IROSUSTAT

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Synonyms
Status
Molecule Category UNKNOWN
UNII 366037O6O7
EPA CompTox DTXSID50183059

Structure

InChI Key DSLPMJSGSBLWRE-UHFFFAOYSA-N
Smiles NS(=O)(=O)Oc1ccc2c3c(c(=O)oc2c1)CCCCC3
InChI
InChI=1S/C14H15NO5S/c15-21(17,18)20-9-6-7-11-10-4-2-1-3-5-12(10)14(16)19-13(11)8-9/h6-8H,1-5H2,(H2,15,17,18)

Physicochemical Descriptors

Property Name Value
Molecular Formula C14H15NO5S
Molecular Weight 309.34
AlogP 1.64
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 2.0
Polar Surface Area 99.6
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 21.0

Bioactivity

Mechanism of Action Action Reference
Steryl-sulfatase inhibitor INHIBITOR PubMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 19 Cytochrome P450 family 19A Cytochrome P450 19A1
- 300-300 - - -
Enzyme Hydrolase
- 2-2600 - - 50-100
Enzyme Lyase
- 17 - 1050 -
Assay Description Organism Bioactivity Reference
Compound was tested for inhibition of human carbonic anhydrase (hCA II) None 17.0 nM
Tested for the inhibitory activity against Estrone Sulfatase None 8.0 nM
Compound was evaluated for its inhibitory activity against estrone sulfatase enzyme None 0.21 uM tube-1
Compound was evaluated for its percent inhibition against the estrone sulfatase enzyme at a concentration of 5 uM None 86.8 %
Inhibition of estrone sulfatase Homo sapiens 210.0 nM
Inhibitory activity against estrone sulfatase at 0.25 uM (initial screening) Homo sapiens 56.0 %
In vitro inhibition of [6,7-3H]E1S binding to steroid sulfatase in JEG-3 human placental carcinoma cells at 3.3 nM Homo sapiens 50.0 %
Inhibition of steroid sulfatase in JEG3 cell membrane Homo sapiens 1.5 nM
Inhibition of steroid sulfatase in Wistar rat assessed as reduction of PMSG-stimulated plasma estradiol level at 10 mg/kg, po after 3 hrs Rattus norvegicus 100.0 %
Inhibition of steroid sulfatase in Wistar rat assessed as reduction of PMSG-stimulated plasma estradiol level at 10 mg/kg, po after 24 hrs Rattus norvegicus 97.0 %
Inhibition of aromatase activity in human JEG3 cells Homo sapiens 300.0 nM
Inhibition of steroid sulfatase activity in human JEG3 cells Homo sapiens 1.5 nM
Inhibition of human cloned CA2 by stopped-flow CO2 hydration method Homo sapiens 21.0 nM
Inhibition of human cloned CA4 by stopped-flow CO2 hydration method Homo sapiens 24.0 nM
Inhibition of human cloned CA5A by stopped-flow CO2 hydration method Homo sapiens 765.0 nM
Inhibition of human cloned CA5B by stopped-flow CO2 hydration method Homo sapiens 720.0 nM
Inhibition of human cloned CA6 by stopped-flow CO2 hydration method Homo sapiens 653.0 nM
Inhibition of human cloned CA7 by stopped-flow CO2 hydration method Homo sapiens 23.0 nM
Inhibition of human cloned CA9 catalytic domain by stopped-flow CO2 hydration method Homo sapiens 34.0 nM
Inhibition of human cloned CA12 catalytic domain by stopped-flow CO2 hydration method Homo sapiens 12.0 nM
Inhibition of human cloned CA14 by stopped-flow CO2 hydration method Homo sapiens 755.0 nM
Inhibition of aromatase in human JEG3 cells by scintillation spectrometry Homo sapiens 300.0 nM
Inhibition of steroid sulfatase in human JEG3 cells by scintillation spectrometry Homo sapiens 1.5 nM
Inhibition of steroid sulfatase in human intact MCF7 cells Homo sapiens 350.0 nM
Irreversible inhibition of steroid sulfatase in human intact MCF7 cells Homo sapiens 350.0 nM
Antiinflammatory activity against mouse RAW264.7 cells assessed as inhibition of LPS-induced PGE2 production administered 1 hr prior to LPS-challenge measured after 24 hrs by EIA Mus musculus 81.04 nM
Inhibition of steroid sulfatase (unknown origin) Homo sapiens 8.0 nM
Inhibition of steroid sulfatase in human MCF7 cells assessed as conversion of [3H]E1S to [3H]E1 and [3H]E2 at 1 uM after 5 hrs by liquid scintillation counting Homo sapiens 100.0 %
Inhibition of steroid sulfatase in human JEG-3 cells assessed as [14C]-Estrone formation using [3H]E1S as substrate Homo sapiens 421.0 nM
Inhibition of placental microsomal estrone sulfatase (unknown origin) using [3H]-estrone sulphate as substrate Homo sapiens 8.0 nM
Inhibition of human placental microsomes steroid sulfatase using [6,7-3H] E1S as substrate after 30 mins Homo sapiens 8.0 nM
Inhibition of 17beta-HSD1 in human T47D cells at 1 uM preincubated for 1 hr followed by addition of [3H]-E1/E1 as substrate measured after 30 mins by HPLC based radio-detection method Homo sapiens 5.0 %
Inhibition of human placental microsomal STS assessed as formation of E1 preincubated for 30 mins followed by addition of E1S as substrate measured after 20 mins by ELISA Homo sapiens 15.1 nM
Inhibition of STS in human T47D cells preincubated for 1 hr followed by addition of [3H]-E1S/E1S as substrate measured after 24 hrs by HPLC based radio-detection method Homo sapiens 1.9 nM
Irreversible inhibition of STS in human T47D cells preincubated for 2 hrs followed by compound washout and addition of [3H]-E1S/E1S as substrate measured after 24 hrs by HPLC based radio-detection method Homo sapiens 2.1 nM
Inhibition of human placental cytosolic 17beta-HSD1 at 1 uM using [3H]-E1/E1 substrate and NADH after 10 mins by HPLC based radio-detection method Homo sapiens 10.0 %
Inhibition of human placental cytosolic 17beta-HSD2 at 1 uM using [3H]-E2/E2 substrate and NAD+ after 20 mins by HPLC based radio-detection method Homo sapiens 10.0 %
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 -3.0 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 105.8 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 99.62 %
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 0.59 % 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 0.1 % 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 0.59 % 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 0.1 %
Inhibition of steroid sulfatase in human JEG3 cells using [3H] E1S as substrate incubated for 20 hrs by scintillation spectrometry analysis Homo sapiens 2.1 nM
Inhibition of steroid sulfatase in human JEG3 cell lysates at 10 uM using [3H] E1S as substrate after 1 hr by scintillation spectrometry analysis relative to control Homo sapiens 99.1 %
Inhibition of steroid sulfatase in human JEG3 cell lysates using [3H] E1S as substrate after 1 hr by scintillation spectrometry analysis Homo sapiens 6.4 nM
Antiproliferative activity against human T47D cells assessed as reduction in cell proliferation measured after 5 days in presence of estradiol sulfate by crystal violet staining based assay Homo sapiens 920.0 nM

Cross References

Resources Reference
ChEMBL CHEMBL286738
DrugBank DB02292
FDA SRS 366037O6O7
PDB 667
PubChem 5287541
SureChEMBL SCHEMBL1275983
ZINC ZINC000001549366
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