MK-0359   Click here for help

GtoPdb Ligand ID: 9852

Synonyms: L-454,560 [1] | L-454560 | MK0359
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: MK-0359 is a potent and selective, oral PDE4 inhibitor that has a competitive and reversible mode of interaction. MK-0359 is identified as L-454,560 [1] by citation in [2]. MK-0359 inhibits both the apo- (Mg2+ free) and holoenzyme ((Mg2+-bound) states of PDE4 [1].
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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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View interactive charts of activity data across species
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 6
Hydrogen bond donors 0
Rotatable bonds 7
Topological polar surface area 136.85
Molecular weight 587.15
XLogP 6.09
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 Cc1noc(n1)C(=Cc1cccc(c1)c1cc(cc2c1nccc2)C(S(=O)(=O)C)(C)C)c1ccc(cc1)S(=O)(=O)C
Isomeric SMILES Cc1noc(n1)/C(=C/c1cccc(c1)c1cc(cc2c1nccc2)C(S(=O)(=O)C)(C)C)/c1ccc(cc1)S(=O)(=O)C
InChI InChI=1S/C31H29N3O5S2/c1-20-33-30(39-34-20)28(22-11-13-26(14-12-22)40(4,35)36)17-21-8-6-9-23(16-21)27-19-25(31(2,3)41(5,37)38)18-24-10-7-15-32-29(24)27/h6-19H,1-5H3/b28-17+
InChI Key YYGZHVJDHMMABU-OGLMXYFKSA-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
IUPAC Name Click here for help
3-methyl-5-[(E)-1-(4-methylsulfonylphenyl)-2-[3-[6-(2-methylsulfonylpropan-2-yl)quinolin-8-yl]phenyl]ethenyl]-1,2,4-oxadiazole
Synonyms Click here for help
L-454,560 [1] | L-454560 | MK0359
Database Links Click here for help
BindingDB Ligand 0174022
ChEMBL Ligand CHEMBL372575
GtoPdb PubChem SID 363894146
PubChem CID 9853498
Search Google for chemical match using the InChIKey YYGZHVJDHMMABU-OGLMXYFKSA-N
Search Google for chemicals with the same backbone YYGZHVJDHMMABU
UniChem Compound Search for chemical match using the InChIKey YYGZHVJDHMMABU-OGLMXYFKSA-N
UniChem Connectivity Search for chemical match using the InChIKey YYGZHVJDHMMABU-OGLMXYFKSA-N