Showing Compound Card for Dimethylsulfide (CDB000595)

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Record Information
Version1.0
Created at2020-03-19 00:45:42 UTC
Updated at2020-12-07 19:07:33 UTC
CannabisDB IDCDB000595
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameDimethylsulfide
DescriptionDimethylsulfide, also known as methyl thioether or 2-thiapropane, 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. Dimethylsulfide is a sulfur containing organic chemical compound with a disagreeable odor. It is produced in its vapor form while cooking certain vegetables, notably corn, cabbage, and seafood. It is also an indication of bacterial infection in malt production and brewing. Dimethylsulfide is a breakdown product of dimethylsulfoniopropionate and is also produced by the bacterial metabolism of methanethiol. Dimethylsulfide flammable liquid with a boiling point of 37 °C. It can also be found as a microbial metabolite from bacteria from the genera Bradyrhizobium, Cyanothece, Escherichia, Pseudomonas and Rhizobiaceae (PMID: 25807229 ). Dimethylsulfide is the most abundant biological sulfur compound emitted to the atmosphere. Emission occurs over the oceans by phytoplankton. Dimethyl sulfide, dimethyl disulfide, and dimethyl trisulfide have been found among the volatiles given off by the fly-attracting plant known as dead-horse arum (Helicodiceros muscivorus). Dimethyl sulfide has also been detected in the volatile fraction of Cannabis sativa samples obtained from police seizures (PMID: 26657499 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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 Weight62.13
Monoisotopic Molecular Weight62.019
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point-98.3 °CNot Available
Boiling Point35 to 41 °CWikipedia
Water Solubility22 mg/mL at 25 °CNot Available
logP0.977Wikipedia
Predicted Properties
PropertyValueSource
logP0.59ALOGPS
logP1.22ChemAxon
logS-0.53ALOGPS
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-01ot-9000000000-3da3b740e54dd0695ac82015-03-01View Spectrum
GC-MSDimethylsulfide, non-derivatized, GC-MS Spectrumsplash10-01ot-9000000000-8ed5810ef2a492b40ae1Spectrum
GC-MSDimethylsulfide, non-derivatized, GC-MS Spectrumsplash10-01ot-9000000000-aab0fb854ed08a99a142Spectrum
GC-MSDimethylsulfide, non-derivatized, GC-MS Spectrumsplash10-01ot-9000000000-b8e506cefc1462c55765Spectrum
GC-MSDimethylsulfide, non-derivatized, GC-MS Spectrumsplash10-01ot-9000000000-8ed5810ef2a492b40ae1Spectrum
GC-MSDimethylsulfide, non-derivatized, GC-MS Spectrumsplash10-01ot-9000000000-aab0fb854ed08a99a142Spectrum
GC-MSDimethylsulfide, non-derivatized, GC-MS Spectrumsplash10-01ot-9000000000-b8e506cefc1462c55765Spectrum
Predicted GC-MSDimethylsulfide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03dj-9000000000-452048d3bfa7a40636c4Spectrum
Predicted GC-MSDimethylsulfide, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-01ot-9000000000-8ed5810ef2a492b40ae12012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-01ot-9000000000-360d47e40fcfcf205bf32012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-01ot-9000000000-b8e506cefc1462c557652012-08-31View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-9000000000-ae1ff184cb043d43cd3a2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9000000000-189f32d3eb2bb107bad12015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9000000000-5579d822eaf64cbda3b32015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-9000000000-45a7990a4b612cb726642015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-9000000000-3bb7835f1011f708503e2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ox-9000000000-d5b5c0545e3e2ec5e98e2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-9000000000-6fc9e9a3cbf6090ab8d52021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-9000000000-6fc9e9a3cbf6090ab8d52021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-9000000000-6fc9e9a3cbf6090ab8d52021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-9000000000-f865abc3930f083f5ea22021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9000000000-f865abc3930f083f5ea22021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-9000000000-efaeb46b008ef59dd3de2021-09-22View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, cyclohexane, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Indolethylamine N-methyltransferaseINMT7p14.3O95050 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0002303
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
References
General References
  1. Carrion O, Curson ARJ, 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 ]
  2. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]

Enzymes

Enzyme Details
1. Indolethylamine N-methyltransferase
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