TP-6076   Click here for help

GtoPdb Ligand ID: 13198

PDB Ligand
Compound class: Synthetic organic
Comment: TP-6076 is a fully synthetic fluorocycline antibacterial. It has broad-spectrum antibacterial activity against both Gram-positive and Gram-negative pathogens, including carbapenem-resistant Acinetobacter baumannii [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 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 10
Hydrogen bond donors 6
Rotatable bonds 6
Topological polar surface area 173.42
Molecular weight 579.57
XLogP 1.92
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 CCN(CC)[C@H]1[C@@H]2C[C@@H]3CC4=C(C(=CC(=C4C(=C3C(=O)[C@@]2(C(=C(C1=O)C(=O)N)O)O)O)O)[C@@H]5CCCN5)C(F)(F)F
Isomeric SMILES CCN(CC)[C@H]1[C@@H]2C[C@@H]3CC4=C(C(=CC(=C4C(=C3C(=O)[C@@]2(C(=C(C1=O)C(=O)N)O)O)O)O)[C@@H]5CCCN5)C(F)(F)F
InChI InChI=1S/C28H32F3N3O7/c1-3-34(4-2)21-14-9-11-8-13-18(16(35)10-12(15-6-5-7-33-15)20(13)28(29,30)31)22(36)17(11)24(38)27(14,41)25(39)19(23(21)37)26(32)40/h10-11,14-15,21,33,35-36,39,41H,3-9H2,1-2H3,(H2,32,40)/t11-,14-,15-,21-,27-/m0/s1
InChI Key SRAXMTXWTUABCM-DOYYSQEVSA-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/)
No information available.
Summary of Clinical Use Click here for help
TP-6076 completed a Phase 1 trial to evaluate safety and pharmacokinetics in healthy participants (NCT03691584). However, development may have ceased following acquisition of Tetraphase Pharmaceuticals by La Jolla Pharmaceutical Company, who are now part of Innoviva. TP-6076 is not included on Innoviva's pipeline webpage.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
TP-6076 inhibits bacterial protein synthesis by binding to the bacterial 30S ribosomal subunit and blocking binding of aminoacyl tRNA to mRNA. The structure of TP-6076, bound to the A. baumannii ribosome and the Acinetobacter drug efflux pump AdeJ has been elucidated [2].
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT03691584 Phase 1, Safety and Bronchopulmonary PK Study in Healthy Volunteers Phase 1 Interventional La Jolla Pharmaceutical Company