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tilpisertib fosmecarbil   Click here for help

GtoPdb Ligand ID: 12081

Synonyms: Example 1 [WO2020252151A1] [1]
Compound class: Synthetic organic
Comment: We obtained the chemical structure for tilpisertib fosmecarbil from the WHO's proposed INN list 127 (21 July 2022). In this document it was described as a serine/ threonine kinase inhibitor and anti-inflammatory agent. 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, for application in auto-inflammatory diseases. Gilead's development pipeline contains a TPL2 inhibitor, GS-5290, that is in phase 1 for inflammatory bowel disease. Tilpisertib fosmecarbil is likely a follow-up to the parent molecule tilpisertib (formerly GS-4875) that was tested in ulcerative colitis trial NCT04130919.
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 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.

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Hydrogen bond acceptors 12
Hydrogen bond donors 3
Rotatable bonds 13
Topological polar surface area 207.53
Molecular weight 746.21
XLogP 4.27
No. Lipinski's rules broken 2

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
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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.

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/)

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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)C(=O)OCOP(=O)(O)O
Isomeric SMILES C12(CC(C1)C2)n1nnc(c1)[C@@H](N(C(=O)OCOP(=O)(O)O)c1cc2c(c(cnc2c(c1)Cl)C#N)NCC(C)(C)C)c1c2ccn(c(=O)c2ccc1)C
InChI InChI=1S/C35H36ClN8O7P/c1-34(2,3)18-39-29-21(15-37)16-38-30-26(29)10-22(11-27(30)36)44(33(46)50-19-51-52(47,48)49)31(28-17-43(41-40-28)35-12-20(13-35)14-35)24-6-5-7-25-23(24)8-9-42(4)32(25)45/h5-11,16-17,20,31H,12-14,18-19H2,1-4H3,(H,38,39)(H2,47,48,49)/t20?,31-,35?/m0/s1
InChI Key FPQIBCPWXJSFOQ-ILNPBIMBSA-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/)
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
phosphonooxymethyl N-[(S)-[1-(1-bicyclo[1.1.1]pentanyl)triazol-4-yl]-(2-methyl-1-oxoisoquinolin-5-yl)methyl]-N-[8-chloro-3-cyano-4-(2,2-dimethylpropylamino)quinolin-6-yl]carbamate
International Nonproprietary Names Click here for help
INN number INN
12278 tilpisertib fosmecarbil
Synonyms Click here for help
Example 1 [WO2020252151A1] [1]
Database Links Click here for help
CAS Registry No. 2567459-64-5 (source: WHO INN record)
GtoPdb PubChem SID 472319203
PubChem CID 155407072
Search Google for chemical match using the InChIKey FPQIBCPWXJSFOQ-ILNPBIMBSA-N
Search Google for chemicals with the same backbone FPQIBCPWXJSFOQ
Search PubMed clinical trials tilpisertib fosmecarbil
Search PubMed titles tilpisertib fosmecarbil
Search PubMed titles/abstracts tilpisertib fosmecarbil
UniChem Compound Search for chemical match using the InChIKey FPQIBCPWXJSFOQ-ILNPBIMBSA-N
UniChem Connectivity Search for chemical match using the InChIKey FPQIBCPWXJSFOQ-ILNPBIMBSA-N