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Also known as: 150080-09-4, Val-boropro, Talabostat (mesylate), Talabostat mesilate, Talabostat mesylate [usan], Methanesulfonic acid ((r)-1-((s)-2-amino-3-methylbutanoyl)pyrrolidin-2-yl)boronic acid (1:1)

Molecular Formula

C₁₀H₂₃BN₂O₆S

Molecular Weight

310.18 g/mol

InChI Key

OXYYOEIGQRXGPI-WSZWBAFRSA-N

FDA UNII

V8ZG4Y1B51

Talabostat Mesylate is the mesylate salt of an orally active small molecule with antineoplastic and hematopoiesis- stimulating activities. By cleaving N-terminal Xaa-Pro or Xaa-Ala residues, talabostat inhibits dipeptidyl peptidases, such as fibroblast activation protein (FAP), resulting in the stimulation of cytokine and chemokine production and specific T-cell immunity and T-cell dependent activity. This agent may also stimulate the production of colony stimulating factors, such as granulocyte colony stimulating factor (G-CSF), resulting in the stimulation of hematopoiesis. Dipeptidyl peptidases are involved in the activation of polypeptide hormones and chemokines.

1 2D Structure

Talabostat Mesylate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(2R)-1-[(2S)-2-amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid;methanesulfonic acid

2.1.2 InChI

InChI=1S/C9H19BN2O3.CH4O3S/c1-6(2)8(11)9(13)12-5-3-4-7(12)10(14)15;1-5(2,3)4/h6-8,14-15H,3-5,11H2,1-2H3;1H3,(H,2,3,4)/t7-,8-;/m0./s1

2.1.3 InChI Key

OXYYOEIGQRXGPI-WSZWBAFRSA-N

2.1.4 Canonical SMILES

B(C1CCCN1C(=O)C(C(C)C)N)(O)O.CS(=O)(=O)O

2.1.5 Isomeric SMILES

B([C@@H]1CCCN1C(=O)[C@H](C(C)C)N)(O)O.CS(=O)(=O)O

2.2 Other Identifiers

2.2.1 UNII

V8ZG4Y1B51

2.3 Synonyms

2.3.1 MeSH Synonyms

1. L-valinyl-l-boroproline

2. Pt 100

3. Pt-100

4. Pt100 Cpd

5. Talabostat

6. Valinyl-boroproline

2.3.2 Depositor-Supplied Synonyms

1. 150080-09-4

2. Val-boropro

3. Talabostat (mesylate)

4. Talabostat Mesilate

5. Talabostat Mesylate [usan]

6. Methanesulfonic Acid ((r)-1-((s)-2-amino-3-methylbutanoyl)pyrrolidin-2-yl)boronic Acid (1:1)

7. Pt-100

8. Talabostat Mesylate (usan)

9. V8zg4y1b51

10. Pt100

11. 150080-09-4 (mesylate)

12. [(2r)-1-[(2s)-2-amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic Acid Mesylate

13. ((2r)-1-((2s)-2-amino-3-methylbutanoyl)pyrrolidin-2-yl)boronic Acid Methanesulfonate

14. (r)-1-((s)-2-amino-3-methylbutanoyl)pyrrolidin-2-ylboronic Acid Methanesulfonic Acid (1:1)

15. Methanesulfonic Acid ((r)-1-((s)-2-amino-3-methyl-butanoyl)pyrrolidin-2-yl)boronic Acid (1:1)

16. Unii-v8zg4y1b51

17. Talabostatmesylate

18. Methanesulfonic Acid Compound With ((r)-1-((s)-2-amino-3-methylbutanoyl)pyrrolidin-2-yl)boronic Acid (1:1)

19. Talabostat Methanesulfonic Acid

20. Bxcl 701

21. Schembl4782073

22. Chembl3545064

23. Dtxsid70164466

24. [(2r)-1-[(2s)-2-amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic Acid;methanesulfonic Acid

25. Amy14815

26. Bcp04652

27. Ex-a2166

28. Hy-13233a

29. Mfcd13194906

30. S8455

31. Talabostat (val-boropro, Pt-100)

32. Akos016000622

33. Bcp9000205

34. Cs-3187

35. Ac-35958

36. As-73355

37. Talabostat Mesylate; Val-boropro; Pt100

38. Bcp0726000045

39. B3941

40. A14080

41. D05990

42. H11715

43. Val-boropro; Pt100; Pt 100; Pt-100

44. 080t094

45. A903812

46. Q27291679

47. [(2r)-1-[(2s)-2-amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic Acid; Methanesulfonic Acid

48. [(2r)-1-[(2s)-2-amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic Acidmesylate

49. B-[(2r)-1-[(2s)-2-amino-3-methyl-1-oxobutyl]-2-pyrrolidinyl]boronic Acid Methanesulfonate

50. ((2r)-1-((2s)-2-amino-3-methylbutanoyl)pyrrolidin-2-yl)boronic Acid Methanesulphonate

51. Boronic Acid, ((2r)-1-((2s)-2-amino-3-methyl-1-oxobutyl)-2-pyrrolidinyl) Monomethanesulfonate

52. Boronic Acid, ((2r)-1-((2s)-2-amino-3-methyl-1-oxobutyl)-2-pyrrolidinyl) Monomethanesulphonate

53. Boronic Acid, ((2r)-1-((2s)-2-amino-3-methyl-1-oxobutyl)-2-pyrrolidinyl)-, Monomethanesulfonate

2.4 Create Date

2006-10-26

3 Chemical and Physical Properties

Molecular Formula	C₁₀H₂₃BN₂O₆S
Molecular Weight	310.18 g/mol
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	3
Exact Mass	310.1369878 g/mol
Monoisotopic Mass	310.1369878 g/mol
Topological Polar Surface Area	150 Å²
Heavy Atom Count	20
Formal Charge	0
Complexity	328
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	2