(2R,3S,5R)-5-(6-amino-2-methoxy-9H-purin-9-yl)-2-(hydroxymethyl)oxolan-3-ol

• ChemBase ID: 172930
• Molecular Formular: C11H15N5O4
• Molecular Mass: 281.2679
• Monoisotopic Mass: 281.11240399
• SMILES: C1[C@@H]([C@H](O[C@H]1n1c2c(nc1)c(nc(n2)OC)N)CO)O
• Canonical SMILES: OC[C@H]1O[C@H](C[C@@H]1O)n1cnc2c1nc(OC)nc2N
• InChI: InChI=1S/C11H15N5O4/c1-19-11-14-9(12)8-10(15-11)16(4-13-8)7-2-5(18)6(3-17)20-7/h4-7,17-18H,2-3H2,1H3,(H2,12,14,15)/t5-,6+,7+/m0/s1
• InChIKey: HGRICISHTIAZJG-RRKCRQDMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,5R)-5-(6-amino-2-methoxy-9H-purin-9-yl)-2-(hydroxymethyl)oxolan-3-ol
• IUPAC Traditional name: (2R,3S,5R)-5-(6-amino-2-methoxypurin-9-yl)-2-(hydroxymethyl)oxolan-3-ol
• Synonyms: 2'-Deoxy-2-methoxyadenosine; 2-Methoxy-2'-deoxy-β-adenosine; 2-Methoxy-2'-deoxyadenosine; 2-Methoxy-6-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine; 9β-(2-Deoxy-D-ribofuranosyl)-2-methoxyadenine; 2-Methoxy 2'-Deoxyadenosine

Database IDs

• PubChem SID: 164228840
• PubChem CID: 10265713

CALCULATED PROPERTIES

• Acid pKa: 13.88671
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -0.6692263
• LogD (pH = 7.4): -0.6692114
• Log P: -0.66921103
• Molar Refractivity: 68.0941 cm^3
• Polarizability: 26.422659 Å^3
• Polar Surface Area: 128.54 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M262400

A 2-substituted 2’-Deoxyadenosine (D231620). Used in the synthesis of oligonucleotides.

REFERENCES

• Ishikawa, F., et al.: J. Mol. Biol., 70, 475 (1972)
• Hattori, M., et al.: Biochemistry, 13, 2754 (1972)
• Kazimierczuk, Z., et al.: J. Med. Chem., 33, 1683 (1972)