<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2026-03-31 21:02:23 UTC</creation_date>
  <update_date>2026-05-14 17:49:57 UTC</update_date>
  <accession/>
  <common_name>Ubenimex</common_name>
  <class>SmallMolecule</class>
  <description>Ubenimex is an organic compound with the formula C16H24N2O4 and an average molecular weight of 308.38 g/mol. Ubenimex belongs to the hybrid peptides, a subclass of peptidomimetics within the organic compounds. This substance is found in or released from healthcare, pharmaceuticals &amp; veterinary products, specifically antibiotics, with recorded exposure routes including oral and inhalation.

In terms of biological activity, Ubenimex acts on two recorded protein targets. It functions as an inhibitor of Bacterial leucyl aminopeptidase and targets Leukotriene A-4 hydrolase (LTA4H).</description>
  <categories/>
  <types/>
  <synonyms>
    <synonym>(-)-N-((2S,3R)-3-Amino-2-hydroxy-4-phenylbutyryl)-L-leucine</synonym>
    <synonym>(2S)-2-((2S,3R)-3-amino-2-hydroxy-4-phenylbutanoylamino)-4-methylpentanoic acid</synonym>
    <synonym>(2S)-2-[[(2S,3R)-3-azaniumyl-2-hydroxy-4-phenylbutanoyl]amino]-4-methylpentanoate</synonym>
    <synonym>(2S,3R)-3-Amino-2-hydroxy-4-phenylbutanoyl-L-leucine</synonym>
    <synonym>(3-amino-2-hydroxy-4-phenylbutanoyl)-L-leucine</synonym>
    <synonym>(S)-2-((2S,3R)-3-amino-2-hydroxy-4-phenylbutanamido)-4-methylpentanoic acid</synonym>
    <synonym>(S-(R*,S*))-N-(3-Amino-2-hydroxy-4-phenylbutyroyl)-L-leucine</synonym>
    <synonym>([2S,3R]-3-Amino-2-hydroxy-4-phenylbutanoyl)-L-leucine</synonym>
    <synonym>2-(3-Amino-2-hydroxy-4-phenyl-butyrylamino)-4-methyl-pentanoic acid</synonym>
    <synonym>261-529-2</synonym>
    <synonym>3-(R)-Amino-2-(S)-hydroxy-4-phenylbutanoyl-(S)-leucine</synonym>
    <synonym>BEK</synonym>
    <synonym>BES</synonym>
    <synonym>Bestatin</synonym>
    <synonym>Bestatin free base</synonym>
    <synonym>Bestatin_x000D_</synonym>
    <synonym>I0J33N5627</synonym>
    <synonym>L-Leucine, N-(3-amino-2-hydroxy-1-oxo-4-phenylbutyl)-, (S-(R*,S*))-</synonym>
    <synonym>L-Leucine, N-[(2S,3R)-3-amino-2-hydroxy-1-oxo-4-phenylbutyl]-</synonym>
    <synonym>N-[(2S,3R)-3-Amino-2-hydroxy-1-oxo-4-phenylbutyl]-L-leucine</synonym>
    <synonym>N-[(2S,3R)-3-Amino-2-hydroxy-4-phenylbutanoyl]-L-leucine</synonym>
    <synonym>N-[(2S,3R)-3-Amino-2-hydroxy-4-phenylbutyryl]-L-leucine</synonym>
    <synonym>OH2915000</synonym>
    <synonym>QA-1889</synonym>
    <synonym>Ubenimex</synonym>
    <synonym>Ubenimex (Bestatin)</synonym>
    <synonym>Ubenimex [INN:JAN]</synonym>
    <synonym>Ubenimex |</synonym>
    <synonym>Ubenimex(Bestatin)</synonym>
    <synonym>Ubenimex, Bestatin</synonym>
    <synonym>Ubestatin</synonym>
    <synonym>UNII:I0J33N5627</synonym>
    <synonym>[(2S,3R)-3-Amino-2-hydroxy-4-phenylbutanoyl]-L-leucine</synonym>
    <synonym>[(2S,3R)-3-Amino-2-hydroxy-4-phenylbutyryl]-L-leucine</synonym>
    <synonym>[58970-76-6]</synonym>
  </synonyms>
  <chemical_formula>C16H24N2O4</chemical_formula>
  <average_molecular_weight>308.378</average_molecular_weight>
  <monisotopic_moleculate_weight>308.173607</monisotopic_moleculate_weight>
  <iupac_name>(2S)-2-{[(2S,3R)-3-amino-1,2-dihydroxy-4-phenylbutylidene]amino}-4-methylpentanoic acid</iupac_name>
  <traditional_iupac>(2S)-2-{[(2S,3R)-3-amino-1,2-dihydroxy-4-phenylbutylidene]amino}-4-methylpentanoic acid</traditional_iupac>
  <cas_registry_number>58970-76-6</cas_registry_number>
  <smiles>CC(C)C[C@@H](NC(=O)[C@@H](O)[C@H](N)CC1=CC=CC=C1)C(O)=O</smiles>
  <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</inchi>
  <inchikey>VGGGPCQERPFHOB-RDBSUJKOSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Peptidomimetics</class>
    <sub_class>Hybrid peptides</sub_class>
    <direct_parent>Hybrid peptides</direct_parent>
    <alternate_parents>
      <alternative_parent>Amino acids</alternative_parent>
      <alternative_parent>Amphetamines and derivatives</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Beta amino acids and derivatives</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Leucine and derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>N-acyl amines</alternative_parent>
      <alternative_parent>N-acyl-L-alpha-amino acids</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Alpha-amino acid or derivatives</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino acid</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Amphetamine or derivatives</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Beta amino acid or derivatives</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty amide</substituent>
      <substituent>Hybrid peptide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Leucine or derivatives</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>N-acyl-alpha amino acid or derivatives</substituent>
      <substituent>N-acyl-alpha-amino acid</substituent>
      <substituent>N-acyl-amine</substituent>
      <substituent>N-acyl-l-alpha-amino acid</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <descriptors/>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways/>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>-1.1</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.66</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.56</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>8.41e-01 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>3.77</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S)-2-{[(2S,3R)-3-amino-1,2-dihydroxy-4-phenylbutylidene]amino}-4-methylpentanoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>308.378</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>308.173607</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)C[C@@H](NC(=O)[C@@H](O)[C@H](N)CC1=CC=CC=C1)C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C16H24N2O4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>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</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VGGGPCQERPFHOB-RDBSUJKOSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>116.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>82.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>32.97</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <route_of_exposure/>
  <mechanism_of_toxicity/>
  <metabolism/>
  <toxicity/>
  <lethaldose/>
  <carcinogenicity/>
  <use_source/>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f7221bcdca8&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB03424</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>72172</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>65145</chemspider_id>
  <kegg_id/>
  <uniprot_id/>
  <omim_id/>
  <chebi_id/>
  <biocyc_id/>
  <ctd_id/>
  <stitch_id/>
  <actor_id/>
  <pdb_id/>
  <wikipidia/>
  <general_references/>
  <targets>
    <target>
      <target_id/>
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      <target_id>BE0001395</target_id>
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  </targets>
</compound>
