BAY-747   Click here for help

GtoPdb Ligand ID: 12763

Synonyms: BAY 1165747 [2] | BAY747 | compound 28 [PMID: 37040336]
Compound class: Synthetic organic
Comment: BAY-747 is an orally active and brain-penetrant soluble guanylyl cyclase (sGC) stimulator [2-3]. It was developed to treat resistant hypertension. It has also been suggested as a potential therapy for Duchenne muscular dystrophy, that is proposed to improve skeletal muscle function via activation of the NO-sGC-cGMP pathway [1]
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 6
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 79.95
Molecular weight 416.47
XLogP 2.22
No. Lipinski's rules broken 0
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 CC[C@@](C)(CNC(=O)C1=C(C)N=C2C(=CC(=CN12)C)OCC3=C(C=CC=C3F)F)N
Isomeric SMILES CC[C@@](C)(CNC(=O)C1=C(N=C2N1C=C(C=C2OCC3=C(C=CC=C3F)F)C)C)N
InChI InChI=1S/C22H26F2N4O2/c1-5-22(4,25)12-26-21(29)19-14(3)27-20-18(9-13(2)10-28(19)20)30-11-15-16(23)7-6-8-17(15)24/h6-10H,5,11-12,25H2,1-4H3,(H,26,29)/t22-/m0/s1
InChI Key MITNUFZPBQIMAT-QFIPXVFZSA-N
References
1. Krishnan SM, Nordlohne J, Dietz L, Vakalopoulos A, Haning P, Hartmann E, Seifert R, Hüser J, Mathar I, Sandner P. (2021)
Assessing the Use of the sGC Stimulator BAY-747, as a Potential Treatment for Duchenne Muscular Dystrophy.
Int J Mol Sci, 22 (15). DOI: 10.3390/ijms22158016 [PMID:34360780]
2. Vakalopoulos A, Wunder F, Hartung IV, Redlich G, Jautelat R, Buchgraber P, Hassfeld J, Gromov AV, Lindner N, Bierer D et al.. (2023)
New Generation of sGC Stimulators: Discovery of Imidazo[1,2-a]pyridine Carboxamide BAY 1165747 (BAY-747), a Long-Acting Soluble Guanylate Cyclase Stimulator for the Treatment of Resistant Hypertension.
J Med Chem, 66 (11): 7280-7303. [PMID:37040336]
3. Wunder F, Stasch JP, Knorr A, Mondritzki T, Brockschnieder D, Becker-Pelster EM, Sandner P, Tinel H, Redlich G, Hartung IV et al.. (2023)
Identification and characterization of the new generation soluble guanylate cyclase stimulator BAY-747 designed for the treatment of resistant hypertension.
Br J Pharmacol, 180 (19): 2500-2513. [PMID:37170767]