NP-MRD: Showing NP-Card for Glutathione (NP0001080)

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Record Information

Version

1.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-08-19 23:58:44 UTC

NP-MRD ID

NP0001080

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Glutathione

Description

Glutathione is a compound synthesized from cysteine, perhaps the most important member of the body's toxic waste disposal team. Like cysteine, glutathione contains the crucial thiol (-SH) group that makes it an effective antioxidant. There are virtually no living organisms on this planet-animal or plant whose cells don't contain some glutathione. Scientists have speculated that glutathione was essential to the very development of life on earth. Glutathione has many roles; in none does it act alone. It is a coenzyme in various enzymatic reactions. The most important of these are redox reactions, in which the thiol grouping on the cysteine portion of cell membranes protects against peroxidation; and conjugation reactions, in which glutathione (especially in the liver) binds with toxic chemicals in order to detoxify them. Glutathione is also important in red and white blood cell formation and throughout the immune system. Glutathione's clinical uses include the prevention of oxygen toxicity in hyperbaric oxygen therapy, treatment of lead and other heavy metal poisoning, lowering of the toxicity of chemotherapy and radiation in cancer treatments, and reversal of cataracts. (Http://Www.Dcnutrition.Com/AminoAcids/) 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 to S-D-Lactoyl-glutathione. Glyoxalase II (EC 3.1.2.6) Catalyzes the hydrolysis of S-D-Lactoyl-glutathione to glutathione and D-lactate. GSH is known as a substrate in both conjugation reactions and reduction reactions, catalyzed by glutathione S-transferase enzymes in cytosol, microsomes, and mitochondria. However, it is also capable of participating in non-enzymatic conjugation with some chemicals, as in the case of n-acetyl-p-benzoquinone imine (NAPQI), the reactive cytochrome P450-reactive metabolite formed by acetaminophen, that becomes toxic when GSH is depleted by an overdose (of acetaminophen). Glutathione in this capacity binds to NAPQI as a suicide substrate and in the process detoxifies it, taking the place of cellular protein thiol groups which would otherwise be covalently modified; when all GSH has been spent, NAPQI begins to react with the cellular proteins, killing the cells in the process. The preferred treatment for an overdose of this painkiller is the administration (usually in atomized form) of N-acetylcysteine, which is used by cells to replace spent GSSG and renew the usable GSH pool. (Http://En.Wikipedia.Org/wiki/glutathione).

Structure

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


     RDKit          2D

 37 36  0  0  0  0  0  0  0  0999 V2000
   -2.1346   -2.1110    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4466   -1.3838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7195   -0.0719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9924    1.2401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2652    2.5521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0379    3.8378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2345    2.5784    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0072    1.2927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    0.0070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5525   -1.2787    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.2929    2.0654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2666    3.5651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6049    1.3383    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6312   -0.1615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6574   -1.6613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3718   -2.4339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9694   -2.3884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7586   -0.6567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9675    0.8287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0443   -1.4294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1083   -3.6107    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7643   -1.5008    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1737   -2.6958    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9330    0.8098    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3286   -0.6336    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3043    1.9672    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0094    0.5260    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9616    3.8904    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0498    0.5446    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9417    0.3623    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4942   -0.7656    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3292   -1.4580    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8906    2.1109    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1309   -0.1352    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1823   -0.5499    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9957   -3.8882    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3562   -0.7023    0.0000 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
  8 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
  2 18  1  0
 18 19  2  0
 18 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  1
  3 24  1  1
  3 25  1  0
  4 26  1  1
  4 27  1  0
  7 28  1  0
  8 29  1  1
  9 30  1  6
  9 31  1  0
 10 32  1  0
 13 33  1  0
 14 34  1  1
 14 35  1  0
 17 36  1  0
 20 37  1  0
M  END

HMDB0000125
     RDKit          3D
Glutathione
 37 36  0  0  0  0  0  0  0  0999 V2000
    5.0693   -0.2304    1.5246 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6419   -0.4408    1.3503 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4971   -1.3945    0.2007 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0954   -1.7551   -0.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2589   -0.6084   -0.5583 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7237    0.5720   -0.6099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1026   -0.8089   -0.8996 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9421    0.3075   -1.2973 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5277    0.1198   -2.6712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5482   -1.3782   -2.7227 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0967    0.4190   -0.3407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2090   -0.3823    0.6100 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0556    1.4339   -0.5201 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1652    1.5376    0.4028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0243    2.6738    0.0023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7284    3.3601   -0.9980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1644    2.9493    0.7727 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0401   -1.0201    2.5907 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8059   -1.2516    2.6207 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8015   -1.3124    3.7155 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5563   -1.0334    1.9492 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3053    0.6940    1.9129 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1541    0.5354    1.2057 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1280   -2.2785    0.4368 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9668   -0.9238   -0.7117 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1785   -2.4129   -1.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5944   -2.3901    0.6020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4940   -1.7677   -0.8615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3704    1.2472   -1.2832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7580    0.1004   -3.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1956    0.9787   -2.8629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8625   -2.4917   -2.2011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9620    2.1198   -1.3316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7599    0.5823    0.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7524    1.6754    1.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8458    3.5933    0.3962 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7477   -1.0187    3.8540 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
  8 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
  2 18  1  0
 18 19  2  0
 18 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  6
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  7 28  1  0
  8 29  1  6
  9 30  1  0
  9 31  1  0
 10 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 17 36  1  0
 20 37  1  0
M  END


     RDKit          2D

 37 36  0  0  0  0  0  0  0  0999 V2000
   -2.1346   -2.1110    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4466   -1.3838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7195   -0.0719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9924    1.2401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2652    2.5521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0379    3.8378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2345    2.5784    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0072    1.2927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    0.0070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5525   -1.2787    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.2929    2.0654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2666    3.5651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6049    1.3383    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6312   -0.1615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6574   -1.6613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3718   -2.4339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9694   -2.3884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7586   -0.6567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9675    0.8287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0443   -1.4294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1083   -3.6107    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7643   -1.5008    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1737   -2.6958    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9330    0.8098    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3286   -0.6336    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3043    1.9672    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0094    0.5260    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9616    3.8904    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0498    0.5446    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9417    0.3623    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4942   -0.7656    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3292   -1.4580    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8906    2.1109    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1309   -0.1352    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1823   -0.5499    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9957   -3.8882    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3562   -0.7023    0.0000 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
  8 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
  2 18  1  0
 18 19  2  0
 18 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  1
  3 24  1  1
  3 25  1  0
  4 26  1  1
  4 27  1  0
  7 28  1  0
  8 29  1  1
  9 30  1  6
  9 31  1  0
 10 32  1  0
 13 33  1  0
 14 34  1  1
 14 35  1  0
 17 36  1  0
 20 37  1  0
M  END
> <DATABASE_ID>
NP0001080

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H17N3O6S/c11-5(10(18)19)1-2-7(14)13-6(4-20)9(17)12-3-8(15)16/h5-6,20H,1-4,11H2,(H,12,17)(H,13,14)(H,15,16)(H,18,19)/t5-,6-/m0/s1

> <INCHI_KEY>
RWSXRVCMGQZWBV-WDSKDSINSA-N

> <FORMULA>
C10H17N3O6S

> <MOLECULAR_WEIGHT>
307.323

> <EXACT_MASS>
307.083805981

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
29.11283212542198

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-2.74

> <JCHEM_LOGP>
-4.88467621618675

> <ALOGPS_LOGS>
-2.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.737311352465548

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.9364037247697885

> <JCHEM_PKA_STRONGEST_BASIC>
9.223740958320658

> <JCHEM_POLAR_SURFACE_AREA>
158.82000000000002

> <JCHEM_REFRACTIVITY>
69.11490000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.79e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
glutathione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000125
     RDKit          3D
Glutathione
 37 36  0  0  0  0  0  0  0  0999 V2000
    5.0693   -0.2304    1.5246 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6419   -0.4408    1.3503 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4971   -1.3945    0.2007 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0954   -1.7551   -0.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2589   -0.6084   -0.5583 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7237    0.5720   -0.6099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1026   -0.8089   -0.8996 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9421    0.3075   -1.2973 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5277    0.1198   -2.6712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5482   -1.3782   -2.7227 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0967    0.4190   -0.3407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2090   -0.3823    0.6100 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0556    1.4339   -0.5201 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1652    1.5376    0.4028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0243    2.6738    0.0023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7284    3.3601   -0.9980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1644    2.9493    0.7727 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0401   -1.0201    2.5907 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8059   -1.2516    2.6207 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8015   -1.3124    3.7155 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5563   -1.0334    1.9492 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3053    0.6940    1.9129 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1541    0.5354    1.2057 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1280   -2.2785    0.4368 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9668   -0.9238   -0.7117 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1785   -2.4129   -1.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5944   -2.3901    0.6020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4940   -1.7677   -0.8615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3704    1.2472   -1.2832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7580    0.1004   -3.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1956    0.9787   -2.8629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8625   -2.4917   -2.2011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9620    2.1198   -1.3316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7599    0.5823    0.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7524    1.6754    1.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8458    3.5933    0.3962 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7477   -1.0187    3.8540 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
  8 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
  2 18  1  0
 18 19  2  0
 18 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  6
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  7 28  1  0
  8 29  1  6
  9 30  1  0
  9 31  1  0
 10 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 17 36  1  0
 20 37  1  0
M  END

HEADER    PROTEIN                                 03-SEP-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 143                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-20         0                                  
HETATM    1  S   UNK     0      11.909  -2.071   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0      10.576  -1.301   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      14.577   2.549   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.907   1.009   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       5.241  -1.301   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      19.911   1.009   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      18.578  -1.301   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0      11.909   1.009   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       6.574   2.549   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      15.910   0.239   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       7.908   0.239   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.242   1.009   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.243   0.239   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.574   1.009   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.576   0.239   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.243  -1.301   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.577   1.009   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.241   0.239   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      17.244   1.009   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      18.578   0.239   0.000  0.00  0.00           C+0
CONECT    1   16                                                            
CONECT    2   15                                                            
CONECT    3   17                                                            
CONECT    4   18                                                            
CONECT    5   18                                                            
CONECT    6   20                                                            
CONECT    7   20                                                            
CONECT    8   13   15                                                       
CONECT    9   14                                                            
CONECT   10   17   19                                                       
CONECT   11   12   14                                                       
CONECT   12   11   15                                                       
CONECT   13    8   16   17                                                  
CONECT   14    9   11   18                                                  
CONECT   15    2    8   12                                                  
CONECT   16    1   13                                                       
CONECT   17    3   10   13                                                  
CONECT   18    4    5   14                                                  
CONECT   19   10   20                                                       
CONECT   20    6    7   19                                                  
MASTER        0    0    0    0    0    0    0    0   20    0   38    0
END

COMPND    HMDB0000125
HETATM    1  N1  UNL     1       5.069  -0.230   1.525  1.00  0.00           N  
HETATM    2  C1  UNL     1       3.642  -0.441   1.350  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.497  -1.395   0.201  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.095  -1.755  -0.157  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.259  -0.608  -0.558  1.00  0.00           C  
HETATM    6  O1  UNL     1       1.724   0.572  -0.610  1.00  0.00           O  
HETATM    7  N2  UNL     1      -0.103  -0.809  -0.900  1.00  0.00           N  
HETATM    8  C5  UNL     1      -0.942   0.308  -1.297  1.00  0.00           C  
HETATM    9  C6  UNL     1      -1.528   0.120  -2.671  1.00  0.00           C  
HETATM   10  S1  UNL     1      -2.548  -1.378  -2.723  1.00  0.00           S  
HETATM   11  C7  UNL     1      -2.097   0.419  -0.341  1.00  0.00           C  
HETATM   12  O2  UNL     1      -2.209  -0.382   0.610  1.00  0.00           O  
HETATM   13  N3  UNL     1      -3.056   1.434  -0.520  1.00  0.00           N  
HETATM   14  C8  UNL     1      -4.165   1.538   0.403  1.00  0.00           C  
HETATM   15  C9  UNL     1      -5.024   2.674   0.002  1.00  0.00           C  
HETATM   16  O3  UNL     1      -4.728   3.360  -0.998  1.00  0.00           O  
HETATM   17  O4  UNL     1      -6.164   2.949   0.773  1.00  0.00           O  
HETATM   18  C10 UNL     1       3.040  -1.020   2.591  1.00  0.00           C  
HETATM   19  O5  UNL     1       1.806  -1.252   2.621  1.00  0.00           O  
HETATM   20  O6  UNL     1       3.802  -1.312   3.715  1.00  0.00           O  
HETATM   21  H1  UNL     1       5.556  -1.033   1.949  1.00  0.00           H  
HETATM   22  H2  UNL     1       5.305   0.694   1.913  1.00  0.00           H  
HETATM   23  H3  UNL     1       3.154   0.535   1.206  1.00  0.00           H  
HETATM   24  H4  UNL     1       4.128  -2.279   0.437  1.00  0.00           H  
HETATM   25  H5  UNL     1       3.967  -0.924  -0.712  1.00  0.00           H  
HETATM   26  H6  UNL     1       2.179  -2.413  -1.075  1.00  0.00           H  
HETATM   27  H7  UNL     1       1.594  -2.390   0.602  1.00  0.00           H  
HETATM   28  H8  UNL     1      -0.494  -1.768  -0.861  1.00  0.00           H  
HETATM   29  H9  UNL     1      -0.370   1.247  -1.283  1.00  0.00           H  
HETATM   30  H10 UNL     1      -0.758   0.100  -3.464  1.00  0.00           H  
HETATM   31  H11 UNL     1      -2.196   0.979  -2.863  1.00  0.00           H  
HETATM   32  H12 UNL     1      -1.862  -2.492  -2.201  1.00  0.00           H  
HETATM   33  H13 UNL     1      -2.962   2.120  -1.332  1.00  0.00           H  
HETATM   34  H14 UNL     1      -4.760   0.582   0.417  1.00  0.00           H  
HETATM   35  H15 UNL     1      -3.752   1.675   1.428  1.00  0.00           H  
HETATM   36  H16 UNL     1      -6.846   3.593   0.396  1.00  0.00           H  
HETATM   37  H17 UNL     1       4.748  -1.019   3.854  1.00  0.00           H  
CONECT    1    2   21   22
CONECT    2    3   18   23
CONECT    3    4   24   25
CONECT    4    5   26   27
CONECT    5    6    6    7
CONECT    7    8   28
CONECT    8    9   11   29
CONECT    9   10   30   31
CONECT   10   32
CONECT   11   12   12   13
CONECT   13   14   33
CONECT   14   15   34   35
CONECT   15   16   16   17
CONECT   17   36
CONECT   18   19   19   20
CONECT   20   37
END

HMDB0000125
     RDKit          3D
Glutathione
 37 36  0  0  0  0  0  0  0  0999 V2000
    5.0693   -0.2304    1.5246 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6419   -0.4408    1.3503 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4971   -1.3945    0.2007 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0954   -1.7551   -0.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2589   -0.6084   -0.5583 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7237    0.5720   -0.6099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1026   -0.8089   -0.8996 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9421    0.3075   -1.2973 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5277    0.1198   -2.6712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5482   -1.3782   -2.7227 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0967    0.4190   -0.3407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2090   -0.3823    0.6100 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0556    1.4339   -0.5201 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1652    1.5376    0.4028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0243    2.6738    0.0023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7284    3.3601   -0.9980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1644    2.9493    0.7727 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0401   -1.0201    2.5907 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8059   -1.2516    2.6207 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8015   -1.3124    3.7155 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5563   -1.0334    1.9492 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3053    0.6940    1.9129 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1541    0.5354    1.2057 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1280   -2.2785    0.4368 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9668   -0.9238   -0.7117 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1785   -2.4129   -1.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5944   -2.3901    0.6020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4940   -1.7677   -0.8615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3704    1.2472   -1.2832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7580    0.1004   -3.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1956    0.9787   -2.8629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8625   -2.4917   -2.2011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9620    2.1198   -1.3316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7599    0.5823    0.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7524    1.6754    1.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8458    3.5933    0.3962 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7477   -1.0187    3.8540 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
  8 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
  2 18  1  0
 18 19  2  0
 18 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  6
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  7 28  1  0
  8 29  1  6
  9 30  1  0
  9 31  1  0
 10 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 17 36  1  0
 20 37  1  0
M  END

View in JSmol

Synonyms

Value	Source
5-L-Glutamyl-L-cysteinylglycine	ChEBI
gamma-L-Glutamyl-L-cysteinyl-glycine	ChEBI
Glutathione-SH	ChEBI
GSH	ChEBI
N-(N-gamma-L-Glutamyl-L-cysteinyl)glycine	ChEBI
Reduced glutathione	ChEBI
Poly(gamma-glutamylcysteine)glycine	Kegg
(gamma-Glutamylcysteine)N-glycine	Kegg
Tathion	Kegg
g-L-Glutamyl-L-cysteinyl-glycine	Generator
Γ-L-glutamyl-L-cysteinyl-glycine	Generator
N-(N-g-L-Glutamyl-L-cysteinyl)glycine	Generator
N-(N-Γ-L-glutamyl-L-cysteinyl)glycine	Generator
Poly(g-glutamylcysteine)glycine	Generator
Poly(γ-glutamylcysteine)glycine	Generator
(g-Glutamylcysteine)N-glycine	Generator
(Γ-glutamylcysteine)N-glycine	Generator
Agifutol S	HMDB
Bakezyme RX	HMDB
Copren	HMDB
Deltathione	HMDB
gamma-Glutamylcysteinylglycine	HMDB
gamma-L-Glutamyl-L-cysteinylglycine	HMDB
Glutathion	HMDB
Glutathione red	HMDB
Glutathione reduced	HMDB
Glutatiol	HMDB
Glutatione	HMDB
Glutide	HMDB
Glutinal	HMDB
Isethion	HMDB
L-g-Glutamyl-L-cysteinyl-glycine	HMDB
L-gamma-Glutamyl-L-cysteinyl-glycine	HMDB
L-gamma-Glutamyl-L-cysteinylglycine	HMDB
L-Glutamyl-L-cysteinylglycine	HMDB
L-Glutathione	HMDB
L-Glutathione reduce	HMDB
Ledac	HMDB
Neuthion	HMDB
Red. glutathione	HMDB
Tathione	HMDB
Triptide	HMDB
Glutathione, reduced	HMDB
gamma L Glu L cys gly	HMDB
gamma-L-Glu-L-cys-gly	HMDB
gamma L Glutamyl L cysteinylglycine	HMDB

Chemical Formula

C₁₀H₁₇N₃O₆S

Average Mass

307.3230 Da

Monoisotopic Mass

307.08381 Da

IUPAC Name

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

Traditional Name

glutathione

CAS Registry Number

70-18-8

SMILES

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

InChI Identifier

InChI=1S/C10H17N3O6S/c11-5(10(18)19)1-2-7(14)13-6(4-20)9(17)12-3-8(15)16/h5-6,20H,1-4,11H2,(H,12,17)(H,13,14)(H,15,16)(H,18,19)/t5-,6-/m0/s1

InChI Key

RWSXRVCMGQZWBV-WDSKDSINSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, simulated)	Varshavi.d26			2021-08-07	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Abelmoschus esculentus	FooDB	FooDB
Actinidia chinensis	FooDB	FooDB
Agaricus bisporus	FooDB	FooDB
Agave	FooDB	FooDB
Allium ampeloprasum	FooDB	FooDB
Allium ascalonicum	FooDB	FooDB
Allium cepa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Allium cepa L.	FooDB	FooDB
Allium fistulosum	FooDB	FooDB
Allium sativum	KNApSAcK Database	22123792
Allium schoenoprasum	FooDB	FooDB
Allium tuberosum	FooDB	FooDB
Aloe africana	LOTUS Database	35616633
Aloysia triphylla	FooDB	FooDB
Amaranthus	FooDB	FooDB
Amelanchier alnifolia	FooDB	FooDB
Anacardium occidentale	FooDB	FooDB
Ananas comosus	FooDB	FooDB
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anethum graveolens	FooDB	FooDB
Angelica keiskei	FooDB	FooDB
Annona cherimola	FooDB	FooDB
Annona muricata	FooDB	FooDB
Annona reticulata	FooDB	FooDB
Annona squamosa	FooDB	FooDB
Anser anser	FooDB	FooDB
Anthriscus cerefolium	FooDB	FooDB
Apium graveolens	FooDB	FooDB
Apium graveolens var. dulce	FooDB	FooDB
Apium graveolens var. rapaceum	FooDB	FooDB
Apium graveolens var. secalinum	FooDB	FooDB
Arabidopsis thaliana	KNApSAcK Database	22123792
Arachis hypogaea	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Arctium lappa	FooDB	FooDB
Armoracia rusticana	FooDB	FooDB
Artemisia dracunculus	FooDB	FooDB
Artemisia vulgaris	FooDB	FooDB
Artocarpus altilis	FooDB	FooDB
Artocarpus heterophyllus	FooDB	FooDB
Asparagus officinalis	FooDB	FooDB
Attalea speciosa	FooDB	FooDB
Auricularia auricula-judae	FooDB	FooDB
Auricularia polytricha	FooDB	FooDB
Avena sativa L.	FooDB	FooDB
Averrhoa carambola	FooDB	FooDB
Basella alba	FooDB	FooDB
Benincasa hispida	FooDB	FooDB
Bertholletia excelsa	FooDB	FooDB
Beta vulgaris	FooDB	FooDB
Beta vulgaris ssp. cicla	FooDB	FooDB
Bison bison	FooDB	FooDB
Borago officinalis	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Brassica alboglabra	FooDB	FooDB
Brassica juncea	FooDB	FooDB
Brassica napus	FooDB	FooDB
Brassica napus var. napus	FooDB	FooDB
Brassica oleracea	FooDB	FooDB
Brassica oleracea var. botrytis	FooDB	FooDB
Brassica oleracea var. capitata	FooDB	FooDB
Brassica oleracea var. gemmifera	FooDB	FooDB
Brassica oleracea var. gongylodes	FooDB	FooDB
Brassica oleracea var. italica	FooDB	FooDB
Brassica oleracea var. sabauda	FooDB	FooDB
Brassica oleracea var. viridis	FooDB	FooDB
Brassica rapa	FooDB	FooDB
Brassica rapa ssp. chinensis	FooDB	FooDB
Brassica rapa var. pekinensis	FooDB	FooDB
Brassica rapa var. rapa	FooDB	FooDB
Brassica ruvo	FooDB	FooDB
Brosimum alicastrum	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Byrsonima crassifolia	FooDB	FooDB
Cajanus cajan	FooDB	FooDB
Canarium ovatum	FooDB	FooDB
Cannabis sativa	CannabisDB	Not Available
Cantharellus cibarius	FooDB	FooDB
Capparis spinosa	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Capsicum annuum	FooDB	FooDB
Capsicum annuum L.	FooDB	FooDB
Capsicum annuum var. annuum	FooDB	FooDB
Capsicum chinense	FooDB	FooDB
Capsicum pubescens	FooDB	FooDB
Carica papaya L.	FooDB	FooDB
Carissa macrocarpa	FooDB	FooDB
Carthamus tinctorius	FooDB	FooDB
Carum carvi	FooDB	FooDB
Carya	FooDB	FooDB
Carya illinoinensis	FooDB	FooDB
Castanea	FooDB	FooDB
Castanea crenata	FooDB	FooDB
Castanea mollissima	FooDB	FooDB
Castanea sativa	FooDB	FooDB
Ceratonia siliqua	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Chamaemelum nobile	FooDB	FooDB
Chamerion angustifolium	FooDB	FooDB
Chenopodium album	FooDB	FooDB
Chenopodium quinoa	FooDB	FooDB
Chrysanthemum coronarium	FooDB	FooDB
Cicer arietinum	FooDB	FooDB
Cichorium endivia	FooDB	FooDB
Cichorium intybus	FooDB	FooDB
Cinnamomum	FooDB	FooDB
Cinnamomum aromaticum	FooDB	FooDB
Cinnamomum verum	FooDB	FooDB
Cirsium	FooDB	FooDB
Citrullus lanatus	FooDB	FooDB
Citrus ×limon (L.) Burm. f. (pro sp.)	FooDB	FooDB
Citrus aurantiifolia	FooDB	FooDB
Citrus latifolia	FooDB	FooDB
Citrus limon	FooDB	FooDB
Citrus maxima	FooDB	FooDB
Citrus paradisi	FooDB	FooDB
Citrus reticulata	FooDB	FooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)	FooDB	FooDB
Cocos nucifera	FooDB	FooDB
Coffea arabica L.	FooDB	FooDB
Coffea canephora	FooDB	FooDB
Colocasia esculenta	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Corchorus olitorius	FooDB	FooDB
Coriandrum sativum L.	FooDB	FooDB
Corylus	FooDB	FooDB
Corylus avellana	FooDB	FooDB
Crateva religiosa	FooDB	FooDB
Crocus sativus	FooDB	FooDB
Cucumis melo	FooDB	FooDB
Cucumis metuliferus	FooDB	FooDB
Cucumis sativus	LOTUS Database	35616633
Cucumis sativus L.	FooDB	FooDB
Cucurbita	FooDB	FooDB
Cucurbita maxima	FooDB	FooDB
Cucurbita moschata	FooDB	FooDB
Cuminum cyminum	FooDB	FooDB
Curcuma longa	FooDB	FooDB
Cydonia oblonga	FooDB	FooDB
Cymbopogon citratus	FooDB	FooDB
Cynara cardunculus	FooDB	FooDB
Cynara scolymus	FooDB	FooDB
Daucus carota	FooDB	FooDB
Daucus carota ssp. sativus	FooDB	FooDB
Dimocarpus longan	FooDB	FooDB
Dioscorea	FooDB	FooDB
Dioscorea pentaphylla	FooDB	FooDB
Diospyros	FooDB	FooDB
Diospyros kaki	FooDB	FooDB
Diospyros virginiana	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Durio zibethinus	FooDB	FooDB
Dysphania ambrosioides	FooDB	FooDB
Elaeis	FooDB	FooDB
Eleocharis dulcis	FooDB	FooDB
Elettaria cardamomum	FooDB	FooDB
Empetrum nigrum	FooDB	FooDB
Enterococcus faecalis	LOTUS Database	35616633
Equus caballus	FooDB	FooDB
Eragrostis tef	FooDB	FooDB
Eriobotrya japonica	FooDB	FooDB
Eruca vesicaria subsp. Sativa	FooDB	FooDB
Eugenia javanica	FooDB	FooDB
Eugenia uniflora	FooDB	FooDB
Eutrema japonicum	FooDB	FooDB
Fagopyrum esculentum	FooDB	FooDB
Fagopyrum tataricum	FooDB	FooDB
Fagus	FooDB	FooDB
Feijoa sellowiana	FooDB	FooDB
Ficus carica	FooDB	FooDB
Flammulina velutipes	FooDB	FooDB
Foeniculum vulgare	FooDB	FooDB
Fragaria x ananassa	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Garcinia mangostana	FooDB	FooDB
Gaylussacia baccata	FooDB	FooDB
Ginkgo biloba	FooDB	FooDB
Glycine max	FooDB	FooDB
Gossypium	FooDB	FooDB
Grifola frondosa	FooDB	FooDB
Hedysarum alpinum	FooDB	FooDB
Helianthus annuus L.	FooDB	FooDB
Helianthus tuberosus	FooDB	FooDB
Hibiscus sabbariffa	FooDB	FooDB
Hippophae rhamnoides	FooDB	FooDB
Hordeum vulgare	FooDB	FooDB
Hyssopus officinalis L.	FooDB	FooDB
Illicium verum	FooDB	FooDB
Ipomoea aquatica	FooDB	FooDB
Ipomoea batatas	FooDB	FooDB
Juglans	FooDB	FooDB
Juglans ailanthifolia	FooDB	FooDB
Juglans cinerea	FooDB	FooDB
Juglans nigra L.	FooDB	FooDB
Juglans regia	FooDB	FooDB
Lablab purpureus	FooDB	FooDB
Lactuca sativa	FooDB	FooDB
Lagenaria siceraria	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Lathyrus sativus	FooDB	FooDB
Laurus nobilis L.	FooDB	FooDB
Lens culinaris	FooDB	FooDB
Lentinus edodes	FooDB	FooDB
Lepidium sativum	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Levisticum officinale	FooDB	FooDB
Linum usitatissimum	FooDB	FooDB
Litchi chinensis	FooDB	FooDB
Luffa aegyptiaca	FooDB	FooDB
Lupinus	FooDB	FooDB
Lupinus albus	FooDB	FooDB
Macadamia	FooDB	FooDB
Macadamia tetraphylla	FooDB	FooDB
Malpighia emarginata	FooDB	FooDB
Malus	FooDB	FooDB
Malus pumila	FooDB	FooDB
Mammea americana	FooDB	FooDB
Mangifera indica	FooDB	FooDB
Manihot esculenta	FooDB	FooDB
Manilkara zapota	FooDB	FooDB
Maranta arundinacea	FooDB	FooDB
Matricaria recutita	FooDB	FooDB
Matteuccia struthiopteris	FooDB	FooDB
Medicago sativa	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Melissa officinalis L.	FooDB	FooDB
Mentha	FooDB	FooDB
Mentha aquatica	FooDB	FooDB
Mentha arvensis	FooDB	FooDB
Mentha spicata	FooDB	FooDB
Mentha x piperita	FooDB	FooDB
Mespilus germanica	FooDB	FooDB
Metroxylon sagu	FooDB	FooDB
Momordica charantia	FooDB	FooDB
Morchellaceae	FooDB	FooDB
Morella rubra	FooDB	FooDB
Moringa oleifera	FooDB	FooDB
Morus	FooDB	FooDB
Morus nigra	FooDB	FooDB
Mus musculus	LOTUS Database	35616633
Musa acuminata	FooDB	FooDB
Musa x paradisiaca	FooDB	FooDB
Myrica	FooDB	FooDB
Myristica fragrans	FooDB	FooDB
Nelumbo	FooDB	FooDB
Nelumbo nucifera	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Nephelium lappaceum	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Nuphar lutea	FooDB	FooDB
Ocimum basilicum	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oenothera biennis	FooDB	FooDB
Olea europaea	FooDB	FooDB
Opuntia	FooDB	FooDB
Opuntia cochenillifera	FooDB	FooDB
Opuntia macrorhiza	FooDB	FooDB
Origanum majorana	FooDB	FooDB
Origanum onites	FooDB	FooDB
Origanum vulgare	FooDB	FooDB
Origanum X majoricum	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Oryza rufipogon	FooDB	FooDB
Oryza sativa	FooDB	FooDB
Ovis aries	FooDB	FooDB
Pachyrhizus erosus	FooDB	FooDB
Panax ginseng	FooDB	FooDB
Pangium edule	FooDB	FooDB
Panicum miliaceum	FooDB	FooDB
Passiflora edulis	FooDB	FooDB
Pastinaca sativa	FooDB	FooDB
Pediomelum esculentum	FooDB	FooDB
Perideridia oregana	FooDB	FooDB
Persea americana	FooDB	FooDB
Petasites japonicus	FooDB	FooDB
Petroselinum crispum	FooDB	FooDB
Phaseolus coccineus	FooDB	FooDB
Phaseolus lunatus	FooDB	FooDB
Phaseolus vulgaris	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Phoenix dactylifera	FooDB	FooDB
Photinia melanocarpa	FooDB	FooDB
Phyllostachys edulis	FooDB	FooDB
Physalis	FooDB	FooDB
Physalis philadelphica var. immaculata	FooDB	FooDB
Phytolacca americana	FooDB	FooDB
Pimenta dioica	FooDB	FooDB
Pimpinella anisum	FooDB	FooDB
Pinus	FooDB	FooDB
Pinus edulis	FooDB	FooDB
Piper nigrum L.	FooDB	FooDB
Pistacia vera	FooDB	FooDB
Pisum sativum	FooDB	FooDB
Pleurotus ostreatus	FooDB	FooDB
Polygonum alpinum	FooDB	FooDB
Portulaca oleracea	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Pouteria sapota	FooDB	FooDB
Prunus armeniaca	FooDB	FooDB
Prunus avium	FooDB	FooDB
Prunus avium L.	FooDB	FooDB
Prunus cerasus	FooDB	FooDB
Prunus domestica	FooDB	FooDB
Prunus dulcis	FooDB	FooDB
Prunus persica	FooDB	FooDB
Prunus persica var. nucipersica	FooDB	FooDB
Prunus persica var. persica	FooDB	FooDB
Prunus tomentosa	FooDB	FooDB
Prunus virginiana	FooDB	FooDB
Psidium cattleianum	FooDB	FooDB
Psidium guajava	FooDB	FooDB
Psophocarpus tetragonolobus	FooDB	FooDB
Punica granatum	FooDB	FooDB
Pyrus communis	FooDB	FooDB
Pyrus pyrifolia	FooDB	FooDB
Quercus	FooDB	FooDB
Raphanus sativus	FooDB	FooDB
Raphanus sativus var. longipinnatus	FooDB	FooDB
Raphanus sativus var. sativus	FooDB	FooDB
Rheum rhabarbarum	FooDB	FooDB
Ribes aureum	FooDB	FooDB
Ribes glandulosum	FooDB	FooDB
Ribes nigrum	FooDB	FooDB
Ribes rubrum	FooDB	FooDB
Ribes uva-crispa	FooDB	FooDB
Rosa	FooDB	FooDB
Rubus arcticus	FooDB	FooDB
Rubus chamaemorus	FooDB	FooDB
Rubus idaeus	FooDB	FooDB
Rubus occidentalis	FooDB	FooDB
Rubus spectabilis	FooDB	FooDB
Rumex	FooDB	FooDB
Rumex acetosa	FooDB	FooDB
Rumex articus	FooDB	FooDB
Sagittaria latifolia	FooDB	FooDB
Salix pulchra	FooDB	FooDB
Salvia elegans	FooDB	FooDB
Salvia hispanica	FooDB	FooDB
Salvia officinalis	FooDB	FooDB
Salvia rosmarinus	FooDB	FooDB
Sambucus nigra	FooDB	FooDB
Sambucus nigra L.	FooDB	FooDB
Satureja hortensis L.	FooDB	FooDB
Satureja montana	FooDB	FooDB
Scorzonera hispanica	FooDB	FooDB
Secale cereale	FooDB	FooDB
Sechium edule	FooDB	FooDB
Sesamum indicum	FooDB	FooDB
Sesbania bispinosa	FooDB	FooDB
Sinapis alba	FooDB	FooDB
Sisymbrium	FooDB	FooDB
Solanum lycopersicum	FooDB	FooDB
Solanum lycopersicum var. cerasiforme	FooDB	FooDB
Solanum lycopersicum var. lycopersicum	FooDB	FooDB
Solanum melongena	FooDB	FooDB
Solanum quitoense	FooDB	FooDB
Solanum tuberosum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Sorbus aucuparia	FooDB	FooDB
Sorghum bicolor	FooDB	FooDB
Spinacia oleracea	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB
Synechococcus elongatus	LOTUS Database	35616633
Syzygium aromaticum	FooDB	FooDB
Syzygium cumini	FooDB	FooDB
Syzygium jambos	FooDB	FooDB
Tamarindus indica	FooDB	FooDB
Taraxacum officinale	FooDB	FooDB
Tetragonia tetragonioides	FooDB	FooDB
Thelesperma	FooDB	FooDB
Thymus pulegioides	FooDB	FooDB
Thymus vulgaris	FooDB	FooDB
Tilia cordata	FooDB	FooDB
Tilia L.	FooDB	FooDB
Tragopogon porrifolius	FooDB	FooDB
Trigonella foenum-graecum	FooDB	FooDB
Triticum	FooDB	FooDB
Triticum aestivum	FooDB	FooDB
Triticum durum	FooDB	FooDB
Triticum spelta	FooDB	FooDB
Triticum turanicum	FooDB	FooDB
Trypanosoma brucei	LOTUS Database	35616633
Typha angustifolia	FooDB	FooDB
Vaccinium	FooDB	FooDB
Vaccinium angustifolium	FooDB	FooDB
Vaccinium angustifolium X Vaccinium corymbosum	FooDB	FooDB
Vaccinium arboreum	FooDB	FooDB
Vaccinium corymbosum	FooDB	FooDB
Vaccinium deliciosum	FooDB	FooDB
Vaccinium elliottii	FooDB	FooDB
Vaccinium macrocarpon	FooDB	FooDB
Vaccinium myrtilloides	FooDB	FooDB
Vaccinium myrtillus	FooDB	FooDB
Vaccinium ovalifolium	FooDB	FooDB
Vaccinium ovatum	FooDB	FooDB
Vaccinium oxycoccos	FooDB	FooDB
Vaccinium parvifolium	FooDB	FooDB
Vaccinium reticulatum	FooDB	FooDB
Vaccinium stamineum	FooDB	FooDB
Vaccinium uliginosum	FooDB	FooDB
Vaccinium vitis-idaea	FooDB	FooDB
Valerianella locusta	FooDB	FooDB
Vanilla	FooDB	FooDB
Verbena officinalis	FooDB	FooDB
Viburnum edule	FooDB	FooDB
Vicia faba	KNApSAcK Database	22123792
Vigna aconitifolia	FooDB	FooDB
Vigna angularis	FooDB	FooDB
Vigna mungo	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vigna radiata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vigna umbellata	FooDB	FooDB
Vigna unguiculata	FooDB	FooDB
Vigna unguiculata ssp. cylindrica	FooDB	FooDB
Vigna unguiculata ssp. unguiculata	FooDB	FooDB
Vigna unguiculata var. sesquipedalis	FooDB	FooDB
Vitis	FooDB	FooDB
Vitis aestivalis	FooDB	FooDB
Vitis labrusca	FooDB	FooDB
Vitis rotundifolia	FooDB	FooDB
Vitis vinifera L.	FooDB	FooDB
Xanthosoma sagittifolium	FooDB	FooDB
Zea mays L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Zingiber officinale	FooDB	FooDB
Zizania	FooDB	FooDB
Zizania aquatica	FooDB	FooDB
Ziziphus zizyphus	FooDB	FooDB

Species Where Detected

Species Name	Source	Reference
Escherichia coli	KNApSAcK Database	22123792
Homo sapiens (Urine)	KNApSAcK Database	22123792

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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Peptides

Alternative Parents

Substituents

Alpha peptide
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid
Alpha-amino acid or derivatives
L-alpha-amino acid
Dicarboxylic acid or derivatives
Fatty acid
Amino acid or derivatives
Amino acid
Alkylthiol
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Hydrocarbon derivative
Primary aliphatic amine
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Amine
Organonitrogen compound
Organooxygen compound
Organosulfur compound
Organopnictogen compound
Primary amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

thiol (CHEBI:16856 )
L-cysteine derivative (CHEBI:16856 )
tripeptide (CHEBI:16856 )
Coenzymes (C00051 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	195 °C	Not Available
Boiling Point	754.00 to 755.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	292.5 mg/mL	Not Available
LogP	-1.645 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	-2.7	ALOGPS
logP	-4.9	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	1.94	ChemAxon
pKa (Strongest Basic)	9.22	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	158.82 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	69.11 m³·mol⁻¹	ChemAxon
Polarizability	29.11 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000125

DrugBank ID

DB00143

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

124886

PDB ID

Not Available

ChEBI ID

16856

Good Scents ID

rw1248341

References

General References

Bayir H, Kagan VE, Tyurina YY, Tyurin V, Ruppel RA, Adelson PD, Graham SH, Janesko K, Clark RS, Kochanek PM: Assessment of antioxidant reserves and oxidative stress in cerebrospinal fluid after severe traumatic brain injury in infants and children. Pediatr Res. 2002 May;51(5):571-8. [PubMed:11978879 ]
Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2:18. [PubMed:15882454 ]
Djurhuus R, Segadal K, Svardal AM: Glutathione in blood cells decreases without DNA breaks after a simulated saturation dive to 250 msw. Aviat Space Environ Med. 2006 Jun;77(6):597-604. [PubMed:16780237 ]
Hung CR: Effect of lysozyme chloride on betel quid chewing aggravated gastric oxidative stress and hemorrhagic ulcer in diabetic rats. World J Gastroenterol. 2005 Oct 7;11(37):5853-8. [PubMed:16270397 ]
Grattagliano I, Portincasa P, Palmieri VO, Palasciano G: Contribution of canalicular glutathione efflux to bile formation. From cholestasis associated alterations to pharmacological intervention to modify bile flow. Curr Drug Targets Immune Endocr Metabol Disord. 2005 Jun;5(2):153-61. [PubMed:16089347 ]
Calvo-Marzal P, Chumbimuni-Torres KY, Hoehr NF, Kubota LT: Determination of glutathione in hemolysed erythrocyte with amperometric sensor based on TTF-TCNQ. Clin Chim Acta. 2006 Sep;371(1-2):152-8. Epub 2006 May 2. [PubMed:16650398 ]
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 ]
Sohlenius-Sternbeck AK, Schmidt S: Impaired glutathione-conjugating capacity by cryopreserved human and rat hepatocytes. Xenobiotica. 2005 Jul;35(7):727-36. [PubMed:16316931 ]
Iida M, Yasuhara T, Mochizuki H, Takakura H, Yanagisawa T, Kubo H: Two Japanese brothers with hereditary gamma-glutamyl transpeptidase deficiency. J Inherit Metab Dis. 2005;28(1):49-55. [PubMed:15702405 ]
Briz O, Romero MR, Martinez-Becerra P, Macias RI, Perez MJ, Jimenez F, San Martin FG, Marin JJ: OATP8/1B3-mediated cotransport of bile acids and glutathione: an export pathway for organic anions from hepatocytes? J Biol Chem. 2006 Oct 13;281(41):30326-35. Epub 2006 Jul 28. [PubMed:16877380 ]
Czeczot H, Scibior D, Skrzycki M, Podsiad M: [Antioxidant barrier in patients with gastric cancer--preliminary study]. Pol Merkur Lekarski. 2005 Oct;19(112):521-5. [PubMed:16379316 ]
Czeczot H, Scibior D, Skrzycki M, Podsiad M: Glutathione and GSH-dependent enzymes in patients with liver cirrhosis and hepatocellular carcinoma. Acta Biochim Pol. 2006;53(1):237-42. Epub 2006 Jan 9. [PubMed:16404476 ]
Kawakami Y, Monobe M, Kuwabara K, Fujita T, Maeda M, Fujino O, Kojima S, Fukunaga Y: A comparative study of nitric oxide, glutathione, and glutathione peroxidase activities in cerebrospinal fluid from children with convulsive diseases/children with aseptic meningitis. Brain Dev. 2006 May;28(4):243-6. Epub 2006 Jan 10. [PubMed:16376049 ]
Kaynar H, Meral M, Turhan H, Keles M, Celik G, Akcay F: Glutathione peroxidase, glutathione-S-transferase, catalase, xanthine oxidase, Cu-Zn superoxide dismutase activities, total glutathione, nitric oxide, and malondialdehyde levels in erythrocytes of patients with small cell and non-small cell lung cancer. Cancer Lett. 2005 Sep 28;227(2):133-9. Epub 2005 Jan 8. [PubMed:16112416 ]
Tsai CC, Chen HS, Chen SL, Ho YP, Ho KY, Wu YM, Hung CC: Lipid peroxidation: a possible role in the induction and progression of chronic periodontitis. J Periodontal Res. 2005 Oct;40(5):378-84. [PubMed:16105090 ]
Wielandt AM, Vollrath V, Farias M, Chianale J: Bucillamine induces glutathione biosynthesis via activation of the transcription factor Nrf2. Biochem Pharmacol. 2006 Aug 14;72(4):455-62. Epub 2006 Jun 27. [PubMed:16806086 ]
Oztezcan S, Balkan J, Dogru-Abbasoglu S, Cevikbas U, Aykac-Toker G, Uysal M: Resistance of erythrocytes to lipid peroxidation in cirrhotic rats. Arch Med Res. 2005 Sep-Oct;36(5):459-63. [PubMed:16099321 ]
Schulpis KH, Papassotiriou I, Parthimos T, Tsakiris T, Tsakiris S: The effect of L-cysteine and glutathione on inhibition of Na+, K+-ATPase activity by aspartame metabolites in human erythrocyte membrane. Eur J Clin Nutr. 2006 May;60(5):593-7. [PubMed:16391576 ]
Zamek-Gliszczynski MJ, Hoffmaster KA, Nezasa K, Tallman MN, Brouwer KL: Integration of hepatic drug transporters and phase II metabolizing enzymes: mechanisms of hepatic excretion of sulfate, glucuronide, and glutathione metabolites. Eur J Pharm Sci. 2006 Apr;27(5):447-86. Epub 2006 Feb 10. [PubMed:16472997 ]
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Showing NP-Card for Glutathione (NP0001080)

MOL for NP0001080 (Glutathione)

3D MOL for NP0001080 (Glutathione)

3D SDF for NP0001080 (Glutathione)

3D-SDF for NP0001080 (Glutathione)

PDB for NP0001080 (Glutathione)

3D PDB for NP0001080 (Glutathione)

SMILES for NP0001080 (Glutathione)

INCHI for NP0001080 (Glutathione)

Structure for NP0001080 (Glutathione)

3D Structure for NP0001080 (Glutathione)