Information on EC 3.1.6.2 - steryl-sulfatase and Organism(s) Homo sapiens and UniProt Accession P08842

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UNIPROT: P08842
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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria


The taxonomic range for the selected organisms is: Homo sapiens

EC NUMBER
COMMENTARY hide
3.1.6.2
-
RECOMMENDED NAME
GeneOntology No.
steryl-sulfatase
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
hydrolysis of sulfuric ester
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Steroid hormone biosynthesis
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-
SYSTEMATIC NAME
IUBMB Comments
steryl-sulfate sulfohydrolase
Also acts on some related steryl sulfates.
CAS REGISTRY NUMBER
COMMENTARY hide
9025-62-1
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
metabolism
physiological function
additional information
-
active site residues are D35, D36, FGS75, R79, K134, H136, H290, D342, Q343, and K368
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
estrone sulfate
estrone + sulfate
show the reaction diagram
-
-
-
-
?
16alpha-hydroxydehydroepiandrosterone 3-sulfate + H2O
16alpha-hydroxydehydroepiandrosterone + sulfate
show the reaction diagram
-
-
-
-
?
17beta-estradiol sulfate + H2O
17beta-estradiol + sulfate
show the reaction diagram
-
-
-
-
?
3beta-hydroxyandrost-5-en-17-one 3-sulfate + H2O
3beta-hydroxyandrost-5-en-17-one + sulfate
show the reaction diagram
-
-
-
-
-
4-methylumbelliferyl sulfate + H2O
4-methylumbelliferol + sulfate
show the reaction diagram
-
-
-
-
?
4-methylumbelliferyl sulfate + H2O
4-methylumbelliferone + sulfate
show the reaction diagram
4-methylumbelliferyl-6-O-sulfate + H2O
4-methylumbelliferone + sulfate
show the reaction diagram
-
-
-
-
?
7-dehydroepiandrosterone sulfate + H2O
7-dehydroepiandrosterone + sulfate
show the reaction diagram
-
-
-
-
?
androstenediol sulfate + H2O
androstenediol + sulfate
show the reaction diagram
-
-
-
-
?
androstenediol-3-sulfate + H2O
androstenediol + sulfate
show the reaction diagram
-
-
-
-
?
arzoxifene sulfate + H2O
arzoxifene + sulfate
show the reaction diagram
-
product of sulfotransferase reaction on arzoxifene used in hormone replacement therapy
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
estrone 3-sulfate + H2O
estrone + sulfate
show the reaction diagram
estrone sulfate + H2O
estrone + sulfate
show the reaction diagram
p-nitrophenyl-sulfate + H2O
p-nitrophenol + sulfate
show the reaction diagram
-
arylsulfatase activity, EC 3.1.6.1, and various steroid sulfatase activities (EC 3.1.6.1) are functions of the same protein
-
-
?
pregnenolone sulfate + H2O
pregnenolone + sulfate
show the reaction diagram
raloxifene sulfate + H2O
raloxifene + sulfate
show the reaction diagram
-
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
-
-
?
steroid sulfate + H2O
steroid + sulfate
show the reaction diagram
-
-
-
-
?
steroid sulfates + H2O
steroid + sulfate
show the reaction diagram
-
also acts on some related steryl sulfates, phenol sulfates, steroid arylsulfates and steroid alkyl sulfates catalyzed at the same site
-
-
?
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
estrone sulfate
estrone + sulfate
show the reaction diagram
-
-
-
-
?
cholesterol sulfate + H2O
cholesterol + sulfate
show the reaction diagram
-
cholesterol sulfate metabolism, steroid sulfohydrolase pathway
-
-
?
dehydroepiandrosterone 3-sulfate + H2O
dehydroepiandrosterone + sulfate
show the reaction diagram
P08842
in adipose tissue, further concersion to bioactive androgens and estrogens
-
-
?
dehydroepiandrosterone sulfate + H2O
dehydroepiandrosterone + sulfate
show the reaction diagram
estrone 3-sulfate + H2O
estrone + sulfate
show the reaction diagram
-
hydrolyzes estrone 3-sulfate to its active, unsulfated form
-
-
?
estrone sulfate + H2O
estrone + sulfate
show the reaction diagram
steroid sulfate + H2O
steroid + sulfate
show the reaction diagram
-
-
-
-
?
steroid sulfates + H2O
steroid + sulfate
show the reaction diagram
-
also acts on some related steryl sulfates, phenol sulfates, steroid arylsulfates and steroid alkyl sulfates catalyzed at the same site
-
-
?
additional information
?
-
INHIBITORS
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
-
-
(17beta)-17-(2,3,4,5,6-pentafluorobenzyl)-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-(2-furylmethyl)-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-(3,5-dibromobenzyl)-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-(3-benzyloxybenzyl)-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-(3-bromobenzyl)-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-(3-iodobenzyl)-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-(3-tert-butylbenzyl)-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-(3-trifluoromethylbenzyl)-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-(4-bromobenzyl)-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-(4-iodobenzyl)-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-(4-methyl-2-thienyl)-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-(4-tert-butylbenzyl)-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-(4-tert-butylbenzyl)estra-1(10),2,4-triene-3,17-diol
-
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
-
-
(17beta)-17-(cyclohexylmethyl)-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-(cyclopropylmethyl)-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-(pyridin-3-ylmethyl)-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-benzyl-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-benzylestra-1(10),2,4-triene-3,17-diol
-
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
-
-
(17beta)-17-[3,5-bis(tert-butyl)benzyl]-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-[3,5-bis(trifluoromethyl)benzyl]-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-[3-(dibenzylamino)benzyl]-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-[4-(benzyloxy)benzyl]-estra-1(10),2,4-triene-3,17-diol
-
-
(17beta)-17-{[2-(2-bromoethyl)cyclopropyl]methyl}estra-1(10),2,4-triene-3,17-diol
-
-
(17beta,17'beta)-17,17'-(2E)-but-2-ene-1,4-diylbisestra-1(10),2,4-triene-3,17-diol
-
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
-
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
-
-
(2-(1-adamantyl)-4-oxo-4H-chromen-6-yl)acetic acid
-
-
(p-O-sulfamoyl)-N-tetradecanoyl tyramine
-
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
-
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
-
pure S(-)-enantiomer of 1-[(4-Cyanophenyl)(3-bromo-4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
1-indanone 4-O-sulfamate
-
-
1-indanone 5-O-sulfamate
-
-
1-indanone 6-O-sulfamate
-
-
1-tetralone 6-O-sulfamate
-
-
1-tetralone 7-O-sulfamate
-
-
1-[(4-cyanophenyl)(3-bromo-4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
-
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
-
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
-
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
-
best dual inhibition
1-[bis-(3-sulfamoyloxy-4-methoxyphenyl)methyl]-1H-[1,2,4]triazole
-
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
-
sulfamate in meta-position increases aromatase inhibition strength compared to para-position
1-[bis-(4-sulfamoyloxy-3-methoxyphenyl)methyl]-1H-[1,2,4]triazole
-
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
-
competitive to dihydroepiandrosterone
17alpha-benzyl-17beta-hydroxyestra-1,3,5-(10)-triene-3-boronic acid
-
-
17alpha-benzyl-3,17beta-dihydroxyestra-1,3,5-(10)-triene
-
-
17beta estradiol
-
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
-
-
19-fluoro-17-oxo-4,9-cyclo-9,10-secoandrosta-1,3,5(10)-trien-1-yl hydrogen sulfate
-
-
2',4'-dicyano-N,N-dihydroxybiphenyl-4-sulfinamide
-
-
2-(1-adamantyl)-4-oxo-4H-chromen-6-yl sulfamate
-
-
2-(1-adamantyl)-4-oxo-4H-chromene-6-carbaldehyde
-
-
2-(1-adamantyl)-4-oxo-4H-chromene-6-carboxamide
-
-
2-(1-adamantyl)-4-oxo-4H-chromene-6-carboxylic acid
-
-
2-(1-adamantyl)-4-oxo-4H-thiochromen-6-yl sulfamate
-
-
2-(1-adamantyl)-4-oxo-4H-thiochromene-6-carbonitrile
-
-
2-(1-adamantyl)-4-oxo-4H-thiochromene-6-carboxylic acid
-
-
2-(1-adamantyl)-6-(hydroxymethyl)-4H-chromen-4-one
-
-
2-(1-adamantyl)-6-glycoloyl-4H-chromen-4-one
-
-
2-(difluoromethyl)-17-oxoestra-1(10),2,4-trien-3-yl hydrogen sulfate
-
-
2-(fluoromethyl)-17-oxoestra-1(10),2,4-trien-3-yl hydrogen sulfate
-
-
2-bromo-4-[(R)-(4-cyanophenyl)(1H-1,2,4-triazol-1-yl)methyl]-N,N-dihydroxybenzenesulfinamide
-
-
2-formyl-17alpha-benzyl-17beta-hydroxyestra-1,3,5(10)-triene
-
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
-
-
2-methoxyestrone-3-O-sulfamate
-
potent active site-directed inhibitor, no effect on STS mRNA expression in fibroblasts
2-phenylindole sulfamate
-
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
-
-
2-tert-butyl-6-hydroxy-4H-chromen-4-one
-
-
2-[3-[[(4-[[(aminooxy)sulfinyl]oxy]phenyl)sulfanyl]methyl]-5-(1H-1,2,4-triazol-1-ylmethyl)phenyl]-2-methylpropanenitrile
-
-
2H1-benzpyran 7-O-disulfamate
-
-
3'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-4'-cyanobiphenyl-4-yl sulfamate
-
-
3'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-5'-(2-cyanopropan-2-yl)biphenyl-4-yl sulfamate
-
68.2% inhibition at 0.01 mM
3'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-5'-cyanobiphenyl-4-yl sulfamate
-
-
3'-((1H-1,2,4-triazol-1-yl)methyl)-3-chlorobiphenyl-4-yl sulfamate
-
-
3'-((1H-1,2,4-triazol-1-yl)methyl)-4'-cyanobiphenyl-4-yl sulfamate
-
-
3'-((1H-1,2,4-triazol-1-yl)methyl)biphenyl-4-yl sulfamate
-
-
3'-chloro-5-(1H-1,2,4-triazol-1-ylmethyl)biphenyl-2-carbonitrile
-
-
3,4,8-trimethylcoumarin 7-O-sulfamate
-
-
-
3,4-dihydro-4-methylcoumarin 7-O-sulfamate
-
-
3,4-dihydrocoumarin 7-O-sulfamate
-
-
3,4-dimethylcoumarin 7-O-sulfate
-
12-fold more potent than COUMATE
3-oxo-1,3-dihydro-2H-cyclobuta[c]chromen-6-yl sulfamate
-
-
3-sulfamoyloxy-N-3,3,3-trifluoropropyl-16,17-seco-estra-1,3,4(10)-triene-16,17-imide
-
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
-
-
4'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-2'-cyanobiphenyl-4-yl sulfamate
-
-
4-(((4-cyanophenyl)(4H-1,2,4-triazol-4-yl)amino)methyl)-2-methoxyphenyl sulfamate
-
-
4-(trifluoromethyl)coumarin 7-O-sulfamate
-
-
4-fluoro-17alpha-benzyl-17beta-hydroxyestra-1,3,5(10)-triene
-
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
-
-
4-methylcoumarin 7-O-sulfamate
-
COUMATE, also in vivo
4-oxo-1,2,3,4-tetrahydrocyclopenta[c]chromen-7-yl sulfamate
-
-
5'-((1H-1,2,4-triazol-1-yl)methyl)-2'-cyanobiphenyl-4-yl sulfamate
-
-
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
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.02
16alpha-hydroxydehydroepiandrosterone 3-sulfate
-
-
0.217
4-methylumbelliferylsulfate
-
-
0.00313
androstenediol 3-sulfate
-
-
0.00526
cholesterol 3-sulfate
-
-
0.0067
Cholesterol sulfate
-
pH 6.4, 37C
0.014
dehydroandrosterone 3-sulfate
-
-
0.003 - 0.05
dehydroepiandrosterone 3-sulfate
0.0017 - 0.013
dehydroepiandrosterone sulfate
0.005 - 0.0506
esterone 3-sulfate
0.0063 - 0.035
Estrone 3-sulfate
0.00685 - 0.07275
Estrone sulfate
0.1 - 0.58
methylumbelliferyl sulfate
1.32
p-Nitrophenyl sulfate
-
-
1
p-nitrophenylsulfate
-
-
0.00073
pregnenolone 3-sulfate
-
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
6.48
dehydroepiandrosterone sulfate
Homo sapiens
-
pH 8, 37C
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0022
(2-(1-adamantyl)-4-oxo-4H-chromen-6-yl)(oxo)acetic acid
-
-
0.05
(2-(1-adamantyl)-4-oxo-4H-chromen-6-yl)acetic acid
-
or above
0.00025
17alpha-benzyl-17beta-hydroxyestra-1,3,5-(10)-triene-3-boronic acid
-
30C, pH 7.0
0.00025
17alpha-benzyl-3,17beta-dihydroxyestra-1,3,5-(10)-triene
-
30C, pH 7.0
0.02
2-(1-adamantyl)-4-oxo-4H-chromene-6-carbaldehyde
-
or above
0.05
2-(1-adamantyl)-4-oxo-4H-chromene-6-carboxamide
-
or above
0.0005
2-(1-adamantyl)-4-oxo-4H-chromene-6-carboxylic acid
-
-
0.05
2-(1-adamantyl)-4-oxo-4H-thiochromene-6-carbonitrile
-
or above
0.00053
2-(1-adamantyl)-4-oxo-4H-thiochromene-6-carboxylic acid
-
-
0.032
2-(1-adamantyl)-6-(hydroxymethyl)-4H-chromen-4-one
-
-
0.0032
2-(1-adamantyl)-6-glycoloyl-4H-chromen-4-one
-
-
0.000085
2-formyl-17alpha-benzyl-17beta-hydroxyestra-1,3,5(10)-triene
-
pH 7.0, temperature not specified in the publication
0.0046
2-tert-butyl-6-hydroxy-4H-chromen-4-one
-
30C, pH 7.0
0.000015
667-coumate
-
37C
0.0021 - 0.007
estra-1,3,5-(10)-triene-17-one-3-boronic acid
0.063
estrone
-
30C, pH 7.0
0.000026
KW-2581
-
37C
0.05
methyl 2-(1-adamantyl)-4-oxo-4H-chromene-6-carboxylate
-
or above
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.004633
(R)-1-[(4-cyanophenyl)(3-bromo-4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
Homo sapiens
-
enzyme activity in JEG-3 cells, IC50 for aromatase = 0.0000032 mM
0.000553
(S)-1-[(4-cyanophenyl)(3-bromo-4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
Homo sapiens
-
enzyme activity in JEG-3 cells, IC50 for aromatase = 0.0000143 mM
0.0026
1-[(4-cyanophenyl)(3-bromo-4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
Homo sapiens
-
enzyme activity in JEG-3 cells, IC50 for aromatase = 0.000003 mM
0.00092
1-[(4-cyanophenyl)(3-chloro-4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
Homo sapiens
-
enzyme activity in JEG-3 cells, IC50 for aromatase = 0.000012 mM
0.000476
1-[bis-(3-bromo-4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
Homo sapiens
-
enzyme activity in JEG-3 cells, IC50 for aromatase = 0.000043 mM
0.0000163
2',4'-dicyano-N,N-dihydroxybiphenyl-4-sulfinamide
Homo sapiens
-
-
0.000078
2-methoxy-6-oxo-6,7,8,9,10,11-hexahydrocyclohepta[c]chromen-3-yl sulfamate
Homo sapiens
-
in JEG-3 cells, pH not specified in the publication, temperature not specified in the publication
0.001
2-phenylindole sulfamate
Homo sapiens
-
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-posi
0.086
2-t-butyl-4H-1-benzopyran-4-one-6-boronic acid
Homo sapiens
-
30C, pH 7.0
0.0000326
3'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-4'-cyanobiphenyl-4-yl sulfamate
Homo sapiens
-
-
0.006333
3'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-5'-cyanobiphenyl-4-yl sulfamate
Homo sapiens
-
-
0.00016
3'-((1H-1,2,4-triazol-1-yl)methyl)-3-chlorobiphenyl-4-yl sulfamate
Homo sapiens
-
-
0.00014
3'-((1H-1,2,4-triazol-1-yl)methyl)-4'-cyanobiphenyl-4-yl sulfamate
Homo sapiens
-
-
0.0055
3'-((1H-1,2,4-triazol-1-yl)methyl)biphenyl-4-yl sulfamate
Homo sapiens
-
-
0.000032
3-oxo-1,3-dihydro-2H-cyclobuta[c]chromen-6-yl sulfamate
Homo sapiens
-
in JEG-3 cells, pH not specified in the publication, temperature not specified in the publication
0.000000035
3-sulfamoyloxy-N-3,3,3-trifluoropropyl-16,17-seco-estra-1,3,4(10)-triene-16,17-imide
Homo sapiens
-
in vitro JEG-3 cells: 0.001-10000 nmol/l inhibitor and incubation with estrone-3-sulfate, IC50 for human carbonic anhydrase II = 0.000003 mM
0.0000286
4'-((1H-1,2,4-triazol-1-yl)methyl)-2'-cyanobiphenyl-4-yl sulfamate
Homo sapiens
-
-
0.00005
4'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-2'-cyanobiphenyl-4-yl sulfamate
Homo sapiens
-
-
0.00038
4-(((4-cyanophenyl)(4H-1,2,4-triazol-4-yl)amino)methyl)-2-methoxyphenyl sulfamate
Homo sapiens
-
-
0.00004
4-fluoro-17alpha-benzyl-17beta-hydroxyestra-1,3,5(10)-triene
Homo sapiens
-
pH 7.0, temperature not specified in the publication
0.000007
4-oxo-1,2,3,4-tetrahydrocyclopenta[c]chromen-7-yl sulfamate
Homo sapiens
-
in JEG-3 cells, pH not specified in the publication, temperature not specified in the publication
0.000035
5'-((1H-1,2,4-triazol-1-yl)methyl)-2'-cyanobiphenyl-4-yl sulfamate
Homo sapiens
-
-
0.0000055
5'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-2'-cyanobiphenyl-4-yl sulfamate
Homo sapiens
-
-
0.01
5-(((4-cyanophenyl)(4H-1,2,4-triazol-4-yl)amino)methyl)-2-methoxyphenyl sulfamate
Homo sapiens
-
-
0.0024
5-methyl-6-oxo-6,7,8,9,10,11-hexahydro-5H-cyclohepta[c]quinolin-3-yl sulfamate
Homo sapiens
-
pH not specified in the publication, temperature not specified in the publication
0.0016
6-oxo-6,7,8,9,10,11,12,13,14,15,16,17,18,19-tetradecahydrocyclopentadeca[c]chromen-3-yl sulfamate
Homo sapiens
-
in JEG-3 cells, pH not specified in the publication, temperature not specified in the publication
0.00022
6-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydrocyclotrideca[c]chromen-3-yl sulfamate
Homo sapiens
-
in JEG-3 cells, pH not specified in the publication, temperature not specified in the publication
0.000000015
6-oxo-6,7,8,9,10,11,12,13,14,15-decahydrocycloundeca[c]chromen-3-yl sulfamate
Homo sapiens
-
in JEG-3 cells, pH not specified in the publication, temperature not specified in the publication
0.000000022
6-oxo-6,7,8,9,10,11,12,13-octahydrocyclonona[c]chromen-3-yl sulfamate
Homo sapiens
-
in JEG-3 cells, pH not specified in the publication, temperature not specified in the publication
0.00024
6-oxo-6,7,8,9,10,11-hexahydro-5H-cyclohepta[c]quinolin-3-yl sulfamate
Homo sapiens
-
pH not specified in the publication, temperature not specified in the publication
0.001
6-oxo-6,7,8,9,10,11-hexahydro-5H-cyclohepta[c]quinolin-3-ylsulfamide
Homo sapiens
-
above, pH not specified in the publication, temperature not specified in the publication
0.000283
6-oxo-6,7,8,9,10,11-hexahydrocyclohepta[c]chromen-2-yl sulfamate
Homo sapiens
-
in JEG-3 cells, pH not specified in the publication, temperature not specified in the publication
0.01
6-oxo-6,7,8,9,10,11-hexahydrocyclohepta[c]chromen-3-yl dimethylsulfamate
Homo sapiens
-
above, in JEG-3 cells, pH not specified in the publication, temperature not specified in the publication
0.0000015
6-oxo-6,7,8,9,10,11-hexahydrocyclohepta[c]chromen-3-yl sulfamate
Homo sapiens
-
in JEG-3 cells, pH not specified in the publication, temperature not specified in the publication
0.0001
6-oxo-7,8,9,10,11,12,13,14,15,16-decahydro-6H-cyclododeca[c]-chromen-3-yl sulfamate
Homo sapiens
-
in JEG-3 cells, pH not specified in the publication, temperature not specified in the publication
0.000000025
6-oxo-7,8,9,10,11,12,13,14-octahydro-6H-cyclodeca[c]chromen-3-yl sulfamate
Homo sapiens
-
in JEG-3 cells, pH not specified in the publication, temperature not specified in the publication
0.0000009
6-oxo-7,8,9,10-tetrahydro-6H-benzo[c]chromen-3-yl sulfamate
Homo sapiens
-
in JEG-3 cells, pH not specified in the publication, temperature not specified in the publication
0.00000043 - 0.0000051
6-oxo-8,9,10,11-tetrahydro-7H-cyclohepta-[c][1]benzopyran-3-O-sulfamate
0.171
6-oxo-8,9,10,11-tetrahydro-7H-cylohepta-[c][1]benzopyran-boronic acid
Homo sapiens
-
30C, pH 7.0
0.0000029
667-coumate
Homo sapiens
-
37C
0.00000008 - 0.0000032
estrone-3-sulfamate
0.000015
KW-2581
Homo sapiens
-
37C
0.0000015
N,N-dihydroxy-6-oxo-6,7,8,9,10,11-hexahydrocyclohepta[c]chromene-3-sulfinamide
Homo sapiens
-
-
0.00000018
STX213
Homo sapiens
-
in vitro JEG-3 cells: 0.001-10000 nmol/l inhibitor and incubation with estrone-3-sulfate, IC50 for human carbonic anhydrase II = 0.000005 mM
0.0000015 - 0.000008
STX64
0.0061
sulfamic acid 2-bromo-4-(2-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)ethyl)phenyl ester
Homo sapiens
-
inhibition of STS activity in JEG-3 cells tested with concentrations of 0.001-10000 nmol/l, IC50 for aromatase = 0.000001 mM
0.0055
sulfamic acid 2-bromo-4-(3-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)propyl)phenyl ester
Homo sapiens
-
inhibition of STS activity in JEG-3 cells tested with concentrations of 0.001-10000 nmol/l, IC50 for aromatase = 0.0000015 mM
0.000039
sulfamic acid 2-bromo-4-[[(4-cyanophenyl)[1,2,4]triazol-4-ylamino]methyl]phenyl ester
Homo sapiens
-
-
0.0015
sulfamic acid 2-chloro-4-(2-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)ethyl)phenyl ester
Homo sapiens
-
inhibition of STS activity in JEG-3 cells tested with concentrations of 0.001-10000 nmol/l, IC50 for aromatase = 0.0000017 mM
0.0012
sulfamic acid 2-chloro-4-(2-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)ethylsulfanyl)phenyl ester
Homo sapiens
-
inhibition of STS activity in JEG-3 cells tested with concentrations of 0.001-10000 nmol/l, IC50 for aromatase = 0.00000045 mM
0.0015
sulfamic acid 2-chloro-4-(3-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)propyl)phenyl ester
Homo sapiens
-
inhibition of STS activity in JEG-3 cells tested with concentrations of 0.001-10000 nmol/l, IC50 for aromatase = 0.0000021 mM
0.0035
sulfamic acid 3-(((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)methylsulfanyl)phenyl ester
Homo sapiens
-
inhibition of STS activity in JEG-3 cells tested with concentrations of 0.001-10000 nmol/l, IC50 for aromatase = 0.0000039 mM
0.01
sulfamic acid 3-(2-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)-ethylsulfanyl)phenyl ester
Homo sapiens
-
larger than 0.01 mM, inhibition of STS activity in JEG-3 cells tested with concentrations of 0.001-10000 nmol/l, IC50 for aromatase = 0.0000017 mM
0.0009
sulfamic acid 4-(((4-cyanophenyl)-(1,2,4)triazol-4-ylamino)methylsulfanyl)phenyl ester
Homo sapiens
-
inhibition of STS activity in JEG-3 cells tested with concentrations of 0.001-10000 nmol/l, IC50 for aromatase = 0.0000055 mM, best STS inhibitor of tested dual inhibitors
0.01
sulfamic acid 4-((2-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)-ethyl)methylsulfamoyl)phenyl ester
Homo sapiens
-
larger than 0.01 mM, inhibition of STS activity in JEG-3 cells tested with concentrations of 0.001-10000 nmol/l, IC50 for aromatase = 0.00001 mM
0.0019
sulfamic acid 4-(10-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)decylsulfanyl)phenyl ester
Homo sapiens
-
inhibition of STS activity in JEG-3 cells tested with concentrations of 0.001-10000 nmol/l, IC50 for aromatase = 0.0000055 mM
0.01
sulfamic acid 4-(2-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)-ethyl)phenyl ester
Homo sapiens
-
larger than 0.01 mM, inhibition of STS activity in JEG-3 cells tested with concentrations of 0.001-10000 nmol/l, IC50 for aromatase = 0.0000021 mM
0.01
sulfamic acid 4-(2-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)-ethylsulfanylmethyl)phenyl ester
Homo sapiens
-
larger than 0.01 mM, inhibition of STS activity in JEG-3 cells tested with concentrations of 0.001-10000 nmol/l, IC50 for aromatase = 0.00000037 mM
0.0026
sulfamic acid 4-(2-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)ethyl)-2-fluorophenyl ester
Homo sapiens
-
inhibition of STS activity in JEG-3 cells tested with concentrations of 0.001-10000 nmol/l, IC50 for aromatase = 0.000002 mM
0.0016
sulfamic acid 4-(3-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)-propyl)-2-fluorophenyl ester
Homo sapiens
-
inhibition of STS activity in JEG-3 cells tested with concentrations of 0.001-10000 nmol/l, IC50 for aromatase = 0.0000025 mM
0.01
sulfamic acid 4-(3-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)propyl)phenyl ester
Homo sapiens
-
larger than 0.01 mM, inhibition of STS activity in JEG-3 cells tested with concentrations of 0.001-10000 nmol/l, IC50 for aromatase = 0.00000089 mM
0.01
sulfamic acid 4-(3-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)propylsulfanyl)phenyl ester
Homo sapiens
-
inhibition of STS activity in JEG-3 cells tested with concentrations of 0.001-10000 nmol/l, IC50 larger than 0.01 mM, IC50 for aromatase = 0.00000051 mM
0.001
sulfamic acid 4-(5-((4-cyanophenyl)-[1,2,4]triazol-4-ylamino)pentylsulfanyl)phenyl ester
Homo sapiens
-
inhibition of STS activity in JEG-3 cells tested with concentrations of 0.001-10000 nmol/l, IC50 for aromatase = 0.00000073 mM
0.00059
sulfamic acid 5-[[(4-cyanophenyl)[1,2,4]triazol-4-ylamino]-methyl]-2-fluorophenyl ester
Homo sapiens
-
-
0.00000076 - 0.0000053
TX-1299
-
0.0000225
TX-1492
Homo sapiens
-
non-steroid Theramex compound, strong inhibitor, IC50: 22.5 nM in JEG-3 cells
-
0.00000006 - 0.0000119
TX-1506
-
additional information
1-[(4-cyanophenyl)(4-sulfamoyloxyphenyl)methyl]-1H-[1,2,4]triazole
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.0000128
-
pH 7.5, 37C, subcortical white matter
0.000015
-
in primary mammary carcinoma
0.0000265
-
pH 7.5, 37C, cerebral neocortex
0.385
-
pH 6.4, 37C
1.52
-
-
1.556
-
pH 8, 37C, hydrolysis of dehydroepiandrosterone sulfate
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5 - 5.5
6.9
-
f-form
7 - 7.2
-
-
7 - 7.5
-
STS from temporal lobe
7.3 - 7.5
7.3
-
p-nitrophenyl sulfate
7.5 - 8
-
placenta
7.7
-
fast form
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.1
-
isoelectric focussing, pH-gradient 2-10
8.7
-
isoelectric focusing
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
human embryonic kidney carcinoma cell line selected for overexpression of transfected His6-tagged STS cDNA to aid purification of the His6-tagged STS protein and subsequent antibody production in mice and rabbits
Manually annotated by BRENDA team
-
choriocarcinoma cell line used for expression test for transfection experiments
Manually annotated by BRENDA team
-
ER positive human breast cancer cells, used for transfection and activity experiments, shows STS activity by itself in contrast to monkey COS-1 cells used for the same experiments
Manually annotated by BRENDA team
-
transcription is regulated by two promoters which differ from the prevalent placental one. Specific activity of adipose tissue enzyme is about 50-100 times lower than by placenta enzyme
Manually annotated by BRENDA team
-
adult, relatively high STS activity
Manually annotated by BRENDA team
-
analysis of enzyme activity and sulfuryl trasnferase activity in the 55 most frequent human brain tumors
Manually annotated by BRENDA team
-
endometrial tumor, evaluation of aromatase and steryl-sulfatase activites using tritium-labeled steroids
Manually annotated by BRENDA team
-
from 10 patients in follicular and early luteal phases during gynecological laparotomy, epithelium, expression pattern
Manually annotated by BRENDA team
-
from normal and malignant breast tissue, study of the regulation of STS mRNA expression, expression in fibroblasts derived from breast tissue proximal to tumors, breast tumor tissue and reduction mammoplasty tissue, effect of menopausal status
Manually annotated by BRENDA team
-
luteinized, follicle
Manually annotated by BRENDA team
-
scalp biopsies, beard and occipital hair follicles ex vivo, predominantly expressed in the dermal papilla
Manually annotated by BRENDA team
-
human embryonic kidney carcinoma cell line
Manually annotated by BRENDA team
-
acute myeloid leukaemia cell line
Manually annotated by BRENDA team
-
human prostate cancer cells with mutated androgen receptor, as is typical for many human prostate tumors
Manually annotated by BRENDA team
-
adult
Manually annotated by BRENDA team
-
strong positive immunostaining for enzyme
Manually annotated by BRENDA team
-
peripheral blood lymphocyte
Manually annotated by BRENDA team
-
from normal mammary tissue, slightly lower STS mRNA expression but 120times higher STS activity than in MCF-7 cells
Manually annotated by BRENDA team
-
stably transfected breast cancer cells
Manually annotated by BRENDA team
-
the MCS-2 cell line is established by introduction of the human STS gene into estrogen-dependent human breast cancer MCF-7 cells, MCS-2 cells are transplanted into female nude mice
Manually annotated by BRENDA team
-
primary myoepithelial cell, highest activity of steryl sulfatase and aryl sulfatase B of all the cell lines tested
Manually annotated by BRENDA team
-
acute myeloid leukaemia cell line
Manually annotated by BRENDA team
-
adult
Manually annotated by BRENDA team
-
luteinized granulosa cells
Manually annotated by BRENDA team
-
human ovarian cancer cell line
Manually annotated by BRENDA team
-
gene expression of both sulfotransferase and steroid sulfatase in all prostate cancer cell lines examined, accompanied by synthesis of estrone and estradiol. 85% of cell lines show immunoreactivity for steroid sulfatase
Manually annotated by BRENDA team
-
remarkably low activity of arylsulfatase A, arylsulfatase B, galacose 6-sulfatase and steryl sulfatase, but not iduronate 2-sulfatase
Manually annotated by BRENDA team
-
human female vascular smooth muscle cell line
Manually annotated by BRENDA team
-
1-3.7% of the mRNA levels of placenta, adult
Manually annotated by BRENDA team
-
STS expression levels are higher in the vascular smooth muscle cells obtained from female aortas with mild atherosclerotic changes than in those with severe atherosclerotic changes in male aortas regardless of atherosclerotic changes
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
-
STS is a membrane-bound microsomal enzyme
-
Manually annotated by BRENDA team
-
membrane-bound
Manually annotated by BRENDA team
additional information
-
subcellular distribution of STS in the temporal lobe
-
Manually annotated by BRENDA team
PDB
SCOP
CATH
ORGANISM
UNIPROT
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
61000
-
SDS-PAGE, immunoblot analysis with specific antibody
30000
-
x * 30000, SDS-PAGE
54000
-
amino acid analysis
65000
-
x * 65000, SDS-PAGE
73000
-
placenta, SDS-PAGE
74000
-
gel filtration
78000
-
1 * 78000, solubilized in Triton X-100; alpha, 3 * 78000, SDS-PAGE,solubilized in Triton X-100
103000 - 105000
-
brain
183000
-
placenta, s-form, gel filtration, two isoforms s- and f-form
200000
-
liver, f-form, gel filtration, two isoforms s- and f-form
238000
-
gel filtration
250000
-
gel filtration
270000
390000
-
placenta, gel filtration
440000
-
placenta
500000 - 600000
-
placenta, gel filtration
additional information
-
native PAGE analysis of solubilized single crystals of ES shows all possible oligomeric states between a monomer and a tetramer, but predominantly the monomeric and dimeric states
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dimer
-
coprecipitation of mutant enzyme with FLAG-tagged enzyme
monomer
-
1 * 78000, solubilized in Triton X-100
trimer
-
alpha, 3 * 78000, SDS-PAGE,solubilized in Triton X-100
additional information
-
all oligomeric states between a monomer and a tetramer are possible, varying aggregation properties of enzyme under various buffer, pH, detergent and ionic strength conditions, gel filtration suggests ES to be predominantly a homotetramer, native PAGE analysis of solubilized single crystals of ES shows all possible oligomeric states between a monomer and a tetramer, but predominantly the monomeric and dimeric states
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
glycoprotein
-
4 potential glycosylation sites
glycoprotein
proteolytic modification
-
enzyme expression is driven by six different promoters giving rise to transcripts with unique first exons. Whatever ATG is actually used, the differences on protein level are restricted to the signal peptide which is post-transcriptionally cleaved
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
crystal structure analysis of placenta microsome enzyme, overview
-
full-length, active enzyme form, X-ray analysis
-
in complex with inhibitor sulfamic acid 2-bromo-4-[[(4-cyanophenyl)[1,2,4]triazol-4-ylamino]methyl]phenyl ester
-
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
37
-
5 h, 20% loss of activity
57
-
s-form: 50% loss of activity
80
-
5 min, 100% residual activity
100
-
5 min, 87% residual activity
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
room temperature, crystalline state of enzyme, more than 30 days, less than 33% loss of specific activity
-
room temperature, n-octyl-beta-D-glucopyranoside, several weeks, nearly stable
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
affinity chromatography with NiCl2-primed HisTrap Chelating columns and concentrated 6-fold using ICON concentrators
-
enzyme does not copurify with oestrone sulfate sulfohydrolase
-
of the recombinant protein
-
solubilized with 0.5% Triton X-100, two fractions with cholesterol sulfate sulfohydrolase activity are separated by DEAE-cellulose chromatography, purification of the 30 kDa enzyme
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
His6-tagged wild-type STS cDNA subcloned into pCEP4, transfected into 293-EBNA cells, cell line with stable overexpression of STS-His6 selected for production of tagged wildtype STS, subsequent specific antibody production, mutated STS is transfected into human MCF-7 cells and monkey COS-1 cells to test for STS activity by immunoblotting
-
2.4 kb STS cDNA, expression in MCF-7 and COS-1 cells
-
expression in Escherichia coli and CHO cells
-
expression in monkey kidney COS-1 cells
-
expression in mouse A9 cells
-
overexpression of STS gene in human breast cancer MCF-7 cells, i.e. MCS-2 cells, transplanted in female nude mice
-
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
shikonin, an ingredient of Lithospermum erythrorhizon, down-regulates the expression and activity of steroid sulfatase in breast cancer cells
-
Shu-Gan-Liang-Xue decoction down-regulates the expression of steroid sulfatase genes in human breast carcinoma MCF-7 cells in a dose-dependent manner
-
steroid sulfatase expression is upregulated in breast carcinomas
-
trichostatin A treatment suppresses STS mRNA expression
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
DELTA1-21
-
lacks 21 N-terminal amino acids, that encode the signal peptide, reduced STS activity
DELTA185-583
-
lacks 399 C-terminal amino acids, reduced STS activity
H136F
-
point mutation in histidine 136, reduced STS activitiy
H136W
-
point mutation in histidine 136, reduced STS activity
H136Y
-
point mutation in histidine 136, reduced STS activity
N259Q
-
point mutation in asparagine 259 glycosylation site, reduced STS activity
N333Q
-
point mutation in other potential glycosylation site asparagine 333, no reduced STS activity
N459Q
-
point mutation in other potential glycosylation site asparagine 459, no reduced STS activity
N47Q
-
point mutation in asparagine 47 glycosylation site, reduced STS activity
N47Q/N259Q
-
double mutation in asparagine 47 and 259 glycosylation sites, reduced STS activity
N54Q
-
point mutation in in asparagine 54 non-glycosylation site , no reduced STS activity
P212G
-
point mutation in proline 212, no reduced STS activity
C446Y
-
patient with X-linked ichthyosis
H444R
-
patient with X-linked ichthyosis
Q560P
-
no effect of mutation on enzyme synthesis and degradation, dominant negative effect on enzyme activity when coexisting with wild-type enzyme
R419S
-
patient with X-linked ichthyosis
S341L
-
patient with X-linked ichthyosis
W372P
-
patient with X-linked ichthyosis
W372R
-
patient with X-linked ichthyosis
additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
analysis
-
method for the evaluation of aromatase and steryl-sulfatase activites in endometrial tumors using tritium-labeled steroids
medicine
pharmacology
additional information
-
gene expression of both sulfotransferase and steroid sulfatase in all prostate cancer cell lines examined, accompanied by synthesis of estrone and estradiol. 85% of cell lines show immunoreactivity for steroid sulfatase