[(1R)-6-amino-1-{[(2S)-1-[(2R)-2-acetamido-3-phenylpropanoyl]pyrrolidin-2-yl]formamido}hexyl]boronic acid

• ChemBase ID: 5300
• Molecular Formular: C22H35BN4O5
• Molecular Mass: 446.3481
• Monoisotopic Mass: 446.27005064
• SMILES: B([C@H](CCCCCN)NC(=O)[C@@H]1CCCN1C(=O)[C@@H](Cc1ccccc1)NC(=O)C)(O)O
• Canonical SMILES: NCCCCC[C@@H](B(O)O)NC(=O)[C@@H]1CCCN1C(=O)[C@@H](Cc1ccccc1)NC(=O)C
• InChI: InChI=1S/C22H35BN4O5/c1-16(28)25-18(15-17-9-4-2-5-10-17)22(30)27-14-8-11-19(27)21(29)26-20(23(31)32)12-6-3-7-13-24/h2,4-5,9-10,18-20,31-32H,3,6-8,11-15,24H2,1H3,(H,25,28)(H,26,29)/t18-,19+,20+/m1/s1
• InChIKey: AILSWIBFGYYZTK-AABGKKOBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(1R)-6-amino-1-{[(2S)-1-[(2R)-2-acetamido-3-phenylpropanoyl]pyrrolidin-2-yl]formamido}hexyl]boronic acid
• IUPAC Traditional name: (1R)-6-amino-1-{[(2S)-1-[(2R)-2-acetamido-3-phenylpropanoyl]pyrrolidin-2-yl]formamido}hexylboronic acid
• Synonyms: AC-(D)PHE-PRO-BOROHOMOLYS-OH

Database IDs

• PubChem SID: 160968729; 99444130
• PubChem CID: 5288066

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.509011
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -2.7393572
• LogD (pH = 7.4): -2.0337963
• Log P: 0.6827
• Molar Refractivity: 116.6152 cm^3
• Polarizability: 47.463417 Å^3
• Polar Surface Area: 144.99 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.93
• LOG S: -3.33
• Solubility (Water): 2.11e-01 g/l

DETAILS

DrugBank - DB07659

Drug information: experimental