(2R,3R,5R)-5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)(2,3,4,5-13C4)oxolan-3-ol hydrate

• ChemBase ID: 165844
• Molecular Formular: C10H15N5O4
• Molecular Mass: 273.22781935
• Monoisotopic Mass: 273.12582334
• SMILES: O.[13C@H]1([13CH2][13C@@H](O[13C@@H]1CO)n1c2c(c(ncn2)N)nc1)O
• Canonical SMILES: OC[13C@H]1O[13C@H]([13CH2][13C@H]1O)n1cnc2c1ncnc2N.O
• InChI: InChI=1S/C10H13N5O3.H2O/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(17)6(2-16)18-7;/h3-7,16-17H,1-2H2,(H2,11,12,13);1H2/t5-,6-,7-;/m1./s1/i1+1,5+1,6+1,7+1
• InChIKey: WZJWHIMNXWKNTO-PEBSFZIHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,5R)-5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)(2,3,4,5-^1^3C₄)oxolan-3-ol hydrate
• IUPAC Traditional name: (2R,3R,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)(2,3,4,5-^1^3C₄)oxolan-3-ol hydrate
• Synonyms: 2'-Deoxyadenosine Monohydrate-13C5; 9-(2-Deoxy-β-D-erythro-pentofuranosyl)adenine-13C5; 9-(2-Deoxy-β-D-erythro-pentofuranosyl)-9H-purin-6-amine-13C5 Hydrate; Adenine Deoxyribonucleoside-13C5 Hydrate; Adenine Deoxyribose-13C5 Hydrate; Adenyldeoxyriboside-13C5 Hydrate; Deoxyadenosine-13C5 Hydrate; Desoxyadenosine-13C5 Hydrate; NSC 141848; NSC 143510; NSC 83258; dA; 1-(6-Amino-9H-purin-9-yl)-1,2-dideoxy-β-D-ribofuranose-13C5 Hydrate; 2-Deoxyadenine-9-β-D-erythro-pento-furanoside-13C5 Hydrate; 2'-Deoxy-β-D-adenosine-13C5 Monohydrate

Database IDs

• CAS Number: 478510-79-1
• PubChem SID: 162259977
• PubChem CID: 71315423

CALCULATED PROPERTIES

• Acid pKa: 13.886734
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -1.3084735
• LogD (pH = 7.4): -1.1920375
• Log P: -1.1903259
• Molar Refractivity: 61.6849 cm^3
• Polarizability: 23.860369 Å^3
• Polar Surface Area: 119.31 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D231622

Used in the synthesis of labelled 5'-modified 2'-deoxyadenosine analogues as anti-hepatitis C virus agents.

REFERENCES

• Gordon, C., et al.: J. Med. Chem., 48, 1 (2005)
• Ikejiri, M., et al.: Bioorg. Med. Chem., 15, 6882 (2005)