1,3,5,7-tetraazatricyclo[3.3.1.13,7]decane; 2-(phenylformamido)acetic acid

• ChemBase ID: 172590
• Molecular Formular: C15H21N5O3
• Molecular Mass: 319.35894
• Monoisotopic Mass: 319.16443956
• SMILES: C1N2CN3CN1CN(C2)C3.C(=O)(NCC(=O)O)c1ccccc1
• Canonical SMILES: C1N2CN3CN1CN(C2)C3.O=C(c1ccccc1)NCC(=O)O
• InChI: InChI=1S/C9H9NO3.C6H12N4/c11-8(12)6-10-9(13)7-4-2-1-3-5-7;1-7-2-9-4-8(1)5-10(3-7)6-9/h1-5H,6H2,(H,10,13)(H,11,12);1-6H2
• InChIKey: ROAIXOJGRFKICW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3,5,7-tetraazatricyclo[3.3.1.1^3,^7]decane; 2-(phenylformamido)acetic acid
• IUPAC Traditional name: hippuric acid; methenamine
• Synonyms: 1,3,5,7-Tetraazatricyclo[3.3.1.13,7]decane N-Benzoylglycine; Hexamethylenetetramine Monohippurate; Haiprex; Hexamethylenetetramine Hippurate; Hexamethylenetetramine Hippuric Acid Complex; Hippramine; Hiprex; R-657; Urex; Viapta; Methenamine Hippurate

Database IDs

• CAS Number: 5714-73-8
• PubChem SID: 164228500
• PubChem CID: 21945

CALCULATED PROPERTIES

• Acid pKa: 3.591235
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -1.3782723
• LogD (pH = 7.4): -2.8205347
• Log P: 0.5255455
• Molar Refractivity: 46.1177 cm^3
• Polarizability: 17.405828 Å^3
• Polar Surface Area: 66.4 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 89-95°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - M226025

Antibacterial (urinary).

REFERENCES

• Lim, J., et al.: J. Pharm. Sci., 62, 1503 (1973)
• Gleckman, R., et al.: Am. J. Hosp. Pharm., 36, 1509 (1973)
• Onur, F., et al.: Int. J. Pharm., 78, 89 (1973)