MRGPRX2 antagonist 17   Click here for help

GtoPdb Ligand ID: 12152

Compound class: Synthetic organic
Comment: The chemical structure for this MRGPRX2 antagonist was revealed during the first disclosures session at the 2022 ACS meeting in Chicago. The orphan MRGPRX GPCRs are being investigated as potential drug targets for mast cell-mediated immune diseases [1-4].
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 5
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 94.29
Molecular weight 491.16
XLogP 4.16
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 Fc1ccc(c(c1)F)Oc1ncc(nc1)NC(=O)[C@@H](N1CCC([C@H](C1)c1cc[n+](cc1)[O-])(F)F)C
Isomeric SMILES C[C@@H](C(=O)Nc1ncc(nc1)Oc1c(cc(cc1)F)F)N1CCC([C@H](C1)c1cc[n+](cc1)[O-])(F)F
InChI InChI=1S/C23H21F4N5O3/c1-14(31-9-6-23(26,27)17(13-31)15-4-7-32(34)8-5-15)22(33)30-20-11-29-21(12-28-20)35-19-3-2-16(24)10-18(19)25/h2-5,7-8,10-12,14,17H,6,9,13H2,1H3,(H,28,30,33)/t14-,17+/m0/s1
InChI Key UOCITXUZOXOHLH-WMLDXEAASA-N
References
1. Al Hamwi G, Riedel YK, Clemens S, Namasivayam V, Thimm D, Müller CE. (2022)
MAS-related G protein-coupled receptors X (MRGPRX): Orphan GPCRs with potential as targets for future drugs.
Pharmacol Ther, 238: 108259. [PMID:35934214]
2. Numata T, Harada K, Nakae S. (2022)
Roles of Mast Cells in Cutaneous Diseases.
Front Immunol, 13: 923495. [PMID:35874756]
3. Ogasawara H, Noguchi M. (2021)
Therapeutic Potential of MRGPRX2 Inhibitors on Mast Cells.
Cells, 10 (11). DOI: 10.3390/cells10112906 [PMID:34831128]
4. Trier AM, Kim BS. (2022)
Structural insights into MRGPRX2: A new vision of itch and allergy.
J Allergy Clin Immunol, 149 (4): 1221-1222. [PMID:35090947]