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Cystine

Synopsis, 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

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 Formula	C₆H₁₂N₂O₄S₂
Molecular Weight	240.3 g/mol
XLogP3	-6.3
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	7
Exact Mass	g/mol
Monoisotopic Mass	g/mol
Topological Polar Surface Area	177
Heavy Atom Count	14
Formal Charge	0
Complexity	192
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.