Ubenimex

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Ubenimex[1]
Ubenimex2DCSD.svg
Ubenimex3DanJ.gif
Names
IUPAC name
(2S)-2-[[(2S,3R)-3-Amino-2-hydroxy-4-phenylbutanoyl]amino]-4-methylpentanoic acid
Other names
Bestatin; N-[(2S,3R)-3-Amino-2-hydroxy-4-phenylbutyryl]-L-leucine
Identifiers
58970-76-6
65391-42-6 (HCl)
ChEMBL ChEMBL29292 YesY
ChemSpider 65145
Jmol 3D model Interactive image
PubChem 72172
UNII I0J33N5627 YesY
  • 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
    Key: VGGGPCQERPFHOB-RDBSUJKOSA-N
  • InChI=1/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
    Key: VGGGPCQERPFHOB-RDBSUJKOBZ
  • CC(C)C[C@@H](C(=O)O)NC(=O)[C@H]([C@@H](CC1=CC=CC=C1)N)O
Properties
C16H24N2O4
Molar mass 308.38 g·mol−1
Melting point 245 °C (473 °F; 518 K) (decomposes)
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
Infobox references

Ubenimex (INN), also known more commonly as bestatin, is a competitive, reversible protease inhibitor. It is an inhibitor of arginyl aminopeptidase (aminopeptidase B),[2] leukotriene A4 hydrolase (a zinc metalloprotease that displays both epoxide hydrolase and aminopeptidase activities),[3] alanyl aminopeptidase (aminopeptidase M/N),[4] leucyl/cystinyl aminopeptidase (oxytocinase/vasopressinase),[5][6] and membrane dipeptidase (leukotriene D4 hydrolase). It is being studied for use in the treatment of acute myelocytic leukemia.[7] It is derived from Streptomyces olivoreticuli.[8] Ubenimex has been found to inhibit the enzymatic degradation of oxytocin, vasopressin, enkephalins, and various other peptides and compounds.[citation needed]

Crystal structure of ubenimex
Crystal structure of ubenimex in the binding pocket of leukotriene A4 hydrolase. Rendered from PDB 1HS6.

See also

References

  1. N-((2S,3R)-3-Amino-2-hydroxy-4-phenylbutyryl)-L-leucine at Sigma-Aldrich
  2. Lua error in package.lua at line 80: module 'strict' not found.
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  4. Lua error in package.lua at line 80: module 'strict' not found.
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External links

  • The MEROPS online database for peptidases and their inhibitors: Bestatin



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