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Information on EC 3.1.6.2 - steryl-sulfatase and Organism(s) Homo sapiens

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     3 Hydrolases
         3.1 Acting on ester bonds
             3.1.6 Sulfuric-ester hydrolases
                3.1.6.2 steryl-sulfatase
IUBMB Comments
Also acts on some related steryl sulfates.
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Select one or more organisms in this record:
This record set is specific for:
Homo sapiens
Word Map
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
The taxonomic range for the selected organisms is: Homo sapiens
Synonyms
3-beta-hydroxysteroid sulfate sulfatase, arylsufatase, arylsulfatase C, ASC, cholesterol sulfate sulfohydrolase, CHS-ase, dehydroepiandrosterone sulfatase, dehydroepiandrosterone sulfate sulfatase, DHEAS, E1-STS, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
3-beta-hydroxysteroid sulfate sulfatase
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arylsufatase
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arylsulfatase C
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ASC
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cholesterol sulfate sulfohydrolase
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CHS-ase
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dehydroepiandrosterone sulfatase
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dehydroepiandrosterone sulfate sulfatase
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DHEAS
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phenolic steroid sulfatase
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pregnenolone sulfatase
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steroid 3-sulfatase
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steroid sulfatase
steroid sulfate sulfohydrolase
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steroid sulphatase
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sterol sulfatase
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sterolsulfate sulfohydrolase
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Steryl-sulfate sulfohydrolase
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sulfatase, sterol
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additional information
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arylsulfatase activity, E.C. 3.1.6.1, and various steroid sulfatase activities, E.C. 3.1.6.1, are functions of the same protein
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
hydrolysis of sulfuric ester
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PATHWAY SOURCE
PATHWAYS
SYSTEMATIC NAME
IUBMB Comments
steryl-sulfate sulfohydrolase
Also acts on some related steryl sulfates.
CAS REGISTRY NUMBER
COMMENTARY hide
9025-62-1
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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
16alpha-hydroxydehydroepiandrosterone 3-sulfate + H2O
16alpha-hydroxydehydroepiandrosterone + sulfate
show the reaction diagram
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?
17beta-estradiol sulfate + H2O
17beta-estradiol + sulfate
show the reaction diagram
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-
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?
3beta-hydroxyandrost-5-en-17-one 3-sulfate + H2O
3beta-hydroxyandrost-5-en-17-one + sulfate
show the reaction diagram
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-
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4-methylumbelliferyl sulfate + H2O
4-methylumbelliferol + sulfate
show the reaction diagram
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-
-
-
?
4-methylumbelliferyl sulfate + H2O
4-methylumbelliferone + sulfate
show the reaction diagram
4-methylumbelliferyl-6-O-sulfate + H2O
4-methylumbelliferone + sulfate
show the reaction diagram
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-
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?
7-dehydroepiandrosterone sulfate + H2O
7-dehydroepiandrosterone + sulfate
show the reaction diagram
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?
androstenediol sulfate + H2O
androstenediol + sulfate
show the reaction diagram
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?
androstenediol-3-sulfate + H2O
androstenediol + sulfate
show the reaction diagram
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?
arzoxifene sulfate + H2O
arzoxifene + sulfate
show the reaction diagram
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product of sulfotransferase reaction on arzoxifene used in hormone replacement therapy
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?
cholesterol 3-sulfate + H2O
cholesterol + sulfate
show the reaction diagram
cholesterol sulfate + H2O
cholesterol + sulfate
show the reaction diagram
dehydroandrosterone 3-sulfate + H2O
dehydroandrosterone + sulfate
show the reaction diagram
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?
dehydroepiandrosterone 3-sulfate + H2O
dehydroepiandrosterone + sulfate
show the reaction diagram
dehydroepiandrosterone sulfate + H2O
dehydroepiandrosterone + sulfate
show the reaction diagram
dehydroisoandrosterone 3-sulfate + H2O
dehydroisoandrosterone + sulfate
show the reaction diagram
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?
estrone 3-sulfate + H2O
estrone + sulfate
show the reaction diagram
estrone sulfate
estrone + sulfate
show the reaction diagram
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?
estrone sulfate + H2O
estrone + sulfate
show the reaction diagram
p-nitrophenyl-sulfate + H2O
p-nitrophenol + sulfate
show the reaction diagram
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arylsulfatase activity, EC 3.1.6.1, and various steroid sulfatase activities (EC 3.1.6.1) are functions of the same protein
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?
pregnenolone sulfate + H2O
pregnenolone + sulfate
show the reaction diagram
raloxifene sulfate + H2O
raloxifene + sulfate
show the reaction diagram
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product of sulfotransferase reaction on raloxifene used in hormone replacement therapy, the benzothiophene sulfate is substrate, the 4'-phenolic sulfate is no substrate for enzyme
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?
steroid sulfate + H2O
steroid + sulfate
show the reaction diagram
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?
steroid sulfates + H2O
steroid + sulfate
show the reaction diagram
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also acts on some related steryl sulfates, phenol sulfates, steroid arylsulfates and steroid alkyl sulfates catalyzed at the same site
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?
additional information
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
cholesterol sulfate + H2O
cholesterol + sulfate
show the reaction diagram
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cholesterol sulfate metabolism, steroid sulfohydrolase pathway
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?
dehydroepiandrosterone 3-sulfate + H2O
dehydroepiandrosterone + sulfate
show the reaction diagram
P08842
in adipose tissue, further concersion to bioactive androgens and estrogens
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?
dehydroepiandrosterone sulfate + H2O
dehydroepiandrosterone + sulfate
show the reaction diagram
estrone 3-sulfate + H2O
estrone + sulfate
show the reaction diagram
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hydrolyzes estrone 3-sulfate to its active, unsulfated form
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?
estrone sulfate
estrone + sulfate
show the reaction diagram
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?
estrone sulfate + H2O
estrone + sulfate
show the reaction diagram
steroid sulfate + H2O
steroid + sulfate
show the reaction diagram
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?
steroid sulfates + H2O
steroid + sulfate
show the reaction diagram
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also acts on some related steryl sulfates, phenol sulfates, steroid arylsulfates and steroid alkyl sulfates catalyzed at the same site
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?
additional information
?
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(12aS)-N,N-dihydroxy-12a-methyl-1,3-dioxo-2-propyl-1,2,3,4,4a,4b,5,6,10b,11,12,12a-dodecahydronaphtho[2,1-f]isoquinoline-8-sulfinamide
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(17beta)-17-(2,3,4,5,6-pentafluorobenzyl)-estra-1(10),2,4-triene-3,17-diol
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(17beta)-17-(2-furylmethyl)-estra-1(10),2,4-triene-3,17-diol
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(17beta)-17-(3,5-dibromobenzyl)-estra-1(10),2,4-triene-3,17-diol
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(17beta)-17-(3-benzyloxybenzyl)-estra-1(10),2,4-triene-3,17-diol
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(17beta)-17-(3-bromobenzyl)-estra-1(10),2,4-triene-3,17-diol
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(17beta)-17-(3-iodobenzyl)-estra-1(10),2,4-triene-3,17-diol
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(17beta)-17-(3-tert-butylbenzyl)-estra-1(10),2,4-triene-3,17-diol
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(17beta)-17-(3-trifluoromethylbenzyl)-estra-1(10),2,4-triene-3,17-diol
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(17beta)-17-(4-bromobenzyl)-estra-1(10),2,4-triene-3,17-diol
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(17beta)-17-(4-iodobenzyl)-estra-1(10),2,4-triene-3,17-diol
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(17beta)-17-(4-methyl-2-thienyl)-estra-1(10),2,4-triene-3,17-diol
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(17beta)-17-(4-tert-butylbenzyl)-estra-1(10),2,4-triene-3,17-diol
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(17beta)-17-(4-tert-butylbenzyl)estra-1(10),2,4-triene-3,17-diol
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estradiol phenolic reversible inhibitor as reference, possible additional breast cancer therapy, no inhibition at 0.01 microM, at 0.1 microM 39% inhibition, at 1 microM 62% inhibition
(17beta)-17-(4-trifluoromethylbenzyl)-estra-1(10),2,4-triene-3,17-diol
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(17beta)-17-(cyclohexylmethyl)-estra-1(10),2,4-triene-3,17-diol
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(17beta)-17-(cyclopropylmethyl)-estra-1(10),2,4-triene-3,17-diol
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(17beta)-17-(pyridin-3-ylmethyl)-estra-1(10),2,4-triene-3,17-diol
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(17beta)-17-benzyl-estra-1(10),2,4-triene-3,17-diol
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(17beta)-17-benzylestra-1(10),2,4-triene-3,17-diol
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estradiol phenolic reversible inhibitor as reference, possible additional breast cancer therapy, no inhibition at 0.01 microM, at 0.1 microM 15% inhibition, at 1 microM 48% inhibition
(17beta)-17-[3,5-bis(benzyloxy)benzyl]-estra-1(10),2,4-triene-3,17-diol
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(17beta)-17-[3,5-bis(tert-butyl)benzyl]-estra-1(10),2,4-triene-3,17-diol
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(17beta)-17-[3,5-bis(trifluoromethyl)benzyl]-estra-1(10),2,4-triene-3,17-diol
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(17beta)-17-[3-(dibenzylamino)benzyl]-estra-1(10),2,4-triene-3,17-diol
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(17beta)-17-[4-(benzyloxy)benzyl]-estra-1(10),2,4-triene-3,17-diol
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(17beta)-17-{[2-(2-bromoethyl)cyclopropyl]methyl}estra-1(10),2,4-triene-3,17-diol
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(17beta,17'beta)-17,17'-(2E)-but-2-ene-1,4-diylbisestra-1(10),2,4-triene-3,17-diol
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reversible non-competitive or mixed inhibition, estradiol dimer with C17-C17 bond, possible additional breast cancer therapy, no inhibition at 0.01 microM, at 0.1 microM 42% inhibition, at 1 microM 56% inhibition
(17beta,17'beta)-17,17'-butane-1,4-diylbisestra-1(10),2,4-triene-3,17-diol
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reversible non-competitive or mixed inhibition, estradiol dimer with C17-C17 bond, possible additional breast cancer therapy, no inhibition at 0.01 microM, at 0.1 microM 30% inhibition, at 1 microM 54% inhibition
(2-(1-adamantyl)-4-oxo-4H-chromen-6-yl)(oxo)acetic acid
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(2-(1-adamantyl)-4-oxo-4H-chromen-6-yl)acetic acid
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(p-O-sulfamoyl)-N-tetradecanoyl tyramine
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non-estrogenic STS inhibitor, IC50: 56 nM/l, anti-cancer activity
(R)-1-[(4-cyanophenyl)(3-bromo-4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
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pure R(+)-enantiomer of 1-[(4-Cyanophenyl)(3-bromo-4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
(S)-1-[(4-cyanophenyl)(3-bromo-4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
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pure S(-)-enantiomer of 1-[(4-Cyanophenyl)(3-bromo-4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
1-indanone 4-O-sulfamate
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1-indanone 5-O-sulfamate
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1-indanone 6-O-sulfamate
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1-tetralone 6-O-sulfamate
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1-tetralone 7-O-sulfamate
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1-[(4-cyanophenyl)(3-bromo-4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
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bromo derivative of 1-[(4-cyanophenyl)(3-chloro-4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole does improve aromatase inhibitory activity
1-[(4-cyanophenyl)(3-chloro-4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
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meta-chloro derivative of 1-[(4-cyanophenyl)(4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole does increase aromatase inhibition activity
1-[(4-cyanophenyl)(4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
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increase of aromatase inhibitory activity due to presence of a para-cyanophenyl moiety
1-[bis-(3-bromo-4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
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best dual inhibition
1-[bis-(3-sulfamoyloxy-4-methoxyphenyl)methyl]-1H-[1,2,4]triazole
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methoxy groups reduce inhibition of aromatase compared to 1-[bis-(3-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
1-[bis-(3-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
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sulfamate in meta-position increases aromatase inhibition strength compared to para-position
1-[bis-(4-sulfamoyloxy-3-methoxyphenyl)methyl]-1H-[1,2,4]triazole
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exchange in positions of methoxy and sulfamate group compared to 1-[bis-(3-sulfamoyloxy-4-methoxyphenyl)methyl]-1H-[1,2,4]triazole fails to improve aromatase inhibitory activity
16alpha-hydroxydehydroepiandrosterone
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competitive to dihydroepiandrosterone
17alpha-benzyl-17beta-hydroxyestra-1,3,5-(10)-triene-3-boronic acid
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17alpha-benzyl-3,17beta-dihydroxyestra-1,3,5-(10)-triene
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17beta estradiol
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exposure to 17beta estradiol causes 70% reduction of estrone 3-sulfate sulfatase activity in MCF-7 cells after 6 days, but 9% increase in mammary myoepithelial cells
19,19-difluoro-17-oxo-4,9-cyclo-9,10-secoandrosta-1,3,5(10)-trien-1-yl hydrogen sulfate
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19-fluoro-17-oxo-4,9-cyclo-9,10-secoandrosta-1,3,5(10)-trien-1-yl hydrogen sulfate
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2',4'-dicyano-N,N-dihydroxybiphenyl-4-sulfinamide
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2-(1-adamantyl)-4-oxo-4H-chromen-6-yl sulfamate
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2-(1-adamantyl)-4-oxo-4H-chromene-6-carbaldehyde
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2-(1-adamantyl)-4-oxo-4H-chromene-6-carboxamide
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2-(1-adamantyl)-4-oxo-4H-chromene-6-carboxylic acid
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2-(1-adamantyl)-4-oxo-4H-thiochromen-6-yl sulfamate
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2-(1-adamantyl)-4-oxo-4H-thiochromene-6-carbonitrile
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2-(1-adamantyl)-4-oxo-4H-thiochromene-6-carboxylic acid
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2-(1-adamantyl)-6-(hydroxymethyl)-4H-chromen-4-one
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2-(1-adamantyl)-6-glycoloyl-4H-chromen-4-one
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2-(difluoromethyl)-17-oxoestra-1(10),2,4-trien-3-yl hydrogen sulfate
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2-(fluoromethyl)-17-oxoestra-1(10),2,4-trien-3-yl hydrogen sulfate
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2-bromo-4-[(R)-(4-cyanophenyl)(1H-1,2,4-triazol-1-yl)methyl]-N,N-dihydroxybenzenesulfinamide
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2-formyl-17alpha-benzyl-17beta-hydroxyestra-1,3,5(10)-triene
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time- and concentration-dependent inhibitor, shows more or less pseudo-first order behavior at all concentrations
2-methoxy-6-oxo-6,7,8,9,10,11-hexahydrocyclohepta[c]chromen-3-yl sulfamate
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2-methoxyestrone-3-O-sulfamate
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potent active site-directed inhibitor, no effect on STS mRNA expression in fibroblasts
2-phenylindole sulfamate
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2-phenylindole sulfamates with lipophilic side chains in 1- or 5-position of the indole with IC50-values between 2 nM and 0.001 mM, irreversibly inhibits hydrolysis of estrone sulfate in MDA-MB 231 cells, inhibits gene activation in estrogen receptor-positive MCF-7 breast cancer cells in submicromolar concentrations and reduces cell proliferation with IC50 of 0.001 mM
2-t-butyl-4H-1-benzopyran-4-one-6-boronic acid
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2-tert-butyl-6-hydroxy-4H-chromen-4-one
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2-[3-[[(4-[[(aminooxy)sulfinyl]oxy]phenyl)sulfanyl]methyl]-5-(1H-1,2,4-triazol-1-ylmethyl)phenyl]-2-methylpropanenitrile
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2H1-benzpyran 7-O-disulfamate
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3'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-4'-cyanobiphenyl-4-yl sulfamate
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3'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-5'-(2-cyanopropan-2-yl)biphenyl-4-yl sulfamate
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68.2% inhibition at 0.01 mM
3'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-5'-cyanobiphenyl-4-yl sulfamate
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3'-((1H-1,2,4-triazol-1-yl)methyl)-3-chlorobiphenyl-4-yl sulfamate
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3'-((1H-1,2,4-triazol-1-yl)methyl)-4'-cyanobiphenyl-4-yl sulfamate
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3'-((1H-1,2,4-triazol-1-yl)methyl)biphenyl-4-yl sulfamate
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3'-chloro-5-(1H-1,2,4-triazol-1-ylmethyl)biphenyl-2-carbonitrile
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3,4,8-trimethylcoumarin 7-O-sulfamate
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3,4-dihydro-4-methylcoumarin 7-O-sulfamate
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3,4-dihydrocoumarin 7-O-sulfamate
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3,4-dimethylcoumarin 7-O-sulfate
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12-fold more potent than COUMATE
3-oxo-1,3-dihydro-2H-cyclobuta[c]chromen-6-yl sulfamate
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3-sulfamoyloxy-N-3,3,3-trifluoropropyl-16,17-seco-estra-1,3,4(10)-triene-16,17-imide
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highly potent, long-acting, nonestrogenic steroid sulfatase inhibitor with inhibitory properties to human carbonic anhydrase II, thus enabling transport by erythorcytes, no estrogenic effects observed in uterine weight gain study with ovariectomized Wistar rats, 24 h after last dose of 4 days of oral administration of 10 mg/kg/d, in vivo: single dose of 0.1 mg/kg 48% inhibition of liver steroid sulfatase activity, 0.5 and 1 mg/kg total inhibition, activity measured 24 h after dose administration, recovery of steroid sulfatase acitivity after single oral dose of 10 mg/kg: complete inhibition till day 5, day 17: 50% recovery, day 28: complete recovery
4'-((1H-1,2,4-triazol-1-yl)methyl)-2'-cyanobiphenyl-4-yl sulfamate
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4'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-2'-cyanobiphenyl-4-yl sulfamate
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4-(((4-cyanophenyl)(4H-1,2,4-triazol-4-yl)amino)methyl)-2-methoxyphenyl sulfamate
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4-(trifluoromethyl)coumarin 7-O-sulfamate
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-
4-fluoro-17alpha-benzyl-17beta-hydroxyestra-1,3,5(10)-triene
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linear mixed-type inhibition, compound is capable of binding at sites both within and outside the active site
4-methylcoumarin 6,7-O,O-disulfamate
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4-methylcoumarin 7-O-sulfamate
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COUMATE, also in vivo
4-oxo-1,2,3,4-tetrahydrocyclopenta[c]chromen-7-yl sulfamate
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5'-((1H-1,2,4-triazol-1-yl)methyl)-2'-cyanobiphenyl-4-yl sulfamate
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5'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-2'-cyanobiphenyl-4-yl sulfamate
-
-
5,6,7,8-tetrahydronaphthalene 2-O-(N,N-dimethyl)sulfamate
-
-
5,6,7,8-tetrahydronaphthalene 2-O-(N-methyl)sulfamate
-
-
5,6,7,8-tetrahydronaphthalene 2-O-sulfamate
-
-
5-(((4-cyanophenyl)(4H-1,2,4-triazol-4-yl)amino)methyl)-2-methoxyphenyl sulfamate
-
-
5-((1H-1,2,4-triazol-1-yl)methyl)-3'-chloro-4'-hydroxybiphenyl-2-carbonitrile
-
-
5-((1H-1,2,4-triazol-1-yl)methyl)-4'-hydroxybiphenyl-2-carbonitrile
-
-
5-methyl-6-oxo-6,7,8,9,10,11-hexahydro-5H-cyclohepta[c]quinolin-3-yl sulfamate
-
-
5-pregnen-3beta,21-diol
-
most potent inhibitor of C21 steroids
5-pregnen-3beta,21-diol-20-one
-
most potent inhibitor of C21 steroids
5alpha-androstane-3alpha-17beta-diol
-
most potent inhibitor of C19 steroids
6-(3-phenylpropoxy)-8,9,10,11-tetrahydro-7H-cyclohepta[c]quinolin-3-yl sulfamate
-
-
6-(pentyloxy)-8,9,10,11-tetrahydro-7H-cyclohepta[c]quinolin-3-yl sulfamate
-
-
6-methoxy-8,9,10,11-tetrahydro-7H-cyclohepta[c]quinolin-3-yl sulfamate
-
-
6-methoxycoumarin 7-O-sulfamate
-
-
6-oxo-5-(3-phenylpropyl)-6,7,8,9,10,11-hexahydro-5H-cyclohepta[c]quinolin-3-yl sulfamate
-
-
6-oxo-5-pentyl-6,7,8,9,10,11-hexahydro-5H-cyclohepta[c]quinolin-3-yl sulfamate
-
-
6-oxo-6,7,8,9,10,11,12,13,14,15,16,17,18,19-tetradecahydrocyclopentadeca[c]chromen-3-yl sulfamate
-
-
6-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydrocyclotrideca[c]chromen-3-yl sulfamate
-
-
6-oxo-6,7,8,9,10,11,12,13,14,15-decahydrocycloundeca[c]chromen-3-yl sulfamate
-
-
6-oxo-6,7,8,9,10,11,12,13-octahydrocyclonona[c]chromen-3-yl sulfamate
-
-
6-oxo-6,7,8,9,10,11-hexahydro-5H-cyclohepta[c]quinolin-3-yl sulfamate
-
-
6-oxo-6,7,8,9,10,11-hexahydro-5H-cyclohepta[c]quinolin-3-ylsulfamide
-
-
6-oxo-6,7,8,9,10,11-hexahydrocyclohepta[c]chromen-2-yl sulfamate
-
-
6-oxo-6,7,8,9,10,11-hexahydrocyclohepta[c]chromen-3-yl dimethylsulfamate
-
-
6-oxo-6,7,8,9,10,11-hexahydrocyclohepta[c]chromen-3-yl sulfamate
-
-
6-oxo-7,8,9,10,11,12,13,14,15,16-decahydro-6H-cyclododeca[c]-chromen-3-yl sulfamate
-
-
6-oxo-7,8,9,10,11,12,13,14-octahydro-6H-cyclodeca[c]chromen-3-yl sulfamate
-
-
6-oxo-7,8,9,10,11,12-hexahydro-6H-cycloocta[c]chromen-3-yl sulfamate
-
i.e. STW64, treatment of postmenopausal women with estrogen receptor-positive metastatic breast cancer. Inhibitor almost completely blocks enzyme activty in peripheral blood lymphocytes and tumor tissues, inhibition is associated with significant reductions in serum concentrations of androstenediol and estrogens. Serum androstenedione concentration also decreases by up to 86%
6-oxo-7,8,9,10-tetrahydro-6H-benzo[c]chromen-3-yl sulfamate
-
-
6-oxo-8,9,10,11-tetrahydro-7H-cyclohepta-[c][1]benzopyran-3-O-sulfamate
-
6,6,7-COUMATE, IC50: 5.1 nM in JEG-3 cells, 0.43 nM in MCF-7 cells
6-oxo-8,9,10,11-tetrahydro-7H-cylohepta-[c][1]benzopyran-boronic acid
-
-
667-coumate
-
-
7,8-dihydronaphthalene 2-O-sulfamate
-
-
7-hydroxy-4-methylcoumarin 6-O-sulfamate
-
-
AgNO3
-
5 mM, 65% inhibition
Ammonium molybdate
-
10 mM, 20% residual activity
anastrozole
-
-
breast cyst fluid
-
-
-
calcium chloride
-
5 mM, 36% residual activity
cholesterol
-
1 mM, 57% inhibition
coumarin 7-O-sulfamate
-
-
cysteine
-
10 mM, 15% inhibition
dehydroepiandrosterone
dithiothreitol
-
5 mM, 45% residual activity
estra-1,3,5-(10)-triene-17-one-3-boronic acid
-
competitive
estrone 3-O-sulfamate
-
-
Estrone 3-sulfate
estrone-3-O-(N,N-dimethyl)sulfamate
-
-
estrone-3-O-(N-methyl)sulfamate
-
-
estrone-3-O-methylthiophosphonate
-
-
estrone-3-O-sulfamate
estrone-3-sulfamate
glutathione
-
reduced form, 5 mM, 23.5% residual activity
human pituitary luteinizing hormone
-
human pituitary LH, reduces activity to 85% of baseline at 5 ng/ml, dose-dependent
-
interleukin-1beta
-
marked inhibition of mRNA expression and STS activity
-
irosustat
KH2PO4
-
5 mM, 25% inhibition
KW-2581
-
active site-directed irreversible steroidal inhibitor
letrozole
-
-
methyl 2-(1-adamantyl)-4-oxo-4H-chromene-6-carboxylate
-
-
N,N-dihydroxy-6-oxo-6,7,8,9,10,11-hexahydrocyclohepta[c]chromene-3-sulfinamide
-
-
N,N-dimethoxy-6-oxo-6,7,8,9,10,11-hexahydrocyclohepta[c]chromene-3-sulfinamide
-
-
N-acetylated estrone 3-O-sulfamate
-
inhibits the enzyme irreversibly, albeit much less potently than estrone 3-O-sulfamate
Na2B4O7
-
-
Na2SO3
-
5 mM, 43% inhibition
Na2SO4
-
5 mM, 18% inhibition
p-Nitrophenyl sulfate
-
-
phosphate
-
-
pregnenolone
-
1 mM, 10% inhibition
Steroids
-
overview, e.g. estrone, estradiol, C21 steroids, C19 steroids
STX213
STX64
sulfamic acid 2-bromo-4-(2-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)ethyl)phenyl ester
-
ethylene linker, based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold
sulfamic acid 2-bromo-4-(3-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)propyl)phenyl ester
-
propylene linker, based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold
sulfamic acid 2-bromo-4-[[(4-cyanophenyl)[1,2,4]triazol-4-ylamino]methyl]phenyl ester
-
dual aromatase-sulfatase inhibitor, IC50 value for aromatase 0.82 nM
sulfamic acid 2-chloro-4-(2-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)ethyl)phenyl ester
-
ethylene linker, based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold
sulfamic acid 2-chloro-4-(2-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)ethylsulfanyl)phenyl ester
-
thioether linker based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold
sulfamic acid 2-chloro-4-(3-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)propyl)phenyl ester
-
propylene linker, based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold
sulfamic acid 3-(((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)methylsulfanyl)phenyl ester
-
thioether linker, based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold
sulfamic acid 3-(2-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)-ethylsulfanyl)phenyl ester
-
thioether linker, based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold
sulfamic acid 4-(((4-cyanophenyl)-(1,2,4)triazol-4-ylamino)methylsulfanyl)phenyl ester
-
thioether linker, , based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold, best STS inhibitor of tested dual inhibitor compounds
sulfamic acid 4-((2-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)-ethyl)methylsulfamoyl)phenyl ester
-
N-methylated sulfonamide linker, based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold
sulfamic acid 4-(10-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)decylsulfanyl)phenyl ester
-
thioether linker, based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold
sulfamic acid 4-(2-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)-ethyl)phenyl ester
-
ethylene linker, based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold
sulfamic acid 4-(2-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)-ethylsulfanylmethyl)phenyl ester
-
thioether linker, based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold
sulfamic acid 4-(2-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)ethyl)-2-fluorophenyl ester
-
ethylene linker, based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold
sulfamic acid 4-(3-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)-propyl)-2-fluorophenyl ester
-
propylene linker, based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold
sulfamic acid 4-(3-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)propyl)phenyl ester
-
propylene linker, based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold
sulfamic acid 4-(3-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)propylsulfanyl)phenyl ester
-
thioether linker, based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold
sulfamic acid 4-(5-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)pentylsulfanyl)phenyl ester
-
thioether linker, based on phenol sulfamate pharmacophore (STS inhibition) incorporated into YM511 (aromatase inhibitor) scaffold
sulfamic acid 5-[[(4-cyanophenyl)[1,2,4]triazol-4-ylamino]-methyl]-2-fluorophenyl ester
-
dual aromatase-sulfatase inhibitor, IC50 value for aromatase 0.77 nM
TX-1299
-
non-steroid Theramex compound, strong inhibitor, IC50: 5.3 nM in JEG-3 cells, 0.76 nM in MCF-7 cells
-
TX-1492
-
non-steroid Theramex compound, strong inhibitor, IC50: 22.5 nM in JEG-3 cells, 0.07 nM in MCF-7 cells
-
TX-1506
-
non-steroid Theramex compound, strong inhibitor, IC50: 11.9 nM in JEG-3 cells, 0.06 nM in MCF-7 cells
-
vanadium oxide(V)
-
50 mM, 51% residual activity
Zinc acetate
-
1.25 mM, 53% residual activity
additional information
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
17beta estradiol
-
exposure to 17beta estradiol causes 9% increase of estrone 3-sulfate sulfatase activity in mammary myoepithelial cells after 6 days, but 70% reduction in MCF-7 cells
1alpha,25-dihydroxyvitamin D3
-
upregulation of enzyme activity. In HL-60 cell, stimulation is augmented by retinoid X-receptor agonists, blocked by retinoid X-receptor specific antagonists, and retinoic acid receptor specific agonists and antagonist have no effect. In NB-4 cell, upregulation is unaffected by the specific classical nuclear vitamin D receptor and retinoid X-receptor antagonists, but is blocked by a plasma-membrane associated vitamin D receptor antagonist and increases by plasma-membrane associated vitamin D receptor agonists
ascorbic acid
-
activates
Digitonin
-
activates
estrone
-
slightly activates
glutathione
Insulin
-
human recombinant insulin, 30% activation at 10 ng/ml
-
interleukin 6
-
plus tumor necrosis factor alpha, increases STS activity in mock transfected MCF-7 cells and further increases STS activity in transfected MCF-7 cells, activation occurs independently of STS promoter and enhancer elements, may activate via a post-translational modification of STS or by increasing substrate availability
interleukin-1
-
in cultured MCF-7 cells; inhibition of cell growth
-
L-beta-phenylalanine
-
5 mM, 169% of initial activity
L-cysteine
-
5 mM, 202% of initial activity
lithocholic acid
-
5 mM, 226% of initial activity
p-chloromercuribenzoate
-
activates
Tumor necrosis factor alpha
-
additional information
-
not activated by 2-mercaptoethanol, cysteine or dithiothreitol
-