2-amino-9-[(2R,4R,5R)-4-hydroxy-5-[hydroxy(13C)methyl](2,3,4,5-13C4)oxolan-2-yl]-6,9-dihydro(2,4,5,6,8-13C5,1,3,7,9-15N4)-1H-purin-6-one

• ChemBase ID: 165969
• Molecular Formular: C10H13N5O4
• Molecular Mass: 282.13491287
• Monoisotopic Mass: 282.11547677
• SMILES: [15nH]1[13c]([15n][13c]2[13c]([13c]1=O)[15n][13cH][15n]2[13C@H]1[13CH2][13C@H]([13C@H](O1)[13CH2]O)O)[15NH2]
• Canonical SMILES: O[13CH2][13C@H]1O[13C@H]([13CH2][13C@H]1O)[15n]1[13cH][15n][13c]2[13c]1[15n][13c]([15NH2])[15nH][13c]2=O
• InChI: InChI=1S/C10H13N5O4/c11-10-13-8-7(9(18)14-10)12-3-15(8)6-1-4(17)5(2-16)19-6/h3-6,16-17H,1-2H2,(H3,11,13,14,18)/t4-,5-,6-/m1/s1/i1+1,2+1,3+1,4+1,5+1,6+1,7+1,8+1,9+1,10+1,11+1,12+1,13+1,14+1,15+1
• InChIKey: YKBGVTZYEHREMT-XBTGYIMLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-9-[(2R,4R,5R)-4-hydroxy-5-[hydroxy(^1^3C)methyl](2,3,4,5-^1^3C₄)oxolan-2-yl]-6,9-dihydro(2,4,5,6,8-^1^3C₅,1,3,7,9-^1^5N₄)-1H-purin-6-one
• IUPAC Traditional name: 2-amino-9-[(2R,4R,5R)-4-hydroxy-5-[hydroxy(^1^3C)methyl](2,3,4,5-^1^3C₄)oxolan-2-yl](2,4,5,6,8-^1^3C₅,1,3,7,9-^1^5N₄)-1H-purin-6-one
• Synonyms: 9-(2-Deoxy-β-D-erythro-pentofuranosyl)guanine-13C10,15N5; Deoxyguanosine-13C10,15N5; Guanine Deoxyriboside-13C10,15N5; NSC 22837-13C10,15N5; 2'-Deoxyguanosine-13C10,15N5

Database IDs

• PubChem SID: 162260102
• PubChem CID: 71315482

CALCULATED PROPERTIES

• Acid pKa: 10.158529
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -1.8056743
• LogD (pH = 7.4): -1.8062477
• Log P: -1.8055801
• Molar Refractivity: 63.1104 cm^3
• Polarizability: 23.620188 Å^3
• Polar Surface Area: 134.99 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D239553

Labelled deoxy anaolgue of the Guanosine, a constituent of nucleic acids.

REFERENCES

• Krenitsky, T.A., et al.: Biochemistry, 20, 3615 (1981)
• Chapeau, M.-C., et al.: Chem. Res. Toxicol., 4, 636 (1981)