Details
Stereochemistry | ACHIRAL |
Molecular Formula | C10H6Cl2N2O2 |
Molecular Weight | 257.073 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[O-][N+](=O)C1=C(C=CC=C1Cl)C2=CNC=C2Cl
InChI
InChIKey=QJBZDBLBQWFTPZ-UHFFFAOYSA-N
InChI=1S/C10H6Cl2N2O2/c11-8-3-1-2-6(10(8)14(15)16)7-4-13-5-9(7)12/h1-5,13H
Molecular Formula | C10H6Cl2N2O2 |
Molecular Weight | 257.073 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: http://www.ncbi.nlm.nih.gov/pubmed/4310080Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/5785951
Sources: http://www.ncbi.nlm.nih.gov/pubmed/4310080
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/5785951
Pyrrolnitrin is an antifungal antibiotic and is most active against dermatophytic fungi, especially the species of Trichophyton. Fist, physical and chemical properties of pyrrolnitrin was described by Arima et al. It is synthesized from tryptophan, and the synthesis is probably initiated by a chloroperoxidase enzyme system acting on tryptophan. The present report deals with the mechanism of action of pyrrolnitrin. Pseudomonas pyrrocinia and other Pseudomonas species produce pyrrolnitrin from tryptophan as secondary metabolite. Pyrrolnitrin inhibits fungal growth by inhibiting the respiratory electron transport system.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: GO:0022904 Sources: http://www.ncbi.nlm.nih.gov/pubmed/4310080 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Sources: https://www.ncbi.nlm.nih.gov/pubmed/5785951 |
Curative | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Screening for new compounds with antiherpes activity. | 1984 Oct |
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Pyrrolnitrin and related pyrroles endowed with antibacterial activities against Mycobacterium tuberculosis. | 1998 Oct 20 |
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Genetic Diversity of phlD from 2,4-Diacetylphloroglucinol-Producing Fluorescent Pseudomonas spp. | 2001 Jan |
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Polymorphisms within the prnD and pltC genes from pyrrolnitrin and pyoluteorin-producing Pseudomonas and Burkholderia spp. | 2003 Feb 1 |
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PCR-based identification and characterization of Burkholderia cepacia complex bacteria from clinical and environmental sources. | 2004 |
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Crystallization and X-ray diffraction of a halogenating enzyme, tryptophan 7-halogenase, from Pseudomonas fluorescens. | 2004 Aug |
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A novel halogenase gene from the pentachloropseudilin producer Actinoplanes sp. ATCC 33002 and detection of in vitro halogenase activity. | 2004 Aug 15 |
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[Tryptophan 7-halogenase from Pseudomonas aureofaciens ACN strain: gene cloning and sequencing and the enzyme expression]. | 2004 Jul-Aug |
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Cloning and sequencing of the gene of tryptophan-7-halogenase from Pseudomonas fluorescens strain CHA0. | 2004 Jun |
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Use of green fluorescent protein-based reporters to monitor balanced production of antifungal compounds in the biocontrol agent Pseudomonas fluorescens CHA0. | 2005 |
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Residue level, persistence, and storage performance of citrus fruit treated with fludioxonil. | 2005 Aug 24 |
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Three Prochlorococcus cyanophage genomes: signature features and ecological interpretations. | 2005 May |
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Reconstitution and characterization of aminopyrrolnitrin oxygenase, a Rieske N-oxygenase that catalyzes unusual arylamine oxidation. | 2005 Nov 4 |
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Evaluation of Bacterial Antagonists for Biological Control of Broccoli Head Rot Caused by Pseudomonas fluorescens. | 2006 Apr |
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Recent developments in enzymatic chlorination. | 2006 Apr |
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Mechanistic studies on the conversion of arylamines into arylnitro compounds by aminopyrrolnitrin oxygenase: identification of intermediates and kinetic studies. | 2006 Jan 16 |
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Detection of antibiotic-related genes from bacterial biocontrol agents with polymerase chain reaction. | 2006 May |
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Preliminary crystallographic characterization of PrnB, the second enzyme in the pyrrolnitrin biosynthetic pathway. | 2006 Nov 1 |
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Probing the substrate specificity of aminopyrrolnitrin oxygenase (PrnD) by mutational analysis. | 2006 Sep |
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Quorum-sensing signaling is required for production of the antibiotic pyrrolnitrin in a rhizospheric biocontrol strain of Serratia plymuthica. | 2007 May |
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Characterization of CMR5c and CMR12a, novel fluorescent Pseudomonas strains from the cocoyam rhizosphere with biocontrol activity. | 2007 Oct |
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The second enzyme in pyrrolnitrin biosynthetic pathway is related to the heme-dependent dioxygenase superfamily. | 2007 Oct 30 |
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Acetylcholinesterase-inhibiting activity of pyrrole derivatives from a novel marine gliding bacterium, Rapidithrix thailandica. | 2008 |
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Characterization of a new isolate of Pseudomonas fluorescens strain Psd as a potential biocontrol agent. | 2008 Aug |
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Assessment of genetic and functional diversity of phosphate solubilizing fluorescent pseudomonads isolated from rhizospheric soil. | 2008 Dec 20 |
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Novel oxidized derivatives of antifungal pyrrolnitrin from the bacterium Burkholderia cepacia K87. | 2008 Jul |
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Sensing of oxygen in microtiter plates: a novel tool for screening drugs against pathogenic yeasts. | 2008 Jul |
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Overlapping protein-encoding genes in Pseudomonas fluorescens Pf0-1. | 2008 Jun 13 |
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Genetic and functional diversity among fluorescent pseudomonads isolated from the rhizosphere of banana. | 2008 Oct |
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Halogenase genes in nonribosomal peptide synthetase gene clusters of Microcystis (cyanobacteria): sporadic distribution and evolution. | 2008 Sep |
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Antifungal activity of selected indigenous pseudomonas and bacillus from the soybean rhizosphere. | 2009 |
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Proteomic detection of non-annotated protein-coding genes in Pseudomonas fluorescens Pf0-1. | 2009 Dec 24 |
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Genomics of pyrrolnitrin biosynthetic loci: evidence for conservation and whole-operon mobility within gram-negative bacteria. | 2009 Jan |
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Mobile genetic elements in the genome of the beneficial rhizobacterium Pseudomonas fluorescens Pf-5. | 2009 Jan 13 |
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Differential effectiveness of Serratia plymuthica IC1270-induced systemic resistance against hemibiotrophic and necrotrophic leaf pathogens in rice. | 2009 Jan 22 |
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Production of the antifungal compound pyrrolnitrin is quorum sensing-regulated in members of the Burkholderia cepacia complex. | 2009 Jun |
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Synthesis of pyrrolnitrin and related halogenated phenylpyrroles. | 2009 Mar 5 |
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Effects of nutrients on quorum signals and secondary metabolite productions of Burkholderia sp. O33. | 2009 Oct |
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Specific rhizosphere bacterial and fungal groups respond differently to elevated atmospheric CO(2). | 2009 Oct |
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Design, synthesis, and fungicidal activity of novel analogues of pyrrolnitrin. | 2009 Sep 9 |
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Phenazines are not essential for Pseudomonas chlororaphis PA23 biocontrol of Sclerotinia sclerotiorum, but do play a role in biofilm formation. | 2010 Jan |
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Chemical, physical and biological approaches to prevent ochratoxin induced toxicoses in humans and animals. | 2010 Jul |
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Combination of fluorescent reporters for simultaneous monitoring of root colonization and antifungal gene expression by a biocontrol pseudomonad on cereals with flow cytometry. | 2010 Jul |
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The ternary complex of PrnB (the second enzyme in the pyrrolnitrin biosynthesis pathway), tryptophan, and cyanide yields new mechanistic insights into the indolamine dioxygenase superfamily. | 2010 Jul 2 |
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Evaluation of multiple plant growth promoting traits of an isolate of Pseudomonas fluorescens strain Psd. | 2010 Jun |
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Effects of pesticides on the bacterial production of pyrrolnitrin. | 2010 May 12 |
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Beneficial bacteria of agricultural importance. | 2010 Nov |
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Microsatellite stability in the plant pathogen Botrytis cinerea after exposure to different selective pressures. | 2010 Nov-Dec |
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T4 genes in the marine ecosystem: studies of the T4-like cyanophages and their role in marine ecology. | 2010 Oct 28 |
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Gene expression enabling synthetic diversification of natural products: chemogenetic generation of pacidamycin analogs. | 2010 Sep 8 |
Patents
Sample Use Guides
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/6221376
Pyrrolnitrin caused drastic swelling of mitochondria in isotonic solutions of alkali metal salts and of sucrose without any addition of substrate for the respiratory chain in mitochondria. The swelling induced by pyrrolnitrin was characterized by a biphasic swelling process; a very fast initial swelling and thereafter a very slow speed secondary swelling. The increase of pyrrolnitrin concentration exponentially increased the magnitude of over-all rapid swelling. Pyrrolnitrin enhance the latent ATPase activity of mitochondria at the similar range of concentrations to those needed for the induction of the swelling. The concentrations of pyrrolnitrin where mitochondrial swelling was induced were found to be far lower than those needed for the exhibition of inhibitory effect on the electron transport system of mitochondria.
Substance Class |
Chemical
Created
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Record UNII |
N0P24B6EDQ
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Record Status |
Validated (UNII)
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D01AA07
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NCI_THESAURUS |
C514
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QD01AA07
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PYRROLNITRIN
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