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    ubenimex

    ACTIVE PHARMA INGREDIENTS

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    DIGITAL CONTENT

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    2D Structure
    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

    2D Structure

    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 Weight 308.37 g/mol
    Molecular Formula C16H24N2O4
    XLogP3-1
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count8
    Exact Mass308.17360725 g/mol
    Monoisotopic Mass308.17360725 g/mol
    Topological Polar Surface Area113 Ų
    Heavy Atom Count22
    Formal Charge0
    Complexity367
    Isotope Atom Count0
    Defined Atom Stereocenter Count3
    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

    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.)