S4-1   Click here for help

GtoPdb Ligand ID: 12321

Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: S4-1 is reported as a small molecule inhibitor of the PD-1/PD-L1 inhibitory immune checkpoint [1] that is exploited for cancer immunotherapy. It promotes dimerisation and internalisation of PD-L1 which reduces the opportunity of signaling via interaction with PD-1. As predicted, S4-1-induced PD-L1/PD-1 pathway blockade promotes T cell activation and reverses the immune inhibitory tumour microenvironment. In vivo, it has demonstrated anti-tumour effects in lung and colorectal cancer models (following intraperitoneal administration). Such small molecules are envisaged as alternatives to the existing anti-PD-L1 and anti-PD-1 monoclonal antibody therapeutics.
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 7
Hydrogen bond donors 3
Rotatable bonds 8
Topological polar surface area 116.17
Molecular weight 460.16
XLogP 3.07
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 OC[C@@H](C(=O)O)NCc1cc2c(cc1OC)C(=O)N(C2=O)c1cccc(c1C)c1ccccc1
Isomeric SMILES OC[C@@H](C(=O)O)NCc1cc2c(C(=O)N(c3c(C)c(c4ccccc4)ccc3)C2=O)cc1OC
InChI InChI=1S/C26H24N2O6/c1-15-18(16-7-4-3-5-8-16)9-6-10-22(15)28-24(30)19-11-17(13-27-21(14-29)26(32)33)23(34-2)12-20(19)25(28)31/h3-12,21,27,29H,13-14H2,1-2H3,(H,32,33)/t21-/m0/s1
InChI Key CUQPAAUFONWYPW-NRFANRHFSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
((6-Methoxy-2-(2-methyl-[1,1′-biphenyl]-3-yl)-1,3-dioxoisoindolin-5-yl)methyl)serine
Database Links Click here for help
GtoPdb PubChem SID 479821112
PubChem CID 166642489
Search Google for chemical match using the InChIKey CUQPAAUFONWYPW-NRFANRHFSA-N
Search Google for chemicals with the same backbone CUQPAAUFONWYPW
UniChem Compound Search for chemical match using the InChIKey CUQPAAUFONWYPW-NRFANRHFSA-N
UniChem Connectivity Search for chemical match using the InChIKey CUQPAAUFONWYPW-NRFANRHFSA-N