fluorothiazinon   Click here for help

GtoPdb Ligand ID: 13810

Synonyms: CL-55 | fluorothiazinone | Ftortiazinon
Compound class: Synthetic organic
Comment: Fluorothiazinon is a clinical stage thiohydrazide compound with promising anti-virulence activity against Gram-negative bacteria [3,5,7]. Functionally it is an inhibitor of the type III secretion system (T3SS) [7], one of the main pathogenicity factors of Gram-negative bacteria [2].
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 7
Hydrogen bond donors 2
Rotatable bonds 7
Topological polar surface area 116.53
Molecular weight 421.42
XLogP 1.22
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 CCOC1=CC(=CC=C1O)CN2C(=O)CSC(=N2)C(=O)NC3=CC=C(C=C3F)F
Isomeric SMILES CCOC1=C(C=CC(=C1)CN2C(=O)CSC(=N2)C(=O)NC3=C(C=C(C=C3)F)F)O
InChI InChI=1S/C19H17F2N3O4S/c1-2-28-16-7-11(3-6-15(16)25)9-24-17(26)10-29-19(23-24)18(27)22-14-5-4-12(20)8-13(14)21/h3-8,25H,2,9-10H2,1H3,(H,22,27)
InChI Key DAKWAZGLXWXDBB-UHFFFAOYSA-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/)
References
1. Bondareva NE, Soloveva AV, Sheremet AB, Koroleva EA, Kapotina LN, Morgunova EY, Luyksaar SI, Zayakin ES, Zigangirova NA. (2022)
Preventative treatment with Fluorothiazinon suppressed Acinetobacter baumannii-associated septicemia in mice.
J Antibiot (Tokyo), 75 (3): 155-163. [PMID:35064243]
2. Deng W, Marshall NC, Rowland JL, McCoy JM, Worrall LJ, Santos AS, Strynadka NCJ, Finlay BB. (2017)
Assembly, structure, function and regulation of type III secretion systems.
Nat Rev Microbiol, 15 (6): 323-337. [PMID:28392566]
3. Koroleva EA, Kobets NV, Zayakin ES, Luyksaar SI, Shabalina LA, Zigangirova NA. (2015)
Small molecule inhibitor of type three secretion suppresses acute and chronic Chlamydia trachomatis infection in a novel urogenital Chlamydia model.
Biomed Res Int, 2015: 484853. [PMID:25695086]
4. Koroleva EA, Soloveva AV, Morgunova EY, Kapotina LN, Luyksaar SI, Luyksaar SV, Bondareva NE, Nelubina SA, Lubenec NL, Zigangirova NA et al.. (2023)
Fluorothiazinon inhibits the virulence factors of uropathogenic Escherichia coli involved in the development of urinary tract infection.
J Antibiot (Tokyo), 76 (5): 279-290. [PMID:36922636]
5. Nesterenko LN, Zigangirova NA, Zayakin ES, Luyksaar SI, Kobets NV, Balunets DV, Shabalina LA, Bolshakova TN, Dobrynina OY, Gintsburg AL. (2016)
A small-molecule compound belonging to a class of 2,4-disubstituted 1,3,4-thiadiazine-5-ones suppresses Salmonella infection in vivo.
J Antibiot (Tokyo), 69 (6): 422-7. [PMID:26732253]
6. Zigangirova NA, Lubenec NL, Beloborodov VB, Sheremet AB, Nelyubina SA, Bondareva NE, Zakharov KA, Luyksaar SI, Zolotov SA, Levchenko EU et al.. (2024)
A New "Non-Traditional" Antibacterial Drug Fluorothiazinone-Clinical Research in Patients with Complicated Urinary Tract Infections.
Antibiotics (Basel), 13 (6). [PMID:38927143]
7. Zigangirova NA, Zayakin ES, Kapotina LN, Kost EA, Didenko LV, Davydova DY, Rumyanceva JP, Gintsburg AL. (2012)
Development of Chlamydial Type III Secretion System Inhibitors for Suppression of Acute and Chronic Forms of Chlamydial Infection.
Acta Naturae, 4 (2): 87-97. [PMID:22880162]