berkeleydione: polyketide-terpenoid metabolite, isolated from a Penicillium sp.; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
berkeleydione : A meroterpenoid found in Penicillium rubrum. It has been shown to exhibit inhibitory activity against caspase-1. [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 | 21580417 |
| CHEMBL ID | 400514 |
| CHEBI ID | 69021 |
| SCHEMBL ID | 23361061 |
| MeSH ID | M0476471 |
| Synonym |
|---|
| CHEMBL400514 |
| berkeleydione |
| chebi:69021 , |
| bdbm50355787 |
| methyl (5as,7r,9s,11r,11as)-9-hydroxy-1,1,5,7,9,11a-hexamethyl-14-methylidene-3,8,10-trioxo-3,4,5a,6,7,8,9,10,11a,12-decahydro-7,11-methanocycloocta[4,5]cyclohepta[1,2-c]pyran-11(1h)-carboxylate |
| (5as,7r,9s,11r,11as)-methyl 9-hydroxy-1,1,5,7,9,11a-hexamethyl-14-methylidene-3,8,10-trioxo-1,3,4,5a,6,7,8,9,10,11,11a,12-dodecahydro-7,11-methanocycloocta[4,5]cyclohepta[1,2-c]pyran-11-carboxylate |
| Q15410301 |
| SCHEMBL23361061 |
| methyl (1r,2s,12s,14r,16s)-16-hydroxy-2,6,6,11,14,16-hexamethyl-18-methylidene-8,15,17-trioxo-7-oxatetracyclo[12.3.1.02,12.05,10]octadeca-4,10-diene-1-carboxylate |
| DTXSID001045475 |
| Role | Description |
|---|---|
| cysteine protease inhibitor | Any protease inhibitor that restricts the action of a cysteine protease. |
| antineoplastic agent | A substance that inhibits or prevents the proliferation of neoplasms. |
| Penicillium metabolite | Any fungal metabolite produced during a metabolic reaction in Penicillium. |
| [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 |
|---|---|
| cyclic terpene ketone | An alicyclic ketone in which the carbocyclic ring structure forms part of a terpene skeleton. |
| meroterpenoid | Meroterpenoids are complex organooxygen natural products produced from polyketide and terpenoid precursors. |
| organic heterotetracyclic compound | |
| terpene lactone | |
| tertiary alcohol | A tertiary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has three other carbon atoms attached to it. |
| methyl ester | Any carboxylic ester resulting from the formal condensation of a carboxy group with methanol. |
| beta-diketone | A diketone in which the two keto groups are separated by a single carbon atom. |
| tertiary alpha-hydroxy ketone | An alpha-hydroxy ketone in which the carbonyl group and the hydroxy group are linked by a carbon bearing two organyl groups. |
| [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 | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Interleukin-1 beta | Homo sapiens (human) | IC50 (µMol) | 4.4000 | 2.0000 | 3.2000 | 4.4000 | AID627038 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Process | via Protein(s) | Taxonomy |
|---|---|---|
| cytokine activity | Interleukin-1 beta | Homo sapiens (human) |
| interleukin-1 receptor binding | Interleukin-1 beta | Homo sapiens (human) |
| integrin binding | Interleukin-1 beta | Homo sapiens (human) |
| protein binding | Interleukin-1 beta | Homo sapiens (human) |
| protein domain specific binding | Interleukin-1 beta | Homo sapiens (human) |
| [Information is prepared from geneontology information from the June-17-2024 release] | ||
| Process | via Protein(s) | Taxonomy |
|---|---|---|
| extracellular space | Interleukin-1 beta | Homo sapiens (human) |
| extracellular region | Interleukin-1 beta | Homo sapiens (human) |
| extracellular space | Interleukin-1 beta | Homo sapiens (human) |
| lysosome | Interleukin-1 beta | Homo sapiens (human) |
| cytosol | Interleukin-1 beta | Homo sapiens (human) |
| secretory granule | Interleukin-1 beta | Homo sapiens (human) |
| [Information is prepared from geneontology information from the June-17-2024 release] | ||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID311774 | Growth inhibition of human NCI-H460 cells | 2007 | Journal of natural products, Nov, Volume: 70, Issue:11 | The berkeleyacetals, three meroterpenes from a deep water acid mine waste Penicillium. |
| AID1502660 | Inhibition of LPS-induced nitric oxide production in mouse RAW264.7 cells at 80 uM after 24 hrs by Griess assay relative to control | 2017 | Journal of natural products, 10-27, Volume: 80, Issue:10 | 3,5-Dimethylorsellinic Acid Derived Meroterpenoids from Penicillium chrysogenum MT-12, an Endophytic Fungus Isolated from Huperzia serrata. |
| AID311772 | Inhibition of MMP3 | 2007 | Journal of natural products, Nov, Volume: 70, Issue:11 | The berkeleyacetals, three meroterpenes from a deep water acid mine waste Penicillium. |
| AID627038 | Induction of IL-1 beta production in LPS-induced human THP-1 cells by ELISA | 2011 | Journal of natural products, Oct-28, Volume: 74, Issue:10 | Berkeleyones and related meroterpenes from a deep water acid mine waste fungus that inhibit the production of interleukin 1-β from induced inflammasomes. |
| AID627036 | Inhibition of caspase1 in differentiated human THP-1 cells at 100 ug/ml after 24 hrs by fluorometric assay | 2011 | Journal of natural products, Oct-28, Volume: 74, Issue:10 | Berkeleyones and related meroterpenes from a deep water acid mine waste fungus that inhibit the production of interleukin 1-β from induced inflammasomes. |
| AID311773 | Inhibition of caspase 1 | 2007 | Journal of natural products, Nov, Volume: 70, Issue:11 | The berkeleyacetals, three meroterpenes from a deep water acid mine waste Penicillium. |
| [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 (50.00) | 29.6817 |
| 2010's | 3 (50.00) | 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 (12.56) 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 | 6 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||