MiMeDB: Showing metabocard for 1-(S-Glutathionyl)-2,4-Dinitrobenzene (MMDBc0048358)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-04-29 21:58:02 UTC

Update Date

2022-09-01 02:14:36 UTC

MiMeDB ID

MMDBc0048358

Metabolite Identification

Common Name

1-(S-Glutathionyl)-2,4-Dinitrobenzene

Description

2,4-dinitrophenyl-S-glutathione, also known as DNP-SG, 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. Based on a literature review a significant number of articles have been published on 2,4-dinitrophenyl-S-glutathione.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304292223582D          

 50 50  0  0  1  0            999 V2000
    6.5428   -8.2143    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0829   -7.5907    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3530   -8.3702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1631   -8.5262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8129   -8.9939    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6230   -9.1498    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0028   -8.8380    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4627   -9.4616    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7327   -8.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2728   -7.4348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9226   -7.9025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1600   -8.2174    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7198   -8.7022    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6525   -7.1230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4151   -6.8080    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8553   -6.3233    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8424   -6.9671    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3825   -6.3434    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7622   -6.0316    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    4.1124   -5.5639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3023   -7.5907    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    2.6787   -7.0506    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7622   -8.2143    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9260   -8.1308    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0829   -9.7734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3204  -10.0884    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8802  -10.5731    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8931   -9.9293    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.1631  -10.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9732  -10.8648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2433  -11.6444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0534  -11.8003    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7032  -12.2680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8931  -12.1121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3530  -12.7357    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6230  -11.3325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8129  -11.1766    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9732  -13.0476    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    9.7834  -13.2035    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    8.4332  -13.6712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5133  -10.2412    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   10.3235  -10.3971    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    9.2433   -9.4616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6230   -6.9671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2770   -7.4700    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4170   -6.7428    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3530   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5428   -6.0316    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    7.8931   -5.5639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  1  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 17 14  1  6  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
  5 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 26 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 30 37  1  0  0  0  0
 37 38  1  0  0  0  0
 34 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  2  0  0  0  0
 31 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  2  0  0  0  0
  2 45  1  0  0  0  0
 45 46  1  0  0  0  0
 45 47  1  0  0  0  0
 45 48  1  0  0  0  0
 48 49  1  0  0  0  0
 48 50  2  0  0  0  0
M  CHG  7  20  -1  22   1  39   1  40  -1  42   1  43  -1  49  -1
M  END


  Mrv1652304292223582D          

 50 50  0  0  1  0            999 V2000
    6.5428   -8.2143    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0829   -7.5907    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3530   -8.3702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1631   -8.5262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8129   -8.9939    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6230   -9.1498    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0028   -8.8380    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4627   -9.4616    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7327   -8.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2728   -7.4348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9226   -7.9025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1600   -8.2174    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7198   -8.7022    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6525   -7.1230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4151   -6.8080    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8553   -6.3233    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8424   -6.9671    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3825   -6.3434    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7622   -6.0316    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    4.1124   -5.5639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3023   -7.5907    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    2.6787   -7.0506    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7622   -8.2143    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9260   -8.1308    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0829   -9.7734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3204  -10.0884    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8802  -10.5731    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8931   -9.9293    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.1631  -10.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9732  -10.8648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2433  -11.6444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0534  -11.8003    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7032  -12.2680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8931  -12.1121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3530  -12.7357    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6230  -11.3325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8129  -11.1766    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9732  -13.0476    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    9.7834  -13.2035    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    8.4332  -13.6712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5133  -10.2412    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   10.3235  -10.3971    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    9.2433   -9.4616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6230   -6.9671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2770   -7.4700    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4170   -6.7428    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3530   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5428   -6.0316    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    7.8931   -5.5639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  1  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 17 14  1  6  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
  5 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 26 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 30 37  1  0  0  0  0
 37 38  1  0  0  0  0
 34 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  2  0  0  0  0
 31 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  2  0  0  0  0
  2 45  1  0  0  0  0
 45 46  1  0  0  0  0
 45 47  1  0  0  0  0
 45 48  1  0  0  0  0
 48 49  1  0  0  0  0
 48 50  2  0  0  0  0
M  CHG  7  20  -1  22   1  39   1  40  -1  42   1  43  -1  49  -1
M  END
> <DATABASE_ID>
MMDBc0048358

> <DATABASE_NAME>
MIME

> <SMILES>
[H]N(C(=O)[C@@]([H])(N([H])C(=O)C([H])([H])C([H])([H])[C@@]([H])(C([O-])=O)[N+]([H])([H])[H])C([H])([H])SC1=C(C([H])=C(C([H])=C1[H])[N+]([O-])=O)[N+]([O-])=O)C([H])([H])C([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H19N5O10S/c17-9(16(26)27)2-4-13(22)19-10(15(25)18-6-14(23)24)7-32-12-3-1-8(20(28)29)5-11(12)21(30)31/h1,3,5,9-10H,2,4,6-7,17H2,(H,18,25)(H,19,22)(H,23,24)(H,26,27)/p-1/t9-,10-/m0/s1

> <INCHI_KEY>
FXEUKVKGTKDDIQ-UWVGGRQHSA-M

> <FORMULA>
C16H18N5O10S

> <MOLECULAR_WEIGHT>
472.41

> <EXACT_MASS>
472.077986554

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
42.680852754447166

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-azaniumyl-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-[(2,4-dinitrophenyl)sulfanyl]ethyl]carbamoyl}butanoate

> <ALOGPS_LOGP>
-1.11

> <JCHEM_LOGP>
-3.299157418084871

> <ALOGPS_LOGS>
-4.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
2.834668235889111

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.5793373910699144

> <JCHEM_PKA_STRONGEST_BASIC>
9.307814895440488

> <JCHEM_POLAR_SURFACE_AREA>
252.38

> <JCHEM_REFRACTIVITY>
139.29909999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.41e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-ammonio-4-{[(1R)-1-(carboxymethylcarbamoyl)-2-[(2,4-dinitrophenyl)sulfanyl]ethyl]carbamoyl}butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  H   UNK     0      12.213 -15.333   0.000  0.00  0.00           H+0
HETATM    2  N   UNK     0      13.221 -14.169   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      13.726 -15.624   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      15.238 -15.915   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      12.717 -16.789   0.000  0.00  0.00           C+0
HETATM    6  H   UNK     0      14.230 -17.080   0.000  0.00  0.00           H+0
HETATM    7  N   UNK     0      11.205 -16.498   0.000  0.00  0.00           N+0
HETATM    8  H   UNK     0      10.197 -17.662   0.000  0.00  0.00           H+0
HETATM    9  C   UNK     0      10.701 -15.042   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      11.709 -13.878   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.189 -14.751   0.000  0.00  0.00           C+0
HETATM   12  H   UNK     0       7.765 -15.339   0.000  0.00  0.00           H+0
HETATM   13  H   UNK     0       8.810 -16.244   0.000  0.00  0.00           H+0
HETATM   14  C   UNK     0       8.685 -13.296   0.000  0.00  0.00           C+0
HETATM   15  H   UNK     0      10.108 -12.708   0.000  0.00  0.00           H+0
HETATM   16  H   UNK     0       9.063 -11.803   0.000  0.00  0.00           H+0
HETATM   17  C   UNK     0       7.172 -13.005   0.000  0.00  0.00           C+0
HETATM   18  H   UNK     0       8.181 -11.841   0.000  0.00  0.00           H+0
HETATM   19  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.156 -11.259   0.000  0.00  0.00           O-1
HETATM   21  O   UNK     0       7.677 -10.386   0.000  0.00  0.00           O+0
HETATM   22  N   UNK     0       6.164 -14.169   0.000  0.00  0.00           N+1
HETATM   23  H   UNK     0       5.000 -13.161   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0       5.156 -15.333   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0       7.328 -15.177   0.000  0.00  0.00           H+0
HETATM   26  C   UNK     0      13.221 -18.244   0.000  0.00  0.00           C+0
HETATM   27  H   UNK     0      11.798 -18.832   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0      12.843 -19.737   0.000  0.00  0.00           H+0
HETATM   29  S   UNK     0      14.734 -18.535   0.000  0.00  0.00           S+0
HETATM   30  C   UNK     0      15.238 -19.990   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      16.750 -20.281   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      17.254 -21.736   0.000  0.00  0.00           C+0
HETATM   33  H   UNK     0      18.766 -22.027   0.000  0.00  0.00           H+0
HETATM   34  C   UNK     0      16.246 -22.900   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      14.734 -22.609   0.000  0.00  0.00           C+0
HETATM   36  H   UNK     0      13.726 -23.773   0.000  0.00  0.00           H+0
HETATM   37  C   UNK     0      14.230 -21.154   0.000  0.00  0.00           C+0
HETATM   38  H   UNK     0      12.717 -20.863   0.000  0.00  0.00           H+0
HETATM   39  N   UNK     0      16.750 -24.355   0.000  0.00  0.00           N+1
HETATM   40  O   UNK     0      18.262 -24.646   0.000  0.00  0.00           O-1
HETATM   41  O   UNK     0      15.742 -25.520   0.000  0.00  0.00           O+0
HETATM   42  N   UNK     0      17.758 -19.117   0.000  0.00  0.00           N+1
HETATM   43  O   UNK     0      19.270 -19.408   0.000  0.00  0.00           O-1
HETATM   44  O   UNK     0      17.254 -17.662   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      14.230 -13.005   0.000  0.00  0.00           C+0
HETATM   46  H   UNK     0      15.450 -13.944   0.000  0.00  0.00           H+0
HETATM   47  H   UNK     0      15.712 -12.587   0.000  0.00  0.00           H+0
HETATM   48  C   UNK     0      13.726 -11.550   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      12.213 -11.259   0.000  0.00  0.00           O-1
HETATM   50  O   UNK     0      14.734 -10.386   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   45                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7   26                                             
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14   18   19   22                                             
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   17   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   22                                                            
CONECT   26    5   27   28   29                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   26   30                                                       
CONECT   30   29   31   37                                                  
CONECT   31   30   32   42                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   39                                                  
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   30   38                                                  
CONECT   38   37                                                            
CONECT   39   34   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39                                                            
CONECT   42   31   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42                                                            
CONECT   45    2   46   47   48                                             
CONECT   46   45                                                            
CONECT   47   45                                                            
CONECT   48   45   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48                                                            
MASTER        0    0    0    0    0    0    0    0   50    0  100    0
END

Synonyms

Value	Source
DNP-SG	ChEBI
S-(2,4-Dinitrophenyl)glutathionate	ChEBI
S-(2,4-Dinitrophenyl)glutathionic acid	Generator

Chemical Formula

C₁₆H₁₈N₅O₁₀S

Average Molecular Weight

472.41

Monoisotopic Molecular Weight

472.077986554

IUPAC Name

(2S)-2-azaniumyl-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-[(2,4-dinitrophenyl)sulfanyl]ethyl]carbamoyl}butanoate

Traditional Name

(2S)-2-ammonio-4-{[(1R)-1-(carboxymethylcarbamoyl)-2-[(2,4-dinitrophenyl)sulfanyl]ethyl]carbamoyl}butanoate

CAS Registry Number

Not Available

SMILES

[H]N(C(=O)[C@@]([H])(N([H])C(=O)C([H])([H])C([H])([H])[C@@]([H])(C([O-])=O)[N+]([H])([H])[H])C([H])([H])SC1=C(C([H])=C(C([H])=C1[H])[N+]([O-])=O)[N+]([O-])=O)C([H])([H])C([O-])=O

InChI Identifier

InChI=1S/C16H19N5O10S/c17-9(16(26)27)2-4-13(22)19-10(15(25)18-6-14(23)24)7-32-12-3-1-8(20(28)29)5-11(12)21(30)31/h1,3,5,9-10H,2,4,6-7,17H2,(H,18,25)(H,19,22)(H,23,24)(H,26,27)/p-1/t9-,10-/m0/s1

InChI Key

FXEUKVKGTKDDIQ-UWVGGRQHSA-M

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 or derivatives
N-acyl-alpha-amino acid
Alpha-amino acid amide
Cysteine or derivatives
Alpha-amino acid
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
L-alpha-amino acid
Nitrobenzene
Aryl thioether
Nitroaromatic compound
Thiophenol ether
Alkylarylthioether
Monocyclic benzene moiety
Benzenoid
N-acyl-amine
Fatty amide
Fatty acyl
Dicarboxylic acid or derivatives
Quaternary ammonium salt
Amino acid
Amino acid or derivatives
Carboxamide group
Carboxylic acid salt
Organic nitro compound
Secondary carboxylic acid amide
C-nitro compound
Thioether
Sulfenyl compound
Organic oxoazanium
Carboxylic acid
Organosulfur compound
Organooxygen compound
Organic salt
Amine
Organic nitrogen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Primary amine
Primary aliphatic amine
Organonitrogen compound
Organic cation
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.014 g/L	ALOGPS
logP	-1.1	ALOGPS
logP	-3.3	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	1.58	ChemAxon
pKa (Strongest Basic)	9.31	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	252.38 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	139.3 m³·mol⁻¹	ChemAxon
Polarizability	42.68 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Deposition Date
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Proteins

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Related Health Condition	Evidence Type	Measured in Matrix	Data Source	Reference

Microbial Sources

Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Fungi	Ascomycota	1

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference	Details

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		details

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

58827315

KEGG Compound ID

Not Available

BioCyc ID

S-24-DINITROPHENYLGLUTATHIONE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25322932

PDB ID

Not Available

ChEBI ID

133977

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Hagenbuch B, Meier PJ: Organic anion transporting polypeptides of the OATP/ SLC21 family: phylogenetic classification as OATP/ SLCO superfamily, new nomenclature and molecular/functional properties. Pflugers Arch. 2004 Feb;447(5):653-65. doi: 10.1007/s00424-003-1168-y. Epub 2003 Oct 25. [PubMed:14579113 ]
Zarubica A, Trompier D, Chimini G: ABCA1, from pathology to membrane function. Pflugers Arch. 2007 Feb;453(5):569-79. doi: 10.1007/s00424-006-0108-z. Epub 2006 Jul 21. [PubMed:16858612 ]
Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]
Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for 1-(S-Glutathionyl)-2,4-Dinitrobenzene (MMDBc0048358)

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