Showing metabocard for L-Methionine sulfoximine (MMDBc0057120)

Pharmaceutical
Xenobiotic
Record Information
Version2.0
StatusDetected and Quantified
Creation Date2022-10-17 17:54:39 UTC
Update Date2025-10-07 16:09:50 UTC
Metabolite IDMMDBc0057120
Metabolite Identification
Common NameL-Methionine sulfoximine
DescriptionL-Methionine sulfoximine is a sulfoximine compound classified as a metabolic inhibitor. It is structurally characterized by the presence of a sulfoximine functional group attached to the methionine backbone, which alters its biochemical properties. This compound acts primarily as an inhibitor of glutamine synthetase (GS), an enzyme crucial for the conversion of glutamate and ammonia into glutamine, thus playing a significant role in nitrogen metabolism and neurotransmitter cycling. By inhibiting GS, L-Methionine sulfoximine can influence various metabolic pathways, particularly in conditions such as acute lung injury (ALI), where it has been shown to be effective in experimental models. For instance, in studies involving mice, the administration of L-methionine sulfoximine was utilized as part of a strategy to mitigate ALI, alongside other interventions like CCL2 neutralizing antibodies and gene therapy approaches to enhance GS expression (PMID:40485395 ). This highlights its potential role in modulating metabolic pathways related to inflammation and cellular stress responses.
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00007f2ab83de340>


  Mrv1652310172219542D          

 11 10  0  0  1  0            999 V2000
    0.8250    1.4289    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -2.1434    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.8579    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230   -2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  2  0  0  0  0
  7 10  1  0  0  0  0
  4 11  1  6  0  0  0
M  CHG  2   1  -1  11   1
M  END
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3D MOL for #<Metabolite:0x00007f2ab83de340>

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3D SDF for #<Metabolite:0x00007f2ab83de340>

  Mrv1652310172219542D          

 11 10  0  0  1  0            999 V2000
    0.8250    1.4289    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -2.1434    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.8579    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230   -2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  2  0  0  0  0
  7 10  1  0  0  0  0
  4 11  1  6  0  0  0
M  CHG  2   1  -1  11   1
M  END
> <DATABASE_ID>
MMDBc0057120

> <DATABASE_NAME>
MIME

> <SMILES>
CS(=N)(=O)CC[C@H]([NH3+])C([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H12N2O3S/c1-11(7,10)3-2-4(6)5(8)9/h4,7H,2-3,6H2,1H3,(H,8,9)/t4-,11?/m0/s1

> <INCHI_KEY>
SXTAYKAGBXMACB-DPVSGNNYSA-N

> <FORMULA>
C5H12N2O3S

> <MOLECULAR_WEIGHT>
180.22

> <EXACT_MASS>
180.056863428

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
17.16653265624597

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-azaniumyl-4-[imino(methyl)oxo-lambda6-sulfanyl]butanoate

> <ALOGPS_LOGP>
-1.54

> <JCHEM_LOGP>
-4.446533138197991

> <ALOGPS_LOGS>
-2.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8865595865396951

> <JCHEM_PKA_STRONGEST_BASIC>
9.091048462528423

> <JCHEM_POLAR_SURFACE_AREA>
108.69

> <JCHEM_REFRACTIVITY>
62.34670000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.04e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-ammonio-4-[imino(methyl)oxo-lambda6-sulfanyl]butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for #<Metabolite:0x00007f2ab83de340>
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PDB for #<Metabolite:0x00007f2ab83de340>
HEADER    PROTEIN                                 17-OCT-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-OCT-22         0                                  
HETATM    1  O   UNK     0       1.540   2.667   0.000  0.00  0.00           O-1
HETATM    2  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.850   1.334   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.540  -2.667   0.000  0.00  0.00           C+0
HETATM    7  S   UNK     0       2.310  -4.001   0.000  0.00  0.00           S+0
HETATM    8  N   UNK     0       3.080  -5.335   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0       0.976  -4.771   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.644  -3.231   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+1
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7                                                            
CONECT   11    4                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END

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3D PDB for #<Metabolite:0x00007f2ab83de340>
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SMILES for #<Metabolite:0x00007f2ab83de340>
CS(=N)(=O)CC[C@H]([NH3+])C([O-])=O
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INCHI for #<Metabolite:0x00007f2ab83de340>
InChI=1S/C5H12N2O3S/c1-11(7,10)3-2-4(6)5(8)9/h4,7H,2-3,6H2,1H3,(H,8,9)/t4-,11?/m0/s1
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Synonyms
ValueSource
(2S)-2-Amino-4-(S-methylsufonimidoyl)-butanoic acidKegg
(2S)-2-Amino-4-(S-methylsufonimidoyl)-butanoateGenerator
L-Methionine sulphoximineGenerator
Molecular FormulaC5H12N2O3S
Average Mass180.22
Monoisotopic Mass180.056863428
IUPAC Name(2S)-2-azaniumyl-4-[imino(methyl)oxo-lambda6-sulfanyl]butanoate
Traditional Name(2S)-2-ammonio-4-[imino(methyl)oxo-lambda6-sulfanyl]butanoate
CAS Registry NumberNot Available
SMILES
CS(=N)(=O)CC[C@H]([NH3+])C([O-])=O
InChI Identifier
InChI=1S/C5H12N2O3S/c1-11(7,10)3-2-4(6)5(8)9/h4,7H,2-3,6H2,1H3,(H,8,9)/t4-,11?/m0/s1
InChI KeySXTAYKAGBXMACB-DPVSGNNYSA-N