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Showing metabocard for Dimethyl sulfone (HMDB0004983)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-09-13 08:28:37 UTC
Update Date2020-05-28 23:12:08 UTC
HMDB IDHMDB0004983
Secondary Accession Numbers
  • HMDB0006702
  • HMDB04983
  • HMDB06702
Metabolite Identification
Common NameDimethyl sulfone
DescriptionDimethyl sulfone, also known as sulfonylbismethane or lignisul MSM, belongs to the class of organic compounds known as sulfones. Sulfones are compounds containing a sulfonyl group( which as the general structure RS(=O)2R' (R,R' =alkyl, aryl)) attached to two carbon atoms. DMSO2 reflects its close chemical relationship to dimethyl sulfoxide (DMSO), which differs only in the oxidation state of the sulfur atom. Dimethyl sulfone is possibly neutral. Dimethyl sulfone exists in all living organisms, ranging from bacteria to humans. DMSO2 is the primary metabolite of DMSO in humans, and it shares some of the properties of DMSO. Dimethyl sulfone is a burnt and sulfurous tasting compound. Outside of the human body, Dimethyl sulfone is found, on average, in the highest concentration within milk (cow). Dimethyl sulfone has also been detected, but not quantified in, asparagus and guava. This could make dimethyl sulfone a potential biomarker for the consumption of these foods. Dimethyl sulfone can be found in Afipia (Wikipedia ). It occurs naturally in some primitive plants and is present in small amounts in many foods and beverages. Dimethyl sulfone (DMSO2) or Dimethyl sulfone (MSM), is an organic sulfur compound belonging to a class of chemicals known as sulfones. It derives from dietary sources, from intestinal bacterial metabolism and from human endogenous methanethiol metabolism. Dimethyl sulfone is a metabolite occurring in plasma and CSF of normal human.
Structure
Data?1582752337
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Dimethyl sulphoneChEBI
MethylsulfonylmethaneChEBI
SulfonylbismethaneChEBI
SulphonylbismethaneChEBI
MethylsulphonylmethaneGenerator
(Methylsulfonyl)methaneHMDB
DimethylsulfoneHMDB
Lignisul MSMHMDB
Methyl sulfoneHMDB
Opti MSMHMDB
Sulfonylbis-methaneHMDB
Methyl sulfonmethaneHMDB
Dimethyl sulfone, 13C-labeledHMDB
SulphonyldimethaneHMDB
Dimethyl sulfoneChEBI
Chemical FormulaC2H6O2S
Average Molecular Weight94.133
Monoisotopic Molecular Weight94.008850126
IUPAC Namemethanesulfonylmethane
Traditional Namemethylsulfonylmethane
CAS Registry Number67-71-0
SMILES
CS(C)(=O)=O
InChI Identifier
InChI=1S/C2H6O2S/c1-5(2,3)4/h1-2H3
InChI KeyHHVIBTZHLRERCL-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as sulfones. Sulfones are compounds containing a sulfonyl group( which as the general structure RS(=O)2R' (R,R' =alkyl, aryl)) attached to two carbon atoms.
KingdomOrganic compounds
Super ClassOrganosulfur compounds
ClassSulfonyls
Sub ClassSulfones
Direct ParentSulfones
Alternative Parents
Substituents
  • Sulfone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point109 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-1.41HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility55.8 g/LALOGPS
logP-0.95ALOGPS
logP-1.3ChemAxon
logS-0.23ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity20.53 m³·mol⁻¹ChemAxon
Polarizability8.6 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, Positivesplash10-002f-9000000000-3e72edc8bd8e168298a0Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0002-9000000000-9896ec507f104ada81f3Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014i-9000000000-aad0ad2e46e9a93df295Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9000000000-8cb5ee5ae152833c1e84Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-fb26633c75e592809868Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-3a6db80e12370ab204a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002b-9000000000-c5c35fbdd4193d0ece0dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-c0a7fe921fa7e601fb70Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-113ab821ffdae95a6086Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00fu-9000000000-2ef5cb880f6a43bd9df3Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Urine
Tissue Locations
  • Brain
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.5-16.1 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified8.8 +/- 7.3 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified2.0 +/- 1.0 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified11.3 +/- 6.2 uMAdult (>18 years old)Not SpecifiedNormal details
SalivaDetected and Quantified13.53 +/- 5.14 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
 details
UrineDetected and Quantified8.0 (1.3-49.0) umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified4.6 (2.5-7.5) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
 details
UrineDetected and Quantified11.371 +/- 7.16 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified37.5 - 42.5 uMAdult (>18 years old)Both
Methionine adenosyltransferase (MAT) I/III deficiency		 details
BloodDetected and Quantified5.06 (3.56) uMAdult (>18 years old)FemalePregnancy with fetus having congenital heart defect details
BloodDetected and Quantified4.78 (2.73) uMAdult (>18 years old)FemalePregnancy details
Cerebrospinal Fluid (CSF)Detected and Quantified574.0 uMAdult (>18 years old)Both
Methionine adenosyltransferase (MAT) I/III deficiency		 details
UrineDetected and Quantified10.047 +/- 14.963 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
 details
Associated Disorders and Diseases
Disease References
Pregnancy
  1. Bahado-Singh RO, Ertl R, Mandal R, Bjorndahl TC, Syngelaki A, Han B, Dong E, Liu PB, Alpay-Savasan Z, Wishart DS, Nicolaides KH: Metabolomic prediction of fetal congenital heart defect in the first trimester. Am J Obstet Gynecol. 2014 Sep;211(3):240.e1-240.e14. doi: 10.1016/j.ajog.2014.03.056. Epub 2014 Apr 1. [PubMed:24704061 ]
Methionine adenosyltransferase deficiency
  1. 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 ]
Eosinophilic esophagitis
  1. (). Mordechai, Hien, and David S. Wishart. .
Associated OMIM IDs
  • 250850 (Methionine adenosyltransferase deficiency)
  • 610247 (Eosinophilic esophagitis)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB006725
KNApSAcK IDNot Available
Chemspider ID5978
KEGG Compound IDC11142
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethylsulfonylmethane
METLIN ID7236
PubChem Compound6213
PDB IDNot Available
ChEBI ID9349
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceDouglas, 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 ]
  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 ]
  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 ]
  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 ]