(2R)-2-amino-3-({[(1S)-1-acetamido-2-(naphthalen-1-yl)ethyl](hydroxy)boranyl}oxy)propanoic acid

• ChemBase ID: 2402
• Molecular Formular: C17H21BN2O5
• Molecular Mass: 344.17004
• Monoisotopic Mass: 344.15435218
• SMILES: CC(=O)N[C@H](Cc1cccc2c1cccc2)B(O)OC[C@@H](N)C(=O)O
• Canonical SMILES: CC(=O)N[C@@H](B(OC[C@H](C(=O)O)N)O)Cc1cccc2c1cccc2
• InChI: InChI=1S/C17H21BN2O5/c1-11(21)20-16(18(24)25-10-15(19)17(22)23)9-13-7-4-6-12-5-2-3-8-14(12)13/h2-8,15-16,24H,9-10,19H2,1H3,(H,20,21)(H,22,23)/t15-,16-/m1/s1
• InChIKey: RLFLMJSNFHALGJ-HZPDHXFCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-amino-3-({[(1S)-1-acetamido-2-(naphthalen-1-yl)ethyl](hydroxy)boranyl}oxy)propanoic acid
• IUPAC Traditional name: (2R)-2-amino-3-({[(1S)-1-acetamido-2-(naphthalen-1-yl)ethyl](hydroxy)boranyl}oxy)propanoic acid
• Synonyms: D-Naphthyl-1-Acetamido Boronic Acid Alanine

Database IDs

• PubChem SID: 160965853; 46508778
• PubChem CID: 17754157; 70789221

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.9290947
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -0.77622044
• LogD (pH = 7.4): -0.8000956
• Log P: -0.776196
• Molar Refractivity: 87.1303 cm^3
• Polarizability: 37.25862 Å^3
• Polar Surface Area: 121.88 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.45
• LOG S: -4.01
• Solubility (Water): 3.74e-02 g/l

DETAILS

DrugBank - DB02677

Drug information: experimental