2.02012-07-30 14:55:22 -06002015-09-17 15:42:08 -0600ECMDB21344M2MDB001743MethanesulfonateMesylate esters are a group of organic compounds that share a common functional group with the general structure CH3SO2O-R, abbreviated MsO-R, where R is an organic substituent. Mesylate is considered an excellent leaving group in nucleophilic substitution reactions.Camostat mesilateCamostat mesilic acidCamostat mesylateCamostat mesylic acidCamostat monomethanesulfonateCamostat monomethanesulfonic acidCamostat monomethanesulphonateCamostat monomethanesulphonic acidMethanesulfonateMethanesulfonic acidMethanesulphonateMethanesulphonic acidMethylsulfonateMethylsulfonic acidMethylsulphonateMethylsulphonic acidMSACH3O3S95.0994.9808387114-{2-[(dimethylcarbamoyl)methoxy]-2-oxoethyl}phenyl 4-carbamimidamidobenzoatecamostat59721-29-8CS([O-])(=O)=OInChI=1S/CH4O3S/c1-5(2,3)4/h1H3,(H,2,3,4)/p-1AFVFQIVMOAPDHO-UHFFFAOYSA-MCytosolExtra-organismPeriplasmlogp1.88logs-3.80solubility6.26e-02 g/llogp1.51pka_strongest_acidic19.54pka_strongest_basic8.54iupac4-{2-[(dimethylcarbamoyl)methoxy]-2-oxoethyl}phenyl 4-carbamimidamidobenzoateaverage_mass95.09mono_mass94.980838711smilesCS([O-])(=O)=OformulaCH3O3SinchiInChI=1S/CH4O3S/c1-5(2,3)4/h1H3,(H,2,3,4)/p-1inchikeyAFVFQIVMOAPDHO-UHFFFAOYSA-Mpolar_surface_area134.81refractivity117.77polarizability41.93rotatable_bond_count9acceptor_count6donor_count3physiological_charge1formal_charge0sulfur metabolism (methanesulfonate)The sulfur metabolism pathway starts in three possible ways. The first is the uptake of sulfate through an active transport reaction via a sulfate transport system containing an ATP-binding protein which hydrolyses ATP. Sulfate is converted by the sulfate adenylyltransferase enzymatic complex to adenosine phosphosulfate through the addition of adenine from a molecule of ATP, along with one phosphate group. Adenosine phosphosulfate is further converted to phoaphoadenosine phosphosulfate through an ATP hydrolysis and dehydrogenation reaction by the adenylyl-sulfate kinase. Phoaphoadenosine phosphosulfate is finally dehydrogenated and converted to sulfite by phosphoadenosine phosphosulfate reductase. This reaction requires magnesium, and adenosine 3',5'-diphosphate is the bi-product. A thioredoxin is also oxidized. Sulfite can also be produced from the dehydrogenation of cyanide along with the conversion of thiosulfate to thiocyanate by the thiosulfate sulfurtransferase enzymatic complex. Sulfite next undergoes a series of reactions that lead to the production of pyruvic acid, which is a precursor for pathways such as gluconeogenesis. The first reaction in this series is the conversion of sulfite to hydrogen sulfide through hygrogenation and the deoxygenation of sulfite to form a water molecule. The reaction is catalyzed by the sulfite reductase [NADPH] flavoprotein alpha and beta components. Siroheme, 4Fe-4S, flavin mononucleotide, and FAD function as cofactors or prosthetic groups. Hydrogen sulfide next undergoes dehydrogenation in a reversible reaction to form L-Cysteine and acetic acid, via the cysteine synthase complex and the coenzyme pyridoxal 5'-phosphate. L-Cysteine is dehydrogenated and converted to 2-aminoacrylic acid (a bronsted acid) and hydrogen sulfide(which may be reused) by a larger enzymatic complex composed of cysteine synthase A/B, protein malY, cystathionine-β-lyase, and tryptophanase, along with the coenzyme pyridoxal 5'-phosphate. 2-aminoacrylic acid isomerizes to 2-iminopropanoate, which along with a water molecule and a hydrogen ion is lastly converted to pyruvic acid and ammonium in a spontaneous fashion. The second possible initial starting point for sulfur metabolism is the import of taurine(an alternate sulfur source) into the cytoplasm via the taurine ABC transporter complex. Taurine, oxoglutaric acid, and oxygen are converted to sulfite by the alpha-ketoglutarate-dependent taurine dioxygenase. Carbon dioxide, succinic acid, and aminoacetaldehyde are bi-products of this reaction. Sulfite next enters pyruvic acid synthesis as already described. The third variant of sulfur metabolism starts with the import of an alkyl sulfate, in this case methanesulfonate, into the cytoplasm via an aliphatic sulfonate ABC transporter complex which hydrolyses ATP. Methanesulfonate is dehydrogenated and along with oxygen is converted to sulfite and an aldehyde by the FMNH2-dependent alkanesulfonate monooxygenase enzyme. Water and flavin mononucleotide(which is used in a subsequent reaction as a prosthetic group) are also produced. Sulfite is next converted to pyruvic acid by the process already described.PW000927MetabolicSpecdb::CMs109195Specdb::CMs121924Specdb::MsMs33221Specdb::MsMs33222Specdb::MsMs33223Specdb::MsMs3421247Specdb::MsMs3421248Specdb::MsMs3421249Specdb::MsMs26663Specdb::MsMs26664Specdb::MsMs26665Specdb::MsMs3421244Specdb::MsMs3421245Specdb::MsMs342124652843602440C1114525224CPD-3746MethanesulfonateFMN reductaseP80644SSUE_ECOLIssuEhttp://ecmdb.ca/proteins/P80644.xmlAlkanesulfonate monooxygenaseP80645SSUD_ECOLIssuDhttp://ecmdb.ca/proteins/P80645.xmlPutative aliphatic sulfonates transport permease protein ssuCP75851SSUC_ECOLIssuChttp://ecmdb.ca/proteins/P75851.xmlPutative aliphatic sulfonates-binding proteinP75853SSUA_ECOLIssuAhttp://ecmdb.ca/proteins/P75853.xmlAliphatic sulfonates import ATP-binding protein SsuBP0AAI1SSUB_ECOLIssuBhttp://ecmdb.ca/proteins/P0AAI1.xmlPutative aliphatic sulfonates transport permease protein ssuCP75851SSUC_ECOLIssuChttp://ecmdb.ca/proteins/P75851.xmlPutative aliphatic sulfonates-binding proteinP75853SSUA_ECOLIssuAhttp://ecmdb.ca/proteins/P75853.xmlOuter membrane protein NP77747OMPN_ECOLIompNhttp://ecmdb.ca/proteins/P77747.xmlOuter membrane pore protein EP02932PHOE_ECOLIphoEhttp://ecmdb.ca/proteins/P02932.xmlOuter membrane protein FP02931OMPF_ECOLIompFhttp://ecmdb.ca/proteins/P02931.xmlAliphatic sulfonates import ATP-binding protein SsuBP0AAI1SSUB_ECOLIssuBhttp://ecmdb.ca/proteins/P0AAI1.xmlOuter membrane protein CP06996OMPC_ECOLIompChttp://ecmdb.ca/proteins/P06996.xmlAdenosine triphosphate + Water + Methanesulfonate > ADP + Hydrogen ion + Methanesulfonate + PhosphateAdenosine triphosphate + Water + Methanesulfonate > ADP + Hydrogen ion + Methanesulfonate + PhosphateFMNH + Methanesulfonate + Oxygen > Formaldehyde + Flavin Mononucleotide + Hydrogen ion + Water + SulfiteOxygen + methanesulfonate + FMNH2 + Methanesulfonate > Hydrogen ion + Water + Flavin Mononucleotide + Sulfite + Betaine aldehyde + SulfitePW_R003471Adenosine triphosphate + Water + methanesulfonate + Methanesulfonate > Adenosine diphosphate + Phosphate + Hydrogen ion + methanesulfonate + ADPPW_RCT000151