N-hydroxy-4-({5-[4-(N-hydroxycarbamimidoyl)phenoxy]pentyl}oxy)benzene-1-carboximidamide

• ChemBase ID: 176316
• Molecular Formular: C19H24N4O4
• Molecular Mass: 372.41826
• Monoisotopic Mass: 372.17975527
• SMILES: c1(OCCCCCOc2ccc(cc2)C(=N)NO)ccc(cc1)C(=N)NO
• Canonical SMILES: ONC(=N)c1ccc(cc1)OCCCCCOc1ccc(cc1)C(=N)NO
• InChI: InChI=1S/C19H24N4O4/c20-18(22-24)14-4-8-16(9-5-14)26-12-2-1-3-13-27-17-10-6-15(7-11-17)19(21)23-25/h4-11,24-25H,1-3,12-13H2,(H2,20,22)(H2,21,23)
• InChIKey: UVADNHMLTJNGDH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-hydroxy-4-({5-[4-(N-hydroxycarbamimidoyl)phenoxy]pentyl}oxy)benzene-1-carboximidamide
• IUPAC Traditional name: N-hydroxy-4-({5-[4-(N-hydroxycarbamimidoyl)phenoxy]pentyl}oxy)benzenecarboximidamide
• Synonyms: 4,4'-[1,5-pentanediylbis(oxy)]bis[N-hydroxybenzenecarboximidamide]; 1,5-Bis(4’-hydroxyamidinophenoxy)pentane; N,N’-Dihydroxy Pentamidine; Pentamidine Diamidoxime

Database IDs

• CAS Number: 101689-95-6
• PubChem SID: 164232226
• PubChem CID: 5487105

CALCULATED PROPERTIES

• Acid pKa: 14.600793
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -1.6155672
• LogD (pH = 7.4): 1.4222729
• Log P: 2.4457555
• Molar Refractivity: 145.0442 cm^3
• Polarizability: 39.11951 Å^3
• Polar Surface Area: 130.68 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - P272515

Pentamidine Dioxime is a diamidoxime metabolite of Pentamidine (P272500).

REFERENCES

• Clement, B. et al.: Arzneim.-Forsch., 35, 1009 (1985)
• Atsriku, C. et al.: Chem.-Biol. Inter., 146, 297 (1985)
• Clement, B. et al.: ARrh. Pharm., 325, 61 (1985)