(2R,3R,4R,5S)-2-{4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl}-5-(hydroxymethyl)oxolane-3,4-diol

• ChemBase ID: 2870
• Molecular Formular: C11H14N4O4
• Molecular Mass: 266.25326
• Monoisotopic Mass: 266.10150495
• SMILES: Nc1ncnc2c1ccn2[C@@H]1O[C@@H](CO)[C@H](O)[C@H]1O
• Canonical SMILES: OC[C@@H]1O[C@H]([C@@H]([C@H]1O)O)n1ccc2c1ncnc2N
• InChI: InChI=1S/C11H14N4O4/c12-9-5-1-2-15(10(5)14-4-13-9)11-8(18)7(17)6(3-16)19-11/h1-2,4,6-8,11,16-18H,3H2,(H2,12,13,14)/t6-,7-,8+,11+/m0/s1
• InChIKey: HDZZVAMISRMYHH-LITAXDCLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5S)-2-{4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl}-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: TBC
• Synonyms: 7-deazaadenosine; Tubercidine; 7-Deazadenosine; Toyocamycin; Antibiotic 155B2T; Antibiotic XK 101-1; TBC; TBN; Sparsomycin A; Tubercidin

Database IDs

• CAS Number: 69-33-0
• PubChem SID: 160966317; 46505938
• PubChem CID: 46936593

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.455672
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -2.802223
• LogD (pH = 7.4): -1.4866505
• Log P: -1.27846
• Molar Refractivity: 65.3716 cm^3
• Polarizability: 25.36341 Å^3
• Polar Surface Area: 126.65 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.83
• LOG S: -1.21
• Solubility (Water): 1.66e+01 g/l

PROPERTIES

Physical Property

• Solubility: 3 mg/mL [MERCK INDEX (1996)]
• Hydrophobicity(logP): -0.80 [HANSCH,C ET AL. (1995)]

DETAILS

DrugBank - DB03172

• Drug Groups: experimental
• Description: An antibiotic purine ribonucleoside that readily substitutes for adenosine in the biological system, but its incorporation into DNA and RNA has an inhibitory effect on the metabolism of these nucleic acids. [PubChem]
• References: Zimmerman TP, Wolberg G, Duncan GS: Metabolism of tubercidin and formycin to their 3':5'-cyclic nucleotides in mammalian cells. J Biol Chem. 1978 Dec 25;253(24):8792-7. [Pubmed]

REFERENCES

• Zimmerman TP, Wolberg G, Duncan GS: Metabolism of tubercidin and formycin to their 3':5'-cyclic nucleotides in mammalian cells. J Biol Chem. 1978 Dec 25;253(24):8792-7. Pubmed