(2R,3R,5R)-5-{2-amino-6-[(1-hydroxypropan-2-yl)oxy]-9H-purin-9-yl}-2-(hydroxymethyl)oxolan-3-ol

• ChemBase ID: 170815
• Molecular Formular: C13H19N5O5
• Molecular Mass: 325.32046
• Monoisotopic Mass: 325.13861873
• SMILES: n1c(nc2c(c1OC(CO)C)ncn2[C@H]1C[C@H]([C@H](O1)CO)O)N
• Canonical SMILES: OCC(Oc1nc(N)nc2c1ncn2[C@@H]1O[C@@H]([C@@H](C1)O)CO)C
• InChI: InChI=1S/C13H19N5O5/c1-6(3-19)22-12-10-11(16-13(14)17-12)18(5-15-10)9-2-7(21)8(4-20)23-9/h5-9,19-21H,2-4H2,1H3,(H2,14,16,17)/t6?,7-,8-,9-/m1/s1
• InChIKey: DPRKTPGJARCDPS-FUZJYRNYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,5R)-5-{2-amino-6-[(1-hydroxypropan-2-yl)oxy]-9H-purin-9-yl}-2-(hydroxymethyl)oxolan-3-ol
• IUPAC Traditional name: (2R,3R,5R)-5-{2-amino-6-[(1-hydroxypropan-2-yl)oxy]purin-9-yl}-2-(hydroxymethyl)oxolan-3-ol
• Synonyms: O6-(2-Hydroxy-1-methylethyl)-2'-deoxyguanosine

Database IDs

• CAS Number: 1327339-21-8
• PubChem SID: 164226725
• PubChem CID: 71749149

CALCULATED PROPERTIES

• Acid pKa: 13.817993
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -0.9427466
• LogD (pH = 7.4): -0.9427383
• Log P: -0.94273806
• Molar Refractivity: 78.8052 cm^3
• Polarizability: 30.74808 Å^3
• Polar Surface Area: 148.77 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H946980

O6-(2-Hydroxy-1-methylethyl)-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)