compound 3 [PMID: 28603634]   Click here for help

GtoPdb Ligand ID: 9628

Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: EP4 antagonists from Eli Lilly are being investigated as analgesic and anti‐inflammatory molecules [2]. This one is example 22 in patent US20160251306 [1], which has 43 analogues but reports only 2 IC50s.
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 3
Rotatable bonds 6
Topological polar surface area 99.52
Molecular weight 390.16
XLogP 3.34
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 OCc1cccc(c1)c1ccc(c(n1)C(=O)Nc1c(C)ccc(c1C)C(=O)O)C
Isomeric SMILES OCc1cccc(c1)c1ccc(c(n1)C(=O)Nc1c(C)ccc(c1C)C(=O)O)C
InChI InChI=1S/C23H22N2O4/c1-13-7-9-18(23(28)29)15(3)20(13)25-22(27)21-14(2)8-10-19(24-21)17-6-4-5-16(11-17)12-26/h4-11,26H,12H2,1-3H3,(H,25,27)(H,28,29)
InChI Key WRBLOVAXQYYLFM-UHFFFAOYSA-N
References
1. Blanco-Pillado et al.. (2016)
Dimethylbenzoic acid compounds.
Patent number: US20160251306. Assignee: Eli Lilly. Priority date: 05/08/2017. Publication date: 17/12/2013.
2. Chandrasekhar S, Yu XP, Harvey AK, Oskins JL, Lin C, Wang X, Blanco MJ, Fisher MJ, Kuklish SL, Schiffler MA et al.. (2017)
Analgesic and anti-inflammatory properties of novel, selective, and potent EP4 receptor antagonists.
Pharmacol Res Perspect, 5 (3): e00316. [PMID:28603634]