(2R,3R,5R)-5-[2-amino-6-(2-hydroxypropoxy)-9H-purin-9-yl]-2-(hydroxymethyl)oxolan-3-ol

• ChemBase ID: 171229
• Molecular Formular: C13H19N5O5
• Molecular Mass: 325.32046
• Monoisotopic Mass: 325.13861873
• SMILES: n1c(nc2c(c1OCC(O)C)ncn2[C@H]1C[C@H]([C@H](O1)CO)O)N
• Canonical SMILES: OC[C@H]1O[C@H](C[C@H]1O)n1cnc2c1nc(N)nc2OCC(O)C
• InChI: InChI=1S/C13H19N5O5/c1-6(20)4-22-12-10-11(16-13(14)17-12)18(5-15-10)9-2-7(21)8(3-19)23-9/h5-9,19-21H,2-4H2,1H3,(H2,14,16,17)/t6?,7-,8-,9-/m1/s1
• InChIKey: HLFWWFZDUMLOEE-FUZJYRNYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,5R)-5-[2-amino-6-(2-hydroxypropoxy)-9H-purin-9-yl]-2-(hydroxymethyl)oxolan-3-ol
• IUPAC Traditional name: (2R,3R,5R)-5-[2-amino-6-(2-hydroxypropoxy)purin-9-yl]-2-(hydroxymethyl)oxolan-3-ol
• Synonyms: O6-(2-Hydroxypropyl)-2'-deoxyguanosine

Database IDs

• CAS Number: 1327339-22-9
• PubChem SID: 164227139
• PubChem CID: 71749311

CALCULATED PROPERTIES

• Acid pKa: 13.838173
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -0.9427467
• LogD (pH = 7.4): -0.9427383
• Log P: -0.94273806
• Molar Refractivity: 78.8052 cm^3
• Polarizability: 30.748106 Å^3
• Polar Surface Area: 148.77 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H952615

O6-(2-Hydroxypropyl)-2’-deoxyguanosine is a mutagenic O6-alkylguanine adduct that induces mismatch repair-mediated toxicity.

REFERENCES

• Mazon, G. et al.: Proc. Nat. Acad. Sci. USA, 107, S18050 (2010)