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Literature summary for 2.8.2.2 extracted from

  • Bansal, S.; Lau, A.J.
    Inhibition of human sulfotransferase 2A1-catalyzed sulfonation of lithocholic acid, glycolithocholic acid, and taurolithocholic acid by selective estrogen receptor modulators and various analogs and metabolites (2019), J. Pharmacol. Exp. Ther., 369, 389-405 .
    View publication on PubMed
Search for more literature for 2.8.2.2

Cloned(Commentary)

Cloned (Comment) Organism
gene SULT2A1, recombinant expression Homo sapiens

Inhibitors

Inhibitors Comment Organism Structure
4'-hydroxytoremifene
-
 Homo sapiens
4-hydroxytoremifene
-
 Homo sapiens
7-methoxylasofoxifene
-
 Homo sapiens
acolbifene
-
 Homo sapiens
arzoxifene full mixed inhibition Homo sapiens
bazedoxifene full noncompetitive inhibition Homo sapiens
bazedoxifene N-oxide
-
 Homo sapiens
cis-4-(1,2,3,4-tetrahydro-6-methoxy-2-phenyl-1-naphthalenyl)phenol
-
 Homo sapiens
clomifene full competitive inhibition Homo sapiens
des(1-azepanyl)ethylbazedoxifene
-
 Homo sapiens
droloxifene partial mixed inhibition Homo sapiens
glycolithocholic acid substrate inhibition Homo sapiens
lasofoxifene full noncompetitive inhibition Homo sapiens
lithocholic acid substrate inhibition Homo sapiens
additional information inhibition of human sulfotransferase 2A1-catalyzed sulfonation of lithocholic acid (LCA), glycolithocholic acid (GLCA), and taurolithocholic acid (TLCA) by selective estrogen receptor modulators and various analogs and metabolites. The triphenylethylene, benzothiophene, tetrahydronaphthalene, indole, and and benzopyran classes of selective estrogen receptor modulator (SERM) inhibit LCA, GLCA, and TLCA sulfonation, mode of inhibition, and MIC values, overview. Bazedoxifene and raloxifene are the most effective inhibitors of LCA, GLCA, and TLCA sulfonation, while tamoxifen is the least potent inhibitor. No inhibition by amoxicillin. The order of inhibition of LCA sulfonation by toremifene and its oxidative metabolites is N-desmethyl-4-hydroxytoremifene > 4-hydroxytoremifene > toremifene > N-desmethyltoremifene Homo sapiens
N-desmethyl-4-hydroxytoremifene
-
 Homo sapiens
N-desmethyltoremifene
-
 Homo sapiens
nafoxidine
-
 Homo sapiens
ospemifene
-
 Homo sapiens
raloxifene raloxifene is linked to the development of cholestasis, and it inhibits sulfotransferase 2A1 (SULT2A1)-catalyzed dehydroepiandrosterone (DHEA) sulfonation, full noncompetitive inhibition Homo sapiens
tamoxifen tamoxifen is linked to the development of cholestasis, and it inhibits sulfotransferase 2A1 (SULT2A1)-catalyzed dehydroepiandrosterone (DHEA) sulfonation Homo sapiens
taurolithocholic acid substrate inhibition Homo sapiens
toremifene
-
 Homo sapiens

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.00034
-
 lithocholic acid recombinant SULT2A1, pH 7.4, 37°C Homo sapiens
0.0004
-
 taurolithocholic acid liver cytosol, pH 7.4, 37°C Homo sapiens
0.00048
-
 glycolithocholic acid recombinant SULT2A1, pH 7.4, 37°C Homo sapiens
0.00099
-
 glycolithocholic acid liver cytosol, pH 7.4, 37°C Homo sapiens
0.0011
-
 lithocholic acid liver cytosol, pH 7.4, 37°C Homo sapiens

Localization

Localization Comment Organism GeneOntology No. Textmining
cytosol
-
 Homo sapiens 5829
-

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
3'-phosphoadenylyl sulfate + dehydroepiandrosterone Homo sapiens
-
 adenosine 3',5'-bisphosphate + dehydroepiandrosterone 3-sulfate
-
 ?
3'-phosphoadenylyl sulfate + glycolithocholic acid Homo sapiens
-
 adenosine 3',5'-bisphosphate + glycolithocholate 3-sulfate
-
 ?
3'-phosphoadenylyl sulfate + lithocholic acid Homo sapiens
-
 adenosine 3',5'-bisphosphate + lithocholate 3-sulfate
-
 ?
3'-phosphoadenylyl sulfate + taurolithocholic acid Homo sapiens
-
 adenosine 3',5'-bisphosphate + taurolithocholate 3-sulfate
-
 ?

Organism

Organism UniProt Comment Textmining
Homo sapiens Q06520
-
-

Source Tissue

Source Tissue Comment Organism Textmining
Hep-G2 cell
-
 Homo sapiens
-
hepatoma cell
-
 Homo sapiens
-
liver
-
 Homo sapiens
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3'-phosphoadenylyl sulfate + (S)-dehydroepiandrosterone
-
 Homo sapiens adenosine 3',5'-bisphosphate + (S)-dehydroepiandrosterone 3-sulfate
-
 ?
3'-phosphoadenylyl sulfate + dehydroepiandrosterone
-
 Homo sapiens adenosine 3',5'-bisphosphate + dehydroepiandrosterone 3-sulfate
-
 ?
3'-phosphoadenylyl sulfate + glycolithocholic acid
-
 Homo sapiens adenosine 3',5'-bisphosphate + glycolithocholate 3-sulfate
-
 ?
3'-phosphoadenylyl sulfate + lithocholic acid
-
 Homo sapiens adenosine 3',5'-bisphosphate + lithocholate 3-sulfate
-
 ?
3'-phosphoadenylyl sulfate + taurolithocholic acid
-
 Homo sapiens adenosine 3',5'-bisphosphate + taurolithocholate 3-sulfate
-
 ?

Synonyms

Synonyms Comment Organism
More see also EC 2.8.2.14 Homo sapiens
sulfotransferase 2A1
-
 Homo sapiens
SULT2A1
-
 Homo sapiens

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
37
-
 assay at Homo sapiens

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.4
-
 assay at Homo sapiens

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
additional information
-
 additional information inhibition kinetics and modeling, detailed overview Homo sapiens
0.0002
-
 bazedoxifene liver cytosol, pH 7.4, 37°C, substrate lithocholic acid, noncompetitive inhibition Homo sapiens
0.0005
-
 raloxifene liver cytosol, pH 7.4, 37°C, substrate lithocholic acid, noncompetitive inhibition Homo sapiens
0.0008
-
 arzoxifene liver cytosol, pH 7.4, 37°C, substrate lithocholic acid, mixed inhibition Homo sapiens
0.0008
-
 lasofoxifene liver cytosol, pH 7.4, 37°C, substrate lithocholic acid, noncompetitive inhibition Homo sapiens
0.0046
-
 droloxifene liver cytosol, pH 7.4, 37°C, substrate lithocholic acid, mixed inhibition Homo sapiens
0.0057
-
 lithocholic acid liver cytosol, pH 7.4, 37°C Homo sapiens
0.0058
-
 clomifene liver cytosol, pH 7.4, 37°C, substrate lithocholic acid, competitive inhibition Homo sapiens
0.0081
-
 taurolithocholic acid liver cytosol, pH 7.4, 37°C Homo sapiens
0.0096
-
 glycolithocholic acid recombinant SULT2A1, pH 7.4, 37°C Homo sapiens
0.0123
-
 glycolithocholic acid liver cytosol, pH 7.4, 37°C Homo sapiens
0.0391
-
 lithocholic acid recombinant SULT2A1, pH 7.4, 37°C Homo sapiens

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.00006
-
 liver cytosol, pH 7.4, 37°C, substrate lithocholic acid Homo sapiens bazedoxifene N-oxide
0.00008
-
 liver cytosol, pH 7.4, 37°C, substrate taurolithocholic acid Homo sapiens arzoxifene
0.00013
-
 liver cytosol, pH 7.4, 37°C, substrate taurolithocholic acid Homo sapiens bazedoxifene
0.00016
-
 liver cytosol, pH 7.4, 37°C, substrate lithocholic acid Homo sapiens des(1-azepanyl)ethylbazedoxifene
0.00018
-
 liver cytosol, pH 7.4, 37°C, substrate taurolithocholic acid Homo sapiens raloxifene
0.0002
-
 liver cytosol, pH 7.4, 37°C, substrate glycolithocholic acid Homo sapiens arzoxifene
0.00021
-
 liver cytosol, pH 7.4, 37°C, substrate lithocholic acid Homo sapiens bazedoxifene
0.00025
-
 liver cytosol, pH 7.4, 37°C, substrate taurolithocholic acid Homo sapiens lasofoxifene
0.00028
-
 liver cytosol, pH 7.4, 37°C, substrate lithocholic acid Homo sapiens raloxifene
0.00029
-
 liver cytosol, pH 7.4, 37°C, substrate glycolithocholic acid Homo sapiens bazedoxifene
0.00029
-
 liver cytosol, pH 7.4, 37°C, substrate lithocholic acid Homo sapiens arzoxifene
0.00041
-
 liver cytosol, pH 7.4, 37°C, substrate glycolithocholic acid Homo sapiens raloxifene
0.0005
-
 liver cytosol, pH 7.4, 37°C, substrate glycolithocholic acid Homo sapiens lasofoxifene
0.00075
-
 liver cytosol, pH 7.4, 37°C, substrate taurolithocholic acid Homo sapiens droloxifene
0.001
-
 liver cytosol, pH 7.4, 37°C, substrate lithocholic acid Homo sapiens lasofoxifene
0.0014
-
 liver cytosol, pH 7.4, 37°C, substrate lithocholic acid Homo sapiens cis-4-(1,2,3,4-tetrahydro-6-methoxy-2-phenyl-1-naphthalenyl)phenol
0.0014
-
 liver cytosol, pH 7.4, 37°C, substrate taurolithocholic acid Homo sapiens nafoxidine
0.0015
-
 liver cytosol, pH 7.4, 37°C, substrate glycolithocholic acid Homo sapiens droloxifene
0.0015
-
 liver cytosol, pH 7.4, 37°C, substrate lithocholic acid Homo sapiens droloxifene
0.0015
-
 liver cytosol, pH 7.4, 37°C, substrate taurolithocholic acid Homo sapiens clomifene
0.0018
-
 liver cytosol, pH 7.4, 37°C, substrate lithocholic acid Homo sapiens 4'-hydroxytoremifene
0.0023
-
 liver cytosol, pH 7.4, 37°C, substrate taurolithocholic acid Homo sapiens ospemifene
0.00255
-
 liver cytosol, pH 7.4, 37°C, substrate glycolithocholic acid Homo sapiens ospemifene
0.0029
-
 liver cytosol, pH 7.4, 37°C, substrate lithocholic acid Homo sapiens 7-methoxylasofoxifene
0.003
-
 liver cytosol, pH 7.4, 37°C, substrate lithocholic acid Homo sapiens ospemifene
0.0032
-
 liver cytosol, pH 7.4, 37°C, substrate lithocholic acid Homo sapiens clomifene
0.0032
-
 liver cytosol, pH 7.4, 37°C, substrate taurolithocholic acid Homo sapiens toremifene
0.0036
-
 liver cytosol, pH 7.4, 37°C, substrate glycolithocholic acid Homo sapiens clomifene
0.0044
-
 liver cytosol, pH 7.4, 37°C, substrate lithocholic acid Homo sapiens 4-hydroxytoremifene
0.0066
-
 liver cytosol, pH 7.4, 37°C, substrate glycolithocholic acid Homo sapiens nafoxidine
0.007
-
 liver cytosol, pH 7.4, 37°C, substrate taurolithocholic acid Homo sapiens acolbifene
0.0092
-
 liver cytosol, pH 7.4, 37°C, substrate lithocholic acid Homo sapiens toremifene
0.0101
-
 liver cytosol, pH 7.4, 37°C, substrate glycolithocholic acid Homo sapiens acolbifene
0.0101
-
 liver cytosol, pH 7.4, 37°C, substrate taurolithocholic acid Homo sapiens tamoxifen
0.011
-
 liver cytosol, pH 7.4, 37°C, substrate glycolithocholic acid Homo sapiens toremifene
0.0122
-
 liver cytosol, pH 7.4, 37°C, substrate lithocholic acid Homo sapiens nafoxidine
0.0129
-
 liver cytosol, pH 7.4, 37°C, substrate lithocholic acid Homo sapiens acolbifene
0.0129
-
 liver cytosol, pH 7.4, 37°C, substrate lithocholic acid Homo sapiens N-desmethyl-4-hydroxytoremifene
0.0137
-
 liver cytosol, pH 7.4, 37°C, substrate glycolithocholic acid Homo sapiens tamoxifen
0.0163
-
 liver cytosol, pH 7.4, 37°C, substrate lithocholic acid Homo sapiens tamoxifen
0.0184
-
 liver cytosol, pH 7.4, 37°C, substrate lithocholic acid Homo sapiens N-desmethyltoremifene

General Information

General Information Comment Organism
malfunction tamoxifen or raloxifene are linked to the development of cholestasis, and inhibit sulfotransferase 2A1 (SULT2A1)-catalyzed dehydroepiandrosterone (DHEA) sulfonation Homo sapiens