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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:55:32 UTC
Update Date2019-07-23 06:12:49 UTC
HMDB IDHMDB0033212
Secondary Accession Numbers
  • HMDB33212
Metabolite Identification
Common NameDimethyl selenide
DescriptionDimethyl selenide, also known as selenobismethane or (CH3)2Se, belongs to the class of organic compounds known as selenoethers. These are organic compounds containing a selenoether group, with the general formula RseR' ( where R, R' are not H atoms). Dimethyl selenide is a drug. Dimethyl selenide is possibly neutral. Outside of the human body, Dimethyl selenide has been detected, but not quantified in, several different foods, such as breadnut tree seeds, almonds, globe artichokes, cashew nuts, and green vegetables. This could make dimethyl selenide a potential biomarker for the consumption of these foods. An organoselenium compound of two methyl groups covalently bound to a selenium.
Structure
Data?1563862369
Synonyms
ValueSource
(CH3)2SeChEBI
DimethylseleniumChEBI
Methyl selenideChEBI
Methyl seleniumChEBI
Selenium dimethylChEBI
SelenobismethaneChEBI
(Methylselanyl)methaneHMDB
Dimethyl-selenideHMDB
DimethylselenideHMDB
Methane, selenobis- (9ci)HMDB
Methyl selenide (8ci)HMDB
Methyl selenide, 8ciHMDB
Selenobis-methaneHMDB
Selenobismethane, 9ciHMDB
DMe-selenideHMDB
Dimethylselenide, 75Se-labeledHMDB
Chemical FormulaC2H6Se
Average Molecular Weight109.03
Monoisotopic Molecular Weight109.96347202
IUPAC Name(methylselanyl)methane
Traditional Namedimethylselenide
CAS Registry Number593-79-3
SMILES
C[Se]C
InChI Identifier
InChI=1S/C2H6Se/c1-3-2/h1-2H3
InChI KeyRVIXKDRPFPUUOO-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as selenoethers. These are organic compounds containing a selenoether group, with the general formula RseR' ( where R, R' are not H atoms).
KingdomOrganic compounds
Super ClassOrganometallic compounds
ClassOrganometalloid compounds
Sub ClassOrganoselenium compounds
Direct ParentSelenoethers
Alternative Parents
Substituents
  • Selenoether
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-87.2 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility24.4 mg/mL at 25 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility71 g/LALOGPS
logP0.09ALOGPS
logP0.63ChemAxon
logS-0.19ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity24.21 m³·mol⁻¹ChemAxon
Polarizability6.68 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-5900000000-717b45f25e8f72124e71Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-f33023a1a99a7f5816adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-52f4296a65752e430fceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0900000000-a3cb6690b98976ee60daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4l-8900000000-3b964e17a5bd7ef922c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1900000000-dd3e52051b2f8b997e36Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1900000000-18c7fa02391df77a4a07Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDBMET01462
Phenol Explorer Compound IDNot Available
FooDB IDFDB011225
KNApSAcK IDC00033776
Chemspider ID11158
KEGG Compound IDC02535
BioCyc IDCPD-12005
BiGG IDNot Available
Wikipedia LinkDimethyl selenide
METLIN IDNot Available
PubChem Compound11648
PDB IDNot Available
ChEBI ID4610
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Gabel-Jensen C, Lunoe K, Gammelgaard B: Formation of methylselenol, dimethylselenide and dimethyldiselenide in in vitro metabolism models determined by headspace GC-MS. Metallomics. 2010 Feb;2(2):167-73. doi: 10.1039/b914255j. Epub 2010 Jan 7. [PubMed:21069149 ]
  2. Sovova K, Shestivska V, Spanel P: Real-time quantification of traces of biogenic volatile selenium compounds in humid air by selected ion flow tube mass spectrometry. Anal Chem. 2012 Jun 5;84(11):4979-83. doi: 10.1021/ac300609m. Epub 2012 May 18. [PubMed:22548680 ]
  3. Ghasemi E, Farahani H: Head space solid phase microextraction based on nano-structured lead dioxide: application to the speciation of volatile organoselenium in environmental and biological samples. J Chromatogr A. 2012 Oct 5;1258:16-20. doi: 10.1016/j.chroma.2012.08.027. Epub 2012 Aug 15. [PubMed:22939459 ]
  4. Krittaphol W, Wescombe PA, Thomson CD, McDowell A, Tagg JR, Fawcett JP: Metabolism of L-selenomethionine and selenite by probiotic bacteria: in vitro and in vivo studies. Biol Trace Elem Res. 2011 Dec;144(1-3):1358-69. doi: 10.1007/s12011-011-9057-2. Epub 2011 Apr 15. [PubMed:21494803 ]
  5. Ghasemi E, Sillanpaa M, Najafi NM: Headspace hollow fiber protected liquid-phase microextraction combined with gas chromatography-mass spectroscopy for speciation and determination of volatile organic compounds of selenium in environmental and biological samples. J Chromatogr A. 2011 Jan 21;1218(3):380-6. doi: 10.1016/j.chroma.2010.12.005. Epub 2010 Dec 9. [PubMed:21185031 ]
  6. Ip C, Ganther HE: Activity of methylated forms of selenium in cancer prevention. Cancer Res. 1990 Feb 15;50(4):1206-11. [PubMed:2105164 ]
  7. Bayse CA, Antony S: Modeling the oxidation of ebselen and other organoselenium compounds using explicit solvent networks. J Phys Chem A. 2009 May 14;113(19):5780-5. doi: 10.1021/jp901880n. [PubMed:19374403 ]
  8. Winkel L, Feldmann J, Meharg AA: Quantitative and qualitative trapping of volatile methylated selenium species entrained through nitric acid. Environ Sci Technol. 2010 Jan 1;44(1):382-7. doi: 10.1021/es902345m. [PubMed:19950978 ]
  9. Goenaga-Infante H, Kassam S, Stokes E, Hopley C, Joel SP: Capabilities of HPLC with APEX-Q nebulisation ICP-MS and ESI MS/MS to compare selenium uptake and speciation of non-malignant with different B cell lymphoma lines. Anal Bioanal Chem. 2011 Feb;399(5):1789-97. doi: 10.1007/s00216-010-4474-1. Epub 2010 Dec 8. [PubMed:21140135 ]
  10. Bueno M, Pannier F: Quantitative analysis of volatile selenium metabolites in normal urine by headspace solid phase microextraction gas chromatography-inductively coupled plasma mass spectrometry. Talanta. 2009 May 15;78(3):759-63. doi: 10.1016/j.talanta.2008.12.044. Epub 2008 Dec 30. [PubMed:19269425 ]
  11. Tsopelas F, Tsantili-Kakoulidou A, Ochsenkuhn-Petropoulou M: Exploring the elution mechanism of selenium species on liquid chromatography. J Sep Sci. 2011 Feb;34(4):376-84. doi: 10.1002/jssc.201000771. Epub 2011 Jan 24. [PubMed:21259435 ]
  12. Ohta Y, Kobayashi Y, Konishi S, Hirano S: Speciation analysis of selenium metabolites in urine and breath by HPLC- and GC-inductively coupled plasma-MS after administration of selenomethionine and methylselenocysteine to rats. Chem Res Toxicol. 2009 Nov;22(11):1795-801. doi: 10.1021/tx900202m. [PubMed:19715347 ]
  13. Campillo N, Penalver R, Hernandez-Cordoba M: Determination of dimethylselenide and dimethyldiselenide in milk and milk by-products by solid-phase microextraction and gas chromatography with atomic emission detection. Talanta. 2010 Mar 15;80(5):1856-61. doi: 10.1016/j.talanta.2009.10.034. Epub 2009 Oct 24. [PubMed:20152423 ]
  14. Krittaphol W, McDowell A, Thomson CD, Mikov M, Fawcett JP: Biotransformation of L-selenomethionine and selenite in rat gut contents. Biol Trace Elem Res. 2011 Feb;139(2):188-96. doi: 10.1007/s12011-010-8653-x. Epub 2010 Mar 13. [PubMed:20229173 ]
  15. Kagami T, Narita T, Kuroda M, Notaguchi E, Yamashita M, Sei K, Soda S, Ike M: Effective selenium volatilization under aerobic conditions and recovery from the aqueous phase by Pseudomonas stutzeri NT-I. Water Res. 2013 Mar 1;47(3):1361-8. doi: 10.1016/j.watres.2012.12.001. Epub 2012 Dec 12. [PubMed:23270669 ]
  16. Magos L, Tandon SK, Webb M, Snowden R: The effects of treatment with selenite before and after the administration of [75Se]selenite on the exhalation of [75Se]dimethylselenide. Toxicol Lett. 1987 Apr;36(2):167-72. [PubMed:3576647 ]
  17. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

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 + Dimethyl selenide → S-Adenosylhomocysteine + Trimethylselenoniumdetails