Human Metabolome Database Version 3.5

Showing metabocard for Dimethyl sulfone (HMDB04983)

Record Information
Version 3.5
Creation Date 2006-09-13 02:28:37 -0600
Update Date 2013-05-29 13:41:26 -0600
HMDB ID HMDB04983
Secondary Accession Numbers
  • HMDB06702
Metabolite Identification
Common Name Dimethyl sulfone
Description Dimethyl sulfone (DMSO2) or methylsulfonylmethane (MSM), is an organic sulfur compound belonging to a class of chemicals known as sulfones. It occurs naturally in some primitive plants and is present in small amounts in many foods and beverages. DMSO2 reflects its close chemical relationship to dimethyl sulfoxide (DMSO), which differs only in the oxidation state of the sulfur atom. DMSO2 is the primary metabolite of DMSO in humans, and it shares some of the properties of DMSO. Dimethyl sulfone is a metabolite occurring in plasma and CSF of normal human. It derives from dietary sources, from intestinal bacterial metabolism and from human endogenous methanethiol metabolism. (PMID 15996001 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (methylsulfonyl)methane
  2. Dimethyl sulfone
  3. Dimethyl sulphone
  4. Dimethylsulfone
  5. Lignisul MSM
  6. Methyl sulfone
  7. Methylsulfonylmethane
  8. Opti MSM
  9. Sulfonylbis-methane
  10. Sulfonylbismethane
  11. Sulphonylbismethane
Chemical Formula C2H6O2S
Average Molecular Weight 94.133
Monoisotopic Molecular Weight 94.008850126
IUPAC Name methanesulfonylmethane
Traditional IUPAC Name methylsulfonylmethane
CAS Registry Number 67-71-0
SMILES CS(C)(=O)=O
InChI Identifier InChI=1S/C2H6O2S/c1-5(2,3)4/h1-2H3
InChI Key HHVIBTZHLRERCL-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aliphatic Acyclic Compounds
Class Sulfonyls
Sub Class N/A
Other Descriptors
  • Organic Compounds
  • Sulfones
  • a sulfone(Cyc)
  • sulfone(ChEBI)
Substituents
  • Sulfoxide
Direct Parent Sulfonyls
Ontology
Status Detected and Quantified
Origin
  • Drug metabolite
  • Endogenous
  • Microbial
Biofunction
  • Osmolyte, enzyme cofactor, signalling
  • Waste products
Application Not Available
Cellular locations
  • Cytoplasm
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 109 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP -1.41 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
LogP -0.95 ALOGPS
LogP -1.3 ChemAxon
LogS -0.23 ALOGPS
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 0 ChemAxon
Polar Surface Area 34.14 A2 ChemAxon
Rotatable Bond Count 0 ChemAxon
Refractivity 20.53 ChemAxon
Polarizability 8.6 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Kidney
  • Liver
  • Brain
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
8.8 +/- 7.3 uM Adult (>18 years old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
2.0 +/- 1.0 uM Not Specified Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
11.3 +/- 6.2 uM Adult (>18 years old) Not Specified Normal
Urine Detected and Quantified
8.0 (1.3-49.0) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
4.6 (2.5-7.5) umol/mmol creatinine Adult (>18 years old) Both Normal
  • Geigy Scient...
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Cerebrospinal Fluid (CSF) Detected and Quantified 574.0 (0.0-1148.0) uM Adult (>18 years old) Both Comment Dimethyl sulfone supplementation
Associated Disorders and Diseases
Disease References
Dimethyl sulfone supplementation
  • 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 Link_out
      Associated OMIM IDs None
      DrugBank ID Not Available
      DrugBank Metabolite ID DBMET00570 Link_out
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB006725
      KNApSAcK ID Not Available
      Chemspider ID 5978 Link_out
      KEGG Compound ID C11142 Link_out
      BioCyc ID Not Available
      BiGG ID Not Available
      Wikipedia Link Methylsulfonylmethane Link_out
      NuGOwiki Link HMDB04983 Link_out
      Metagene Link HMDB04983 Link_out
      METLIN ID 7236 Link_out
      PubChem Compound 6213 Link_out
      PDB ID Not Available
      ChEBI ID 9349 Link_out
      References
      Synthesis Reference Douglas, Thomas B. Heats of formation of liquid methyl suffoxide and crystalline methyl sulfone at 18° Journal of the American Chemical Society (1946), 68 1072-6.
      Material Safety Data Sheet (MSDS) Download (PDF)
      General References
      1. Rogovin JL: Accumulation of methylsulfonylmethane in the human brain: identification by multinuclear magnetic resonance spectroscopy. Toxicol Lett. 2002 Mar 28;129(3):263; author reply 265. Pubmed: 11888710 Link_out
      2. Rose SE, Chalk JB, Galloway GJ, Doddrell DM: Detection of dimethyl sulfone in the human brain by in vivo proton magnetic resonance spectroscopy. Magn Reson Imaging. 2000 Jan;18(1):95-8. Pubmed: 10642107 Link_out
      3. Lin A, Nguy CH, Shic F, Ross BD: Accumulation of methylsulfonylmethane in the human brain: identification by multinuclear magnetic resonance spectroscopy. Toxicol Lett. 2001 Sep 15;123(2-3):169-77. Pubmed: 11641045 Link_out
      4. 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 Link_out