Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C14H8O2 |
| Molecular Weight | 208.2121 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O=C1C(=O)C2=CC=CC=C2C3=CC=CC=C13
InChI
InChIKey=YYVYAPXYZVYDHN-UHFFFAOYSA-N
InChI=1S/C14H8O2/c15-13-11-7-3-1-5-9(11)10-6-2-4-8-12(10)14(13)16/h1-8H
| Molecular Formula | C14H8O2 |
| Molecular Weight | 208.2121 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
9,10-PHENANTHRENEDIONE (9,10-Phenanthrenequinone) is a quinone and a useful fluorescent compound. It is a TRPA1 activator. Inhalation of 9,10-phenanthrenequinone (9,10-PQ), a major quinone in diesel exhaust, exerts fatal damage against a variety of cells involved in respiratory function. Exposure to 9,10-phenanthrenequinone accelerates malignant progression of lung cancer cells through up-regulation of aldo-keto reductase 1B10.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL6007 |
|||
Target ID: CHEMBL2654 |
8.0 µM [IC50] | ||
Target ID: P11799 Gene ID: 396445.0 Gene Symbol: Mylk Target Organism: Gallus gallus (Chicken) |
6.0 µM [IC50] | ||
Target ID: CHEMBL2916 |
0.5 µM [IC50] | ||
Target ID: CHEMBL2857 |
1.4 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Exposure to 9,10-phenanthrenequinone accelerates malignant progression of lung cancer cells through up-regulation of aldo-keto reductase 1B10. | 2014-07-15 |
|
| Biochemical properties of human dehydrogenase/reductase (SDR family) member 7. | 2014-01-25 |
|
| Comparative developmental toxicity of environmentally relevant oxygenated PAHs. | 2013-09-01 |
|
| S-nitrosoglutathione covalently modifies cysteine residues of human carbonyl reductase 1 and affects its activity. | 2013-02-25 |
|
| New enzymatic assay for the AKR1C enzymes. | 2013-02-25 |
|
| Interaction of 9,10-phenanthraquinone with dithiol causes oxidative modification of Cu,Zn-superoxide dismutase (SOD) through redox cycling. | 2013 |
|
| Dual effects of N-acetyl-L-cysteine dependent on NQO1 activity: suppressive or promotive of 9,10-phenanthrenequinone-induced toxicity. | 2012-11-01 |
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| Mechanism of inhibition of the ATPase domain of human topoisomerase IIα by 1,4-benzoquinone, 1,2-naphthoquinone, 1,4-naphthoquinone, and 9,10-phenanthroquinone. | 2012-04 |
|
| Specificity of human aldo-keto reductases, NAD(P)H:quinone oxidoreductase, and carbonyl reductases to redox-cycle polycyclic aromatic hydrocarbon diones and 4-hydroxyequilenin-o-quinone. | 2011-12-19 |
|
| Retinaldehyde is a substrate for human aldo-keto reductases of the 1C subfamily. | 2011-12-15 |
|
| A novel approach for a toxicity prediction model of environmental pollutants by using a quantitative structure-activity relationship method based on toxicogenomics. | 2011 |
|
| [Development of selective determination methods for quinones with fluorescence and chemiluminescence detection and their application to environmental and biological samples]. | 2010-10 |
|
| 10-(2-Pyrid-yloxy)phenanthren-9-ol. | 2010-08-28 |
|
| 10-(2-Eth-oxy-1,3-thia-zol-5-yl)-10-hy-droxy-phenanthren-9(10H)-one. | 2010-08-11 |
|
| Manganese catalysts for C-H activation: an experimental/theoretical study identifies the stereoelectronic factor that controls the switch between hydroxylation and desaturation pathways. | 2010-06-09 |
|
| 4-[(2,4-Dimethyl-thia-zol-5-yl)meth-yl]-4-hydr-oxy-2-methyl-isoquinoline-1,3(2H,4H)-dione. | 2010-03-27 |
|
| Nitric oxide mitigates apoptosis in human endothelial cells induced by 9,10-phenanthrenequinone: role of proteasomal function. | 2010-02-09 |
|
| [Separation of derivatized aliphatic aldehydes in beverage by nonaqueous capillary electrophoresis]. | 2010-01 |
|
| Redox processes in the iron(III)/9,10-phenanthraquinone system. | 2009-12-21 |
|
| Crystal structures of Pseudomonas syringae pv. tomato DC3000 quinone oxidoreductase and its complex with NADPH. | 2009-12-18 |
|
| catena-Poly[[(1,10-phenanthroline-5,6-dione-κN,N')lead(II)]-μ-terephthalato-κO:O]. | 2009-11-07 |
|
| Poly[aqua-bis(μ(4)-naphthalene-1,4-di-carboxyl-ato)(1,10-phenanthroline-5,6-dione)dimanganese(II)]. | 2009-11-07 |
|
| Benzyl 3-(10-oxo-9,10-dihydrophenanthren-9-ylidene)dithiocarbazate. | 2009-10-28 |
|
| Involvement of an aldo-keto reductase (AKR1C3) in redox cycling of 9,10-phenanthrenequinone leading to apoptosis in human endothelial cells. | 2009-09-14 |
|
| The catalytic mechanism of NADH-dependent reduction of 9,10-phenanthrenequinone by Candida tenuis xylose reductase reveals plasticity in an aldo-keto reductase active site. | 2009-06-12 |
|
| Quinone-enhanced reduction of nitric oxide by xanthine/xanthine oxidase. | 2009-05 |
|
| Transgenic expression of aflatoxin aldehyde reductase (AKR7A1) modulates aflatoxin B1 metabolism but not hepatic carcinogenesis in the rat. | 2009-05 |
|
| Analysis of the substrate-binding site of human carbonyl reductases CBR1 and CBR3 by site-directed mutagenesis. | 2009-03-16 |
|
| Particulate matter (PM) research centers (1999-2005) and the role of interdisciplinary center-based research. | 2009-02 |
|
| Salt stress induces production of melanin related metabolites in the phytopathogenic fungus Leptosphaeria maculans. | 2009-01 |
|
| Human carbonyl reductase 4 is a mitochondrial NADPH-dependent quinone reductase. | 2008-12-26 |
|
| Using an aryl phenanthroimidazole moiety as a conjugated flexible intercalator to improve the hybridization efficiency of a triplex-forming oligonucleotide. | 2008-12-01 |
|
| Photoionization studies on various quinones by an infrared laser desorption/tunable VUV photoionization TOF mass spectrometry. | 2008-12 |
|
| Stabilizing the elusive ortho-quinone/copper(I) oxidation state combination through pi/pi interaction in an isolated complex. | 2008-11-19 |
|
| [Structure and function of peroxisomal tetrameric carbonyl reductase]. | 2008-11 |
|
| Characterization of human DHRS4: an inducible short-chain dehydrogenase/reductase enzyme with 3beta-hydroxysteroid dehydrogenase activity. | 2008-09-15 |
|
| One-step versus stepwise mechanism in protonated amino acid-promoted electron-transfer reduction of a quinone by electron donors and two-electron reduction by a dihydronicotinamide adenine dinucleotide analogue. Interplay between electron transfer and hydrogen bonding. | 2008-04-30 |
|
| Redox cycling of 9,10-phenanthraquinone to cause oxidative stress is terminated through its monoglucuronide conjugation in human pulmonary epithelial A549 cells. | 2008-04-15 |
|
| Cell death by SecTRAPs: thioredoxin reductase as a prooxidant killer of cells. | 2008-04-02 |
|
| 9,10-Phenanthrenequinone induces DNA deletions and forward mutations via oxidative mechanisms in the yeast Saccharomyces cerevisiae. | 2008-03 |
|
| An indomethacin analogue, N-(4-chlorobenzoyl)-melatonin, is a selective inhibitor of aldo-keto reductase 1C3 (type 2 3alpha-HSD, type 5 17beta-HSD, and prostaglandin F synthase), a potential target for the treatment of hormone dependent and hormone independent malignancies. | 2008-01-15 |
|
| Evidence from ESI-MS for NQO1-catalyzed reduction of estrogen ortho-quinones. | 2007-11-01 |
|
| Temperature dependence properties of holographic gratings in phenanthrenquinone doped poly(methyl methacrylate) photopolymers. | 2007-10-20 |
|
| An approach to evaluate two-electron reduction of 9,10-phenanthraquinone and redox activity of the hydroquinone associated with oxidative stress. | 2007-09-01 |
|
| Characterization of an oligomeric carbonyl reductase of dog liver: its identity with peroxisomal tetrameric carbonyl reductase. | 2007-09 |
|
| Inhibitory effects of diesel exhaust components and flavonoids on 20alpha-hydroxysteroid dehydrogenase activity in mouse tissues. | 2007-08 |
|
| Modified polymethylmethacrylate as a base for thermostable optical recording media. | 2007-07-09 |
|
| Quinone emissions from gasoline and diesel motor vehicles. | 2007-07-01 |
|
| Assessment of the toxicity of mixtures of nickel or cadmium with 9,10-phenanthrenequinone to Daphnia magna: impact of a reactive oxygen-mediated mechanism with different redox-active metals. | 2007-07 |
|
| Derivatised carbon powder electrodes: reagentless pH sensors. | 2004-07-08 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 21:18:13 GMT 2025
by
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on
Mon Mar 31 21:18:13 GMT 2025
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| Record UNII |
42L7BZ8H74
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| Record Status |
Validated (UNII)
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| Record Version |
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Phenanthrenequinone
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