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Showing metabocard for Dimethyl sulfone (HMDB0004983)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-09-13 08:28:37 UTC
Update Date2023-02-21 17:17:05 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 has the general structure RS(=O)2R' (R,R' =alkyl, aryl), attached to two carbon atoms. Dimethyl sulfone (DMSO2) 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. 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 sulfurous tasting compound. dimethyl sulfone is found on average in the highest concentration in 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. It occurs naturally in some primitive plants and is present in small amounts in many foods and beverages. Dimethyl sulfone can be found in plasma and CSF of normal humans.
Structure
Data?1676999825
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0004983 (Dimethyl sulfone)


  Mrv1652303202019002D          

  5  4  0  0  0  0            999 V2000
   15.6007  -12.0678    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.3152  -11.6553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0131  -12.7823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8862  -12.4803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1882  -11.3534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  1  5  1  0  0  0  0
M  END
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3D MOL for HMDB0004983 (Dimethyl sulfone)

HMDB0004983
     RDKit          3D
Dimethyl sulfone
 11 10  0  0  0  0  0  0  0  0999 V2000
    1.4185    0.3212   -0.2323 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0132   -0.3103    0.6572 S   0  0  0  0  0  6  0  0  0  0  0  0
   -1.4239    0.0000   -0.3327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1301    0.3478    2.0027 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1833   -1.7918    0.9090 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7515   -0.5056   -0.9100 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1038    1.2140   -0.8397 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2452    0.5829    0.4285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2312    0.8332   -1.0239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3200    0.2319    0.2684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6101   -0.9232   -0.9272 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  2  5  2  0
  1  6  1  0
  1  7  1  0
  1  8  1  0
  3  9  1  0
  3 10  1  0
  3 11  1  0
M  END
Download

3D SDF for HMDB0004983 (Dimethyl sulfone)


  Mrv1652303202019002D          

  5  4  0  0  0  0            999 V2000
   15.6007  -12.0678    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.3152  -11.6553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0131  -12.7823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8862  -12.4803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1882  -11.3534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  1  5  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004983

> <DATABASE_NAME>
hmdb

> <SMILES>
CS(C)(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C2H6O2S/c1-5(2,3)4/h1-2H3

> <INCHI_KEY>
HHVIBTZHLRERCL-UHFFFAOYSA-N

> <FORMULA>
C2H6O2S

> <MOLECULAR_WEIGHT>
94.133

> <EXACT_MASS>
94.008850126

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
8.602570349100972

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methanesulfonylmethane

> <ALOGPS_LOGP>
-0.95

> <JCHEM_LOGP>
-1.3009717433333332

> <ALOGPS_LOGS>
-0.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
20.533

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.58e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methylsulfonylmethane

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0004983 (Dimethyl sulfone)

HMDB0004983
     RDKit          3D
Dimethyl sulfone
 11 10  0  0  0  0  0  0  0  0999 V2000
    1.4185    0.3212   -0.2323 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0132   -0.3103    0.6572 S   0  0  0  0  0  6  0  0  0  0  0  0
   -1.4239    0.0000   -0.3327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1301    0.3478    2.0027 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1833   -1.7918    0.9090 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7515   -0.5056   -0.9100 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1038    1.2140   -0.8397 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2452    0.5829    0.4285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2312    0.8332   -1.0239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3200    0.2319    0.2684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6101   -0.9232   -0.9272 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  2  5  2  0
  1  6  1  0
  1  7  1  0
  1  8  1  0
  3  9  1  0
  3 10  1  0
  3 11  1  0
M  END
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PDB for HMDB0004983 (Dimethyl sulfone)

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  S   UNK     0      29.121 -22.527   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0      30.455 -21.757   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      29.891 -23.860   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      27.788 -23.297   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      28.351 -21.193   0.000  0.00  0.00           C+0
CONECT    1    2    3    4    5                                             
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5    1                                                            
MASTER        0    0    0    0    0    0    0    0    5    0    8    0
END
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3D PDB for HMDB0004983 (Dimethyl sulfone)

COMPND    HMDB0004983
HETATM    1  C1  UNL     1       1.418   0.321  -0.232  1.00  0.00           C  
HETATM    2  S1  UNL     1       0.013  -0.310   0.657  1.00  0.00           S  
HETATM    3  C2  UNL     1      -1.424   0.000  -0.333  1.00  0.00           C  
HETATM    4  O1  UNL     1      -0.130   0.348   2.003  1.00  0.00           O  
HETATM    5  O2  UNL     1       0.183  -1.792   0.909  1.00  0.00           O  
HETATM    6  H1  UNL     1       1.752  -0.506  -0.910  1.00  0.00           H  
HETATM    7  H2  UNL     1       1.104   1.214  -0.840  1.00  0.00           H  
HETATM    8  H3  UNL     1       2.245   0.583   0.429  1.00  0.00           H  
HETATM    9  H4  UNL     1      -1.231   0.833  -1.024  1.00  0.00           H  
HETATM   10  H5  UNL     1      -2.320   0.232   0.268  1.00  0.00           H  
HETATM   11  H6  UNL     1      -1.610  -0.923  -0.927  1.00  0.00           H  
CONECT    1    2    6    7    8
CONECT    2    3    4    4    5
CONECT    2    5
CONECT    3    9   10   11
END
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SMILES for HMDB0004983 (Dimethyl sulfone)

CS(C)(=O)=O
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INCHI for HMDB0004983 (Dimethyl sulfone)

InChI=1S/C2H6O2S/c1-5(2,3)4/h1-2H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
Dimethyl sulphoneChEBI
MethylsulfonylmethaneChEBI
SulfonylbismethaneChEBI
SulphonylbismethaneChEBI
MethylsulphonylmethaneGenerator
Dimethyl sulfone, 13C-labeledMeSH
Methyl sulfoneMeSH
Methyl sulfonmethaneMeSH
(Methylsulfonyl)methaneHMDB
DimethylsulfoneHMDB
Lignisul MSMHMDB
Opti MSMHMDB
Sulfonylbis-methaneHMDB
Dimethyl sulfoneChEBI
SulphonyldimethaneGenerator, HMDB
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
Physiological effectNot Available
Disposition
Source
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point109 °CNot Available
Boiling Point237.00 to 239.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1000000 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-1.41HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+117.22531661259
DarkChem[M-H]-109.63131661259
DeepCCS[M+H]+126.78530932474
DeepCCS[M-H]-123.98830932474
DeepCCS[M-2H]-160.41930932474
DeepCCS[M+Na]+134.91130932474
AllCCS[M+H]+126.932859911
AllCCS[M+H-H2O]+122.732859911
AllCCS[M+NH4]+130.832859911
AllCCS[M+Na]+132.032859911
AllCCS[M-H]-134.732859911
AllCCS[M+Na-2H]-140.532859911
AllCCS[M+HCOO]-146.832859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Predicted by Siyang on May 30, 202212.183 minutes33406817
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1519.0 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid468.5 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid169.2 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid341.6 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid184.8 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid379.3 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid460.1 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)402.5 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid897.7 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid276.3 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1185.0 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid314.5 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid406.9 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate692.9 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA346.3 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water192.9 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Dimethyl sulfoneCS(C)(=O)=O1841.6Standard polar33892256
Dimethyl sulfoneCS(C)(=O)=O799.3Standard non polar33892256
Dimethyl sulfoneCS(C)(=O)=O917.1Semi standard non polar33892256
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Urine
Tissue Locations
  • Brain
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified8.8 +/- 7.3 uMAdult (>18 years old)Not SpecifiedNormal details
BloodDetected and Quantified1.5-16.1 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified11.3 +/- 6.2 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified2.0 +/- 1.0 uMAdult (>18 years old)BothNormal details
SalivaDetected and Quantified13.53 +/- 5.14 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
 details
UrineDetected and Quantified4.6 (2.5-7.5) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
 details
UrineDetected and Quantified8.0 (1.3-49.0) umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified11.371 +/- 7.16 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
BloodDetected and Quantified37.5 - 42.5 uMAdult (>18 years old)Both
Methionine adenosyltransferase (MAT) I/III deficiency		 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
    • Analysis of 30 no...
 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. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
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
MarkerDB IDMDB00000464
Good Scents IDrw1260371
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. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]