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Record Information
Version3.6
Creation Date2006-05-22 14:17:47 UTC
Update Date2016-02-11 01:05:33 UTC
HMDB IDHMDB02303
Secondary Accession NumbersNone
Metabolite Identification
Common NameDimethylsulfide
DescriptionDimethylsulfide is the predominant volatile sulfur compound (VSC) in breadth malodor, a metabolite of suplatast tosilate (a dimethylsulphonium compound for the treatment of asthma) in patients that regularly take that medication. (PMID 14628896 ). Dimethylsulfide is a sulfur containing organic chemical compound with a disagreeable odor. In vapor form it is produced by cooking of certain vegetables, notably corn and cabbage, and seafood. It is also an indication of bacterial infection in malt production and brewing. It is a breakdown product of dimethylsulfoniopropionate, and is also produced by the bacterial metabolism of methanethiol. Dimethyl sulfide in concentrated liquid form is insoluble and a flammable.-- Wikipedia.
Structure
Thumb
Synonyms
ValueSource
(METHYLsulfanyl)methaneChEBI
2-ThiapropaneChEBI
[SMe2]ChEBI
Dimethyl sulphideChEBI
DMSChEBI
Methyl sulfideChEBI
Methyl thioetherChEBI
(METHYLsulphanyl)methaneGenerator
MethylsulphanylmethaneGenerator
Dimethyl sulfideGenerator
Methyl sulphideGenerator
Dimethyl sulfoxide(reduced)HMDB
MethylthiomethaneHMDB
2-ThiopropaneHMDB
Dimethyl monosulfideHMDB
Dimethyl sulfide (natural)HMDB
Dimethyl thioetherHMDB
DimethylsulfidHMDB
MethanethiomethaneHMDB
Methyl monosulfideHMDB
Methylthiomethyl radicalHMDB
MSMHMDB
Reduced-dmsoHMDB
Thiobis-methaneHMDB
ThiopropaneHMDB
Chemical FormulaC2H6S
Average Molecular Weight62.134
Monoisotopic Molecular Weight62.019020882
IUPAC Name(methylsulfanyl)methane
Traditional Namedimethyl sulfide
CAS Registry Number75-18-3
SMILES
CSC
InChI Identifier
InChI=1S/C2H6S/c1-3-2/h1-2H3
InChI KeyInChIKey=QMMFVYPAHWMCMS-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as dialkylthioethers. These are organosulfur compounds containing a thioether group that is substituted by two alkyl groups.
KingdomOrganic compounds
Super ClassOrganosulfur compounds
ClassThioethers
Sub ClassDialkylthioethers
Direct ParentDialkylthioethers
Alternative Parents
Substituents
  • Dialkylthioether
  • Sulfenyl compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Drug metabolite
  • Endogenous
  • Microbial
Biofunction
  • Osmolyte, enzyme cofactor, signalling
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-98.3 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility22 mg/mL at 25 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility18.5 mg/mLALOGPS
logP0.59ALOGPS
logP1.22ChemAxon
logS-0.53ALOGPS
pKa (Strongest Basic)-9.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity18.89 m3·mol-1ChemAxon
Polarizability7.24 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-01ot-9000000000-8ed5810ef2a492b40ae1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-01ot-9000000000-360d47e40fcfcf205bf3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-01ot-9000000000-b8e506cefc1462c55765View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-9000000000-ae1ff184cb043d43cd3aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9000000000-189f32d3eb2bb107bad1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9000000000-5579d822eaf64cbda3b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-9000000000-45a7990a4b612cb72664View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-9000000000-3bb7835f1011f708503eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ox-9000000000-d5b5c0545e3e2ec5e98eView in MoNA
MSMass Spectrum (Electron Ionization)splash10-01ot-9000000000-3da3b740e54dd0695ac8View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue Location
  • Adipose Tissue
  • Intestine
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0 - 1.0 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified3224.8 +/- 403.1 uMAdult (>18 years old)Male
Dimethyl sulfide poisoning
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Clostridium difficile infection
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Ulcerative Colitis
details
Associated Disorders and Diseases
Disease References
Dimethyl sulfide poisoning
  1. Terazawa K, Kaji H, Akabane H, Takatori T: Determination of dimethyl sulphide in blood and adipose tissue by headspace gas analysis. J Chromatogr. 1991 Apr 19;565(1-2):453-6. [1874893 ]
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00551
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB003591
KNApSAcK IDNot Available
Chemspider ID1039
KEGG Compound IDC00580
BioCyc IDREDUCED-DMSO
BiGG IDNot Available
Wikipedia LinkDimethylsulfide
NuGOwiki LinkHMDB02303
Metagene LinkHMDB02303
METLIN ID6603
PubChem Compound1068
PDB IDMSM
ChEBI ID17437
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Rosen RT, Hiserodt RD, Fukuda EK, Ruiz RJ, Zhou Z, Lech J, Rosen SL, Hartman TG: The determination of metabolites of garlic preparations in breath and human plasma. Biofactors. 2000;13(1-4):241-9. [11237188 ]
  2. 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 ]
  3. Yeung CK, Lang DH, Thummel KE, Rettie AE: Immunoquantitation of FMO1 in human liver, kidney, and intestine. Drug Metab Dispos. 2000 Sep;28(9):1107-11. [10950857 ]
  4. Terazawa K, Kaji H, Akabane H, Takatori T: Determination of dimethyl sulphide in blood and adipose tissue by headspace gas analysis. J Chromatogr. 1991 Apr 19;565(1-2):453-6. [1874893 ]
  5. Jiang T, Suarez FL, Levitt MD, Nelson SE, Ziegler EE: Gas production by feces of infants. J Pediatr Gastroenterol Nutr. 2001 May;32(5):534-41. [11429513 ]
  6. Gahl WA, Ingelfinger J, Mohan P, Bernardini I, Hyman PE, Tangerman A: Intravenous cysteamine therapy for nephropathic cystinosis. Pediatr Res. 1995 Oct;38(4):579-84. [8559613 ]
  7. Murata T, Fujiyama Y, Yamaga T, Miyazaki H: Breath malodor in an asthmatic patient caused by side-effects of medication: a case report and review of the literature. Oral Dis. 2003 Sep;9(5):273-6. [14628896 ]

Enzymes

General function:
Involved in methyltransferase activity
Specific function:
Functions as thioether S-methyltransferase and is active with a variety of thioethers and the corresponding selenium and tellurium compounds, including 3-methylthiopropionaldehyde, dimethyl selenide, dimethyl telluride, 2-methylthioethylamine, 2-methylthioethanol, methyl-n-propyl sulfide and diethyl sulfide. Plays an important role in the detoxification of selenium compounds (By similarity). Catalyzes the N-methylation of tryptamine and structurally related compounds.
Gene Name:
INMT
Uniprot ID:
O95050
Molecular weight:
28833.695
Reactions
S-Adenosylmethionine + Dimethylsulfide → S-Adenosylhomocysteine + Trimethyl sulfoniumdetails