(2R,4R,5R)-2-(2,6-diamino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

• ChemBase ID: 159797
• Molecular Formular: C10H14N6O4
• Molecular Mass: 282.25596
• Monoisotopic Mass: 282.10765296
• SMILES: n1c(nc2c(c1N)ncn2[C@H]1C([C@H]([C@H](O1)CO)O)O)N
• Canonical SMILES: OC[C@H]1O[C@H](C([C@H]1O)O)n1cnc2c1nc(N)nc2N
• InChI: InChI=1S/C10H14N6O4/c11-7-4-8(15-10(12)14-7)16(2-13-4)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H4,11,12,14,15)/t3-,5+,6?,9-/m1/s1
• InChIKey: ZDTFMPXQUSBYRL-ACJOCUEISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4R,5R)-2-(2,6-diamino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: (2R,4R,5R)-2-(2,6-diaminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• Synonyms: 2,6-Diamino-9-β-D-ribofuranosyl-9H-purine; 2,6-Diaminonebularine; 9-β-Ribosyl-2,6-diaminopurine; 2,6-Diaminopurine Riboside; 2,6-Diaminopurinosine; NSC 7363; 2-Amino Adenosine

Database IDs

• CAS Number: 2096-10-8
• PubChem SID: 162253932
• PubChem CID: 45038102

CALCULATED PROPERTIES

• Acid pKa: 12.453983
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -2.2412477
• LogD (pH = 7.4): -2.2411094
• Log P: -2.241104
• Molar Refractivity: 67.842 cm^3
• Polarizability: 25.71031 Å^3
• Polar Surface Area: 165.56 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Hot Water; Methanol
• Apperance: White Powder
• Melting Point: 241-243°C (dec.)

DETAILS

Toronto Research Chemicals - A580360

A nucleoside analog as inhibitor or substrate of adenosine kinase from M. tuberculosis.

REFERENCES

• Barrow, E., et al.: J. Antimicrob. Chemother., 252, 801 (2003)
• Long, M., et al.: J. Bacteriol., 185, 6548 (2003)
• Yadav, V., et al.: J. Med. Chem., 47, 1987 (2003)