fobrepodacin   Click here for help

GtoPdb Ligand ID: 13062

Synonyms: pVXc-486 | SPR720
Compound class: Synthetic organic
Comment: Fobrepodacin (SPR720) is an orally administered prodrug that is being developed for the treatment of non-tuberculous mycobacterial pulmonary disease (NTM-PD) [3]. The active metabolite, SPR719, is a novel aminobenzimidazole antibacterial compound that is a dual Inhibitor of bacterial DNA gyrase and DNA topoisomerase 4 [1] .
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 12
Hydrogen bond donors 5
Rotatable bonds 9
Topological polar surface area 176.04
Molecular weight 508.44
XLogP -0.84
No. Lipinski's rules broken 2

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)OP(=O)(O)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)OP(=O)(O)O
InChI InChI=1S/C21H26FN6O6P/c1-4-23-20(29)28-19-26-13-8-12(16(22)15(17(13)27-19)14-6-5-7-33-14)11-9-24-18(25-10-11)21(2,3)34-35(30,31)32/h8-10,14H,4-7H2,1-3H3,(H2,30,31,32)(H3,23,26,27,28,29)/t14-/m1/s1
InChI Key COTQDURISRILOR-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
Is prodrug? Yes
Active form SPR719
IUPAC Name Click here for help
2-[5-[2-(ethylcarbamoylamino)-6-fluoro-7-[(2R)-oxolan-2-yl]-3H-benzimidazol-5-yl]pyrimidin-2-yl]propan-2-yl dihydrogen phosphate
International Nonproprietary Names Click here for help
INN number INN
11650 fobrepodacin
Synonyms Click here for help
pVXc-486 | SPR720
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo SPR720 (phosphate prodrug of SPR719)
Other databases
BindingDB Ligand 50112815
CAS Registry No. 1384984-31-9 (source: Scifinder)
ChEMBL Ligand CHEMBL2221212
DrugBank Ligand DB18409
GtoPdb PubChem SID 491299844
PubChem CID 68108988
Search Google for chemical match using the InChIKey COTQDURISRILOR-CQSZACIVSA-N
Search Google for chemicals with the same backbone COTQDURISRILOR
Search PubMed clinical trials fobrepodacin
Search PubMed titles fobrepodacin
Search PubMed titles/abstracts fobrepodacin
UniChem Compound Search for chemical match using the InChIKey COTQDURISRILOR-CQSZACIVSA-N
UniChem Connectivity Search for chemical match using the InChIKey COTQDURISRILOR-CQSZACIVSA-N