(2R,3S,5R)-2-(hydroxymethyl)-5-[6-(methylamino)-9H-purin-9-yl]oxolan-3-ol

• ChemBase ID: 133213
• Molecular Formular: C11H15N5O3
• Molecular Mass: 265.2685
• Monoisotopic Mass: 265.11748937
• SMILES: CNc1c2c(ncn1)n(cn2)[C@H]1C[C@@H]([C@H](O1)CO)O
• Canonical SMILES: OC[C@H]1O[C@H](C[C@@H]1O)n1cnc2c1ncnc2NC
• InChI: InChI=1S/C11H15N5O3/c1-12-10-9-11(14-4-13-10)16(5-15-9)8-2-6(18)7(3-17)19-8/h4-8,17-18H,2-3H2,1H3,(H,12,13,14)/t6-,7+,8+/m0/s1
• InChIKey: DYSDOYRQWBDGQQ-XLPZGREQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,5R)-2-(hydroxymethyl)-5-[6-(methylamino)-9H-purin-9-yl]oxolan-3-ol
• IUPAC Traditional name: N6-methyl-2'-deoxyadenosine
• Synonyms: N6-Me-dAdo; N6-Methyl-2′-deoxyadenosine

Database IDs

• CAS Number: 2002-35-9
• MDL Number: MFCD00055999
• PubChem SID: 162227490; 24896727
• PubChem CID: 168948

CALCULATED PROPERTIES

• Acid pKa: 13.886735
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -0.9856721
• LogD (pH = 7.4): -0.88999236
• Log P: -0.88862175
• Molar Refractivity: 67.1783 cm^3
• Polarizability: 25.684137 Å^3
• Polar Surface Area: 105.32 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

DETAILS

Sigma Aldrich - M2389

Biochem/physiol Actions
N6-Methyl-2′-deoxyadenosine (N6-Me-dAdo) is a precursor of N6-methyl 2′-deoxyadenosine 3′,5′-bisphosphate (N6MABP), a competitive and selective inhibitor of P2Y1 receptors.