Page last updated: 2024-12-06

showdomycin

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Showdomycin: 3-beta-D-Ribofuranosylmaleimide. Antineoplastic antibiotic isolated from Streptomyces showdoensis. It is possibly active also as a sulfhydryl reagent. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID28032
CHEMBL ID5207810
SCHEMBL ID196208
MeSH IDM0019804
PubMed CID261131
CHEMBL ID1705403
SCHEMBL ID2391572
MeSH IDM0019804

Synonyms (39)

Synonym
nsc 93047
brn 0538225
d-showdomycin
3-beta-d-ribofuranosyl-1h-pyrrole-2,5-dione
2-beta-d-ribofuranosylmaleimide
maleimide, 2-beta-d-ribofuranosyl-
3-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrrole-2,5-dione
showdomycin
unii-e1v8315qhy
e1v8315qhy ,
3-.beta.-d-ribofuranosyl-1h-pyrrole-2,5-dione
2-.beta.-d-ribofuranosylmaleimide
showdomycin [mi]
SCHEMBL196208
3-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1h-pyrrole-2,5-dione
Q27276755
3-((2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1h-pyrrole-2,5-dione
DTXSID001043162
AKOS040749494
CHEMBL5207810
smr001561078
NCI60_042070
1h-pyrrole-2,5-dione, 3-beta-d-ribofuranosyl-
1h-pyrrole-2,5-dione, 3-.beta.-d-ribofuranosyl-
16755-07-0
NSC93047 ,
mls002695166 ,
nsc-93047
maleimide, 5-.beta.-d-ribofuranosyl-
1h-pyrrole-2, 3-.beta.-d-ribofuranosyl-
ZINC01482170
3-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrrole-2,5-dione
NCGC00246900-01
maleimide, 2-.beta.-d-ribofuranosyl-
3-pyrroline-2,5-dione, 3-.beta.-d-ribofuranosyl-
FFLUMYXAPXARJP-UHFFFAOYSA-N
SCHEMBL2391572
CHEMBL1705403
3-beta-d-ribofuranosylpyrrole-2,5-dione

Research Excerpts

Overview

Showdomycin is a C-nucleoside bearing an electrophilic maleimide base. It inhibits the nucleic acid synthesis in bacteria.

ExcerptReferenceRelevance
"Showdomycin is a C-nucleoside bearing an electrophilic maleimide base. "( Identification of a Pyrrole Intermediate Which Undergoes C-Glycosidation and Autoxidation to Yield the Final Product in Showdomycin Biosynthesis.
Kim, M; Liu, HW; Ren, D; Wang, SA, 2021
)
2.27
"Showdomycin is a naturally maleimide antitumor antibiotic of the C-nucleoside, it inhibits the nucleic acid synthesis in bacteria. "( Conformational analysis (geometry optimization) of nucleosidic antitumor antibiotic showdomycin by Arguslab 4 software.
Akhtar, N; Bano, F; Bano, K; Ghafoor, NA; Naz, A, 2009
)
2.02
"Showdomycin is a potent nucleoside antibiotic that displays a high structural similarity to uridine and pseudouridine. "( Showdomycin as a versatile chemical tool for the detection of pathogenesis-associated enzymes in bacteria.
Böttcher, T; Sieber, SA, 2010
)
3.25
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (13)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, JmjC domain-containing histone demethylation protein 3AHomo sapiens (human)Potency35.48130.631035.7641100.0000AID504339
thioredoxin reductaseRattus norvegicus (Norway rat)Potency7.07950.100020.879379.4328AID588453
TDP1 proteinHomo sapiens (human)Potency5.56200.000811.382244.6684AID686978; AID686979
regulator of G-protein signaling 4Homo sapiens (human)Potency28.18380.531815.435837.6858AID504845
vitamin D3 receptor isoform VDRAHomo sapiens (human)Potency39.81070.354828.065989.1251AID504847
chromobox protein homolog 1Homo sapiens (human)Potency17.78280.006026.168889.1251AID540317
serine/threonine-protein kinase PLK1Homo sapiens (human)Potency26.67950.168316.404067.0158AID720504
urokinase-type plasminogen activator precursorMus musculus (house mouse)Potency22.38720.15855.287912.5893AID540303
plasminogen precursorMus musculus (house mouse)Potency22.38720.15855.287912.5893AID540303
urokinase plasminogen activator surface receptor precursorMus musculus (house mouse)Potency22.38720.15855.287912.5893AID540303
gemininHomo sapiens (human)Potency29.09290.004611.374133.4983AID624296; AID624297
DNA dC->dU-editing enzyme APOBEC-3G isoform 1Homo sapiens (human)Potency35.48130.058010.694926.6086AID602310
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
polyadenylate-binding protein 1Homo sapiens (human)IC50 (µMol)66.00004.910023.702976.1900AID602259; AID602260
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (23)

Assay IDTitleYearJournalArticle
AID1882855Cytotoxicity against HEK293T cells at 30 uM incubated for 24 hrs by LDH assay2022European journal of medicinal chemistry, Jul-05, Volume: 237The role of the maleimide ring system on the structure-activity relationship of showdomycin.
AID1882866Antibacterial activity against Escherichia coli K12 expressing modified luxABCDE genes assessed as reduction in bacterial growth by measuring reduction in bioluminescence at 0.002 to 2.5 mM incubated for 16 hrs by microplate reader analysis2022European journal of medicinal chemistry, Jul-05, Volume: 237The role of the maleimide ring system on the structure-activity relationship of showdomycin.
AID1882871Antibacterial activity against Escherichia coli K12 expressing modified luxABCDE genes assessed as reduction in bacterial growth by measuring reduction in bioluminescence at 0.002 to 2.5 mM incubated for 16 hrs in presence of uridine at 0.002 to 12.5 mM b2022European journal of medicinal chemistry, Jul-05, Volume: 237The role of the maleimide ring system on the structure-activity relationship of showdomycin.
AID1882867Bactericidal activity against Escherichia coli K12 expressing modified luxABCDE genes assessed as reduction in luminescence at 0.625 mM incubated for 16 hrs by microplate reader analysis2022European journal of medicinal chemistry, Jul-05, Volume: 237The role of the maleimide ring system on the structure-activity relationship of showdomycin.
AID1882870Antibacterial activity against Escherichia coli K12 expressing modified luxABCDE genes assessed as reduction in bacterial growth by measuring reduction in optical density at 0.002 to 2.5 mM incubated for 16 hrs in presence of uridine at 0.002 to 12.5 mM b2022European journal of medicinal chemistry, Jul-05, Volume: 237The role of the maleimide ring system on the structure-activity relationship of showdomycin.
AID1882869Antibacterial activity against Escherichia coli K12 expressing modified luxABCDE genes assessed as reduction in bacterial growth by measuring reduction in bioluminescence at low concentrations measured after 250 mins by microplate reader analysis2022European journal of medicinal chemistry, Jul-05, Volume: 237The role of the maleimide ring system on the structure-activity relationship of showdomycin.
AID1882859Cytotoxicity against HEK293T cells assessed as morphological changes at 30 uM2022European journal of medicinal chemistry, Jul-05, Volume: 237The role of the maleimide ring system on the structure-activity relationship of showdomycin.
AID1882857Cytotoxicity against HEK293T cells assessed as reduction in viable cells at 125 uM incubated for 24 hrs by CCK-8 assay2022European journal of medicinal chemistry, Jul-05, Volume: 237The role of the maleimide ring system on the structure-activity relationship of showdomycin.
AID1882865Antibacterial activity against Escherichia coli K12 expressing modified luxABCDE genes assessed as reduction in bacterial growth by measuring reduction in optical density at 0.002 to 2.5 mM incubated for 16 hrs by microplate reader analysis2022European journal of medicinal chemistry, Jul-05, Volume: 237The role of the maleimide ring system on the structure-activity relationship of showdomycin.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. 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.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1347086qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. 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.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1347083qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347082qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. 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.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (54)

TimeframeStudies, This Drug (%)All Drugs %
pre-199039 (72.22)18.7374
1990's5 (9.26)18.2507
2000's2 (3.70)29.6817
2010's4 (7.41)24.3611
2020's4 (7.41)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 22.44

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.

MetricThis Compound (vs All)
Research Demand Index22.44 (24.57)
Research Supply Index3.97 (2.92)
Research Growth Index4.77 (4.65)
Search Engine Demand Index23.28 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (22.44)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Trials0 (0.00%)5.53%
Reviews8 (15.38%)6.00%
Reviews0 (0.00%)6.00%
Case Studies1 (1.92%)4.05%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Observational0 (0.00%)0.25%
Other43 (82.69%)84.16%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]