(2R,8S)-2-(2H-1,3-benzodioxol-5-yl)-6-butyl-3,6,17-triazatetracyclo[8.7.0.03,8.011,16]heptadeca-1(10),11,13,15-tetraene-4,7-dione

• ChemBase ID: 163478
• Molecular Formular: C25H25N3O4
• Molecular Mass: 431.4837
• Monoisotopic Mass: 431.1845063
• SMILES: c12c([C@H](N3[C@@H](C1)C(=O)N(CC3=O)CCCC)c1ccc3c(c1)OCO3)[nH]c1c2cccc1
• Canonical SMILES: CCCCN1CC(=O)N2[C@H](C1=O)Cc1c([C@H]2c2ccc3c(c2)OCO3)[nH]c2c1cccc2
• InChI: InChI=1S/C25H25N3O4/c1-2-3-10-27-13-22(29)28-19(25(27)30)12-17-16-6-4-5-7-18(16)26-23(17)24(28)15-8-9-20-21(11-15)32-14-31-20/h4-9,11,19,24,26H,2-3,10,12-14H2,1H3/t19-,24+/m0/s1
• InChIKey: KYRHHTFKIXWPJS-YADARESESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,8S)-2-(2H-1,3-benzodioxol-5-yl)-6-butyl-3,6,17-triazatetracyclo[8.7.0.0^3,^8.0^1^1,^1^6]heptadeca-1(10),11,13,15-tetraene-4,7-dione
• IUPAC Traditional name: (2R,8S)-2-(2H-1,3-benzodioxol-5-yl)-6-butyl-3,6,17-triazatetracyclo[8.7.0.0^3,^8.0^1^1,^1^6]heptadeca-1(10),11,13,15-tetraene-4,7-dione
• Synonyms: (6R,12aR)-6-(1,3-Benzodioxol-5-yl)-2-butyl-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione; N-Butyl Nortadalafil

Database IDs

• CAS Number: 171596-31-9
• PubChem SID: 162257613
• PubChem CID: 71314452

CALCULATED PROPERTIES

• Acid pKa: 15.16991
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.9632394
• LogD (pH = 7.4): 2.9632394
• Log P: 2.9632394
• Molar Refractivity: 117.9552 cm^3
• Polarizability: 46.950043 Å^3
• Polar Surface Area: 74.87 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B693585

Tadalafil analog.

REFERENCES

• Daugan, A., et al.: J. Med. Chem., 46, 4533 (2003)