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
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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
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
bat
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
Haliotis sp.
abalone entrails
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Manually annotated by BRENDA team
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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1019024 A+, 1073575 A+, 1102044 A+, 1242170 A+, 135613 A+, 1365994 A+, 1586570 A+, 1586689 A+, 1587203 A+, 1587206 A+, 1587224 A+, 1587237 A+, 1587269 A+, 1587346 A+, 1587350 A+, 1587354 A+, 1587359 A+, 1587363 A+, 1587485 A+, 1587488 A+, 1587521 A+, 1587525 A+, 1587556 A+, 1587591 A+, 1587593 A+, 1587616 A+, 1587630 A+, 1587635 A+, 1587644 A+, 1587684 A+, 1587775 A+, 1587782 A+, 1587786 A+, 1587791 A+, 1587838 A+, 1587839 A+, 1587846 A+, 1587857 A+, 1587901 A+, 1587926 A+, 2201028 A+, 2201240 A+, 2201245 A+, 2201251 A+, 2201255 A+, 2201266 A+, 2201272 A+, 2201273 A+, 2201305 A+, 2201344 A+, 2371641 A+, 2460205 A+, 2678011 A+, 2678045 A+, 2678051 A+, 2678104 A+, 2678113 A+, 2678178 A+, 2678179 A+, 2678207 A+, 2678248 A+, 2678293 A+, 2678316 A+, 2678326 A+, 2678404 A+, 2678428 A+, 2678476 A+, 2678490 A+, 2678582 A+, 2678612 A+, 2678672 A+, 2678740 A+, 656370 A+, 841500 A+, 917929 A+, 918176 A+, 918178 A+, 918240 A+, 918241 A+, 918242 A+, 918243 A+, 918244 A+, 918245 A+, 918246 A+, 918247 A+, 918248 A+, 918254 A+, 918255 A+, 918282 A+, 918304 A+, 918327 A+, 918386 A+, 918413 A+, 135623 A++, 1587042 A++, 1587504 A++, 1587950 A++, 2201221 A++, 2201247 A++, 2201249 A++, 2201261 A++, 2201276 A++, 656638 A++, 656639 A++, 656649 A++, 656650 A++, 694116 A++, 918280 A++, 918299 A++, 918306 A++, 918345 A++, 1586466 A++, 1587272 A++, 1587289 A++, 1587443 A++, 1587570 A++, 2201246 A++, 2201257 A++, 2201259 A++, 2201260 A++, 2201268 A++, 2201288 A++, 2201289 A++, 2201295 A++, 2201314 A++, 2677637 A++, 663843 A++, 681644 A++, 918301 A++, 730284 A+++, 918203 A+++, 918273 A+++, 918348 A+++, 918379 A+++, 918389 A+++, 135607 A++++, 917685 A++++, 918200 A++++, 918202 A++++, 918205 A++++, 918207 A++++, 918212 A++++, 918221 A++++, 918227 A++++, 918293 A++++, 918294 A++++, 918318 A++++
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Automatic Mining of ENzyme DAta
squirrel
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
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Automatic Mining of ENzyme DAta
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
metabolism
physiological function
additional information
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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
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?
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
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?
4-methylumbelliferyl sulfate + H2O
4-methylumbelliferone + sulfate
show the reaction diagram
4-methylumbelliferyl-6-O-sulfate + H2O
4-methylumbelliferone + sulfate
show the reaction diagram
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?
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
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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
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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
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-
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
-
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
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4'-((1H-1,2,4-triazol-1-yl)methyl)-3-chloro-2'-cyanobiphenyl-4-yl sulfamate
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4-(((4-cyanophenyl)(4H-1,2,4-triazol-4-yl)amino)methyl)-2-methoxyphenyl sulfamate
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4-(trifluoromethyl)coumarin 7-O-sulfamate
-
-
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-methylcoumarin-7-O-sulfamate
-
-
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
-
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
-
-
AgNO3
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
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
-
-
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
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
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
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
-