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

• ChemBase ID: 179593
• 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-])N[C@@H](CO)C
• Canonical SMILES: OC[C@H](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)/t12-/m1/s1
• InChIKey: ZISFCTXLAXIEMV-GFCCVEGCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(3,4-dimethoxyphenyl)methyl]-2-{[(2R)-1-hydroxypropan-2-yl]amino}-5-nitrobenzamide
• IUPAC Traditional name: N-[(3,4-dimethoxyphenyl)methyl]-2-{[(2R)-1-hydroxypropan-2-yl]amino}-5-nitrobenzamide
• Synonyms: N-[(3,4-Dimethoxyphenyl)methyl]-2-[[(1R)-2-hydroxy-1-methylethyl]amino]-5-nitro-benzamide; FR 226807; (R)-Xanthoanthrafil

Database IDs

• CAS Number: 247568-68-9
• PubChem SID: 164235503
• PubChem CID: 9821702

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: 126-128°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - X500005

Phosphodiesterase-5 (PDE-5) inhibitor, found in supplements aimed to enhance male sexual function. Also, is used to treat pulmonary diseases and B-cell proliferative disorders.

REFERENCES

• Wang, S., et al.: J. Biol. Chem., 277, 9880 (2002)
• Hosogai, N., et al.: Eur. J. Pharmacol., 477, 171 (2002)
• Kumasaka, K., et al.: Chem. Pharm. Bull., 56, 227 (2002)