(2R,4R,5R)-2-{5-amino-7-methyl-2,6,7,9,11-pentaazatricyclo[6.3.1.04,12]dodeca-1(11),3,5,8(12),9-pentaen-2-yl}-5-(hydroxymethyl)oxolane-3,4-diol

• ChemBase ID: 178974
• Molecular Formular: C13H16N6O4
• Molecular Mass: 320.30394
• Monoisotopic Mass: 320.12330302
• SMILES: n1cnc2c3c1n(nc(c3cn2[C@H]1C([C@H]([C@H](O1)CO)O)O)N)C
• Canonical SMILES: OC[C@H]1O[C@H](C([C@H]1O)O)n1cc2c3c1ncnc3n(nc2N)C
• InChI: InChI=1S/C13H16N6O4/c1-18-11-7-5(10(14)17-18)2-19(12(7)16-4-15-11)13-9(22)8(21)6(3-20)23-13/h2,4,6,8-9,13,20-22H,3H2,1H3,(H2,14,17)/t6-,8+,9?,13-/m1/s1
• InChIKey: HOGVTUZUJGHKPL-MAADLVNMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4R,5R)-2-{5-amino-7-methyl-2,6,7,9,11-pentaazatricyclo[6.3.1.0^4,^1^2]dodeca-1(11),3,5,8(12),9-pentaen-2-yl}-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: (2R,4R,5R)-2-{5-amino-7-methyl-2,6,7,9,11-pentaazatricyclo[6.3.1.0^4,^1^2]dodeca-1(11),3,5,8(12),9-pentaen-2-yl}-5-(hydroxymethyl)oxolane-3,4-diol
• Synonyms: 1,5-Dihydro-5-methyl-1-β-D-ribofuranosyl-1,4,5,6,8-pentaazaacenaphthylen-3-amine; 6-Amino-4-methyl-8-(β-D-ribofuranosyl)-4H,8H-pyrrolo[4,3,2-de]pyrimido[4,5-c]pyridazine; API 2; NSC 154020; TCN; Triciribine

Database IDs

• CAS Number: 35943-35-2
• PubChem SID: 164234884
• PubChem CID: 56684105

CALCULATED PROPERTIES

• Acid pKa: 12.45568
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -4.271866
• LogD (pH = 7.4): -2.4411151
• Log P: -1.4642601
• Molar Refractivity: 90.5553 cm^3
• Polarizability: 30.775778 Å^3
• Polar Surface Area: 144.47 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T774245

Triciribine is an antitumor tricyclic nucleoside. Triciribine acts as a potent, small-molecule inhibitor of AKT phosphorylation in subjects with solid tumors contining activated AKT. Triciribine is also a selective inhibitor of HIV-1 and HIV-2, including

REFERENCES

• Garrett, C.R. et al.: Invest. New Drugs, 29, 1381 (2011)
• Ptak, R.G. et al.: AIDS Res. Human Retrovir., 14, 1315 (2011)
• Bennett, L.L. et al.: BIochem. Pharmacol., 27, 233 (2011)