Bestatin

Ubenimex
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
CAS Number	58970-76-6 65391-42-6 (HCl)
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL29292^Y
ChemSpider	65145
ECHA InfoCard	100.055.917
PubChem	72172
UNII	I0J33N5627^Y
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 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
SMILES CC(C)C[C@@H](C(=O)O)NC(=O)[C@H]([C@@H](CC1=CC=CC=C1)N)O
Properties
Chemical formula	C₁₆H₂₄N₂O₄
Molar mass	308.38 g·mol⁻¹
Melting point	245 °C (473 °F; 518 K) (decomposes)
Hazards
S-phrases	S22 S24/25
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y (what is ^YN ?)
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),leukotriene A₄ hydrolase (a zinc metalloprotease that displays both epoxide hydrolase and aminopeptidase activities),alanyl aminopeptidase (aminopeptidase M/N),leucyl/cystinyl aminopeptidase (oxytocinase/vasopressinase), and membrane dipeptidase (leukotriene D₄ hydrolase). It is being studied for use in the treatment of acute myelocytic leukemia. It is derived from Streptomyces olivoreticuli. Ubenimex has been found to inhibit the enzymatic degradation of , vasopressin, enkephalins, and various other peptides and compounds.