2.02015-06-19 06:38:42 -06002021-02-22 17:12:33 -0700ECMDB23904M2MDB005861Aryl sulfatePhenol sulphate, also known as phenylsulfate or aryl sulphate, belongs to the class of organic compounds known as phenylsulfates. Phenylsulfates are compounds containing a sulfate group conjugated to a phenyl group. In normal humans, phenol sulphate is primarily a gut-derived metabolite that arises from the activity of the bacterial enzyme tyrosine phenol-lyase, which is responsible for the synthesis of phenol from dietary tyrosine (PMID: 31015435). Phenol sulphate can also arise from the consumption of phenol or from phenol poisoning (PMID: 473790). Phenol sulphate is produced from the conjugation of phenol with sulphate in the liver. In particular, phenol sulphate can be biosynthesized from phenol and phosphoadenosine phosphosulfate through the action of the enzyme sulfotransferase 1A1 in the liver. Phenol sulphate can be found in most mammals (mice, rats, sheep, dogs, humans) and likely most animals. Phenol sulphate is a uremic toxin (PMID: 30068866). It is a protein-bound uremic solute that induces reactive oxygen species (ROS) production and decreases glutathione levels, rendering cells vulnerable to oxidative stress (PMID: 29474405). In experimental models of diabetes, phenol sulphate administration has been shown to induce albuminuria and podocyte damage. In a diabetic patient cohort, phenol sulphate levels were found to significantly correlate with basal and predicted 2-year progression of albuminuria in patients with microalbuminuria (PMID: 31015435). Aryl sulfuric acidAryl sulphateAryl sulphuric acidPhenol sulfatePhenol sulfuric acidPhenol sulphatePhenol sulphuric acidC6H6O4S174.174173.99867937phenyloxidanesulfonic acidphenylsulfateOS(=O)(=O)OC1=CC=CC=C1InChI=1S/C6H6O4S/c7-11(8,9)10-6-4-2-1-3-5-6/h1-5H,(H,7,8,9)CTYRPMDGLDAWRQ-UHFFFAOYSA-Nlogp-0.75logs-1.69solubility3.57e+00 g/llogp1.19pka_strongest_acidic-2.2iupacphenyloxidanesulfonic acidaverage_mass174.174mono_mass173.99867937smilesOS(=O)(=O)OC1=CC=CC=C1formulaC6H6O4SinchiInChI=1S/C6H6O4S/c7-11(8,9)10-6-4-2-1-3-5-6/h1-5H,(H,7,8,9)inchikeyCTYRPMDGLDAWRQ-UHFFFAOYSA-Npolar_surface_area63.6refractivity38.03polarizability15.03rotatable_bond_count2acceptor_count3donor_count1physiological_charge-1formal_charge0Sphingolipid metabolismec00600Steroid hormone biosynthesisec00140Specdb::CMs36780Specdb::CMs148372Specdb::NmrOneD55522Specdb::NmrOneD55523Specdb::NmrOneD55524Specdb::NmrOneD55525Specdb::NmrOneD55526Specdb::NmrOneD55527Specdb::NmrOneD55528Specdb::NmrOneD55529Specdb::NmrOneD55530Specdb::NmrOneD55531Specdb::NmrOneD55532Specdb::NmrOneD55533Specdb::NmrOneD55534Specdb::NmrOneD55535Specdb::NmrOneD55536Specdb::NmrOneD55537Specdb::NmrOneD55538Specdb::NmrOneD55539Specdb::NmrOneD55540Specdb::NmrOneD55541Specdb::MsMs23354Specdb::MsMs23355Specdb::MsMs23356Specdb::MsMs30152Specdb::MsMs30153Specdb::MsMs30154Specdb::MsMs2256668Specdb::MsMs2257906Specdb::MsMs3224269Specdb::MsMs3224270Specdb::MsMs3224271Specdb::MsMs3225226Specdb::MsMs3225227Specdb::MsMs3225228C00850Aryl sulfate + Water <> Phenol + SulfateR01243