Information on EC 3.1.6.2 - steryl-sulfatase

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

EC NUMBER
COMMENTARY hide
3.1.6.2
-
RECOMMENDED NAME
GeneOntology No.
steryl-sulfatase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
3beta-hydroxyandrost-5-en-17-one 3-sulfate + H2O = 3beta-hydroxyandrost-5-en-17-one + sulfate
show the reaction diagram
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
hydrolysis of sulfuric ester
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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
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Haliotis sp.
abalone entrails
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
Sus scrofa steroid sulfatase (StS) mRNA, partial cds from boar testis; 5 age groups 50, 100, 150, 250 days old boars, remarkably high testicular estrogen output
UniProt
Manually annotated by BRENDA team
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
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
-
-
-
-
?
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
-
-
-
-
?
4-nitrophenyl sulfate + H2O
4-nitrophenol + sulfate
show the reaction diagram
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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-
-
-
?
arylsulfates + H2O
? + sulfate
show the reaction diagram
-
e.g. 3alpha sulfates of: 5alpha-androstane-17-one, 5beta-androstane-17-one, 3beta sulfates of: 5alpha-androstane-17-one, DELTA5-androstene 17-one, 5alpha-pregnane-20-one, DELTA5-pregnene-20-one
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-
?
arzoxifene sulfate + H2O
arzoxifene + sulfate
show the reaction diagram
-
product of sulfotransferase reaction on arzoxifene used in hormone replacement therapy
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-
?
beta-estradiol-3-sulfate + H2O
estradiol + sulfate
show the reaction diagram
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-
?
cholesterol 3-sulfate + H2O
cholesterol + sulfate
show the reaction diagram
cholesterol sulfate + H2O
cholesterol + sulfate
show the reaction diagram
cortisone 21-sulfate + H2O
cortisone + sulfate
show the reaction diagram
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-
-
?
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
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-
-
-
?
epiandrosterone 3-sulfate + H2O
epiandrosterone + 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-acetylphenyl sulfate + H2O
p-acetylphenol + sulfate
show the reaction diagram
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-
-
-
?
p-nitrocatechol sulfate + H2O
nitrocatechol + sulfate
show the reaction diagram
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-
?
p-nitrophenyl-sulfate + H2O
p-nitrophenol + sulfate
show the reaction diagram
phenolphthalein disulfate + H2O
phenolphthalein monosulfate + sulfate
show the reaction diagram
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?
pregnenolone 3-sulfate + H2O
pregnenolone + sulfate
show the reaction diagram
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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
steroid sulfates + H2O
steroid + sulfate
show the reaction diagram
testosterone 3-sulfate + H2O
testosterone + sulfate
show the reaction diagram
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?
additional information
?
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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
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
steroid sulfates + H2O
steroid + sulfate
show the reaction diagram
additional information
?
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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
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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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(NH4)2SO4
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slight
(p-O-sulfamoyl)-N-tetradecanoyl tyramine
(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
17-oxoestra-1,3,5(10)-trien-3-yl sulfamate
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
-
-
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
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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
-
-
-
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
-
12-fold more potent than COUMATE
3-nitrophenyl sulfamate
3-oxo-1,3-dihydro-2H-cyclobuta[c]chromen-6-yl sulfamate
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-
3-sulfamoyloxy-N-(1''-pyridin-3''-ylmethyl)-16,17-seco-estra-1,3,5(10)-triene-16,17-imide
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highly potent inhibitor, IC50: 1 nM, 18times more inhibitory than estrone-3-O-sulfamate, in vivo inhibition of STS
3-sulfamoyloxy-N-3,3,3-trifluoropropyl-16,17-seco-estra-1,3,4(10)-triene-16,17-imide
3-sulfamoyloxy-N-propyl-16,17-seco-estra-1,3,5(10)-triene-16,17-imide
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highly potent inhibitor, IC50: 1 nM, 18times more inhibitory than estrone-3-O-sulfamate, in vivo inhibition of STS
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
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-
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
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-
4-methylcoumarin 7-O-sulfamate
-
COUMATE, also in vivo
4-methylcoumarin-7-O-sulfamate
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-
4-oxo-1,2,3,4-tetrahydrocyclopenta[c]chromen-7-yl sulfamate
-
-
4-oxo-2,3-dihydro-1H-cyclopenta-[c][1]benzopyran-7-O-sulfamate
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665 COUMATE, placental IC50: 200 nM
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-7,8,9,10,11,12,13,14,15,16-decahydro-cyclododeca-[c][1]benzopyran-3-O-sulfamate
-
6612 COUMATE, placental IC50: 60 nM
6-oxo-7,8,9,10,11,12,13,14-octahydro-6H-cyclodeca[c]chromen-3-yl sulfamate
-
-
6-oxo-7,8,9,10,11,12,13,14-octahydro-cyclodeca-[c][1]benzopyran-3-O-sulfamate
-
6610 COUMATE, placental IC50: 1 nM
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-7,8,9,10,11,12-hexahydro-cycloocta-[c][1]benzopyran-3-O-sulfamate
-
668 COUMATE, placental IC50: 30 nM
6-oxo-7,8,9,10-tetrahydro-6H-benzo[c]chromen-3-yl sulfamate
-
-
6-oxo-7,8,9,10-tetrahydro-dibenzo[b,d]pyran-3-O-sulfamate
-
666 COUMATE, placental IC50: 70 nM
6-oxo-8,9,10,11,12,13,14,15,16,17,18,19-dodecahydro-7H-cyclopentadeca-[c][1]benzopyran-3-O-sulfamate
-
6615 COUMATE, placental IC50: 370 nM, most potent tricyclic coumarin sulfamate inhibitor tested in vivo
6-oxo-8,9,10,11,12,13,14,15,16,17-decahydro-7H-cyclotrideca-[c][1]benzopyran-3-O-sulfamate
-
6613 COUMATE, placental IC50: 75 nM
6-oxo-8,9,10,11,12,13,14,15-octahydro-7H-cycloundeca-[c][1]benzopyran-3-O-sulfamate
-
6611 COUMATE, placental IC50: 13 nM
6-oxo-8,9,10,11,12,13-hexahydro-7H-cyclonona-[c][1]benzopyran-3-O-sulfamate
-
669 COUMATE, placental IC50: 2.4 nM
6-oxo-8,9,10,11-tetrahydro-7H-cyclohepta-[c][1]benzopyran-3-O-sulfamate
6-oxo-8,9,10,11-tetrahydro-7H-cylohepta-[c][1]benzopyran-boronic acid
-
-
667 COUMATE
-
i.e. 6-oxo-6,7,8,9,10,11-hexahydrocyclohepta(c)chromen-3-yl sulfamate, coadministation of oestrone sulfamate and 667 COUMATE completely blocks enzyme activity and completely abrogates the ability of oestrone sulfamate to stimulate uterine growth
667-coumate
-
-
7,8-dihydronaphthalene 2-O-sulfamate
-
-
7-hydroxy-4-methylcoumarin 6-O-sulfamate
-
-
Ammonium molybdate
-
10 mM, 20% residual activity
anastrozole
-
-
breast cyst fluid
-
-
-
CaCl2
-
slight
calcium chloride
-
5 mM, 36% residual activity
cholesterol
-
1 mM, 57% inhibition
Cl-
-
slight
coumarin 7-O-sulfamate
-
-
cysteine
-
10 mM, 15% inhibition
daidzein-4'-O-sulfate
-
at 0.005 mM
daidzein-7,4'-di-O-sulfate
-
at 0.001 mM
dehydroepiandrosterone
dithiothreitol
-
5 mM, 45% residual activity
EDTA
-
10% inhibition at 1 mM
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
glucose
-
slight
glutathione
-
reduced form, 5 mM, 23.5% residual activity
H2PO4-
-
-
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
KBr
-
slight
KCl
-
slight
KCN
-
slight
KH2PO4
-
5 mM, 25% inhibition
KW-2581
-
active site-directed irreversible steroidal inhibitor
letrozole
-
-
LiCl
-
slight
Metabisulfite
-
-
methyl 2-(1-adamantyl)-4-oxo-4H-chromene-6-carboxylate
-
-
MgCl2
-
slight
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
Na-metaborate
-
-
Na-tetraborate
Na2B4O7
Na2SO3
Na2SO4
NaCl
-
slight
NaF
-
slight
NaHSO3
-
slight
p-Nitrophenyl sulfate
phosphate
pregnenolone
-
1 mM, 10% inhibition
pregnenolone 3-sulfate
-
competitive inhibitor, dehydroepiandrosterone 3-sulfate as substrate
Rose bengal
-
histidine modification
Sodium arsenite
-
slight
Sodium deoxycholate
-
-
sodium taurocholate
-
-
Steroids
STX213
STX289
-
N,N-dimethyl 667 COUMATE, analogue of STX64, inhibition 24 h after oral application: 0.1 mg/kg inhibits liver STS by 45%, skin STS by about 39%, 1 and 10 mg/kg inhibit liver STS completely, skin STS almost completely, inhibition 24 h after topical application to neck skin: 0.1 mg/kg inhibits skin and liver STS by <50%, remote skin STS by about 10%, 1and 10 mg/kg inhibit skin STS by 98%, remote skin STS by about 80 and more than 90% respectively, and liver STS by more than 80 and close by 100% respectively
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
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
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
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
Sulfate esters
-
overview, e.g. p-nitrophenyl sulfate
-
tricyclic coumarin sulfamate
-
in vitro and in vivo inhibition studies with E1-STS from different tissues, structure-activity relationship of a number of tricyclic coumarin sulfamates, the size of the third ring has a marked effect on inhibitor potency
-
TX-1299
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
Triton X-100
-
activates
Tumor necrosis factor alpha
additional information
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.02
16alpha-hydroxydehydroepiandrosterone 3-sulfate
-
-
0.217
4-methylumbelliferylsulfate
-
-
2.03 - 10.2
4-nitrophenyl sulfate
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 - 0.113
dehydroepiandrosterone 3-sulfate
0.0017 - 0.013
dehydroepiandrosterone sulfate
0.005 - 0.0506
esterone 3-sulfate
0.0063 - 0.035
Estrone 3-sulfate
0.00215 - 0.07275
Estrone sulfate
0.1 - 2.5
methylumbelliferyl sulfate
0.007 - 1600
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
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
0.035 - 1.6
3-nitrophenyl sulfamate
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
0.000001
3-sulfamoyloxy-N-(1''-pyridin-3''-ylmethyl)-16,17-seco-estra-1,3,5(10)-triene-16,17-imide
Rattus norvegicus
-
highly potent inhibitor, IC50: 1 nM, 18times more inhibitory than estrone-3-O-sulfamate, in vivo inhibition of STS
0.000000035
3-sulfamoyloxy-N-3,3,3-trifluoropropyl-16,17-seco-estra-1,3,4(10)-triene-16,17-imide
0.000001
3-sulfamoyloxy-N-propyl-16,17-seco-estra-1,3,5(10)-triene-16,17-imide
Rattus norvegicus
-
highly potent inhibitor, IC50: 1 nM, 18times more inhibitory than estrone-3-O-sulfamate, in vivo inhibition of STS
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
0.0002
4-oxo-2,3-dihydro-1H-cyclopenta-[c][1]benzopyran-7-O-sulfamate
Rattus norvegicus
-
665 COUMATE, placental IC50: 200 nM
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
0.00006
6-oxo-7,8,9,10,11,12,13,14,15,16-decahydro-cyclododeca-[c][1]benzopyran-3-O-sulfamate
Rattus norvegicus
-
6612 COUMATE, placental IC50: 60 nM
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
0.000001
6-oxo-7,8,9,10,11,12,13,14-octahydro-cyclodeca-[c][1]benzopyran-3-O-sulfamate
Rattus norvegicus
-
6610 COUMATE, placental IC50: 1 nM
0.00003
6-oxo-7,8,9,10,11,12-hexahydro-cycloocta-[c][1]benzopyran-3-O-sulfamate
Rattus norvegicus
-
668 COUMATE, placental IC50: 30 nM
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
0.00007
6-oxo-7,8,9,10-tetrahydro-dibenzo[b,d]pyran-3-O-sulfamate
Rattus norvegicus
-
666 COUMATE, placental IC50: 70 nM
0.00037
6-oxo-8,9,10,11,12,13,14,15,16,17,18,19-dodecahydro-7H-cyclopentadeca-[c][1]benzopyran-3-O-sulfamate
Rattus norvegicus
-
6615 COUMATE, placental IC50: 370 nM, most potent tricyclic coumarin sulfamate inhibitor tested in vivo
0.000075
6-oxo-8,9,10,11,12,13,14,15,16,17-decahydro-7H-cyclotrideca-[c][1]benzopyran-3-O-sulfamate
Rattus norvegicus
-
6613 COUMATE, placental IC50: 75 nM
0.000013
6-oxo-8,9,10,11,12,13,14,15-octahydro-7H-cycloundeca-[c][1]benzopyran-3-O-sulfamate
Rattus norvegicus
-
6611 COUMATE, placental IC50: 13 nM
0.0000024
6-oxo-8,9,10,11,12,13-hexahydro-7H-cyclonona-[c][1]benzopyran-3-O-sulfamate
Rattus norvegicus
-
669 COUMATE, placental IC50: 2.4 nM
0.00000043 - 0.000008
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
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
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
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
0.000002961
-
-
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
4
-
and pH 7.4, 2 optima
4.5
-
flat optimum
4.6
-
assay at
5 - 5.5
6.6
-
dehydroepiandrosterone 3-sulfate
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
7.5
-
assay at
7.7
-
fast form
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4 - 8
-
-
5 - 8.5
-
pH 5: about 25% of activity maximum, pH 8.5: about 15% of activity maximum, dehydroepiandrosterone 3-sulfate
6 - 9
-
pH 6.0: about 20% of activity maximum, pH 9.0: about 60% of activity maximum
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30 - 60
-
-
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
-
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
-
plasma estradiol levels are stimulated 3 days ahead of inhibitor application with pregnant mare's serum gonadotropin (PMSG)
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
-
male, highest enzymic activity in cerebellum followed by cortex and subcortex, female, highest activity in cortex followed by subcortex and cerebellum
Manually annotated by BRENDA team
-
male, highest enzymic activity in cerebellum followed by cortex and subcortex, female, highest activity in cortex followed by subcortex and cerebellum
Manually annotated by BRENDA team
-
male, highest enzymic activity in cerebellum followed by cortex and subcortex, female, highest activity in cortex followed by subcortex and cerebellum
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
-
scalp biopsies, beard and occipital hair follicles ex vivo, predominantly expressed in the dermal papilla
Manually annotated by BRENDA team
-
acute myeloid leukaemia cell line
Manually annotated by BRENDA team
all cells with positive StS expression,exception: 65.1% StS expression in 50-day-old animal's Leydig cells
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
-
MF-1 mice with transplanted Ishikawa cells grown into tumors
Manually annotated by BRENDA team
-
immortalized rat granulosa 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
-
low enzymic activity
Manually annotated by BRENDA team
additional information
-
subcellular distribution of STS in the temporal lobe
-
Manually annotated by BRENDA team