2.0 2012-07-30 14:54:57 -0600 2015-09-13 15:15:31 -0600 ECMDB21208 M2MDB001616 Dimethyl sulfoxide Dimethyl 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)methane 1,1'-Sulfinylbis-Methane 1,1'-Sulphinylbis-Methane <IMG SRC='/ncidb2/images/delta.gif' WIDTH=12 HEIGHT=14>N Deltan Demasorb Demavet Demeso Demsodrox Dermasorb Diemthyl sulfoxide Diemthyl sulphoxide Dimethyl sulfoxide Dimethyl Sulfoxide (USAN) Dimethyl sulfoxide BP Dimethyl sulfoxide(USAN) Dimethyl sulfoxixde Dimethyl sulfur oxide Dimethyl sulphoxide Dimethyl Sulphoxide (USAN) Dimethyl sulphoxide BP Dimethyl sulphoxide(USAN) Dimethyl sulphoxixde Dimethyl sulphur oxide Dimethyl sulpoxide Dimethyli sulfoxidum Dimethyli sulphoxidum Dimethylsulfoxid Dimethylsulfoxyde Dimethylsulphoxid Dimethylsulphoxyde Dimetil sulfoxido Dimetil sulphoxido Dimexide Dimexidum Dipirartril-tropico DMSO DMSO (methyl sulfoxide) DMSO (methyl sulphoxide) Dolicur Doligur Domoso Dromisol Durasorb Gamasol 90 Herpid Hyadur Infiltrina Kemsol Methyl sulfoxide Methyl sulphoxide Methylsulfinylmethane Methylsulphinylmethane n Rimso 50 S(O)Me2 Sclerosol Somipront Sulfinylbis methane Sulfinylbis(methane) Sulfinylbis-Methane Sulfinylbismethane Sulfinyldimethane Sulfoxide, dimethyl Sulphinylbis methane Sulphinylbis(methane) Sulphinylbis-Methane Sulphinylbismethane Sulphinyldimethane Sulphoxide, dimethyl Syntexan Topsym C2H6OS 78.133 78.013935504 methanesulfinylmethane dimethyl sulfoxide 67-68-5 CS(C)=O InChI=1S/C2H6OS/c1-4(2)3/h1-2H3 IAZDPXIOMUYVGZ-UHFFFAOYSA-N Liquid Cytosol Extra-organism Periplasm logp -1.09 ALOGPS logs -0.08 ALOGPS solubility 6.57e+01 g/l ALOGPS melting_point 18.5 oC logp -1.4 ChemAxon pka_strongest_basic -8 ChemAxon iupac methanesulfinylmethane ChemAxon average_mass 78.133 ChemAxon mono_mass 78.013935504 ChemAxon smiles CS(C)=O ChemAxon formula C2H6OS ChemAxon inchi InChI=1S/C2H6OS/c1-4(2)3/h1-2H3 ChemAxon inchikey IAZDPXIOMUYVGZ-UHFFFAOYSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 20.73 ChemAxon polarizability 7.91 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon dimethyl sulfoxide electron transfer The 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 before PW001892 Metabolic formate to dimethyl sulfoxide electron transfer PWY0-1356 NADH to dimethyl sulfoxide electron transfer PWY0-1348 Specdb::CMs 21347 Specdb::CMs 27183 Specdb::CMs 29010 Specdb::CMs 29427 Specdb::CMs 99753 Specdb::CMs 99754 Specdb::CMs 99755 Specdb::CMs 167609 Specdb::EiMs 115 Specdb::NmrOneD 2579 Specdb::NmrOneD 3275 Specdb::NmrOneD 109598 Specdb::NmrOneD 109599 Specdb::NmrOneD 109600 Specdb::NmrOneD 109601 Specdb::NmrOneD 109602 Specdb::NmrOneD 109603 Specdb::NmrOneD 109604 Specdb::NmrOneD 109605 Specdb::NmrOneD 109606 Specdb::NmrOneD 109607 Specdb::NmrOneD 109608 Specdb::NmrOneD 109609 Specdb::NmrOneD 109610 Specdb::NmrOneD 109611 Specdb::NmrOneD 109612 Specdb::NmrOneD 109613 Specdb::NmrOneD 109614 Specdb::NmrOneD 109615 Specdb::NmrOneD 109616 Specdb::NmrOneD 109617 Specdb::MsMs 28670 Specdb::MsMs 28671 Specdb::MsMs 28672 Specdb::MsMs 35228 Specdb::MsMs 35229 Specdb::MsMs 35230 Specdb::MsMs 2226688 Specdb::MsMs 2228018 Specdb::MsMs 2229128 Specdb::MsMs 2230345 Specdb::MsMs 2751352 Specdb::MsMs 2751353 Specdb::MsMs 2751354 Specdb::MsMs 2930322 Specdb::MsMs 2930323 Specdb::MsMs 2930324 HMDB02151 679 659 C11143 28262 DMSO DMS Dimethyl_sulfoxide Keseler, 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. 21097882 Engelke 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. 15996001 Goeb, Andre. Dimethyl sulfoxide. Ger. Offen. (1976), 12 pp. http://hmdb.ca/system/metabolites/msds/000/001/734/original/HMDB02151.pdf?1358894130 Probable anaerobic dimethyl sulfoxide reductase chain ynfG P0AAJ1 YNFG_ECOLI ynfG http://ecmdb.ca/proteins/P0AAJ1.xml Anaerobic dimethyl sulfoxide reductase chain A P18775 DMSA_ECOLI dmsA http://ecmdb.ca/proteins/P18775.xml Anaerobic dimethyl sulfoxide reductase chain B P18776 DMSB_ECOLI dmsB http://ecmdb.ca/proteins/P18776.xml Putative dimethyl sulfoxide reductase chain ynfE P77374 YNFE_ECOLI ynfE http://ecmdb.ca/proteins/P77374.xml Probable dimethyl sulfoxide reductase chain ynfF P77783 YNFF_ECOLI ynfF http://ecmdb.ca/proteins/P77783.xml Trimethylamine-N-oxide reductase 2 P46923 TORZ_ECOLI torZ http://ecmdb.ca/proteins/P46923.xml Cytochrome c-type protein torY P52005 TORY_ECOLI torY http://ecmdb.ca/proteins/P52005.xml Anaerobic dimethyl sulfoxide reductase chain C P18777 DMSC_ECOLI dmsC http://ecmdb.ca/proteins/P18777.xml Anaerobic dimethyl sulfoxide reductase chain ynfH P76173 YNFH_ECOLI ynfH http://ecmdb.ca/proteins/P76173.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml Dimethyl sulfoxide + Menaquinol 8 > Dimethyl sulfide + Water + Menaquinone 8 2-Demethylmenaquinol 8 + Dimethyl sulfoxide > 2-Demethylmenaquinone 8 + Dimethyl sulfide + Water Dimethyl sulfoxide + a menaquinol > Dimethyl sulfide + Water + a menaquinone DIMESULFREDUCT-RXN Dimethyl sulfide + Menaquinone + Water > Dimethyl sulfoxide + Menaquinol 6 Menaquinol 8 + Dimethyl sulfoxide + 2 Hydrogen ion + 2 Electron > menaquinone-8 + Dimethyl sulfide + Water +2 Hydrogen ion PW_RCT000176