2.0 2012-07-30 14:54:56 -0600 2015-06-03 17:20:53 -0600 ECMDB21207 M2MDB001615 Dimethyl sulfide Dimethyl sulfide (DMS) or methylthiomethane is an organosulfur compound with the formula (CH3)2S. Dimethyl sulfide is a water-insoluble flammable liquid that boils at 37 (methylsulfanyl)methane (methylsulphanyl)methane 1,1'-Thiobis-Methane 2-Thiapropane 2-Thiopropane Dimethyl monosulfide Dimethyl monosulphide Dimethyl sulfide Dimethyl sulfide (natural) Dimethyl sulfide [UN1164] [Flammable liquid] Dimethyl sulfoxide(Reduced) Dimethyl sulphide Dimethyl sulphide (natural) Dimethyl sulphide [UN1164] [Flammable liquid] Dimethyl sulphoxide(Reduced) Dimethyl thioether Dimethylsulfid Dimethylsulfide Dimethylsulphid Dimethylsulphide DMS Exact-S Methanethiomethane Methyl monosulfide Methyl monosulphide Methyl sulfide Methyl sulphide Methyl thioether Methyl-Sulfide Methyl-Sulphide Methylthiomethane Methylthiomethyl radical MSM Reduced dimethyl sulfoxide Reduced dimethyl sulphoxide Reduced-dmso Sulfure de methyle Sulphure de methyle Thiobis-Methane Thiobismethane Thiopropane [SMe2] C2H6S 62.134 62.019020882 (methylsulfanyl)methane dimethyl sulfide 75-18-3 CSC InChI=1S/C2H6S/c1-3-2/h1-2H3 QMMFVYPAHWMCMS-UHFFFAOYSA-N Liquid Cytosol Extra-organism Periplasm logp 0.59 ALOGPS logs -0.53 ALOGPS solubility 1.85e+01 g/l ALOGPS melting_point -98.3 oC logp 1.22 ChemAxon iupac (methylsulfanyl)methane ChemAxon average_mass 62.134 ChemAxon mono_mass 62.019020882 ChemAxon smiles CSC ChemAxon formula C2H6S ChemAxon inchi InChI=1S/C2H6S/c1-3-2/h1-2H3 ChemAxon inchikey QMMFVYPAHWMCMS-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 18.89 ChemAxon polarizability 7.24 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Sulfur metabolism 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 into the cytoplasm via an aliphatic sulfonate ABC transporter complex which hydrolyses ATP. The alkyl sulfate 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. PW000922 ec00920 Metabolic 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 3182 Specdb::CMs 27927 Specdb::CMs 27994 Specdb::CMs 29278 Specdb::CMs 99764 Specdb::CMs 99765 Specdb::CMs 99766 Specdb::CMs 169166 Specdb::EiMs 1845 Specdb::NmrOneD 1871 Specdb::NmrOneD 3971 Specdb::NmrOneD 4254 Specdb::NmrOneD 116098 Specdb::NmrOneD 116099 Specdb::NmrOneD 116100 Specdb::NmrOneD 116101 Specdb::NmrOneD 116102 Specdb::NmrOneD 116103 Specdb::NmrOneD 116104 Specdb::NmrOneD 116105 Specdb::NmrOneD 116106 Specdb::NmrOneD 116107 Specdb::NmrOneD 116108 Specdb::NmrOneD 116109 Specdb::NmrOneD 116110 Specdb::NmrOneD 116111 Specdb::NmrOneD 116112 Specdb::NmrOneD 116113 Specdb::NmrOneD 116114 Specdb::NmrOneD 116115 Specdb::NmrOneD 116116 Specdb::NmrOneD 116117 Specdb::MsMs 6343 Specdb::MsMs 6344 Specdb::MsMs 6345 Specdb::MsMs 8024 Specdb::MsMs 8025 Specdb::MsMs 8026 Specdb::MsMs 14696 Specdb::MsMs 14697 Specdb::MsMs 14698 Specdb::MsMs 2459911 Specdb::MsMs 2459912 Specdb::MsMs 2459913 Specdb::MsMs 2476154 Specdb::MsMs 2476155 Specdb::MsMs 2476156 HMDB02303 1068 1039 C00580 17437 CPD-7670 MSM Dimethyl_sulfide 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 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 Jiang T, Suarez FL, Levitt MD, Nelson SE, Ziegler EE: Gas production by feces of infants. 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Oral Dis. 2003 Sep;9(5):273-6. 14628896 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 Menaquinone + Water + Dimethyl sulfide <> Menaquinol 6 R09501 Menaquinol 8 + Dimethyl sulfoxide + 2 Hydrogen ion + 2 Electron > menaquinone-8 + Dimethyl sulfide + Water +2 Hydrogen ion PW_RCT000176