MiMeDB: Showing metabocard for S-(Hydroxymethyl)glutathione (MMDBc0029822)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:43:09 UTC

Update Date

2024-10-11 01:23:24 UTC

Metabolite ID

MMDBc0029822

Metabolite Identification

Common Name

S-(Hydroxymethyl)glutathione

Description

S-Hydroxymethylglutathione is a critical component of the binding site for activating fatty acids in glutathione-dependent formaldehyde dehydrogenase activity. (OMIM 103710 )

Structure

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

HMDB0004662
     RDKit          3D
S-Hydroxymethylglutathione
 41 40  0  0  0  0  0  0  0  0999 V2000
    3.1237    0.5973    1.4968 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9915    0.3346    0.3436 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3975    0.7706   -0.9292 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2238    0.0635   -1.4485 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0663   -0.1881   -0.6351 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1179   -0.2003    0.5790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2094   -0.4663   -1.2654 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3580   -0.8702   -0.5674 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0914   -1.9739    0.4797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6865   -2.5100    1.1828 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5171   -3.4970   -0.1290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8219   -2.7530   -1.2431 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3128    0.1287   -0.1245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5131    0.1189   -0.5046 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9748    1.1771    0.7563 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9317    2.0888    1.2913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9003    2.7154    0.3077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4811    2.5283   -0.5662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9579    4.1696    0.9136 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3713    0.8540    0.5715 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7251    1.5378    1.5260 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3322    0.5075   -0.4164 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9702    1.6460    1.4728 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6165    0.3630    2.4127 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1195   -0.7961    0.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2362    0.6875   -1.7093 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1668    1.8709   -0.9309 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9088    0.4721   -2.4678 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6534   -0.9829   -1.8053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2607   -0.3332   -2.2929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9452   -1.4847   -1.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4132   -1.7027    1.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6177   -2.8096   -0.1058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4107   -4.0333    0.2743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7846   -4.2978   -0.3672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6352   -3.1935   -2.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9657    1.3400    1.0373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3525    2.8724    1.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5798    1.5528    2.0303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5378    4.1166    1.7606 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2384   -0.4214   -0.8619 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  8 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
  2 20  1  0
 20 21  2  0
 20 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  6
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  7 30  1  0
  8 31  1  6
  9 32  1  0
  9 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 19 40  1  0
 22 41  1  0
M  END


  Mrv1652309042000312D          

 22 21  0  0  1  0            999 V2000
   24.6614  -19.3585    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   23.9470  -20.5960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3745  -17.7085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.9483  -17.7085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0891  -18.9461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.2338  -18.9461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.0903  -16.8836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9470  -18.9461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.6614  -17.7085    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.8049  -18.1210    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.8035  -16.8836    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.8035  -17.7085    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   25.3759  -18.1210    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   24.6614  -20.1836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3759  -18.9461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5180  -18.1210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5193  -17.7085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2324  -17.7085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0891  -18.1210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2338  -18.1210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0903  -17.7085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9470  -18.1210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 14  1  0  0  0  0
  1 15  1  0  0  0  0
  2 14  1  0  0  0  0
  3 19  1  0  0  0  0
  4 20  1  0  0  0  0
  5 19  2  0  0  0  0
  6 20  2  0  0  0  0
  7 21  2  0  0  0  0
  8 22  2  0  0  0  0
 13  9  1  6  0  0  0
  9 22  1  0  0  0  0
 10 17  1  0  0  0  0
 10 21  1  0  0  0  0
 12 11  1  1  0  0  0
 12 16  1  0  0  0  0
 12 19  1  0  0  0  0
 13 15  1  0  0  0  0
 13 21  1  0  0  0  0
 16 18  1  0  0  0  0
 17 20  1  0  0  0  0
 18 22  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029822

> <DATABASE_NAME>
MIME

> <SMILES>
N[C@@H](CCC(=O)N[C@@H](CSCO)C(=O)NCC(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H19N3O7S/c12-6(11(20)21)1-2-8(16)14-7(4-22-5-15)10(19)13-3-9(17)18/h6-7,15H,1-5,12H2,(H,13,19)(H,14,16)(H,17,18)(H,20,21)/t6-,7-/m0/s1

> <INCHI_KEY>
PIUSLWSYOYFRFR-BQBZGAKWSA-N

> <FORMULA>
C11H19N3O7S

> <MOLECULAR_WEIGHT>
337.349

> <EXACT_MASS>
337.094370667

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
32.23239927663239

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-[(hydroxymethyl)sulfanyl]ethyl]carbamoyl}butanoic acid

> <ALOGPS_LOGP>
-3.16

> <JCHEM_LOGP>
-5.546883718643985

> <ALOGPS_LOGS>
-1.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.6667948135698616

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7902878525377846

> <JCHEM_PKA_STRONGEST_BASIC>
9.311248246554086

> <JCHEM_POLAR_SURFACE_AREA>
179.04999999999998

> <JCHEM_REFRACTIVITY>
75.20209999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.27e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
S-hydroxymethylglutathione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0004662
     RDKit          3D
S-Hydroxymethylglutathione
 41 40  0  0  0  0  0  0  0  0999 V2000
    3.1237    0.5973    1.4968 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9915    0.3346    0.3436 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3975    0.7706   -0.9292 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2238    0.0635   -1.4485 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0663   -0.1881   -0.6351 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1179   -0.2003    0.5790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2094   -0.4663   -1.2654 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3580   -0.8702   -0.5674 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0914   -1.9739    0.4797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6865   -2.5100    1.1828 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5171   -3.4970   -0.1290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8219   -2.7530   -1.2431 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3128    0.1287   -0.1245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5131    0.1189   -0.5046 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9748    1.1771    0.7563 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9317    2.0888    1.2913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9003    2.7154    0.3077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4811    2.5283   -0.5662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9579    4.1696    0.9136 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3713    0.8540    0.5715 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7251    1.5378    1.5260 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3322    0.5075   -0.4164 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9702    1.6460    1.4728 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6165    0.3630    2.4127 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1195   -0.7961    0.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2362    0.6875   -1.7093 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1668    1.8709   -0.9309 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9088    0.4721   -2.4678 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6534   -0.9829   -1.8053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2607   -0.3332   -2.2929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9452   -1.4847   -1.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4132   -1.7027    1.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6177   -2.8096   -0.1058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4107   -4.0333    0.2743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7846   -4.2978   -0.3672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6352   -3.1935   -2.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9657    1.3400    1.0373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3525    2.8724    1.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5798    1.5528    2.0303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5378    4.1166    1.7606 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2384   -0.4214   -0.8619 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  8 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
  2 20  1  0
 20 21  2  0
 20 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  6
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  7 30  1  0
  8 31  1  6
  9 32  1  0
  9 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 19 40  1  0
 22 41  1  0
M  END

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  S   UNK     0      46.035 -36.136   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0      44.701 -38.446   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      38.032 -33.056   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      54.037 -33.056   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      39.366 -35.366   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      52.703 -35.366   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      48.702 -31.516   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      44.701 -35.366   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0      46.035 -33.056   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      50.036 -33.826   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0      40.700 -31.516   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      40.700 -33.056   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      47.368 -33.826   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      46.035 -37.676   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      47.368 -35.366   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      42.034 -33.826   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      51.369 -33.056   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      43.367 -33.056   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      39.366 -33.826   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      52.703 -33.826   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      48.702 -33.056   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      44.701 -33.826   0.000  0.00  0.00           C+0
CONECT    1   14   15                                                       
CONECT    2   14                                                            
CONECT    3   19                                                            
CONECT    4   20                                                            
CONECT    5   19                                                            
CONECT    6   20                                                            
CONECT    7   21                                                            
CONECT    8   22                                                            
CONECT    9   13   22                                                       
CONECT   10   17   21                                                       
CONECT   11   12                                                            
CONECT   12   11   16   19                                                  
CONECT   13    9   15   21                                                  
CONECT   14    1    2                                                       
CONECT   15    1   13                                                       
CONECT   16   12   18                                                       
CONECT   17   10   20                                                       
CONECT   18   16   22                                                       
CONECT   19    3    5   12                                                  
CONECT   20    4    6   17                                                  
CONECT   21    7   10   13                                                  
CONECT   22    8    9   18                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   42    0
END

COMPND    HMDB0004662
HETATM    1  N1  UNL     1       3.124   0.597   1.497  1.00  0.00           N  
HETATM    2  C1  UNL     1       3.992   0.335   0.344  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.398   0.771  -0.929  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.224   0.063  -1.449  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.066  -0.188  -0.635  1.00  0.00           C  
HETATM    6  O1  UNL     1       1.118  -0.200   0.579  1.00  0.00           O  
HETATM    7  N2  UNL     1      -0.209  -0.466  -1.265  1.00  0.00           N  
HETATM    8  C5  UNL     1      -1.358  -0.870  -0.567  1.00  0.00           C  
HETATM    9  C6  UNL     1      -1.091  -1.974   0.480  1.00  0.00           C  
HETATM   10  S1  UNL     1      -2.687  -2.510   1.183  1.00  0.00           S  
HETATM   11  C7  UNL     1      -3.517  -3.497  -0.129  1.00  0.00           C  
HETATM   12  O2  UNL     1      -3.822  -2.753  -1.243  1.00  0.00           O  
HETATM   13  C8  UNL     1      -2.313   0.129  -0.124  1.00  0.00           C  
HETATM   14  O3  UNL     1      -3.513   0.119  -0.505  1.00  0.00           O  
HETATM   15  N3  UNL     1      -1.975   1.177   0.756  1.00  0.00           N  
HETATM   16  C9  UNL     1      -2.932   2.089   1.291  1.00  0.00           C  
HETATM   17  C10 UNL     1      -3.900   2.715   0.308  1.00  0.00           C  
HETATM   18  O4  UNL     1      -4.481   2.528  -0.566  1.00  0.00           O  
HETATM   19  O5  UNL     1      -3.958   4.170   0.914  1.00  0.00           O  
HETATM   20  C11 UNL     1       5.371   0.854   0.571  1.00  0.00           C  
HETATM   21  O6  UNL     1       5.725   1.538   1.526  1.00  0.00           O  
HETATM   22  O7  UNL     1       6.332   0.508  -0.416  1.00  0.00           O  
HETATM   23  H1  UNL     1       2.970   1.646   1.473  1.00  0.00           H  
HETATM   24  H2  UNL     1       3.616   0.363   2.413  1.00  0.00           H  
HETATM   25  H3  UNL     1       4.120  -0.796   0.266  1.00  0.00           H  
HETATM   26  H4  UNL     1       4.236   0.688  -1.709  1.00  0.00           H  
HETATM   27  H5  UNL     1       3.167   1.871  -0.931  1.00  0.00           H  
HETATM   28  H6  UNL     1       1.909   0.472  -2.468  1.00  0.00           H  
HETATM   29  H7  UNL     1       2.653  -0.983  -1.805  1.00  0.00           H  
HETATM   30  H8  UNL     1      -0.261  -0.333  -2.293  1.00  0.00           H  
HETATM   31  H9  UNL     1      -1.945  -1.485  -1.374  1.00  0.00           H  
HETATM   32  H10 UNL     1      -0.413  -1.703   1.277  1.00  0.00           H  
HETATM   33  H11 UNL     1      -0.618  -2.810  -0.106  1.00  0.00           H  
HETATM   34  H12 UNL     1      -4.411  -4.033   0.274  1.00  0.00           H  
HETATM   35  H13 UNL     1      -2.785  -4.298  -0.367  1.00  0.00           H  
HETATM   36  H14 UNL     1      -3.635  -3.193  -2.088  1.00  0.00           H  
HETATM   37  H15 UNL     1      -0.966   1.340   1.037  1.00  0.00           H  
HETATM   38  H16 UNL     1      -2.353   2.872   1.852  1.00  0.00           H  
HETATM   39  H17 UNL     1      -3.580   1.553   2.030  1.00  0.00           H  
HETATM   40  H18 UNL     1      -4.538   4.117   1.761  1.00  0.00           H  
HETATM   41  H19 UNL     1       6.238  -0.421  -0.862  1.00  0.00           H  
CONECT    1    2   23   24
CONECT    2    3   20   25
CONECT    3    4   26   27
CONECT    4    5   28   29
CONECT    5    6    6    7
CONECT    7    8   30
CONECT    8    9   13   31
CONECT    9   10   32   33
CONECT   10   11
CONECT   11   12   34   35
CONECT   12   36
CONECT   13   14   14   15
CONECT   15   16   37
CONECT   16   17   38   39
CONECT   17   18   18   19
CONECT   19   40
CONECT   20   21   21   22
CONECT   22   41
END

HMDB0004662
     RDKit          3D
S-Hydroxymethylglutathione
 41 40  0  0  0  0  0  0  0  0999 V2000
    3.1237    0.5973    1.4968 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9915    0.3346    0.3436 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3975    0.7706   -0.9292 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2238    0.0635   -1.4485 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0663   -0.1881   -0.6351 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1179   -0.2003    0.5790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2094   -0.4663   -1.2654 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3580   -0.8702   -0.5674 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0914   -1.9739    0.4797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6865   -2.5100    1.1828 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5171   -3.4970   -0.1290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8219   -2.7530   -1.2431 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3128    0.1287   -0.1245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5131    0.1189   -0.5046 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9748    1.1771    0.7563 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9317    2.0888    1.2913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9003    2.7154    0.3077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4811    2.5283   -0.5662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9579    4.1696    0.9136 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3713    0.8540    0.5715 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7251    1.5378    1.5260 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3322    0.5075   -0.4164 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9702    1.6460    1.4728 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6165    0.3630    2.4127 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1195   -0.7961    0.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2362    0.6875   -1.7093 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1668    1.8709   -0.9309 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9088    0.4721   -2.4678 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6534   -0.9829   -1.8053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2607   -0.3332   -2.2929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9452   -1.4847   -1.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4132   -1.7027    1.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6177   -2.8096   -0.1058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4107   -4.0333    0.2743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7846   -4.2978   -0.3672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6352   -3.1935   -2.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9657    1.3400    1.0373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3525    2.8724    1.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5798    1.5528    2.0303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5378    4.1166    1.7606 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2384   -0.4214   -0.8619 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  8 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
  2 20  1  0
 20 21  2  0
 20 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  6
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  7 30  1  0
  8 31  1  6
  9 32  1  0
  9 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 19 40  1  0
 22 41  1  0
M  END

Synonyms

Value	Source
2-amino-4-[1-CARBOXYMETHYL-carbamoyl)-2-hydroxymethylsulfanyl-ethylcarbamoyl]-butyrIC ACID	ChEBI, HMDB
S-Hydroxymethylglutathione	ChEBI
2-amino-4-[1-CARBOXYMETHYL-carbamoyl)-2-hydroxymethylsulfanyl-ethylcarbamoyl]-butyrate	Generator, HMDB
2-amino-4-[1-CARBOXYMETHYL-carbamoyl)-2-hydroxymethylsulphanyl-ethylcarbamoyl]-butyrate	Generator, HMDB
2-amino-4-[1-CARBOXYMETHYL-carbamoyl)-2-hydroxymethylsulphanyl-ethylcarbamoyl]-butyric acid	Generator, HMDB
S-Hydroxymethyl-glutathione	HMDB
SerGSH	MeSH, HMDB
Formaldehyde-glutathione thiohemiacetal	HMDB
Glutathione-formaldehyde thiohemiacetal	HMDB
L-gamma-Glutamyl-S-(hydroxymethyl)-L-cysteinylglycine	HMDB
L-γ-Glutamyl-S-(hydroxymethyl)-L-cysteinylglycine	HMDB
S-(Hydroxymethyl)glutathione	HMDB

Molecular Formula

C₁₁H₁₉N₃O₇S

Average Mass

337.349

Monoisotopic Mass

337.094370667

IUPAC Name

(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-[(hydroxymethyl)sulfanyl]ethyl]carbamoyl}butanoic acid

Traditional Name

S-hydroxymethylglutathione

CAS Registry Number

32260-87-0

SMILES

N[C@@H](CCC(=O)N[C@@H](CSCO)C(=O)NCC(O)=O)C(O)=O

InChI Identifier

InChI=1S/C11H19N3O7S/c12-6(11(20)21)1-2-8(16)14-7(4-22-5-15)10(19)13-3-9(17)18/h6-7,15H,1-5,12H2,(H,13,19)(H,14,16)(H,17,18)(H,20,21)/t6-,7-/m0/s1

InChI Key

PIUSLWSYOYFRFR-BQBZGAKWSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

Alternative Parents

Substituents

Alpha-oligopeptide
Gamma-glutamyl alpha peptide
Glutamine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Cysteine or derivatives
Alpha-amino acid
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
L-alpha-amino acid
Dicarboxylic acid or derivatives
Fatty amide
Fatty acyl
Fatty acid
N-acyl-amine
Amino acid or derivatives
Carboxamide group
Amino acid
Secondary carboxylic acid amide
Sulfenyl compound
Carboxylic acid
Organopnictogen compound
Primary aliphatic amine
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Amine
Organic oxide
Primary amine
Organosulfur compound
Organonitrogen compound
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

glutathione derivative (CHEBI:48926 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	5.27 g/L	ALOGPS
logP	-3.2	ALOGPS
logP	-5.5	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	1.79	ChemAxon
pKa (Strongest Basic)	9.31	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	179.05 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	75.2 m³·mol⁻¹	ChemAxon
Polarizability	32.23 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-01po-6291000000-700a78b68cd3c72dace0	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0ukl-9410370000-758e7d3d20ef5e803fa9	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00du-0195000000-0fb852c5aa71ebfacbc3	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0570-4690000000-74c4fbcadf9e75cea5e6	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-4920000000-a75d217a2989134725ab	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-052r-5089000000-0963b985ed393a77403b	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05di-5393000000-80626db3d68b3e84d33f	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03fu-9200000000-c770bc62700bd5b4872c	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0029000000-9285be543171793a7f61	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6u-1941000000-3b0ed9e0505deb83df54	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9400000000-cdcded7632edf6274abf	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-05g0-0193000000-b9ae6fff6991f7a74ac1	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03e9-9440000000-4e976999daadff083f1c	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03dl-9400000000-49e525bdebda32941d94	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192400	Alcohol dehydrogenase class-3	Unknown	P11766	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0002934	Formaldehyde	S-(Hydroxymethyl)glutathione	Not Available	VMH	30371894
MMDBr0002935	S-(Hydroxymethyl)glutathione	S-Formylglutathione	alcohol dehydrogenase 5 (class III), chi polypeptide	VMH	18288723
MMDBr0008483	S-(Hydroxymethyl)glutathione	S-Formylglutathione	Not Available	VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	125	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool; Human sputum; Human unknown; Pig ; Human pleural fluid plaque	Unknown; Metabolic reconstruction
Bacteria	Firmicutes	17	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	1		Metabolic reconstruction
Bacteria	Actinobacteria	1	Human feces	Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	20	Human feces; Human saliva	Unknown
Bacteria	nah	1

Exposure Sources

Source Type	Activity	Data Source	Reference
Drugs	Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0004662

DrugBank ID

DB04153

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023393

KNApSAcK ID

Not Available

Chemspider ID

394301

KEGG Compound ID

C14180

BioCyc ID

S-HYDROXYMETHYLGLUTATHIONE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

PubChem Compound

PDB ID

ChEBI ID

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Gutheil WG, Holmquist B, Vallee BL: Purification, characterization, and partial sequence of the glutathione-dependent formaldehyde dehydrogenase from Escherichia coli: a class III alcohol dehydrogenase. Biochemistry. 1992 Jan 21;31(2):475-81. doi: 10.1021/bi00117a025. [PubMed:1731906 ]
Koivusalo M, Baumann M, Uotila L: Evidence for the identity of glutathione-dependent formaldehyde dehydrogenase and class III alcohol dehydrogenase. FEBS Lett. 1989 Oct 23;257(1):105-9. doi: 10.1016/0014-5793(89)81797-1. [PubMed:2806555 ]
Holmquist B, Moulis JM, Engeland K, Vallee BL: Role of arginine 115 in fatty acid activation and formaldehyde dehydrogenase activity of human class III alcohol dehydrogenase. Biochemistry. 1993 May 18;32(19):5139-44. doi: 10.1021/bi00070a024. [PubMed:8494891 ]
Danielsson O, Shafqat J, Estonius M, el-Ahmad M, Jornvall H: Isozyme multiplicity with anomalous dimer patterns in a class III alcohol dehydrogenase. Effects on the activity and quaternary structure of residue exchanges at "nonfunctional" sites in a native protein. Biochemistry. 1996 Nov 19;35(46):14561-8. doi: 10.1021/bi9618124. [PubMed:8931553 ]
Yang ZN, Bosron WF, Hurley TD: Structure of human chi chi alcohol dehydrogenase: a glutathione-dependent formaldehyde dehydrogenase. J Mol Biol. 1997 Jan 24;265(3):330-43. doi: 10.1006/jmbi.1996.0731. [PubMed:9018047 ]
Sanghani PC, Stone CL, Ray BD, Pindel EV, Hurley TD, Bosron WF: Kinetic mechanism of human glutathione-dependent formaldehyde dehydrogenase. Biochemistry. 2000 Sep 5;39(35):10720-9. doi: 10.1021/bi9929711. [PubMed:10978156 ]
Sanghani PC, Bosron WF, Hurley TD: Human glutathione-dependent formaldehyde dehydrogenase. Structural changes associated with ternary complex formation. Biochemistry. 2002 Dec 24;41(51):15189-94. doi: 10.1021/bi026705q. [PubMed:12484756 ]
Lee SL, Wang MF, Lee AI, Yin SJ: The metabolic role of human ADH3 functioning as ethanol dehydrogenase. FEBS Lett. 2003 Jun 5;544(1-3):143-7. doi: 10.1016/s0014-5793(03)00492-7. [PubMed:12782305 ]

Showing metabocard for S-(Hydroxymethyl)glutathione (MMDBc0029822)

MOL for #<Metabolite:0x00007fdb4d303d30>

3D MOL for #<Metabolite:0x00007fdb4d303d30>

3D SDF for #<Metabolite:0x00007fdb4d303d30>

3D-SDF for #<Metabolite:0x00007fdb4d303d30>

PDB for #<Metabolite:0x00007fdb4d303d30>

3D PDB for #<Metabolite:0x00007fdb4d303d30>

SMILES for #<Metabolite:0x00007fdb4d303d30>

INCHI for #<Metabolite:0x00007fdb4d303d30>

Structure for #<Metabolite:0x00007fdb4d303d30>

3D Structure for #<Metabolite:0x00007fdb4d303d30>