3-[(R)-(dihydroxyboranyl)[2-(thiophen-2-yl)acetamido]methyl]benzoic acid

• ChemBase ID: 6161
• Molecular Formular: C14H14BNO5S
• Molecular Mass: 319.14066
• Monoisotopic Mass: 319.06857395
• SMILES: c1ccsc1CC(=O)N[C@H](B(O)O)c1cc(ccc1)C(=O)O
• Canonical SMILES: O=C(N[C@@H](c1cccc(c1)C(=O)O)B(O)O)Cc1cccs1
• InChI: InChI=1S/C14H14BNO5S/c17-12(8-11-5-2-6-22-11)16-13(15(20)21)9-3-1-4-10(7-9)14(18)19/h1-7,13,20-21H,8H2,(H,16,17)(H,18,19)/t13-/m0/s1
• InChIKey: HQLQTGGLHBYZSA-ZDUSSCGKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(R)-(dihydroxyboranyl)[2-(thiophen-2-yl)acetamido]methyl]benzoic acid
• IUPAC Traditional name: 3-[(R)-(dihydroxyboranyl)[2-(thiophen-2-yl)acetamido]methyl]benzoic acid
• Synonyms: (1R)-1-(2-THIENYLACETYLAMINO)-1-(3-CARBOXYPHENYL)METHYLBORONIC ACID

Database IDs

• PubChem SID: 99445022; 160969586
• PubChem CID: 5289377

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.031753
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 0.8202762
• LogD (pH = 7.4): -0.89581764
• Log P: 2.3004
• Molar Refractivity: 76.5311 cm^3
• Polarizability: 30.932795 Å^3
• Polar Surface Area: 106.86 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.22
• LOG S: -4.03
• Solubility (Water): 2.97e-02 g/l

DETAILS

DrugBank - DB08551

Drug information: experimental