X14   Click here for help

GtoPdb Ligand ID: 13170

Compound class: Synthetic organic
Comment: X14 is a small-molecule that interacts with PD-L1 and inhibits its interaction with its receptor PD-1 [1]. It is a structural derivative of BMS-202. Small molecules like these are proposed as an alternative immunotherapy modality to anti-PD-1 or anti-PD-L1 monoclonals.
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 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.

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Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 62.13
Molecular weight 426.87
XLogP 1.6
No. Lipinski's rules broken 0
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.

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Canonical SMILES C1=CC(=C(C=C1)F)C2=C(C(=CC=C2)COC3=CC=C4CN(CCC4=N3)CC(=O)O)Cl
Isomeric SMILES ClC1=C(COC2=NC=3CCN(CC(O)=O)CC3C=C2)C=CC=C1C4=C(F)C=CC=C4
InChI InChI=1S/C23H20ClFN2O3/c24-23-16(4-3-6-18(23)17-5-1-2-7-19(17)25)14-30-21-9-8-15-12-27(13-22(28)29)11-10-20(15)26-21/h1-9H,10-14H2,(H,28,29)
InChI Key YAHBFTAUXKIAHZ-UHFFFAOYSA-N
Selectivity at ligand targets
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
programmed cell death 1 ligand 1 Hs Inhibitor Binding 7.8 pKd - 1
⤷ pKd 7.8 (Kd 1.462x10-8 M) [1]
programmed cell death 1 ligand 1 Mm Inhibitor Binding 6.4 pKd - 1
⤷ pKd 6.4 (Kd 3.92x10-7 M) [1]
programmed cell death 1 ligand 1 Hs Inhibitor Binding 7.8 pIC50 - 1
⤷ pIC50 7.8 (IC50 1.573x10-8 M) [1]
Description: Potency of inhibiting PD-1/PD-L1 interaction.