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

• ChemBase ID: 166576
• Molecular Formular: C21H17N3O4
• Molecular Mass: 375.37738
• Monoisotopic Mass: 375.12190604
• SMILES: c12c([C@H](N3[C@H](C1)C(=O)NCC3=O)c1ccc3c(c1)OCO3)[nH]c1c2cccc1
• Canonical SMILES: O=C1NCC(=O)N2[C@@H]1Cc1c([C@H]2c2ccc3c(c2)OCO3)[nH]c2c1cccc2
• InChI: InChI=1S/C21H17N3O4/c25-18-9-22-21(26)15-8-13-12-3-1-2-4-14(12)23-19(13)20(24(15)18)11-5-6-16-17(7-11)28-10-27-16/h1-7,15,20,23H,8-10H2,(H,22,26)/t15-,20-/m1/s1
• InChIKey: XHDLVMPUSXRZOS-FOIQADDNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,8R)-2-(2H-1,3-benzodioxol-5-yl)-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,8R)-2-(2H-1,3-benzodioxol-5-yl)-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)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione; (6R-trans)-6-(1,3-Benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione; Nortadalafil; N-Desmethyl Tadalafil

Database IDs

• CAS Number: 171596-36-4
• PubChem SID: 162260709
• PubChem CID: 9820973

CALCULATED PROPERTIES

• Acid pKa: 11.094216
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.4156632
• LogD (pH = 7.4): 1.4155865
• Log P: 1.4156643
• Molar Refractivity: 99.1849 cm^3
• Polarizability: 39.58844 Å^3
• Polar Surface Area: 83.66 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D293800

A N-desmethyl analogue of the human PDE5 inhibitor Tadalafil (T004500). A potential antiplasmodial drug.

REFERENCES

• Beghyn, T. et al.: Bioorg. Med. Chem. Lett., 17, 789 (2007)
• Daugan, A. et al.: J. Med. Chem., 46, 4533 (2007)