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Showing NP-Card for Methyl methanethiosulfonate (NP0047329)

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Record Information
Version1.0
Created at2022-03-17 20:38:23 UTC
Updated at2022-03-17 20:38:23 UTC
NP-MRD IDNP0047329
Secondary Accession NumbersNone
Natural Product Identification
Common NameMethyl methanethiosulfonate
DescriptionMethyl methanethiosulfonate, also known as MMTS, belongs to the class of organic compounds known as sulfonyls. Sulfonyls are compounds containing the sulfonyl group, with the general structure RS(=O)2R' ( R,R' must not be H). Methyl methanethiosulfonate is an extremely weak basic (essentially neutral) compound (based on its pKa). Methyl methanethiosulfonate exists in all living organisms, ranging from bacteria to humans. Methyl methanethiosulfonate is a pungent, roasted, and sulfurous tasting compound. Outside of the human body, Methyl methanethiosulfonate has been detected, but not quantified in, a few different foods, such as brassicas, garden onions, and onion-family vegetables. This could make methyl methanethiosulfonate a potential biomarker for the consumption of these foods. Methyl methanethiosulfonate is found in Brassica oleracea, Scorodophloeus zenkeri and Trypanosoma brucei. It was first documented in 1989 (PMID: 2909257). A sulfonic acid derivative obtained by condensaton of methanesulfonic acid with methanethiol (PMID: 7532583).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047329 (Methyl methanethiosulfonate)

Structure #1
  Mrv0541 02241207342D          

  6  5  0  0  0  0            999 V2000
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  6  2  0  0  0  0
  4  6  2  0  0  0  0
  5  6  1  0  0  0  0
M  END
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3D MOL for NP0047329 (Methyl methanethiosulfonate)

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3D SDF for NP0047329 (Methyl methanethiosulfonate)
Structure #1
  Mrv0541 02241207342D          

  6  5  0  0  0  0            999 V2000
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  6  2  0  0  0  0
  4  6  2  0  0  0  0
  5  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047329

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C2H6O2S2/c1-5-6(2,3)4/h1-2H3

> <INCHI_KEY>
XYONNSVDNIRXKZ-UHFFFAOYSA-N

> <FORMULA>
C2H6O2S2

> <MOLECULAR_WEIGHT>
126.198

> <EXACT_MASS>
125.980920816

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
11.301463231272763

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(methanesulfonylsulfanyl)methane

> <ALOGPS_LOGP>
-0.40

> <JCHEM_LOGP>
-0.06164452933333317

> <ALOGPS_LOGS>
-0.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-9.12292413651124

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
27.5405

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.43e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl methanethiosulfonate

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0047329 (Methyl methanethiosulfonate)
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PDB for NP0047329 (Methyl methanethiosulfonate)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Structure #1                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.540   0.000   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       0.000  -1.540   0.000  0.00  0.00           O+0
HETATM    5  S   UNK     0       1.540   0.000   0.000  0.00  0.00           S+0
HETATM    6  S   UNK     0       0.000   0.000   0.000  0.00  0.00           S+0
CONECT    1    5                                                            
CONECT    2    6                                                            
CONECT    3    6                                                            
CONECT    4    6                                                            
CONECT    5    1    6                                                       
CONECT    6    2    3    4    5                                             
MASTER        0    0    0    0    0    0    0    0    6    0   10    0
END

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3D PDB for NP0047329 (Methyl methanethiosulfonate)
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SMILES for NP0047329 (Methyl methanethiosulfonate)
CSS(C)(=O)=O
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INCHI for NP0047329 (Methyl methanethiosulfonate)
InChI=1S/C2H6O2S2/c1-5-6(2,3)4/h1-2H3
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Synonyms
ValueSource
Methyl methanethiolsulfonateChEBI
Methyl methanethiolsulfonic acidGenerator
Methyl methanethiolsulphonateGenerator
Methyl methanethiolsulphonic acidGenerator
Methyl methanethiosulfonic acidGenerator
Methyl methanethiosulphonateGenerator
Methyl methanethiosulphonic acidGenerator
Dimethyl thiosulfonateHMDB
Methanesulfonic acid, thio-, S-methyl esterHMDB
Methanesulfonothioic acid, S-methyl esterHMDB
Methanethiosulfonic acid, S-methyl esterHMDB
Methyl methanesulfonothioateHMDB
Methyl methanethio-sulfonateHMDB
MethylmethanethiosulfonateHMDB
MMTSHMDB
S-Methyl methanesulfonothioateHMDB
S-Methyl methanethiosulfonateHMDB
S-Methyl methanethiosulphonateHMDB
S-Methyl methylthiosulfonateHMDB
S-Methyl thiomethanesulfonateHMDB
S-Methyl methanethiosulfonic acidGenerator
S-Methyl methanethiosulphonic acidGenerator
Methyl methanethiosulfonateMeSH
Chemical FormulaC2H6O2S2
Average Mass126.1980 Da
Monoisotopic Mass125.98092 Da
IUPAC Name(methanesulfonylsulfanyl)methane
Traditional Namemethyl methanethiosulfonate
CAS Registry Number2949-92-0
SMILES
CSS(C)(=O)=O
InChI Identifier
InChI=1S/C2H6O2S2/c1-5-6(2,3)4/h1-2H3
InChI KeyXYONNSVDNIRXKZ-UHFFFAOYSA-N
Experimental Spectra
Not Available
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 fistulosumFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Brassica oleraceaLOTUS Database
Scorodophloeus zenkeriLOTUS Database
Trypanosoma bruceiLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sulfonyls. Sulfonyls are compounds containing the sulfonyl group, with the general structure RS(=O)2R' ( R,R' must not be H).
KingdomOrganic compounds  
Super ClassOrganosulfur compounds  
ClassSulfonyls  
Sub ClassNot Available
Direct ParentSulfonyls  
Alternative Parents
Substituents
  • Sulfonyl
    • 

  • Sulfenyl compound
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • 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
logP-0.4ALOGPS
logP-0.062ChemAxon
logS-0.57ALOGPS
pKa (Strongest Basic)-9.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity27.54 m³·mol⁻¹ChemAxon
Polarizability11.3 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0031832  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008510  
KNApSAcK IDNot Available
Chemspider ID17065  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound18064  
PDB IDZ22  
ChEBI ID74357  
Good Scents IDNot Available
References
General References
  1. Jensen PE, Shanbhag VP, Stigbrand T: Methanethiolation of the liberated cysteine residues of human alpha 2-macroglobulin treated with methylamine generates a derivative with similar functional characteristics as native alpha 2-macroglobulin. Eur J Biochem. 1995 Feb 1;227(3):612-6. doi: 10.1111/j.1432-1033.1995.tb20180.x. [PubMed:7532583  ] 
  2. Alvear M, Jabalquinto AM, Cardemil E: Inactivation of chicken liver mevalonate 5-diphosphate decarboxylase by sulfhydryl-directed reagents: evidence of a functional dithiol. Biochim Biophys Acta. 1989 Jan 19;994(1):7-11. doi: 10.1016/0167-4838(89)90055-1. [PubMed:2909257  ]