5-{2-hydroxy-5-[(4-methylpiperazin-1-yl)sulfonyl]phenyl}-1-methyl-3-propyl-1H,6H,7H-pyrazolo[4,3-d]pyrimidin-7-one

• ChemBase ID: 166239
• Molecular Formular: C20H26N6O4S
• Molecular Mass: 446.52324
• Monoisotopic Mass: 446.17362434
• SMILES: C1N(CCN(C1)S(=O)(=O)c1ccc(c(c1)c1nc2c(c(=O)[nH]1)n(nc2CCC)C)O)C
• Canonical SMILES: CCCc1nn(c2c1nc([nH]c2=O)c1cc(ccc1O)S(=O)(=O)N1CCN(CC1)C)C
• InChI: InChI=1S/C20H26N6O4S/c1-4-5-15-17-18(25(3)23-15)20(28)22-19(21-17)14-12-13(6-7-16(14)27)31(29,30)26-10-8-24(2)9-11-26/h6-7,12,27H,4-5,8-11H2,1-3H3,(H,21,22,28)
• InChIKey: LTNJUPYNXDNXBO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-{2-hydroxy-5-[(4-methylpiperazin-1-yl)sulfonyl]phenyl}-1-methyl-3-propyl-1H,6H,7H-pyrazolo[4,3-d]pyrimidin-7-one
• IUPAC Traditional name: 5-[2-hydroxy-5-(4-methylpiperazin-1-ylsulfonyl)phenyl]-1-methyl-3-propyl-6H-pyrazolo[4,3-d]pyrimidin-7-one
• Synonyms: 5-[2-Hydroxy-5-(4-methylpiperazinylsulphonyl)phenyl]1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyramidin-7-one; 5-[2-Hydroxy-5-[[4-(methyl)-1-piperazinyl]sulfonyl]phenyl]-1,6-dihydro-1-methyl-3-propyl-7H-pyrazolo[4,3-d]pyrimidin-7-one; Desethyl Sildenafil

Database IDs

• CAS Number: 139755-91-2
• PubChem SID: 162260372
• PubChem CID: 21250748

CALCULATED PROPERTIES

• Acid pKa: 7.517925
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): 0.23335357
• LogD (pH = 7.4): 0.58300954
• Log P: 0.6918116
• Molar Refractivity: 130.643 cm^3
• Polarizability: 44.560825 Å^3
• Polar Surface Area: 120.13 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Aqueous Base; DMSO (Sparingly)
• Apperance: Off-White Solid
• Melting Point: 279-281°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D289600

A metabolite of Sildenafil (S435000), an orally active selective type 5 cGMP phosphodiesterase inhibitor.

REFERENCES

• Terrett, N.K., et al.: Bioorg. Med. Chem. Lett., 6, 1819 (1996)
• Goldstein, I., et al.: N. Engl. J. Med., 338, 1397 (1998)