dimethyl sulfide (CHEBI:17437)

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CHEBI:17437 - dimethyl sulfide

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ChEBI Name	dimethyl sulfide

ChEBI ID	CHEBI:17437

Definition	A methyl sulfide in which the sulfur atom is substituted by two methyl groups. It is produced naturally by some marine algae.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:44169, CHEBI:4611, CHEBI:14168, CHEBI:14175, CHEBI:23800

Supplier Information	ChemicalBook:CB6478393, eMolecules:493755

Download	Molfile XML SDF

more structures >>

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Marvin 10310723083D

9 8 0 0 0 0 999 V2000

-0.9279 -0.6348 -0.7912 C 0 0 0 0 0 0 0 0 0 0 0 0

0.7467 -0.9156 -0.1777 S 0 0 0 0 0 0 0 0 0 0 0 0

0.9583 0.5976 0.7840 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.2199 -1.4830 -1.4106 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.9648 0.2711 -1.3973 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.6288 -0.5494 0.0397 H 0 0 0 0 0 0 0 0 0 0 0 0

1.9498 0.5879 1.2368 H 0 0 0 0 0 0 0 0 0 0 0 0

0.2112 0.6529 1.5766 H 0 0 0 0 0 0 0 0 0 0 0 0

0.8754 1.4733 0.1397 H 0 0 0 0 0 0 0 0 0 0 0 0

2 1 1 0 0 0 0

3 2 1 0 0 0 0

1 4 1 0 0 0 0

1 5 1 0 0 0 0

1 6 1 0 0 0 0

3 7 1 0 0 0 0

3 8 1 0 0 0 0

3 9 1 0 0 0 0

M END): 16 ms

reading 9 atoms

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Wikipedia	License
Dimethyl sulfide (DMS) or methylthiomethane is an organosulfur compound with the formula (CH3)2S. It is the simplest thioether and has a characteristic disagreeable odor. It is a flammable liquid that boils at 37 °C (99 °F). It is a component of the smell produced from cooking of certain vegetables (notably maize, cabbage, and beetroot) and seafoods. It is also an indication of bacterial contamination in malt production and brewing. It is a breakdown product of dimethylsulfoniopropionate (DMSP), and is also produced by the bacterial metabolism of methanethiol.
Read full article at Wikipedia

Formula

C2H6S

Net Charge

Average Mass

62.13504

Monoisotopic Mass

62.01902

InChI

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

InChIKey

QMMFVYPAHWMCMS-UHFFFAOYSA-N

SMILES

CSC

Metabolite of Species	Details
Escherichia coli (NCBI:txid562)	See: PubMed

Roles Classification
Biological Role(s):	Escherichia coli metabolite Any bacterial metabolite produced during a metabolic reaction in Escherichia coli. marine metabolite Any metabolite produced during a metabolic reaction in marine macro- and microorganisms. bacterial xenobiotic metabolite Any bacterial metabolite produced by metabolism of a xenobiotic compound in bacteria. algal metabolite Any eukaryotic metabolite produced during a metabolic reaction in algae including unicellular organisms like chlorella and diatoms to multicellular organisms like giant kelps and brown algae. EC 3.5.1.4 (amidase) inhibitor An EC 3.5.1.* (non-peptide linear amide C-N hydrolase) inhibitor that interferes with the action of amidase (EC 3.5.1.4).

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	dimethyl sulfide (CHEBI:17437) has role Escherichia coli metabolite (CHEBI:76971) dimethyl sulfide (CHEBI:17437) has role algal metabolite (CHEBI:84735) dimethyl sulfide (CHEBI:17437) has role bacterial xenobiotic metabolite (CHEBI:76976) dimethyl sulfide (CHEBI:17437) has role EC 3.5.1.4 (amidase) inhibitor (CHEBI:77941) dimethyl sulfide (CHEBI:17437) has role marine metabolite (CHEBI:76507) dimethyl sulfide (CHEBI:17437) is a aliphatic sulfide (CHEBI:22327)

Incoming	sulfanediylbis(methylene) group (CHEBI:46972) is substituent group from dimethyl sulfide (CHEBI:17437)

IUPAC Name

(methylsulfanyl)methane

Synonyms

Sources

(METHYLSULFANYL)METHANE

PDBeChem

2-thiapropane

ChemIDplus Indicates when synonyms have been adapted from the specified source i.e. not exact copies.

[SMe₂]

MolBase

Dimethyl sulfide

KEGG COMPOUND

dimethyl sulfide

UniProt

dimethyl sulphide

NIST Chemistry WebBook Indicates when synonyms have been adapted from the specified source i.e. not exact copies.

DMS

Note: (2015-03-23) Ambiguous - has also been used to mean dimethyl sulfate and dimercaptosuccinic acid.

ChemIDplus

Methyl sulfide

KEGG COMPOUND

Methyl thioether

KEGG COMPOUND

Manual Xrefs	Databases
1888	MolBase
C00580	KEGG COMPOUND
c0237	UM-BBD
CPD-7670	MetaCyc
Dimethyl_sulfide	Wikipedia
HMDB0002303	HMDB
MSM	PDBeChem
View more database links

Registry Numbers	Types	Sources
1696847	Reaxys Registry Number	Reaxys
75-18-3	CAS Registry Number	KEGG COMPOUND
75-18-3	CAS Registry Number	NIST Chemistry WebBook
75-18-3	CAS Registry Number	ChemIDplus

Citations

Rinnan R, Steinke M, McGenity T, Loreto F (2014)
Plant volatiles in extreme terrestrial and marine environments.
Plant, cell & environment 37, 1776-1789 [PubMed:24601952]
[show Abstract]

Savoca MS, Nevitt GA (2014)
Evidence that dimethyl sulfide facilitates a tritrophic mutualism between marine primary producers and top predators.
Proceedings of the National Academy of Sciences of the United States of America 111, 4157-4161 [PubMed:24591607]
[show Abstract]

Tangerman A (2009)
Measurement and biological significance of the volatile sulfur compounds hydrogen sulfide, methanethiol and dimethyl sulfide in various biological matrices.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 877, 3366-3377 [PubMed:19505855]
[show Abstract]

Makhongela HS, Glowacka AE, Agarkar VB, Sewell BT, Weber B, Cameron RA, Cowan DA, Burton SG (2007)
A novel thermostable nitrilase superfamily amidase from Geobacillus pallidus showing acyl transfer activity.
Applied microbiology and biotechnology 75, 801-811 [PubMed:17347819]
[show Abstract]
An amidase (EC 3.5.1.4) in branch 2 of the nitrilase superfamily, from the thermophilic strain Geobacillus pallidus RAPc8, was produced at high expression levels (20 U/mg) in small-scale fermentations of Escherichia coli. The enzyme was purified to 90% homogeneity with specific activity of 1,800 U/mg in just two steps, namely, heat-treatment and gel permeation chromatography. Sodium dodecyl sulfate-polyacrylamide gel electrophoresis (SDS-PAGE) and electron microscopic (EM) analysis of the homogenous enzyme showed the native enzyme to be a homohexamer of 38 kDa subunits. Analysis of the biochemical properties of the amidase showed that the optimal temperature and pH for activity were 50 and 7.0 degrees C, respectively. The amidase exhibited high thermal stability at 50 and 60 degrees C, with half-lives greater than 5 h at both temperatures. At 70 and 80 degrees C, the half-life values were 43 and 10 min, respectively. The amidase catalyzed the hydrolysis of low molecular weight aliphatic amides, with D: -selectivity towards lactamide. Inhibition studies showed activation/inhibition data consistent with the presence of a catalytically active thiol group. Acyl transfer reactions were demonstrated with acetamide, propionamide, isobutyramide, and acrylamide as substrates and hydroxylamine as the acyl acceptor; the highest reaction rate being with isobutyramide. Immobilization by entrapment in polyacrylamide gels, covalent binding on Eupergit C beads at 4 degrees C and on Amberlite-XAD57 resulted in low protein binding and low activity, but immobilization on Eupergit C beads at 25 degrees C with cross-linking resulted in high protein binding yield and high immobilized specific activity (80% of non-immobilized activity). Characterization of Eupergit C-immobilized preparations showed that the optimum reaction temperature was unchanged, the pH range was somewhat broadened, and stability was enhanced giving half-lives of 52 min at 70 degrees C and 30 min at 80 degrees C. The amidase has potential for application under high temperature conditions as a biocatalyst for D: -selective amide hydrolysis producing enantiomerically pure carboxylic acids and for production of novel amides by acyl transfer.

Last Modified

25 January 2016

CHEBI:17437 - dimethyl sulfide

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