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

• ChemBase ID: 132429
• Molecular Formular: C16H25ClN2O4
• Molecular Mass: 344.8337
• Monoisotopic Mass: 344.15028497
• SMILES: CC(C)C[C@@H](C(=O)O)NC(=O)[C@H]([C@@H](Cc1ccccc1)N)O.Cl
• Canonical SMILES: O[C@H](C(=O)N[C@H](C(=O)O)CC(C)C)[C@@H](Cc1ccccc1)N.Cl
• InChI: InChI=1S/C16H24N2O4.ClH/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);1H/t12-,13+,14+;/m1./s1
• InChIKey: XGDFITZJGKUSDK-UDYGKFQRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S,3R)-3-amino-2-hydroxy-4-phenylbutanamido]-4-methylpentanoic acid hydrochloride
• IUPAC Traditional name: ubenimex hydrochloride
• Synonyms: N-[(2S,3R)-3-Amino-2-hydroxy-4-phenylbutyryl]-L-leucine hydrochloride; Bestatin hydrochloride

Database IDs

• CAS Number: 65391-42-6
• MDL Number: MFCD00058004
• Beilstein Number: 4628066
• PubChem SID: 24278278; 162226706
• PubChem CID: 11957481

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

• Solubility: H2O: soluble25 mg/mL, clear, colorless
• Melting Point: 216-218 °C

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC); ≥99.0% (HPLC)
• Quality Level: PREMIUM
• Empirical Formula (Hill Notation): C16H24N2O4 · HCl

DETAILS

Sigma Aldrich - B8385

Preparation Note
Solubility testing in water at 25 mg/ml yields a clear solution. Stock solutions at 1 mM are expected to be stable at least one month stored at -20 °C.
Biochem/physiol Actions
A metalloprotease inhibitor selective for aminopeptidase. Bestatin is a competitive and specific inhibitor of leucine aminopeptidase, aminopeptidase B, and triamino peptidase. It inhibits aminopeptidase B at 60 nM (using arginine-β-naphthylamide as substrate) and leucine aminopeptidase at 20 nM (leucine-β-naphthylamide as substrate). It showed no inhibition of aminopeptidase A, trypsin, chymotrypsin, elastase, papain, pepsin, or themolysin. It offers promise as a novel analgesic because it protects endogenous opioid peptides against degradation.1

Sigma Aldrich - 08170

Other Notes
Specific inhibitor of aminopeptidase B and leucine aminopeptidase2; Immunomodifier3; other biological effects see4
Biochem/physiol Actions
A metalloprotease inhibitor selective for aminopeptidase. Bestatin is a competitive and specific inhibitor of leucine aminopeptidase, aminopeptidase B, and triamino peptidase. It inhibits aminopeptidase B at 60 nM (using arginine-β-naphthylamide as substrate) and leucine aminopeptidase at 20 nM (leucine-β-naphthylamide as substrate). It showed no inhibition of aminopeptidase A, trypsin, chymotrypsin, elastase, papain, pepsin, or themolysin. It offers promise as a novel analgesic because it protects endogenous opioid peptides against degradation.1