Showing metabocard for S-Methylmethionine (MMDBc0000672)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:52:25 UTC
Update Date2024-04-30 19:33:28 UTC
Metabolite IDMMDBc0000672
Metabolite Identification
Common NameS-Methylmethionine
DescriptionS-Methylmethionine (SMM) belongs to the class of organic compounds known as methionines and derivatives. Methionines and derivatives are compounds containing methionine or a derivative thereof resulting from reaction of methionine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. S-Methylmethionine is a derivative of methionine. It is biosynthesized from L-methionine which is first converted to S-adenosylmethionine. The subsequent conversion, involving replacement of the adenosyl group by a methyl group is catalyzed by the enzyme methionine S-methyltransferase. S-methylmethionine is particularly abundant in plants, being more abundant than methionine. As a result, S-Methylmethionine is found, on average, in the highest concentration within a few different plant foods, such as teas (Camellia sinensis), red tea, and herbal tea and in a lower concentration in green tea, black tea. It is also found in garden tomatoes. S-Methylmethionine has also been detected, but not quantified in, several different foods, such as prunus (cherry, plum), barley, nuts, root vegetables, onion-family vegetables, and sapodillas (Manilkara zapota). This could make S-methylmethionine a potential biomarker for the consumption of these foods. S-Methylmethionine is naturally found in barley and is further created during the malting process to produce beer. SMM can be subsequently converted to dimethyl sulfide (DMS) during the malt kilning process, causing an undesirable flavor in beer. Lightly kilned malts such as pilsner or lager malts retain much of their SMM content while higher kilned malt such as pale ale malt has substantially more of the SMM converted to DMS in the malt. S- The biological roles of S-methylmethionine are not well understood. Speculated roles include methionine storage, use as a methyl donor, regulation of S-adenosylmethionine. 
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x0000564af39661f0>


  Mrv0541 05061310342D          

 10  9  0  0  0  0            999 V2000
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    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
    2.1434    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 S   0  3  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  5  3  1  0  0  0  0
  6  5  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
  9  6  1  0  0  0  0
 10  1  1  0  0  0  0
 10  2  1  0  0  0  0
 10  4  1  0  0  0  0
M  CHG  1  10   1
M  END
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3D MOL for #<Metabolite:0x0000564af39661f0>

HMDB0038670
     RDKit          3D
S-Methylmethionine
 24 23  0  0  0  0  0  0  0  0999 V2000
    2.5835    1.2477   -0.0409 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9317   -0.1837    0.7487 S   0  0  0  0  0  3  0  0  0  0  0  0
    3.0417   -1.5436    0.4952 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3344   -0.6296    0.1469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6923    0.4394    0.3407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0059   -0.0738   -0.2170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4547   -1.2709    0.4388 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0515    0.9845   -0.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1534    0.7394    0.3858 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7536    2.1895   -0.7744 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8935    2.0948   -0.0637 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4984    1.5506    0.5141 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9202    0.9355   -1.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2780   -1.5733   -0.5887 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6085   -2.5040    0.8591 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0110   -1.3326    1.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3476   -0.9259   -0.9243 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0032   -1.5248    0.7088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8423    0.6691    1.4095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4588    1.3694   -0.2169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8331   -0.3184   -1.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3650   -2.1117   -0.1607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4035   -1.1807    0.8463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4377    2.9530   -0.1781 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
 10 24  1  0
M  CHG  1   2   1
M  END
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3D SDF for #<Metabolite:0x0000564af39661f0>


  Mrv0541 05061310342D          

 10  9  0  0  0  0            999 V2000
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    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
    2.1434    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 S   0  3  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  5  3  1  0  0  0  0
  6  5  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
  9  6  1  0  0  0  0
 10  1  1  0  0  0  0
 10  2  1  0  0  0  0
 10  4  1  0  0  0  0
M  CHG  1  10   1
M  END
> <DATABASE_ID>
MMDBc0000672

> <DATABASE_NAME>
MIME

> <SMILES>
C[S+](C)CCC(N)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H13NO2S/c1-10(2)4-3-5(7)6(8)9/h5H,3-4,7H2,1-2H3/p+1

> <INCHI_KEY>
YDBYJHTYSHBBAU-UHFFFAOYSA-O

> <FORMULA>
C6H14NO2S

> <MOLECULAR_WEIGHT>
164.246

> <EXACT_MASS>
164.074524387

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
17.684953044142915

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3-amino-3-carboxypropyl)dimethylsulfanium

> <ALOGPS_LOGP>
-1.27

> <JCHEM_LOGP>
-3.3250557102888223

> <ALOGPS_LOGS>
-1.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.236989607571266

> <JCHEM_PKA_STRONGEST_BASIC>
9.414777499242314

> <JCHEM_POLAR_SURFACE_AREA>
63.32000000000001

> <JCHEM_REFRACTIVITY>
41.0974

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.12e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
S-methylmethionine

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x0000564af39661f0>

HMDB0038670
     RDKit          3D
S-Methylmethionine
 24 23  0  0  0  0  0  0  0  0999 V2000
    2.5835    1.2477   -0.0409 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9317   -0.1837    0.7487 S   0  0  0  0  0  3  0  0  0  0  0  0
    3.0417   -1.5436    0.4952 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3344   -0.6296    0.1469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6923    0.4394    0.3407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0059   -0.0738   -0.2170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4547   -1.2709    0.4388 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0515    0.9845   -0.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1534    0.7394    0.3858 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7536    2.1895   -0.7744 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8935    2.0948   -0.0637 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4984    1.5506    0.5141 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9202    0.9355   -1.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2780   -1.5733   -0.5887 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6085   -2.5040    0.8591 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0110   -1.3326    1.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3476   -0.9259   -0.9243 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0032   -1.5248    0.7088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8423    0.6691    1.4095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4588    1.3694   -0.2169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8331   -0.3184   -1.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3650   -2.1117   -0.1607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4035   -1.1807    0.8463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4377    2.9530   -0.1781 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
 10 24  1  0
M  CHG  1   2   1
M  END
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PDB for #<Metabolite:0x0000564af39661f0>

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       4.001   2.310   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0       6.668   0.770   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       5.335  -1.540   0.000  0.00  0.00           O+0
HETATM   10  S   UNK     0       0.000   0.000   0.000  0.00  0.00           S+1
CONECT    1   10                                                            
CONECT    2   10                                                            
CONECT    3    4    5                                                       
CONECT    4    3   10                                                       
CONECT    5    3    6    7                                                  
CONECT    6    5    8    9                                                  
CONECT    7    5                                                            
CONECT    8    6                                                            
CONECT    9    6                                                            
CONECT   10    1    2    4                                                  
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
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3D PDB for #<Metabolite:0x0000564af39661f0>

COMPND    HMDB0038670
HETATM    1  C1  UNL     1       2.583   1.248  -0.041  1.00  0.00           C  
HETATM    2  S1  UNL     1       1.932  -0.184   0.749  1.00  0.00           S1+
HETATM    3  C2  UNL     1       3.042  -1.544   0.495  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.334  -0.630   0.147  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.692   0.439   0.341  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.006  -0.074  -0.217  1.00  0.00           C  
HETATM    7  N1  UNL     1      -2.455  -1.271   0.439  1.00  0.00           N  
HETATM    8  C6  UNL     1      -3.052   0.985  -0.180  1.00  0.00           C  
HETATM    9  O1  UNL     1      -4.153   0.739   0.386  1.00  0.00           O  
HETATM   10  O2  UNL     1      -2.754   2.189  -0.774  1.00  0.00           O  
HETATM   11  H1  UNL     1       1.894   2.095  -0.064  1.00  0.00           H  
HETATM   12  H2  UNL     1       3.498   1.551   0.514  1.00  0.00           H  
HETATM   13  H3  UNL     1       2.920   0.935  -1.064  1.00  0.00           H  
HETATM   14  H4  UNL     1       3.278  -1.573  -0.589  1.00  0.00           H  
HETATM   15  H5  UNL     1       2.608  -2.504   0.859  1.00  0.00           H  
HETATM   16  H6  UNL     1       4.011  -1.333   1.028  1.00  0.00           H  
HETATM   17  H7  UNL     1       0.348  -0.926  -0.924  1.00  0.00           H  
HETATM   18  H8  UNL     1       0.003  -1.525   0.709  1.00  0.00           H  
HETATM   19  H9  UNL     1      -0.842   0.669   1.409  1.00  0.00           H  
HETATM   20  H10 UNL     1      -0.459   1.369  -0.217  1.00  0.00           H  
HETATM   21  H11 UNL     1      -1.833  -0.318  -1.282  1.00  0.00           H  
HETATM   22  H12 UNL     1      -2.365  -2.112  -0.161  1.00  0.00           H  
HETATM   23  H13 UNL     1      -3.403  -1.181   0.846  1.00  0.00           H  
HETATM   24  H14 UNL     1      -2.438   2.953  -0.178  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3    4
CONECT    3   14   15   16
CONECT    4    5   17   18
CONECT    5    6   19   20
CONECT    6    7    8   21
CONECT    7   22   23
CONECT    8    9    9   10
CONECT   10   24
END
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SMILES for #<Metabolite:0x0000564af39661f0>

C[S+](C)CCC(N)C(O)=O
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INCHI for #<Metabolite:0x0000564af39661f0>

InChI=1S/C6H13NO2S/c1-10(2)4-3-5(7)6(8)9/h5H,3-4,7H2,1-2H3/p+1
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Synonyms
ValueSource
(3-amino-3-Carboxypropyl)dimethylsulfonium(1+), 9ci, 8ciHMDB
S-Methyl-L-methionineHMDB
Chloride, methionine methylsulfoniumMeSH, HMDB
Methionine methylsulfonium chlorideMeSH, HMDB
MethylmethionineMeSH, HMDB
Methylmethionine sulfonium chlorideMeSH, HMDB
Methylsulfonium chloride, methionineMeSH, HMDB
S MethylmethionineMeSH, HMDB
Chloride, methylmethioninesulfoniumMeSH, HMDB
Sulfonium, ((3S)-3-amino-3-carboxypropyl)dimethyl-, inner saltMeSH, HMDB
Methylmethioninesulfonium chlorideMeSH, HMDB
Vitamin uMeSH, HMDB
Molecular FormulaC6H14NO2S
Average Mass164.246
Monoisotopic Mass164.074524387
IUPAC Name(3-amino-3-carboxypropyl)dimethylsulfanium
Traditional NameS-methylmethionine
CAS Registry NumberNot Available
SMILES
C[S+](C)CCC(N)C(O)=O
InChI Identifier
InChI=1S/C6H13NO2S/c1-10(2)4-3-5(7)6(8)9/h5H,3-4,7H2,1-2H3/p+1
InChI KeyYDBYJHTYSHBBAU-UHFFFAOYSA-O