miricorilant   Click here for help

GtoPdb Ligand ID: 10059

Synonyms: C-118335 | C118335 | compound 7 [PMID: 23131342] | CORT118335
Compound class: Synthetic organic
Comment: Miricorilant (CORT118335) is a potent, orally active non-steroidal glucocorticoid receptor (GR) antagonist that is being developed by Corcept Therapeutics [2]. Selective GR antagonists are being investigated for their potential to mitigate antipsychotic-induced weight gain, a beneficial activity that was first identified using the dual GR/progesterone receptor antagonist mifepristone [1].
Hunt et al. (2010) specify CORT118335 with the InChIKey GVVUZBSCYAVFTI-IYARVYRRSA-N and as the trans isomer (or the (1r,4r) isomer) [2], which corresponds to the chemical structure submitted to the WHO for the INN miricorilant. Note that PubChem lists this compound in the form without any specified stereochemistry, with PubChem CID 66550324, and that ChEMBL record the cis (or (1s,4s)) isomer as CHEMBL2204043 (InChIKey GVVUZBSCYAVFTI-HDICACEKNA-N).
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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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 2
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 65.72
Molecular weight 428.17
XLogP 6.11
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 O=c1[nH]c(=O)c(c([nH]1)C1CCC(CC1)c1ccccc1)Cc1cccc(c1)C(F)(F)F
Isomeric SMILES O=c1[nH]c(=O)c(c([nH]1)[C@@H]1CC[C@H](CC1)c1ccccc1)Cc1cccc(c1)C(F)(F)F
InChI InChI=1S/C24H23F3N2O2/c25-24(26,27)19-8-4-5-15(13-19)14-20-21(28-23(31)29-22(20)30)18-11-9-17(10-12-18)16-6-2-1-3-7-16/h1-8,13,17-18H,9-12,14H2,(H2,28,29,30,31)/t17-,18-
InChI Key GVVUZBSCYAVFTI-IYARVYRRSA-N
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Isomeric SMILES Download
InChI standard identifier Download
InChI standard key Download

Molecular structure representations generated using Open Babel