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Literature summary for 3.1.6.2 extracted from
- Structure-activity relationship for the first-in-class clinical steroid sulfatase inhibitor irosustat (STX64, BN83495) (2011), ChemMedChem, 6, 2019-2034.
Inhibitors
| Inhibitors | Comment | Organism | Structure |
|---|---|---|---|
| 2-methoxy-6-oxo-6,7,8,9,10,11-hexahydrocyclohepta[c]chromen-3-yl sulfamate | - |
Homo sapiens |  |
| 3-oxo-1,3-dihydro-2H-cyclobuta[c]chromen-6-yl sulfamate | - |
Homo sapiens | |
| 4-oxo-1,2,3,4-tetrahydrocyclopenta[c]chromen-7-yl sulfamate | - |
Homo sapiens | |
| 5-methyl-6-oxo-6,7,8,9,10,11-hexahydro-5H-cyclohepta[c]quinolin-3-yl sulfamate | - |
Homo sapiens | |
| 6-(3-phenylpropoxy)-8,9,10,11-tetrahydro-7H-cyclohepta[c]quinolin-3-yl sulfamate | - |
Homo sapiens | |
| 6-(pentyloxy)-8,9,10,11-tetrahydro-7H-cyclohepta[c]quinolin-3-yl sulfamate | - |
Homo sapiens | |
| 6-methoxy-8,9,10,11-tetrahydro-7H-cyclohepta[c]quinolin-3-yl sulfamate | - |
Homo sapiens | |
| 6-oxo-5-(3-phenylpropyl)-6,7,8,9,10,11-hexahydro-5H-cyclohepta[c]quinolin-3-yl sulfamate | - |
Homo sapiens | |
| 6-oxo-5-pentyl-6,7,8,9,10,11-hexahydro-5H-cyclohepta[c]quinolin-3-yl sulfamate | - |
Homo sapiens | |
| 6-oxo-6,7,8,9,10,11,12,13,14,15,16,17,18,19-tetradecahydrocyclopentadeca[c]chromen-3-yl sulfamate | - |
Homo sapiens | |
| 6-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydrocyclotrideca[c]chromen-3-yl sulfamate | - |
Homo sapiens | |
| 6-oxo-6,7,8,9,10,11,12,13,14,15-decahydrocycloundeca[c]chromen-3-yl sulfamate | - |
Homo sapiens | |
| 6-oxo-6,7,8,9,10,11,12,13-octahydrocyclonona[c]chromen-3-yl sulfamate | - |
Homo sapiens | |
| 6-oxo-6,7,8,9,10,11-hexahydro-5H-cyclohepta[c]quinolin-3-yl sulfamate | - |
Homo sapiens | |
| 6-oxo-6,7,8,9,10,11-hexahydro-5H-cyclohepta[c]quinolin-3-ylsulfamide | - |
Homo sapiens | |
| 6-oxo-6,7,8,9,10,11-hexahydrocyclohepta[c]chromen-2-yl sulfamate | - |
Homo sapiens | |
| 6-oxo-6,7,8,9,10,11-hexahydrocyclohepta[c]chromen-3-yl dimethylsulfamate | - |
Homo sapiens | |
| 6-oxo-6,7,8,9,10,11-hexahydrocyclohepta[c]chromen-3-yl sulfamate | - |
Homo sapiens | |
| 6-oxo-7,8,9,10,11,12,13,14,15,16-decahydro-6H-cyclododeca[c]-chromen-3-yl sulfamate | - |
Homo sapiens | |
| 6-oxo-7,8,9,10,11,12,13,14-octahydro-6H-cyclodeca[c]chromen-3-yl sulfamate | - |
Homo sapiens | |
| 6-oxo-7,8,9,10-tetrahydro-6H-benzo[c]chromen-3-yl sulfamate | - |
Homo sapiens | |
| estrone 3-O-sulfamate | - |
Homo sapiens | |
| irosustat | i.e. STX64, BN83495, structure-activity relationship study. The inhibitor is used in clinical trials for patients with advanced hormone-dependent cancer | Homo sapiens | |
| additional information | evaluation of quinolin-2(1H)-one and quinoline derivatives of irosustat as enzyme inhibitors. N-(piperidino), N,N-(dibenzyl)sulfamate, and N,N-dimethyl derivatives of estrone 3-O-sulfamate are weak reversible or inactive inhibitors of the enzyme in placental microsomes. No inhibition by the N-benzoyl estrone 3-O-sulfamate variant 3-(benzyloxy)-8,9,10,11-tetrahydro-5H-cyclohepta[c]quinolin-6(7H)-one. Molecular modelling | Homo sapiens | |
| N-acetylated estrone 3-O-sulfamate | inhibits the enzyme irreversibly, albeit much less potently than estrone 3-O-sulfamate | Homo sapiens | |
Localization
| Localization | Comment | Organism | GeneOntology No. | Textmining |
|---|---|---|---|---|
| microsome | - |
Homo sapiens | - |
- |
Organism
| Organism | UniProt | Comment | Textmining |
|---|---|---|---|
| Homo sapiens | - |
- |
- |
Source Tissue
| Source Tissue | Comment | Organism | Textmining |
|---|---|---|---|
| JEG-3 cell | choriocarcinoma cells | Homo sapiens | - |
| liver | - |
Homo sapiens | - |
| placenta | - |
Homo sapiens | - |
| skin | - |
Homo sapiens | - |
Substrates and Products (Substrate)
| Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| estrone sulfate + H2O | - |
Homo sapiens | estrone + sulfate | - |
? | |
Synonyms
| Synonyms | Comment | Organism |
|---|---|---|
| steroid sulfatase | - |
Homo sapiens |
| STS | - |
Homo sapiens |
IC50 Value
| IC50 Value | IC50 Value Maximum | Comment | Organism | Inhibitor | Structure |
|---|---|---|---|---|---|
| 0.000000015 | - |
in JEG-3 cells, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | 6-oxo-6,7,8,9,10,11,12,13,14,15-decahydrocycloundeca[c]chromen-3-yl sulfamate | |
| 0.000000022 | - |
in JEG-3 cells, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | 6-oxo-6,7,8,9,10,11,12,13-octahydrocyclonona[c]chromen-3-yl sulfamate | |
| 0.000000025 | - |
in JEG-3 cells, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | 6-oxo-7,8,9,10,11,12,13,14-octahydro-6H-cyclodeca[c]chromen-3-yl sulfamate | |
| 0.0000009 | - |
in JEG-3 cells, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | 6-oxo-7,8,9,10-tetrahydro-6H-benzo[c]chromen-3-yl sulfamate | |
| 0.0000015 | - |
in JEG-3 cells, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | 6-oxo-6,7,8,9,10,11-hexahydrocyclohepta[c]chromen-3-yl sulfamate | |
| 0.000007 | - |
in JEG-3 cells, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | 4-oxo-1,2,3,4-tetrahydrocyclopenta[c]chromen-7-yl sulfamate | |
| 0.000032 | - |
in JEG-3 cells, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | 3-oxo-1,3-dihydro-2H-cyclobuta[c]chromen-6-yl sulfamate | |
| 0.000078 | - |
in JEG-3 cells, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | 2-methoxy-6-oxo-6,7,8,9,10,11-hexahydrocyclohepta[c]chromen-3-yl sulfamate | |
| 0.0001 | - |
in JEG-3 cells, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | 6-oxo-7,8,9,10,11,12,13,14,15,16-decahydro-6H-cyclododeca[c]-chromen-3-yl sulfamate | |
| 0.00022 | - |
in JEG-3 cells, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | 6-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydrocyclotrideca[c]chromen-3-yl sulfamate | |
| 0.00024 | - |
pH not specified in the publication, temperature not specified in the publication | Homo sapiens | 6-oxo-6,7,8,9,10,11-hexahydro-5H-cyclohepta[c]quinolin-3-yl sulfamate | |
| 0.000283 | - |
in JEG-3 cells, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | 6-oxo-6,7,8,9,10,11-hexahydrocyclohepta[c]chromen-2-yl sulfamate | |
| 0.001 | - |
above, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | 6-oxo-6,7,8,9,10,11-hexahydro-5H-cyclohepta[c]quinolin-3-ylsulfamide | |
| 0.0016 | - |
in JEG-3 cells, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | 6-oxo-6,7,8,9,10,11,12,13,14,15,16,17,18,19-tetradecahydrocyclopentadeca[c]chromen-3-yl sulfamate | |
| 0.0024 | - |
pH not specified in the publication, temperature not specified in the publication | Homo sapiens | 5-methyl-6-oxo-6,7,8,9,10,11-hexahydro-5H-cyclohepta[c]quinolin-3-yl sulfamate | |
| 0.01 | - |
above, in JEG-3 cells, pH not specified in the publication, temperature not specified in the publication | Homo sapiens | 6-oxo-6,7,8,9,10,11-hexahydrocyclohepta[c]chromen-3-yl dimethylsulfamate | |
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