SPR719   Click here for help

GtoPdb Ligand ID: 13545

Synonyms: SPR-719 | VXc-486
Compound class: Synthetic organic
Comment: SPR719 is a novel aminobenzimidazole antibacterial compound that is a dual Inhibitor of bacterial DNA gyrase and DNA topoisomerase 4 [1]. An orally administered prodrug, fobrepodacin (SPR720), is being developed for the treatment of non-tuberculous mycobacterial pulmonary disease (NTM-PD).

SPR719 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 9
Hydrogen bond donors 4
Rotatable bonds 7
Topological polar surface area 119.7
Molecular weight 428.46
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 CCNC(=O)NC1=NC2=C([C@H]3CCCO3)C(=C(C=C2N1)C4=CN=C(C(C)(C)O)N=C4)F
Isomeric SMILES CCNC(=O)NC1=NC2=C(N1)C=C(C(=C2[C@H]3CCCO3)F)C4=CN=C(N=C4)C(C)(C)O
InChI InChI=1S/C21H25FN6O3/c1-4-23-20(29)28-19-26-13-8-12(11-9-24-18(25-10-11)21(2,3)30)16(22)15(17(13)27-19)14-6-5-7-31-14/h8-10,14,30H,4-7H2,1-3H3,(H3,23,26,27,28,29)/t14-/m1/s1
InChI Key BKUISYCLLXCBJV-CQSZACIVSA-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
Prodrug fobrepodacin
IUPAC Name Click here for help
3-ethyl-1-{5-fluoro-6-[2-(2-hydroxypropan-2-yl)pyrimidin-5-yl]-4-[(2R)-oxolan-2-yl]-1H-1,3-benzodiazol-2-yl}urea
Synonyms Click here for help
SPR-719 | VXc-486
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo VXc-486 (prodrug pVXc-486)
Other databases
BindingDB Ligand 50393079
CAS Registry No. 1384984-18-2 (source: Scifinder)
ChEMBL Ligand CHEMBL2220900
GtoPdb PubChem SID 500839955
PubChem CID 57524959
Search Google for chemical match using the InChIKey BKUISYCLLXCBJV-CQSZACIVSA-N
Search Google for chemicals with the same backbone BKUISYCLLXCBJV
UniChem Compound Search for chemical match using the InChIKey BKUISYCLLXCBJV-CQSZACIVSA-N
UniChem Connectivity Search for chemical match using the InChIKey BKUISYCLLXCBJV-CQSZACIVSA-N

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MedChemExpress
SPR719 (links to external site)
Cat. No. HY-12930