2-amino-9-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro(2-13C,1-15N)-1H-purin-6-one

• ChemBase ID: 165968
• Molecular Formular: C10H13N5O4
• Molecular Mass: 270.22079263
• Monoisotopic Mass: 270.09417855
• SMILES: [15nH]1[13c](nc2c(c1=O)ncn2[C@H]1C[C@H]([C@H](O1)CO)O)[15NH2]
• Canonical SMILES: OC[C@H]1O[C@H](C[C@H]1O)n1cnc2c1n[13c]([15NH2])[15nH]c2=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/i10+1,11+1,14+1
• InChIKey: YKBGVTZYEHREMT-DWUUCWEGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-9-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro(2-^1^3C,1-^1^5N)-1H-purin-6-one
• IUPAC Traditional name: 2-amino-9-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl](2-^1^3C,1-^1^5N)-1H-purin-6-one
• Synonyms: 9-(2-Deoxy-β-D-erythro-pentofuranosyl)guanine-13C,15N2; Deoxyguanosine-13C,15N2; Guanine Deoxyriboside-13C,15N2; NSC 22837-13C,15N2; 2'-Deoxyguanosine-13C,15N2

Database IDs

• PubChem SID: 162260101
• PubChem CID: 46780629

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

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: White Solid
• Melting Point: >230°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D239552

Labelled nucleoside.

REFERENCES

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