nitrofural   Click here for help

GtoPdb Ligand ID: 12366

Synonyms: Furacin® | Furacine® | nitrofurazone
Approved drug PDB Ligand
nitrofural is an approved drug (FDA (1945))
Compound class: Synthetic organic
Comment: Nitrofural (also known as nitrofurazone) is a nitrofuran drug with antimicrobial activity. The compound has broad-spectrum antibacterial activity and antiprotozoal activity.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 4
Topological polar surface area 123.76
Molecular weight 198.04
XLogP 0.16
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES NC(=O)N/N=C/c1ccc(o1)[N+](=O)[O-]
Isomeric SMILES c1c(oc(c1)[N+](=O)[O-])/C=N/NC(=O)N
InChI InChI=1S/C6H6N4O4/c7-6(11)9-8-3-4-1-2-5(14-4)10(12)13/h1-3H,(H3,7,9,11)/b8-3+
InChI Key IAIWVQXQOWNYOU-FPYGCLRLSA-N
Bioactivity Comments
Nitrofural has broad-spectrum antibacterial activity against both Gram-positive and Gram-negative bacteria in vitro (reviewed in [1]). Highest activity is against Neisseria gonorrhea (MIC of 0.1-10 μg/ml) and Clostridium spp. (MIC of 1.5-3 μg/ml) but the compound is also active against Streptococci, Staphylococcus aureus, Escherichia coli, Shigella spp. and Salmonella spp.
Activity against protozoal species, including Trypanosoma cruzi (Chagas disease) has also been observed [2-3].