GtoPdb is requesting financial support from commercial users. Please see our sustainability page for more information.

runcaciguat   Click here for help

GtoPdb Ligand ID: 12359

Synonyms: BAY 1101042 | BAY-1101042 | BAY1101042 | compound 45 [PMID: 33872507]
PDB Ligand
Compound class: Synthetic organic
Comment: Runcaciguat (BAY 1101042) is an oral, selective soluble guanylyl cyclase (sGC) activator [1]. It is suitable for once-daily dosing.

runcaciguat is commercially available from our sponsors

2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 10
Topological polar surface area 66.4
Molecular weight 487.09
XLogP 6.76
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
Click here for help

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/)

✖
Canonical SMILES OC(=O)C[C@H](c1ccc(c(c1)NC(=O)[C@@H]([C@H](C(F)(F)F)C)c1ccc(cc1)Cl)Cl)C1CC1
Isomeric SMILES C[C@H]([C@@H](c1ccc(cc1)Cl)C(=O)Nc1c(ccc(c1)[C@@H](CC(=O)O)C1CC1)Cl)C(F)(F)F
InChI InChI=1S/C23H22Cl2F3NO3/c1-12(23(26,27)28)21(14-4-7-16(24)8-5-14)22(32)29-19-10-15(6-9-18(19)25)17(11-20(30)31)13-2-3-13/h4-10,12-13,17,21H,2-3,11H2,1H3,(H,29,32)(H,30,31)/t12-,17+,21+/m1/s1
InChI Key NCRMKIWHFXSBGZ-CNBXIYLPSA-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/)
Bioactivity Comments
The potency of runcaciguat was determined as the MEC (minimal effective concentration) that promotes cGMP formation (determined as an at least threefold increase in basal luminescence) in a recombinant sGC-overexpressing cell line [1]. In this assay system runcaciguat's MEC was 1.8 nM. In a biochemical assay using purified enzyme its EC50 is 18 nM.
Selectivity at catalytic receptors
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
Guanylyl cyclase, α1β1 Hs Activator Activation - - - 1
⤷ [1]