Trade Names
Synonyms
Status
Molecule Category UNKNOWN
ATC R03DC01
UNII XZ629S5L50
EPA CompTox DTXSID5023746

Structure

InChI Key YEEZWCHGZNKEEK-UHFFFAOYSA-N
Smiles COc1cc(C(=O)NS(=O)(=O)c2ccccc2C)ccc1Cc1cn(C)c2ccc(NC(=O)OC3CCCC3)cc12
InChI
InChI=1S/C31H33N3O6S/c1-20-8-4-7-11-29(20)41(37,38)33-30(35)22-13-12-21(28(17-22)39-3)16-23-19-34(2)27-15-14-24(18-26(23)27)32-31(36)40-25-9-5-6-10-25/h4,7-8,11-15,17-19,25H,5-6,9-10,16H2,1-3H3,(H,32,36)(H,33,35)

Physicochemical Descriptors

Property Name Value
Molecular Formula C31H33N3O6S
Molecular Weight 575.69
AlogP 5.7
Hydrogen Bond Acceptor 7.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 8.0
Polar Surface Area 115.73
Molecular species ACID
Aromatic Rings 4.0
Heavy Atoms 41.0

Bioactivity

Mechanism of Action Action Reference
Cysteinyl leukotriene receptor 1 antagonist ANTAGONIST DailyMed
Protein: Cysteinyl leukotriene receptor 1

Description: Cysteinyl leukotriene receptor 1

Organism : Homo sapiens

Q9Y271 ENSG00000173198
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 1 Cytochrome P450 family 1A Cytochrome P450 1A2
- - - - 11
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C9
- - - 2500 -
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A4
- - - - 43
Enzyme Isomerase
- 18100 - - -
Enzyme Protease Serine protease Serine protease SC clan Serine protease S33 family
- 2000 - - -
Enzyme
- 18100 - 2500 11
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Lipid-like ligand receptor (family A GPCR) Leukotriene receptor
- 0-44 0 0-2 -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group C Nuclear hormone receptor subfamily 1 group C member 3
2440 - - - -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group I Nuclear hormone receptor subfamily 1 group I member 2
710-30600 - - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC10 family of sodium-bile acid co-transporters
- 6500 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- 9700 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC47 family of multidrug and toxin extrusion transporters
- 1300 - - 52
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 11100-11100 - - -
Transporter Primary active transporter ATP-binding cassette ABCC subfamily
- 12100 - - -
Assay Description Organism Bioactivity Reference
In vitro binding of cysLT1 receptor to guinea pig lung membranes. Cavia porcellus 2.0 nM
Binding affinity towards Cysteinyl leukotriene D4 receptor (cysLT1) was measured by the displacement of [3H]LTD4 radioligand Cavia porcellus 0.3 nM
Compound was evaluated for its ability to displace [3H]LTD4 from Cysteinyl leukotriene D4 receptor in guinea pig lung membranes Cavia porcellus 0.3 nM
Displacement of [3H]LTD4 on guinea pig lung parenchymal membranes Cavia porcellus 0.3 nM
Binding affinity against Cysteinyl leukotriene D4 receptor None 0.3 nM
Antagonism of Cysteinyl leukotriene receptor 1 from guinea pig lung membranes Cavia porcellus 2.0 nM
Inhibitory contractile effect of compound in guinea-pig tracheal strips induced by LTD4 (100 nM) (% inhibition obtained by comparison with control group) Cavia porcellus 58.7 %
50% inhibitory concentration on the LTD4 (100 nM) induced contraction of guinea-pig tracheal strip bioassay Cavia porcellus 1.03 nM
Compound was tested for its ability to block antigen induced airway obstruction in guinea pig at dose 1 mg/kg at 2 hr Cavia porcellus 51.6 %
In vitro effect of compound on leukotriene-D4 LTD4 (100 nM) induced contraction of isolated guinea pig tracheal strip Cavia porcellus 1.03 nM
Compound was evaluated for LTD4 induced guinea pig trachea contraction Cavia porcellus 0.3162 nM
Ability to antagonize LTD4 receptors isolated from guinea pig lung membranes Cavia porcellus 2.0 nM
Binding affinity against leukotriene D4 receptor in [3H]LTD4 binding assay Cavia porcellus 2.0 nM
Concentration required for inhibition of binding of [3H]LTD4 to guinea pig lung membranes Cavia porcellus 0.44 nM
Displacement of [3H]leukotriene D4 (LTD4) from receptor in guinea pig lung membranes Cavia porcellus 2.3 nM
In vitro for antagonistic activity against LTD4 receptor in guinea pig ileum Cavia porcellus 5.0 nM
In vitro inhibition of [3H]LTD4 binding to guinea pig lung membrane Cavia porcellus 44.0 nM
Inhibition constant for displacement of [3H]LTD4 on guinea pig lung parenchymal membranes Cavia porcellus 0.34 nM
Ability to mobilize Ca+2 in LTD4 dependent Ca+2 mobilization assay in differentiated human monocytic U-937 cells Homo sapiens 1.0 nM
In vitro blocking of extracellular calcium mobilization in human U937 cells Homo sapiens 1.0 nM
Compound was evaluated for influx of calcium mobilization in human U937 cells Homo sapiens 1.0 nM
Compound was tested for its ability to inhibit calcium influx in human U937 cells Homo sapiens 1.0 nM
PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Confirmation HTS to Identify Compounds Cytotoxic to SK(-)GAS Group A Streptococcus. (Class of assay: confirmatory) [Related pubchem assays: 1677 (Project Summary), 1662 (Primary HTS)] Streptococcus 936.0 nM
DRUGMATRIX: Cysteinyl leukotriene receptor 1 radioligand binding (ligand: [3H]LTD4) None 1.731 nM DRUGMATRIX: Cysteinyl leukotriene receptor 1 radioligand binding (ligand: [3H]LTD4) None 0.865 nM
DRUGMATRIX: Protein Serine/Threonine Kinase, ERK2 enzyme inhibition (substrate: Myelin Basic Protein) Escherichia coli 538.0 nM
DRUGMATRIX: Protein Serine/Threonine Kinase, p38alpha enzyme inhibition (substrate: Myelin Basic Protein) Escherichia coli 353.0 nM
DRUGMATRIX: Adenosine A3 radioligand binding (ligand: AB-MECA) None 770.0 nM
Inhibition of human MATE1-mediated ASP+ uptake expressed in HEK293 cells at 20 uM after 1.5 mins by fluorescence assay Homo sapiens 52.0 %
Competitive binding affinity to human PXR LBD (111 to 434) by TR-FRET assay Homo sapiens 710.0 nM
Time dependent inhibition of CYP1A2 (unknown origin) at 100 uM by LC/MS system Homo sapiens 11.0 %
Time dependent inhibition of CYP2C19 in human liver microsomes at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP2D6 (unknown origin) at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP3A4 (unknown origin) at 10 uM by LC/MS system Homo sapiens 43.0 %
Time dependent inhibition of CYP2C8 (unknown origin) at 3 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP2C9 (unknown origin) at 10 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP2B6 (unknown origin) at 10 uM by LC/MS system Homo sapiens 10.0 %
Antagonist activity at human CysLT1 Homo sapiens 1.9 nM
Antagonist activity against CysLT1 receptor (unknown origin) expressed in HEK293 cells assessed as inhibition of LTD4-induced calcium mobilization pre-incubated for 10 mins before LTD4 addition by Fluo-4 AM dye based fluorimetric assay Homo sapiens 14.0 nM
Induction of mitochondrial dysfunction in Sprague-Dawley rat liver mitochondria assessed as inhibition of mitochondrial respiration per mg mitochondrial protein measured for 20 mins by A65N-1 oxygen probe based fluorescence assay Rattus norvegicus 66.2 nM
Displacement of [3H]LTD4 from cysteinyl leukotriene receptor 1 in Hartley guinea pig parenchymal membrane after 30 mins by liquid scintillation counting method Cavia porcellus 0.3 nM
Inhibition of cysteinyl leukotriene receptor 1 (unknown origin) expressed in HEK293 cell membranes after 45 mins by scintillation spectrometry Homo sapiens 1.8 nM
Antagonist potency at human CysLT1R expressed in African green monkey COS7 cells assessed as inhibition of LTD4-induced Ca2+ levels after 60 mins by fura-2/AM-fluorescence based spectrofluorimetry Homo sapiens 0.003981 nM
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600) Staphylococcus aureus subsp. aureus 36.84 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli 4.93 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 3.3 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 41.4 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 20.95 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 0.8 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570) Cryptococcus neoformans 1.96 %
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 -3.07 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 -6.559 %
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 -0.2 % 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 -0.2 %

Cross References

Resources Reference
ChEBI 10100
ChEMBL CHEMBL603
DrugBank DB00549
DrugCentral 2855
FDA SRS XZ629S5L50
Human Metabolome Database HMDB0014689
Guide to Pharmacology 3322
KEGG C07206
PDB ZLK
PharmGKB PA451949
PubChem 5717
SureChEMBL SCHEMBL4175
ZINC ZINC000000896717