ROCK inhibitor 3   Click here for help

GtoPdb Ligand ID: 10425

Synonyms: Chiesi Rock inhibitor [2] | example 3 [WO2010032875A2] [3]
Compound class: Synthetic organic
Comment: Inhibitor 3 is a selectve and potent inhibitor of the Rho-associated kinases, ROCK1 and ROCK2. The chemical structure presented here was drawn from Cantoni et al., 2019 [1]. PubChem CID 46182713 presents the compound without specified stereochemistry.
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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 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 5
Hydrogen bond donors 3
Rotatable bonds 4
Topological polar surface area 103.26
Molecular weight 282.15
XLogP 1.35
No. Lipinski's rules broken 0

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 COc1nc(NC2CCC(CC2)N)c(cc1C(=O)N)F
Isomeric SMILES COc1nc(N[C@@H]2CC[C@H](CC2)N)c(cc1C(=O)N)F
InChI InChI=1S/C13H19FN4O2/c1-20-13-9(11(16)19)6-10(14)12(18-13)17-8-4-2-7(15)3-5-8/h6-8H,2-5,15H2,1H3,(H2,16,19)(H,17,18)/t7-,8-
InChI Key IMZIJLMIOSQRGE-ZKCHVHJHSA-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/)
References
1. Cantoni S, Cavalli S, Pastore F, Accetta A, Pala D, Vaccaro F, Cesari N, De Logu F, Nassini R, Villetti G et al.. (2019)
Pharmacological characterization of a highly selective Rho kinase (ROCK) inhibitor and its therapeutic effects in experimental pulmonary hypertension.
Eur J Pharmacol, 850: 126-134. [PMID:30753868]
2. Dayal N, Mikek CG, Hernandez D, Naclerio GA, Yin Chu EF, Carter-Cooper BA, Lapidus RG, Sintim HO. (2019)
Potently inhibiting cancer cell migration with novel 3H-pyrazolo[4,3-f]quinoline boronic acid ROCK inhibitors.
Eur J Med Chem, 180: 449-456. DOI: 10.1016/j.ejmech.2019.06.089 [PMID:31330446]
3. Terasawa T, Shigenaga S, Itoh S, Maeda J, Watanabe H, Kubo S, Ishii N. (2010)
Heterocyclic carboxamide compounds.
Patent number: WO2010032875A2. Assignee: Astellas Pharma Inc.. Priority date: 18/09/2008. Publication date: 25/03/2010.