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
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
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 |
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1806 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22218491 |
10.8 µM [IC50] | ||
Target ID: CHEMBL2039 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22071524 |
1.5 µM [Ki] | ||
Target ID: CHEMBL1951 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22071524 |
7.7 µM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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 |
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A new naphthoquinone from Bombax malabaricum. | 2001 |
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Concerted action of DT-diaphorase and superoxide dismutase in preventing redox cycling of naphthoquinones: an evaluation. | 2001 Aug |
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A new naphthoquinone from Pyrola japonica. | 2001 Dec |
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Hydroxysesamone and 2,3-epoxysesamone from roots of Sesamum indicum. | 2001 Dec |
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Discovery, total synthesis, HRV 3C-protease inhibitory activity, and structure-activity relationships of 2-methoxystypandrone and its analogues. | 2001 Dec 17 |
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Synthesis and biological studies of novel nucleoside phosphoramidate prodrugs. | 2001 Dec 6 |
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In vitro and in vivo Leishmanicidal activity of 2-hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthoquinone (lapachol). | 2001 Feb |
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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 |
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Production and characterisation of mucoadhesive nanosuspensions for the formulation of bupravaquone. | 2001 Feb 19 |
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Selective nonpeptidic inhibitors of herpes simplex virus type 1 and human cytomegalovirus proteases. | 2001 Mar |
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NAD(P)H:menadione oxidoreductase of the amitochondriate eukaryote Giardia lamblia: a simpler homologue of the vertebrate enzyme. | 2001 Mar |
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Effects of modulation of tissue activities of DT-diaphorase on the toxicity of 2,3-dimethyl-1,4-naphthoquinone to rats. | 2001 Mar 14 |
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Mutational analyses of cysteine residues of bovine dihydrodiol dehydrogenase 3. | 2001 May 5 |
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Interaction of camel lens zeta-crystallin with quinones: portrait of a substrate by fluorescence spectroscopy. | 2001 Nov 15 |
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Abiotic transformation of catechol and 1-naphthol in aqueous solution-influence of environmental factors. | 2001 Oct |
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Combinatorial screening of heterogeneous catalysis in selective oxidation of naphthalene by laser-induced fluorescence imaging. | 2001 Sep 15 |
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[Studies on the inhibition of polyhydroxylated aromatic compounds against HIV-1 integrase]. | 2002 Apr |
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A new naphthoquinone from Polygonum aviculare. | 2002 Apr |
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Irreversible photo-oxidation of propranolol triggered by self-photogenerated singlet molecular oxygen. | 2002 Feb |
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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 |
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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 |
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Protective effect of aloe extract against the cytotoxicity of 1,4-naphthoquinone in isolated rat hepatocytes involves modulations in cellular thiol levels. | 2002 May |
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DYKAT of Baylis-Hillman adducts: concise total synthesis of furaquinocin E. | 2002 Oct 2 |
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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 |
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Magneto-switchable electrocatalytic and bioelectrocatalytic transformations. | 2002 Sep 16 |
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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 |
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Involvement of Akt in mitochondria-dependent apoptosis induced by a cdc25 phosphatase inhibitor naphthoquinone analog. | 2003 Dec 4 |
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Reactive quinones differentially regulate SAPK/JNK and p38/mHOG stress kinases. | 2003 Feb |
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Mechanisms for naphthalene removal during electrolytic aeration. | 2003 Feb |
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Effects of hydroxypropyl-beta-cyclodextrin on the chemical stability of a naphthoquinone in aqueous solutions. | 2003 Jan |
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Perspective in antimalarial chemotherapy. | 2003 Jul |
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[Succivil efficacy in endogenous intoxication]. | 2003 Jul-Aug |
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In vitro cytotoxicity activity of Diosquinone, a naphthoquinone epoxide. | 2003 Mar |
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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 |
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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
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26666298
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
Edited
Sat Jun 26 13:16:41 UTC 2021
by
admin
on
Sat Jun 26 13:16:41 UTC 2021
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Record UNII |
RBF5ZU7R7K
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Record Status |
Validated (UNII)
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130-15-4
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8530
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2037
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204-977-6
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RBF5ZU7R7K
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1602556
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M7750
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1,4-NAPHTHOQUINONE
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130-15-4
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