2.02012-07-30 14:54:57 -06002015-09-13 15:15:31 -0600ECMDB21208M2MDB001616Dimethyl sulfoxideDimethyl sulfoxide is a highly polar organic liquid, that is used widely as a chemical solvent. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect tissue during cryopreservation. Because of its high boiling point (189 (CH3)2SO(DMSO)(methanesulfinyl)methane(methanesulphinyl)methane(methylsulfinyl)methane(methylsulphinyl)methane1,1'-Sulfinylbis-Methane1,1'-Sulphinylbis-Methane<IMG SRC='/ncidb2/images/delta.gif' WIDTH=12 HEIGHT=14>NDeltanDemasorbDemavetDemesoDemsodroxDermasorbDiemthyl sulfoxideDiemthyl sulphoxideDimethyl sulfoxideDimethyl Sulfoxide (USAN)Dimethyl sulfoxide BPDimethyl sulfoxide(USAN)Dimethyl sulfoxixdeDimethyl sulfur oxideDimethyl sulphoxideDimethyl Sulphoxide (USAN)Dimethyl sulphoxide BPDimethyl sulphoxide(USAN)Dimethyl sulphoxixdeDimethyl sulphur oxideDimethyl sulpoxideDimethyli sulfoxidumDimethyli sulphoxidumDimethylsulfoxidDimethylsulfoxydeDimethylsulphoxidDimethylsulphoxydeDimetil sulfoxidoDimetil sulphoxidoDimexideDimexidumDipirartril-tropicoDMSODMSO (methyl sulfoxide)DMSO (methyl sulphoxide)DolicurDoligurDomosoDromisolDurasorbGamasol 90HerpidHyadurInfiltrinaKemsolMethyl sulfoxideMethyl sulphoxideMethylsulfinylmethaneMethylsulphinylmethanenRimso 50S(O)Me2SclerosolSomiprontSulfinylbis methaneSulfinylbis(methane)Sulfinylbis-MethaneSulfinylbismethaneSulfinyldimethaneSulfoxide, dimethylSulphinylbis methaneSulphinylbis(methane)Sulphinylbis-MethaneSulphinylbismethaneSulphinyldimethaneSulphoxide, dimethylSyntexanTopsymC2H6OS78.13378.013935504methanesulfinylmethanedimethyl sulfoxide67-68-5CS(C)=OInChI=1S/C2H6OS/c1-4(2)3/h1-2H3IAZDPXIOMUYVGZ-UHFFFAOYSA-NLiquidCytosolExtra-organismPeriplasmlogp-1.09logs-0.08solubility6.57e+01 g/lmelting_point18.5 oClogp-1.4pka_strongest_basic-8iupacmethanesulfinylmethaneaverage_mass78.133mono_mass78.013935504smilesCS(C)=OformulaC2H6OSinchiInChI=1S/C2H6OS/c1-4(2)3/h1-2H3inchikeyIAZDPXIOMUYVGZ-UHFFFAOYSA-Npolar_surface_area17.07refractivity20.73polarizability7.91rotatable_bond_count0acceptor_count1donor_count0physiological_charge0formal_charge0dimethyl sulfoxide electron transferThe pathway can start in various spots. First step in this case starts with NADH interacting with a menaquinone oxidoreductase resulting in the release of a NADH and a hydrogen Ion, at the same time in the inner membrane a menaquinone interacts with 2 electrons and 2 hydrogen ions thus releasing a menaquinol. This allows for 4 hydrogen ions to be transferred from the cytosol to the periplasmic space. The menaquinol then interacts with a dimethyl sulfoxide reductase resulting in the release of 2 hydrogen ion and 2 electrons. At the same time dimethyl sulfoxide and 2 hydrogen ions interact with the enzyme resulting in the release of a dimethyl sulfide and a water molecule, this reaction happening in the periplasmic space.
The second set of reactions starts with a hydrogen interacting with a menaquinone oxidoreductase resulting in the release of two electrons being released into the inner membrane which then react with with 2 hydrogen ion and a menaquinone to produce a menaquinol. This menaquinol then reacts with a trimethylamine N-oxide reductase following the same steps as mentioned before.
The third set of reactions starts with with formate interacting with a formate dehydrogenase-O resulting in a release of carbon dioxide and a hydrogen ion, this releases 2 electrons that interact with a menaquinone and two hydrogen ions. This releases a menaquinol which then reacts with a trimethylamine N-oxide reductase following the same steps as mentioned beforePW001892Metabolicformate to dimethyl sulfoxide electron transferPWY0-1356NADH to dimethyl sulfoxide electron transferPWY0-1348Specdb::CMs21347Specdb::CMs27183Specdb::CMs29010Specdb::CMs29427Specdb::CMs99753Specdb::CMs99754Specdb::CMs99755Specdb::CMs167609Specdb::EiMs115Specdb::NmrOneD2579Specdb::NmrOneD3275Specdb::NmrOneD109598Specdb::NmrOneD109599Specdb::NmrOneD109600Specdb::NmrOneD109601Specdb::NmrOneD109602Specdb::NmrOneD109603Specdb::NmrOneD109604Specdb::NmrOneD109605Specdb::NmrOneD109606Specdb::NmrOneD109607Specdb::NmrOneD109608Specdb::NmrOneD109609Specdb::NmrOneD109610Specdb::NmrOneD109611Specdb::NmrOneD109612Specdb::NmrOneD109613Specdb::NmrOneD109614Specdb::NmrOneD109615Specdb::NmrOneD109616Specdb::NmrOneD109617Specdb::MsMs28670Specdb::MsMs28671Specdb::MsMs28672Specdb::MsMs35228Specdb::MsMs35229Specdb::MsMs35230Specdb::MsMs2226688Specdb::MsMs2228018Specdb::MsMs2229128Specdb::MsMs2230345Specdb::MsMs2751352Specdb::MsMs2751353Specdb::MsMs2751354Specdb::MsMs2930322Specdb::MsMs2930323Specdb::MsMs2930324HMDB02151679659C1114328262DMSODMSDimethyl_sulfoxideKeseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590.21097882Engelke UF, Tangerman A, Willemsen MA, Moskau D, Loss S, Mudd SH, Wevers RA: Dimethyl sulfone in human cerebrospinal fluid and blood plasma confirmed by one-dimensional (1)H and two-dimensional (1)H-(13)C NMR. NMR Biomed. 2005 Aug;18(5):331-6.15996001Goeb, Andre. Dimethyl sulfoxide. Ger. Offen. (1976), 12 pp.http://hmdb.ca/system/metabolites/msds/000/001/734/original/HMDB02151.pdf?1358894130Probable anaerobic dimethyl sulfoxide reductase chain ynfGP0AAJ1YNFG_ECOLIynfGhttp://ecmdb.ca/proteins/P0AAJ1.xmlAnaerobic dimethyl sulfoxide reductase chain AP18775DMSA_ECOLIdmsAhttp://ecmdb.ca/proteins/P18775.xmlAnaerobic dimethyl sulfoxide reductase chain BP18776DMSB_ECOLIdmsBhttp://ecmdb.ca/proteins/P18776.xmlPutative dimethyl sulfoxide reductase chain ynfEP77374YNFE_ECOLIynfEhttp://ecmdb.ca/proteins/P77374.xmlProbable dimethyl sulfoxide reductase chain ynfFP77783YNFF_ECOLIynfFhttp://ecmdb.ca/proteins/P77783.xmlTrimethylamine-N-oxide reductase 2P46923TORZ_ECOLItorZhttp://ecmdb.ca/proteins/P46923.xmlCytochrome c-type protein torYP52005TORY_ECOLItorYhttp://ecmdb.ca/proteins/P52005.xmlAnaerobic dimethyl sulfoxide reductase chain CP18777DMSC_ECOLIdmsChttp://ecmdb.ca/proteins/P18777.xmlAnaerobic dimethyl sulfoxide reductase chain ynfHP76173YNFH_ECOLIynfHhttp://ecmdb.ca/proteins/P76173.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.xmlOuter membrane protein CP06996OMPC_ECOLIompChttp://ecmdb.ca/proteins/P06996.xmlDimethyl sulfoxide + Menaquinol 8 > Dimethyl sulfide + Water + Menaquinone 82-Demethylmenaquinol 8 + Dimethyl sulfoxide > 2-Demethylmenaquinone 8 + Dimethyl sulfide + WaterDimethyl sulfoxide + a menaquinol > Dimethyl sulfide + Water + a menaquinoneDIMESULFREDUCT-RXNDimethyl sulfide + Menaquinone + Water > Dimethyl sulfoxide + Menaquinol 6Menaquinol 8 + Dimethyl sulfoxide + 2 Hydrogen ion + 2 Electron > menaquinone-8 + Dimethyl sulfide + Water +2 Hydrogen ionPW_RCT000176