RIPK2 inhibitor 3   Click here for help

GtoPdb Ligand ID: 10413

Synonyms: compound 3 [PMID: 31265286] | Example 1 [WO2014043446A1] | GSK2983559
PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: This is an orally active RIPK2 inhibitor phosphate ester prodrug [1-2]. It is rapidly cleaved by alkaline phosphatases on contact with intestinal tissue and in whole blood. The prodrug formulation was designed to limit systemic exposure, and to focus activity at the preferred site of action in gut tissue.
A crystal structure of RIPK2 in complex with inhibitor 3 has been submitted to the PDB with ID 6RN8.
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 3
Rotatable bonds 9
Topological polar surface area 207.26
Molecular weight 538.07
XLogP 1.49
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 OP(=O)(OCCOc1cc2ncnc(c2cc1S(=O)(=O)C(C)(C)C)Nc1ccc2c(c1)ncs2)O
Isomeric SMILES OP(=O)(OCCOc1cc2ncnc(c2cc1S(=O)(=O)C(C)(C)C)Nc1ccc2c(c1)ncs2)O
InChI InChI=1S/C21H23N4O7PS2/c1-21(2,3)35(29,30)19-9-14-15(10-17(19)31-6-7-32-33(26,27)28)22-11-23-20(14)25-13-4-5-18-16(8-13)24-12-34-18/h4-5,8-12H,6-7H2,1-3H3,(H,22,23,25)(H2,26,27,28)
InChI Key MJLYDVMFNHZMLV-UHFFFAOYSA-N
References
1. Casillas LN, Haile PA, Marquis RW Jr, Wang G. (2014)
Prodrugs of amino quinazoline kinase inhibitor.
Patent number: WO2014043446A1. Assignee: Glaxosmithkline Llc. Priority date: 13/09/2012. Publication date: 20/03/2014.
2. Haile PA, Casillas LN, Votta BJ, Wang GZ, Charnley AK, Dong X, Bury MJ, Romano JJ, Mehlmann JF, King BW et al.. (2019)
Discovery of a First-in-Class Receptor Interacting Protein 2 (RIP2) Kinase Specific Clinical Candidate, 2-((4-(Benzo[d]thiazol-5-ylamino)-6-(tert-butylsulfonyl)quinazolin-7-yl)oxy)ethyl Dihydrogen Phosphate, for the Treatment of Inflammatory Diseases.
J Med Chem, 62 (14): 6482-6494. [PMID:31265286]