Pyrrolnitrin

Pyrrolnitrin is an antifungal antibiotic.[1] Pseudomonas pyrrocinia and other Pseudomonas species produce pyrrolnitrin from tryptophan as secondary metabolite.[2][3] The fungicides fenpiclonil and fludioxonil are chemically related to pyrrolnitrin.[4][5]

Pyrrolnitrin

Names
IUPAC name 3-chloro-4-(3-chloro-2-nitrophenyl)-1H-pyrrole
Identifiers
CAS Number	1018-71-9
3D model (JSmol)	Interactive image
ChEBI	CHEBI:32079
ChemSpider	13314
ECHA InfoCard	100.012.557
EC Number	213-812-7
KEGG	D01094
MeSH	D011764
PubChem CID	13916
UNII	N0P24B6EDQ
CompTox Dashboard (EPA)	DTXSID9046867
InChI InChI=1S/C10H6Cl2N2O2/c11-8-3-1-2-6(10(8)14(15)16)7-4-13-5-9(7)12/h1-5,13H Key: QJBZDBLBQWFTPZ-UHFFFAOYSA-N InChI=1/C10H6Cl2N2O2/c11-8-3-1-2-6(10(8)14(15)16)7-4-13-5-9(7)12/h1-5,13H Key: QJBZDBLBQWFTPZ-UHFFFAOYAG
SMILES C1=CC(=C(C(=C1)Cl)[N+](=O)[O-])C2=CNC=C2Cl
Properties
Chemical formula	C10H6Cl2N2O2
Molar mass	257.07284
Pharmacology
ATC code	D01AA07 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

References

1. Gordee, R. S.; Matthews, T. R. (1969). "Systemic antifungal activity of pyrrolnitrin". Applied Microbiology. 17 (5): 690–694. doi:10.1128/AEM.17.5.690-694.1969. PMC 377781. PMID 5785951.
2. Zhu, X.; Van Pee, K. -H.; Naismith, J. H. (2010). "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". Journal of Biological Chemistry. 285 (27): 21126–21133. doi:10.1074/jbc.M110.120485. PMC 2898318. PMID 20421301.
3. Park, J. Y.; Oh, S. A.; Anderson, A. J.; Neiswender, J.; Kim, J. -C.; Kim, Y. C. (2011). "Production of the antifungal compounds phenazine and pyrrolnitrin from Pseudomonas chlororaphis O6 is differentially regulated by glucose". Letters in Applied Microbiology. 52 (5): 532–537. doi:10.1111/j.1472-765X.2011.03036.x. PMID 21362001.
4. Pillonel, Ch; Knauf-beiter, G.; Steinemann, A. (2003). "Fungicides, Phenylpyrroles". Encyclopedia of Agrochemicals. doi:10.1002/047126363X.agr106. ISBN 047126363X.
5. Jespers, A.B.K.; Davidse, L.C.; Dewaard, M.A. (1993). "Biochemical Effects of the Phenylpyrrole Fungicide Fenpiclonil in Fusarium sulphureum (Schlecht)". Pesticide Biochemistry and Physiology. 45 (2): 116–129. doi:10.1006/pest.1993.1014. ISSN 0048-3575.