BTZ-043   Click here for help

GtoPdb Ligand ID: 13034

Synonyms: BTZ-10526043 | MMV676603
Compound class: Synthetic organic
Comment: BTZ-043 is the lead from a novel class of benzothiazinone compounds with antimycobacterial activity [1], that is is under clinical evaluated as a treatment for tuberculosis (TB). It is an inhibitor of decaprenylphosphoryl-beta-D-ribose oxidase (DprE1), an essential mycobacterial cell wall biosynthesis enzyme [1-3].
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 5
Hydrogen bond donors 0
Rotatable bonds 3
Topological polar surface area 119.57
Molecular weight 431.39
XLogP 2.94
No. Lipinski's rules broken 0
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 C[C@H]1COC2(CCN(CC2)C3=NC(=O)C4=CC(=CC(=C4S3)[N+](=O)[O-])C(F)(F)F)O1
Isomeric SMILES C[C@H]1COC2(O1)CCN(CC2)C3=NC(=O)C4=C(S3)C(=CC(=C4)C(F)(F)F)[N+](=O)[O-]
InChI InChI=1S/C17H16F3N3O5S/c1-9-8-27-16(28-9)2-4-22(5-3-16)15-21-14(24)11-6-10(17(18,19)20)7-12(23(25)26)13(11)29-15/h6-7,9H,2-5,8H2,1H3/t9-/m0/s1
InChI Key GTUIRORNXIOHQR-VIFPVBQESA-N
References
1. Makarov V, Manina G, Mikusova K, Möllmann U, Ryabova O, Saint-Joanis B, Dhar N, Pasca MR, Buroni S, Lucarelli AP et al.. (2009)
Benzothiazinones kill Mycobacterium tuberculosis by blocking arabinan synthesis.
Science, 324 (5928): 801-4. [PMID:19299584]
2. Neres J, Pojer F, Molteni E, Chiarelli LR, Dhar N, Boy-Röttger S, Buroni S, Fullam E, Degiacomi G, Lucarelli AP et al.. (2012)
Structural basis for benzothiazinone-mediated killing of Mycobacterium tuberculosis.
Sci Transl Med, 4 (150): 150ra121. [PMID:22956199]
3. Trefzer C, Škovierová H, Buroni S, Bobovská A, Nenci S, Molteni E, Pojer F, Pasca MR, Makarov V, Cole ST et al.. (2012)
Benzothiazinones are suicide inhibitors of mycobacterial decaprenylphosphoryl-β-D-ribofuranose 2'-oxidase DprE1.
J Am Chem Soc, 134 (2): 912-5. [PMID:22188377]