MetaCyc Compound: dimethyl sulfide

Synonyms: reduced dimethyl sulfoxide, dimethyl sulphide, dimethylsulphide, DMS, dimethylsulfide

Superclasses: an organosulfur compound

Flux of dimethylsulfide (DMS) from ocean surface waters is the predominant natural source of sulfur to the atmosphere [Howard06]. Much of the DMS in ocean water is the result of microbial conversion of dimethylsulfoniopropanoate to DMS.

DMS influences climate because it is oxidized in the troposphere to sulfuric and methanesulfonic acids, which attract water and promote cloud formation [Charlson87].

Chemical Formula: C2H6S

Molecular Weight: 62.129 Daltons

Monoisotopic Molecular Weight: 62.0190208826 Daltons

dimethyl sulfide compound structure


InChI: InChI=1S/C2H6S/c1-3-2/h1-2H3


Unification Links: CAS:75-18-3, ChEBI:17437, ChemSpider:1039, HMDB:HMDB02303, IAF1260:35409, KEGG:C00580, PubChem:1068

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 63.09673Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

dimethyl sulfide degradation I :
dimethyl sulfide + NADH + oxygen + H+ → methanethiol + formaldehyde + NAD+ + H2O

dimethyl sulfide degradation II (oxidation) :
dimethyl sulfide + NADPH + oxygen + H+ → dimethyl sulfoxide + NADP+ + H2O

dimethyl sulfide degradation III (oxidation) :
dimethyl sulfide + 2 an oxidized cytochrome c2 + H2O → dimethyl sulfoxide + 2 a reduced cytochrome c2 + 2 H+

folate transformations I :
a tetrahydrofolate + trimethyl sulfonium ← dimethyl sulfide + an N5-methyl-tetrahydrofolate + H+

Not in pathways:
dimethyl sulfide + S-adenosyl-L-methionine → S-adenosyl-L-homocysteine + trimethyl sulfonium

Reactions known to produce the compound:

dimethylsulfoniopropanoate degradation I (cleavage) , superpathway of dimethylsulfoniopropanoate degradation :
dimethylsulfoniopropanoate → dimethyl sulfide + acrylate + H+

dimethylsulfoniopropanoate degradation II (cleavage) :
dimethylsulfoniopropioyl-CoA + 2 H2O → dimethyl sulfide + 3-hydroxypropanoate + coenzyme A + 2 H+

formate to dimethyl sulfoxide electron transfer , hydrogen to dimethyl sulfoxide electron transfer , NADH to dimethyl sulfoxide electron transfer :
dimethyl sulfide[periplasm] + a menaquinone[inner membrane] + H2O[periplasm] ← dimethyl sulfoxide[periplasm] + a menaquinol[inner membrane]

Reactions known to both consume and produce the compound:

methanogenesis from dimethylsulfide :
dimethyl sulfide + a [Co(I) methanethiol-specific corrinoid protein] + H+ ↔ methanethiol + a [methyl-Co(III) methanethiol-specific corrinoid protein]

In Reactions of unknown directionality:

dimethyl sulfoxide degradation :
dimethyl sulfoxide + NADH + H+ = dimethyl sulfide + NAD+ + H2O

Not in pathways:
dimethylsulfoniopropanoate + H2O = dimethyl sulfide + 3-hydroxypropanoate + H+

In Redox half-reactions:
dimethyl sulfoxide[out] + 2 H+[out] + 2 e-[membrane]dimethyl sulfide[out] + H2O[out]


Charlson87: Charlson, RJ, Lovelock, JE, Andreae, MO, Warren, SG (1987). "Oceanic phytoplankton, atmospheric sulphur, cloud albedo and climate." Nature 326:655-661.

Howard06: Howard EC, Henriksen JR, Buchan A, Reisch CR, Burgmann H, Welsh R, Ye W, Gonzalez JM, Mace K, Joye SB, Kiene RP, Whitman WB, Moran MA (2006). "Bacterial taxa that limit sulfur flux from the ocean." Science 314(5799);649-52. PMID: 17068264

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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