tilpisertib   Click here for help

GtoPdb Ligand ID: 12094

Synonyms: GS 4875 | GS-4875
Compound class: Synthetic organic
Comment: Tilpisertib (GS-4875) is an inhibitor of the serine/ threonine kinase Cot (a.k.a. MAP3K8/TPL2). It was developed by Gilead Sciences as a potential anti-inflammatory drug to treat auto-inflammatory diseases. The chemical structure is amongst those that are claimed as Cot (a.k.a. MAP3K8/TPL2) modulators in patent WO2020252151A1 [1]. Inhibition of Cot (which is an upstream regulator in the MEK-ERK pathway) is expected to reduce production and signalling of TNFα. Gilead's development pipeline now contains a TPL2 inhibitor, GS-5290, that is in phase 1 for inflammatory bowel disease. GS-5290 may be follow-up lead compound tilpisertib fosmecarbil.
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 6
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 113.45
Molecular weight 592.25
XLogP 6.15
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 N#Cc1cnc2c(c1NCC(C)(C)C)cc(cc2Cl)N[C@@H](c1cccc2c1ccn(c2=O)C)c1nnn(c1)C12CC(C1)C2
Isomeric SMILES CC(C)(C)CNc1c2cc(cc(c2ncc1C#N)Cl)N[C@@H](c1cccc2c1ccn(c2=O)C)c1cn(nn1)C12CC(C1)C2
InChI InChI=1S/C33H33ClN8O/c1-32(2,3)18-37-28-20(15-35)16-36-29-25(28)10-21(11-26(29)34)38-30(27-17-42(40-39-27)33-12-19(13-33)14-33)23-6-5-7-24-22(23)8-9-41(4)31(24)43/h5-11,16-17,19,30,38H,12-14,18H2,1-4H3,(H,36,37)/t19?,30-,33?/m0/s1
InChI Key VFGSKBLZRDRHOI-ZAGPDIDGSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
6-[[(S)-[1-(1-bicyclo[1.1.1]pentanyl)triazol-4-yl]-(2-methyl-1-oxoisoquinolin-5-yl)methyl]amino]-8-chloro-4-(2,2-dimethylpropylamino)quinoline-3-carbonitrile
International Nonproprietary Names Click here for help
INN number INN
11442 tilpisertib
Synonyms Click here for help
GS 4875 | GS-4875
Database Links Click here for help
CAS Registry No. 2065153-41-3 (source: WHO INN record)
ChEMBL Ligand CHEMBL4802154
GtoPdb PubChem SID 472319216
PubChem CID 124181541
Search Google for chemical match using the InChIKey VFGSKBLZRDRHOI-ZAGPDIDGSA-N
Search Google for chemicals with the same backbone VFGSKBLZRDRHOI
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UniChem Compound Search for chemical match using the InChIKey VFGSKBLZRDRHOI-ZAGPDIDGSA-N
UniChem Connectivity Search for chemical match using the InChIKey VFGSKBLZRDRHOI-ZAGPDIDGSA-N