[(1R)-4-amino-1-{[(2S)-1-[(2R)-2-acetamido-3-phenylpropanoyl]pyrrolidin-2-yl]formamido}butyl]boronic acid

• ChemBase ID: 5301
• Molecular Formular: C20H31BN4O5
• Molecular Mass: 418.29494
• Monoisotopic Mass: 418.23875051
• SMILES: B([C@H](CCCN)NC(=O)[C@@H]1CCCN1C(=O)[C@@H](Cc1ccccc1)NC(=O)C)(O)O
• Canonical SMILES: NCCC[C@@H](B(O)O)NC(=O)[C@@H]1CCCN1C(=O)[C@@H](Cc1ccccc1)NC(=O)C
• InChI: InChI=1S/C20H31BN4O5/c1-14(26)23-16(13-15-7-3-2-4-8-15)20(28)25-12-6-9-17(25)19(27)24-18(21(29)30)10-5-11-22/h2-4,7-8,16-18,29-30H,5-6,9-13,22H2,1H3,(H,23,26)(H,24,27)/t16-,17+,18+/m1/s1
• InChIKey: YKWKWNKWBGQECF-SQNIBIBYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(1R)-4-amino-1-{[(2S)-1-[(2R)-2-acetamido-3-phenylpropanoyl]pyrrolidin-2-yl]formamido}butyl]boronic acid
• IUPAC Traditional name: (1R)-4-amino-1-{[(2S)-1-[(2R)-2-acetamido-3-phenylpropanoyl]pyrrolidin-2-yl]formamido}butylboronic acid
• Synonyms: AC-(D)PHE-PRO-BOROHOMOORNITHINE-OH

Database IDs

• PubChem SID: 160968730; 99444131
• PubChem CID: 5288067

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.503018
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -3.509926
• LogD (pH = 7.4): -2.5686038
• Log P: -0.1099
• Molar Refractivity: 107.4132 cm^3
• Polarizability: 43.791294 Å^3
• Polar Surface Area: 144.99 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.23
• LOG S: -2.85
• Solubility (Water): 5.92e-01 g/l

DETAILS

DrugBank - DB07660

Drug information: experimental