mapracorat   Click here for help

GtoPdb Ligand ID: 9654

Synonyms: BOL-303242-X | ZK-245186 | ZK245186
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Mapracorat is a novel non-steroidal selective glucocorticoid receptor agonist (SEGRA) [3-4]. SEGRAs exert their pharmacological effect by activating only the transrepression pathway, which is in contrast to traditional glucocorticosteroids (GCs) which activate both the transactivation and transrepression pathways.The pharmaceutical industry is trying to develop new GCs that are as effective as traditional GCs, but with fewer limiting adverse effects. Mapracorat and GSK866 are prototype compounds that were designed to address this clinical need.

mapracorat is commercially available from our sponsors

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 3
Hydrogen bond donors 2
Rotatable bonds 7
Topological polar surface area 54.38
Molecular weight 462.19
XLogP 5.9
No. Lipinski's rules broken 1

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 Fc1cc2CCOc2c(c1)C(CC(C(F)(F)F)(CNc1cccc2c1ccc(n2)C)O)(C)C
Isomeric SMILES Fc1cc2CCOc2c(c1)C(C[C@](C(F)(F)F)(CNc1cccc2c1ccc(n2)C)O)(C)C
InChI InChI=1S/C25H26F4N2O2/c1-15-7-8-18-20(5-4-6-21(18)31-15)30-14-24(32,25(27,28)29)13-23(2,3)19-12-17(26)11-16-9-10-33-22(16)19/h4-8,11-12,30,32H,9-10,13-14H2,1-3H3/t24-/m1/s1
InChI Key VJGFOYBQOIPQFY-XMMPIXPASA-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
International Nonproprietary Names Click here for help
INN number INN
9214 mapracorat
Synonyms Click here for help
BOL-303242-X | ZK-245186 | ZK245186
Database Links Click here for help
CAS Registry No. 887375-26-0 (source: WHO INN record)
ChEMBL Ligand CHEMBL2103876
GtoPdb PubChem SID 340590284
PubChem CID 24795088
Search Google for chemical match using the InChIKey VJGFOYBQOIPQFY-XMMPIXPASA-N
Search Google for chemicals with the same backbone VJGFOYBQOIPQFY
Search PubMed clinical trials mapracorat
Search PubMed titles mapracorat
Search PubMed titles/abstracts mapracorat
UniChem Compound Search for chemical match using the InChIKey VJGFOYBQOIPQFY-XMMPIXPASA-N
UniChem Connectivity Search for chemical match using the InChIKey VJGFOYBQOIPQFY-XMMPIXPASA-N

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MedChemExpress
Mapracorat (links to external site)
Cat. No. HY-14864