olitigaltin   Click here for help

GtoPdb Ligand ID: 12148

Synonyms: GB-0139 | GB0139 | TD-139 | TD139
PDB Ligand
Compound class: Synthetic organic
Comment: Olitigaltin (GB0139) is a galectin-3 inhibitor [3] that is designed for inhalation, and is intended as a therapy for fibrotic lung conditions such as idiopathic pulmonary fibrosis (IPF) [1]. In the fibrotic setting, blocking galectin-3's biological function is predicted to combat the enhanced TGF-β receptor-mediated macrophage differentiation and myofibroblast activation that drives pathological fibrotic changes [2-4].

olitigaltin is commercially available from our sponsors

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 12
Hydrogen bond donors 6
Rotatable bonds 8
Topological polar surface area 226.56
Molecular weight 648.18
XLogP 0.37
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 OC[C@H]1O[C@@H](S[C@@H]2O[C@H](CO)[C@@H]([C@@H]([C@H]2O)n2nnc(c2)c2cccc(c2)F)O)[C@@H]([C@H]([C@H]1O)n1nnc(c1)c1cccc(c1)F)O
Isomeric SMILES c1cc(cc(c1)F)c1cn(nn1)[C@H]1[C@H]([C@H](O[C@H]([C@@H]1O)S[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)n1cc(nn1)c1cc(ccc1)F)O)CO)O
InChI InChI=1S/C28H30F2N6O8S/c29-15-5-1-3-13(7-15)17-9-35(33-31-17)21-23(39)19(11-37)43-27(25(21)41)45-28-26(42)22(24(40)20(12-38)44-28)36-10-18(32-34-36)14-4-2-6-16(30)8-14/h1-10,19-28,37-42H,11-12H2/t19-,20-,21+,22+,23+,24+,25-,26-,27+,28+/m1/s1
InChI Key YGIDGBAHDZEYMT-MQFIMZJJSA-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
Olitigaltin (GB0139) has progressed to clinical evaluation to determine its safety and anti-fibrotic efficacy.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT03832946 A Study to Test the Efficacy and Safety of Inhaled GB0139 in Subjects With Idiopathic Pulmonary Fibrosis (IPF) Phase 2 Interventional Galecto Biotech AB