4-{[5-(4-carbamimidoylphenoxy)-3-hydroxypentyl]oxy}benzene-1-carboximidamide

• ChemBase ID: 162154
• Molecular Formular: C19H24N4O3
• Molecular Mass: 356.41886
• Monoisotopic Mass: 356.18484065
• SMILES: c1(OCCC(CCOc2ccc(cc2)C(=N)N)O)ccc(cc1)C(=N)N
• Canonical SMILES: OC(CCOc1ccc(cc1)C(=N)N)CCOc1ccc(cc1)C(=N)N
• InChI: InChI=1S/C19H24N4O3/c20-18(21)13-1-5-16(6-2-13)25-11-9-15(24)10-12-26-17-7-3-14(4-8-17)19(22)23/h1-8,15,24H,9-12H2,(H3,20,21)(H3,22,23)
• InChIKey: LZRGIVAJLHKJOI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{[5-(4-carbamimidoylphenoxy)-3-hydroxypentyl]oxy}benzene-1-carboximidamide
• IUPAC Traditional name: 4-{[5-(4-carbamimidoylphenoxy)-3-hydroxypentyl]oxy}benzenecarboximidamide
• Synonyms: 4,4'-[(2-Hydroxy-1,5-pentanediyl)bis(oxy)]bisbenzenecarboximidamide; 1,5-Di(4-amidinophenoxy)-2-pentanol; 1,5-Bis(4-amidinophenoxy)-2-pentanol; 4,4'-[(3-Hydroxy-1,5-pentanediyl)bis(oxy)]bisbenzenecarboximidamide; 1,5-Di(4-amidinophenoxy)-3-pentanol; 1,5-Bis(4-amidinophenoxy)-3-pentanol

Database IDs

• CAS Number: 133991-33-0; 133991-32-9
• PubChem SID: 162256289
• PubChem CID: 456173

CALCULATED PROPERTIES

• Acid pKa: 15.110531
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -4.0406656
• LogD (pH = 7.4): -4.0323725
• Log P: 0.79014564
• Molar Refractivity: 122.1117 cm^3
• Polarizability: 38.48787 Å^3
• Polar Surface Area: 138.43 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B401405

1,5-Bis(4-amidinophenoxy)-3-pentanol is a hydroxylated metabolite of Pentamidine (P272500).

Toronto Research Chemicals - B401400

1,5-Bis(4-amidinophenoxy)-2-pentanol is a hydroxylated metabolite of Pentamidine (P272500).

REFERENCES

• Tuttle, R.H. et al.: J. Chrom. B. Biomed. Appl., 688, 319 (1997)
• Atsriku, C. et al.: Chem.-Biol. Inter., 146, 297 (1997)
• Bronner, U. et al.: Pharmacol. Toxicol., 77, 114 (1997)
• Atsriku, C. et al.: Chem.-Biol. Inter., 146, 297 (2003)
• Bronner, U. et al.: Pharmacol. Toxicol., 77, 114 (2003)