N-[(3,4-dimethoxyphenyl)methyl]-2-[(1-hydroxypropan-2-yl)amino]-5-nitrobenzamide

• ChemBase ID: 179591
• Molecular Formular: C19H23N3O6
• Molecular Mass: 389.40242
• Monoisotopic Mass: 389.15868547
• SMILES: c1(cc(c(cc1)OC)OC)CNC(=O)c1c(ccc(c1)[N+](=O)[O-])NC(CO)C
• Canonical SMILES: OCC(Nc1ccc(cc1C(=O)NCc1ccc(c(c1)OC)OC)[N+](=O)[O-])C
• InChI: InChI=1S/C19H23N3O6/c1-12(11-23)21-16-6-5-14(22(25)26)9-15(16)19(24)20-10-13-4-7-17(27-2)18(8-13)28-3/h4-9,12,21,23H,10-11H2,1-3H3,(H,20,24)
• InChIKey: ZISFCTXLAXIEMV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(3,4-dimethoxyphenyl)methyl]-2-[(1-hydroxypropan-2-yl)amino]-5-nitrobenzamide
• IUPAC Traditional name: N-[(3,4-dimethoxyphenyl)methyl]-2-[(1-hydroxypropan-2-yl)amino]-5-nitrobenzamide
• Synonyms: N-[(3,4-Dimethoxyphenyl)methyl]-2-[(2-hydroxy-1-methylethyl)amino]-5-nitro-benzamide; Benzamidenafil; rac Xanthoanthrafil

Database IDs

• CAS Number: 1020251-53-9
• PubChem SID: 164235501
• PubChem CID: 10110873

CALCULATED PROPERTIES

• Acid pKa: 14.109567
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): 2.245928
• LogD (pH = 7.4): 2.245928
• Log P: 2.245928
• Molar Refractivity: 105.8017 cm^3
• Polarizability: 38.852085 Å^3
• Polar Surface Area: 125.64 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO
• Apperance: Light Yellow Solid
• Melting Point: 154-156°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - X500000

Phosphodiesterase-5 (PDE-5) inhibitor, found in supplements aimed to enhance male sexual function

REFERENCES

• Zou, P., et al.: J. Pharm. Biomed. Anal., 47, 255 (2008)