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

• ChemBase ID: 72759
• Molecular Formular: C16H24N2O4
• Molecular Mass: 308.37276
• Monoisotopic Mass: 308.17360726
• SMILES: c1cccc(c1)C[C@H]([C@@H](C(=O)N[C@H](C(=O)O)CC(C)C)O)N
• Canonical SMILES: O[C@H](C(=O)N[C@H](C(=O)O)CC(C)C)[C@@H](Cc1ccccc1)N
• 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
• InChIKey: VGGGPCQERPFHOB-RDBSUJKOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S,3R)-3-amino-2-hydroxy-4-phenylbutanamido]-4-methylpentanoic acid
• IUPAC Traditional name: ubenimex
• Synonyms: ([2S,3R]-3-Amino-2-hydroxy-4-phenylbutanoyl)-L-leucine; N-[(2S,3R)-3-Amino-2-hydroxy-4-phenylbutyryl]-L-leucine; N-[(2S,3R)-3-Amino-2-hydroxy-4-phenylbutyryl]-L-leucine; Bestatin; Ubenimex; ([2S,3R]-3-氨基-2-羟基-4-苯基丁酰基)-L-亮氨酸; N-[(2S,3R)-3-氨基-2-羟基-4-苯基丁酰基]-L-亮氨酸

Database IDs

• CAS Number: 58970-76-6
• EC Number: 261-529-2
• MDL Number: MFCD00083262
• PubChem SID: 162037680; 24871835
• PubChem CID: 72172
• CHEMBL: 29292
• Wikipedia Title: Ubenimex

CALCULATED PROPERTIES

• Acid pKa: 3.7260025
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -1.1024202
• LogD (pH = 7.4): -1.1396116
• Log P: -1.0995758
• Molar Refractivity: 82.0498 cm^3
• Polarizability: 32.62761 Å^3
• Polar Surface Area: 112.65 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 245 °C (dec.); 245 °C (dec.)(lit.)
• Optical Rotation: [α]20/D -11°, c = 1 in 1 M NaOH

Safety Information

• Storage Condition: -20°C
• RTECS: OH2915000
• German water hazard class: 3
• Safety Statements: S22 S24/25
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Target: Aminopeptidase N(APN)
• Gene Information: human ... ANPEP(290), DPP4(1803)mouse ... Rnpep(215615)rat ... Mme(24590)

Product Information

• Purity: 97%
• Salt Data: Free Base
• Linear Formula: (CH3)2CHCH2CH[NHCOCH(OH)CH(NH2)CH2C6H5]CO2H

DETAILS

Selleck Chemicals - S1591

Research Area: Cancer
Biological Activity:
Ubenimex is a competitive aminopeptidase B inhibitor with an IC50 of 100 mg/ml for K562 cells. Proliferation of all the cell lines except KG1 was inhibited by bestatin. P39/TSU, HL60 and U937 were highly sensitive, with 50% growth inhibitory concentrations (IC50) close to the maximum serum concentration when bestatin was orally administered at 30 mg in clinical application. All cell lines except for K562 highly expressed CD13, but a clear correlation between the sensitivity to bestatin and expression of CD13 was not observed. Other aminopeptidase inhibitors such as amastatin A, arphamenine B and WM15 antibody showed no growth inhibitory effects. [1]References on Ubenimex (Bestatin)[1] http://en.wikipedia.org/wiki/Ubenimex, ,

Sigma Aldrich - 482609

Packaging
500 mg in glass bottle