2-[3-(2-phenylacetamido)benzamido]benzoic acid

• ChemBase ID: 162452
• Molecular Formular: C22H18N2O4
• Molecular Mass: 374.38932
• Monoisotopic Mass: 374.12665707
• SMILES: c1cccc(c1)CC(=O)Nc1cccc(c1)C(=O)Nc1c(cccc1)C(=O)O
• Canonical SMILES: O=C(Nc1cccc(c1)C(=O)Nc1ccccc1C(=O)O)Cc1ccccc1
• InChI: InChI=1S/C22H18N2O4/c25-20(13-15-7-2-1-3-8-15)23-17-10-6-9-16(14-17)21(26)24-19-12-5-4-11-18(19)22(27)28/h1-12,14H,13H2,(H,23,25)(H,24,26)(H,27,28)
• InChIKey: OBGIRQUECFHUEY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[3-(2-phenylacetamido)benzamido]benzoic acid
• IUPAC Traditional name: 2-[3-(2-phenylacetamido)benzamido]benzoic acid
• Synonyms: 2-[[3-[(2-phenylacetyl)amino]benzoyl]amino]benzoic Acid; 2-[[3-[(phenylacetyl)amino]benzoyl]amino]benzoic Acid; BML-286

Database IDs

• CAS Number: 294891-81-9
• PubChem SID: 162256587
• PubChem CID: 5221450

CALCULATED PROPERTIES

• Acid pKa: 3.551387
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 2.5025432
• LogD (pH = 7.4): 1.085362
• Log P: 4.4447637
• Molar Refractivity: 108.4326 cm^3
• Polarizability: 39.734135 Å^3
• Polar Surface Area: 95.5 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B595870

A small molecule inhibitor of the PDZ domain of Dishevelled (Dvl): an essential protein in the Wnt signaling pathways. This compound reduced the levels of apoptosis in the hyaloid vessels of the eye and also suppressed the growth of prostate cancer PC-3 c

REFERENCES

• Grandy, D. et al.: J. Biol. Chem., 284, 24 (2009)