2-amino-9-[(1S,3R)-4-(hydroxydimethylsilyl)-3-(hydroxymethyl)-2-methylidenecyclopentyl]-6,9-dihydro-1H-purin-6-one

• ChemBase ID: 165606
• Molecular Formular: C14H21N5O3Si
• Molecular Mass: 335.43374
• Monoisotopic Mass: 335.14136609
• SMILES: C1C([C@H](C(=C)[C@H]1n1c2c(nc1)c(=O)[nH]c(n2)N)CO)[Si](O)(C)C
• Canonical SMILES: OC[C@H]1C(=C)[C@H](CC1[Si](O)(C)C)n1cnc2c1nc(N)[nH]c2=O
• InChI: InChI=1S/C14H21N5O3Si/c1-7-8(5-20)10(23(2,3)22)4-9(7)19-6-16-11-12(19)17-14(15)18-13(11)21/h6,8-10,20,22H,1,4-5H2,2-3H3,(H3,15,17,18,21)/t8-,9-,10?/m0/s1
• InChIKey: DEHZIARQYIUCOF-XMCUXHSSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-9-[(1S,3R)-4-(hydroxydimethylsilyl)-3-(hydroxymethyl)-2-methylidenecyclopentyl]-6,9-dihydro-1H-purin-6-one
• IUPAC Traditional name: 2-amino-9-[(1S,3R)-4-(hydroxydimethylsilyl)-3-(hydroxymethyl)-2-methylidenecyclopentyl]-1H-purin-6-one
• Synonyms: 2-Amino-1,9-dihydro-9-[(1S,3R,4S)-4-(hydroxydimethylsilyl)-3-(hydroxymethyl)-2-methylenecyclopentyl]-6H-purin-6-one; 4-Dehydroxy-4-dimethylhydroxysilyl Entecavir

Database IDs

• CAS Number: 870614-82-7
• PubChem SID: 162259739
• PubChem CID: 57602785

CALCULATED PROPERTIES

• Acid pKa: 10.166318
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -1.1171905
• LogD (pH = 7.4): -1.117788
• Log P: -1.1171
• Molar Refractivity: 83.0222 cm^3
• Polarizability: 32.8306 Å^3
• Polar Surface Area: 125.76 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D229180

4-Dehydroxy-4-dimethylhydroxysilyl Entecavir is an impurity of Entecavir (E558900).

REFERENCES

• Miyaji., et al.: Tetrahedr. Lett., 32, 4557 (1991)
• Bisacchi., et al.: Med. Chem. Lett., 7, 127 (1991)