Acenaphthenequinone is a bright orange solid organic compound with the formula C12H6O2. It is a derivative of acenaphthene, obtained by oxidizing the corresponding acenaphthene. Acenaphthenequinone is an important starting material for the synthesis of many other organic compounds, including dyes, pharmaceuticals, and polymers. It is also used as a reagent in organic chemistry. Acenaphthenequinone has been shown to have a variety of biological activities, including anticancer, antibacterial, and antifungal properties. It is also a potent photosensitizer, which means that it can be used to generate singlet oxygen, a highly reactive species that can damage cells. Due to its interesting properties, acenaphthenequinone has been the subject of much research. For example, scientists have studied its potential as a photosensitizer for photodynamic therapy, a treatment for cancer that uses light to activate a drug. They have also investigated its use as a reagent in the synthesis of new materials with potential applications in electronics and optoelectronics. '
acenaphthoquinone : An orthoquinone that is the 1,2-dioxo derivative of acenaphthene. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]
| ID Source | ID |
|---|---|
| PubMed CID | 6724 |
| CHEMBL ID | 395653 |
| CHEBI ID | 15342 |
| SCHEMBL ID | 141538 |
| MeSH ID | M0081284 |
| Synonym |
|---|
| HMS2583D13 |
| acenaphthene-1,2-quinone |
| 1,2-acenaphthenequinone |
| nsc-7656 |
| acenaphthenedione |
| nsc7656 |
| 1,2-acenaphthenedione |
| 1,2-acenaphthylenedione |
| bdbm22853 |
| 1,2-dihydroacenaphthylenedione |
| 1,2-dione-based compound, 10 |
| acenaphthylenequinone |
| ccris 5318 |
| nsc 7656 |
| hsdb 2660 |
| acenaphthaquinone |
| brn 0879172 |
| einecs 201-441-3 |
| ACQ , |
| smr000225434 |
| MLS000705880 |
| acenaphthenequinone , |
| acenaphthoquinone |
| 82-86-0 |
| 1,2-diketoacenaphthene |
| C02807 |
| acenaphthylene-1,2-quinone |
| acenaphthene-1,2-dione |
| acenaphthene quinone |
| CHEBI:15342 , |
| acenaphthylenedione |
| acenaphthylene-1,2-dione |
| acenaphthodione |
| diketoacenaphthene |
| inchi=1/c12h6o2/c13-11-8-5-1-3-7-4-2-6-9(10(7)8)12(11)14/h1-6 |
| A0004 , |
| CHEMBL395653 |
| acenaphthequinone |
| STK802161 |
| AKOS000120366 |
| A840468 |
| NCGC00247177-01 |
| dtxcid6029389 |
| cas-82-86-0 |
| NCGC00260493-01 |
| tox21_202947 |
| dtxsid7049429 , |
| BBL011021 |
| 4-07-00-02498 (beilstein handbook reference) |
| 3950d6ueiq , |
| unii-3950d6ueiq |
| FT-0621717 |
| EPITOPE ID:116186 |
| 1,2-dihydroacenaphthylene-1,2-dione |
| SCHEMBL141538 |
| BP-13440 |
| acenaphtenquinone |
| acenaphtoquinone |
| F1908-0136 |
| W-104156 |
| 1,2-acenaphthalenedione |
| mfcd00003805 |
| CS-W017119 |
| AS-14620 |
| acenaphthenchinon |
| EN300-20210 |
| SY011135 |
| HMS3749K15 |
| Q2739953 |
| Z104477294 |
| Role | Description |
|---|---|
| epitope | The biological role played by a material entity when bound by a receptor of the adaptive immune system. Specific site on an antigen to which an antibody binds. |
| chain carrier | The role played by a molecular entity, such as an atom or free radical, which is involved in chain-propagating reactions. |
| [role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Class | Description |
|---|---|
| orthoquinones | Any quinone in which the carbons of the two carbonyl groups in the quinone system are joined to each other by a single bond. |
| [compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Protein | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASE | Homo sapiens (human) | Potency | 19.9526 | 0.0032 | 45.4673 | 12,589.2998 | AID2517 |
| Chain A, Putative fructose-1,6-bisphosphate aldolase | Giardia intestinalis | Potency | 2.2334 | 0.1409 | 11.1940 | 39.8107 | AID2451 |
| acetylcholinesterase | Homo sapiens (human) | Potency | 35.5452 | 0.0025 | 41.7960 | 15,848.9004 | AID1347398 |
| RAR-related orphan receptor gamma | Mus musculus (house mouse) | Potency | 13.9390 | 0.0060 | 38.0041 | 19,952.5996 | AID1159521; AID1159523 |
| ATAD5 protein, partial | Homo sapiens (human) | Potency | 20.5962 | 0.0041 | 10.8903 | 31.5287 | AID504466 |
| TDP1 protein | Homo sapiens (human) | Potency | 0.6159 | 0.0008 | 11.3822 | 44.6684 | AID686978; AID686979 |
| GLI family zinc finger 3 | Homo sapiens (human) | Potency | 5.4587 | 0.0007 | 14.5928 | 83.7951 | AID1259369; AID1259392 |
| AR protein | Homo sapiens (human) | Potency | 23.3789 | 0.0002 | 21.2231 | 8,912.5098 | AID1259247; AID743063 |
| Smad3 | Homo sapiens (human) | Potency | 2.8184 | 0.0052 | 7.8098 | 29.0929 | AID588855 |
| caspase 7, apoptosis-related cysteine protease | Homo sapiens (human) | Potency | 68.5199 | 0.0133 | 26.9810 | 70.7614 | AID1346978 |
| aldehyde dehydrogenase 1 family, member A1 | Homo sapiens (human) | Potency | 37.6505 | 0.0112 | 12.4002 | 100.0000 | AID1030 |
| estrogen receptor 2 (ER beta) | Homo sapiens (human) | Potency | 43.2331 | 0.0006 | 57.9133 | 22,387.1992 | AID1259377 |
| nuclear receptor subfamily 1, group I, member 3 | Homo sapiens (human) | Potency | 32.4201 | 0.0010 | 22.6508 | 76.6163 | AID1224838; AID1224839; AID1224893 |
| progesterone receptor | Homo sapiens (human) | Potency | 27.2783 | 0.0004 | 17.9460 | 75.1148 | AID1346795 |
| glucocorticoid receptor [Homo sapiens] | Homo sapiens (human) | Potency | 10.8165 | 0.0002 | 14.3764 | 60.0339 | AID720692; AID720719 |
| retinoic acid nuclear receptor alpha variant 1 | Homo sapiens (human) | Potency | 11.1210 | 0.0030 | 41.6115 | 22,387.1992 | AID1159552; AID1159555 |
| estrogen-related nuclear receptor alpha | Homo sapiens (human) | Potency | 17.8523 | 0.0015 | 30.6073 | 15,848.9004 | AID1224841; AID1224848; AID1224849; AID1259401 |
| pregnane X nuclear receptor | Homo sapiens (human) | Potency | 54.4273 | 0.0054 | 28.0263 | 1,258.9301 | AID1346982 |
| estrogen nuclear receptor alpha | Homo sapiens (human) | Potency | 28.0355 | 0.0002 | 29.3054 | 16,493.5996 | AID1259244; AID743069; AID743075; AID743080 |
| caspase-3 | Homo sapiens (human) | Potency | 68.5199 | 0.0133 | 26.9810 | 70.7614 | AID1346978 |
| euchromatic histone-lysine N-methyltransferase 2 | Homo sapiens (human) | Potency | 79.4328 | 0.0355 | 20.9770 | 89.1251 | AID504332 |
| aryl hydrocarbon receptor | Homo sapiens (human) | Potency | 25.7950 | 0.0007 | 23.0674 | 1,258.9301 | AID743085; AID743122 |
| activating transcription factor 6 | Homo sapiens (human) | Potency | 6.1600 | 0.1434 | 27.6121 | 59.8106 | AID1159516 |
| v-jun sarcoma virus 17 oncogene homolog (avian) | Homo sapiens (human) | Potency | 20.6679 | 0.0578 | 21.1097 | 61.2679 | AID1159526; AID1159528 |
| Histone H2A.x | Cricetulus griseus (Chinese hamster) | Potency | 112.9350 | 0.0391 | 47.5451 | 146.8240 | AID1224845 |
| thyroid hormone receptor beta isoform 2 | Rattus norvegicus (Norway rat) | Potency | 25.8659 | 0.0003 | 23.4451 | 159.6830 | AID743065; AID743067 |
| heat shock protein beta-1 | Homo sapiens (human) | Potency | 21.8564 | 0.0420 | 27.3789 | 61.6448 | AID743210 |
| nuclear factor erythroid 2-related factor 2 isoform 1 | Homo sapiens (human) | Potency | 26.2512 | 0.0006 | 27.2152 | 1,122.0200 | AID743219 |
| nuclear receptor ROR-gamma isoform 1 | Mus musculus (house mouse) | Potency | 3.1623 | 0.0079 | 8.2332 | 1,122.0200 | AID2546 |
| geminin | Homo sapiens (human) | Potency | 6.5131 | 0.0046 | 11.3741 | 33.4983 | AID624297 |
| Vpr | Human immunodeficiency virus 1 | Potency | 8.9125 | 1.5849 | 19.6264 | 63.0957 | AID651644 |
| Voltage-dependent calcium channel gamma-2 subunit | Mus musculus (house mouse) | Potency | 54.4273 | 0.0015 | 57.7890 | 15,848.9004 | AID1259244 |
| Cellular tumor antigen p53 | Homo sapiens (human) | Potency | 4.1541 | 0.0023 | 19.5956 | 74.0614 | AID651631; AID720552 |
| Glutamate receptor 2 | Rattus norvegicus (Norway rat) | Potency | 54.4273 | 0.0015 | 51.7393 | 15,848.9004 | AID1259244 |
| ATPase family AAA domain-containing protein 5 | Homo sapiens (human) | Potency | 27.2783 | 0.0119 | 17.9420 | 71.5630 | AID651632 |
| Ataxin-2 | Homo sapiens (human) | Potency | 27.2783 | 0.0119 | 12.2221 | 68.7989 | AID651632 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Cocaine esterase | Homo sapiens (human) | Ki | 0.1700 | 0.0063 | 0.9835 | 8.0000 | AID731514 |
| Coagulation factor XII | Homo sapiens (human) | Ki | 1.0570 | 0.0025 | 1.8669 | 7.2500 | AID1798260 |
| Cholinesterase | Homo sapiens (human) | Ki | 21.2282 | 0.0000 | 1.5173 | 9.7300 | AID1798260; AID1798261; AID302993 |
| Acetylcholinesterase | Homo sapiens (human) | Ki | 100.0000 | 0.0000 | 1.2786 | 9.7300 | AID1798261; AID302992 |
| Liver carboxylesterase 1 | Homo sapiens (human) | Ki | 0.6466 | 0.0025 | 2.0136 | 8.4800 | AID1798260; AID302991; AID731515 |
| Induced myeloid leukemia cell differentiation protein Mcl-1 | Homo sapiens (human) | IC50 (µMol) | 1,425.0000 | 0.0044 | 2.9235 | 10.0000 | AID721801 |
| Induced myeloid leukemia cell differentiation protein Mcl-1 | Homo sapiens (human) | Ki | 57.0000 | 0.0010 | 1.4653 | 9.5400 | AID721801 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Induced myeloid leukemia cell differentiation protein Mcl-1 | Homo sapiens (human) | Kd | 324.1420 | 2.3240 | 2.5636 | 2.6500 | AID734888 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
| AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2006 | Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5 | Microsphere-based protease assays and screening application for lethal factor and factor Xa. |
| AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
| AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
| AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2006 | Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5 | Microsphere-based protease assays and screening application for lethal factor and factor Xa. |
| AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
| AID504812 | Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign | 2010 | Endocrinology, Jul, Volume: 151, Issue:7 | A small molecule inverse agonist for the human thyroid-stimulating hormone receptor. |
| AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
| AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2006 | Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5 | Microsphere-based protease assays and screening application for lethal factor and factor Xa. |
| AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
| AID1745845 | Primary qHTS for Inhibitors of ATXN expression | |||
| AID651635 | Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression | |||
| AID504810 | Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign | 2010 | Endocrinology, Jul, Volume: 151, Issue:7 | A small molecule inverse agonist for the human thyroid-stimulating hormone receptor. |
| AID762062 | Cytotoxicity against human HCT116 cells after 24 hrs by MTT assay | 2013 | Bioorganic & medicinal chemistry letters, Aug-15, Volume: 23, Issue:16 | Effect of the orthoquinone moiety in 9,10-phenanthrenequinone on its ability to induce apoptosis in HCT-116 and HL-60 cells. |
| AID302991 | Inhibition of human carboxylesterase 1 | 2007 | Journal of medicinal chemistry, Nov-15, Volume: 50, Issue:23 | Planarity and constraint of the carbonyl groups in 1,2-diones are determinants for selective inhibition of human carboxylesterase 1. |
| AID734888 | Binding affinity to his-tagged Mcl-1 (unknown origin) expressed in Escherichia coli BL21 (DE3) cells by ITC analysis | 2013 | European journal of medicinal chemistry, Jan, Volume: 59 | Novel soluble myeloid cell leukemia sequence 1 (Mcl-1) inhibitor (E,E)-2-(benzylaminocarbonyl)-3-styrylacrylonitrile (4g) developed using a fragment-based approach. |
| AID731514 | Inhibition of human iCE using o-NPA as substrate by spectrophotometric assay | 2013 | Journal of natural products, Jan-25, Volume: 76, Issue:1 | Modulation of esterified drug metabolism by tanshinones from Salvia miltiorrhiza ("Danshen"). |
| AID302992 | Inhibition of human acetylcholinesterase 1 | 2007 | Journal of medicinal chemistry, Nov-15, Volume: 50, Issue:23 | Planarity and constraint of the carbonyl groups in 1,2-diones are determinants for selective inhibition of human carboxylesterase 1. |
| AID762061 | Cytotoxicity against human HL60 cells after 24 hrs by WST-1 assay | 2013 | Bioorganic & medicinal chemistry letters, Aug-15, Volume: 23, Issue:16 | Effect of the orthoquinone moiety in 9,10-phenanthrenequinone on its ability to induce apoptosis in HCT-116 and HL-60 cells. |
| AID302990 | Inhibition of human intestinal carboxylesterase | 2007 | Journal of medicinal chemistry, Nov-15, Volume: 50, Issue:23 | Planarity and constraint of the carbonyl groups in 1,2-diones are determinants for selective inhibition of human carboxylesterase 1. |
| AID731515 | Inhibition of human CE1 using o-NPA as substrate by spectrophotometric assay | 2013 | Journal of natural products, Jan-25, Volume: 76, Issue:1 | Modulation of esterified drug metabolism by tanshinones from Salvia miltiorrhiza ("Danshen"). |
| AID721801 | Inhibition of FAM-Bid peptide binding to Mcl1 (unknown origin) expressed in Escherichia coli BL21 by fluorescence polarization-based binding assay | 2013 | European journal of medicinal chemistry, Feb, Volume: 60 | Fragment-based design, synthesis, and biological evaluation of N-substituted-5-(4-isopropylthiophenol)-2-hydroxynicotinamide derivatives as novel Mcl-1 inhibitors. |
| AID302993 | Inhibition of human butyrylcholinesterase | 2007 | Journal of medicinal chemistry, Nov-15, Volume: 50, Issue:23 | Planarity and constraint of the carbonyl groups in 1,2-diones are determinants for selective inhibition of human carboxylesterase 1. |
| AID1798260 | Enzyme Inhibition Assay from Article 10.1021/jm0706867: \\Planarity and constraint of the carbonyl groups in 1,2-diones are determinants for selective inhibition of human carboxylesterase 1.\\ | 2007 | Journal of medicinal chemistry, Nov-15, Volume: 50, Issue:23 | Planarity and constraint of the carbonyl groups in 1,2-diones are determinants for selective inhibition of human carboxylesterase 1. |
| AID1798261 | Cholinesterase Inhibition Assay from Article 10.1021/jm0706867: \\Planarity and constraint of the carbonyl groups in 1,2-diones are determinants for selective inhibition of human carboxylesterase 1.\\ | 2007 | Journal of medicinal chemistry, Nov-15, Volume: 50, Issue:23 | Planarity and constraint of the carbonyl groups in 1,2-diones are determinants for selective inhibition of human carboxylesterase 1. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 1 (5.56) | 18.7374 |
| 1990's | 1 (5.56) | 18.2507 |
| 2000's | 4 (22.22) | 29.6817 |
| 2010's | 11 (61.11) | 24.3611 |
| 2020's | 1 (5.56) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.
| This Compound (31.95) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 18 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||