Page last updated: 2024-11-13

berkeleydione

Description

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]

Cross-References

ID SourceID
PubMed CID21580417
CHEMBL ID400514
CHEBI ID69021
SCHEMBL ID23361061
MeSH IDM0476471

Synonyms (10)

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
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
cysteine protease inhibitorAny protease inhibitor that restricts the action of a cysteine protease.
antineoplastic agentA substance that inhibits or prevents the proliferation of neoplasms.
Penicillium metaboliteAny 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]

Drug Classes (8)

ClassDescription
cyclic terpene ketoneAn alicyclic ketone in which the carbocyclic ring structure forms part of a terpene skeleton.
meroterpenoidMeroterpenoids are complex organooxygen natural products produced from polyketide and terpenoid precursors.
organic heterotetracyclic compound
terpene lactone
tertiary alcoholA 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 esterAny carboxylic ester resulting from the formal condensation of a carboxy group with methanol.
beta-diketoneA diketone in which the two keto groups are separated by a single carbon atom.
tertiary alpha-hydroxy ketoneAn 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 Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Interleukin-1 betaHomo sapiens (human)IC50 (µMol)4.40002.00003.20004.4000AID627038
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (92)

Processvia Protein(s)Taxonomy
positive regulation of gene expressionInterleukin-1 betaHomo sapiens (human)
positive regulation of canonical NF-kappaB signal transductionInterleukin-1 betaHomo sapiens (human)
positive regulation of MAP kinase activityInterleukin-1 betaHomo sapiens (human)
positive regulation of NF-kappaB transcription factor activityInterleukin-1 betaHomo sapiens (human)
cellular response to organic substanceInterleukin-1 betaHomo sapiens (human)
cellular response to xenobiotic stimulusInterleukin-1 betaHomo sapiens (human)
fever generationInterleukin-1 betaHomo sapiens (human)
positive regulation of protein phosphorylationInterleukin-1 betaHomo sapiens (human)
positive regulation of T cell mediated immunityInterleukin-1 betaHomo sapiens (human)
apoptotic processInterleukin-1 betaHomo sapiens (human)
inflammatory responseInterleukin-1 betaHomo sapiens (human)
immune responseInterleukin-1 betaHomo sapiens (human)
signal transductionInterleukin-1 betaHomo sapiens (human)
JNK cascadeInterleukin-1 betaHomo sapiens (human)
cell-cell signalingInterleukin-1 betaHomo sapiens (human)
embryo implantationInterleukin-1 betaHomo sapiens (human)
positive regulation of cell population proliferationInterleukin-1 betaHomo sapiens (human)
negative regulation of cell population proliferationInterleukin-1 betaHomo sapiens (human)
response to carbohydrateInterleukin-1 betaHomo sapiens (human)
vascular endothelial growth factor productionInterleukin-1 betaHomo sapiens (human)
positive regulation of vascular endothelial growth factor productionInterleukin-1 betaHomo sapiens (human)
positive regulation of gene expressionInterleukin-1 betaHomo sapiens (human)
positive regulation of epithelial to mesenchymal transitionInterleukin-1 betaHomo sapiens (human)
negative regulation of glucose transmembrane transportInterleukin-1 betaHomo sapiens (human)
smooth muscle adaptationInterleukin-1 betaHomo sapiens (human)
cytokine-mediated signaling pathwayInterleukin-1 betaHomo sapiens (human)
hyaluronan biosynthetic processInterleukin-1 betaHomo sapiens (human)
positive regulation of cell migrationInterleukin-1 betaHomo sapiens (human)
neutrophil chemotaxisInterleukin-1 betaHomo sapiens (human)
sequestering of triglycerideInterleukin-1 betaHomo sapiens (human)
positive regulation of vascular endothelial growth factor receptor signaling pathwayInterleukin-1 betaHomo sapiens (human)
positive regulation of prostaglandin biosynthetic processInterleukin-1 betaHomo sapiens (human)
positive regulation of fever generationInterleukin-1 betaHomo sapiens (human)
positive regulation of prostaglandin secretionInterleukin-1 betaHomo sapiens (human)
response to lipopolysaccharideInterleukin-1 betaHomo sapiens (human)
positive regulation of granulocyte macrophage colony-stimulating factor productionInterleukin-1 betaHomo sapiens (human)
positive regulation of type II interferon productionInterleukin-1 betaHomo sapiens (human)
positive regulation of interleukin-2 productionInterleukin-1 betaHomo sapiens (human)
positive regulation of interleukin-6 productionInterleukin-1 betaHomo sapiens (human)
positive regulation of interleukin-8 productionInterleukin-1 betaHomo sapiens (human)
response to ATPInterleukin-1 betaHomo sapiens (human)
positive regulation of heterotypic cell-cell adhesionInterleukin-1 betaHomo sapiens (human)
ectopic germ cell programmed cell deathInterleukin-1 betaHomo sapiens (human)
positive regulation of myosin light chain kinase activityInterleukin-1 betaHomo sapiens (human)
positive regulation of T cell proliferationInterleukin-1 betaHomo sapiens (human)
regulation of canonical NF-kappaB signal transductionInterleukin-1 betaHomo sapiens (human)
positive regulation of canonical NF-kappaB signal transductionInterleukin-1 betaHomo sapiens (human)
negative regulation of MAP kinase activityInterleukin-1 betaHomo sapiens (human)
positive regulation of nitric oxide biosynthetic processInterleukin-1 betaHomo sapiens (human)
positive regulation of angiogenesisInterleukin-1 betaHomo sapiens (human)
negative regulation of lipid metabolic processInterleukin-1 betaHomo sapiens (human)
positive regulation of mitotic nuclear divisionInterleukin-1 betaHomo sapiens (human)
positive regulation of DNA-templated transcriptionInterleukin-1 betaHomo sapiens (human)
positive regulation of complement activationInterleukin-1 betaHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIInterleukin-1 betaHomo sapiens (human)
positive regulation of JNK cascadeInterleukin-1 betaHomo sapiens (human)
negative regulation of insulin receptor signaling pathwayInterleukin-1 betaHomo sapiens (human)
positive regulation of protein export from nucleusInterleukin-1 betaHomo sapiens (human)
astrocyte activationInterleukin-1 betaHomo sapiens (human)
regulation of defense response to virus by hostInterleukin-1 betaHomo sapiens (human)
positive regulation of inflammatory responseInterleukin-1 betaHomo sapiens (human)
regulation of neurogenesisInterleukin-1 betaHomo sapiens (human)
negative regulation of neurogenesisInterleukin-1 betaHomo sapiens (human)
regulation of insulin secretionInterleukin-1 betaHomo sapiens (human)
negative regulation of synaptic transmissionInterleukin-1 betaHomo sapiens (human)
defense response to Gram-positive bacteriumInterleukin-1 betaHomo sapiens (human)
negative regulation of lipid catabolic processInterleukin-1 betaHomo sapiens (human)
positive regulation of lipid catabolic processInterleukin-1 betaHomo sapiens (human)
regulation of nitric-oxide synthase activityInterleukin-1 betaHomo sapiens (human)
positive regulation of membrane protein ectodomain proteolysisInterleukin-1 betaHomo sapiens (human)
positive regulation of DNA-binding transcription factor activityInterleukin-1 betaHomo sapiens (human)
positive regulation of NF-kappaB transcription factor activityInterleukin-1 betaHomo sapiens (human)
positive regulation of cell divisionInterleukin-1 betaHomo sapiens (human)
positive regulation of glial cell proliferationInterleukin-1 betaHomo sapiens (human)
positive regulation of cell adhesion molecule productionInterleukin-1 betaHomo sapiens (human)
positive regulation of calcidiol 1-monooxygenase activityInterleukin-1 betaHomo sapiens (human)
negative regulation of adiponectin secretionInterleukin-1 betaHomo sapiens (human)
regulation of ERK1 and ERK2 cascadeInterleukin-1 betaHomo sapiens (human)
monocyte aggregationInterleukin-1 betaHomo sapiens (human)
interleukin-1-mediated signaling pathwayInterleukin-1 betaHomo sapiens (human)
response to interleukin-1Interleukin-1 betaHomo sapiens (human)
cellular response to mechanical stimulusInterleukin-1 betaHomo sapiens (human)
positive regulation of monocyte chemotactic protein-1 productionInterleukin-1 betaHomo sapiens (human)
extrinsic apoptotic signaling pathway in absence of ligandInterleukin-1 betaHomo sapiens (human)
cellular response to interleukin-17Interleukin-1 betaHomo sapiens (human)
positive regulation of neuroinflammatory responseInterleukin-1 betaHomo sapiens (human)
positive regulation of p38MAPK cascadeInterleukin-1 betaHomo sapiens (human)
positive regulation of non-canonical NF-kappaB signal transductionInterleukin-1 betaHomo sapiens (human)
positive regulation of RNA biosynthetic processInterleukin-1 betaHomo sapiens (human)
regulation of establishment of endothelial barrierInterleukin-1 betaHomo sapiens (human)
negative regulation of gap junction assemblyInterleukin-1 betaHomo sapiens (human)
positive regulation of T-helper 1 cell cytokine productionInterleukin-1 betaHomo sapiens (human)
negative regulation of extrinsic apoptotic signaling pathway in absence of ligandInterleukin-1 betaHomo sapiens (human)
cellular response to lipopolysaccharideInterleukin-1 betaHomo sapiens (human)
positive regulation of immature T cell proliferation in thymusInterleukin-1 betaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Processvia Protein(s)Taxonomy
cytokine activityInterleukin-1 betaHomo sapiens (human)
interleukin-1 receptor bindingInterleukin-1 betaHomo sapiens (human)
integrin bindingInterleukin-1 betaHomo sapiens (human)
protein bindingInterleukin-1 betaHomo sapiens (human)
protein domain specific bindingInterleukin-1 betaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (5)

Processvia Protein(s)Taxonomy
extracellular spaceInterleukin-1 betaHomo sapiens (human)
extracellular regionInterleukin-1 betaHomo sapiens (human)
extracellular spaceInterleukin-1 betaHomo sapiens (human)
lysosomeInterleukin-1 betaHomo sapiens (human)
cytosolInterleukin-1 betaHomo sapiens (human)
secretory granuleInterleukin-1 betaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (6)

Assay IDTitleYearJournalArticle
AID311774Growth inhibition of human NCI-H460 cells2007Journal of natural products, Nov, Volume: 70, Issue:11
The berkeleyacetals, three meroterpenes from a deep water acid mine waste Penicillium.
AID1502660Inhibition of LPS-induced nitric oxide production in mouse RAW264.7 cells at 80 uM after 24 hrs by Griess assay relative to control2017Journal 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.
AID311772Inhibition of MMP32007Journal of natural products, Nov, Volume: 70, Issue:11
The berkeleyacetals, three meroterpenes from a deep water acid mine waste Penicillium.
AID627038Induction of IL-1 beta production in LPS-induced human THP-1 cells by ELISA2011Journal 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.
AID627036Inhibition of caspase1 in differentiated human THP-1 cells at 100 ug/ml after 24 hrs by fluorometric assay2011Journal 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.
AID311773Inhibition of caspase 12007Journal 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]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's3 (50.00)29.6817
2010's3 (50.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.56

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.

MetricThis Compound (vs All)
Research Demand Index12.56 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.51 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.56)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other6 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
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