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Ubenimex

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Chemistry

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Also known as: Bestatin, 58970-76-6, (s)-2-((2s,3r)-3-amino-2-hydroxy-4-phenylbutanamido)-4-methylpentanoic acid, Ubenimex (bestatin), Nk-421, (-)-bestatin

Molecular Formula

C₁₆H₂₄N₂O₄

Molecular Weight

308.37 g/mol

InChI Key

VGGGPCQERPFHOB-RDBSUJKOSA-N

FDA UNII

I0J33N5627

Ubenimex is a microbial metabolite and dipeptide with potential immunomodulatory and antitumor activities. Ubenimex competitively inhibits many aminopeptidases, including B, N and leucine aminopeptidases. Aminopeptidases has been implicated in the process of cell adhesion and invasion of tumor cells. Therefore, inhibiting aminopeptidases may partially attribute to the antitumor effect of ubenimex. This agent also activates T lymphocyte, macrophage and bone marrow stem cell as well as stimulates release of interleukin-1 and -2, thus further enhances its antitumor activity.

1 2D Structure

ubenimex

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-2-[[(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl]amino]-4-methylpentanoic acid

2.1.2 InChI

InChI=1S/C16H24N2O4/c1-10(2)8-13(16(21)22)18-15(20)14(19)12(17)9-11-6-4-3-5-7-11/h3-7,10,12-14,19H,8-9,17H2,1-2H3,(H,18,20)(H,21,22)/t12-,13+,14+/m1/s1

2.1.3 InChI Key

VGGGPCQERPFHOB-RDBSUJKOSA-N

2.1.4 Canonical SMILES

CC(C)CC(C(=O)O)NC(=O)C(C(CC1=CC=CC=C1)N)O

2.1.5 Isomeric SMILES

CC(C)C[C@@H](C(=O)O)NC(=O)[C@H]([C@@H](CC1=CC=CC=C1)N)O

2.2 Other Identifiers

2.2.1 UNII

I0J33N5627

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (3-amino-2-hydroxy-4-phenylbutanoyl)-l-leucine

2. (s-(r*,s*))-n-(3-amino-2-hydroxy-4-phenylbutyroyl)-l-leucine

3. 3-amino-2-hydroxy-4-phenylbutyryl-l-leucine

4. Bestatin

5. Bestatin, (d-leu)-(r-(r*,r*))-isomer

6. Bestatin, (d-leu)-(r-(r*,s*))-isomer

7. Bestatin, (d-leu)-(s-(r*,s*))-isomer

8. Bestatin, (l-leu)-(r-(r*,r*))-isomer

9. Bestatin, (l-leu)-(r-(r*,s*))-isomer

10. Bestatin, (l-leu)-(s-(r*,r*))-isomer

11. Bestatin, (l-leu)-(s-(r*,s*))-isomer, Hydrochloride

2.3.2 Depositor-Supplied Synonyms

1. Bestatin

2. 58970-76-6

3. (s)-2-((2s,3r)-3-amino-2-hydroxy-4-phenylbutanamido)-4-methylpentanoic Acid

4. Ubenimex (bestatin)

5. Nk-421

6. (-)-bestatin

7. N-[(2s,3r)-3-amino-2-hydroxy-4-phenylbutyryl]-l-leucine

8. Chembl29292

9. N-[(2s,3r)-3-amino-2-hydroxy-1-oxo-4-phenylbutyl]-l-leucine

10. 58970-76-6 (free Base)

11. I0j33n5627

12. Nsc-265489

13. ((2s,3r)-3-amino-2-hydroxy-4-phenylbutanoyl)-l-leucine

14. L-leucine, N-[(2s,3r)-3-amino-2-hydroxy-1-oxo-4-phenylbutyl]-

15. Mfcd00083262

16. (2s)-2-[(2s,3r)-3-amino-2-hydroxy-4-phenylbutanamido]-4-methylpentanoic Acid

17. 2-(3-amino-2-hydroxy-4-phenyl-butyrylamino)-4-methyl-pentanoic Acid

18. Ubenimexum [latin]

19. Ubenimexum

20. Ubenimex [inn:jan]

21. Smr000059165

22. (2s)-2-[[(2s,3r)-3-amino-2-hydroxy-4-phenylbutanoyl]amino]-4-methylpentanoic Acid

23. Einecs 261-529-2

24. Nk 421

25. Nsc 265489

26. Brn 4704312

27. Ubestatin

28. Ubenimex, Solid

29. L-leucine, N-((2s,3r)-3-amino-2-hydroxy-1-oxo-4-phenylbutyl)-

30. Unii-i0j33n5627

31. 1txr

32. Ubenimex- Bio-x

33. Ubenimex(bestatin)

34. Ubenimex, Bestatin

35. Ubenimex,(s)

36. 3-(r)-amino-2-(s)-hydroxy-4-phenylbutanoyl-(s)-leucine

37. Ubenimex [inn]

38. Ubenimex [jan]

39. Ubenimex [mi]

40. Ubenimex [mart.]

41. Ubenimex [who-dd]

42. Schembl7944

43. (3-amino-2-hydroxy-4-phenylbutanoyl)-l-leucine

44. Lopac0_000214

45. Bspbio_001553

46. Kbiogr_000273

47. Kbioss_000273

48. Mls000028649

49. Mls001424177

50. Mls006010137

51. Bcbcmap01_000178

52. Bdbm23971

53. Kbio2_000273

54. Kbio2_002841

55. Kbio2_005409

56. Kbio3_000545

57. Kbio3_000546

58. Bio2_000273

59. Bio2_000753

60. Hms1361n15

61. Hms1791n15

62. Hms1989n15

63. Hms2052a03

64. Hms2232h13

65. Hms3268o06

66. Hms3402n15

67. Hms3412n16

68. Hms3676n16

69. Hms3715b20

70. (-)-n-((2s,3r)-3-amino-2-hydroxy-4-phenylbutyryl)-l-leucine

71. (s-(r*,s*))-n-(3-amino-2-hydroxy-4-phenylbutyroyl)-l-leucine

72. Ex-a1292

73. Hy-b0134

74. Zinc1542895

75. Bdbm50367209

76. Nsc779839

77. S1591

78. Akos016339610

79. L-leucine, N-(3-amino-2-hydroxy-1-oxo-4-phenylbutyl)-, (s-(r*,s*))-

80. Ccg-101071

81. Cs-1910

82. Db03424

83. Ks-5207

84. Nc00321

85. Nsc-779839

86. Sdccgsbi-0050202.p003

87. Idi1_034023

88. Smp1_000030

89. Ncgc00025323-01

90. Ncgc00025323-02

91. Ncgc00025323-03

92. Ncgc00025323-04

93. Ncgc00025323-05

94. Ncgc00025323-06

95. Ncgc00025323-08

96. Ncgc00025323-14

97. Bu164499

98. Bcp0726000308

99. U0111

100. Ab00698345_05

101. 970b766

102. A832093

103. Sr-01000075724-3

104. W-105351

105. [(2s,3r)-3-amino-2-hydroxy-4-phenylbutanoyl]-leu

106. Brd-k59574735-001-02-7

107. Brd-k59574735-001-05-0

108. Q10909912

109. N-[(2s,3r)-3-amino-2-hydroxy-4-phenylbutanoyl]-l-leucine

110. N-((2s,3r)-3-amino-2-hydroxy-4-phenylbutanoyl)-leucine

111. N-[(2s,3r)-3-amino-2-hydroxy-4-phenylbutyryl]-l-leucine, 97%

112. (2s)-2-[[(2s,3r)-3-amino-2-hydroxy-4-phenyl-butanoyl]amino]-4-methyl-pentanoic Acid

113. (s)-2-((2s,3r)-3-amino-2-hydroxy-4-phenylbutanamido)-4-methylpentanoicacid

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₆H₂₄N₂O₄
Molecular Weight	308.37 g/mol
XLogP3	-1
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	8
Exact Mass	308.17360725 g/mol
Monoisotopic Mass	308.17360725 g/mol
Topological Polar Surface Area	113 Å²
Heavy Atom Count	22
Formal Charge	0
Complexity	367
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
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

An adjuvant therapy used for acute and chronic myelonous leukemia, lung cancer and nasopharyngeal cancer. It is also used to treat hypercholesterolaemia.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Adjuvants, Immunologic

Substances that augment, stimulate, activate, potentiate, or modulate the immune response at either the cellular or humoral level. The classical agents (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contain bacterial antigens. Some are endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Their mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy of many biological response modifiers is related to their antigen-specific immunoadjuvanticity. (See all compounds classified as Adjuvants, Immunologic.)

Anti-HIV Agents

Agents used to treat AIDS and/or stop the spread of the HIV infection. These do not include drugs used to treat symptoms or opportunistic infections associated with AIDS. (See all compounds classified as Anti-HIV Agents.)

Antibiotics, Antineoplastic

Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms. (See all compounds classified as Antibiotics, Antineoplastic.)

Protease Inhibitors

Compounds which inhibit or antagonize biosynthesis or actions of proteases (ENDOPEPTIDASES). (See all compounds classified as Protease Inhibitors.)

Anti-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

Immunologic Factors

Biologically active substances whose activities affect or play a role in the functioning of the immune system. (See all compounds classified as Immunologic Factors.)

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