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 (PubChem CID 57524959), 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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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 CDK toolkit. 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
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.

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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
References
1. Grillot AL, Le Tiran A, Shannon D, Krueger E, Liao Y, O'Dowd H, Tang Q, Ronkin S, Wang T, Waal N et al.. (2014)
Second-generation antibacterial benzimidazole ureas: discovery of a preclinical candidate with reduced metabolic liability.
J Med Chem, 57 (21): 8792-816. [PMID:25317480]
2. Locher CP, Jones SM, Hanzelka BL, Perola E, Shoen CM, Cynamon MH, Ngwane AH, Wiid IJ, van Helden PD, Betoudji F et al.. (2015)
A novel inhibitor of gyrase B is a potent drug candidate for treatment of tuberculosis and nontuberculosis mycobacterial infections.
Antimicrob Agents Chemother, 59 (3): 1455-65. [PMID:25534737]
3. O'Dowd H, Shannon DE, Chandupatla KR, Dixit V, Engtrakul JJ, Ye Z, Jones SM, O'Brien CF, Nicolau DP, Tessier PR et al.. (2015)
Discovery and Characterization of a Water-Soluble Prodrug of a Dual Inhibitor of Bacterial DNA Gyrase and Topoisomerase IV.
ACS Med Chem Lett, 6 (7): 822-6. [PMID:26191374]
4. Talley AK, Thurston A, Moore G, Gupta VK, Satterfield M, Manyak E, Stokes S, Dane A, Melnick D. (2021)
First-in-Human Evaluation of the Safety, Tolerability, and Pharmacokinetics of SPR720, a Novel Oral Bacterial DNA Gyrase (GyrB) Inhibitor for Mycobacterial Infections.
Antimicrob Agents Chemother, 65 (11): e0120821. [PMID:34491803]