2-(3-amino-2-hydroxy-4-phenylbutanamido)-4-methylpentanoic acid

• ChemBase ID: 103790
• Molecular Formular: C16H24N2O4
• Molecular Mass: 308.37276
• Monoisotopic Mass: 308.17360726
• SMILES: CC(C)CC(NC(=O)C(O)C(N)Cc1ccccc1)C(=O)O
• Canonical SMILES: OC(C(=O)NC(C(=O)O)CC(C)C)C(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)
• InChIKey: VGGGPCQERPFHOB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(3-amino-2-hydroxy-4-phenylbutanamido)-4-methylpentanoic acid
• IUPAC Traditional name: @bestatin
• Synonyms: (2S,3R)-3-Amino-2-hydroxy-4-phenylbutanoyl]-Leu; BESTATIN

Database IDs

• CAS Number: 58970-76-6
• EC Number: 261-529-2
• PubChem SID: 162090439
• PubChem CID: 3238

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

Safety Information

• Storage Condition: -20°C, Desiccate
• RTECS: OH2915000

DETAILS

MP Biomedicals - 02152844

Free Acid
Inhibitor for aminopeptidase B and leucine aminopeptidase.

REFERENCES

• Umezawa, H., et al., J. Antibiot., 29: 97, (1976).