(2R,4R,5R)-2-{4-amino-3-benzyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-5-(hydroxymethyl)oxolane-3,4-diol

• ChemBase ID: 159841
• Molecular Formular: C17H19N5O4
• Molecular Mass: 357.36386
• Monoisotopic Mass: 357.14370411
• SMILES: n1cnc2c(c1N)c(nn2[C@H]1C([C@H]([C@H](O1)CO)O)O)Cc1ccccc1
• Canonical SMILES: OC[C@H]1O[C@H](C([C@H]1O)O)n1nc(c2c1ncnc2N)Cc1ccccc1
• InChI: InChI=1S/C17H19N5O4/c18-15-12-10(6-9-4-2-1-3-5-9)21-22(16(12)20-8-19-15)17-14(25)13(24)11(7-23)26-17/h1-5,8,11,13-14,17,23-25H,6-7H2,(H2,18,19,20)/t11-,13+,14?,17-/m1/s1
• InChIKey: HNFBXNKTEDTNPF-NUKIEUHSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4R,5R)-2-{4-amino-3-benzyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: (2R,4R,5R)-2-{4-amino-3-benzylpyrazolo[3,4-d]pyrimidin-1-yl}-5-(hydroxymethyl)oxolane-3,4-diol
• Synonyms: 3-(Phenylmethyl)-1-β-D-ribofuranosyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine; 4-Amino-3-benzyl-1H-pyrazolo[3,4-d]pyrimidine 1-β-D-Ribofuranose

Database IDs

• CAS Number: 476371-76-3
• PubChem SID: 162253976
• PubChem CID: 71313154

CALCULATED PROPERTIES

• Acid pKa: 12.420045
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -0.9881819
• LogD (pH = 7.4): -0.21811621
• Log P: -0.18845019
• Molar Refractivity: 103.9329 cm^3
• Polarizability: 35.775776 Å^3
• Polar Surface Area: 139.54 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A600250

An inhibitor scaffolds as new allele specific kinase substrates.

REFERENCES

• Hunter, T., et al.: Cell, 100, 113 (2000)
• Habelhah, H., et al.: J. Biol. Chem., 276, 18090 (2000)
• Shah, K., et al.: Chem. Biol., 9, 33 (2000)