DARUSENTAN

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Synonyms
Status
Molecule Category UNKNOWN
UNII 33JD57L6RW
EPA CompTox DTXSID1057664

Structure

InChI Key FEJVSJIALLTFRP-LJQANCHMSA-N
Smiles COc1cc(OC)nc(O[C@H](C(=O)O)C(OC)(c2ccccc2)c2ccccc2)n1
InChI
InChI=1S/C22H22N2O6/c1-27-17-14-18(28-2)24-21(23-17)30-19(20(25)26)22(29-3,15-10-6-4-7-11-15)16-12-8-5-9-13-16/h4-14,19H,1-3H3,(H,25,26)/t19-/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C22H22N2O6
Molecular Weight 410.43
AlogP 2.92
Hydrogen Bond Acceptor 7.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 9.0
Polar Surface Area 100.0
Molecular species ACID
Aromatic Rings 3.0
Heavy Atoms 30.0

Bioactivity

Mechanism of Action Action Reference
Endothelin receptor ET-A antagonist ANTAGONIST PubMed
Protein: Endothelin receptor ET-B
Description: Endothelin receptor type B
Organism : Homo sapiens
P24530 ENSG00000136160
Protein: Endothelin receptor ET-A
Description: Endothelin-1 receptor
Organism : Homo sapiens
P25101 ENSG00000151617
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) Short peptide receptor (family A GPCR) Endothelin receptor
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Assay Description Organism Bioactivity Reference
Binding affinity towards Endothelin A receptor None 6.0 nM
Binding affinity towards human cloned endothelin B receptor by [125I]ET1 displacement. None 16.0 nM
Displacement of [125I]-labeled ET-1 from human cloned endothelin A (ETA) receptor None 0.8 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 4.3 %
Displacement of [125I]-ET-1 from human ETA receptor expressed in CHO cell membranes after 2 hrs by scintillation counting Homo sapiens 6.0 nM
Displacement of [125I]-ET-1 from human ETB receptor expressed in CHO cell membranes after 2 hrs by scintillation counting Homo sapiens 371.0 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 13.37 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 14.04 %
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 0.24 % 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 0.17 % 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 0.24 % 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 0.17 %

Related Entries

Cross References

Resources Reference
ChEMBL CHEMBL23261
DrugBank DB04883
FDA SRS 33JD57L6RW
Guide to Pharmacology 3508
PubChem 177236
SureChEMBL SCHEMBL795084
ZINC ZINC000003826221
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