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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:47 UTC
Update Date2021-10-13 04:38:43 UTC
HMDB IDHMDB0002303
Secondary Accession Numbers
  • HMDB02303
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. Dimethylsulfide in concentrated liquid form is insoluble and a flammable. This is a microbial metabolite that can be found in Bradyrhizobium, Cyanothece, Escherichia, Pseudomonas and Rhizobiaceae (PMID:25807229 ).
Structure
Data?1582752242
Synonyms
ValueSource
(METHYLsulfanyl)methaneChEBI
2-ThiapropaneChEBI
[SMe2]ChEBI
Dimethyl sulphideChEBI
DMSChEBI
Methyl sulfideChEBI
Methyl thioetherChEBI
(METHYLsulphanyl)methaneGenerator
Dimethyl sulfideGenerator
Methyl sulphideGenerator
DimethylsulphideGenerator
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 KeyQMMFVYPAHWMCMS-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-98.3 °CNot Available
Boiling Point37.30 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility22 mg/mL at 25 °CNot Available
LogP0.977 (est)The Good Scents Company Information System
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility18.5 g/LALOGPS
logP10(0.59) g/LALOGPS
logP10(1.22) g/LChemAxon
logS10(-0.53) g/LALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity18.89 m³·mol⁻¹ChemAxon
Polarizability7.24 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+110.46531661259
DarkChem[M-H]-103.94631661259

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Dimethylsulfide EI-B (Non-derivatized)splash10-01ot-9000000000-8ed5810ef2a492b40ae12017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Dimethylsulfide EI-B (Non-derivatized)splash10-01ot-9000000000-aab0fb854ed08a99a1422017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Dimethylsulfide EI-B (Non-derivatized)splash10-01ot-9000000000-b8e506cefc1462c557652017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Dimethylsulfide EI-B (Non-derivatized)splash10-01ot-9000000000-8ed5810ef2a492b40ae12018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Dimethylsulfide EI-B (Non-derivatized)splash10-01ot-9000000000-aab0fb854ed08a99a1422018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Dimethylsulfide EI-B (Non-derivatized)splash10-01ot-9000000000-b8e506cefc1462c557652018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dimethylsulfide GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dj-9000000000-452048d3bfa7a40636c42016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dimethylsulfide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-01ot-9000000000-3da3b740e54dd0695ac82015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Dimethylsulfide EI-B (HITACHI RMU-7M) , Positive-QTOFsplash10-01ot-9000000000-8ed5810ef2a492b40ae12012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dimethylsulfide EI-B (HITACHI M-80) , Positive-QTOFsplash10-01ot-9000000000-360d47e40fcfcf205bf32012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dimethylsulfide EI-B (HITACHI M-80B) , Positive-QTOFsplash10-01ot-9000000000-b8e506cefc1462c557652012-08-31HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylsulfide 10V, Positive-QTOFsplash10-03di-9000000000-ae1ff184cb043d43cd3a2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylsulfide 20V, Positive-QTOFsplash10-03di-9000000000-189f32d3eb2bb107bad12015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylsulfide 40V, Positive-QTOFsplash10-0002-9000000000-5579d822eaf64cbda3b32015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylsulfide 10V, Negative-QTOFsplash10-03di-9000000000-45a7990a4b612cb726642015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylsulfide 20V, Negative-QTOFsplash10-01ox-9000000000-3bb7835f1011f708503e2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylsulfide 40V, Negative-QTOFsplash10-01ox-9000000000-d5b5c0545e3e2ec5e98e2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylsulfide 10V, Negative-QTOFsplash10-03di-9000000000-6fc9e9a3cbf6090ab8d52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylsulfide 20V, Negative-QTOFsplash10-03di-9000000000-6fc9e9a3cbf6090ab8d52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylsulfide 40V, Negative-QTOFsplash10-03di-9000000000-6fc9e9a3cbf6090ab8d52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylsulfide 10V, Positive-QTOFsplash10-03di-9000000000-f865abc3930f083f5ea22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylsulfide 20V, Positive-QTOFsplash10-03di-9000000000-f865abc3930f083f5ea22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dimethylsulfide 40V, Positive-QTOFsplash10-03di-9000000000-efaeb46b008ef59dd3de2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue Locations
  • Adipose Tissue
  • Intestine
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0 - 1.0 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified649.135 nmol/g wet fecesAdult (>18 years old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified343.344 nmol/g wet fecesAdult (>18 years old)Not Specified
Normal
details
FecesDetected and Quantified563.299 nmol/g wet fecesAdult (>18 years old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified3224.8 +/- 403.1 uMAdult (>18 years old)Male
Dimethyl sulfide poisoning
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Clostridium difficile infection
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative Colitis
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Crohn's disease
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>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. [PubMed:1874893 ]
Ulcerative colitis
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
  2. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Crohn's disease
  1. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003591
KNApSAcK IDC00053130
Chemspider ID1039
KEGG Compound IDC00580
BioCyc IDCPD-7670
BiGG IDNot Available
Wikipedia LinkDimethyl_sulfide
METLIN ID6603
PubChem Compound1068
PDB IDNot Available
ChEBI ID17437
Food Biomarker OntologyNot Available
VMH IDDMS
MarkerDB IDNot Available
Good Scents IDrw1022341
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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:14628896 ]
  8. Carrion O, Curson AR, Kumaresan D, Fu Y, Lang AS, Mercade E, Todd JD: A novel pathway producing dimethylsulphide in bacteria is widespread in soil environments. Nat Commun. 2015 Mar 25;6:6579. doi: 10.1038/ncomms7579. [PubMed:25807229 ]

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