Compounds > bromodeoxytopsentin
Page last updated: 2024-12-08

bromodeoxytopsentin

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

Description

bromodeoxytopsentin: from sponge Topsentia pachastrelloides; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

bromodeoxytopsentin : An aromatic ketone that is imidazole which is substituted by a 1H-indole-3-carbonyl group and a 6-bromo-1H-indol-3-yl group at positions 2 and 4, respectively. Isolated from the Mediterranean shallow-water sponge, Topsentia genetrix. It is a potent inhibitor of MRSA pyruvate kinase and exhibits antibacterial 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]

Cross-References

ID SourceID
PubMed CID400452
CHEMBL ID198814
CHEBI ID144087
SCHEMBL ID17537615
MeSH IDM000606902

Synonyms (12)

Synonym
bromodeoxytopsentin
NCI60_039303
nsc-712184
nsc712184
[5-(6-bromo-1h-indol-3-yl)-1h-imidazol-2-yl]-(1h-indol-3-yl)methanone
CHEMBL198814
CHEBI:144087
180633-55-0
[4-(6-bromo-1h-indol-3-yl)-1h-imidazol-2-yl](1h-indol-3-yl)methanone
[5-(6-bromo-1h-indol-3-yl)-1h-imidazol-2-yl](1h-indol-3-yl)methanone
SCHEMBL17537615
bdbm50210344
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
antibacterial agentA substance (or active part thereof) that kills or slows the growth of bacteria.
marine metaboliteAny metabolite produced during a metabolic reaction in marine macro- and microorganisms.
EC 2.7.1.40 (pyruvate kinase) inhibitorAn EC 2.7.1.* (phosphotransferases with an alcohol group as acceptor) inhibitor that interferes with the action of pyruvate kinase (EC 2.7.1.40).
[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 (4)

ClassDescription
imidazolesA five-membered organic heterocycle containing two nitrogen atoms at positions 1 and 3, or any of its derivatives; compounds containing an imidazole skeleton.
bromoindoleAn organobromine compound that is a compound based on an indole skeleton, containing one or more bromine atoms.
aromatic ketoneA ketone in which the carbonyl group is attached to an aromatic ring.
indole alkaloidAn alkaloid containing an indole skeleton.
[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)
Pyruvate kinaseStaphylococcus aureus subsp. aureus MRSA252IC50 (µMol)0.06000.06000.06000.0600AID1337460
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (26)

Assay IDTitleYearJournalArticle
AID255501Minimum inhibitory concentration against Staphylococcus aureus Newman strain2005Bioorganic & medicinal chemistry letters, Nov-15, Volume: 15, Issue:22
Bis(indole) alkaloids as sortase A inhibitors from the sponge Spongosorites sp.
AID379484Cytotoxicity against human K-562 cells1999Journal of natural products, Apr, Volume: 62, Issue:4
New Bis(Indole) alkaloids of the topsentin class from the sponge spongosorites genitrix
AID401682Cytotoxicity against human HCT15 cells after 48 hrs by SRB assay2005Journal of natural products, May, Volume: 68, Issue:5
Cytotoxic bisindole alkaloids from a marine sponge Spongosorites sp.
AID1608395Inhibition of methicillin-resistant Staphylococcus aureus pyruvate kinase2019Bioorganic & medicinal chemistry, 09-01, Volume: 27, Issue:17
Natural product derived promising anti-MRSA drug leads: A review.
AID1225233Selectivity ratio for recombinant his-tagged methicillin-resistant Staphylococcus aureus pyruvate kinase over recombinant his-tagged human pyruvate kinase M12015Journal of natural products, Mar-27, Volume: 78, Issue:3
Synthetic analogues of the marine bisindole deoxytopsentin: potent selective inhibitors of MRSA pyruvate kinase.
AID1225236Selectivity ratio for recombinant his-tagged methicillin-resistant Staphylococcus aureus pyruvate kinase over recombinant his-tagged human pyruvate kinase L2015Journal of natural products, Mar-27, Volume: 78, Issue:3
Synthetic analogues of the marine bisindole deoxytopsentin: potent selective inhibitors of MRSA pyruvate kinase.
AID1337465Selectivity ratio for inhibition of recombinant N-terminal His-tagged methicillin-resistant Staphylococcus aureus MRSA252 pyruvate kinase over inhibition of human recombinant N-terminal His-tagged pyruvate kinase M12017European journal of medicinal chemistry, Jan-05, Volume: 125Further investigation of inhibitors of MRSA pyruvate kinase: Towards the conception of novel antimicrobial agents.
AID1337460Inhibition of recombinant N-terminal His-tagged methicillin-resistant Staphylococcus aureus MRSA252 pyruvate kinase expressed in Escherichia coli BL21(DE3) using PEP as substrate measured after 5 mins by LDH-coupled assay2017European journal of medicinal chemistry, Jan-05, Volume: 125Further investigation of inhibitors of MRSA pyruvate kinase: Towards the conception of novel antimicrobial agents.
AID1337464Antibacterial activity against methicillin-resistant Staphylococcus aureus MRSA252 by two-fold microbroth dilution method2017European journal of medicinal chemistry, Jan-05, Volume: 125Further investigation of inhibitors of MRSA pyruvate kinase: Towards the conception of novel antimicrobial agents.
AID1225237Antibacterial activity against methicillin-susceptible Staphylococcus aureus RN4220 by 2-fold serial broth microdilution method2015Journal of natural products, Mar-27, Volume: 78, Issue:3
Synthetic analogues of the marine bisindole deoxytopsentin: potent selective inhibitors of MRSA pyruvate kinase.
AID401681Cytotoxicity against human XF498 cells after 48 hrs by SRB assay2005Journal of natural products, May, Volume: 68, Issue:5
Cytotoxic bisindole alkaloids from a marine sponge Spongosorites sp.
AID1225235Selectivity ratio for recombinant his-tagged methicillin-resistant Staphylococcus aureus pyruvate kinase over recombinant his-tagged human pyruvate kinase R2015Journal of natural products, Mar-27, Volume: 78, Issue:3
Synthetic analogues of the marine bisindole deoxytopsentin: potent selective inhibitors of MRSA pyruvate kinase.
AID1337468Selectivity ratio for inhibition of recombinant N-terminal His-tagged methicillin-resistant Staphylococcus aureus MRSA252 pyruvate kinase over inhibition of human recombinant N-terminal His-tagged pyruvate kinase-L2017European journal of medicinal chemistry, Jan-05, Volume: 125Further investigation of inhibitors of MRSA pyruvate kinase: Towards the conception of novel antimicrobial agents.
AID1858707Inhibition of Methicillin-resistant Staphylococcus aureus pyruvate kinase assessed as measuring absorbance of NADH coupled to L-LDH using phospho enol pyruvate in presence of ADP by spectrophotometry2021European journal of medicinal chemistry, Jan-01, Volume: 209Tryptophan derived natural marine alkaloids and synthetic derivatives as promising antimicrobial agents.
AID401679Cytotoxicity against human SKOV3 cells after 48 hrs by SRB assay2005Journal of natural products, May, Volume: 68, Issue:5
Cytotoxic bisindole alkaloids from a marine sponge Spongosorites sp.
AID1858679Antimicrobial activity against methicillin-resistant Staphylococcus aureus assessed as microbial growth inhibition by broth microdilution method2021European journal of medicinal chemistry, Jan-01, Volume: 209Tryptophan derived natural marine alkaloids and synthetic derivatives as promising antimicrobial agents.
AID1225224Inhibition of recombinant his-tagged methicillin-resistant Staphylococcus aureus pyruvate kinase expressed in Escherichia coli BL-21(DE3) using PEP as substrate after 5 mins by L-LDH coupled assay2015Journal of natural products, Mar-27, Volume: 78, Issue:3
Synthetic analogues of the marine bisindole deoxytopsentin: potent selective inhibitors of MRSA pyruvate kinase.
AID401678Cytotoxicity against human A549 cells after 48 hrs by SRB assay2005Journal of natural products, May, Volume: 68, Issue:5
Cytotoxic bisindole alkaloids from a marine sponge Spongosorites sp.
AID254837Inhibitory activity against Sortase A from Staphylococcus aureus2005Bioorganic & medicinal chemistry letters, Nov-15, Volume: 15, Issue:22
Bis(indole) alkaloids as sortase A inhibitors from the sponge Spongosorites sp.
AID1225238Antibacterial activity against methicillin-resistant Staphylococcus aureus 252 by 2-fold serial broth microdilution method2015Journal of natural products, Mar-27, Volume: 78, Issue:3
Synthetic analogues of the marine bisindole deoxytopsentin: potent selective inhibitors of MRSA pyruvate kinase.
AID1608394Antibacterial activity against methicillin-resistant Staphylococcus aureus2019Bioorganic & medicinal chemistry, 09-01, Volume: 27, Issue:17
Natural product derived promising anti-MRSA drug leads: A review.
AID1337466Selectivity ratio for inhibition of recombinant N-terminal His-tagged methicillin-resistant Staphylococcus aureus MRSA252 pyruvate kinase over inhibition of human recombinant N-terminal His-tagged pyruvate kinase M22017European journal of medicinal chemistry, Jan-05, Volume: 125Further investigation of inhibitors of MRSA pyruvate kinase: Towards the conception of novel antimicrobial agents.
AID1337467Selectivity ratio for inhibition of recombinant N-terminal His-tagged methicillin-resistant Staphylococcus aureus MRSA252 pyruvate kinase over inhibition of human recombinant N-terminal His-tagged pyruvate kinase-R2017European journal of medicinal chemistry, Jan-05, Volume: 125Further investigation of inhibitors of MRSA pyruvate kinase: Towards the conception of novel antimicrobial agents.
AID1225234Selectivity ratio for recombinant his-tagged methicillin-resistant Staphylococcus aureus pyruvate kinase over recombinant his-tagged human pyruvate kinase M22015Journal of natural products, Mar-27, Volume: 78, Issue:3
Synthetic analogues of the marine bisindole deoxytopsentin: potent selective inhibitors of MRSA pyruvate kinase.
AID401693Cytotoxicity against human K562 cells2005Journal of natural products, May, Volume: 68, Issue:5
Cytotoxic bisindole alkaloids from a marine sponge Spongosorites sp.
AID401680Cytotoxicity against human SK-MEL-2 cells after 48 hrs by SRB assay2005Journal of natural products, May, Volume: 68, Issue:5
Cytotoxic bisindole alkaloids from a marine sponge Spongosorites sp.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (12.50)18.2507
2000's2 (25.00)29.6817
2010's3 (37.50)24.3611
2020's2 (25.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.73

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 Index12.73 (24.57)
Research Supply Index2.20 (2.92)
Research Growth Index4.93 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.73)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (25.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other6 (75.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
vancomycin
Vancomycin: Antibacterial obtained from Streptomyces orientalis. It is a glycopeptide related to RISTOCETIN that inhibits bacterial cell wall assembly and is toxic to kidneys and the inner ear.. vancomycin : A complex glycopeptide from Streptomyces orientalis. It inhibits a specific step in the synthesis of the peptidoglycan layer in the Gram-positive bacteria Staphylococcus aureus and Clostridium difficile.		3.3110glycopeptideantibacterial drug;
antimicrobial agent;
bacterial metabolite
topsentin
topsentin: structure given in first source; a marine natural product		2.0210
tetrandrine
tetrandrine: a bisbenzylisoquinoline that exhibits antifibrogenic activity		3.3110bisbenzylisoquinoline alkaloid;
isoquinolines
fangchinoline
[no description available]		3.3110aromatic ether;
bisbenzylisoquinoline alkaloid;
macrocycle		anti-HIV-1 agent;
anti-inflammatory agent;
antineoplastic agent;
antioxidant;
neuroprotective agent;
plant metabolite
imipenem, anhydrous
Imipenem: Semisynthetic thienamycin that has a wide spectrum of antibacterial activity against gram-negative and gram-positive aerobic and anaerobic bacteria, including many multiresistant strains. It is stable to beta-lactamases. Clinical studies have demonstrated high efficacy in the treatment of infections of various body systems. Its effectiveness is enhanced when it is administered in combination with CILASTATIN, a renal dipeptidase inhibitor.. imipenem : A broad-spectrum, intravenous beta-lactam antibiotic of the carbapenem subgroup.		2.0210beta-lactam antibiotic allergen;
carbapenems;
zwitterion		antibacterial drug
aspidin bb
[no description available]		3.3110
brevianamide f
brevianamide F: isolated from the endophyte from Aspergillus fumigatus associated with Melia azedarach L that could be used to develop a natural eco-friendly herbicide.structure in first source. brevianamide F : A pyrrolopyrazine that is hexahydropyrrolo[1,2-a]pyrazine-1,4-dione bearing an indol-3-ylmethyl substituent at position 3 (the 3S,8aS-diastereomer, obtained by formal cyclocondensation of L-tryptophan and L-proline).		3.4110dipeptide;
indoles;
pyrrolopyrazine		metabolite
topsentin a
topsentin A: number of carbony group = 1 for topsentin A and no carbonyl group for nortopsentin B and D; structure in first source		2.7330
meropenem
Meropenem: A thienamycin derivative antibacterial agent that is more stable to renal dehydropeptidase I than IMIPENEM, but does not need to be given with an enzyme inhibitor such as CILASTATIN. It is used in the treatment of bacterial infections, including infections in immunocompromised patients.. meropenem : A carbapenemcarboxylic acid in which the azetidine and pyrroline rings carry 1-hydroxymethyl and in which the azetidine and pyrroline rings carry 1-hydroxymethyl and 5-(dimethylcarbamoyl)pyrrolidin-3-ylthio substituents respectively.		2.0210alpha,beta-unsaturated monocarboxylic acid;
carbapenemcarboxylic acid;
organic sulfide;
pyrrolidinecarboxamide		antibacterial agent;
antibacterial drug;
drug allergen
deformylflustrabromine
deformylflustrabromine: has antineoplastic activity; isolated from Flustra folicea; structure in first source		3.4110tryptamines
luteolin
[no description available]		3.31103'-hydroxyflavonoid;
tetrahydroxyflavone		angiogenesis inhibitor;
anti-inflammatory agent;
antineoplastic agent;
apoptosis inducer;
c-Jun N-terminal kinase inhibitor;
EC 2.3.1.85 (fatty acid synthase) inhibitor;
immunomodulator;
nephroprotective agent;
plant metabolite;
radical scavenger;
vascular endothelial growth factor receptor antagonist
quercetin 3-o-methyl ether
quercetin 3-O-methyl ether: from Rhamnus species; structure in first source. 3',4',5,7-tetrahydroxy-3-methoxyflavone : A tetrahydroxyflavone having the 4-hydroxy groups located at the 3'- 4'- 5- and 7-positions as well as a methoxy group at the 2-position.		3.3110monomethoxyflavone;
tetrahydroxyflavone		antimicrobial agent;
metabolite
lyoniside
daucosterol : A steroid saponin that is sitosterol attached to a beta-D-glucopyranosyl residue at position 3 via a glycosidic linkage. It has bee isolated from Panax japonicus var. major and Breynia fruticosa.		2.0210beta-D-glucoside;
monosaccharide derivative;
steroid saponin		plant metabolite
flustramine c
flustramine C: structure in first source		3.4110
fumiquinazoline f
fumiquinazoline F: structure in first source. fumiquinazoline F : A fumiquinazoline that consists of pyrazino[2,1-b]quinazoline-3,6(1H,4H)-dione bearing a methyl substituent at position 1 and an indol-3-yl group at position 4.		3.4110fumiquinazoline;
indoles;
pyrazinoquinazoline
ConditionIndicatedRelationship StrengthStudiesTrials