GT-1   Click here for help

GtoPdb Ligand ID: 13251

Synonyms: LCB10-0200
Compound class: Synthetic organic
Comment: GT-1 (LCB10-0200) is a novel antibacterial compound with activity against Gram-negative bacteria [5]. Its struture, in which a siderophore (dihydroxypyridone) is conjugated to a modified aminothiazoylglycyl cephalosporin, was designed to exploit siderophore-dependent pathways for the uptake of iron across the outer membrane of Gram-negative bacteria [5-6].
2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
Hydrogen bond acceptors 17
Hydrogen bond donors 8
Rotatable bonds 16
Topological polar surface area 380.7
Molecular weight 808.2
XLogP -4.21
No. Lipinski's rules broken 4

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
Click here for help

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/)

✖
Canonical SMILES CC(C)(C(=O)O)O/N=C(/C1=C(Cl)SC(=N1)N)\C(=O)N[C@@H]2C(=O)N3C(=C(C[N+]4=CC(=C(N)N=C4)NCCNC(=O)C5=CC(=O)C(=CN5O)O)CS[C@H]23)C(=O)[O-]
Isomeric SMILES CC(C)(C(=O)O)O/N=C(/C1=C(SC(=N1)N)Cl)\C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C[N+]4=CN=C(C(=C4)NCCNC(=O)C5=CC(=O)C(=CN5O)O)N)C(=O)[O-]
InChI InChI=1S/C29H30ClN11O11S2/c1-29(2,27(49)50)52-38-17(16-20(30)54-28(32)37-16)23(45)36-18-24(46)41-19(26(47)48)11(9-53-25(18)41)6-39-7-12(21(31)35-10-39)33-3-4-34-22(44)13-5-14(42)15(43)8-40(13)51/h5,7-8,10,18,25,31,33,51H,3-4,6,9H2,1-2H3,(H7,32,34,36,37,43,44,45,47,48,49,50)/b38-17-/t18-,25-/m1/s1
InChI Key WUCKZQNKKIJUSF-UVXYUCGCSA-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
A phase 1 study (ACTRN12618001980224) was registered in Australia in 2018 to evaluate the safety, tolerability, and pharmacokinetics of GT-1 in healthy participants but was terminated due to unspecified safety concerns. Further clinical development of GT-1, by LegoChem Biosciences (Republic of Korea) and Geom Therapeutics (USA), may have been discontinued [1].