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Showing metabocard for Oxidized glutathione (HMDB0003337)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-12 19:06:03 UTC
Update Date2021-10-13 04:41:16 UTC
HMDB IDHMDB0003337
Secondary Accession Numbers
  • HMDB03337
Metabolite Identification
Common NameOxidized glutathione
DescriptionOxidized glutathione, also known as glutathione disulfide or GSSG, belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by the formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. In humans, oxidized glutathione is involved in the metabolic disorder called leukotriene C4 synthesis deficiency pathway. Outside of the human body, oxidized glutathione has been detected, but not quantified in several different foods, such as leeks, star anises, mamey sapotes, climbing beans, and common persimmons. Oxidized glutathione is a glutathione dimer formed by a disulfide bond between the cysteine sulfhydryl side chains during the course of being oxidized. Glutathione participates in leukotriene synthesis and is a cofactor for the enzyme glutathione peroxidase. It is also important as a hydrophilic molecule that is added to lipophilic toxins and waste in the liver during biotransformation before they can become part of the bile. Glutathione is also needed for the detoxification of methylglyoxal, a toxin produced as a by-product of metabolism. This detoxification reaction is carried out by the glyoxalase system. Glyoxalase I (EC 4.4.1.5) catalyzes the conversion of methylglyoxal and reduced glutathione into S-D-lactoyl-glutathione. Glyoxalase II (EC 3.1.2.6) catalyzes the hydrolysis of S-D-lactoyl-glutathione into glutathione and D-lactate.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0003337 (Oxidized glutathione)

  Mrv1652304292016582D          

 40 39  0  0  1  0            999 V2000
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M  END
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3D MOL for HMDB0003337 (Oxidized glutathione)

HMDB0003337
     RDKit          3D
Oxidized glutathione
 72 71  0  0  0  0  0  0  0  0999 V2000
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M  END
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3D SDF for HMDB0003337 (Oxidized glutathione)

  Mrv1652304292016582D          

 40 39  0  0  1  0            999 V2000
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    4.8673   -6.4351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0685   -2.6325    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1553   -6.8517    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.5798   -6.4351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6233   -3.0492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3653   -3.0492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4435   -6.4351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 25  1  0  0  0  0
  2 26  1  0  0  0  0
  3 23  2  0  0  0  0
  4 24  2  0  0  0  0
  5 27  2  0  0  0  0
  6 28  2  0  0  0  0
  7 37  2  0  0  0  0
  8 37  1  0  0  0  0
  9 38  2  0  0  0  0
 10 38  1  0  0  0  0
 11 39  2  0  0  0  0
 12 39  1  0  0  0  0
 13 40  2  0  0  0  0
 14 40  1  0  0  0  0
 15 21  1  0  0  0  0
 15 27  1  0  0  0  0
 16 22  1  0  0  0  0
 16 28  1  0  0  0  0
 17 23  1  0  0  0  0
 17 31  1  0  0  0  0
 18 24  1  0  0  0  0
 18 32  1  0  0  0  0
 35 19  1  1  0  0  0
 36 20  1  6  0  0  0
 21 23  1  0  0  0  0
 21 25  1  1  0  0  0
 22 24  1  0  0  0  0
 22 26  1  6  0  0  0
 27 29  1  0  0  0  0
 28 30  1  0  0  0  0
 29 34  1  0  0  0  0
 30 33  1  0  0  0  0
 31 37  1  0  0  0  0
 32 38  1  0  0  0  0
 33 35  1  0  0  0  0
 34 36  1  0  0  0  0
 35 39  1  0  0  0  0
 36 40  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0003337

> <DATABASE_NAME>
hmdb

> <SMILES>
N[C@@H](CCC(=O)N[C@@H](CSSC[C@H](NC(=O)CC[C@H](N)C(O)=O)C(=O)NCC(O)=O)C(=O)NCC(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H32N6O12S2/c21-9(19(35)36)1-3-13(27)25-11(17(33)23-5-15(29)30)7-39-40-8-12(18(34)24-6-16(31)32)26-14(28)4-2-10(22)20(37)38/h9-12H,1-8,21-22H2,(H,23,33)(H,24,34)(H,25,27)(H,26,28)(H,29,30)(H,31,32)(H,35,36)(H,37,38)/t9-,10-,11-,12-/m0/s1

> <INCHI_KEY>
YPZRWBKMTBYPTK-BJDJZHNGSA-N

> <FORMULA>
C20H32N6O12S2

> <MOLECULAR_WEIGHT>
612.631

> <EXACT_MASS>
612.151961898

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
58.46704569941549

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-3.60

> <JCHEM_LOGP>
-10.109054127323455

> <ALOGPS_LOGS>
-3.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
2.0279192452272095

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.4383679148014101

> <JCHEM_PKA_STRONGEST_BASIC>
9.613061090727257

> <JCHEM_POLAR_SURFACE_AREA>
317.64000000000004

> <JCHEM_REFRACTIVITY>
136.65439999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
21

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.06e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
glutathione disulfide

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0003337 (Oxidized glutathione)

HMDB0003337
     RDKit          3D
Oxidized glutathione
 72 71  0  0  0  0  0  0  0  0999 V2000
    6.7317    0.4869   -1.2530 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7554   -0.2561   -0.6242 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5060   -1.7103   -0.3958 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3661   -2.0747    0.4663 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0285   -1.6544    0.0391 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8360   -1.2727   -1.1409 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9284   -1.6699    0.9684 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5650   -1.2400    0.5292 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6623   -2.2523    1.1740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0613   -2.2461    0.9323 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0700   -0.4393    1.4160 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2898    0.5511   -0.0570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5060    0.3443   -0.8246 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7358    0.7214   -0.1579 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6624    1.5512   -0.8098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4571    1.9923   -1.9633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9306    1.9064   -0.0930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7516    2.8130   -0.9481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0481    3.1200   -0.2319 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.7496    3.7572    1.0174 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7904    1.8401    0.0303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1128    1.1483   -0.9739 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1142    1.4268    1.3082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7675   -1.0566   -1.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9853   -1.3185   -2.4952 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7984   -2.1213   -0.3693 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0345   -3.4826   -0.8021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0592   -4.4266    0.3453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8755   -3.9467    1.4980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2694   -5.7807    0.1980 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3083    0.0488    1.2552 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6099    0.0238    2.4996 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7968    1.2295    0.7232 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6334    2.3457    1.6637 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9597    2.6664    2.2152 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9722    2.1233    1.7603 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0456    3.5730    3.2359 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0720   -0.0977   -1.3033 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2470    0.5110   -2.3622 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1562   -0.7001   -0.6423 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4495    1.3756   -0.8348 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6740    0.4279   -2.2886 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8806    0.2064    0.4135 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4299   -2.2984   -1.3608 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4829   -2.1079    0.0382 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3956   -3.2246    0.5269 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5731   -1.7440    1.5084 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0488   -1.9683    1.9325 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4303   -1.1219   -0.5025 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1492   -3.2600    0.8748 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9487   -2.1871    2.2911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1358    1.6241    0.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3981    0.2983   -0.7358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4546    0.9715   -1.8114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9071    0.3728    0.8006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5993    2.4486    0.8104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5191    1.0212    0.1651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9109    2.4092   -1.9721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1614    3.7568   -1.0960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6966    3.7800   -0.8908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0541    4.5141    0.9203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3744    3.0205    1.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6384    0.5915    1.4427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7285   -1.9719    0.6397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3124   -3.8497   -1.5503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0528   -3.5269   -1.2547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4669   -6.4108    0.1879 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5446    1.4006   -0.2614 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9194    2.0125    2.4621 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2654    3.2538    1.1626 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7721    4.2712    3.3401 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3349   -0.5195    0.3487 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
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 21 23  1  0
 13 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
  8 31  1  0
 31 32  2  0
 31 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  2  0
 35 37  1  0
  2 38  1  0
 38 39  2  0
 38 40  1  0
  1 41  1  0
  1 42  1  0
  2 43  1  1
  3 44  1  0
  3 45  1  0
  4 46  1  0
  4 47  1  0
  7 48  1  0
  8 49  1  6
  9 50  1  0
  9 51  1  0
 12 52  1  0
 12 53  1  0
 13 54  1  6
 14 55  1  0
 17 56  1  0
 17 57  1  0
 18 58  1  0
 18 59  1  0
 19 60  1  6
 20 61  1  0
 20 62  1  0
 23 63  1  0
 26 64  1  0
 27 65  1  0
 27 66  1  0
 30 67  1  0
 33 68  1  0
 34 69  1  0
 34 70  1  0
 37 71  1  0
 40 72  1  0
M  END
Download

PDB for HMDB0003337 (Oxidized glutathione)

HEADER    PROTEIN                                 29-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-20         0                                  
HETATM    1  S   UNK     0      13.056  -9.597   0.000  0.00  0.00           S+0
HETATM    2  S   UNK     0      13.056  -8.042   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0      15.778 -14.346   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      15.778  -3.358   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      11.727 -10.375   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      11.727  -7.248   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      19.749 -10.375   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      21.078 -12.709   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      19.830  -7.248   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      21.159  -4.914   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       6.282  -7.248   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       4.953  -4.914   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       6.428 -10.375   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       5.115 -12.709   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0      13.056 -12.790   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0      13.056  -4.914   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0      17.108 -12.012   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0      17.108  -5.692   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0       7.595  -3.358   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0       7.757 -14.346   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      14.466 -12.012   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.385  -5.692   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.778 -12.709   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.778  -4.914   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.466 -10.456   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.385  -7.248   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.727 -12.012   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.727  -5.692   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.414 -12.790   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.333  -4.914   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      18.436 -12.709   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      18.436  -4.914   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.004  -5.692   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.086 -12.012   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.595  -4.914   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       7.757 -12.790   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      19.749 -12.012   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      19.830  -5.692   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       6.282  -5.692   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       6.428 -12.012   0.000  0.00  0.00           C+0
CONECT    1    2   25                                                       
CONECT    2    1   26                                                       
CONECT    3   23                                                            
CONECT    4   24                                                            
CONECT    5   27                                                            
CONECT    6   28                                                            
CONECT    7   37                                                            
CONECT    8   37                                                            
CONECT    9   38                                                            
CONECT   10   38                                                            
CONECT   11   39                                                            
CONECT   12   39                                                            
CONECT   13   40                                                            
CONECT   14   40                                                            
CONECT   15   21   27                                                       
CONECT   16   22   28                                                       
CONECT   17   23   31                                                       
CONECT   18   24   32                                                       
CONECT   19   35                                                            
CONECT   20   36                                                            
CONECT   21   15   23   25                                                  
CONECT   22   16   24   26                                                  
CONECT   23    3   17   21                                                  
CONECT   24    4   18   22                                                  
CONECT   25    1   21                                                       
CONECT   26    2   22                                                       
CONECT   27    5   15   29                                                  
CONECT   28    6   16   30                                                  
CONECT   29   27   34                                                       
CONECT   30   28   33                                                       
CONECT   31   17   37                                                       
CONECT   32   18   38                                                       
CONECT   33   30   35                                                       
CONECT   34   29   36                                                       
CONECT   35   19   33   39                                                  
CONECT   36   20   34   40                                                  
CONECT   37    7    8   31                                                  
CONECT   38    9   10   32                                                  
CONECT   39   11   12   35                                                  
CONECT   40   13   14   36                                                  
MASTER        0    0    0    0    0    0    0    0   40    0   78    0
END
Download

3D PDB for HMDB0003337 (Oxidized glutathione)

COMPND    HMDB0003337
HETATM    1  N1  UNL     1       6.732   0.487  -1.253  1.00  0.00           N  
HETATM    2  C1  UNL     1       7.755  -0.256  -0.624  1.00  0.00           C  
HETATM    3  C2  UNL     1       7.506  -1.710  -0.396  1.00  0.00           C  
HETATM    4  C3  UNL     1       6.366  -2.075   0.466  1.00  0.00           C  
HETATM    5  C4  UNL     1       5.029  -1.654   0.039  1.00  0.00           C  
HETATM    6  O1  UNL     1       4.836  -1.273  -1.141  1.00  0.00           O  
HETATM    7  N2  UNL     1       3.928  -1.670   0.968  1.00  0.00           N  
HETATM    8  C5  UNL     1       2.565  -1.240   0.529  1.00  0.00           C  
HETATM    9  C6  UNL     1       1.662  -2.252   1.174  1.00  0.00           C  
HETATM   10  S1  UNL     1      -0.061  -2.246   0.932  1.00  0.00           S  
HETATM   11  S2  UNL     1      -1.070  -0.439   1.416  1.00  0.00           S  
HETATM   12  C7  UNL     1      -1.290   0.551  -0.057  1.00  0.00           C  
HETATM   13  C8  UNL     1      -2.506   0.344  -0.825  1.00  0.00           C  
HETATM   14  N3  UNL     1      -3.736   0.721  -0.158  1.00  0.00           N  
HETATM   15  C9  UNL     1      -4.662   1.551  -0.810  1.00  0.00           C  
HETATM   16  O2  UNL     1      -4.457   1.992  -1.963  1.00  0.00           O  
HETATM   17  C10 UNL     1      -5.931   1.906  -0.093  1.00  0.00           C  
HETATM   18  C11 UNL     1      -6.752   2.813  -0.948  1.00  0.00           C  
HETATM   19  C12 UNL     1      -8.048   3.120  -0.232  1.00  0.00           C  
HETATM   20  N4  UNL     1      -7.750   3.757   1.017  1.00  0.00           N  
HETATM   21  C13 UNL     1      -8.790   1.840   0.030  1.00  0.00           C  
HETATM   22  O3  UNL     1      -9.113   1.148  -0.974  1.00  0.00           O  
HETATM   23  O4  UNL     1      -9.114   1.427   1.308  1.00  0.00           O  
HETATM   24  C14 UNL     1      -2.767  -1.057  -1.286  1.00  0.00           C  
HETATM   25  O5  UNL     1      -2.985  -1.319  -2.495  1.00  0.00           O  
HETATM   26  N5  UNL     1      -2.798  -2.121  -0.369  1.00  0.00           N  
HETATM   27  C15 UNL     1      -3.034  -3.483  -0.802  1.00  0.00           C  
HETATM   28  C16 UNL     1      -3.059  -4.427   0.345  1.00  0.00           C  
HETATM   29  O6  UNL     1      -2.876  -3.947   1.498  1.00  0.00           O  
HETATM   30  O7  UNL     1      -3.269  -5.781   0.198  1.00  0.00           O  
HETATM   31  C17 UNL     1       2.308   0.049   1.255  1.00  0.00           C  
HETATM   32  O8  UNL     1       2.610   0.024   2.500  1.00  0.00           O  
HETATM   33  N6  UNL     1       1.797   1.230   0.723  1.00  0.00           N  
HETATM   34  C18 UNL     1       1.633   2.346   1.664  1.00  0.00           C  
HETATM   35  C19 UNL     1       2.960   2.666   2.215  1.00  0.00           C  
HETATM   36  O9  UNL     1       3.972   2.123   1.760  1.00  0.00           O  
HETATM   37  O10 UNL     1       3.046   3.573   3.236  1.00  0.00           O  
HETATM   38  C20 UNL     1       9.072  -0.098  -1.303  1.00  0.00           C  
HETATM   39  O11 UNL     1       9.247   0.511  -2.362  1.00  0.00           O  
HETATM   40  O12 UNL     1      10.156  -0.700  -0.642  1.00  0.00           O  
HETATM   41  H1  UNL     1       6.450   1.376  -0.835  1.00  0.00           H  
HETATM   42  H2  UNL     1       6.674   0.428  -2.289  1.00  0.00           H  
HETATM   43  H3  UNL     1       7.881   0.206   0.414  1.00  0.00           H  
HETATM   44  H4  UNL     1       7.430  -2.298  -1.361  1.00  0.00           H  
HETATM   45  H5  UNL     1       8.483  -2.108   0.038  1.00  0.00           H  
HETATM   46  H6  UNL     1       6.396  -3.225   0.527  1.00  0.00           H  
HETATM   47  H7  UNL     1       6.573  -1.744   1.508  1.00  0.00           H  
HETATM   48  H8  UNL     1       4.049  -1.968   1.932  1.00  0.00           H  
HETATM   49  H9  UNL     1       2.430  -1.122  -0.502  1.00  0.00           H  
HETATM   50  H10 UNL     1       2.149  -3.260   0.875  1.00  0.00           H  
HETATM   51  H11 UNL     1       1.949  -2.187   2.291  1.00  0.00           H  
HETATM   52  H12 UNL     1      -1.136   1.624   0.265  1.00  0.00           H  
HETATM   53  H13 UNL     1      -0.398   0.298  -0.736  1.00  0.00           H  
HETATM   54  H14 UNL     1      -2.455   0.972  -1.811  1.00  0.00           H  
HETATM   55  H15 UNL     1      -3.907   0.373   0.801  1.00  0.00           H  
HETATM   56  H16 UNL     1      -5.599   2.449   0.810  1.00  0.00           H  
HETATM   57  H17 UNL     1      -6.519   1.021   0.165  1.00  0.00           H  
HETATM   58  H18 UNL     1      -6.911   2.409  -1.972  1.00  0.00           H  
HETATM   59  H19 UNL     1      -6.161   3.757  -1.096  1.00  0.00           H  
HETATM   60  H20 UNL     1      -8.697   3.780  -0.891  1.00  0.00           H  
HETATM   61  H21 UNL     1      -7.054   4.514   0.920  1.00  0.00           H  
HETATM   62  H22 UNL     1      -7.374   3.020   1.649  1.00  0.00           H  
HETATM   63  H23 UNL     1      -9.638   0.592   1.443  1.00  0.00           H  
HETATM   64  H24 UNL     1      -2.729  -1.972   0.640  1.00  0.00           H  
HETATM   65  H25 UNL     1      -2.312  -3.850  -1.550  1.00  0.00           H  
HETATM   66  H26 UNL     1      -4.053  -3.527  -1.255  1.00  0.00           H  
HETATM   67  H27 UNL     1      -2.467  -6.411   0.188  1.00  0.00           H  
HETATM   68  H28 UNL     1       1.545   1.401  -0.261  1.00  0.00           H  
HETATM   69  H29 UNL     1       0.919   2.013   2.462  1.00  0.00           H  
HETATM   70  H30 UNL     1       1.265   3.254   1.163  1.00  0.00           H  
HETATM   71  H31 UNL     1       3.772   4.271   3.340  1.00  0.00           H  
HETATM   72  H32 UNL     1      10.335  -0.520   0.349  1.00  0.00           H  
CONECT    1    2   41   42
CONECT    2    3   38   43
CONECT    3    4   44   45
CONECT    4    5   46   47
CONECT    5    6    6    7
CONECT    7    8   48
CONECT    8    9   31   49
CONECT    9   10   50   51
CONECT   10   11
CONECT   11   12
CONECT   12   13   52   53
CONECT   13   14   24   54
CONECT   14   15   55
CONECT   15   16   16   17
CONECT   17   18   56   57
CONECT   18   19   58   59
CONECT   19   20   21   60
CONECT   20   61   62
CONECT   21   22   22   23
CONECT   23   63
CONECT   24   25   25   26
CONECT   26   27   64
CONECT   27   28   65   66
CONECT   28   29   29   30
CONECT   30   67
CONECT   31   32   32   33
CONECT   33   34   68
CONECT   34   35   69   70
CONECT   35   36   36   37
CONECT   37   71
CONECT   38   39   39   40
CONECT   40   72
END
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SMILES for HMDB0003337 (Oxidized glutathione)

N[C@@H](CCC(=O)N[C@@H](CSSC[C@H](NC(=O)CC[C@H](N)C(O)=O)C(=O)NCC(O)=O)C(=O)NCC(O)=O)C(O)=O
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INCHI for HMDB0003337 (Oxidized glutathione)

InChI=1S/C20H32N6O12S2/c21-9(19(35)36)1-3-13(27)25-11(17(33)23-5-15(29)30)7-39-40-8-12(18(34)24-6-16(31)32)26-14(28)4-2-10(22)20(37)38/h9-12H,1-8,21-22H2,(H,23,33)(H,24,34)(H,25,27)(H,26,28)(H,29,30)(H,31,32)(H,35,36)(H,37,38)/t9-,10-,11-,12-/m0/s1
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
Glutathione disulphideChEBI
GSSGChEBI
Oxidised glutathioneChEBI
OXIDIZED glutathione disulfideChEBI
OxiglutationeChEBI
GlutathioneKegg
Glutathione disulfideGenerator
OXIDIZED glutathione disulphideGenerator
Disulfide, glutathioneMeSH
Glutathione disulfide, ion(1-)MeSH
Glutathione, oxidizedMeSH
Oxidized glutathioneChEBI
Glutathione-S-S-glutathioneHMDB
Glutathione-SSGHMDB
Oxidized L-glutathioneHMDB
SelenoglutathioneHMDB
Chemical FormulaC20H32N6O12S2
Average Molecular Weight612.631
Monoisotopic Molecular Weight612.151961898
IUPAC Name(2S)-2-amino-4-{[(1R)-2-{[(2R)-2-[(4S)-4-amino-4-carboxybutanamido]-2-[(carboxymethyl)carbamoyl]ethyl]disulfanyl}-1-[(carboxymethyl)carbamoyl]ethyl]carbamoyl}butanoic acid
Traditional Nameglutathione disulfide
CAS Registry Number27025-41-8
SMILES
N[C@@H](CCC(=O)N[C@@H](CSSC[C@H](NC(=O)CC[C@H](N)C(O)=O)C(=O)NCC(O)=O)C(=O)NCC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C20H32N6O12S2/c21-9(19(35)36)1-3-13(27)25-11(17(33)23-5-15(29)30)7-39-40-8-12(18(34)24-6-16(31)32)26-14(28)4-2-10(22)20(37)38/h9-12H,1-8,21-22H2,(H,23,33)(H,24,34)(H,25,27)(H,26,28)(H,29,30)(H,31,32)(H,35,36)(H,37,38)/t9-,10-,11-,12-/m0/s1
InChI KeyYPZRWBKMTBYPTK-BJDJZHNGSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPeptides
Alternative Parents
Substituents
  • Alpha peptide
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Tetracarboxylic acid or derivatives
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • Amino acid or derivatives
  • Amino acid
  • Dialkyldisulfide
  • Organic disulfide
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Sulfenyl compound
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Primary aliphatic amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Organopnictogen compound
  • Primary amine
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility300200 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Mitochondria
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Urine
Tissue Locations
  • Brain
  • Epidermis
  • Erythrocyte
  • Fibroblasts
  • Leukocyte
  • Liver
  • Pancreas
  • Placenta
  • Platelet
Pathways
Normal Concentrations
Abnormal Concentrations
Associated Disorders and Diseases
Disease References
Canavan disease
  1. Tavazzi B, Lazzarino G, Leone P, Amorini AM, Bellia F, Janson CG, Di Pietro V, Ceccarelli L, Donzelli S, Francis JS, Giardina B: Simultaneous high performance liquid chromatographic separation of purines, pyrimidines, N-acetylated amino acids, and dicarboxylic acids for the chemical diagnosis of inborn errors of metabolism. Clin Biochem. 2005 Nov;38(11):997-1008. Epub 2005 Sep 1. [PubMed:16139832 ]
Schizophrenia
  1. Ballesteros A, Summerfelt A, Du X, Jiang P, Chiappelli J, Tagamets M, O'Donnell P, Kochunov P, Hong LE: Electrophysiological intermediate biomarkers for oxidative stress in schizophrenia. Clin Neurophysiol. 2013 Nov;124(11):2209-15. doi: 10.1016/j.clinph.2013.05.021. Epub 2013 Jun 30. [PubMed:23823132 ]
Multiple sclerosis
  1. Calabrese V, Scapagnini G, Ravagna A, Bella R, Butterfield DA, Calvani M, Pennisi G, Giuffrida Stella AM: Disruption of thiol homeostasis and nitrosative stress in the cerebrospinal fluid of patients with active multiple sclerosis: evidence for a protective role of acetylcarnitine. Neurochem Res. 2003 Sep;28(9):1321-8. [PubMed:12938853 ]
Alzheimer's disease
  1. Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Frontotemporal dementia
  1. Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Lewy body disease
  1. Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Temporomandibular joint disorder
  1. (). Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles. . .
Attachment loss
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Periodontal Probing Depth
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Associated OMIM IDs
DrugBank IDDB03310
Phenol Explorer Compound IDNot Available
FooDB IDFDB023147
KNApSAcK IDNot Available
Chemspider ID58835
KEGG Compound IDC00127
BioCyc IDOXIDIZED-GLUTATHIONE
BiGG IDNot Available
Wikipedia LinkGlutathione disulfide
METLIN IDNot Available
PubChem Compound65359
PDB IDNot Available
ChEBI ID17858
Food Biomarker OntologyNot Available
VMH IDGTHOX
MarkerDB IDMDB00000421
Good Scents IDrw1736991
References
Synthesis ReferenceSaito, Susumu; Nishijima, Kunihide; Kataoka, Katsuyuki; Aoyanagi, Yoshinori; Fukuda, Yoji; Ito, Homare. Manufacture of oxidized glutathione from reduced glutathione with ascorbic acid and ascorbate oxidase. Jpn. Kokai Tokkyo Koho (1995), 4 pp.
Material Safety Data Sheet (MSDS)Not Available
General References

Only showing the first 10 proteins. There are 14 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details
1. Glutathione reductase, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
Maintains high levels of reduced glutathione in the cytosol.
Gene Name:
GSR
Uniprot ID:
P00390
Molecular weight:
56256.565
Reactions
Glutathione + NADP → Oxidized glutathione + NADPHdetails
Glutathione + NAD → Oxidized glutathione + NADH + Hydrogen Iondetails
Glutathione + NADP → Oxidized glutathione + NADPH + Hydrogen Iondetails
Enzyme Details
2. Peroxiredoxin-6
General function:
Involved in antioxidant activity
Specific function:
Involved in redox regulation of the cell. Can reduce H(2)O(2) and short chain organic, fatty acid, and phospholipid hydroperoxides. May play a role in the regulation of phospholipid turnover as well as in protection against oxidative injury.
Gene Name:
PRDX6
Uniprot ID:
P30041
Molecular weight:
25034.715
Reactions
Glutathione + Hydrogen peroxide → Oxidized glutathione + Waterdetails
Enzyme Details
3. Aminopeptidase N
General function:
Involved in proteolysis
Specific function:
Broad specificity aminopeptidase. Plays a role in the final digestion of peptides generated from hydrolysis of proteins by gastric and pancreatic proteases. May play a critical role in the pathogenesis of cholesterol gallstone disease. May be involved in the metabolism of regulatory peptides of diverse cell types, responsible for the processing of peptide hormones, such as angiotensin III and IV, neuropeptides, and chemokines. Found to cleave antigen peptides bound to major histocompatibility complex class II molecules of presenting cells and to degrade neurotransmitters at synaptic junctions. Is also implicated as a regulator of IL-8 bioavailability in the endometrium, and therefore may contribute to the regulation of angiogenesis. Is used as a marker for acute myeloid leukemia and plays a role in tumor invasion. In case of human coronavirus 229E (HCoV-229E) infection, serves as receptor for HCoV-229E spike glycoprotein. Mediates as well human cytomegalovirus (HCMV) infection.
Gene Name:
ANPEP
Uniprot ID:
P15144
Molecular weight:
Not Available
Enzyme Details
4. Glutathione peroxidase 7
General function:
Involved in glutathione peroxidase activity
Specific function:
It protects esophageal epithelia from hydrogen peroxide-induced oxidative stress. It suppresses acidic bile acid-induced reactive oxigen species (ROS) and protects against oxidative DNA damage and double-strand breaks.
Gene Name:
GPX7
Uniprot ID:
Q96SL4
Molecular weight:
20995.88
Reactions
Glutathione + Hydrogen peroxide → Oxidized glutathione + Waterdetails
Glutathione + 5(S)-Hydroperoxyeicosatetraenoic acid → Oxidized glutathione + 5-HETE + Waterdetails
Glutathione + 15(S)-HPETE → Oxidized glutathione + 15-HETE + Waterdetails
Enzyme Details
5. Epididymal secretory glutathione peroxidase
General function:
Involved in glutathione peroxidase activity
Specific function:
Protects cells and enzymes from oxidative damage, by catalyzing the reduction of hydrogen peroxide, lipid peroxides and organic hydroperoxide, by glutathione. May constitute a glutathione peroxidase-like protective system against peroxide damage in sperm membrane lipids.
Gene Name:
GPX5
Uniprot ID:
O75715
Molecular weight:
25202.14
Reactions
Glutathione + Hydrogen peroxide → Oxidized glutathione + Waterdetails
Glutathione + 5(S)-Hydroperoxyeicosatetraenoic acid → Oxidized glutathione + 5-HETE + Waterdetails
Glutathione + 15(S)-HPETE → Oxidized glutathione + 15-HETE + Waterdetails
Enzyme Details
6. Glutathione S-transferase omega-1
General function:
Involved in glutathione transferase activity
Specific function:
Exhibits glutathione-dependent thiol transferase and dehydroascorbate reductase activities. Has S-(phenacyl)glutathione reductase activity. Has also glutathione S-transferase activity. Participates in the biotransformation of inorganic arsenic and reduces monomethylarsonic acid (MMA) and dimethylarsonic acid.
Gene Name:
GSTO1
Uniprot ID:
P78417
Molecular weight:
27565.6
Reactions
Glutathione + Dehydroascorbic acid → Oxidized glutathione + Ascorbic aciddetails
Methylarsonate + Glutathione → Methylarsonite + Oxidized glutathione + Waterdetails
Enzyme Details
7. Glutathione peroxidase 6
General function:
Involved in glutathione peroxidase activity
Specific function:
Not Available
Gene Name:
GPX6
Uniprot ID:
P59796
Molecular weight:
24970.46
Reactions
Glutathione + Hydrogen peroxide → Oxidized glutathione + Waterdetails
Glutathione + 5(S)-Hydroperoxyeicosatetraenoic acid → Oxidized glutathione + 5-HETE + Waterdetails
Glutathione + 15(S)-HPETE → Oxidized glutathione + 15-HETE + Waterdetails
Enzyme Details
8. Glutathione peroxidase 1
General function:
Involved in glutathione peroxidase activity
Specific function:
Protects the hemoglobin in erythrocytes from oxidative breakdown.
Gene Name:
GPX1
Uniprot ID:
P07203
Molecular weight:
22087.94
Reactions
Glutathione + Hydrogen peroxide → Oxidized glutathione + Waterdetails
Glutathione + 5(S)-Hydroperoxyeicosatetraenoic acid → Oxidized glutathione + 5-HETE + Waterdetails
Glutathione + 15(S)-HPETE → Oxidized glutathione + 15-HETE + Waterdetails
Enzyme Details
9. Phospholipid hydroperoxide glutathione peroxidase, mitochondrial
General function:
Involved in glutathione peroxidase activity
Specific function:
Protects cells against membrane lipid peroxidation and cell death. Required for normal sperm development and male fertility. Could play a major role in protecting mammals from the toxicity of ingested lipid hydroperoxides. Essential for embryonic development. Protects from radiation and oxidative damage (By similarity).
Gene Name:
GPX4
Uniprot ID:
P36969
Molecular weight:
25046.57
Reactions
Glutathione + a lipid hydroperoxide → Oxidized glutathione + lipid + Waterdetails
Lipid hydroperoxide + Glutathione → Lipid + Oxidized glutathione + Waterdetails
Enzyme Details
10. Glutathione peroxidase 3
General function:
Involved in glutathione peroxidase activity
Specific function:
Protects cells and enzymes from oxidative damage, by catalyzing the reduction of hydrogen peroxide, lipid peroxides and organic hydroperoxide, by glutathione.
Gene Name:
GPX3
Uniprot ID:
P22352
Molecular weight:
25552.185
Reactions
Glutathione + Hydrogen peroxide → Oxidized glutathione + Waterdetails
Glutathione + 5(S)-Hydroperoxyeicosatetraenoic acid → Oxidized glutathione + 5-HETE + Waterdetails
Glutathione + 15(S)-HPETE → Oxidized glutathione + 15-HETE + Waterdetails

Only showing the first 10 proteins. There are 14 proteins in total.

Show all enzymes and transporters