Classification Term: 2361

Arylsulfates (ontology term: CHEMONTID:0004258)

Organic compounds containing a sulfate group that carries an aryl group through an ether group." []

found 15 associated metabolites at sub_class metabolite taxonomy ontology rank level.

Ancestor: Organic sulfuric acids and derivatives

Child Taxonomies: Phenylsulfates

3-Indoxyl sulfate

1H-indol-3-Ol hydrogen sulfate ester

C8H7NO4S (213.0096)


Indoxyl sulfate is a dietary protein metabolite and also a metabolite of the common amino acid tryptophan. It has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821). It is a circulating uremic toxin stimulating glomerular sclerosis and interstitial fibrosis. Indoxyl sulfate is one of the well-known substances of a group of protein-bound uremic retention solutes. Indoxyl sulfate increases the rate of progression of renal failure. In plasma, indoxyl sulfate is a protein-bound uremic solute that induces endothelial dysfunction by inhibiting endothelial proliferation and migration in vitro. Some studies suggest that indoxyl sulfate is also involved in oxidative stress. In hemodialyzed patients, serum levels of indoxyl sulfate are associated with levels of pentosidine, a marker of carbonyl and oxidative stress. In vitro, indoxyl sulfate increases reactive oxygen species (ROS) production in tubular cells and increases NAD(P)H oxidase activity in endothelial cells. Indoxyl sulfate impairs osteoblast function and induces abnormalities of bone turnover. Indoxyl sulfate strongly decreases the levels of glutathione, one of the most active antioxidant systems of the cell (PMID: 10681668 , 14681860 , 17471003 , 17403109). Indoxyl sulfate is a microbial metabolite found in Escherichia (PMID: 19946322). Indoxyl sulfate is a dietary protein metabolite, and also the metabolite of the common amino acid tryptophan. Indoxyl sulfate is a circulating uremic toxin stimulating glomerular sclerosis and interstitial fibrosis. Indoxyl sulfate is one of the well known substances of a group of protein-bound uremic retention solutes. Indoxyl sulfate increases the rate of progression of renal failure. In plasma, indoxyl sulfate is a protein-bound uremic solute that induces endothelial dysfunction by inhibiting endothelial proliferation and migration in vitro. Some studies suggest that indoxyl sulfate is also involved in oxidative stress. In hemodialyzed patients, serum levels of indoxyl sulfate are associated with levels of pentosidine, a marker of carbonyl and oxidative stress; in vitro, indoxyl sulfate increases reactive oxygen species (ROS) production in tubular cells, and increases NAD(P)H oxidase activity in endothelial cells. Indoxyl sulfate impairs osteoblst function and induces abnormalities of bone turnover. Indoxyl sulfate strongly decreases the levels of glutathione, one of the most active antioxidant systems of the cell. (PMID: 10681668, 14681860, 17471003, 17403109) [HMDB]

   

5-(3',5'-Dihydroxyphenyl)-gamma-valerolactone-O-sulphate-O-methyl

5-(3,5-Dihydroxyphenyl)-gamma-valerolactone-O-sulphuric acid-O-methyl

C12H14O7S (302.046)


5-(3,5-Dihydroxyphenyl)-gamma-valerolactone-O-sulphate-O-methyl belongs to the family of Phenols and Derivatives. These are compounds containing a phenol moiety, which is a benzene bearing an hydroxyl group.

   

N-Desmethyl-o-O-sulfate rosiglitazone

{2-[(2-{4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy}ethyl)amino]pyridin-3-yl}oxidanesulfonic acid

C17H17N3O7S2 (439.0508)


N-Desmethyl-o-O-sulfate rosiglitazone is a metabolite of rosiglitazone. Rosiglitazone is an antidiabetic drug in the thiazolidinedione class of drugs. It works as an insulin sensitizer, by binding to the PPAR receptors in fat cells and making the cells more responsive to insulin. It is marketed by the pharmaceutical company GlaxoSmithKline (GSK) as a stand-alone drug (Avandia) and in combination with metformin (Avandamet) or with glimepiride (Avandaryl). Annual sales peaked at approximately $2.5bn in 2006, but declined after reports of adverse effects. (Wikipedia)

   

N-Desmethyl-p-O-sulfate rosiglitazone

{6-[(2-{4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy}ethyl)amino]pyridin-3-yl}oxidanesulfonic acid

C17H17N3O7S2 (439.0508)


N-Desmethyl-p-O-sulfate rosiglitazone is a metabolite of rosiglitazone. Rosiglitazone is an antidiabetic drug in the thiazolidinedione class of drugs. It works as an insulin sensitizer, by binding to the PPAR receptors in fat cells and making the cells more responsive to insulin. It is marketed by the pharmaceutical company GlaxoSmithKline (GSK) as a stand-alone drug (Avandia) and in combination with metformin (Avandamet) or with glimepiride (Avandaryl). Annual sales peaked at approximately $2.5bn in 2006, but declined after reports of adverse effects. (Wikipedia)

   

o-O-sulfate rosiglitazone

{2-[(2-{4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy}ethyl)(methyl)amino]pyridin-3-yl}oxidanesulfonic acid

C18H19N3O7S2 (453.0664)


o-O-sulfate rosiglitazone is a metabolite of rosiglitazone. Rosiglitazone is an antidiabetic drug in the thiazolidinedione class of drugs. It works as an insulin sensitizer, by binding to the PPAR receptors in fat cells and making the cells more responsive to insulin. It is marketed by the pharmaceutical company GlaxoSmithKline (GSK) as a stand-alone drug (Avandia) and in combination with metformin (Avandamet) or with glimepiride (Avandaryl). Annual sales peaked at approximately $2.5bn in 2006, but declined after reports of adverse effects. (Wikipedia)

   

3-Hydroxy-4-aminopyridine sulfate

(4-aminopyridin-3-yl)oxidanesulfonic acid

C5H6N2O4S (190.0048)


3-Hydroxy-4-aminopyridine sulfate is a metabolite of dalfampridine. 4-Aminopyridine (fampridine, dalfampridine) is an organic compound with the chemical formula C5H4N–NH2. The molecule is one of the three isomeric amines of pyridine. It is used primarily as a research tool, in characterizing subtypes of potassium channel, and has also been used to manage some of the symptoms of multiple sclerosis, and is indicated for symptomatic improvement of walking in adults with several variations of the disease. (Wikipedia)

   

6-Hydroxyindole sulfate

(1H-indol-6-yl)oxidanesulfonic acid

C8H7NO4S (213.0096)


6-Hydroxyindole sulfate belongs to the class of organic compounds known as arylsulfates. These are organic compounds containing a sulfate group that carries an aryl group through an ether group. 6-Hydroxyindole sulfate has been identified in blood (PMID: 31250215).

   

3-Hydroxypyridine sulfate

(pyridin-3-yl)oxidanesulfonic acid

C5H5NO4S (174.9939)


3-Hydroxypyridine sulfate belongs to the class of organic compounds known as arylsulfates. These are organic compounds containing a sulfate group that carries an aryl group through an ether group. 3-Hydroxypyridine sulfate is a potential urinary biomarker of whole grain intake (PMID: 27805021).

   

7-Hydroxyindole sulfate

(1H-indol-7-yl)oxidanesulfonic acid

C8H7NO4S (213.0096)


7-Hydroxyindole sulfate belongs to the class of organic compounds known as arylsulfates. These are organic compounds containing a sulfate group that carries an aryl group through an ether group. 7-Hydroxyindole sulfate is a uremic toxin (PMID: 30087103).

   

3-Methoxycatechol sulfate

5,6-dihydroxy-4-methoxy-1,3,2lambda6-benzodioxathiole-2,2-dione

C7H6O7S (233.9834)


   

4-Methylcatechol sulfate

6,7-dihydroxy-9-methyl-2,4-dioxa-3lambda6-thiabicyclo[3.3.1]nona-1(9),5,7-triene-3,3-dione

C7H6O6S (217.9885)


   

3-Ethylphenylsulfate

3-Ethylphenylsulphuric acid

C16H18O4S (306.0926)


   

Diphenyl sulfate

Diphenyl sulphuric acid

C12H10O4S (250.03)


   

Pyridin-3-yl sulfate

3-Hydroxypyridine sulphuric acid(1-)

C5H4NO4S- (173.9861)


   

5-Hydroxytryptophol sulfate

3-(2-Hydroxyethyl)-1H-indol-5-yl sulphuric acid

C10H10NO5S- (256.028)