1-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H,4H,5H-imidazo[2,1-b]purin-4-one

• ChemBase ID: 168205
• Molecular Formular: C12H13N5O4
• Molecular Mass: 291.26272
• Monoisotopic Mass: 291.09675392
• SMILES: [nH]1c2n(c3c(c1=O)ncn3[C@H]1C[C@H]([C@H](O1)CO)O)ccn2
• Canonical SMILES: OC[C@H]1O[C@H](C[C@H]1O)n1cnc2c1n1ccnc1[nH]c2=O
• InChI: InChI=1S/C12H13N5O4/c18-4-7-6(19)3-8(21-7)17-5-14-9-10(20)15-12-13-1-2-16(12)11(9)17/h1-2,5-8,18-19H,3-4H2,(H,13,15,20)/t6-,7-,8-/m1/s1
• InChIKey: DUHWHZGZQYBCAZ-BWZBUEFSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H,4H,5H-imidazo[2,1-b]purin-4-one
• IUPAC Traditional name: 1-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5H-imidazo[2,1-b]purin-4-one
• Synonyms: 1-(2-Deoxy-β-D-erythro-pentofuranosyl)-1H-imidazo[2,1-b]purin-4(5H)-one; N2,3-Etheno-2'-deoxy Guanosine

Database IDs

• CAS Number: 121055-53-6
• PubChem SID: 162262337
• PubChem CID: 71316440

CALCULATED PROPERTIES

• Acid pKa: 9.82159
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -1.6340802
• LogD (pH = 7.4): -1.6356035
• Log P: -1.634
• Molar Refractivity: 79.8769 cm^3
• Polarizability: 26.47511 Å^3
• Polar Surface Area: 114.43 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: White Solid
• Melting Point: >273°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - E678000

A etheno-substituted purine nucleoside derivative with fluorescent and biochemical properties. Etheno-DNA adducts are promutagenic lesions present in normal animal and human tissues that are believed to be important in the etiol. of cancer related to diet

REFERENCES

• Schlatter, J., et al.: Food Chem. Toxicol., 28, 205 (1990)
• Chen, H., et al.: Chem. Res. Toxicol., 12, 1119 (1990)
• Nair, J., et al.: Mutat. Res., 424, 59 (1990)