GB1211   Click here for help

GtoPdb Ligand ID: 11202

Synonyms: compound 11d [Zetterberg et al., 2022] | Example 44 [WO2016120403A1] | GB-1211
Compound class: Synthetic organic
Comment: GB1211 is an orally active small molecule galectin-3 inhibitor [1,5]. It was developed by Galecto Biotech for the treatment of fibrotic disease and cancer. 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].
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 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.

✖
Hydrogen bond acceptors 7
Hydrogen bond donors 3
Rotatable bonds 5
Topological polar surface area 138.82
Molecular weight 532
XLogP 2.16
No. Lipinski's rules broken 0
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.

✖
Canonical SMILES OCC1OC(Sc2cncc(c2)Br)C(C(C1O)n1nnc(c1)c1cc(F)c(c(c1)F)F)O
Isomeric SMILES OCC1OC(Sc2cncc(c2)Br)C(C(C1O)n1nnc(c1)c1cc(F)c(c(c1)F)F)O
InChI InChI=1S/C19H16BrF3N4O4S/c20-9-3-10(5-24-4-9)32-19-18(30)16(17(29)14(7-28)31-19)27-6-13(25-26-27)8-1-11(21)15(23)12(22)2-8/h1-6,14,16-19,28-30H,7H2
InChI Key FNCLKJPMEFPXOR-UHFFFAOYSA-N
References
1. Brimert T, Johnsson R, Leffler H, Nilsson U, Zetterberg F. (2017)
Alpha-d-galactoside inhibitors of galectins.
Patent number: WO2016120403A1. Assignee: Galecto Biotech AB. Priority date: 30/01/2015. Publication date: 07/12/2017.
2. MacKinnon AC, Farnworth SL, Hodkinson PS, Henderson NC, Atkinson KM, Leffler H, Nilsson UJ, Haslett C, Forbes SJ, Sethi T. (2008)
Regulation of alternative macrophage activation by galectin-3.
J Immunol, 180 (4): 2650-8. [PMID:18250477]
3. Mackinnon AC, Gibbons MA, Farnworth SL, Leffler H, Nilsson UJ, Delaine T, Simpson AJ, Forbes SJ, Hirani N, Gauldie J et al.. (2012)
Regulation of transforming growth factor-β1-driven lung fibrosis by galectin-3.
Am J Respir Crit Care Med, 185 (5): 537-46. [PMID:22095546]
4. Partridge EA, Le Roy C, Di Guglielmo GM, Pawling J, Cheung P, Granovsky M, Nabi IR, Wrana JL, Dennis JW. (2004)
Regulation of cytokine receptors by Golgi N-glycan processing and endocytosis.
Science, 306 (5693): 120-4. [PMID:15459394]
5. Zetterberg FR, MacKinnon A, Brimert T, Gravelle L, Johnsson RE, Khal-Knutson B, Leffler H, Nilsson UJ, Pedersen A, Peterson K et al.. (2022)
Discovery and Optimization of the First Highly Effective and Orally Available Galectin-3 Inhibitors for Treatment of Fibrotic Disease.
Journal of Medicinal Chemistry,. DOI: 10.1021/acs.jmedchem.2c00660