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Chemistry

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Also known as: L-cystine, 56-89-3, L-cystin, L-dicysteine, Cysteine disulfide, Cystin
Molecular Formula
C6H12N2O4S2
Molecular Weight
240.3  g/mol
InChI Key
LEVWYRKDKASIDU-IMJSIDKUSA-N
FDA UNII
48TCX9A1VT

Cystine
A covalently linked dimeric nonessential amino acid formed by the oxidation of CYSTEINE. Two molecules of cysteine are joined together by a disulfide bridge to form cystine.
1 2D Structure

Cystine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2R)-2-amino-3-[[(2R)-2-amino-2-carboxyethyl]disulfanyl]propanoic acid
2.1.2 InChI
InChI=1S/C6H12N2O4S2/c7-3(5(9)10)1-13-14-2-4(8)6(11)12/h3-4H,1-2,7-8H2,(H,9,10)(H,11,12)/t3-,4-/m0/s1
2.1.3 InChI Key
LEVWYRKDKASIDU-IMJSIDKUSA-N
2.1.4 Canonical SMILES
C(C(C(=O)O)N)SSCC(C(=O)O)N
2.1.5 Isomeric SMILES
C([C@@H](C(=O)O)N)SSC[C@@H](C(=O)O)N
2.2 Other Identifiers
2.2.1 UNII
48TCX9A1VT
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Copper Cystinate

2. L Cystine

3. L-cystine

2.3.2 Depositor-Supplied Synonyms

1. L-cystine

2. 56-89-3

3. L-cystin

4. L-dicysteine

5. Cysteine Disulfide

6. Cystin

7. Beta,beta'-dithiodialanine

8. L-cysteine Disulfide

9. 1-cystine

10. 3,3'-dithiodialanine

11. Cystine, L-

12. Dicysteine

13. Cystine (l)-

14. Cystine Acid

15. (h-cys-oh)2

16. Alanine, 3,3'-dithiodi-

17. Alanine, 3,3'-dithiobis-

18. Beta,beta'-dithioalanine, L-

19. L-alanine, 3,3'-dithiobis-

20. 3,3'-dithiobis(2-aminopropanoic Acid)

21. Cystine (van)

22. Cystine [usan]

23. Cystin (van)

24. L-(-)-cystine

25. (-)-cystine

26. Gelucystine

27. Ccris 5822

28. L-alpha-diamino-beta-dithiolactic Acid

29. Cystine,d

30. Bis(beta-amino-beta-carboxyethyl)disulfide

31. Unii-48tcx9a1vt

32. 3,3'-dithiobis-l-alanine

33. Einecs 200-296-3

34. (r-(r*,r*))-3,3'-dithiobis(2-aminopropanoic Acid)

35. 48tcx9a1vt

36. Nsc 13203

37. Beta,beta'-diamino-beta,beta'-dicarboxydiethyl Disulfide

38. Brn 1728094

39. Dtxsid2046418

40. Chebi:16283

41. Ai3-09064

42. Beta,beta'-diamino-beta,beta'-dicarboxydiethyldisulfide

43. Cystine [usan:inn]

44. (2r,2'r)-3,3'-disulfanediylbis(2-aminopropanoic Acid)

45. 3,3'-dithiobis(2-aminopropanoic Acid), (r-(r*,r*))-

46. Propanoic Acid, 3,3'-dithiobis(2-amino-, (r-(r*,r*))-

47. Nsc-13203

48. S-cysteinyl Cysteine

49. Bis(beta-amino-beta-carboxyethyl) Disulfide

50. Dtxcid0026418

51. Ec 200-296-3

52. (2r)-2-amino-3-{[(2r)-2-amino-2-carboxyethyl]disulfanyl}propanoic Acid

53. 4-04-00-03155 (beilstein Handbook Reference)

54. Cystine (l-cystine)

55. C6h12n2o4s2

56. E921

57. Cystine (mart.)

58. Cystine [mart.]

59. Cystine (usp-rs)

60. Cystine [usp-rs]

61. (r,r)-3,3'-dithiobis(2-aminopropanoic Acid)

62. S-(((r)-2-amino-2-carboxyethyl)thio)cysteine

63. Cistina

64. Zystin

65. Cystin-

66. Cystine (ep Monograph)

67. Cystine [ep Monograph]

68. 3,3-disulfanediylbis((2r)-2-aminopropanoic Acid)

69. 2-amino-3-(2-amino-2-carboxy-ethyl)disulfanyl-propanoic Acid

70. L-cystin-

71. Alpha-diamino-beta-dithiolactic Acid

72. (r-(r*,r*))-3,3'-dithiobis

73. [r-(r*,r*)]-3,3'-dithiobis

74. Mfcd00064228

75. L Cystine

76. (2r)-2-amino-3-[[(2r)-2-amino-2-carboxyethyl]disulfanyl]propanoic Acid

77. Cas-56-89-3

78. 2079930-29-1

79. Tyrosine Impurity C (ep Impurity)

80. Tyrosine Impurity C [ep Impurity]

81. (r,r)-3,3'-dithiobis(2-aminopropionicacid)

82. Acetylcysteine Impurity A (ep Impurity)

83. Acetylcysteine Impurity A [ep Impurity]

84. 24645-67-8

85. [r-(r*,r*)]-3,3'-dithiobis[2-aminopropanoic Acid]

86. Cystinum

87. Dtxsid50859005

88. C6-h12-n2-o4-s2

89. Ncgc00164531-01

90. Iyy

91. 3,3'-dithiobis

92. B,b'-dithiodialanine

93. L-cystine (9ci)

94. Cystine (usan/inn)

95. L-cystine (jp17)

96. Cystine [vandf]

97. Cystine [inci]

98. Cystine [inn]

99. Cystine [mi]

100. L-cystine [fcc]

101. L-cystine [jan]

102. Cystine, L- (8ci)

103. Cystine [who-dd]

104. Bmse000035

105. D0v1cp

106. (2r)-2-amino-3-[[(2r)-2-amino-2-carboxy-ethyl]disulfanyl]propanoic Acid

107. Beta,beta'-dithiobisalanine

108. Schembl10226

109. L-cystine, Non-animal Source

110. Chembl590540

111. Gtpl5413

112. (h-cys-oh)2 (disulfide Bond)

113. Dtxcid60210087

114. Hy-n0394

115. Tox21_112162

116. Ccg-36355

117. L-cystine, >=99.7% (tlc)

118. S4808

119. Bis(b-amino-b-carboxyethyl) Disulfide

120. Cystine, Nist(r) Srm(r) 143d

121. Akos015898645

122. Tox21_112162_1

123. Am81644

124. Db00138

125. (2r)-2-azanyl-3-[[(2r)-2-azanyl-3-oxidanyl-3-oxidanylidene-propyl]disulfanyl]propanoic Acid

126. Bis(b-amino-beta-carboxyethyl) Disulfide

127. Ncgc00166006-01

128. Ncgc00166006-02

129. Ac-11189

130. As-12654

131. D(+)-3,3'-dithiobis(2-aminopropanoate

132. L-cystine, >=98% (tlc), Crystalline

133. L-cystine, Bioultra, >=99.5% (t)

134. Ls-59051

135. L-cystine, Saj Special Grade, >=99.0%

136. L-cystine, Vetec(tm) Reagent Grade, 98%

137. Acetylcysteine Impurity A (l-cystine)

138. B,b'-diamino-b,b'-dicarboxydiethyl Disulfide

139. Cs-0008930

140. D(+)-3,3'-dithiobis(2-aminopropanoic Acid

141. (r,r)-3,3'-dithiobis(2-aminopropionic Acid)

142. C00491

143. D03636

144. En300-174654

145. M06021

146. Q408626

147. 3,3'-disulfanediylbis((2r)-2-aminopropanoic Acid)

148. 3,3'-dithiobis[2-amino-[r-(r*,r*)]-propanoate

149. 2-amino-3-[(2-amino-2-carboxyethyl)dithio]propanoate

150. L-cystine, Certified Reference Material, Tracecert(r)

151. 3,3'-dithiobis[2-amino-[r-(r*,r*)]-propanoic Acid

152. Cystine, European Pharmacopoeia (ep) Reference Standard

153. Z1269145231

154. 2-amino-3-(2-amino-2-carboxy-ethyl)disulfanyl-propanoate

155. 2-amino-3-[(2-amino-2-carboxyethyl)dithio]propanoic Acid

156. Dd82f461-3f8f-4624-9e2c-0272a9fa79ed

157. Cystine, United States Pharmacopeia (usp) Reference Standard

158. L-cystine, Cell Culture Reagent (h-l-cys(1)-oh.h-l-cys(1)-oh)

159. L-cystine, Pharmaceutical Secondary Standard; Certified Reference Material

160. L-cystine, Produced By Wacker Chemie Ag, Burghausen, Germany, >=98.5%

161. L-cystine, From Non-animal Source, Meets Ep Testing Specifications, Suitable For Cell Culture, 98.5-101.0%

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 240.3 g/mol
Molecular Formula C6H12N2O4S2
XLogP3-6.3
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count8
Rotatable Bond Count7
Exact Mass g/mol
Monoisotopic Mass g/mol
Topological Polar Surface Area177
Heavy Atom Count14
Formal Charge0
Complexity192
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

It has been claimed that L-cysteine has anti-inflammatory properties, that it can protect against various toxins, and that it might be helpful in osteoarthritis and rheumatoid arthritis. More research will have to be done before L-cysteine can be indicated for any of these conditions. Research to date has mostly been in animal models.


5 Pharmacology and Biochemistry
5.1 Mechanism of Action

Certain conditions, e.g. an acetaminophen overdose, deplete hepatic glutathione and subject the tissues to oxidative stress resulting in loss of cellular integrity. L-Cystine serves as a major precursor for synthesis of glutathione.


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