(3aS,4S,6R,6aR)-6-(6-amino-2-iodo-9H-purin-9-yl)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxole-4-carboxylic acid

• ChemBase ID: 171669
• Molecular Formular: C13H14IN5O5
• Molecular Mass: 447.18523
• Monoisotopic Mass: 447.00396657
• SMILES: [C@H]1([C@@H]2[C@H]([C@@H](O1)n1c3nc(nc(c3nc1)N)I)OC(O2)(C)C)C(=O)O
• Canonical SMILES: OC(=O)[C@H]1O[C@H]([C@H]2[C@@H]1OC(O2)(C)C)n1cnc2c1nc(I)nc2N
• InChI: InChI=1S/C13H14IN5O5/c1-13(2)23-5-6(24-13)10(22-7(5)11(20)21)19-3-16-4-8(15)17-12(14)18-9(4)19/h3,5-7,10H,1-2H3,(H,20,21)(H2,15,17,18)/t5-,6+,7-,10+/m0/s1
• InChIKey: BPWZMRNNBQGXEV-HEZDBXPZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3aS,4S,6R,6aR)-6-(6-amino-2-iodo-9H-purin-9-yl)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxole-4-carboxylic acid
• IUPAC Traditional name: (3aS,4S,6R,6aR)-6-(6-amino-2-iodopurin-9-yl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylic acid
• Synonyms: 1-(6-Amino-2-iodo-9H-purin-9-yl)-1-deoxy-2,3-O-(1-methylethylidene)-β-D-ribofuranuronic Acid; 2-Iodo Adenosine 5'-Carboxy-2',3'-acetonide

Database IDs

• CAS Number: 141018-26-0
• PubChem SID: 164227579
• PubChem CID: 14999718

CALCULATED PROPERTIES

• Acid pKa: 2.6326022
• H Acceptors: 9
• H Donor: 2
• LogD (pH = 5.5): -1.806712
• LogD (pH = 7.4): -2.5275924
• Log P: 0.97759587
• Molar Refractivity: 87.9731 cm^3
• Polarizability: 34.97022 Å^3
• Polar Surface Area: 134.61 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Off-White Powder

DETAILS

Toronto Research Chemicals - I686750

Used for preparing 2-alkynyl-adenosine nucleosides as potential adenosine receptor agonists.

REFERENCES

• Cristalli, G., et al.: J. Med. Chem., 38, 1462 (1995)
• Cristalli, G., et al.: Drug Dev. Res., 45, 176 (1995)
• Klotz, K., et al.: Eur. J. Pharmacol., 556, 14 (1995)