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

• ChemBase ID: 178043
• Molecular Formular: C22H19N3O4
• Molecular Mass: 389.40396
• Monoisotopic Mass: 389.1375561
• SMILES: c12c([C@@H](N3[C@@H](C1)C(=O)N(CC3=O)C)c1ccc3c(c1)OCO3)[nH]c1c2cccc1
• Canonical SMILES: O=C1N(C)CC(=O)N2[C@H]1Cc1c([C@@H]2c2ccc3c(c2)OCO3)[nH]c2c1cccc2
• InChI: InChI=1S/C22H19N3O4/c1-24-10-19(26)25-16(22(24)27)9-14-13-4-2-3-5-15(13)23-20(14)21(25)12-6-7-17-18(8-12)29-11-28-17/h2-8,16,21,23H,9-11H2,1H3/t16-,21-/m0/s1
• InChIKey: WOXKDUGGOYFFRN-KKSFZXQISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,8S)-2-(2H-1,3-benzodioxol-5-yl)-6-methyl-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: (2S,8S)-2-(2H-1,3-benzodioxol-5-yl)-6-methyl-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: (6S,12aS)-6-(1,3-Benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methyl-pyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione; L-Tadalafil; L-Tildenafil; ent-Tadalafil

Database IDs

• CAS Number: 629652-72-8
• PubChem SID: 164233953
• PubChem CID: 9908373

CALCULATED PROPERTIES

• Acid pKa: 15.16992
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.6393403
• LogD (pH = 7.4): 1.6393403
• Log P: 1.6393403
• Molar Refractivity: 104.0816 cm^3
• Polarizability: 41.42806 Å^3
• Polar Surface Area: 74.87 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White Solid
• Melting Point: 278-282°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - T004505

Tadalafil (T004500) analog.

REFERENCES

• Daugan, A., et al.: J. Med. Chem., 46, 4533 (2003)
• Jiang, W., et al.: Bioorg. Med. Chem., 12, 1505 (2003)