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

• ChemBase ID: 159842
• Molecular Formular: C17H22N5O13P3
• Molecular Mass: 597.303563
• Monoisotopic Mass: 597.04269568
• 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)Cc1ccccc1
• Canonical SMILES: O[C@@H]1[C@H](O)[C@H](O[C@H]1n1nc(c2c1ncnc2N)Cc1ccccc1)COP(=O)(OP(=O)(OP(=O)(O)O)O)O
• InChI: InChI=1S/C17H22N5O13P3/c18-15-12-10(6-9-4-2-1-3-5-9)21-22(16(12)20-8-19-15)17-14(24)13(23)11(33-17)7-32-37(28,29)35-38(30,31)34-36(25,26)27/h1-5,8,11,13-14,17,23-24H,6-7H2,(H,28,29)(H,30,31)(H2,18,19,20)(H2,25,26,27)/t11-,13-,14-,17-/m1/s1
• InChIKey: ZJFXXUXEJRUXPF-LSCFUAHRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ({[({[(2R,3S,4R,5R)-5-{4-amino-3-benzyl-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-benzylpyrazolo[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-(phenylmethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine; 4-Amino-3-benzyl-1H-pyrazolo[3,4-d]pyrimidine 1-β-D-Ribofuranosyl 5'-Triphosphate

Database IDs

• CAS Number: 476371-80-9
• PubChem SID: 162253977
• PubChem CID: 71313155

CALCULATED PROPERTIES

• Acid pKa: 0.89527714
• H Acceptors: 14
• H Donor: 7
• LogD (pH = 5.5): -8.370319
• LogD (pH = 7.4): -8.590786
• Log P: -4.1173234
• Molar Refractivity: 136.5516 cm^3
• Polarizability: 49.625607 Å^3
• Polar Surface Area: 279.13 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A600260

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)