Atromentin is a natural product with a unique structure, consisting of a benzofuran core and a quinone moiety. It is a red pigment produced by various fungi, including the mushroom *Dermocybe sanguinea*. Atromentin has been shown to exhibit a range of biological activities, including antioxidant, anti-inflammatory, and cytotoxic properties. It is studied for its potential therapeutic applications, particularly in cancer treatment and wound healing. The synthesis of atromentin involves complex multi-step reactions, often utilizing natural precursors like anthraquinones. Its importance lies in its unique biological properties and potential applications in medicine and other fields. Further research is being conducted to explore its full therapeutic potential and develop novel therapeutic agents.'
atromentin: an enoyl-ACP reductase (FabK) inhibitor; isolated from Streptococcus pneumoniae; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
atromentin : A member of the class of dihydroxy-1,4-benzoquinones that is 2,5-dihydroxycyclohexa-2,5-diene-1,4-dione which is substituted by a 4-hydroxyphenyl group at positions 3 and 6. It is a mushroom pigment isolated from several fungi species and acts as a smooth muscle stimulant, and exhibits anticoagulant, antibacterial and antineoplastic properties. [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 | 99148 |
| CHEMBL ID | 4593579 |
| CHEBI ID | 149660 |
| SCHEMBL ID | 9176577 |
| MeSH ID | M0507976 |
| Synonym |
|---|
| 519-67-5 |
| nsc-187730 |
| 2,4-dione, 2,5-dihydroxy-3,6-bis(4-hydroxyphenyl)- |
| p-benzoquinone,5-dihydroxy-3,6-bis(p-hydroxyphenyl)- |
| nsc187730 |
| atromentin |
| 2,5-dihydroxy-3,6-bis(4-hydroxyphenyl)cyclohexa-2,5-diene-1,4-dione |
| 3',4,4'',6'-tetrahydroxy[1,1':4',1''-terphenyl]-2',5'-dione |
| 2,5-dihydroxy-3,6-bis(p-hydroxyphenyl)-p-benzoquinone |
| 1(4),2(3),2(6),3(4)-tetrahydroxy[1(1),2(1):2(4),3(1)-terphenyl]-2(2),2(5)-dione |
| CHEBI:149660 |
| 2,5-dihydroxy-3,6-bis(4-hydroxyphenyl)-1,4-benzoquinone |
| p-benzoquinone, 2,5-dihydroxy-3,6-bis(p-hydroxyphenyl)- |
| unii-59557692u6 |
| 59557692u6 , |
| nsc 187730 |
| 2,5-cyclohexadiene-1,4-dione, 2,5-dihydroxy-3,6-bis(4-hydroxyphenyl)- |
| SCHEMBL9176577 |
| 2,5-dihydroxy-3,6-bis(4-hydroxyphenyl)-2,5-cyclohexadiene-1,4-dione |
| 2,5-dihydroxy-3,6-bis(4-hydroxyphenyl)benzo-1,4-quinone # |
| FKQQKMGWCJGUCS-UHFFFAOYSA-N |
| DTXSID60199863 |
| Q4817643 |
| CHEMBL4593579 , |
| bdbm50536674 |
| AKOS040750627 |
| Excerpt | Relevance | Reference |
|---|---|---|
| " The procedure relies on a computational screening for activity identification coupled with experimental trials for dose-response characterization." | ( Hybrid in silico/in vitro target fishing to assign function to "orphan" compounds of food origin - The case of the fungal metabolite atromentin. Aichinger, G; Brock, M; Cánovas, D; Dall'Asta, C; Dellafiora, L; Geib, E; Marko, D; Sánchez-Barrionuevo, L, 2019) | 0.72 |
| Role | Description |
|---|---|
| fungal metabolite | Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds. |
| EC 1.3.1.9 [enoyl-[acyl-carrier-protein] reductase (NADH)] inhibitor | An EC 1.3.1.* (oxidoreductase acting on donor CH-CH group, NAD+ or NADP+ as acceptor) inhibitor that interferes with the action of enoyl-[acyl-carrier-protein] reductase (NADH), EC 1.3.1.9. |
| biological pigment | An endogenous molecular entity that results in a colour of an organism as the consequence of the selective absorption of light. |
| anticoagulant | An agent that prevents blood clotting. |
| apoptosis inducer | Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms. |
| antineoplastic agent | A substance that inhibits or prevents the proliferation of neoplasms. |
| antibacterial agent | A substance (or active part thereof) that kills or slows the growth of bacteria. |
| [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 |
|---|---|
| dihydroxy-1,4-benzoquinones | A hydroxybenzoquinone that is any 1,4-benzoquinone in which two of the substituents on the quinone ring are hydroxy groups. |
| polyphenol | Members of the class of phenols that contain 2 or more benzene rings each of which is substituted by at least one hydroxy group. |
| [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] | |
| Pathway | Proteins | Compounds |
|---|---|---|
| atromentin biosynthesis | 3 | 8 |
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Sentrin-specific protease 1 | Homo sapiens (human) | IC50 (µMol) | 4.9450 | 0.0064 | 2.6446 | 6.1000 | AID1637028; AID1637029 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Process | via Protein(s) | Taxonomy |
|---|---|---|
| positive regulation of transcription by RNA polymerase II | Sentrin-specific protease 1 | Homo sapiens (human) |
| proteolysis | Sentrin-specific protease 1 | Homo sapiens (human) |
| activation of cysteine-type endopeptidase activity involved in apoptotic process | Sentrin-specific protease 1 | Homo sapiens (human) |
| protein sumoylation | Sentrin-specific protease 1 | Homo sapiens (human) |
| protein desumoylation | Sentrin-specific protease 1 | Homo sapiens (human) |
| regulation of mRNA stability | Sentrin-specific protease 1 | Homo sapiens (human) |
| apoptotic signaling pathway | Sentrin-specific protease 1 | Homo sapiens (human) |
| [Information is prepared from geneontology information from the June-17-2024 release] | ||
| Process | via Protein(s) | Taxonomy |
|---|---|---|
| endopeptidase activity | Sentrin-specific protease 1 | Homo sapiens (human) |
| protein binding | Sentrin-specific protease 1 | Homo sapiens (human) |
| deSUMOylase activity | Sentrin-specific protease 1 | Homo sapiens (human) |
| SUMO-specific endopeptidase activity | Sentrin-specific protease 1 | Homo sapiens (human) |
| [Information is prepared from geneontology information from the June-17-2024 release] | ||
| Process | via Protein(s) | Taxonomy |
|---|---|---|
| nucleoplasm | Sentrin-specific protease 1 | Homo sapiens (human) |
| cytoplasm | Sentrin-specific protease 1 | Homo sapiens (human) |
| focal adhesion | Sentrin-specific protease 1 | Homo sapiens (human) |
| nuclear membrane | Sentrin-specific protease 1 | Homo sapiens (human) |
| nucleus | Sentrin-specific protease 1 | Homo sapiens (human) |
| [Information is prepared from geneontology information from the June-17-2024 release] | ||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID1637028 | Inhibition of recombinant human 6His-tagged SENP1 catalytic domain expressed in Escherichia coli preincubated for 15 mins followed by addition of SUMO1-AMC as substrate measured after 1 hr by fluorescence analysis | 2016 | Bioorganic & medicinal chemistry letters, 09-01, Volume: 26, Issue:17 | Vialinin A and thelephantin G, potent inhibitors of tumor necrosis factor-α production, inhibit sentrin/SUMO-specific protease 1 enzymatic activity. |
| AID1851293 | Inhibition of 17beta-HSD1 (unknown origin) | 2022 | Bioorganic & medicinal chemistry, 09-15, Volume: 70 | Anti-inflammatory and anticancer p-terphenyl derivatives from fungi of the genus Thelephora. |
| AID1851295 | Inhibition of Escherichia coli FabK using t-o-NAC as substrate in presence of NADPH by ELISA analysis | 2022 | Bioorganic & medicinal chemistry, 09-15, Volume: 70 | Anti-inflammatory and anticancer p-terphenyl derivatives from fungi of the genus Thelephora. |
| AID1637029 | Inhibition of full-length recombinant human 6His-tagged SENP1 expressed in Escherichia coli BL21 (DE3) preincubated for 15 mins followed by addition of SUMO1-AMC as substrate measured after 1 hr by fluorescence analysis | 2016 | Bioorganic & medicinal chemistry letters, 09-01, Volume: 26, Issue:17 | Vialinin A and thelephantin G, potent inhibitors of tumor necrosis factor-α production, inhibit sentrin/SUMO-specific protease 1 enzymatic activity. |
| AID1851296 | Inhibition of Staphylococcus aureus FabK using t-o-NAC as substrate in presence of NADPH by ELISA analysis | 2022 | Bioorganic & medicinal chemistry, 09-15, Volume: 70 | Anti-inflammatory and anticancer p-terphenyl derivatives from fungi of the genus Thelephora. |
| AID1851294 | Inhibition of Streptococcus pneumoniae FabK using t-o-NAC as substrate in presence of NADPH by ELISA analysis | 2022 | Bioorganic & medicinal chemistry, 09-15, Volume: 70 | Anti-inflammatory and anticancer p-terphenyl derivatives from fungi of the genus Thelephora. |
| AID1917232 | Antiproliferative activity against human HL-60 cells assessed as inhibition of cell growth incubated for 48 hrs by CCK-8 assay | 2022 | Bioorganic & medicinal chemistry letters, 11-15, Volume: 76 | Comparative analysis of p-terphenylquinone and seriniquinone derivatives as reactive oxygen species-modulating agents. |
| [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 | 3 (25.00) | 29.6817 |
| 2010's | 7 (58.33) | 24.3611 |
| 2020's | 2 (16.67) | 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 (27.95) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 1 (8.33%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 11 (91.67%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||