Np mrd loader

Showing NP-Card for Dimethyl sulfone (NP0000414)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version1.0
Created at2006-09-13 08:28:37 UTC
Updated at2022-04-04 18:34:16 UTC
NP-MRD IDNP0000414
Secondary Accession NumbersNone
Natural Product 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
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000414 (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
Download

3D MOL for NP0000414 (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 NP0000414 (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>
NP0000414

> <DATABASE_NAME>
NP-MRD

> <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 NP0000414 (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

PDB for NP0000414 (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
Download

3D PDB for NP0000414 (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
Download

SMILES for NP0000414 (Dimethyl sulfone)

CS(C)(=O)=O
Download

INCHI for NP0000414 (Dimethyl sulfone)

InChI=1S/C2H6O2S/c1-5(2,3)4/h1-2H3
Download
View in JSmol
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 Mass94.1330 Da
Monoisotopic Mass94.00885 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-04-04View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, experimental)Ahselim2022-04-04View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, simulated)Varshavi.d262021-08-23View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Varshavi.d262021-08-23View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, simulated)Varshavi.d262021-07-31View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Varshavi.d262021-07-31View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, simulated)Varshavi.d262021-07-31View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Varshavi.d262021-07-31View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, simulated)Varshavi.d262021-07-31View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Varshavi.d262021-07-31View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, simulated)Varshavi.d262021-07-31View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Varshavi.d262021-07-31View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Cannabis sativaCannabisDB
      Not Available
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Psidium guajavaFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
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
Physical Properties
StateSolid
Experimental 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 CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (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
HMDB IDHMDB0004983
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
Good Scents IDrw1260371
References
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 ]
  5. Toso B, Procida G, Stefanon B: Determination of volatile compounds in cows' milk using headspace GC-MS. J Dairy Res. 2002 Nov;69(4):569-77. doi: 10.1017/s0022029902005782. [PubMed:12463694 ]
  6. Kowalska K, Habrowska-Gorczynska DE, Kurczewska D, Dominska K, Urbanek KA, Piastowska-Ciesielska AW: Methylsulfonylmethane sensitizes endometrial cancer cells to doxorubicin. Cell Biol Toxicol. 2021 Apr;37(2):261-275. doi: 10.1007/s10565-020-09542-4. Epub 2020 Jun 20. [PubMed:32562081 ]