[(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-(6-oxo-6,9-dihydro-1H-purin-9-yl)oxolan-2-yl]methyl acetate

• ChemBase ID: 119398
• Molecular Formular: C16H18N4O8
• Molecular Mass: 394.33612
• Monoisotopic Mass: 394.11246356
• SMILES: n1(c2c(nc1)c(=O)[nH]cn2)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(=O)C)OC(=O)C)OC(=O)C
• Canonical SMILES: CC(=O)O[C@@H]1[C@H](OC(=O)C)[C@H](O[C@H]1n1cnc2c1nc[nH]c2=O)COC(=O)C
• InChI: InChI=1S/C16H18N4O8/c1-7(21)25-4-10-12(26-8(2)22)13(27-9(3)23)16(28-10)20-6-19-11-14(20)17-5-18-15(11)24/h5-6,10,12-13,16H,4H2,1-3H3,(H,17,18,24)/t10-,12-,13-,16-/m1/s1
• InChIKey: SFEQTFDQPJQUJM-XNIJJKJLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-(6-oxo-6,9-dihydro-1H-purin-9-yl)oxolan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-(6-oxo-1H-purin-9-yl)oxolan-2-yl]methyl acetate
• Synonyms: (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-oxo-1H-purin-9(6H)-yl)tetrahydrofuran-3,4-diyl diacetate; NSC 66386; 2',3',5'-Tri-O-acetylinosine

Database IDs

• CAS Number: 3181-38-2
• PubChem SID: 162108061
• PubChem CID: 96313

CALCULATED PROPERTIES

• Acid pKa: 8.933924
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): -1.1553084
• LogD (pH = 7.4): -1.1662351
• Log P: -1.1551619
• Molar Refractivity: 88.7863 cm^3
• Polarizability: 34.722054 Å^3
• Polar Surface Area: 147.41 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Crystalline Solid
• Melting Point: 234-236°C

Safety Information

• Storage Warning: Freezer

DETAILS

Toronto Research Chemicals - T765500

An intermediate used for the synthesis of 6-substituted purine ribosides.