2-amino-7-[(2R,3S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H,4H,7H-pyrrolo[2,3-d]pyrimidin-4-one

• ChemBase ID: 165472
• Molecular Formular: C11H14N4O5
• Molecular Mass: 282.25266
• Monoisotopic Mass: 282.09641957
• SMILES: [C@@H]1(C([C@H](O[C@H]1n1c2c(cc1)c(=O)[nH]c(n2)N)CO)O)O
• Canonical SMILES: OC[C@H]1O[C@H]([C@H](C1O)O)n1ccc2c1nc(N)[nH]c2=O
• InChI: InChI=1S/C11H14N4O5/c12-11-13-8-4(9(19)14-11)1-2-15(8)10-7(18)6(17)5(3-16)20-10/h1-2,5-7,10,16-18H,3H2,(H3,12,13,14,19)/t5-,6?,7+,10-/m1/s1
• InChIKey: JRYMOPZHXMVHTA-ALELGUIPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-7-[(2R,3S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H,4H,7H-pyrrolo[2,3-d]pyrimidin-4-one
• IUPAC Traditional name: 2-amino-7-[(2R,3S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-pyrrolo[2,3-d]pyrimidin-4-one
• Synonyms: 2-Amino-7-(β-D-ribofuranosyl[3,2-d]pyrimidin-4-one; 2-Amino-1,7-dihydro-7-β-D-ribofuranosyl-4H-pyrrolo[2,3-d]pyrimidin-4-one; 7-Deazaguanosine

Database IDs

• CAS Number: 62160-23-0
• PubChem SID: 162259605
• PubChem CID: 59796171

CALCULATED PROPERTIES

• Acid pKa: 11.071586
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -2.3781664
• LogD (pH = 7.4): -1.9011165
• Log P: -1.8937144
• Molar Refractivity: 66.7971 cm^3
• Polarizability: 25.123903 Å^3
• Polar Surface Area: 142.33 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Off-White Solid
• Melting Point: >250°C dec

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D201390

A guanosine analogue

REFERENCES

• Gonzalez-Diaz, H., et al.: Bioorg. Med. Chem. Lett., 15, 1651 (2005)
• Lunn, F., et al.: J. Biol. Chem., 283, 2010 (2005)