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DSSTox_CID_3101
Also known as: 70-18-8, L-glutathione, Glutathion, Isethion, L-glutathione reduced, Tathion
Molecular Formula
C10H17N3O6S
Molecular Weight
307.33  g/mol
InChI Key
RWSXRVCMGQZWBV-WDSKDSINSA-N
FDA UNII
GAN16C9B8O

A tripeptide with many roles in cells. It conjugates to drugs to make them more soluble for excretion, is a cofactor for some enzymes, is involved in protein disulfide bond rearrangement and reduces peroxides.
1 2D Structure

DSSTox_CID_3101

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-1-oxo-3-sulfanylpropan-2-yl]amino]-5-oxopentanoic acid
2.1.2 InChI
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
2.1.3 InChI Key
RWSXRVCMGQZWBV-WDSKDSINSA-N
2.1.4 Canonical SMILES
C(CC(=O)NC(CS)C(=O)NCC(=O)O)C(C(=O)O)N
2.1.5 Isomeric SMILES
C(CC(=O)N[C@@H](CS)C(=O)NCC(=O)O)[C@@H](C(=O)O)N
2.2 Other Identifiers
2.2.1 UNII
GAN16C9B8O
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Gamma L Glu L Cys Gly

2. Gamma L Glutamyl L Cysteinylglycine

3. Gamma-l-glu-l-cys-gly

4. Gamma-l-glutamyl-l-cysteinylglycine

5. Glutathione, Reduced

6. Reduced Glutathione

2.3.2 Depositor-Supplied Synonyms

1. 70-18-8

2. L-glutathione

3. Glutathion

4. Isethion

5. L-glutathione Reduced

6. Tathion

7. Reduced Glutathione

8. Glutathione-sh

9. Glutinal

10. Tathione

11. Deltathione

12. Neuthion

13. Copren

14. Glutide

15. Triptide

16. Ledac

17. Gsh

18. Glutatione

19. Glutatiol

20. Glutathione Reduced

21. Panaron

22. Glutathione Sh

23. L-glutatione

24. Agifutol S

25. Glutathione (reduced)

26. L-gamma-glutamyl-l-cysteinylglycine

27. Gamma-l-glutamyl-l-cysteinylglycine

28. Glutathione [jan]

29. L-glutathione, Reduced

30. Gamma-l-glutamyl-l-cysteinyl-glycine

31. 5-l-glutamyl-l-cysteinylglycine

32. Glutham

33. Gamma-l-glutamylcysteinylglycine

34. Glutathione Red

35. Aec Glutathione

36. Red. Glutathione

37. Bakezyme Rx

38. L-glutathione Reduce

39. Glycine, L-gamma-glutamyl-l-cysteinyl-

40. Reduced L-glutathione

41. (2s)-2-amino-5-[[(2r)-1-(carboxymethylamino)-1-oxo-3-sulfanylpropan-2-yl]amino]-5-oxopentanoic Acid

42. (s)-2-amino-5-(((r)-1-((carboxymethyl)amino)-3-mercapto-1-oxopropan-2-yl)amino)-5-oxopentanoic Acid

43. N-(n-gamma-l-glutamyl-l-cysteinyl)glycine

44. N-(n-l-gamma-glutamyl-l-cysteinyl)glycine

45. Glycine, N-(n-l-gamma-glutamyl-l-cysteinyl)-

46. Gan16c9b8o

47. L-glutamyl-l-cysteinylglycine

48. L-glutathione (reduced Form)

49. Glycine, L-.gamma.-glutamyl-l-cysteinyl-

50. Benzenamine, 2-[(4-methoxyphenyl)methoxy]-

51. Chebi:16856

52. (2s)-2-amino-4-{[(1r)-1-[(carboxymethyl)carbamoyl]-2-sulfanylethyl]carbamoyl}butanoic Acid

53. 106272-20-2

54. 95687-20-0

55. Dsstox_cid_3101

56. N-(n-l-.gamma.-glutamyl-l-cysteinyl)glycine

57. N5-((r)-1-((carboxymethyl)amino)-3-mercapto-1-oxopropan-2-yl)-l-glutamine

58. Dsstox_rid_76875

59. Dsstox_gsid_23101

60. [glu(-cys)]n-gly

61. Mfcd00065939

62. Cas-70-18-8

63. (s)-2-amino-5-((r)-1-(carboxymethylamino)-3-mercapto-1-oxopropan-2-ylamino)-5-oxopentanoic Acid

64. Glutathione, Reduced

65. Ccris 2094

66. Sr-05000002567

67. Glutathione [ban:jan]

68. Einecs 200-725-4

69. L-glutathione Reduced Form

70. Unii-gan16c9b8o

71. Nsc 400639

72. Phytochelatins

73. Readisorb

74. Glutathione;

75. Nsc400639

76. 1lbk

77. Ncgc00094976-01

78. Tathion (tn)

79. Glutathione (jp17)

80. Spectrum_000419

81. 1oe7

82. 1oe8

83. 1r4w

84. C(n-.gamma.glu-)g

85. Glutathione [ii]

86. Glutathione [mi]

87. Reduced Glutathione,(s)

88. Spectrum2_001500

89. Spectrum3_000946

90. Spectrum4_001056

91. Spectrum5_000940

92. Glutathione, Reduced Form

93. Glutathione [inci]

94. Bmse000185

95. Bmse000952

96. Bmse000956

97. Glutathione (reduced Type)

98. Glutathione [vandf]

99. Cys(n-.gamma.glu-)-gly

100. Schembl9167

101. Chembl1543

102. Glutathione [mart.]

103. Glutathione [usp-rs]

104. Glutathione [who-dd]

105. Kbiogr_001352

106. Kbioss_000899

107. Mls001333069

108. Divk1c_000075

109. Spectrum1502248

110. Spbio_001519

111. Gamma-glutamyl-cysteinyl-glycine

112. Gtpl6737

113. Dtxsid6023101

114. L-?-glutamyl-l-cysteinylglycine

115. L-glutathione Reduced, 97.0%

116. Chebi:60836

117. Hms500d17

118. Kbio1_000075

119. Kbio2_000899

120. Kbio2_003467

121. Kbio2_006035

122. Kbio3_002012

123. (gamma-glutamylcysteine)n-glycine

124. L-g-glutamyl-l-cysteinyl-glycine

125. Y-l-glutamyl-l-cysteinyl-glycine

126. L-?-glutamyl-l-cysteinyl-glycine

127. Ninds_000075

128. Glutathione [ep Monograph]

129. Hms1921n22

130. Pharmakon1600-01502248

131. Poly(gamma-glutamylcysteine)glycine

132. Hy-d0187

133. L-glutathione Reduced, >=98.0%

134. Zinc3830891

135. Gam.-l-glutamyl-l-cysteinyl-glycine

136. Tox21_111371

137. Bdbm50422268

138. Ccg-38876

139. L-gamma-glutamyl-l-cysteinyl-glycine

140. Nsc758199

141. S4606

142. Akos015999135

143. Tox21_111371_1

144. Cs-7948

145. Db00143

146. Nsc-758199

147. Sdccgmls-0066687.p001

148. .gamma.-l-glutamyl-l-cysteinyl-glycine

149. Idi1_000075

150. N-(n-l-?-glutamyl-l-cysteinyl)glycine

151. Pharm Biol 11: 539 (1968)

152. Smp1_000247

153. Ncgc00264046-02

154. Ds-14675

155. Gsh;gamma-l-glutamyl-l-cysteinyl-glycine

156. Smr000857220

157. Sbi-0051743.p002

158. L-glutathione Reduced, Bioxtra, >=98.0%

159. B7775

160. G0074

161. Glycine, N-(n-l-gamma-glutamyl-l-cysteinyl)

162. C00051

163. C02471

164. D00014

165. G-3980

166. P19615

167. Ab00443568_03

168. Glutathione 100 Microg/ml In Acetonitrile:water

169. A866658

170. Q116907

171. Sr-05000002567-1

172. Sr-05000002567-2

173. L-glutathione Reduced, Vetec(tm) Reagent Grade, >=98%

174. Z2183947556

175. Glutathione, European Pharmacopoeia (ep) Reference Standard

176. Glutathione, United States Pharmacopeia (usp) Reference Standard

177. Glutathione, Pharmaceutical Secondary Standard; Certified Reference Material

178. L-glutathione Reduced, Cell Culture Tested, Bioreagent, >=98.0%, Powder

179. (2s)-2-amino-4-{[(1r)-1-[(carboxymethyl)carbamoyl]-2-sulfanylethyl]carbamoylbutanoic Acid

180. (2s)-2-amino-5-({(2r)-1-[(carboxymethyl)amino]-1-oxo-3-sulfanyl-2-propanyl}amino)-5-oxopentanoic Acid

181. Glutathione; L-glutathione Reduced; 5-l-glutamyl-l-cysteinylglycine; Gamma-l-glutamyl-l-cysteinylglycine; Gsh

2.4 Create Date
2005-06-08
3 Chemical and Physical Properties
Molecular Weight 307.33 g/mol
Molecular Formula C10H17N3O6S
XLogP3-4.5
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count8
Rotatable Bond Count9
Exact Mass307.08380644 g/mol
Monoisotopic Mass307.08380644 g/mol
Topological Polar Surface Area160 Ų
Heavy Atom Count20
Formal Charge0
Complexity389
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

For nutritional supplementation, also for treating dietary shortage or imbalance


5 Pharmacology and Biochemistry
5.1 ATC Code

V - Various

V03 - All other therapeutic products

V03A - All other therapeutic products

V03AB - Antidotes

V03AB32 - Glutathione


5.2 Absorption, Distribution and Excretion

Absorption

Research suggests that glutathione is not orally bioactive, and that very little of oral glutathione tablets or capsules is actually absorbed by the body.


5.3 Mechanism of Action

Glutathione (GSH) participates in leukotriene synthesis and is a cofactor for the enzyme glutathione peroxidase. It also plays a role in the hepatic biotransformation and detoxification process; it acts as a hydrophilic molecule that is added to other lipophilic toxins or wastes prior to entering biliary excretion. It participates in the detoxification of methylglyoxal, a toxic by-product of metabolism, mediated by glyoxalase enzymes. Glyoxalase I catalyzes the conversion of methylglyoxal and reduced glutathione to S-D-Lactoyl-glutathione. Glyoxalase II catalyzes the conversion of S-D-Lactoyl Glutathione to Reduced Glutathione and D-lactate. Glyoxalase I catalyzes the conversion of methylglyoxal and reduced glutathione to S-D-Lactoyl-glutathione. Glyoxalase II catalyzes the conversion of S-D-Lactoyl Glutathione to Reduced Glutathione and D-lactate. GSH is a cofactor of conjugation and reduction reactions that are catalyzed by glutathione S-transferase enzymes expressed in the cytosol, microsomes, and mitochondria. However, it is capable of participating in non-enzymatic conjugation with some chemicals, as it is hypothesized to do to a significant extent with n-acetyl-p-benzoquinone imine (NAPQI), the reactive cytochrome P450 reactive metabolite formed by toxic 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 sulfhydryl groups which would otherwise be toxically adducted. The preferred medical treatment to an overdose of this nature, whose efficacy has been consistently supported in literature, is the administration (usually in atomized form) of N-acetylcysteine, which is used by cells to replace spent GSSG and allow a usable GSH pool.


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