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Details

Stereochemistry ACHIRAL
Molecular Formula C10H6O2
Molecular Weight 158.1538
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 1,4-NAPHTHOQUINONE

SMILES

c1ccc2c(c1)C(=O)C=CC2=O

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 158.1538
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
109281
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
7728
 10.8 µM [IC50]
Inhibitor
7728
 1.5 µM [Ki]
Inhibitor
7728
 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
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
A new naphthoquinone from Bombax malabaricum.
2001
Concerted action of DT-diaphorase and superoxide dismutase in preventing redox cycling of naphthoquinones: an evaluation.
2001 Aug
A new naphthoquinone from Pyrola japonica.
2001 Dec
Hydroxysesamone and 2,3-epoxysesamone from roots of Sesamum indicum.
2001 Dec
Discovery, total synthesis, HRV 3C-protease inhibitory activity, and structure-activity relationships of 2-methoxystypandrone and its analogues.
2001 Dec 17
Synthesis and biological studies of novel nucleoside phosphoramidate prodrugs.
2001 Dec 6
In vitro and in vivo Leishmanicidal activity of 2-hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthoquinone (lapachol).
2001 Feb
2- and 3-substituted 1,4-naphthoquinone derivatives as subversive substrates of trypanothione reductase and lipoamide dehydrogenase from Trypanosoma cruzi: synthesis and correlation between redox cycling activities and in vitro cytotoxicity.
2001 Feb 15
Production and characterisation of mucoadhesive nanosuspensions for the formulation of bupravaquone.
2001 Feb 19
Selective nonpeptidic inhibitors of herpes simplex virus type 1 and human cytomegalovirus proteases.
2001 Mar
NAD(P)H:menadione oxidoreductase of the amitochondriate eukaryote Giardia lamblia: a simpler homologue of the vertebrate enzyme.
2001 Mar
Effects of modulation of tissue activities of DT-diaphorase on the toxicity of 2,3-dimethyl-1,4-naphthoquinone to rats.
2001 Mar 14
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
Combinatorial screening of heterogeneous catalysis in selective oxidation of naphthalene by laser-induced fluorescence imaging.
2001 Sep 15
[Studies on the inhibition of polyhydroxylated aromatic compounds against HIV-1 integrase].
2002 Apr
A new naphthoquinone from Polygonum aviculare.
2002 Apr
Irreversible photo-oxidation of propranolol triggered by self-photogenerated singlet molecular oxygen.
2002 Feb
Exploring the primary electron acceptor (QA)-site of the bacterial reaction center from Rhodobacter sphaeroides. Binding mode of vitamin K derivatives.
2002 Feb
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
Induction of p73beta by a naphthoquinone analog is mediated by E2F-1 and triggers apoptosis in HeLa cells.
2002 Jul 3
Cellular pharmacology studies of shikonin derivatives.
2002 May
The anatomy and chemistry of the colour bands of grasstree stems (Xanthorrhoea preissii) used for plant age and fire history determination.
2002 May
Protective effect of aloe extract against the cytotoxicity of 1,4-naphthoquinone in isolated rat hepatocytes involves modulations in cellular thiol levels.
2002 May
DYKAT of Baylis-Hillman adducts: concise total synthesis of furaquinocin E.
2002 Oct 2
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
Cancer therapy with beta-lapachone.
2002 Sep
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
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
Mechanisms for naphthalene removal during electrolytic aeration.
2003 Feb
Effects of hydroxypropyl-beta-cyclodextrin on the chemical stability of a naphthoquinone in aqueous solutions.
2003 Jan
Perspective in antimalarial chemotherapy.
2003 Jul
[Succivil efficacy in endogenous intoxication].
2003 Jul-Aug
In vitro cytotoxicity activity of Diosquinone, a naphthoquinone epoxide.
2003 Mar
Discriminating redox cycling and arylation pathways of reactive chemical toxicity in trout hepatocytes.
2003 Mar
A new approach to evaluating the extent of Michael adduct formation to PAH quinones: tetramethylammonium hydroxide (TMAH) thermochemolysis with GC/MS.
2003 Nov
Isodiospyrin as a novel human DNA topoisomerase I inhibitor.
2003 Nov 15
Phototransformation of 1,4-naphthoquinone in aqueous solution.
2003 Oct
Total syntheses of furaquinocin A, B, and E.
2003 Oct 29
Alternative quinone substrates and inhibitors of human electron-transfer flavoprotein-ubiquinone oxidoreductase.
2004 Mar 1
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
14
JP2011032406A
1
JP2011042583A
1
JP4728230B2
4
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 Sat Jun 26 13:16:41 UTC 2021
Edited
by admin
on Sat Jun 26 13:16:41 UTC 2021
Record UNII
RBF5ZU7R7K
Record Status Validated (UNII)
Record Version
  • Download
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
130-15-4
Created by admin on Sat Jun 26 13:16:41 UTC 2021 , Edited by admin on Sat Jun 26 13:16:41 UTC 2021
PRIMARY
PUBCHEM
8530
Created by admin on Sat Jun 26 13:16:41 UTC 2021 , Edited by admin on Sat Jun 26 13:16:41 UTC 2021
PRIMARY
HSDB
2037
Created by admin on Sat Jun 26 13:16:41 UTC 2021 , Edited by admin on Sat Jun 26 13:16:41 UTC 2021
PRIMARY
ECHA (EC/EINECS)
204-977-6
Created by admin on Sat Jun 26 13:16:41 UTC 2021 , Edited by admin on Sat Jun 26 13:16:41 UTC 2021
PRIMARY
FDA UNII
RBF5ZU7R7K
Created by admin on Sat Jun 26 13:16:41 UTC 2021 , Edited by admin on Sat Jun 26 13:16:41 UTC 2021
PRIMARY
RXCUI
1602556
Created by admin on Sat Jun 26 13:16:41 UTC 2021 , Edited by admin on Sat Jun 26 13:16:41 UTC 2021
PRIMARY RxNorm
MERCK INDEX
M7750
Created by admin on Sat Jun 26 13:16:41 UTC 2021 , Edited by admin on Sat Jun 26 13:16:41 UTC 2021
PRIMARY Merck Index
WIKIPEDIA
1,4-NAPHTHOQUINONE
Created by admin on Sat Jun 26 13:16:41 UTC 2021 , Edited by admin on Sat Jun 26 13:16:41 UTC 2021
PRIMARY
CAS
130-15-4
Created by admin on Sat Jun 26 13:16:41 UTC 2021 , Edited by admin on Sat Jun 26 13:16:41 UTC 2021
PRIMARY
Related Record Type Details
Structure of NAPHTHALENE
PARENT -> METABOLITE
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