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furaltadone   Click here for help

GtoPdb Ligand ID: 13898

Synonyms: Altafur® | furmethonol
Approved drug
furaltadone is an approved drug
Compound class: Synthetic organic
Comment: Furaltadone is a nitrofuran drug with antimicrobial activity [1]. The approved drug is a racemic mixture of a 3R, 5S isomer and a 3S, 5R isomer, and this is supported by the INN document which also indicates a racemate. The 3R, 5S isomer (shown here, and in the PubChem link below) is more pharmacologically active. The other isomer is represented by levofuraltadone CID 9579050.
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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Click here for structure editor
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 7
Hydrogen bond donors 0
Rotatable bonds 5
Topological polar surface area 106.74
Molecular weight 324.29
XLogP 0.39
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 C1=C(/C=N/N2CC(CN3CCOCC3)OC2=O)OC(=C1)[N+](=O)[O-]
Isomeric SMILES C1COCCN1CC2CN(C(=O)O2)/N=C/C3=CC=C(O3)[N+](=O)[O-]
InChI InChI=1S/C13H16N4O6/c18-13-16(14-7-10-1-2-12(22-10)17(19)20)9-11(23-13)8-15-3-5-21-6-4-15/h1-2,7,11H,3-6,8-9H2/b14-7+
InChI Key YVQVOQKFMFRVGR-VGOFMYFVSA-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
N-hydroxy-5-[(E)-[5-(morpholin-4-ylmethyl)-2-oxo-1,3-oxazolidin-3-yl]iminomethyl]furan-2-amine oxide
International Nonproprietary Names Click here for help
INN number INN
811 furaltadone
Synonyms Click here for help
Altafur® | furmethonol
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Furaltadone
Other databases
CAS Registry No. 139-91-3 (source: Scifinder)
ChEMBL Ligand CHEMBL1189513
DrugBank Ligand DB16567
DrugCentral Ligand 1256
PubChem CID 9553856
Search Google for chemical match using the InChIKey YVQVOQKFMFRVGR-VGOFMYFVSA-N
Search Google for chemicals with the same backbone YVQVOQKFMFRVGR
Search PubMed clinical trials furaltadone
Search PubMed titles furaltadone
Search PubMed titles/abstracts furaltadone
UniChem Compound Search for chemical match using the InChIKey YVQVOQKFMFRVGR-VGOFMYFVSA-N
UniChem Connectivity Search for chemical match using the InChIKey YVQVOQKFMFRVGR-VGOFMYFVSA-N