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

• ChemBase ID: 171666
• Molecular Formular: C10H12IN5O4
• Molecular Mass: 393.13785
• Monoisotopic Mass: 392.99340189
• SMILES: n1c(nc2c(c1N)ncn2[C@H]1C([C@H]([C@H](O1)CO)O)O)I
• Canonical SMILES: OC[C@H]1O[C@H](C([C@H]1O)O)n1cnc2c1nc(I)nc2N
• InChI: InChI=1S/C10H12IN5O4/c11-10-14-7(12)4-8(15-10)16(2-13-4)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H2,12,14,15)/t3-,5+,6?,9-/m1/s1
• InChIKey: MGEBVSZZNFOIRB-ACJOCUEISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4R,5R)-2-(6-amino-2-iodo-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: (2R,4R,5R)-2-(6-amino-2-iodopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• Synonyms: 2-Iodoadenosine; 2-Iodo Adenosine

Database IDs

• CAS Number: 35109-88-7
• PubChem SID: 164227576
• PubChem CID: 44356940

CALCULATED PROPERTIES

• Acid pKa: 12.454002
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -1.0451063
• LogD (pH = 7.4): -1.0451071
• Log P: -1.0451033
• Molar Refractivity: 75.8987 cm^3
• Polarizability: 30.108912 Å^3
• Polar Surface Area: 139.54 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Hot Methanol; Water
• Apperance: Off-White Solid
• Melting Point: 202-203°C (dec.)

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - I686000

An intermediate in the synthesis of isoguanosine (crotonoside or 2-hydroxyadenosine), a naturally occuring nucleoside analogue of guanosine. Isoguanosine is incorporated into mammalian but not bacterial nucleic acids, stimulates the accumulation of cycli

REFERENCES

• Lowry, B.A., et al.: J. Biol. Chem., 197, 591 (1952)
• Huang, M., et al.: J. Med. Chem., 15, 462 (1952)
• Hagen, C., et al.: Biochem. Biophys. Acta, 293, 105 (1952)