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Showing NP-Card for Dimethylsulfide (NP0001419)

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Record Information
Version1.0
Created at2006-05-22 14:17:47 UTC
Updated at2021-08-19 23:59:07 UTC
NP-MRD IDNP0001419
Secondary Accession NumbersNone
Natural Product Identification
Common NameDimethylsulfide
DescriptionDimethylsulfide is the predominant volatile sulfur compound (VSC) in breadth malodor, a metabolite of suplatast tosilate (a dimethylsulphonium compound for the treatment of asthma) in patients that regularly take that medication. (PMID 14628896 ). Dimethylsulfide is a sulfur containing organic chemical compound with a disagreeable odor. In vapor form it is produced by cooking of certain vegetables, notably corn and cabbage, and seafood. It is also an indication of bacterial infection in malt production and brewing. It is a breakdown product of dimethylsulfoniopropionate, and is also produced by the bacterial metabolism of methanethiol. Dimethylsulfide in concentrated liquid form is insoluble and a flammable. This is a microbial metabolite that can be found in Bradyrhizobium, Cyanothece, Escherichia, Pseudomonas and Rhizobiaceae (PMID: 25807229 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001419 (Dimethylsulfide)

1068
  Mrv1652303202019012D          

  3  2  0  0  0  0            999 V2000
    2.3642   -0.2063    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6497    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
M  END
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3D MOL for NP0001419 (Dimethylsulfide)

HMDB0002303
     RDKit          3D
Dimethylsulfide
  9  8  0  0  0  0  0  0  0  0999 V2000
    1.4611    0.0485    0.1513 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0918   -0.8033   -0.6715 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4585   -0.0128   -0.1686 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4385   -0.2574    1.2211 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4420    1.1371    0.0139 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4019   -0.4200   -0.2573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7536    0.6758   -0.9787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2279   -0.8329   -0.1348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3952    0.4650    0.8247 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  1  4  1  0
  1  5  1  0
  1  6  1  0
  3  7  1  0
  3  8  1  0
  3  9  1  0
M  END
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3D SDF for NP0001419 (Dimethylsulfide)

1068
  Mrv1652303202019012D          

  3  2  0  0  0  0            999 V2000
    2.3642   -0.2063    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.0786    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6497    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001419

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CSC

> <INCHI_IDENTIFIER>
InChI=1S/C2H6S/c1-3-2/h1-2H3

> <INCHI_KEY>
QMMFVYPAHWMCMS-UHFFFAOYSA-N

> <FORMULA>
C2H6S

> <MOLECULAR_WEIGHT>
62.134

> <EXACT_MASS>
62.019020882

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
7.236348155286841

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(methylsulfanyl)methane

> <ALOGPS_LOGP>
0.59

> <JCHEM_LOGP>
1.2235795016666668

> <ALOGPS_LOGS>
-0.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
18.8917

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.85e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dimethyl sulfide

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0001419 (Dimethylsulfide)

HMDB0002303
     RDKit          3D
Dimethylsulfide
  9  8  0  0  0  0  0  0  0  0999 V2000
    1.4611    0.0485    0.1513 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0918   -0.8033   -0.6715 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4585   -0.0128   -0.1686 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4385   -0.2574    1.2211 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4420    1.1371    0.0139 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4019   -0.4200   -0.2573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7536    0.6758   -0.9787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2279   -0.8329   -0.1348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3952    0.4650    0.8247 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  1  4  1  0
  1  5  1  0
  1  6  1  0
  3  7  1  0
  3  8  1  0
  3  9  1  0
M  END
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PDB for NP0001419 (Dimethylsulfide)

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1068                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  S   UNK     0       4.413  -0.385   0.000  0.00  0.00           S+0
HETATM    2  C   UNK     0       5.747   0.385   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.079   0.385   0.000  0.00  0.00           C+0
CONECT    1    2    3                                                       
CONECT    2    1                                                            
CONECT    3    1                                                            
MASTER        0    0    0    0    0    0    0    0    3    0    4    0
END
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3D PDB for NP0001419 (Dimethylsulfide)

COMPND    HMDB0002303
HETATM    1  C1  UNL     1       1.461   0.049   0.151  1.00  0.00           C  
HETATM    2  S1  UNL     1       0.092  -0.803  -0.672  1.00  0.00           S  
HETATM    3  C2  UNL     1      -1.458  -0.013  -0.169  1.00  0.00           C  
HETATM    4  H1  UNL     1       1.438  -0.257   1.221  1.00  0.00           H  
HETATM    5  H2  UNL     1       1.442   1.137   0.014  1.00  0.00           H  
HETATM    6  H3  UNL     1       2.402  -0.420  -0.257  1.00  0.00           H  
HETATM    7  H4  UNL     1      -1.754   0.676  -0.979  1.00  0.00           H  
HETATM    8  H5  UNL     1      -2.228  -0.833  -0.135  1.00  0.00           H  
HETATM    9  H6  UNL     1      -1.395   0.465   0.825  1.00  0.00           H  
CONECT    1    2    4    5    6
CONECT    2    3
CONECT    3    7    8    9
END
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SMILES for NP0001419 (Dimethylsulfide)

CSC
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INCHI for NP0001419 (Dimethylsulfide)

InChI=1S/C2H6S/c1-3-2/h1-2H3
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View in JSmol
Synonyms
ValueSource
(METHYLsulfanyl)methaneChEBI
2-ThiapropaneChEBI
[SMe2]ChEBI
Dimethyl sulphideChEBI
DMSChEBI
Methyl sulfideChEBI
Methyl thioetherChEBI
(METHYLsulphanyl)methaneGenerator
Dimethyl sulfideGenerator
Methyl sulphideGenerator
DimethylsulphideGenerator
Dimethyl sulfoxide(reduced)HMDB
MethylthiomethaneHMDB
2-ThiopropaneHMDB
Dimethyl monosulfideHMDB
Dimethyl sulfide (natural)HMDB
Dimethyl thioetherHMDB
DimethylsulfidHMDB
MethanethiomethaneHMDB
Methyl monosulfideHMDB
Methylthiomethyl radicalHMDB
MSMHMDB
Reduced-dmsoHMDB
Thiobis-methaneHMDB
ThiopropaneHMDB
Chemical FormulaC2H6S
Average Mass62.1340 Da
Monoisotopic Mass62.01902 Da
IUPAC Name(methylsulfanyl)methane
Traditional Namedimethyl sulfide
CAS Registry Number75-18-3
SMILES
CSC
InChI Identifier
InChI=1S/C2H6S/c1-3-2/h1-2H3
InChI KeyQMMFVYPAHWMCMS-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 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
Allium cepaFooDB
    • Mans Boelens, Pieter J. de Valois, Henk J. Wobben, and Arne van der Gen. Volatile Flavor Compound...
Allium sativumFooDB
Allium schoenoprasumFooDB
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Apium graveolens var. dulceFooDB
    • Glesni MacLeod and Jennifer M. Ames. Volatile components of celery and celeriac. Phytochemistry. ...
Apium graveolens var. rapaceumFooDB
    • Glesni MacLeod and Jennifer M. Ames. Volatile components of celery and celeriac. Phytochemistry. ...
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brassica oleracea var. botrytisFooDB
Brassica oleracea var. gongylodesFooDB
Brassica oleracea var. italicaFooDB
    • Charles F. Forney and Michael A. Jordan. Induction of Volatile Compounds in Broccoli by Postharve...
Bubalus bubalisFooDB
Cannabis sativaCannabisDB
      Not Available
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
Coffea arabicaKNApSAcK Database
Coffea arabica L.Plant
Coffea canephoraKNApSAcK Database
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Mentha spicataFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
Petroselinum crispumFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Solanum tuberosumFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Tuber borchii-
Tuber brumale-
Tuber excavatum-
Tuber indicum-
Tuber magnatum-
Tuber melanosporum-
Tuber mesentericum-
Tuber oligospermum-
Tuber panniferum-
Tuber rufum-
Tuber uncinatum-
Zea mays L.FooDB
    • LF. Flora and RC. Wiley. Flora and Wiley., 2007. Sweet corn aroma, chemical components and relati...
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dialkylthioethers. These are organosulfur compounds containing a thioether group that is substituted by two alkyl groups.
KingdomOrganic compounds
Super ClassOrganosulfur compounds
ClassThioethers
Sub ClassDialkylthioethers
Direct ParentDialkylthioethers
Alternative Parents
Substituents
  • Dialkylthioether
  • Sulfenyl compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-98.3 °CNot Available
Boiling Point37.30 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility22 mg/mL at 25 °CNot Available
LogP0.977 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility18.5 g/LALOGPS
logP0.59ALOGPS
logP1.22ChemAxon
logS-0.53ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity18.89 m³·mol⁻¹ChemAxon
Polarizability7.24 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002303
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003591
KNApSAcK IDC00053130
Chemspider ID1039
KEGG Compound IDC00580
BioCyc IDCPD-7670
BiGG IDNot Available
Wikipedia LinkDimethyl_sulfide
METLIN ID6603
PubChem Compound1068
PDB IDNot Available
ChEBI ID17437
Good Scents IDrw1022341
References
General References
  1. Rosen RT, Hiserodt RD, Fukuda EK, Ruiz RJ, Zhou Z, Lech J, Rosen SL, Hartman TG: The determination of metabolites of garlic preparations in breath and human plasma. Biofactors. 2000;13(1-4):241-9. [PubMed:11237188 ]
  2. 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 ]
  3. Yeung CK, Lang DH, Thummel KE, Rettie AE: Immunoquantitation of FMO1 in human liver, kidney, and intestine. Drug Metab Dispos. 2000 Sep;28(9):1107-11. [PubMed:10950857 ]
  4. Terazawa K, Kaji H, Akabane H, Takatori T: Determination of dimethyl sulphide in blood and adipose tissue by headspace gas analysis. J Chromatogr. 1991 Apr 19;565(1-2):453-6. [PubMed:1874893 ]
  5. Jiang T, Suarez FL, Levitt MD, Nelson SE, Ziegler EE: Gas production by feces of infants. J Pediatr Gastroenterol Nutr. 2001 May;32(5):534-41. [PubMed:11429513 ]
  6. Gahl WA, Ingelfinger J, Mohan P, Bernardini I, Hyman PE, Tangerman A: Intravenous cysteamine therapy for nephropathic cystinosis. Pediatr Res. 1995 Oct;38(4):579-84. [PubMed:8559613 ]
  7. Murata T, Fujiyama Y, Yamaga T, Miyazaki H: Breath malodor in an asthmatic patient caused by side-effects of medication: a case report and review of the literature. Oral Dis. 2003 Sep;9(5):273-6. [PubMed:14628896 ]
  8. Carrion O, Curson ARJ, Kumaresan D, Fu Y, Lang AS, Mercade E, Todd JD: A novel pathway producing dimethylsulphide in bacteria is widespread in soil environments. Nat Commun. 2015 Mar 25;6:6579. doi: 10.1038/ncomms7579. [PubMed:25807229 ]