Structure via PubChem · Public domain (PubChem)
pyrrolnitrin
Sign in to saveAlso known as 3-chloro-4-(2'-nitro-3'-chlorophenyl)pyrrole, 3-chloro-4-(3-chloro-2-nitrophenyl)pyrrole
Pyrrolnitrin (PRN) is a naturally occurring phenylpyrrole fungicide. Pseudomonas and Burkholderia species produce pyrrolnitrin from tryptophan as secondary metabolite. It is believed that the antifungal properties come from inhibition of electron transport system.
Chemical data
- Formula
- C10H6Cl2N2O2
- Molecular weight
- 257.07 g/mol
- IUPAC name
- 3-chloro-4-(3-chloro-2-nitrophenyl)-1H-pyrrole
- SMILES
- C1=CC(=C(C(=C1)Cl)[N+](=O)[O-])C2=CNC=C2Cl
- InChIKey
- QJBZDBLBQWFTPZ-UHFFFAOYSA-N
- XLogP
- 4.4
- Polar surface area
- 61.6 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
298 papersvia PubMed
Wikidata facts
- Mass
- 255.981
Show 6 more facts
- chemical formula
- C₁₀H₆Cl₂N₂O₂
- canonical SMILES
- C1=CC(=C(C(=C1)Cl)[N+](=O)[O-])C2=CNC=C2Cl
- World Health Organisation international non-proprietary name
- pyrrolnitrin
- subject has role
- antifungal
- found in taxon
- Pseudomonas
- Commons category
- Pyrrolnitrin
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
2 sectionsContents
- Biosynthesis
- References
Pyrrolnitrin (PRN) is a naturally occurring phenylpyrrole fungicide. Pseudomonas and Burkholderia species produce pyrrolnitrin from tryptophan as secondary metabolite. It is believed that the antifungal properties come from inhibition of electron transport system.
The synthetic fungicides fenpiclonil and fludioxonil are chemically related to pyrrolnitrin.
Excerpted from Wikipedia’s “pyrrolnitrin” article, available under the CC BY-SA 4.0 licence.