(4-{2-[(5-chloro-2-methoxyphenyl)formamido]ethyl}phenoxy)phosphonic acid

• ChemBase ID: 164373
• Molecular Formular: C16H17ClNO6P
• Molecular Mass: 385.736041
• Monoisotopic Mass: 385.04820158
• SMILES: c1(ccc(c(c1)C(=O)NCCc1ccc(cc1)OP(=O)(O)O)OC)Cl
• Canonical SMILES: COc1ccc(cc1C(=O)NCCc1ccc(cc1)OP(=O)(O)O)Cl
• InChI: InChI=1S/C16H17ClNO6P/c1-23-15-7-4-12(17)10-14(15)16(19)18-9-8-11-2-5-13(6-3-11)24-25(20,21)22/h2-7,10H,8-9H2,1H3,(H,18,19)(H2,20,21,22)
• InChIKey: RHSICLBXTJYWMY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4-{2-[(5-chloro-2-methoxyphenyl)formamido]ethyl}phenoxy)phosphonic acid
• IUPAC Traditional name: 4-{2-[(5-chloro-2-methoxyphenyl)formamido]ethyl}phenoxyphosphonic acid
• Synonyms: 5-Chloro-2-methoxy-N-[2-[4-(phosphonooxy)phenyl]ethyl]benzamide; p-[2-[(5-Chloro-2-methoxybenzoyl)amino]ethyl]benzenephosphonate

Database IDs

• CAS Number: 594854-55-4
• PubChem SID: 162258508
• PubChem CID: 29976032

CALCULATED PROPERTIES

• Acid pKa: 1.7892774
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 0.16888899
• LogD (pH = 7.4): -0.5598951
• Log P: 2.5496395
• Molar Refractivity: 93.5225 cm^3
• Polarizability: 35.827873 Å^3
• Polar Surface Area: 105.09 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C367920

A membrane-impermeant Glibenclamide analogue.

REFERENCES

• Meyer, M., et al.: Br. J. Pharmacol., 128, 27 (1999)