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Showing NP-Card for Dimethyl trisulfide (NP0047883)

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Record Information
Version2.0
Created at2022-03-17 20:47:31 UTC
Updated at2022-03-17 20:47:31 UTC
NP-MRD IDNP0047883
Secondary Accession NumbersNone
Natural Product Identification
Common NameDimethyl trisulfide
DescriptionDimethyl trisulfide, also known as DMTS or sulfa-hitech, belongs to the class of organic compounds known as organic trisulfides. These are organosulfur compounds with the general formula RSSSR' (R,R'=alkyl, aryl). Dimethyl trisulfide is possibly neutral. Dimethyl trisulfide exists in all eukaryotes, ranging from yeast to humans. Dimethyl trisulfide is a cabbage, cooked, and fish tasting compound. Outside of the human body, Dimethyl trisulfide is found, on average, in the highest concentration within a few different foods, such as kohlrabis, soft-necked garlics, and milk (cow). Dimethyl trisulfide has also been detected, but not quantified in, several different foods, such as fruits, cereals and cereal products, allium (onion), garlics, and brassicas. This could make dimethyl trisulfide a potential biomarker for the consumption of these foods. Found in essential oil of hop (Humulus lupulus), garlic (Allium sativum), shallot (Allium cepa) and ramsons (Allium ursinum)and is also found in pineapple, raw cabbage, kohrabi, roasted filberts, roasted peanuts, edible mushrooms, brussel sprouts, fermented radish, Chinese cabbage, parsnips, scallop and squid. Dimethyl trisulfide is found in Allium ursinum , Homo sapiens (Skin), Humulus lupulus , Phallus impudicus , Pilosocereus tweedyanus and Sauromatum guttatum. Dimethyl trisulfide was first documented in 1993 (PMID: 8481097). Dimethyl trisulfide, with regard to humans, has been found to be associated with several diseases such as perillyl alcohol administration for cancer treatment, autism, pervasive developmental disorder not otherwise specified, and nonalcoholic fatty liver disease; dimethyl trisulfide has also been linked to the inborn metabolic disorder celiac disease (PMID: 16840607) (PMID: 14691119) (PMID: 11236158).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047883 (Dimethyl trisulfide)


  Mrv1652304272018432D          

  5  4  0  0  0  0            999 V2000
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    0.4125    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  5  1  0  0  0  0
M  END
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3D MOL for NP0047883 (Dimethyl trisulfide)

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3D SDF for NP0047883 (Dimethyl trisulfide)

  Mrv1652304272018432D          

  5  4  0  0  0  0            999 V2000
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    0.4125    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  5  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047883

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CSSSC

> <INCHI_IDENTIFIER>
InChI=1S/C2H6S3/c1-3-5-4-2/h1-2H3

> <INCHI_KEY>
YWHLKYXPLRWGSE-UHFFFAOYSA-N

> <FORMULA>
C2H6S3

> <MOLECULAR_WEIGHT>
126.264

> <EXACT_MASS>
125.963162262

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
12.464733689805152

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
dimethyltrisulfane

> <ALOGPS_LOGP>
1.26

> <JCHEM_LOGP>
1.944654209

> <ALOGPS_LOGS>
-1.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
32.903

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.20e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dimethyl trisulfide

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0047883 (Dimethyl trisulfide)
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PDB for NP0047883 (Dimethyl trisulfide)
HEADER    PROTEIN                                 27-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-20         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    3  S   UNK     0       1.334   0.770   0.000  0.00  0.00           S+0
HETATM    4  S   UNK     0       4.001   0.770   0.000  0.00  0.00           S+0
HETATM    5  S   UNK     0       2.667   0.000   0.000  0.00  0.00           S+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1    5                                                       
CONECT    4    2    5                                                       
CONECT    5    3    4                                                       
MASTER        0    0    0    0    0    0    0    0    5    0    8    0
END

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3D PDB for NP0047883 (Dimethyl trisulfide)
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SMILES for NP0047883 (Dimethyl trisulfide)
CSSSC
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INCHI for NP0047883 (Dimethyl trisulfide)
InChI=1S/C2H6S3/c1-3-5-4-2/h1-2H3
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View in JSmol
Synonyms
ValueSource
DMTSKegg
Dimethyl trisulphideGenerator
(Methyltrisulphanyl)methaneHMDB
(Methyldisulfanyl)methaneHMDB
(Methyldithio)methaneHMDB
1,3-Dimethyltrisulfane (acd/name 4.0)HMDB
2,3,4-TrithiapentaneHMDB
2,3-DithiabutaneHMDB
CH3SSSCH3HMDB
Dimethyl disulfideHMDB
Dimethyl disulphideHMDB
Dimethyl trisufideHMDB
DimethyldisulfideHMDB
Disulfide dimethylHMDB
DMDSHMDB
Methyl disulfideHMDB
Methyl trisulfideHMDB
MethyldisulfanylmethaneHMDB
MethyldisulfideHMDB
MethyldithiomethaneHMDB
Sulfa-hitechHMDB
Sulfa-hitech 0382HMDB
Trisulfide, dimethylHMDB
DimethyltrisulphideGenerator
Chemical FormulaC2H6S3
Average Mass126.2640 Da
Monoisotopic Mass125.96316 Da
IUPAC Namedimethyltrisulfane
Traditional Namedimethyl trisulfide
CAS Registry Number3658-80-8
SMILES
CSSSC
InChI Identifier
InChI=1S/C2H6S3/c1-3-5-4-2/h1-2H3
InChI KeyYWHLKYXPLRWGSE-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Agaricus bisporusFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Allium cepaFooDB
    • Heikki Kallio and Lea Salorinne. Comparison of Onion Varieties by Headspace Gas Chromatography-Ma...
Allium cepa L.FooDB
    • J. F. Carson and Francis F. Wong. The Volatile Flavor Components of Onions. J. Agric. Food Chem. ...
Allium fistulosumFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Allium sativumFooDB
Allium ursinumPlant
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brassica oleracea var. botrytisFooDB
Brassica oleracea var. capitataFooDB
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
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Cucumis sativus L.FooDB
    • Ancheng Zhou and Roger F. McFeeters. Volatile Compounds in Cucumbers Fermented in Low-Salt Condit...
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Homo sapiens (Skin)Animalia
Humulus lupulusPlant
Lagopus mutaFooDB
Lentinus edodesFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
Phallus impudicus-
PhasianidaeFooDB
Phasianus colchicusFooDB
Pilosocereus tweedyanusPlant
Pleurotus ostreatusFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Psidium guajavaFooDB
Sauromatum guttatumPlant
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as organic trisulfides. These are organosulfur compounds with the general formula RSSSR' (R,R'=alkyl, aryl).
KingdomOrganic compounds  
Super ClassOrganosulfur compounds  
ClassOrganic trisulfides  
Sub ClassNot Available
Direct ParentOrganic trisulfides  
Alternative Parents
Substituents
  • Organic trisulfide
    • 

  • Sulfenyl compound
    • 

  • Hydrocarbon derivative
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.26ALOGPS
logP1.94ChemAxon
logS-1.8ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity32.9 m³·mol⁻¹ChemAxon
Polarizability12.46 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0013780  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012458  
KNApSAcK IDC00001246  
Chemspider ID18219  
KEGG Compound IDC08372  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDimethyl trisulfide  
METLIN IDNot Available
PubChem Compound19310  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Vazquez-Landaverde PA, Torres JA, Qian MC: Quantification of trace volatile sulfur compounds in milk by solid-phase microextraction and gas chromatography-pulsed flame photometric detection. J Dairy Sci. 2006 Aug;89(8):2919-27. doi: 10.3168/jds.S0022-0302(06)72564-4. [PubMed:16840607  ] 
  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. doi: 10.1177/154405910408300116. [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. doi: 10.1007/BF01973679. [PubMed:8481097  ]