naphthoquinone analog.
2003 Dec 4
Reactive quinones differentially regulate SAPK/JNK and p38/mHOG stress kinases.
2003 Feb
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
Effects of hydroxypropyl-beta-cyclodextrin on the chemical stability of a naphthoquinone in aqueous solutions.
2003 Jan
Dihydrolindbladiones, three new naphthoquinone pigments from a myxomycete Lindbladia tubulina.
2003 Jul
Perspective in antimalarial chemotherapy.
2003 Jul
[Succivil efficacy in endogenous intoxication].
2003 Jul-Aug
Evidence for redox cycling of lawsone (2-hydroxy-1,4-naphthoquinone) in the presence of the hypoxanthine/xanthine oxidase system.
2003 Jul-Aug
Synthesis and biological evaluation of some new substituted naphthoquinones.
2003 Jun
DNA topoisomerases I and II inhibitory activity of constituents isolated from Juglans mandshurica.
2003 Jun
In vitro cytotoxicity activity of Diosquinone, a naphthoquinone epoxide.
2003 Mar
Isodiospyrin as a novel human DNA topoisomerase I inhibitor.
2003 Nov 15
Total syntheses of furaquinocin A, B, and E.
2003 Oct 29
A new naphthoquinone from Ceiba pentandra.
2003 Sep
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Rat LD50 (oral) 190mg/kg Mouse LD50 (intraperitoneal) 5500µg/kg Guinea Pig LD50 (oral) 400mg/kg
Rat LD50 (oral) 190mg/kg
Route of Administration: Oral
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 Thu Jul 06 02:11:49 UTC 2023
Edited
by admin
on Thu Jul 06 02:11:49 UTC 2023
Record UNII
RBF5ZU7R7K
Record Status Validated (UNII)
Record Version
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Name Type Language
1,4-NAPHTHOQUINONE
HSDB   MI  
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
Created by admin on Thu Jul 06 02:11:50 UTC 2023 , Edited by admin on Thu Jul 06 02:11:50 UTC 2023
PRIMARY
PUBCHEM
8530
Created by admin on Thu Jul 06 02:11:50 UTC 2023 , Edited by admin on Thu Jul 06 02:11:50 UTC 2023
PRIMARY
HSDB
2037
Created by admin on Thu Jul 06 02:11:50 UTC 2023 , Edited by admin on Thu Jul 06 02:11:50 UTC 2023
PRIMARY
NSC
9583
Created by admin on Thu Jul 06 02:11:50 UTC 2023 , Edited by admin on Thu Jul 06 02:11:50 UTC 2023
PRIMARY
DAILYMED
RBF5ZU7R7K
Created by admin on Thu Jul 06 02:11:50 UTC 2023 , Edited by admin on Thu Jul 06 02:11:50 UTC 2023
PRIMARY
ECHA (EC/EINECS)
204-977-6
Created by admin on Thu Jul 06 02:11:50 UTC 2023 , Edited by admin on Thu Jul 06 02:11:50 UTC 2023
PRIMARY
FDA UNII
RBF5ZU7R7K
Created by admin on Thu Jul 06 02:11:50 UTC 2023 , Edited by admin on Thu Jul 06 02:11:50 UTC 2023
PRIMARY
CHEBI
27418
Created by admin on Thu Jul 06 02:11:50 UTC 2023 , Edited by admin on Thu Jul 06 02:11:50 UTC 2023
PRIMARY
RXCUI
1602556
Created by admin on Thu Jul 06 02:11:50 UTC 2023 , Edited by admin on Thu Jul 06 02:11:50 UTC 2023
PRIMARY RxNorm
MERCK INDEX
M7750
Created by admin on Thu Jul 06 02:11:50 UTC 2023 , Edited by admin on Thu Jul 06 02:11:50 UTC 2023
PRIMARY Merck Index
WIKIPEDIA
1,4-NAPHTHOQUINONE
Created by admin on Thu Jul 06 02:11:50 UTC 2023 , Edited by admin on Thu Jul 06 02:11:50 UTC 2023
PRIMARY
CAS
130-15-4
Created by admin on Thu Jul 06 02:11:50 UTC 2023 , Edited by admin on Thu Jul 06 02:11:50 UTC 2023
PRIMARY
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