[(1R)-1-{[(2S)-1-[(2R)-2-amino-3-phenylpropanoyl]pyrrolidin-2-yl]formamido}-2-(3-cyanophenyl)ethyl]boronic acid

• ChemBase ID: 6033
• Molecular Formular: C23H27BN4O4
• Molecular Mass: 434.29588
• Monoisotopic Mass: 434.21253576
• SMILES: C(c1cc(ccc1)C#N)[C@H](NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](Cc1ccccc1)N)B(O)O
• Canonical SMILES: N#Cc1cccc(c1)C[C@@H](B(O)O)NC(=O)[C@@H]1CCCN1C(=O)[C@@H](Cc1ccccc1)N
• InChI: InChI=1S/C23H27BN4O4/c25-15-18-9-4-8-17(12-18)14-21(24(31)32)27-22(29)20-10-5-11-28(20)23(30)19(26)13-16-6-2-1-3-7-16/h1-4,6-9,12,19-21,31-32H,5,10-11,13-14,26H2,(H,27,29)/t19-,20+,21+/m1/s1
• InChIKey: UFOIPTZMXQILSG-HKBOAZHASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(1R)-1-{[(2S)-1-[(2R)-2-amino-3-phenylpropanoyl]pyrrolidin-2-yl]formamido}-2-(3-cyanophenyl)ethyl]boronic acid
• IUPAC Traditional name: (1R)-1-{[(2S)-1-[(2R)-2-amino-3-phenylpropanoyl]pyrrolidin-2-yl]formamido}-2-(3-cyanophenyl)ethylboronic acid
• Synonyms: 1-{[1-(2-AMINO-3-PHENYL-PROPIONYL)-PYRROLIDINE-2-CARBONYL]-AMINO}-2-(3-CYANO-PHENYL)-ETHANEBORONIC ACID

Database IDs

• PubChem SID: 160969458; 99444891
• PubChem CID: 5289192

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.550306
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 0.013831476
• LogD (pH = 7.4): 1.7168449
• Log P: 2.194
• Molar Refractivity: 115.5988 cm^3
• Polarizability: 46.609432 Å^3
• Polar Surface Area: 139.68 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.26
• LOG S: -4.05
• Solubility (Water): 3.91e-02 g/l

DETAILS

DrugBank - DB08420

Drug information: experimental