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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=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

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

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
 10.8 µM [IC50]
Inhibitor
8504
 1.5 µM [Ki]
Inhibitor
8504
 7.7 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Basic research
Unknown

Approved Use

Unknown
Primary
Basic research
Unknown

Approved Use

Unknown
Primary
Basic research
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Alternative quinone substrates and inhibitors of human electron-transfer flavoprotein-ubiquinone oxidoreductase.
2004-03-01
Involvement of Akt in mitochondria-dependent apoptosis induced by a cdc25 phosphatase inhibitor naphthoquinone analog.
2003-12-04
Isodiospyrin as a novel human DNA topoisomerase I inhibitor.
2003-11-15
A new approach to evaluating the extent of Michael adduct formation to PAH quinones: tetramethylammonium hydroxide (TMAH) thermochemolysis with GC/MS.
2003-11
Total syntheses of furaquinocin A, B, and E.
2003-10-29
[Succivil efficacy in endogenous intoxication].
2003-10-16
Phototransformation of 1,4-naphthoquinone in aqueous solution.
2003-10
The naphthoquinol oxidizing cytochrome bc1 complex of the hyperthermophilic knallgasbacterium Aquifex aeolicus: properties and phylogenetic relationships.
2003-09-16
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.
2003-09-07
Cytotoxicity and DNA topoisomerase inhibitory activity of benz[f]indole-4,9-dione analogs.
2003-09
A new naphthoquinone from Ceiba pentandra.
2003-09
Naphthoquinone derivatives and lignans from the Paraguayan crude drug "tayï pytá" (Tabebuia heptaphylla, Bignoniaceae).
2003-08-27
1-Methyl anthraquinones and their biogenetic precursors from Stereospermum personatum.
2003-08
Evidence for redox cycling of lawsone (2-hydroxy-1,4-naphthoquinone) in the presence of the hypoxanthine/xanthine oxidase system.
2003-07-29
Dihydrolindbladiones, three new naphthoquinone pigments from a myxomycete Lindbladia tubulina.
2003-07
Perspective in antimalarial chemotherapy.
2003-07
Suzuki-Miyaura homocoupling of naphthyl triflates using bis(pinacolato)diboron: approaches to the biaryl skeleton of crisamicin A.
2003-06-21
Activity of quinones on colletotrichum species.
2003-06-18
Metal ion-promoted intramolecular electron transfer in a ferrocene-naphthoquinone linked dyad. Continuous change in driving force and reorganization energy with metal ion concentration.
2003-06-11
Synthesis and biological evaluation of some new substituted naphthoquinones.
2003-06
DNA topoisomerases I and II inhibitory activity of constituents isolated from Juglans mandshurica.
2003-06
Effects of a naphthoquinone analog on tumor growth and apoptosis induction.
2003-05
Protein targets of 1,4-benzoquinone and 1,4-naphthoquinone in human bronchial epithelial cells.
2003-04
In vitro cytotoxicity activity of Diosquinone, a naphthoquinone epoxide.
2003-03
Discriminating redox cycling and arylation pathways of reactive chemical toxicity in trout hepatocytes.
2003-03
Kinetic and docking studies of the interaction of quinones with the quinone reductase active site.
2003-02-25
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.
2003-02-07
Reactive quinones differentially regulate SAPK/JNK and p38/mHOG stress kinases.
2003-02
Mechanisms for naphthalene removal during electrolytic aeration.
2003-02
Effects of hydroxypropyl-beta-cyclodextrin on the chemical stability of a naphthoquinone in aqueous solutions.
2003-01
Feasibility of atmospheric pressure desorption/ionization on silicon mass spectrometry in analysis of drugs.
2003
The prolyl isomerase Pin1 in breast development and cancer.
2003
Placement and characterization of pairs of luminescent molecules in spatially separated regions of nanostructured thin films.
2002-12-04
Chloroquinocin, a novel chlorinated naphthoquinone antibiotic from Streptomyces sp., LL-A9227.
2002-12
2-(Pyrrolidin-1-yl)-1,4-naphthoquinone and 2-phenylsulfanyl-3-(pyrrolidin-1-yl)-1,4-naphthoquinone.
2002-12
Stimulatory effect of menaquinone-7 on bone formation in elderly female rat femoral tissues in vitro: prevention of bone deterioration with aging.
2002-12
K vitamins, PTP antagonism, and cell growth arrest.
2002-12
Why do co-solvents enhance the solubility of solutes in supercritical fluids? New evidence and opinion.
2002-11-15
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.
2002-10-20
DYKAT of Baylis-Hillman adducts: concise total synthesis of furaquinocin E.
2002-10-02
Fetal growth in rats treated with lapachol.
2002-10
Magneto-switchable electrocatalytic and bioelectrocatalytic transformations.
2002-09-16
Synthesis of monocarbenepalladium(0) complexes and their catalytic behavior in cross-coupling reactions of aryldiazonium salts.
2002-09-02
Cancer therapy with beta-lapachone.
2002-09
[Synthesis of triads based on deuteroporphyrin IX, naphthoquinone, and aromatic amino acids].
2002-08-29
High level expression of chorismate pyruvate-lyase (UbiC) and HMG-CoA reductase in hairy root cultures of Lithospermum erythrorhizon.
2002-08
Lindbladione and related naphthoquinone pigments from a myxomycete Lindbladia tubulina.
2002-08
[Studies on the inhibition of polyhydroxylated aromatic compounds against HIV-1 integrase].
2002-04
Irreversible photo-oxidation of propranolol triggered by self-photogenerated singlet molecular oxygen.
2002-02
Thermal analysis and spectroscopic characterization of interactions between a naphthoquinone derivative with HP-beta-CD or PVP.
2002
Patents

Patents

JP2000143942A
3
JP2000239161A
1
JP2000262278A
1
JP2001013701A
1
JP2002338839A
1
JP2003277755A
2
JP2003533572A
1
JP2004315383A
2
JP2005220037A
1
JP2006151848A
1
JP2007169658A
2
JP2008050403A
1
JP2008201687A
1
JP2009510723A
6
JP2010520238A
15
JP2011032406A
1
JP2011042583A
1
JP4728230B2
5
JP5339040B2
1
JPH00898677A
1
JPH01117781A
1
JPH01201337A
1
JPH01242507A
1
JPH01268660A
1
JPH02235845A
1
JPH02295791A
2
JPH03131669A
1
JPH03243670A
1
JPH04211402A
1
JPH04246402A
1
JPH04300971A
1
JPH05107757A
1
JPH0525205A
1
JPH05292998A
1
JPH054951A
1
JPH06312950A
1
JPH06316601A
1
JPH06347845A
1
JPH0687846A
1
JPH069665A
1
JPH0782303A
1
JPH08317734A
1
JPH08337733A
3
JPH0899843A
1
JPH0977736A
1
JPH10218873A
1
JPH10237062A
1
JPH10246974A
1
JPH10301273A
1
JPH1036237A
1
JPH11139947A
1

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
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
  • Download
Name Type Language
NSC-9583
Preferred Name English
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
1,4-NAPHTHALENEDIONE
Systematic Name English
Code System Code Type Description
EPA CompTox
DTXSID5040704
Created by admin on Mon Mar 31 19:31:21 GMT 2025 , Edited by admin on Mon Mar 31 19:31:21 GMT 2025
PRIMARY
PUBCHEM
8530
Created by admin on Mon Mar 31 19:31:21 GMT 2025 , Edited by admin on Mon Mar 31 19:31:21 GMT 2025
PRIMARY
HSDB
2037
Created by admin on Mon Mar 31 19:31:21 GMT 2025 , Edited by admin on Mon Mar 31 19:31:21 GMT 2025
PRIMARY
NSC
9583
Created by admin on Mon Mar 31 19:31:21 GMT 2025 , Edited by admin on Mon Mar 31 19:31:21 GMT 2025
PRIMARY
DAILYMED
RBF5ZU7R7K
Created by admin on Mon Mar 31 19:31:21 GMT 2025 , Edited by admin on Mon Mar 31 19:31:21 GMT 2025
PRIMARY
ECHA (EC/EINECS)
204-977-6
Created by admin on Mon Mar 31 19:31:21 GMT 2025 , Edited by admin on Mon Mar 31 19:31:21 GMT 2025
PRIMARY
FDA UNII
RBF5ZU7R7K
Created by admin on Mon Mar 31 19:31:21 GMT 2025 , Edited by admin on Mon Mar 31 19:31:21 GMT 2025
PRIMARY
CHEBI
27418
Created by admin on Mon Mar 31 19:31:21 GMT 2025 , Edited by admin on Mon Mar 31 19:31:21 GMT 2025
PRIMARY
RXCUI
1602556
Created by admin on Mon Mar 31 19:31:21 GMT 2025 , Edited by admin on Mon Mar 31 19:31:21 GMT 2025
PRIMARY RxNorm
MERCK INDEX
m7750
Created by admin on Mon Mar 31 19:31:21 GMT 2025 , Edited by admin on Mon Mar 31 19:31:21 GMT 2025
PRIMARY Merck Index
WIKIPEDIA
1,4-NAPHTHOQUINONE
Created by admin on Mon Mar 31 19:31:21 GMT 2025 , Edited by admin on Mon Mar 31 19:31:21 GMT 2025
PRIMARY
CAS
130-15-4
Created by admin on Mon Mar 31 19:31:21 GMT 2025 , Edited by admin on Mon Mar 31 19:31:21 GMT 2025
PRIMARY
Related Record Type Details
Structure of NAPHTHALENE
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