(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-methyloxolane-3,4-diol

• ChemBase ID: 133195
• Molecular Formular: C10H13N5O3
• Molecular Mass: 251.24192
• Monoisotopic Mass: 251.1018393
• SMILES: C[C@@H]1[C@H]([C@H]([C@@H](O1)n1cnc2c1ncnc2N)O)O
• Canonical SMILES: C[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2N
• InChI: InChI=1S/C10H13N5O3/c1-4-6(16)7(17)10(18-4)15-3-14-5-8(11)12-2-13-9(5)15/h2-4,6-7,10,16-17H,1H3,(H2,11,12,13)/t4-,6-,7-,10-/m1/s1
• InChIKey: XGYIMTFOTBMPFP-KQYNXXCUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-methyloxolane-3,4-diol
• IUPAC Traditional name: 5'-deoxyadenosine
• Synonyms: 5′-dAdo; 5′-Deoxyadenosine

Database IDs

• CAS Number: 4754-39-6
• MDL Number: MFCD00056003
• PubChem SID: 162227472; 24893539
• PubChem CID: 439182

CALCULATED PROPERTIES

• Acid pKa: 12.4825115
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -1.1592125
• LogD (pH = 7.4): -1.0457197
• Log P: -1.0440539
• Molar Refractivity: 61.6519 cm^3
• Polarizability: 23.860281 Å^3
• Polar Surface Area: 119.31 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• RTECS: AU7358650
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

DETAILS

Sigma Aldrich - D1771

Application
5′-deoxyadenosine (5′dADO) is a substrate of bacterial methylthioadenosine/S-adenosylhomocysteine (MTA/SAH) nucleosidase and a product inhibitor produced by radical SAM enzymes. 5′-dADO may be useful to study the specificity and distribution of radical S-adenosyl-L-methionine enzymes.