3-[(2R)-2-(dihydroxyboranyl)-2-(2-phenylacetamido)ethyl]benzoic acid

• ChemBase ID: 5113
• Molecular Formular: C17H18BNO5
• Molecular Mass: 327.13952
• Monoisotopic Mass: 327.12780308
• SMILES: C([C@@H](B(O)O)NC(=O)Cc1ccccc1)c1cccc(C(=O)O)c1
• Canonical SMILES: O=C(Cc1ccccc1)N[C@H](B(O)O)Cc1cccc(c1)C(=O)O
• InChI: InChI=1S/C17H18BNO5/c20-16(11-12-5-2-1-3-6-12)19-15(18(23)24)10-13-7-4-8-14(9-13)17(21)22/h1-9,15,23-24H,10-11H2,(H,19,20)(H,21,22)/t15-/m0/s1
• InChIKey: ZAHVYMBTUDWUAX-HNNXBMFYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(2R)-2-(dihydroxyboranyl)-2-(2-phenylacetamido)ethyl]benzoic acid
• IUPAC Traditional name: 3-[(2R)-2-(dihydroxyboranyl)-2-(2-phenylacetamido)ethyl]benzoic acid
• Synonyms: (1R)-2-PHENYLACETAMIDO-2-(3-CARBOXYPHENYL)ETHYL BORONIC ACID

Database IDs

• PubChem SID: 160968543; 99443937
• PubChem CID: 5287796

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.044284
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 1.2614133
• LogD (pH = 7.4): -0.4582525
• Log P: 2.7295
• Molar Refractivity: 84.3962 cm^3
• Polarizability: 34.0549 Å^3
• Polar Surface Area: 106.86 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.37
• LOG S: -4.19
• Solubility (Water): 2.11e-02 g/l

DETAILS

DrugBank - DB07466

Drug information: experimental