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

• ChemBase ID: 175806
• Molecular Formular: C29H33N3O4
• Molecular Mass: 487.59002
• Monoisotopic Mass: 487.24710655
• SMILES: c12c([C@H](N3[C@@H](C1)C(=O)N(CC3=O)CCCCCCCC)c1ccc3c(c1)OCO3)[nH]c1c2cccc1
• Canonical SMILES: CCCCCCCCN1CC(=O)N2[C@H](C1=O)Cc1c([C@H]2c2ccc3c(c2)OCO3)[nH]c2c1cccc2
• InChI: InChI=1S/C29H33N3O4/c1-2-3-4-5-6-9-14-31-17-26(33)32-23(29(31)34)16-21-20-10-7-8-11-22(20)30-27(21)28(32)19-12-13-24-25(15-19)36-18-35-24/h7-8,10-13,15,23,28,30H,2-6,9,14,16-18H2,1H3/t23-,28+/m0/s1
• InChIKey: JIMWYJMUPCVOFA-NEKDWFFYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,8S)-2-(2H-1,3-benzodioxol-5-yl)-6-octyl-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-octyl-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-hexahydro-2-octylpyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione; N-Octyl Nortadalafil

Database IDs

• CAS Number: 1173706-35-8
• PubChem SID: 164231716
• PubChem CID: 71751293

CALCULATED PROPERTIES

• Acid pKa: 15.16991
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 4.741514
• LogD (pH = 7.4): 4.741514
• Log P: 4.741514
• Molar Refractivity: 136.3592 cm^3
• Polarizability: 54.318184 Å^3
• Polar Surface Area: 74.87 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - O241350

Tadalafil analog, isolated from medicinal dietary supplements.

REFERENCES

• Hasegawa, T., et al.: Chem. Pharm. Bull., 57, 185 (2009)