Compounds > aureothricin
Page last updated: 2024-11-06

aureothricin

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Description

Aureothricin is a polyketide antibiotic produced by the bacterium *Streptomyces thioluteus*. It exhibits antibacterial activity against Gram-positive bacteria, including *Staphylococcus aureus*, *Bacillus subtilis*, and *Streptococcus pyogenes*. The compound is characterized by its unique chemical structure containing a macrocyclic lactone ring system. Aureothricin\\'s mechanism of action is believed to involve inhibition of bacterial protein synthesis. It is a potent inhibitor of the bacterial enzyme peptidyl transferase, which is crucial for protein synthesis. The compound is also known to exhibit antifungal activity. It is studied for its potential therapeutic applications as an antibacterial and antifungal agent. While aureothricin has shown promise in vitro and in animal models, its clinical application is limited due to its poor bioavailability and toxicity.'

aureothricin: structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

aureothricin : A dithiolopyrrolone antibiotic that is 4,5-dihydro[1,2]dithiolo[4,3-b]pyrrole in which the hydrogens at positions 4,5 and 6 have been replaced by methyl, oxo and propanoylamino groups, respectively. It is a moderate antimicrobial by-product of the thiolutin fermentation in various Streptomyces species. [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 CID68460
CHEMBL ID1163542
CHEBI ID156452
SCHEMBL ID3515205
MeSH IDM0056389

Synonyms (29)

Synonym
aureothricin
propionopyrrothine
574-95-8
n-{4-methyl-5-oxo-4h,5h-[1,2]dithiolo[4,3-b]pyrrol-6- yl}propanamide
propanoyl-pyrrothine
4-methyl-6-propionamido-1,2-dithiolo[4,3-b]pyrrol-5(4h)-one
CHEBI:156452
n-(4-methyl-5-oxo-4,5-dihydro[1,2]dithiolo[4,3-b]pyrrol-6-yl)propanamide
n-(4,5-dihydro-4-methyl-5-oxo-1,2-dithiolo[4,3-b]pyrrol-6-yl)propionamide
n-(4-methyl-5-oxodithiolo[4,3-b]pyrrol-6-yl)propanamide
CHEMBL1163542
unii-0kx00l19q2
0kx00l19q2 ,
n-(4,5-dihydro-4-methyl-5-oxo-1,2-dithiolopyrrol-6-yl)-propanamide
4-methyl-6-propionamido-1,2-dithiolo(4,3-b)pyrrol-5(4h)-one
aureothricin [mi]
5-methyl-3-propionamidopyrrolin-4-one(4,3-d)-1,2-dithiole
SCHEMBL3515205
n-(4-methyl-5-oxo-4,5-dihydro-dithiolopyrrol-6-yl)propionamide
HB3786
DTXSID60205993
thiolutin, from streptomyces luteosporeus, >=95% (hplc)
BCP24202
CS-0083812
HY-N6737
Q27236918
MS-23430
n-(4-methyl-5-oxo-4,5-dihydro-[1,2]dithiolo[4,3-b]pyrrol-6-yl)propionamide
AKOS040741180
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (4)

RoleDescription
bacterial metaboliteAny prokaryotic metabolite produced during a metabolic reaction in bacteria.
angiogenesis inhibitorAn agent and endogenous substances that antagonize or inhibit the development of new blood vessels.
antibacterial agentA substance (or active part thereof) that kills or slows the growth of bacteria.
EC 2.7.7.6 (RNA polymerase) inhibitorAn EC 2.7.7.* (nucleotidyltransferase) inhibitor that interferes with the action of RNA polymerase (EC 2.7.7.6).
[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 (2)

ClassDescription
dithiolopyrrolone antibioticA class of antibiotics that possess the unique pyrrolinonodithiole (4H-[1,2]dithiolo[4,3-b]pyrrol-5-one) skeleton linked upto three variable acyl groups.
secondary carboxamideA carboxamide resulting from the formal condensation of a carboxylic acid with a primary amine; formula RC(=O)NHR(1).
[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]

Bioassays (20)

Assay IDTitleYearJournalArticle
AID487094Antimicrobial activity against Candida albicans IPA 200 after 48 to 72 hrs by agar dilution method2010Journal of natural products, Jun-25, Volume: 73, Issue:6
Dithiolopyrrolone antibiotic formation induced by adding valeric acid to the culture broth of Saccharothrix algeriensis.
AID487601Antimicrobial activity against Fusarium oxysporum f.sp. lini (Foln 3-5) after 48 to 72 hrs by agar dilution method2010Journal of natural products, Jun-25, Volume: 73, Issue:6
Dithiolopyrrolone antibiotic formation induced by adding valeric acid to the culture broth of Saccharothrix algeriensis.
AID486909Antimicrobial activity against Mucor ramannianus NRRL 1829 after 48 to 72 hrs by agar dilution method2010Journal of natural products, Jun-25, Volume: 73, Issue:6
Dithiolopyrrolone antibiotic formation induced by adding valeric acid to the culture broth of Saccharothrix algeriensis.
AID486910Antimicrobial activity against Penicillium expansum after 48 to 72 hrs by agar dilution method2010Journal of natural products, Jun-25, Volume: 73, Issue:6
Dithiolopyrrolone antibiotic formation induced by adding valeric acid to the culture broth of Saccharothrix algeriensis.
AID487092Antimicrobial activity against Fusarium culmorum after 48 to 72 hrs by agar dilution method2010Journal of natural products, Jun-25, Volume: 73, Issue:6
Dithiolopyrrolone antibiotic formation induced by adding valeric acid to the culture broth of Saccharothrix algeriensis.
AID486911Antimicrobial activity against Aspergillus carbonarius M333 after 48 to 72 hrs by agar dilution method2010Journal of natural products, Jun-25, Volume: 73, Issue:6
Dithiolopyrrolone antibiotic formation induced by adding valeric acid to the culture broth of Saccharothrix algeriensis.
AID486903Antimicrobial activity against Listeria monocytogenes CIP 82110 after 24 to 48 hrs by agar dilution method2010Journal of natural products, Jun-25, Volume: 73, Issue:6
Dithiolopyrrolone antibiotic formation induced by adding valeric acid to the culture broth of Saccharothrix algeriensis.
AID486906Antimicrobial activity against Salmonella enterica CIP 81.3 after 24 to 48 hrs by agar dilution method2010Journal of natural products, Jun-25, Volume: 73, Issue:6
Dithiolopyrrolone antibiotic formation induced by adding valeric acid to the culture broth of Saccharothrix algeriensis.
AID486905Antimicrobial activity against Klebsiella pneumoniae CIP 82.91 after 24 to 48 hrs by agar dilution method2010Journal of natural products, Jun-25, Volume: 73, Issue:6
Dithiolopyrrolone antibiotic formation induced by adding valeric acid to the culture broth of Saccharothrix algeriensis.
AID486908Antimicrobial activity against Agrobacterium tumefaciens no. 2410 LB after 24 to 48 hrs by agar dilution method2010Journal of natural products, Jun-25, Volume: 73, Issue:6
Dithiolopyrrolone antibiotic formation induced by adding valeric acid to the culture broth of Saccharothrix algeriensis.
AID486900Antimicrobial activity against Bacillus coagulans CIP 6625 after 24 to 48 hrs by agar dilution method2010Journal of natural products, Jun-25, Volume: 73, Issue:6
Dithiolopyrrolone antibiotic formation induced by adding valeric acid to the culture broth of Saccharothrix algeriensis.
AID486901Antimicrobial activity against Micrococcus luteus ATCC 9314 after 24 to 48 hrs by agar dilution method2010Journal of natural products, Jun-25, Volume: 73, Issue:6
Dithiolopyrrolone antibiotic formation induced by adding valeric acid to the culture broth of Saccharothrix algeriensis.
AID487090Antimicrobial activity against Fusarium moniliforme after 48 to 72 hrs by agar dilution method2010Journal of natural products, Jun-25, Volume: 73, Issue:6
Dithiolopyrrolone antibiotic formation induced by adding valeric acid to the culture broth of Saccharothrix algeriensis.
AID486899Antimicrobial activity against Bacillus subtilis ATCC 6633 after 24 to 48 hrs by agar dilution method2010Journal of natural products, Jun-25, Volume: 73, Issue:6
Dithiolopyrrolone antibiotic formation induced by adding valeric acid to the culture broth of Saccharothrix algeriensis.
AID487091Antimicrobial activity against Fusarium equiseti after 48 to 72 hrs by agar dilution method2010Journal of natural products, Jun-25, Volume: 73, Issue:6
Dithiolopyrrolone antibiotic formation induced by adding valeric acid to the culture broth of Saccharothrix algeriensis.
AID487093Antimicrobial activity against Fusarium graminearum after 48 to 72 hrs by agar dilution method2010Journal of natural products, Jun-25, Volume: 73, Issue:6
Dithiolopyrrolone antibiotic formation induced by adding valeric acid to the culture broth of Saccharothrix algeriensis.
AID486904Antimicrobial activity against Escherichia coli ATCC 10536 after 24 to 48 hrs by agar dilution method2010Journal of natural products, Jun-25, Volume: 73, Issue:6
Dithiolopyrrolone antibiotic formation induced by adding valeric acid to the culture broth of Saccharothrix algeriensis.
AID486907Antimicrobial activity against Pseudomonas aeruginosa CIP A22 after 24 to 48 hrs by agar dilution method2010Journal of natural products, Jun-25, Volume: 73, Issue:6
Dithiolopyrrolone antibiotic formation induced by adding valeric acid to the culture broth of Saccharothrix algeriensis.
AID487095Antimicrobial activity against Saccharomyces cerevisiae ATCC 4226 after 48 to 72 hrs by agar dilution method2010Journal of natural products, Jun-25, Volume: 73, Issue:6
Dithiolopyrrolone antibiotic formation induced by adding valeric acid to the culture broth of Saccharothrix algeriensis.
AID486902Antimicrobial activity against Staphylococcus aureus CIP 7625 after 24 to 48 hrs by agar dilution method2010Journal of natural products, Jun-25, Volume: 73, Issue:6
Dithiolopyrrolone antibiotic formation induced by adding valeric acid to the culture broth of Saccharothrix algeriensis.
[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-19904 (50.00)18.7374
1990's1 (12.50)18.2507
2000's0 (0.00)29.6817
2010's3 (37.50)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: 20.06

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 Index20.06 (24.57)
Research Supply Index2.20 (2.92)
Research Growth Index4.63 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (20.06)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (12.50%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other7 (87.50%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
methionine
Methionine: A sulfur-containing essential L-amino acid that is important in many body functions.. methionine : A sulfur-containing amino acid that is butyric acid bearing an amino substituent at position 2 and a methylthio substituent at position 4.		1.9710aspartate family amino acid;
L-alpha-amino acid;
methionine zwitterion;
methionine;
proteinogenic amino acid		antidote to paracetamol poisoning;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical
acetopyrrothine
acetopyrrothine: structure. thiolutin : A dithiolopyrrolone antibiotic that is 4,5-dihydro[1,2]dithiolo[4,3-b]pyrrole in which the hydrogens at positions 4,5 and 6 have been replaced by methyl, oxo and acetamido groups, respectively. It is a potent inhibitor of RNA polymerases, inhibits the angiogenesis of human umbilical vein endothelial cells, and also inhibits JAMM metalloproteases.		3.7630acetamides;
dithiolopyrrolone antibiotic		angiogenesis inhibitor;
antibacterial agent;
antifungal agent;
antineoplastic agent;
bacterial metabolite;
chelator;
EC 2.7.7.6 (RNA polymerase) inhibitor;
marine metabolite;
protein synthesis inhibitor;
toxin
pyrroles
1H-pyrrole : A tautomer of pyrrole that has the double bonds at positions 2 and 4.. pyrrole : A five-membered monocyclic heteroarene comprising one NH and four CH units which forms the parent compound of the pyrrole group of compounds. Its five-membered ring structure has three tautomers. A 'closed class'.. azole : Any monocyclic heteroarene consisting of a five-membered ring containing nitrogen. Azoles can also contain one or more other non-carbon atoms, such as nitrogen, sulfur or oxygen.		4.4470pyrrole;
secondary amine
ethionine
L-ethionine : An S-ethylhomocysteine that has S-configuration at the chiral centre.		1.9710S-ethylhomocysteineantimetabolite;
carcinogenic agent
mupirocin
Mupirocin: A topically used antibiotic from a strain of Pseudomonas fluorescens. It has shown excellent activity against gram-positive staphylococci and streptococci. The antibiotic is used primarily for the treatment of primary and secondary skin disorders, nasal infections, and wound healing.. mupirocin : An alpha,beta-unsaturated ester resulting from the formal condensation of the alcoholic hydroxy group of 9-hydroxynonanoic acid with the carboxy group of (2E)-4-[(2S)-tetrahydro-2H-pyran-2-yl]-3-methylbut-2-enoic acid in which the tetrahydropyranyl ring is substituted at positions 3 and 4 by hydroxy groups and at position 5 by a {(2S,3S)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl}methyl group. Originally isolated from the Gram-negative bacterium Pseudomonas fluorescens, it is used as a topical antibiotic for the treatment of Gram-positive bacterial infections.		3.1810alpha,beta-unsaturated carboxylic ester;
epoxide;
monocarboxylic acid;
oxanes;
secondary alcohol;
triol		antibacterial drug;
bacterial metabolite;
protein synthesis inhibitor
cysteine
Cysteine: A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.. L-cysteinium : The L-enantiomer of cysteinium.. cysteine : A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.		1.9710cysteiniumfundamental metabolite
thiomarinol
thiomarinol: an antimicrobial antibiotic isolated from Alteromonas rava; a hybrid of 2 antibiotics, a pseudomonic acid analog and holothin; structure in first source. thiomarinol A : An organosulfur heterocyclic compound produced by a marine bacterium Alteromonas rava and has been shown to exhibit antibacterial activity against Gram-positive and Gram-negative bacteria.		3.1810
holomycin
holomycin: structure. holomycin : A dithiolopyrrolone antibiotic that is 4,5-dihydro[1,2]dithiolo[4,3-b]pyrrole in which the hydrogens at positions 5 and 6 have been replaced by oxo and acetamido groups, respectively. It is an inhibitor of DNA-dependent RNA polymerase, and exhibits antibacterial and antitumour properties.		3.1810acetamides;
dithiolopyrrolone antibiotic		antibacterial agent;
antineoplastic agent;
bacterial metabolite;
chelator;
EC 2.7.7.6 (RNA polymerase) inhibitor;
marine metabolite
ConditionIndicatedRelationship StrengthStudiesTrials