OPB-171775   Click here for help

GtoPdb Ligand ID: 13643

Synonyms: Example 124 [US20190023662] [2] | OPB171775
Compound class: Synthetic organic
Comment: OPB-171775 is a molecular glue [3]. Structurally it is a PDE3A inhibitor derivative. In gastrointestinal stromal tumour cells it promotes formation of a ternary complex with phosphodiesterase 3A (PDE3A) and schlafen family member 12 (SLFN12). PDE3A/SLFN12 complex formation activates the pro-apoptotic ribonuclease activity of SLFN12, which results in a cytotoxic antitumour effect [1]. This molecular mechanism is proposed as an alternative to tyrosine kinase inhibitor (TKI)-based cancer therapies, particularly for TKI-resistant tumours.

OPB-171775 is commercially available from our sponsors

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 5
Hydrogen bond donors 2
Rotatable bonds 4
Topological polar surface area 70.92
Molecular weight 312.31
XLogP 1.55
No. Lipinski's rules broken 0

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 C[C@@H]1CC(=O)NN=C1C2=C(C(=C(C=C2)OCC(C)(C)O)F)F
Isomeric SMILES C[C@@H]1CC(=O)NN=C1C2=C(C(=C(C=C2)OCC(C)(C)O)F)F
InChI InChI=1S/C15H18F2N2O3/c1-8-6-11(20)18-19-14(8)9-4-5-10(13(17)12(9)16)22-7-15(2,3)21/h4-5,8,21H,6-7H2,1-3H3,(H,18,20)/t8-/m1/s1
InChI Key GGUTYKLJESECBW-MRVPVSSYSA-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/)
Download 2D Structure Click here for help
Canonical SMILES Download
Isomeric SMILES Download
InChI standard identifier Download
InChI standard key Download

Molecular structure representations generated using Open Babel