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Showing metabocard for Dimethyldisulfide (HMDB0005879)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2007-04-12 16:35:55 UTC
Update Date2023-02-21 17:17:10 UTC
HMDB IDHMDB0005879
Secondary Accession Numbers
  • HMDB05879
Metabolite Identification
Common NameDimethyldisulfide
DescriptionDimethyldisulfide, also known as 2,3-dithiabutane, belongs to the class of organic compounds known as dialkyldisulfides. These are organic compounds containing a disulfide group R-SS-R' where R and R' are both alkyl groups. Dimethyldisulfide is a cabbage, citrus, and earthy tasting compound. Dimethyldisulfide is found, on average, in the highest concentration within a few different foods, such as kohlrabis (Brassica oleracea var. gongylodes), soft-necked garlics (Allium sativum L. var. sativum), and milk (cow). Dimethyldisulfide has also been detected, but not quantified in, several different foods, such as wild leeks (Allium ampeloprasum), welsh onions (Allium fistulosum), chickens (Gallus gallus), blackberries (Rubus), and evergreen blackberries (Rubus laciniatus). This could make dimethyldisulfide a potential biomarker for the consumption of these foods. Dimethyldisulfide is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Dimethyldisulfide, with regard to humans, has been found to be associated with several diseases such as perillyl alcohol administration for cancer treatment, irritable bowel syndrome, crohn's disease, and nonalcoholic fatty liver disease; dimethyldisulfide has also been linked to the inborn metabolic disorder celiac disease. Based on a literature review a significant number of articles have been published on Dimethyldisulfide.
Structure
Data?1676999830
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0005879 (Dimethyldisulfide)

12232
  Mrv0541 02231220312D          

  4  3  0  0  0  0            999 V2000
    2.3644   -0.2063    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.2063    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -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
  2  4  1  0  0  0  0
M  END
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3D MOL for HMDB0005879 (Dimethyldisulfide)

HMDB0005879
     RDKit          3D
Dimethyldisulfide
 10  9  0  0  0  0  0  0  0  0999 V2000
   -2.1601   -0.0295    0.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8862    1.1185   -0.4685 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.8618    0.2869   -1.1629 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.1519   -0.0312    0.0352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6313   -0.8636    0.6213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6386   -0.4852   -0.7889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8605    0.4115    0.7911 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1500    0.7489    0.8116 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9091   -0.9949    0.5681 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1039   -0.1615   -0.4868 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  1  5  1  0
  1  6  1  0
  1  7  1  0
  4  8  1  0
  4  9  1  0
  4 10  1  0
M  END
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3D SDF for HMDB0005879 (Dimethyldisulfide)

12232
  Mrv0541 02231220312D          

  4  3  0  0  0  0            999 V2000
    2.3644   -0.2063    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.2063    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -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
  2  4  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0005879

> <DATABASE_NAME>
hmdb

> <SMILES>
CSSC

> <INCHI_IDENTIFIER>
InChI=1S/C2H6S2/c1-3-4-2/h1-2H3

> <INCHI_KEY>
WQOXQRCZOLPYPM-UHFFFAOYSA-N

> <FORMULA>
C2H6S2

> <MOLECULAR_WEIGHT>
94.199

> <EXACT_MASS>
93.991091572

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
9.814507173761662

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(methyldisulfanyl)methane

> <ALOGPS_LOGP>
1.15

> <JCHEM_LOGP>
1.3502556653333335

> <ALOGPS_LOGS>
-1.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
27.1472

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.32e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dimethyl disulfide

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0005879 (Dimethyldisulfide)

HMDB0005879
     RDKit          3D
Dimethyldisulfide
 10  9  0  0  0  0  0  0  0  0999 V2000
   -2.1601   -0.0295    0.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8862    1.1185   -0.4685 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.8618    0.2869   -1.1629 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.1519   -0.0312    0.0352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6313   -0.8636    0.6213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6386   -0.4852   -0.7889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8605    0.4115    0.7911 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1500    0.7489    0.8116 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9091   -0.9949    0.5681 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1039   -0.1615   -0.4868 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  1  5  1  0
  1  6  1  0
  1  7  1  0
  4  8  1  0
  4  9  1  0
  4 10  1  0
M  END
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PDB for HMDB0005879 (Dimethyldisulfide)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 12232                                             
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       4.414  -0.385   0.000  0.00  0.00           S+0
HETATM    2  S   UNK     0       5.747   0.385   0.000  0.00  0.00           S+0
HETATM    3  C   UNK     0       3.080   0.385   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.081  -0.385   0.000  0.00  0.00           C+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1                                                            
CONECT    4    2                                                            
MASTER        0    0    0    0    0    0    0    0    4    0    6    0
END
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3D PDB for HMDB0005879 (Dimethyldisulfide)

COMPND    HMDB0005879
HETATM    1  C1  UNL     1      -2.160  -0.029   0.080  1.00  0.00           C  
HETATM    2  S1  UNL     1      -0.886   1.119  -0.468  1.00  0.00           S  
HETATM    3  S2  UNL     1       0.862   0.287  -1.163  1.00  0.00           S  
HETATM    4  C2  UNL     1       2.152  -0.031   0.035  1.00  0.00           C  
HETATM    5  H1  UNL     1      -1.631  -0.864   0.621  1.00  0.00           H  
HETATM    6  H2  UNL     1      -2.639  -0.485  -0.789  1.00  0.00           H  
HETATM    7  H3  UNL     1      -2.860   0.411   0.791  1.00  0.00           H  
HETATM    8  H4  UNL     1       2.150   0.749   0.812  1.00  0.00           H  
HETATM    9  H5  UNL     1       1.909  -0.995   0.568  1.00  0.00           H  
HETATM   10  H6  UNL     1       3.104  -0.162  -0.487  1.00  0.00           H  
CONECT    1    2    5    6    7
CONECT    2    3
CONECT    3    4
CONECT    4    8    9   10
END
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SMILES for HMDB0005879 (Dimethyldisulfide)

CSSC
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INCHI for HMDB0005879 (Dimethyldisulfide)

InChI=1S/C2H6S2/c1-3-4-2/h1-2H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
2,3-DithiabutaneChEBI
Dimethyl disulphideChEBI
Methyl disulfideChEBI
Dimethyl disulfideGenerator
Methyl disulphideGenerator
DimethyldisulphideGenerator
(Methyldisulfanyl)methaneHMDB
(methyldithio)MethaneHMDB
Disulfide dimethylHMDB
DMDSHMDB
MethyldisulfanylmethaneHMDB
MethyldisulfideHMDB
MethyldithiomethaneHMDB
Sulfa-hitechHMDB
Sulfa-hitech 0382HMDB
DimethyldisulfideChEBI
Chemical FormulaC2H6S2
Average Molecular Weight94.199
Monoisotopic Molecular Weight93.991091572
IUPAC Name(methyldisulfanyl)methane
Traditional Namedimethyl disulfide
CAS Registry Number624-92-0
SMILES
CSSC
InChI Identifier
InChI=1S/C2H6S2/c1-3-4-2/h1-2H3
InChI KeyWQOXQRCZOLPYPM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dialkyldisulfides. These are organic compounds containing a disulfide group R-SS-R' where R and R' are both alkyl groups.
KingdomOrganic compounds
Super ClassOrganosulfur compounds
ClassOrganic disulfides
Sub ClassDialkyldisulfides
Direct ParentDialkyldisulfides
Alternative Parents
Substituents
  • Dialkyldisulfide
  • Sulfenyl compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Biological roleIndustrial application
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-85 °CNot Available
Boiling Point109.00 to 110.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility3 mg/mL at 25 °CNot Available
LogP1.77HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Abnormal Concentrations
Associated Disorders and Diseases
Disease References
Ulcerative colitis
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
  2. Walton C, Fowler DP, Turner C, Jia W, Whitehead RN, Griffiths L, Dawson C, Waring RH, Ramsden DB, Cole JA, Cauchi M, Bessant C, Hunter JO: Analysis of volatile organic compounds of bacterial origin in chronic gastrointestinal diseases. Inflamm Bowel Dis. 2013 Sep;19(10):2069-78. doi: 10.1097/MIB.0b013e31829a91f6. [PubMed:23867873 ]
  3. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Celiac disease
  1. Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Crohn's disease
  1. Walton C, Fowler DP, Turner C, Jia W, Whitehead RN, Griffiths L, Dawson C, Waring RH, Ramsden DB, Cole JA, Cauchi M, Bessant C, Hunter JO: Analysis of volatile organic compounds of bacterial origin in chronic gastrointestinal diseases. Inflamm Bowel Dis. 2013 Sep;19(10):2069-78. doi: 10.1097/MIB.0b013e31829a91f6. [PubMed:23867873 ]
  2. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Irritable bowel syndrome
  1. Walton C, Fowler DP, Turner C, Jia W, Whitehead RN, Griffiths L, Dawson C, Waring RH, Ramsden DB, Cole JA, Cauchi M, Bessant C, Hunter JO: Analysis of volatile organic compounds of bacterial origin in chronic gastrointestinal diseases. Inflamm Bowel Dis. 2013 Sep;19(10):2069-78. doi: 10.1097/MIB.0b013e31829a91f6. [PubMed:23867873 ]
Autism
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Pervasive developmental disorder not otherwise specified
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Perillyl alcohol administration for cancer treatment
  1. Silva CL, Passos M, Camara JS: Solid phase microextraction, mass spectrometry and metabolomic approaches for detection of potential urinary cancer biomarkers--a powerful strategy for breast cancer diagnosis. Talanta. 2012 Jan 30;89:360-8. doi: 10.1016/j.talanta.2011.12.041. Epub 2011 Dec 22. [PubMed:22284503 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003491
KNApSAcK IDC00001245
Chemspider ID11731
KEGG Compound IDC08371
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethyl_disulfide
METLIN IDNot Available
PubChem Compound12232
PDB IDNot Available
ChEBI ID4608
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1008081
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Zlatkis A, Liebich HM: Profile of volatile metabolites in human urine. Clin Chem. 1971 Jul;17(7):592-4. [PubMed:5556886 ]
  2. Greenman J, Duffield J, Spencer P, Rosenberg M, Corry D, Saad S, Lenton P, Majerus G, Nachnani S, El-Maaytah M: Study on the organoleptic intensity scale for measuring oral malodor. J Dent Res. 2004 Jan;83(1):81-5. [PubMed:14691119 ]
  3. Volozhin AI, Petrovich IuA, Filatova ES, Barer GM, Fomina OL, Kreit KhN, Volozhina SA, Dieva SV: [Volatile compounds in air and oral saliva in healthy people, and in periodontitis and gingivitis patients]. Stomatologiia (Mosk). 2001;80(1):9-12. [PubMed:11236158 ]
  4. Jappinen P, Kangas J, Silakoski L, Savolainen H: Volatile metabolites in occupational exposure to organic sulfur compounds. Arch Toxicol. 1993;67(2):104-6. [PubMed:8481097 ]