CINACIGUAT

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Synonyms
Status
Molecule Category UNKNOWN
UNII 59K0Y58UAD

Structure

InChI Key WPYWMXNXEZFMAK-UHFFFAOYSA-N
Smiles O=C(O)CCCCN(CCc1ccccc1OCc1ccc(CCc2ccccc2)cc1)Cc1ccc(C(=O)O)cc1
InChI
InChI=1S/C36H39NO5/c38-35(39)12-6-7-24-37(26-30-19-21-33(22-20-30)36(40)41)25-23-32-10-4-5-11-34(32)42-27-31-17-15-29(16-18-31)14-13-28-8-2-1-3-9-28/h1-5,8-11,15-22H,6-7,12-14,23-27H2,(H,38,39)(H,40,41)

Physicochemical Descriptors

Property Name Value
Molecular Formula C36H39NO5
Molecular Weight 565.71
AlogP 7.05
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 17.0
Polar Surface Area 87.07
Molecular species ZWITTERION
Aromatic Rings 4.0
Heavy Atoms 42.0

Bioactivity

Mechanism of Action Action Reference
Soluble guanylate cyclase activator ACTIVATOR PubMed PubMed
Protein: Soluble guanylate cyclase
Description: Guanylate cyclase soluble subunit alpha-2
Organism : Homo sapiens
P33402 ENSG00000152402
Protein: Soluble guanylate cyclase
Description: Guanylate cyclase soluble subunit alpha-1
Organism : Homo sapiens
Q02108 ENSG00000164116
Protein: Soluble guanylate cyclase
Description: Guanylate cyclase soluble subunit beta-1
Organism : Homo sapiens
Q02153 ENSG00000061918
Assay Description Organism Bioactivity Reference
Activation of HUVEC-derived soluble guanylate cyclase expressed in CHOK1 cells assessed as increase in cGMP production after 1 hr by HTRF assay Homo sapiens 1.0 nM
Activation of soluble guanylate cyclase in human GTM3 cells assessed as increase in cGMP production after 30 mins by fluorescence assay Homo sapiens 4.0 nM
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens 0.34 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 7.038 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.23 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.23 %

Cross References

Resources Reference
ChEBI 142433
ChEMBL CHEMBL1236936
DrugBank DB16126
FDA SRS 59K0Y58UAD
Guide to Pharmacology 5168
PDB Z90
PubChem 9808022
SureChEMBL SCHEMBL249267
ZINC ZINC000003934935
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