3-chloro-4-(3-chloro-2-nitrophenyl)-1H-pyrrole

• ChemBase ID: 132935
• Molecular Formular: C10H6Cl2N2O2
• Molecular Mass: 257.07284
• Monoisotopic Mass: 255.9806328
• SMILES: c1cc(c(c(c1)Cl)[N+](=O)[O-])c1c[nH]cc1Cl
• Canonical SMILES: Clc1c[nH]cc1c1cccc(c1[N+](=O)[O-])Cl
• 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
• InChIKey: QJBZDBLBQWFTPZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-chloro-4-(3-chloro-2-nitrophenyl)-1H-pyrrole
• IUPAC Traditional name: pyrrolnitrin
• Synonyms: 3-Chloro-4-(3-chloro-2-nitrophenyl)pyrrole; Pyrrolnitrin from Pseudomonas cepacia

Database IDs

• EC Number: 213-812-7
• MDL Number: MFCD00865605
• PubChem SID: 24898985; 162227212
• PubChem CID: 13916

CALCULATED PROPERTIES

• Acid pKa: 15.312431
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.8484287
• LogD (pH = 7.4): 3.8484287
• Log P: 3.8484287
• Molar Refractivity: 62.8873 cm^3
• Polarizability: 24.67312 Å^3
• Polar Surface Area: 61.61 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: solid

Safety Information

• RTECS: UX9450000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Shipped in: wet ice

DETAILS

Sigma Aldrich - P8861

Specificity
The purified antibiotic has strong antifungal activity and is less efficient against bacteria or yeast.
Biochem/physiol Actions
Pyrrolnitrin blocks the terminal electron transport between succinate or reduced NADH and coenzyme Q. In mitochondria preparations of S. cerevisiae, the antibiotic inhibited succinate oxidase, NADH oxidase, succinate cythochrome C reductase, and NADH-cytochrome C reductase. Pyrrolnitrin is involved in many cellular processes such as oxidative stress, electron transport, DNA and RNA synthesis.