(1S,5S,7R)-3-N-hydroxy-7-N-[(4-phenylphenyl)methyl]-6,8-dioxa-3-azabicyclo[3.2.1]octane-3,7-dicarboxamide

• ChemBase ID: 4679
• Molecular Formular: C20H21N3O5
• Molecular Mass: 383.39784
• Monoisotopic Mass: 383.14812079
• SMILES: O=C([C@@H]1O[C@H]2CN(C[C@@H]1O2)C(=O)NO)NCc1ccc(cc1)c1ccccc1
• Canonical SMILES: ONC(=O)N1C[C@@H]2O[C@H](C1)O[C@H]2C(=O)NCc1ccc(cc1)c1ccccc1
• InChI: InChI=1S/C20H21N3O5/c24-19(18-16-11-23(20(25)22-26)12-17(27-16)28-18)21-10-13-6-8-15(9-7-13)14-4-2-1-3-5-14/h1-9,16-18,26H,10-12H2,(H,21,24)(H,22,25)/t16-,17-,18+/m0/s1
• InChIKey: PPLDARNGJSQINK-OKZBNKHCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5S,7R)-3-N-hydroxy-7-N-[(4-phenylphenyl)methyl]-6,8-dioxa-3-azabicyclo[3.2.1]octane-3,7-dicarboxamide
• IUPAC Traditional name: (1S,5S,7R)-3-N-hydroxy-7-N-[(4-phenylphenyl)methyl]-6,8-dioxa-3-azabicyclo[3.2.1]octane-3,7-dicarboxamide
• Synonyms: (1S,5S,7R)-N~7~-(BIPHENYL-4-YLMETHYL)-N~3~-HYDROXY-6,8-DIOXA-3-AZABICYCLO[3.2.1]OCTANE-3,7-DICARBOXAMIDE

Database IDs

• PubChem SID: 160968111; 99443497
• PubChem CID: 11987860

CALCULATED PROPERTIES

JChem

• Acid pKa: 10.042815
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.5073401
• LogD (pH = 7.4): 1.506378
• Log P: 1.5073524
• Molar Refractivity: 99.555 cm^3
• Polarizability: 40.11271 Å^3
• Polar Surface Area: 100.13 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.34
• LOG S: -2.92
• Solubility (Water): 4.58e-01 g/l

DETAILS

DrugBank - DB07026

Drug information: experimental