(2R,8R)-6-amino-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: 160487
• Molecular Formular: C21H18N4O4
• Molecular Mass: 390.39202
• Monoisotopic Mass: 390.13280508
• SMILES: c12c([C@H](N3[C@H](C1)C(=O)N(CC3=O)N)c1ccc3c(c1)OCO3)[nH]c1c2cccc1
• Canonical SMILES: O=C1N(N)CC(=O)N2[C@@H]1Cc1c([C@H]2c2ccc3c(c2)OCO3)[nH]c2c1cccc2
• InChI: InChI=1S/C21H18N4O4/c22-24-9-18(26)25-15(21(24)27)8-13-12-3-1-2-4-14(12)23-19(13)20(25)11-5-6-16-17(7-11)29-10-28-16/h1-7,15,20,23H,8-10,22H2/t15-,20-/m1/s1
• InChIKey: VUKJGAVIWMPOOJ-FOIQADDNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,8R)-6-amino-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)-6-amino-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)-2-Amino-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; Amino Tadalafil

Database IDs

• CAS Number: 385769-84-6
• PubChem SID: 162254622
• PubChem CID: 10178467

CALCULATED PROPERTIES

• Acid pKa: 15.163643
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.1182015
• LogD (pH = 7.4): 1.1191761
• Log P: 1.1191885
• Molar Refractivity: 103.669 cm^3
• Polarizability: 41.018093 Å^3
• Polar Surface Area: 100.89 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 280-282°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A629550

A drug analog of Tadalafil.

REFERENCES

• Kim, D., et al.: Bioorg. Med. Chem., 9, 1895 (2001)
• Tseng, M., et al.: J. Food Drug. Anal., 10, 112 (2001)
• Blount, M., et al.: Mol. Pharmacol., 66, 144 (2001)