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

• ChemBase ID: 171875
• Molecular Formular: C13H15N5O5
• Molecular Mass: 321.2887
• Monoisotopic Mass: 321.10731861
• SMILES: n1cnc2c(c1N)ncn2[C@H]1[C@H]2[C@@H]([C@H](O1)C(=O)O)OC(O2)(C)C
• Canonical SMILES: OC(=O)[C@H]1O[C@H]([C@H]2[C@@H]1OC(O2)(C)C)n1cnc2c1ncnc2N
• InChI: InChI=1S/C13H15N5O5/c1-13(2)22-6-7(23-13)11(21-8(6)12(19)20)18-4-17-5-9(14)15-3-16-10(5)18/h3-4,6-8,11H,1-2H3,(H,19,20)(H2,14,15,16)/t6-,7+,8-,11+/m0/s1
• InChIKey: RRTBBKSJPNRFCG-MCHASIABSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3aS,4S,6R,6aR)-6-(6-amino-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-aminopurin-9-yl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylic acid
• Synonyms: 1-(6-Amino-9H-purin-9-yl)-1-deoxy-2,3-O-(1-methylethylidene)-β-D-ribofuranuronic Acid; NSC 143678; 2',3'-Isopropylidene Adenosine-5'-carboxylic Acid

Database IDs

• CAS Number: 19234-66-3
• PubChem SID: 164227785
• PubChem CID: 6360979

CALCULATED PROPERTIES

• Acid pKa: 3.2899096
• H Acceptors: 9
• H Donor: 2
• LogD (pH = 5.5): -2.2582242
• LogD (pH = 7.4): -3.469553
• Log P: -1.7319622
• Molar Refractivity: 75.27 cm^3
• Polarizability: 29.417967 Å^3
• Polar Surface Area: 134.61 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: White to Off-White Solid
• Melting Point: 276-279°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - I824695

Used in the preparation of nucleosides as adenosine A3 receptor agonists.

REFERENCES

• Bloch, A., et al.: J. Med. Chem., 10, 908 (1967)
• Wolfenden, R., et al.: J. Biol. Chem., 242, 977 (1967)
• Wilson, D., et al.: Biochemistry, 32, 1689 (1967)