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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-08-31 15:25:20 UTC

Update Date

2021-09-26 22:48:58 UTC

HMDB ID

HMDB0242473

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(2-Mercaptomethyl-3-phenyl-propionyl)-glycine

Description

(2-Mercaptomethyl-3-phenyl-propionyl)-glycine, also known as tiorphan, belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. Based on a literature review very few articles have been published on (2-Mercaptomethyl-3-phenyl-propionyl)-glycine. This compound has been identified in human blood as reported by (PMID: 31557052 ). (2-mercaptomethyl-3-phenyl-propionyl)-glycine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (2-Mercaptomethyl-3-phenyl-propionyl)-glycine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0242473
     RDKit          3D
(2-Mercaptomethyl-3-phenyl-propionyl)-glycine
 32 32  0  0  0  0  0  0  0  0999 V2000
    3.9772    1.3807   -0.3279 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5149    0.3088    0.0070 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8876    0.1721   -0.0477 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6933   -0.8232    0.4644 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2945   -0.4028    0.4200 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7224   -0.0022   -0.8081 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3355    0.0178   -1.8704 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2790    0.4179   -0.7798 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2166    1.5907    0.1630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4158    2.3048    0.3528 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4507   -0.7939   -0.2788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9003   -0.6712   -0.1414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7853   -0.8921   -1.1962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1494   -0.7879   -1.0224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6989   -0.4615    0.1983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8351   -0.2407    1.2492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4621   -0.3460    1.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3579   -0.0919    0.8066 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7667   -1.7060   -0.2082 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9816   -1.1877    1.4714 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7875   -0.4232    1.3178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0506    0.7169   -1.8016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6343    1.2360    1.1521 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9783    2.3575   -0.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3014    3.7037    0.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0369   -1.0740    0.7162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2718   -1.6708   -0.9679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3679   -1.1462   -2.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8411   -0.9578   -1.8355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7727   -0.3761    0.3483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2687    0.0179    2.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8188   -0.1700    1.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  8 22  1  0
  9 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 11 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
M  END

 
  Mrv1533006081517592D          
 
 17 17  0  0  0  0            999 V2000
    7.4250  -11.2612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250  -12.0862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1394  -12.4987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8540  -12.0862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8540  -11.2612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1394  -10.8487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5832  -10.8487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2977  -11.2612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0122  -10.8487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7266  -11.2612    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4411  -10.8487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1556  -11.2612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8700  -10.8487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2977  -12.0861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0232  -12.5051    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.0122  -10.0237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1556  -12.0862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
  9 16  2  0  0  0  0
 12 17  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0242473

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)CNC(=O)C(CS)CC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H15NO3S/c14-11(15)7-13-12(16)10(8-17)6-9-4-2-1-3-5-9/h1-5,10,17H,6-8H2,(H,13,16)(H,14,15)

> <INCHI_KEY>
LJJKNPQAGWVLDQ-UHFFFAOYSA-N

> <FORMULA>
C12H15NO3S

> <MOLECULAR_WEIGHT>
253.32

> <EXACT_MASS>
253.077264521

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
25.965517350035885

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(2-benzyl-3-sulfanylpropanamido)acetic acid

> <ALOGPS_LOGP>
1.78

> <JCHEM_LOGP>
1.463864048333333

> <ALOGPS_LOGS>
-2.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.090626719633372

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.017451249075989

> <JCHEM_PKA_STRONGEST_BASIC>
-2.0943681882024494

> <JCHEM_POLAR_SURFACE_AREA>
66.4

> <JCHEM_REFRACTIVITY>
67.14789999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.45e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
thiorphan

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0242473
     RDKit          3D
(2-Mercaptomethyl-3-phenyl-propionyl)-glycine
 32 32  0  0  0  0  0  0  0  0999 V2000
    3.9772    1.3807   -0.3279 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5149    0.3088    0.0070 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8876    0.1721   -0.0477 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6933   -0.8232    0.4644 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2945   -0.4028    0.4200 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7224   -0.0022   -0.8081 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3355    0.0178   -1.8704 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2790    0.4179   -0.7798 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2166    1.5907    0.1630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4158    2.3048    0.3528 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4507   -0.7939   -0.2788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9003   -0.6712   -0.1414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7853   -0.8921   -1.1962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1494   -0.7879   -1.0224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6989   -0.4615    0.1983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8351   -0.2407    1.2492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4621   -0.3460    1.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3579   -0.0919    0.8066 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7667   -1.7060   -0.2082 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9816   -1.1877    1.4714 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7875   -0.4232    1.3178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0506    0.7169   -1.8016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6343    1.2360    1.1521 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9783    2.3575   -0.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3014    3.7037    0.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0369   -1.0740    0.7162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2718   -1.6708   -0.9679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3679   -1.1462   -2.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8411   -0.9578   -1.8355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7727   -0.3761    0.3483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2687    0.0179    2.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8188   -0.1700    1.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  8 22  1  0
  9 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 11 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
M  END

HEADER    PROTEIN                                 08-JUN-15   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-JUN-15         0                                  
HETATM    1  C   UNK     0      13.860 -21.021   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.860 -22.561   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.194 -23.331   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.527 -22.561   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.527 -21.021   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.194 -20.251   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.889 -20.251   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      19.222 -21.021   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      20.556 -20.251   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      21.890 -21.021   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      23.223 -20.251   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      24.557 -21.021   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      25.891 -20.251   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      19.222 -22.561   0.000  0.00  0.00           C+0
HETATM   15  S   UNK     0      20.577 -23.343   0.000  0.00  0.00           S+0
HETATM   16  O   UNK     0      20.556 -18.711   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      24.557 -22.561   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12                                                            
CONECT   14    8   15                                                       
CONECT   15   14                                                            
CONECT   16    9                                                            
CONECT   17   12                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0242473
HETATM    1  O1  UNL     1       3.977   1.381  -0.328  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.515   0.309   0.007  1.00  0.00           C  
HETATM    3  O2  UNL     1       5.888   0.172  -0.048  1.00  0.00           O  
HETATM    4  C2  UNL     1       3.693  -0.823   0.464  1.00  0.00           C  
HETATM    5  N1  UNL     1       2.295  -0.403   0.420  1.00  0.00           N  
HETATM    6  C3  UNL     1       1.722  -0.002  -0.808  1.00  0.00           C  
HETATM    7  O3  UNL     1       2.336   0.018  -1.870  1.00  0.00           O  
HETATM    8  C4  UNL     1       0.279   0.418  -0.780  1.00  0.00           C  
HETATM    9  C5  UNL     1       0.217   1.591   0.163  1.00  0.00           C  
HETATM   10  S1  UNL     1      -1.416   2.305   0.353  1.00  0.00           S  
HETATM   11  C6  UNL     1      -0.451  -0.794  -0.279  1.00  0.00           C  
HETATM   12  C7  UNL     1      -1.900  -0.671  -0.141  1.00  0.00           C  
HETATM   13  C8  UNL     1      -2.785  -0.892  -1.196  1.00  0.00           C  
HETATM   14  C9  UNL     1      -4.149  -0.788  -1.022  1.00  0.00           C  
HETATM   15  C10 UNL     1      -4.699  -0.461   0.198  1.00  0.00           C  
HETATM   16  C11 UNL     1      -3.835  -0.241   1.249  1.00  0.00           C  
HETATM   17  C12 UNL     1      -2.462  -0.346   1.073  1.00  0.00           C  
HETATM   18  H1  UNL     1       6.358  -0.092   0.807  1.00  0.00           H  
HETATM   19  H2  UNL     1       3.767  -1.706  -0.208  1.00  0.00           H  
HETATM   20  H3  UNL     1       3.982  -1.188   1.471  1.00  0.00           H  
HETATM   21  H4  UNL     1       1.788  -0.423   1.318  1.00  0.00           H  
HETATM   22  H5  UNL     1      -0.051   0.717  -1.802  1.00  0.00           H  
HETATM   23  H6  UNL     1       0.634   1.236   1.152  1.00  0.00           H  
HETATM   24  H7  UNL     1       0.978   2.358  -0.164  1.00  0.00           H  
HETATM   25  H8  UNL     1      -1.301   3.704   0.256  1.00  0.00           H  
HETATM   26  H9  UNL     1      -0.037  -1.074   0.716  1.00  0.00           H  
HETATM   27  H10 UNL     1      -0.272  -1.671  -0.968  1.00  0.00           H  
HETATM   28  H11 UNL     1      -2.368  -1.146  -2.148  1.00  0.00           H  
HETATM   29  H12 UNL     1      -4.841  -0.958  -1.835  1.00  0.00           H  
HETATM   30  H13 UNL     1      -5.773  -0.376   0.348  1.00  0.00           H  
HETATM   31  H14 UNL     1      -4.269   0.018   2.216  1.00  0.00           H  
HETATM   32  H15 UNL     1      -1.819  -0.170   1.933  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   18
CONECT    4    5   19   20
CONECT    5    6   21
CONECT    6    7    7    8
CONECT    8    9   11   22
CONECT    9   10   23   24
CONECT   10   25
CONECT   11   12   26   27
CONECT   12   13   13   17
CONECT   13   14   28
CONECT   14   15   15   29
CONECT   15   16   30
CONECT   16   17   17   31
CONECT   17   32
END

HMDB0242473
     RDKit          3D
(2-Mercaptomethyl-3-phenyl-propionyl)-glycine
 32 32  0  0  0  0  0  0  0  0999 V2000
    3.9772    1.3807   -0.3279 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5149    0.3088    0.0070 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8876    0.1721   -0.0477 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6933   -0.8232    0.4644 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2945   -0.4028    0.4200 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7224   -0.0022   -0.8081 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3355    0.0178   -1.8704 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2790    0.4179   -0.7798 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2166    1.5907    0.1630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4158    2.3048    0.3528 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4507   -0.7939   -0.2788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9003   -0.6712   -0.1414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7853   -0.8921   -1.1962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1494   -0.7879   -1.0224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6989   -0.4615    0.1983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8351   -0.2407    1.2492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4621   -0.3460    1.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3579   -0.0919    0.8066 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7667   -1.7060   -0.2082 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9816   -1.1877    1.4714 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7875   -0.4232    1.3178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0506    0.7169   -1.8016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6343    1.2360    1.1521 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9783    2.3575   -0.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3014    3.7037    0.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0369   -1.0740    0.7162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2718   -1.6708   -0.9679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3679   -1.1462   -2.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8411   -0.9578   -1.8355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7727   -0.3761    0.3483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2687    0.0179    2.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8188   -0.1700    1.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  8 22  1  0
  9 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 11 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Thiorphan, (R)-isomer	HMDB
(3-Mercapto-2-benzylpropionyl)glycine	HMDB
Thiorphan, (S)-isomer	HMDB
Tiorphan	HMDB

Chemical Formula

C₁₂H₁₅NO₃S

Average Molecular Weight

253.32

Monoisotopic Molecular Weight

253.077264521

IUPAC Name

2-(2-benzyl-3-sulfanylpropanamido)acetic acid

Traditional Name

thiorphan

CAS Registry Number

Not Available

SMILES

OC(=O)CNC(=O)C(CS)CC1=CC=CC=C1

InChI Identifier

InChI=1S/C12H15NO3S/c14-11(15)7-13-12(16)10(8-17)6-9-4-2-1-3-5-9/h1-5,10,17H,6-8H2,(H,13,16)(H,14,15)

InChI Key

LJJKNPQAGWVLDQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids

Alternative Parents

Substituents

N-acyl-alpha-amino acid
Monocyclic benzene moiety
Fatty amide
Fatty acyl
Benzenoid
Carboxamide group
Secondary carboxylic acid amide
Alkylthiol
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organosulfur compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

N-acyl-amino acid (CHEBI:9568 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	1.78	ALOGPS
logP	1.46	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	4.02	ChemAxon
pKa (Strongest Basic)	-2.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	66.4 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	67.15 m³·mol⁻¹	ChemAxon
Polarizability	25.97 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	159.248	30932474
DeepCCS	[M-H]-	156.89	30932474
DeepCCS	[M-2H]-	190.132	30932474
DeepCCS	[M+Na]+	165.341	30932474
AllCCS	[M+H]+	155.0	32859911
AllCCS	[M+H-H2O]+	151.5	32859911
AllCCS	[M+NH4]+	158.3	32859911
AllCCS	[M+Na]+	159.2	32859911
AllCCS	[M-H]-	157.7	32859911
AllCCS	[M+Na-2H]-	158.1	32859911
AllCCS	[M+HCOO]-	158.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(2-Mercaptomethyl-3-phenyl-propionyl)-glycine	OC(=O)CNC(=O)C(CS)CC1=CC=CC=C1	3705.9	Standard polar	33892256
(2-Mercaptomethyl-3-phenyl-propionyl)-glycine	OC(=O)CNC(=O)C(CS)CC1=CC=CC=C1	1950.0	Standard non polar	33892256
(2-Mercaptomethyl-3-phenyl-propionyl)-glycine	OC(=O)CNC(=O)C(CS)CC1=CC=CC=C1	2262.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(2-Mercaptomethyl-3-phenyl-propionyl)-glycine,2TMS,isomer #1	C[Si](C)(C)OC(=O)CNC(=O)C(CS[Si](C)(C)C)CC1=CC=CC=C1	2333.4	Semi standard non polar	33892256
(2-Mercaptomethyl-3-phenyl-propionyl)-glycine,2TMS,isomer #1	C[Si](C)(C)OC(=O)CNC(=O)C(CS[Si](C)(C)C)CC1=CC=CC=C1	2328.1	Standard non polar	33892256
(2-Mercaptomethyl-3-phenyl-propionyl)-glycine,2TMS,isomer #1	C[Si](C)(C)OC(=O)CNC(=O)C(CS[Si](C)(C)C)CC1=CC=CC=C1	2849.5	Standard polar	33892256
(2-Mercaptomethyl-3-phenyl-propionyl)-glycine,2TMS,isomer #2	C[Si](C)(C)OC(=O)CN(C(=O)C(CS)CC1=CC=CC=C1)[Si](C)(C)C	2235.2	Semi standard non polar	33892256
(2-Mercaptomethyl-3-phenyl-propionyl)-glycine,2TMS,isomer #2	C[Si](C)(C)OC(=O)CN(C(=O)C(CS)CC1=CC=CC=C1)[Si](C)(C)C	2220.6	Standard non polar	33892256
(2-Mercaptomethyl-3-phenyl-propionyl)-glycine,2TMS,isomer #2	C[Si](C)(C)OC(=O)CN(C(=O)C(CS)CC1=CC=CC=C1)[Si](C)(C)C	2786.7	Standard polar	33892256
(2-Mercaptomethyl-3-phenyl-propionyl)-glycine,2TMS,isomer #3	C[Si](C)(C)SCC(CC1=CC=CC=C1)C(=O)N(CC(=O)O)[Si](C)(C)C	2368.0	Semi standard non polar	33892256
(2-Mercaptomethyl-3-phenyl-propionyl)-glycine,2TMS,isomer #3	C[Si](C)(C)SCC(CC1=CC=CC=C1)C(=O)N(CC(=O)O)[Si](C)(C)C	2361.6	Standard non polar	33892256
(2-Mercaptomethyl-3-phenyl-propionyl)-glycine,2TMS,isomer #3	C[Si](C)(C)SCC(CC1=CC=CC=C1)C(=O)N(CC(=O)O)[Si](C)(C)C	2899.2	Standard polar	33892256
(2-Mercaptomethyl-3-phenyl-propionyl)-glycine,3TMS,isomer #1	C[Si](C)(C)OC(=O)CN(C(=O)C(CS[Si](C)(C)C)CC1=CC=CC=C1)[Si](C)(C)C	2326.8	Semi standard non polar	33892256
(2-Mercaptomethyl-3-phenyl-propionyl)-glycine,3TMS,isomer #1	C[Si](C)(C)OC(=O)CN(C(=O)C(CS[Si](C)(C)C)CC1=CC=CC=C1)[Si](C)(C)C	2374.3	Standard non polar	33892256
(2-Mercaptomethyl-3-phenyl-propionyl)-glycine,3TMS,isomer #1	C[Si](C)(C)OC(=O)CN(C(=O)C(CS[Si](C)(C)C)CC1=CC=CC=C1)[Si](C)(C)C	2668.8	Standard polar	33892256
(2-Mercaptomethyl-3-phenyl-propionyl)-glycine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CNC(=O)C(CS[Si](C)(C)C(C)(C)C)CC1=CC=CC=C1	2820.0	Semi standard non polar	33892256
(2-Mercaptomethyl-3-phenyl-propionyl)-glycine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CNC(=O)C(CS[Si](C)(C)C(C)(C)C)CC1=CC=CC=C1	2752.1	Standard non polar	33892256
(2-Mercaptomethyl-3-phenyl-propionyl)-glycine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CNC(=O)C(CS[Si](C)(C)C(C)(C)C)CC1=CC=CC=C1	3020.9	Standard polar	33892256
(2-Mercaptomethyl-3-phenyl-propionyl)-glycine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)C(CS)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2734.1	Semi standard non polar	33892256
(2-Mercaptomethyl-3-phenyl-propionyl)-glycine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)C(CS)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2649.7	Standard non polar	33892256
(2-Mercaptomethyl-3-phenyl-propionyl)-glycine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)C(CS)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2944.2	Standard polar	33892256
(2-Mercaptomethyl-3-phenyl-propionyl)-glycine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)SCC(CC1=CC=CC=C1)C(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C	2872.0	Semi standard non polar	33892256
(2-Mercaptomethyl-3-phenyl-propionyl)-glycine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)SCC(CC1=CC=CC=C1)C(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C	2758.6	Standard non polar	33892256
(2-Mercaptomethyl-3-phenyl-propionyl)-glycine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)SCC(CC1=CC=CC=C1)C(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C	3063.6	Standard polar	33892256
(2-Mercaptomethyl-3-phenyl-propionyl)-glycine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)C(CS[Si](C)(C)C(C)(C)C)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	3060.1	Semi standard non polar	33892256
(2-Mercaptomethyl-3-phenyl-propionyl)-glycine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)C(CS[Si](C)(C)C(C)(C)C)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2983.2	Standard non polar	33892256
(2-Mercaptomethyl-3-phenyl-propionyl)-glycine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)C(CS[Si](C)(C)C(C)(C)C)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2965.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (2-Mercaptomethyl-3-phenyl-propionyl)-glycine GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-9620000000-5619049cb531f9396a14	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2-Mercaptomethyl-3-phenyl-propionyl)-glycine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2-Mercaptomethyl-3-phenyl-propionyl)-glycine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2-Mercaptomethyl-3-phenyl-propionyl)-glycine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2-Mercaptomethyl-3-phenyl-propionyl)-glycine GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2-Mercaptomethyl-3-phenyl-propionyl)-glycine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2-Mercaptomethyl-3-phenyl-propionyl)-glycine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2-Mercaptomethyl-3-phenyl-propionyl)-glycine GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2-Mercaptomethyl-3-phenyl-propionyl)-glycine 10V, Positive-QTOF	splash10-0udl-5950000000-057a22c66a0d65dfea4d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2-Mercaptomethyl-3-phenyl-propionyl)-glycine 20V, Positive-QTOF	splash10-0006-8930000000-bc1b636ae299d9601168	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2-Mercaptomethyl-3-phenyl-propionyl)-glycine 40V, Positive-QTOF	splash10-0006-9700000000-5683b056040e9b71c9a6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2-Mercaptomethyl-3-phenyl-propionyl)-glycine 10V, Negative-QTOF	splash10-0udi-0090000000-909e46a071ae18ea6ecd	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2-Mercaptomethyl-3-phenyl-propionyl)-glycine 20V, Negative-QTOF	splash10-007o-8930000000-07dfcd864faa651ce936	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2-Mercaptomethyl-3-phenyl-propionyl)-glycine 40V, Negative-QTOF	splash10-0536-9300000000-a2936ef0a2f171702dd9	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3020

KEGG Compound ID

C01619

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Thiorphan

METLIN ID

Not Available

PubChem Compound

3132

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for (2-Mercaptomethyl-3-phenyl-propionyl)-glycine (HMDB0242473)

MOL for HMDB0242473 ((2-Mercaptomethyl-3-phenyl-propionyl)-glycine)

3D MOL for HMDB0242473 ((2-Mercaptomethyl-3-phenyl-propionyl)-glycine)

3D SDF for HMDB0242473 ((2-Mercaptomethyl-3-phenyl-propionyl)-glycine)

3D-SDF for HMDB0242473 ((2-Mercaptomethyl-3-phenyl-propionyl)-glycine)

PDB for HMDB0242473 ((2-Mercaptomethyl-3-phenyl-propionyl)-glycine)

3D PDB for HMDB0242473 ((2-Mercaptomethyl-3-phenyl-propionyl)-glycine)

SMILES for HMDB0242473 ((2-Mercaptomethyl-3-phenyl-propionyl)-glycine)

INCHI for HMDB0242473 ((2-Mercaptomethyl-3-phenyl-propionyl)-glycine)

Structure for HMDB0242473 ((2-Mercaptomethyl-3-phenyl-propionyl)-glycine)

3D Structure for HMDB0242473 ((2-Mercaptomethyl-3-phenyl-propionyl)-glycine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra