pravibismane   Click here for help

GtoPdb Ligand ID: 13590

Synonyms: BisEDT | MBN-101
Compound class: Synthetic organic
Comment: Pravibismane is a member of a novel class of bismuth antibacterials with broad-spectrum activity against both Gram- positive and Gram-negative bacterial pathogens and strong antibiofilm properties [3-4].
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 0
Hydrogen bond donors 0
Rotatable bonds 5
Topological polar surface area 151.8
Molecular weight 694.52
XLogP 3.68
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 C1CS[Bi](S1)SCCS[Bi]2SCCS2
Isomeric SMILES C1CS[Bi](S1)SCCS[Bi]2SCCS2
InChI InChI=1S/3C2H6S2.2Bi/c3*3-1-2-4;;/h3*3-4H,1-2H2;;/q;;;2*+3/p-6
InChI Key GUTNLKRPYCTIHX-UHFFFAOYSA-H

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/)
References
1. Baker B. (2020)
1289. Pravibismane is a Potent, Broad Spectrum Anti-Infective Small Molecule that Rapidly Disrupts Bacterial Bioenergetics and Halts Bacterial Growth.
Open Forum Infect Dis, 7 (Suppl 1): S659–S660. DOI: 10.1093/ofid/ofaa439.1472
2. Lipsky BA, Kim PJ, Murphy B, McKernan PA, Armstrong DG, Baker BHJ. (2024)
Topical pravibismane as adjunctive therapy for moderate or severe diabetic foot infections: A phase 1b randomized, multicenter, double-blind, placebo-controlled trial.
Int Wound J, 21 (4): e14817. [PMID:38567778]
3. Mahony DE, Lim-Morrison S, Bryden L, Faulkner G, Hoffman PS, Agocs L, Briand GG, Burford N, Maguire H. (1999)
Antimicrobial activities of synthetic bismuth compounds against Clostridium difficile.
Antimicrob Agents Chemother, 43 (3): 582-8. [PMID:10049270]
4. Sandha GS, LeBlanc R, Van Zanten SJ, Sitland TD, Agocs L, Burford N, Best L, Mahoney D, Hoffman P, Leddin DJ. (1998)
Chemical structure of bismuth compounds determines their gastric ulcer healing efficacy and anti-Helicobacter pylori activity.
Dig Dis Sci, 43 (12): 2727-32. [PMID:9881506]