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Chemistry

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Also known as: 26046-90-2, 3-(methylseleno)-l-alanine, Methylselenocysteine, (r)-2-amino-3-(methylselanyl)propanoic acid, Se-methyl-l-selenocysteine, L-alanine, 3-(methylseleno)-

Molecular Formula

C₄H₉NO₂Se

Molecular Weight

182.09 g/mol

InChI Key

XDSSPSLGNGIIHP-VKHMYHEASA-N

FDA UNII

TWK220499Z

Methylselenocysteine is a naturally occurring organoselenium compound found in many plants, including garlic, onions, and broccoli, with potential antioxidant and chemopreventive activities. Se-Methyl-seleno-L-cysteine (MSC) is an amino acid analogue of cysteine in which a methylselenium moiety replaces the sulphur atom of cysteine. This agent acts as an antioxidant when incorporated into glutathione peroxidase and has been shown to exhibit potent chemopreventive activity in animal models.

1 2D Structure

Methylselenocysteine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2R)-2-amino-3-methylselanylpropanoic acid

2.1.2 InChI

InChI=1S/C4H9NO2Se/c1-8-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m0/s1

2.1.3 InChI Key

XDSSPSLGNGIIHP-VKHMYHEASA-N

2.1.4 Canonical SMILES

C[Se]CC(C(=O)O)N

2.1.5 Isomeric SMILES

C[Se]C[C@@H](C(=O)O)N

2.2 Other Identifiers

2.2.1 UNII

TWK220499Z

2.3 Synonyms

2.3.1 MeSH Synonyms

1. L-methyl-selenocysteine

2. Methyl Selenocysteine

3. Methylselenocysteine

4. Se-methyl-selenocysteine

5. Selenohomocysteine

6. Selenomethylselenocysteine

7. Selenomethylselenocysteine, (d,l)-isomer

8. Selenomethylselenocysteine, (l)-isomer

9. Selenomethylselenocysteine, (l)-isomer, 75se-labeled

10. Semcys

2.3.2 Depositor-Supplied Synonyms

1. 26046-90-2

2. 3-(methylseleno)-l-alanine

3. Methylselenocysteine

4. (r)-2-amino-3-(methylselanyl)propanoic Acid

5. Se-methyl-l-selenocysteine

6. L-alanine, 3-(methylseleno)-

7. Selenium-methylselenocystine

8. Se-methyl-seleno-l-cysteine

9. Se-methylseleno-l-cysteine

10. Se-methyl-selenocysteine

11. (2r)-2-amino-3-methylselanylpropanoic Acid

12. Chebi:27812

13. Twk220499z

14. 2-amino-3-methylselenyl Propionic Acid

15. Selenomethylselenocysteine

16. (2r)-2-amino-3-(methylselanyl)propanoic Acid

17. Se-msc

18. Semcys

19. Ccris 5465

20. Methylseleno-l-cysteine

21. L-se-methylselenocysteine

22. Unii-twk220499z

23. Msec

24. Semsc

25. L-methylselenocysteine

26. Se Msc

27. Methyl-l-selenocysteine

28. Cysteine, Seleno-methyl-

29. Lopac0_000799

30. 3-(methylselanyl)-l-alanine

31. Chembl62382

32. Schembl420015

33. Se-(methyl)seleno-l-cysteine

34. Methylselenocysteine, L-

35. L-selenomethylcysteine 0.5% Tr

36. Dtxsid801020160

37. Methylselenocysteine [who-dd]

38. Mfcd00800565

39. Akos016005152

40. Ccg-204883

41. Db12697

42. Sdccgsbi-0050776.p002

43. Ncgc00162258-01

44. Ncgc00162258-02

45. Alanine, 3-(methylselenyl)-, L-

46. Hy-114245

47. (r)-2-amino-3-(methylselanyl)propanoicacid

48. Cs-0080570

49. C05689

50. D95282

51. 046s902

52. J-016235

53. Q21099600

54. 06e70014-448a-45cd-9af1-4c0b9cf51c14

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₄H₉NO₂Se
Molecular Weight	182.09 g/mol
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	3
Exact Mass	182.97985 g/mol
Monoisotopic Mass	182.97985 g/mol
Topological Polar Surface Area	63.3 Å²
Heavy Atom Count	8
Formal Charge	0
Complexity	86.1
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Anticarcinogenic Agents

Agents that reduce the frequency or rate of spontaneous or induced tumors independently of the mechanism involved. (See all compounds classified as Anticarcinogenic Agents.)

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