Pyrrolnitrin

Pyrrolnitrin

Names
IUPAC name 3-chloro-4-(3-chloro-2-nitrophenyl)-1H-pyrrole
Identifiers
CAS Number	1018-71-9
ChEBI	CHEBI:32079
ChemSpider	13314
EC Number	213-812-7
Jmol 3D model	Interactive image
KEGG	D01094
MeSH	D011764
PubChem	13916
UNII	N0P24B6EDQ
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

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]

References

1. Gordee, R. S.; Matthews, T. R. (1969). "Systemic antifungal activity of pyrrolnitrin". Applied microbiology 17 (5): 690–694. 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". doi:10.1002/047126363X.agr106.
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.