(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-{[(2S)-1-phenylpropan-2-yl]amino}-9H-purin-9-yl)oxolane-3,4-diol

• ChemBase ID: 132079
• Molecular Formular: C19H23N5O4
• Molecular Mass: 385.41702
• Monoisotopic Mass: 385.17500424
• SMILES: C[C@@H](Cc1ccccc1)Nc1c2c(ncn1)n(cn2)[C@H]1[C@@H]([C@@H]([C@H](O1)CO)O)O
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2N[C@H](Cc1ccccc1)C
• InChI: InChI=1S/C19H23N5O4/c1-11(7-12-5-3-2-4-6-12)23-17-14-18(21-9-20-17)24(10-22-14)19-16(27)15(26)13(8-25)28-19/h2-6,9-11,13,15-16,19,25-27H,7-8H2,1H3,(H,20,21,23)/t11-,13+,15+,16+,19+/m0/s1
• InChIKey: RIRGCFBBHQEQQH-KFAHYOAQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-{[(2S)-1-phenylpropan-2-yl]amino}-9H-purin-9-yl)oxolane-3,4-diol
• IUPAC Traditional name: (2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-{[(2S)-1-phenylpropan-2-yl]amino}purin-9-yl)oxolane-3,4-diol
• Synonyms: (S)-N6-(1-Methyl-2-phenylethyl)adenosine; (S)-PIA; N6-(D-2-Phenylisopropyl)adenosine; (+)-N6-(2-Phenylisopropyl)adenosine

Database IDs

• CAS Number: 38594-97-7
• MDL Number: MFCD00055058
• PubChem SID: 162226356
• PubChem CID: 5312112

CALCULATED PROPERTIES

• Acid pKa: 12.453988
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): 0.55383533
• LogD (pH = 7.4): 0.6392379
• Log P: 0.6404496
• Molar Refractivity: 102.4754 cm^3
• Polarizability: 39.453266 Å^3
• Polar Surface Area: 125.55 Å^2
• Rotatable Bonds: 6
• 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

DETAILS

Sigma Aldrich - P7665

Biochem/physiol Actions
A1 adenosine receptor agonist
Other Notes
Less active isomer