evixapodlin   Click here for help

GtoPdb Ligand ID: 11684

Synonyms: compound 139 [WO2019160882A1] | GS-4224 | GS4224 | PD-1/PD-L1-IN 7
Compound class: Synthetic organic
Comment: We obtained the chemical structure for evixapodlin from WHO Proposed list 125 of July 2021. The INN record describes it as a programmed cell death ligand 1 (PD-L1) inhibitor. Evixapodlin is one of the chemical structures that is claimed in Gilead Sciences' patent WO2019160882A1 (compound number 139) [1]. It was developed as an alternative to monocloncal antibody PD-L1/PD-1 interaction inhibitors, for potential anticancer and antiviral activities. First disclosures at the ACS meeting in Chicago in 2022 mapped evixapodlin to Gilead's clinical lead GS-4224. GS-4224 is orally bioavailable.
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 10
Hydrogen bond donors 4
Rotatable bonds 13
Topological polar surface area 152.28
Molecular weight 690.22
XLogP 3.77
No. Lipinski's rules broken 1
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 COc1nc(cnc1CNC[C@@H]1CCC(=O)N1)c1cccc(c1Cl)c1cccc(c1Cl)c1cnc(c(n1)OC)CNC[C@@H]1CCC(=O)N1
Isomeric SMILES COc1nc(cnc1CNC[C@@H]1CCC(=O)N1)c1cccc(c1Cl)c1c(c(ccc1)c1cnc(c(n1)OC)CNC[C@@H]1CCC(=O)N1)Cl
InChI InChI=1S/C34H36Cl2N8O4/c1-47-33-27(15-37-13-19-9-11-29(45)41-19)39-17-25(43-33)23-7-3-5-21(31(23)35)22-6-4-8-24(32(22)36)26-18-40-28(34(44-26)48-2)16-38-14-20-10-12-30(46)42-20/h3-8,17-20,37-38H,9-16H2,1-2H3,(H,41,45)(H,42,46)/t19-,20-/m0/s1
InChI Key OIIOPWHTJZYKIL-PMACEKPBSA-N
References
1. Aktoudianakis E, Cho A, Du Z, Graupe M, Lad LT, Machicao Tello PA, Medley JW, Metobo SE, Mukherjee PK, Naduthambi D et al.. (2019)
Pd-1/pd-l1 inhibitors.
Patent number: WO2019160882A1. Assignee: Gilead Sciences, Inc.. Priority date: 13/02/2018. Publication date: 22/08/2019.