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Showing NP-Card for S-Methyl-L-methionine (NP0049191)

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Record Information
Version2.0
Created at2022-03-17 21:08:33 UTC
Updated at2022-03-17 21:08:33 UTC
NP-MRD IDNP0049191
Secondary Accession NumbersNone
Natural Product Identification
Common NameS-Methyl-L-methionine
DescriptionS-Methylmethionine, also known as vitamin u, belongs to the class of organic compounds known as methionine and derivatives. Methionine 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 sometimes referred to as vitamin U, but it is not considered a true vitamin. 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-Methylmethionine is a very strong basic compound (based on its pKa). Outside of the human body, S-Methylmethionine is found, on average, in the highest concentration within tea and garden tomato (var.). S-Methylmethionine has also been detected, but not quantified in, several different foods, such as yardlong beans, chicory leaves, daikon radish, pistachio, and spearmints. This could make S-methylmethionine a potential biomarker for the consumption of these foods. S-Methylmethionine is claimed to have protective effects in the gastrointestinal mucosa and in the liver. Darker kilned malts such as Munich malt have virtually no SMM content since most has been converted to DMS. The coproduct is S-adenosyl homocysteine. A few plants use S-methylmethionine as a precursor to the osmolyte dimethylsulfoniopropionate (DMSP).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0049191 (S-Methyl-L-methionine)


  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 NP0049191 (S-Methyl-L-methionine)

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3D SDF for NP0049191 (S-Methyl-L-methionine)

  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>
NP0049191

> <DATABASE_NAME>
NP-MRD

> <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 NP0049191 (S-Methyl-L-methionine)
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PDB for NP0049191 (S-Methyl-L-methionine)
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 NP0049191 (S-Methyl-L-methionine)
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SMILES for NP0049191 (S-Methyl-L-methionine)
C[S+](C)CCC(N)C(O)=O
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INCHI for NP0049191 (S-Methyl-L-methionine)
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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View in JSmol
Synonyms
ValueSource
(3-Amino-3-carboxypropyl)dimethylsulfonium(1+), 9ci, 8ciHMDB
S-Methyl-L-methionineHMDB
Chloride, methionine methylsulfoniumHMDB
Methionine methylsulfonium chlorideHMDB
MethylmethionineHMDB
Methylmethionine sulfonium chlorideHMDB
Methylsulfonium chloride, methionineHMDB
S MethylmethionineHMDB
Chloride, methylmethioninesulfoniumHMDB
Sulfonium, ((3S)-3-amino-3-carboxypropyl)dimethyl-, inner saltHMDB
Methylmethioninesulfonium chlorideHMDB
Vitamin uHMDB
Chemical FormulaC6H14NO2S
Average Mass164.2460 Da
Monoisotopic Mass164.07452 Da
IUPAC Name(3-amino-3-carboxypropyl)dimethylsulfanium
Traditional NameS-methylmethionine
CAS Registry Number13065-25-3
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
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Allium sativumFooDB
Apium graveolensFooDB
Solanum lycopersicum var. lycopersicumFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as methionine and derivatives. Methionine 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.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentMethionine and derivatives  
Alternative Parents
Substituents
  • Methionine or derivatives
    • 

  • Alpha-amino acid
    • 

  • Thia fatty acid
    • 

  • Fatty acid
    • 

  • Fatty acyl
    • 

  • Amino acid
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organic nitrogen compound
    • 

  • Amine
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Primary amine
    • 

  • Organosulfur compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Primary aliphatic amine
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Organic cation
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
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-1.3ALOGPS
logP-3.3ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)2.24ChemAxon
pKa (Strongest Basic)9.41ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity41.1 m³·mol⁻¹ChemAxon
Polarizability17.68 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0038670  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB018070  
KNApSAcK IDNot Available
Chemspider ID445  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkS-Methylmethionine  
METLIN IDNot Available
PubChem Compound458  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available