Np mrd loader

Showing NP-Card for DL-Methionine sulfoxide (NP0002724)

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Record Information
Version2.0
Created at2020-11-23 19:38:51 UTC
Updated at2021-08-12 19:51:58 UTC
NP-MRD IDNP0002724
Secondary Accession NumbersNone
Natural Product Identification
Common NameDL-Methionine sulfoxide
Provided ByBMRBBMRB logo
Description Based on a literature review very few articles have been published on L-methionine (R)-S-oxide.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002724 (DL-Methionine sulfoxide)


     RDKit          2D

 21 20  0  0  0  0  0  0  0  0999 V2000
   -3.4588   -0.0016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2962    0.9463    0.0000 S   0  0  0  0  0  4  0  0  0  0  0  0
   -2.5359    2.4271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8941    0.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5081   -0.1194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9102   -0.6523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3774   -2.0544    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4431    0.7499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6440    2.0193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9238    0.9895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4067    1.1610    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5109   -1.1641    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6214   -0.9494    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4270   -0.9887    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3612    1.8156    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8660    1.3372    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1917   -1.4462    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3124   -1.1851    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3252   -3.2170    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0631   -2.4728    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4567    2.3916    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  2  0
  2  4  1  1
  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  6
  1 12  1  0
  1 13  1  0
  4 14  1  1
  4 15  1  0
  5 16  1  1
  5 17  1  0
  6 18  1  6
  7 19  1  0
  7 20  1  0
 10 21  1  0
M  END
Download

3D MOL for NP0002724 (DL-Methionine sulfoxide)

NP0002724
     RDKit          3D

 21 20  0  0  0  0  0  0  0  0999 V2000
    2.7442    0.2772   -0.4538 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5704   -1.1377   -0.6284 S   0  0  0  0  0  4  0  0  0  0  0  0
    2.4824   -2.3195   -0.1602 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4835   -0.9421    0.8291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2149    0.3850    0.7900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0842    0.5789   -0.4330 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6678    1.9221   -0.2795 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2295   -0.3623   -0.4387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4386    0.0086   -0.3159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0227   -1.7259   -0.5828 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6618    0.0655   -1.0412 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0566    0.3618    0.6040 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2798    1.1765   -0.8634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2321   -1.7589    0.9076 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0972   -0.9549    1.7545 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5140    1.1836    0.9269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9055    0.4031    1.6653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5384    0.5381   -1.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8643    2.0582    0.7363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9924    2.6565   -0.5522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6997   -2.4140   -0.3134 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  2  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
  4 14  1  0
  4 15  1  0
  5 16  1  0
  5 17  1  0
  6 18  1  6
  7 19  1  0
  7 20  1  0
 10 21  1  0
M  END
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3D SDF for NP0002724 (DL-Methionine sulfoxide)


     RDKit          2D

 21 20  0  0  0  0  0  0  0  0999 V2000
   -3.4588   -0.0016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2962    0.9463    0.0000 S   0  0  0  0  0  4  0  0  0  0  0  0
   -2.5359    2.4271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8941    0.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5081   -0.1194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9102   -0.6523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3774   -2.0544    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4431    0.7499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6440    2.0193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9238    0.9895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4067    1.1610    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5109   -1.1641    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6214   -0.9494    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4270   -0.9887    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3612    1.8156    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8660    1.3372    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1917   -1.4462    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3124   -1.1851    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3252   -3.2170    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0631   -2.4728    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4567    2.3916    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  2  0
  2  4  1  1
  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  6
  1 12  1  0
  1 13  1  0
  4 14  1  1
  4 15  1  0
  5 16  1  1
  5 17  1  0
  6 18  1  6
  7 19  1  0
  7 20  1  0
 10 21  1  0
M  END
> <DATABASE_ID>
NP0002724

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[S@@](=O)CC[C@H](N)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H11NO3S/c1-10(9)3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-,10+/m0/s1

> <INCHI_KEY>
QEFRNWWLZKMPFJ-ZXPFJRLXSA-N

> <FORMULA>
C5H11NO3S

> <MOLECULAR_WEIGHT>
165.211

> <EXACT_MASS>
165.045963913

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
16.081881699764196

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-4-[(R)-methanesulfinyl]butanoic acid

> <ALOGPS_LOGP>
-2.40

> <JCHEM_LOGP>
-4.565261464903274

> <ALOGPS_LOGS>
-0.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7416965946301604

> <JCHEM_PKA_STRONGEST_BASIC>
9.11365628931558

> <JCHEM_POLAR_SURFACE_AREA>
80.38999999999999

> <JCHEM_REFRACTIVITY>
39.3427

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.40e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
L-methionine (R)-S-oxide

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0002724 (DL-Methionine sulfoxide)

NP0002724
     RDKit          3D

 21 20  0  0  0  0  0  0  0  0999 V2000
    2.7442    0.2772   -0.4538 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5704   -1.1377   -0.6284 S   0  0  0  0  0  4  0  0  0  0  0  0
    2.4824   -2.3195   -0.1602 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4835   -0.9421    0.8291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2149    0.3850    0.7900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0842    0.5789   -0.4330 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6678    1.9221   -0.2795 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2295   -0.3623   -0.4387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4386    0.0086   -0.3159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0227   -1.7259   -0.5828 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6618    0.0655   -1.0412 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0566    0.3618    0.6040 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2798    1.1765   -0.8634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2321   -1.7589    0.9076 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0972   -0.9549    1.7545 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5140    1.1836    0.9269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9055    0.4031    1.6653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5384    0.5381   -1.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8643    2.0582    0.7363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9924    2.6565   -0.5522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6997   -2.4140   -0.3134 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  2  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
  4 14  1  0
  4 15  1  0
  5 16  1  0
  5 17  1  0
  6 18  1  6
  7 19  1  0
  7 20  1  0
 10 21  1  0
M  END
Download

PDB for NP0002724 (DL-Methionine sulfoxide)

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       4.001  -0.330   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667   0.440   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.330   0.000  0.00  0.00           C+0
HETATM    4  S   UNK     0      -2.667   0.440   0.000  0.00  0.00           S+0
HETATM    5  C   UNK     0       0.000   0.440   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -0.330   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001  -0.330   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.667   1.980   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0       1.334  -1.870   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0      -2.667   1.980   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    8    3                                                  
CONECT    3    2    9    5                                                  
CONECT    4   10    6    7                                                  
CONECT    5    3    6                                                       
CONECT    6    5    4                                                       
CONECT    7    4                                                            
CONECT    8    2                                                            
CONECT    9    3                                                            
CONECT   10    4                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
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3D PDB for NP0002724 (DL-Methionine sulfoxide)

COMPND    NP0002724
HETATM    1  C1  UNL     1       2.744   0.277  -0.454  1.00  0.00           C  
HETATM    2  S1  UNL     1       1.570  -1.138  -0.628  1.00  0.00           S  
HETATM    3  O1  UNL     1       2.482  -2.319  -0.160  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.483  -0.942   0.829  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.215   0.385   0.790  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.084   0.579  -0.433  1.00  0.00           C  
HETATM    7  N1  UNL     1      -1.668   1.922  -0.280  1.00  0.00           N  
HETATM    8  C5  UNL     1      -2.229  -0.362  -0.439  1.00  0.00           C  
HETATM    9  O2  UNL     1      -3.439   0.009  -0.316  1.00  0.00           O  
HETATM   10  O3  UNL     1      -2.023  -1.726  -0.583  1.00  0.00           O  
HETATM   11  H1  UNL     1       3.662   0.066  -1.041  1.00  0.00           H  
HETATM   12  H2  UNL     1       3.057   0.362   0.604  1.00  0.00           H  
HETATM   13  H3  UNL     1       2.280   1.177  -0.863  1.00  0.00           H  
HETATM   14  H4  UNL     1      -0.232  -1.759   0.908  1.00  0.00           H  
HETATM   15  H5  UNL     1       1.097  -0.955   1.754  1.00  0.00           H  
HETATM   16  H6  UNL     1       0.514   1.184   0.927  1.00  0.00           H  
HETATM   17  H7  UNL     1      -0.905   0.403   1.665  1.00  0.00           H  
HETATM   18  H8  UNL     1      -0.538   0.538  -1.374  1.00  0.00           H  
HETATM   19  H9  UNL     1      -1.864   2.058   0.736  1.00  0.00           H  
HETATM   20  H10 UNL     1      -0.992   2.656  -0.552  1.00  0.00           H  
HETATM   21  H11 UNL     1      -2.700  -2.414  -0.313  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3    3    4
CONECT    4    5   14   15
CONECT    5    6   16   17
CONECT    6    7    8   18
CONECT    7   19   20
CONECT    8    9    9   10
CONECT   10   21
END
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SMILES for NP0002724 (DL-Methionine sulfoxide)

C[S@@](=O)CC[C@H](N)C(O)=O
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INCHI for NP0002724 (DL-Methionine sulfoxide)

InChI=1S/C5H11NO3S/c1-10(9)3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-,10+/m0/s1
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View in JSmol
Synonyms
ValueSource
L-Methionine-R-sulfoxideMetaCyc
L-Methionine-R-sulphoxideGenerator
Methionine sulfoxide, (+-)-isomerMeSH
Methionine sulfoxide, (2R)-isomerMeSH
Methionine sulfoxide, (2S)-isomerMeSH
Methionine sulfoxide, (S-(r*,s*))-isomerMeSH
Methionine sulfoxide, 35S-labeled, (+-)-isomerMeSH
Methionine sulfoxideMeSH
Methionine sulfoxide, (R-(r*,s*))-isomerMeSH
Chemical FormulaC5H11NO3S
Average Mass165.2110 Da
Monoisotopic Mass165.04596 Da
IUPAC Name(2S)-2-amino-4-[(R)-methanesulfinyl]butanoic acid
Traditional NameL-methionine (R)-S-oxide
CAS Registry NumberNot Available
SMILES
C[S@@](=O)CC[C@H](N)C(O)=O
InChI Identifier
InChI=1S/C5H11NO3S/c1-10(9)3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-,10+/m0/s1
InChI KeyQEFRNWWLZKMPFJ-ZXPFJRLXSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Thia fatty acid
  • Fatty acid
  • Fatty acyl
  • Sulfoxide
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Sulfinyl compound
  • Carbonyl group
  • Organic oxygen compound
  • Organic nitrogen compound
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Primary aliphatic amine
  • Organopnictogen 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-2.4ALOGPS
logP-4.6ChemAxon
logS-0.49ALOGPS
pKa (Strongest Acidic)1.74ChemAxon
pKa (Strongest Basic)9.11ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area80.39 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity39.34 m³·mol⁻¹ChemAxon
Polarizability16.08 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDDB02235
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID8238279
KEGG Compound IDC15998
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID49032
Good Scents IDNot Available
References
General References