funobactam   Click here for help

GtoPdb Ligand ID: 13114

Synonyms: XNW4107
Compound class: Synthetic organic
Comment: Funobactam (XNW4107) is a novel serine β-lactamase inhibitor, belonging to the diazabicyclooctane (DBO) class [1]. It enhances the activity of carbapenem antibacterials against carbapenem-resistant strains of Acinetobacter baumannii and Klebsiella pneumoniae [1]. Funobactam is in clinical development in combination with imipenem + cilastatin for the treatment of complicated urinary tract infections (cUTIs) and hospital acquired/ventilator-associated bacterial pneumonia (HABP/VABP).

funobactam is commercially available from our sponsors

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 11
Hydrogen bond donors 3
Rotatable bonds 4
Topological polar surface area 179.89
Molecular weight 399.38
XLogP -1.9
No. Lipinski's rules broken 1

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 C1CC12C[C@@H](C3=NN=C([C@@H]4CNC(=N4)N)O3)N5C[C@@H]2N(C5=O)OS(=O)(=O)O
Isomeric SMILES C1CC12C[C@H](N3C[C@@H]2N(C3=O)OS(=O)(=O)O)C4=NN=C(O4)[C@@H]5CNC(=N5)N
InChI InChI=1S/C13H17N7O6S/c14-11-15-4-6(16-11)9-17-18-10(25-9)7-3-13(1-2-13)8-5-19(7)12(21)20(8)26-27(22,23)24/h6-8H,1-5H2,(H3,14,15,16)(H,22,23,24)/t6-,7-,8-/m0/s1
InChI Key GRRBXZJDEZJMHA-FXQIFTODSA-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
IUPAC Name Click here for help
[(2S,5R)-2-[5-[(4S)-2-amino-4,5-dihydro-1H-imidazol-4-yl]-1,3,4-oxadiazol-2-yl]-7-oxospiro[1,6-diazabicyclo[3.2.1]octane-4,1'-cyclopropane]-6-yl] hydrogen sulfate
International Nonproprietary Names Click here for help
INN number INN
12132 funobactam
Synonyms Click here for help
XNW4107
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Imipenem/funobactam
Other databases
CAS Registry No. 2365454-12-0 (source: Scifinder)
ChEMBL Ligand CHEMBL5095101
GtoPdb PubChem SID 491299896
PubChem CID 158340749
Search Google for chemical match using the InChIKey GRRBXZJDEZJMHA-FXQIFTODSA-N
Search Google for chemicals with the same backbone GRRBXZJDEZJMHA
Search PubMed clinical trials funobactam
Search PubMed titles funobactam
Search PubMed titles/abstracts funobactam
UniChem Compound Search for chemical match using the InChIKey GRRBXZJDEZJMHA-FXQIFTODSA-N
UniChem Connectivity Search for chemical match using the InChIKey GRRBXZJDEZJMHA-FXQIFTODSA-N

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MedChemExpress
Funobactam (links to external site)
Cat. No. HY-147274