3',4'-dihydroxyaurone : A hydroxyaurone that is aurone which is substituted by hydroxy groups at the 3' and 4' positions; major species at pH 7.3. It shows inhibitory activity against several isoforms of the histone deacetylase complex (HDAC). [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 | 5793932 |
| CHEMBL ID | 1478023 |
| CHEBI ID | 144745 |
| SCHEMBL ID | 3709614 |
| Synonym |
|---|
| NCGC00165901-01 |
| (2z)-2-[(3,4-dihydroxyphenyl)methylidene]-1-benzofuran-3-one |
| 3',4'-dihydroxyaurone |
| (2z)-2-[(3,4-dihydroxyphenyl)methylidene]-1-benzofuran-3(2h)-one |
| CHEBI:144745 |
| CHEMBL1478023 , |
| SCHEMBL3709614 |
| 2-[(z)-3,4-dihydroxybenzylidene]-2,3-dihydrobenzofuran-3-one |
| bdbm50036932 |
| skiv |
| AKOS027476231 |
| HY-12895 |
| CS-0012759 |
| 927429-51-4 |
| (z)-2-(3,4-dihydroxybenzylidene)benzofuran-3(2h)-one |
| 2-(3,4-dihydroxy-benzylidene)-benzofuran-3-one, sphingosine kinase inhibitor v |
| Excerpt | Reference | Relevance |
|---|---|---|
| "The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs." | ( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019) | 0.51 |
| Role | Description |
|---|---|
| EC 3.5.1.98 (histone deacetylase) inhibitor | An EC 3.5.1.* (non-peptide linear amide C-N hydrolase) inhibitor that interferes with the function of histone deacetylase (EC 3.5.1.98). |
| [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 |
|---|---|
| hydroxyaurone | Any member of the class of aurones in which one or more ring hydrogens are replaced by hydroxy groups. |
| catechols | Any compound containing an o-diphenol component. |
| [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 | 25.1189 | 0.0032 | 45.4673 | 12,589.2998 | AID2517 |
| Chain A, TYROSYL-DNA PHOSPHODIESTERASE | Homo sapiens (human) | Potency | 56.2341 | 0.0040 | 23.8416 | 100.0000 | AID485290 |
| Chain A, Putative fructose-1,6-bisphosphate aldolase | Giardia intestinalis | Potency | 17.7407 | 0.1409 | 11.1940 | 39.8107 | AID2451 |
| Chain A, ATP-DEPENDENT DNA HELICASE Q1 | Homo sapiens (human) | Potency | 34.8937 | 0.1259 | 19.1169 | 125.8920 | AID2549; AID504841 |
| phosphopantetheinyl transferase | Bacillus subtilis | Potency | 35.4813 | 0.1413 | 37.9142 | 100.0000 | AID1490 |
| ATAD5 protein, partial | Homo sapiens (human) | Potency | 5.1245 | 0.0041 | 10.8903 | 31.5287 | AID686934; AID720565 |
| vitamin D3 receptor isoform VDRA | Homo sapiens (human) | Potency | 39.8107 | 0.3548 | 28.0659 | 89.1251 | AID504847 |
| nuclear receptor ROR-gamma isoform 1 | Mus musculus (house mouse) | Potency | 25.6651 | 0.0079 | 8.2332 | 1,122.0200 | AID2546; AID2551 |
| DNA polymerase kappa isoform 1 | Homo sapiens (human) | Potency | 13.3714 | 0.0316 | 22.3146 | 100.0000 | AID588579 |
| [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) |
|---|---|---|---|---|---|---|---|
| Histone deacetylase 3 | Homo sapiens (human) | IC50 (µMol) | 8.2000 | 0.0004 | 0.6196 | 10.0000 | AID1173704 |
| Serine/threonine-protein kinase 17B | Homo sapiens (human) | IC50 (µMol) | 3.0800 | 0.0258 | 2.2072 | 6.2000 | AID1446693 |
| Histone deacetylase 4 | Homo sapiens (human) | IC50 (µMol) | 8.2000 | 0.0006 | 1.0526 | 10.0000 | AID1173704 |
| Histone deacetylase 1 | Homo sapiens (human) | IC50 (µMol) | 9.8000 | 0.0001 | 0.5543 | 9.9000 | AID1173704; AID1173705 |
| Histone deacetylase 7 | Homo sapiens (human) | IC50 (µMol) | 8.2000 | 0.0007 | 1.0260 | 9.9000 | AID1173704 |
| Histone deacetylase 2 | Homo sapiens (human) | IC50 (µMol) | 6.6500 | 0.0001 | 0.7221 | 9.9700 | AID1173704; AID1173706 |
| Polyamine deacetylase HDAC10 | Homo sapiens (human) | IC50 (µMol) | 8.2000 | 0.0005 | 0.7245 | 9.9000 | AID1173704 |
| Histone deacetylase 11 | Homo sapiens (human) | IC50 (µMol) | 8.2000 | 0.0003 | 0.9298 | 9.9000 | AID1173704 |
| Histone deacetylase 8 | Homo sapiens (human) | IC50 (µMol) | 8.2000 | 0.0007 | 0.9947 | 9.9000 | AID1173704 |
| Histone deacetylase 6 | Homo sapiens (human) | IC50 (µMol) | 17.5500 | 0.0000 | 0.5376 | 9.9000 | AID1173704; AID1173707 |
| Histone deacetylase 9 | Homo sapiens (human) | IC50 (µMol) | 8.2000 | 0.0005 | 0.9413 | 9.9000 | AID1173704 |
| Histone deacetylase 5 | Homo sapiens (human) | IC50 (µMol) | 8.2000 | 0.0007 | 0.9610 | 10.0000 | AID1173704 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID1173712 | Modulation of sirtuin 2 (unknown origin) by thermal shift assay | 2014 | Bioorganic & medicinal chemistry letters, Dec-01, Volume: 24, Issue:23 | Aurones as histone deacetylase inhibitors: identification of key features. |
| AID1090554 | Antifeedant activity against Spodoptera litura in compound treated cork borer from fresh sweet potato leaves assessed as leaf disk consumed at 0.33 mg/cm2 at 26.5 degC | 2007 | Journal of agricultural and food chemistry, Feb-07, Volume: 55, Issue:3 | Synthesis and insect antifeedant activity of aurones against Spodoptera litura larvae. |
| AID1446693 | Inhibition of recombinant GST-tagged DRAK2 (unknown origin) autophosphorylation after 2 hrs by ADP-glo assay | 2017 | European journal of medicinal chemistry, Apr-21, Volume: 130 | Discovery of benzofuran-3(2H)-one derivatives as novel DRAK2 inhibitors that protect islet β-cells from apoptosis. |
| AID1173707 | Inhibition of HDAC6 (unknown origin) after 15 mins by fluorescence assay | 2014 | Bioorganic & medicinal chemistry letters, Dec-01, Volume: 24, Issue:23 | Aurones as histone deacetylase inhibitors: identification of key features. |
| AID1173710 | Cytotoxicity against human MCF7 cells assessed as cell viability at 15 uM after 72 hrs by Celltitre-glo assay | 2014 | Bioorganic & medicinal chemistry letters, Dec-01, Volume: 24, Issue:23 | Aurones as histone deacetylase inhibitors: identification of key features. |
| AID1173713 | Inhibition of RAR-beta (unknown origin) assessed as change in DNA methylation | 2014 | Bioorganic & medicinal chemistry letters, Dec-01, Volume: 24, Issue:23 | Aurones as histone deacetylase inhibitors: identification of key features. |
| AID1173704 | Inhibition of HDAC in human HeLa cell extract after 15 mins by fluorescence assay | 2014 | Bioorganic & medicinal chemistry letters, Dec-01, Volume: 24, Issue:23 | Aurones as histone deacetylase inhibitors: identification of key features. |
| AID1173706 | Inhibition of HDAC2 (unknown origin) after 15 mins by fluorescence assay | 2014 | Bioorganic & medicinal chemistry letters, Dec-01, Volume: 24, Issue:23 | Aurones as histone deacetylase inhibitors: identification of key features. |
| AID1090556 | Antifeedant activity against Spodoptera litura in compound treated cork borer from fresh sweet potato leaves assessed as leaf disk consumed at 26.5 degC | 2007 | Journal of agricultural and food chemistry, Feb-07, Volume: 55, Issue:3 | Synthesis and insect antifeedant activity of aurones against Spodoptera litura larvae. |
| AID1173705 | Inhibition of HDAC1 (unknown origin) after 15 mins by fluorescence assay | 2014 | Bioorganic & medicinal chemistry letters, Dec-01, Volume: 24, Issue:23 | Aurones as histone deacetylase inhibitors: identification of key features. |
| AID1173709 | Cytotoxicity against human MeT-5A cells after 16 hrs by luciferase reporter gene assay | 2014 | Bioorganic & medicinal chemistry letters, Dec-01, Volume: 24, Issue:23 | Aurones as histone deacetylase inhibitors: identification of key features. |
| AID1173708 | Inhibition of HDAC in human MeT-5A cells assessed as hisone H3 acetylation after 16 hrs by BRET assay | 2014 | Bioorganic & medicinal chemistry letters, Dec-01, Volume: 24, Issue:23 | Aurones as histone deacetylase inhibitors: identification of key features. |
| AID1173703 | Inhibition of HDAC in human HeLa cell extract at 100 uM after 15 mins by fluorescence assay | 2014 | Bioorganic & medicinal chemistry letters, Dec-01, Volume: 24, Issue:23 | Aurones as histone deacetylase inhibitors: identification of key features. |
| AID1653375 | Inhibition of SK (unknown origin) | 2019 | European journal of medicinal chemistry, Mar-15, Volume: 166 | Aurone: A biologically attractive scaffold as anticancer agent. |
| AID1173711 | Cytotoxicity against human HepG2 cells assessed as cell viability at 15 uM after 72 hrs by Celltitre-glo assay | 2014 | Bioorganic & medicinal chemistry letters, Dec-01, Volume: 24, Issue:23 | Aurones as histone deacetylase inhibitors: identification of key features. |
| AID1346987 | P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen | 2019 | Molecular pharmacology, 11, Volume: 96, Issue:5 | A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. |
| AID1346986 | P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen | 2019 | Molecular pharmacology, 11, Volume: 96, Issue:5 | A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 0 (0.00) | 18.2507 |
| 2000's | 1 (20.00) | 29.6817 |
| 2010's | 4 (80.00) | 24.3611 |
| 2020's | 0 (0.00) | 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 weak demand-to-supply ratio for research on this compound.
| This Compound (13.28) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 1 (20.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 4 (80.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||