5-(5-{[(3R,5S)-3,5-dimethyl(2,2,6,6-2H4)piperazin-1-yl]sulfonyl}-2-ethoxyphenyl)-1-methyl-3-propyl-1H,4H,7H-pyrazolo[4,3-d]pyrimidin-7-one

• ChemBase ID: 172716
• Molecular Formular: C23H32N6O4S
• Molecular Mass: 488.60298
• Monoisotopic Mass: 488.22057453
• SMILES: c1(nc(=O)c2c([nH]1)c(nn2C)CCC)c1c(ccc(c1)S(=O)(=O)N1C[C@@H](N[C@@H](C1)C)C)OCC
• Canonical SMILES: CCCc1nn(c2c1[nH]c(nc2=O)c1cc(ccc1OCC)S(=O)(=O)N1C[C@H](C)N[C@@H](C1)C)C
• InChI: InChI=1S/C23H32N6O4S/c1-6-8-18-20-21(28(5)27-18)23(30)26-22(25-20)17-11-16(9-10-19(17)33-7-2)34(31,32)29-12-14(3)24-15(4)13-29/h9-11,14-15,24H,6-8,12-13H2,1-5H3,(H,25,26,30)/t14-,15+
• InChIKey: NFSWSZIPXJAYLR-GASCZTMLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(5-{[(3R,5S)-3,5-dimethyl(2,2,6,6-^2H₄)piperazin-1-yl]sulfonyl}-2-ethoxyphenyl)-1-methyl-3-propyl-1H,4H,7H-pyrazolo[4,3-d]pyrimidin-7-one
• IUPAC Traditional name: 5-{5-[(3R,5S)-3,5-dimethyl(2,2,6,6-^2H₄)piperazin-1-ylsulfonyl]-2-ethoxyphenyl}-1-methyl-3-propyl-4H-pyrazolo[4,3-d]pyrimidin-7-one
• Synonyms: rel-5-[5-[[(3R,5S)-3,5-Dimethyl-1-piperazinyl-d4]sulfonyl]-2-ethoxyphenyl]-1,6-dihydro-1-methyl-3-propyl-7H-pyrazolo[4,3-d]pyrimidin-7-one; Aildenafil-d4; Methisosildenafil-d4

Database IDs

• PubChem SID: 164228626
• PubChem CID: 71749983

CALCULATED PROPERTIES

• Acid pKa: 6.9884095
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): 0.50509125
• LogD (pH = 7.4): 1.7131164
• Log P: 1.6552975
• Molar Refractivity: 142.9834 cm^3
• Polarizability: 50.329212 Å^3
• Polar Surface Area: 117.92 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M225937

Labelled Methisosildenafil. A new Sildenafil (S435000) analogue detected as an adulterant in an herbal dietary supplement.

REFERENCES

• Gratz, S., et al.: J. Pharm. Biomed. Anal., 36, 525 (2004)
• Lai, K., et al.: J. Food Drug Anal., 14, 19 (2004)
• Oh, S., et al.: J. Toxicol. Environ. Health, 69, 1951 (2004)