({[({[(2R,3S,4R,5R)-5-[4-amino-3-(naphthalen-1-ylmethyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid

• ChemBase ID: 160331
• Molecular Formular: C21H24N5O13P3
• Molecular Mass: 647.362243
• Monoisotopic Mass: 647.05834574
• SMILES: n1cnc2c(c1N)c(nn2[C@H]1[C@@H]([C@@H]([C@H](O1)COP(=O)(OP(=O)(O)OP(=O)(O)O)O)O)O)Cc1cccc2c1cccc2
• Canonical SMILES: O[C@@H]1[C@H](O)[C@H](O[C@H]1n1nc(c2c1ncnc2N)Cc1cccc2c1cccc2)COP(=O)(OP(=O)(OP(=O)(O)O)O)O
• InChI: InChI=1S/C21H24N5O13P3/c22-19-16-14(8-12-6-3-5-11-4-1-2-7-13(11)12)25-26(20(16)24-10-23-19)21-18(28)17(27)15(37-21)9-36-41(32,33)39-42(34,35)38-40(29,30)31/h1-7,10,15,17-18,21,27-28H,8-9H2,(H,32,33)(H,34,35)(H2,22,23,24)(H2,29,30,31)/t15-,17-,18-,21-/m1/s1
• InChIKey: NPKUTVNELHUNPS-QTQZEZTPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ({[({[(2R,3S,4R,5R)-5-[4-amino-3-(naphthalen-1-ylmethyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
• IUPAC Traditional name: ({[(2R,3S,4R,5R)-5-[4-amino-3-(naphthalen-1-ylmethyl)pyrazolo[3,4-d]pyrimidin-1-yl]-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxyphosphonic acid
• Synonyms: 1-[5-O-[Hydroxy[[hydroxy(phosphonooxy)phosphinyl]oxy]phosphinyl]-β-D-ribofuranosyl]-3-(1-naphthalenylmethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine; 3-(1-NM)-PPTP; 4-Amino-3-(1-naphthylmethyl)-1H-pyrazolo[3,4-d]pyrimidine-1-(β-D-ribofuranosyl-5'-triphosphate)

Database IDs

• CAS Number: 476371-81-0
• PubChem SID: 162254466
• PubChem CID: 71313320

CALCULATED PROPERTIES

• Acid pKa: 0.89527714
• H Acceptors: 14
• H Donor: 7
• LogD (pH = 5.5): -7.3805733
• LogD (pH = 7.4): -7.601269
• Log P: -3.1278446
• Molar Refractivity: 153.0018 cm^3
• Polarizability: 56.84384 Å^3
• Polar Surface Area: 279.13 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A618360

An inhibitor scaffolds as new allele specific kinase substrates.

REFERENCES

• Hunter, T., et al.: Cell, 80, 225 (1995)
• Liu, Y., et al.: Bioorg. Med. Chem., 6, 1219 (1995)
• Davies, S., et al.: Biochem. J., 351, 95 (1995)
• Shah, K., et al.: Chem. Biol., 9, 35 (1995)