[(1R)-5-amino-1-{[(2S)-1-[(2R)-2-acetamido-3-phenylpropanoyl]pyrrolidin-2-yl]formamido}pentyl]boronic acid

• ChemBase ID: 5299
• Molecular Formular: C21H33BN4O5
• Molecular Mass: 432.32152
• Monoisotopic Mass: 432.25440058
• SMILES: B([C@H](CCCCN)NC(=O)[C@@H]1CCCN1C(=O)[C@@H](Cc1ccccc1)NC(=O)C)(O)O
• Canonical SMILES: NCCCC[C@@H](B(O)O)NC(=O)[C@@H]1CCCN1C(=O)[C@@H](Cc1ccccc1)NC(=O)C
• InChI: InChI=1S/C21H33BN4O5/c1-15(27)24-17(14-16-8-3-2-4-9-16)21(29)26-13-7-10-18(26)20(28)25-19(22(30)31)11-5-6-12-23/h2-4,8-9,17-19,30-31H,5-7,10-14,23H2,1H3,(H,24,27)(H,25,28)/t17-,18+,19+/m1/s1
• InChIKey: UCQIHCRMWNRFNP-QYZOEREBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(1R)-5-amino-1-{[(2S)-1-[(2R)-2-acetamido-3-phenylpropanoyl]pyrrolidin-2-yl]formamido}pentyl]boronic acid
• IUPAC Traditional name: (1R)-5-amino-1-{[(2S)-1-[(2R)-2-acetamido-3-phenylpropanoyl]pyrrolidin-2-yl]formamido}pentylboronic acid
• Synonyms: AC-(D)PHE-PRO-BOROLYS-OH

Database IDs

• PubChem SID: 160968728; 99444129
• PubChem CID: 5288064

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.506765
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -3.1356564
• LogD (pH = 7.4): -2.4300835
• Log P: 0.2864
• Molar Refractivity: 112.0142 cm^3
• Polarizability: 45.626976 Å^3
• Polar Surface Area: 144.99 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.63
• LOG S: -2.98
• Solubility (Water): 4.53e-01 g/l

DETAILS

DrugBank - DB07658

Drug information: experimental