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nifurtoinol   Click here for help

GtoPdb Ligand ID: 12346

Synonyms: hydroxymethylnitrofurantoin | Urfadyn PL®
Approved drug
nifurtoinol is an approved drug
Compound class: Synthetic organic
Comment: Nifurtoinol is a nitrofuran drug with antibacterial activity. Please note that the structure to which the CAS number is assigned does not specify stereochemistry.
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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 6
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 129.49
Molecular weight 268.04
XLogP 0.33
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES [O-][N+](=O)c1ccc(o1)/C=N/N1CC(=O)N(C1=O)CO
Isomeric SMILES C1C(=O)N(C(=O)N1/N=C/c1ccc(o1)[N+](=O)[O-])CO
InChI InChI=1S/C9H8N4O6/c14-5-11-7(15)4-12(9(11)16)10-3-6-1-2-8(19-6)13(17)18/h1-3,14H,4-5H2/b10-3+
InChI Key UIDWQGRXEVDFCA-XCVCLJGOSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes.
IUPAC Name Click here for help
3-(hydroxymethyl)-1-[(5-nitrofuran-2-yl)methylideneamino]imidazolidine-2,4-dione
International Nonproprietary Names Click here for help
INN number INN
3997 nifurtoinol
Synonyms Click here for help
hydroxymethylnitrofurantoin | Urfadyn PL®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Nifurtoinol
Other databases
CAS Registry No. 1088-92-2 (source: Scifinder)
ChEBI CHEBI:88255
ChEMBL Ligand CHEMBL1697763
DrugBank Ligand DB13730
DrugCentral Ligand 1930
GtoPdb PubChem SID 479821137
PubChem CID 9571062
Search Google for chemical match using the InChIKey UIDWQGRXEVDFCA-XCVCLJGOSA-N
Search Google for chemicals with the same backbone UIDWQGRXEVDFCA
Search PubMed clinical trials nifurtoinol
Search PubMed titles nifurtoinol
Search PubMed titles/abstracts nifurtoinol
UniChem Compound Search for chemical match using the InChIKey UIDWQGRXEVDFCA-XCVCLJGOSA-N
UniChem Connectivity Search for chemical match using the InChIKey UIDWQGRXEVDFCA-XCVCLJGOSA-N